Bicyclic amino derivatives and PGD2 antagonist containing the same

[0007] This application is a divisional of application Ser. No. 08/973,983, filed Apr. 22, 1998, which is a National Stage of PCT/JP96/01685, filed Jun. 19, 1996.

[0008] The present invention relates to bicyclic amino derivatives and prostaglandin D₂(hereinafter, referred to as PGD₂) antagonist containing them.

[0009] Some of bicyclic amino derivatives of the present invention have known to be useful as thromboxane A₂(TXA₂) antagonists (Japanese Patent Publication (KOKOKU) No. 79060/1993). However, the Japanese Patent Publication (KOKOKU) No. 79060/1993 only describes that the compounds are useful as TXA₂antagonist, and does not suggest the usefulness thereof as PGD₂antagonist as disclosed by the present invention.

[0010] Namely, the TXA₂is known to have activities such as action against platelet agglutination, thrombogenesis, etc. The TXA₂antagonist has therefore been considered to be useful as anti-thrombotic agent, and also in the treatment of myocardial infarction or asthma by antagonizing against TXA₂.

[0011] On the other hand, the PGD₂antagonist of the present invention is useful in the improvement of conditions due to excessive production of PGD₂. Specifically, it is useful as a drug for treating diseases in which mast cell dysfunction is involved, for example, systemic mastocytosis and disorder of systemic mast cell activation, and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, injury due to ischemic reperfusion, and inflammation.

[0012] As is apparent from the above, the TXA₂antagonist and the PGD₂antagonist are completely different from each other in terms of the active site, mechanism of action, and application, and have quite different characteristics. Accordingly, it has never been expected that any compound could possess these activities simultaneously.

[0013] PGD₂is produced through PGG₂and PGH₂from arachidonic acid by the action of cyclooxygenase activated by immunological or unimmunological stimulation and is the major prostanoid that is produced and released from mast cells. PGD₂has various potent physiological and pathological activities. For example, PGD₂can cause strong tracheal contraction, which leads to bronchial asthma, and, in a systemic allergic state, it can dilate the peripheral vessels, which leads to an anaphylactic shock. Especially, much attention has been paid on the idea that PGD₂is one of the causal substances responsible to the onset of nasal occlusion in the allergic rhinitis. Therefore, it has been proposed to develop an inhibitor against the biosynthesis of PGD₂or an antagonist of PGD₂receptor as a drug for the reduction of nasal occlusion. However, the inhibitor of PGD₂biosynthesis possibly affects greatly the synthesis of prostaglandins in other organisms, and therefore, it is desirable to develop an antagonist (blocker) specific to PGD₂receptor.

[0014] The present inventors have studied intensively to develop PGD₂receptor antagonists (blockers) specific to PGD₂receptor, and found that compounds of the formula (I) below or its salt possess a potent activity as PGD₂receptor antagonist, and are chemically and biochemically stable.

[0015] Accordingly, the present invention provides a PGD₂antagonist which comprises a compound of the general formula (I) below or its salt or a hydrate thereof as an active ingredient:

[0016] wherein

[0017] A is alkylene which optionally is intervened by hetero atom or phenylene, contains oxo group, and/or has an unsaturated bond;

[0018] B is hydrogen, alkyl, aralkyl or acyl;

[0019] R is COOR₁, CH₂OR₂or CON(R₃)R₄;

[0020] R₁is hydrogen or alkyl;

[0021] R₂is hydrogen or alkyl;

[0022] R₃and R₄each are independently hydrogen, alkyl, hydroxy or alkylsulfonyl;

[0023] X₁is a single bond, phenylene, naphtylene, thiophenediyl, indolediyl, or oxazolediyl;

[0024] X₂is a single bond, —N═N—, —N═CH—, —CH═N—, —CH═N—N—, —CH═N—O—, —C═NNHCSNH—, —C═NNHCONH—, —CH═CH—, —CH(OH)—, —C(Cl)═C(Cl)—, —(CH₂)_n—, ethynylene, —N(R₅)—, —N(R₅₁)CO—, —N(R₅₂)SO₂—, —N(R₅₃)CON(R₅₄)—, —CON(R₅₅)— —SO₂N(R₅₆)—, —O—, —S—, —SO—, —SO₂—, —CO—, oxadiazolediyl, thiadiazolediyl or tetrazolediyl;

[0025] X₃is alkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclic group, cycloalkyl, cycloalkenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl, —CH═NR₆or —N═C(R₇)R₈; R₅, R₅₁, R₅₂, R₅₃, R₅₄, R₅₅and R₅₆each are hydrogen or alkyl;

[0026] R₆is hydrogen, alkyl, hydroxy, alkoxy, carbamoyloxy, thiocarbamoyloxy, ureido or thioureido;

[0027] R₇and R₈each are independently alkyl, alkoxy or aryl;

[0028] n is 1 or 2;

[0029] Z is —SO₂— or —CO—; and

[0030] m is 0 or 1;

[0031] wherein a cyclic substituent may has one to three substituents selected from the group consisting of nitro, alkoxy, sulfamoyl, substituted- or unsubstituted-amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hlydroxyalkyl, trifluoromethyl, alkylthio, —N═PPh₃, oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy.

[0032] Specific examples of compounds usable as a PGD₂antagonist above include a compound of the formula (I) wherein

[0033] m is 0; and when Z is SO₂, both X₁and X₂are a single bond; X₃is alkyl, phenyl, naphthyl, stylyl, quinolyl or thienyl; and a cyclic substituent among these substituents optionally has one to three substituents selected from a group consisting of nitro, alkoxy, substituted- or unsubstituted-amino, halogen, alkyl and hydroxyalkyl, or its salt or hydrate thereof.

[0034] Similarly, specific examples include a compound of the formula (I) wherein

[0035] when m is 1, both X₁and X₂are a single bond; and X₃is phenyl optionally substituted with halogen, or its salt or hydrate thereof.

[0036] Similarly, specific examples include a compound of the formula (I) wherein

[0037] when m is 1, X₁is phenyl, X₂is —CH₂— or —N═N— and X₃is phenyl, or its salt or hydrate thereof.

[0038] Similarly, examples of compounds of the formula (I) include those of the formula (Ia):

[0039] wherein A, B, R, X₁, X₂and X₃are as defined above, or its salt or hydrate thereof, provided that those wherein (1) X¹and X₂are a single bond, and X₃is substituted- or unsubstituted-phenyl, or naphthyl; and (2) A is 5-heptenylene, R is COOR₁(R₁is hydrogen or methyl), X¹is 1,4-phenylene, X₂is a single bond, and X₃is phenyl are excluded.

[0040] Similarly, examples of compounds of the formula (I) include those of the formula (Ib):

[0041] wherein

[0042] A, B, R, X₁, X₂and X₃are as defined above, or its salt or hydrate thereof, provided that those wherein X₁and X₂are a single bond, and X₃is phenyl, and wherein X₁is a single bond, X₂is —O—, and X₃is benzyl are excluded.

[0043] More specifically, examples of compounds of the formula (I) include those of the formula (Ia) wherein X₁and X₂are a single bond, X₃is isoxazolyl, thiadiazolyl, isothiazolyl, morpholyl, indolyl, benzofuryl, dibenzofuryl, dibenzodioxinyl, benzothienyl, dibenzothienyl, carbazolyl, xanthenyl, phenanthridinyl, dibenzoxepinyl, dibenzothiepinyl, cinnolyl, chromenyl, benzimidazolyl or dihydrobenzothiepinyl, or its salt or hydrate thereof.

[0044] Similarly, examples of compounds of the formula (I) include those of the formula (Ia) wherein X₁is a single bond, X₂is phenylene, X₃is alkenyl, alkynyl, —CH═NR₆or —N═C(R₇)R₈, or its salt or hydrate thereof.

[0045] Similarly, examples of compounds of the formula (I) include those of the formula (Ia) wherein R is COOR₁, X₁is phenylene or thiophenediyl, X₂is a single bond, —N═N—, —CH═CH—, —CONH—, —NHCO— or ethynylene and X₃is phenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl or thienyl, or its salt or hydrate thereof.

[0046] More specifically, examples of the compound (I) of the present invention include those of the formula (Ib) wherein

[0047] or its salt or hydrate thereof. Examples of more preferred compounds include those of the formula (Ib) wherein R is COOR₁(R₁is as defined above) or its salt or hydrate thereof.

[0048] Similarly, examples of compound (I) include those of the formula (Ib) wherein X₁is phenylene or thiophenediyl, X₂is a single bond, —N═N—, —CH═CH—, ethynylene, —O—, —S—, —CO—, —CON(R₅₅)— (R₅₅is as defined above), —N(R₅₁)CO— (R₅₁is as defined above) and X₃is phenyl, or its salt or hydrate thereof.

[0049] More specifically, examples of compound (I) include those of the formula (Ib) wherein

[0050] or its salt or hydrate thereof. Examples of more preferred embodiment include those wherein B is hydrogen, both X₁and X₂are a single bond, X₃is thienyl, thiazolyl, thiadiazolyl, isothiazolyl, pyrrolyl, pyridyl, benzofuryl, benzimidazolyl, benzothienyl, dibenzofuryl, dibenzothienyl, quinolyl or indolyl or its salt or hydrate thereof. Similarly, examples include those wherein X₁is phenylene, thiophenediyl, indolediyl or oxazolediyl, X₂is a single bond, —N═N—, —CH═CH—, ethynylene, —S— or —O—, and X₃is aryl or heterocyclic group, or its salt or hydrate thereof.

[0051] The compounds of the general formula (Ia) and (Ib) are novel compounds synthesized by the present inventors.

[0052] The terms used throughout the present specification are as defined below.

[0053] The term “alkylene” means C₁-C₉straight or branched chain alkylene, for example, methylene, methylmethylene, dimethylmethylene, methylethylmethylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethyene, nonamethylene , or the like. The alkylene above can be intervened by a hetero atom(s) (oxygen, sulfur, nitrogen atom, or the like) or phenylene (e.g., 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, or the like), contain an oxo group, and/or have one or more double- or triple-bonds at any positions on the chain. Examples include —(CH₂)₂—O—CH₂—, —(CH₂)₂—O—(CH₂)₂—, —(CH₂)₂—O—(CH₂)₃—, —(CH₂)₂—O—(CH₂)₄—, —(CH₂)₂—O—(CH₂)₅—, —(CH₂)₂—O—(CH₂)₆—, —(CH₂)₂—S—(CH₂)₂—, —(CH₂)₃—S—(CH₂)₂—, —CH₂—S—CH₂—, —CH₂—S—(CH₂)₄—, —CH₂—N(CH₃)—CH₂—, —CH₂—NH—(CH₂)₂—, —(CH₂)₂—N(CH₂CH₃)—(CH₂)₃—, —(CH₂)₂-1,4-phenylene-CH₂—, —(CH₂)₂—O-1,3-phenylene-CH₂—, —(CH₂)₂—O-1,2-phenylene-CH₂—, —(CH₂)2—O-1,4-phenylene-CH₂—, —CH═CH—S—CH₂-1,4-phenylene-CH₂—, —CH—CH—S-1,3-phenylene-(CH₂)₂—, 2-oxopropylene, 3-oxopentylene, 5-oxohexylene, vinylene, 1-propenylene, 2-propenylene, 1-butenylene, 2-butenylene, 3-butenylene, 1,2-butadienylene, 1,3-butadienylene, 1-pentenylene, 2-pentenylene, 3-pentenylene, 4-pentenylene, 1,2-pentadienylene, 1,3-pentadienylene, 1,4-pentadienylene, 2,3-pentadienylene, 2,4-pentadienylene, 1-hexyenylene, 2-hexenylene, 3-hexenylene, 4-hexenylene, 5-hexenylene, 1,2-hexadienylene, 1,3-hexadienylene 1,4-hexadienylene, 1,5-hexadienylene, 2,3-hexadienylene, 2,4-hexadienylene 2,5-hexadienylene, 3,4-hexadienylene, 3,5-hexadienylene, 4,5-hexadienylen, 1,1-dimethyl-4-hexenylen, 1-heptenylene, 2-heptenylene, 3-heptenylene, 4-heptenylene, 5-heptenylene, 2,2-dimethyl-5-heptenylene, 6-heptenylene, 1,2-hexadienylene, 1,3-heptadienylene, 1,4-heptadienylene, 1,5-heptadienylene, 1,6-heptadienylene, 2,3-heptadienylene, 2,4-heptadienylene, 2,5-heptadienylene, 2,6-heptadienylene, 3,4-heptadienylene, 3,5-heptadienylene, 3,6-heptadienylene, 4,5-heptadienylene, 4,6-heptadienylene or 5,6-heptadienylene, 1-propynylene, 3-butynylene, 2-pentynylene, 5-hexynylene, 6-heptynylene, —(CH₂)—CH═CH—O—(CH₂)₂—, —CH₂—S—(CH₂)₃—, —CH₂-cis-CH═CH-1,2-phenylene-CH₂—, —CH═CH-1,4-phenylene-(CH₂)₂—, -4-oxo-4,5-hexenylene-, and the like.

[0054] The term “alkyl” means C₁-C₂₀straight or branched chain alkyl, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, and the like.

[0055] The term “aryl” means C₆-C₁₄monocyclic or condensed ring, for example, phenyl, naphthyl (e.g., 1-naphthyl, 2-naphtyl), anthryl (e.g., 1-anthryl, 2-anthryl, 9-anthryl), phenanthryl (e.g., 2-phenanthryl, 3-phenanthryl, 9-phenanthryl), fluorenyl (e.g., 2-fluorenyl), and the like. Phenyl is especially preferred.

[0056] The term “aralkyl” means a group formed by substituting an alkyl as defined above with an aryl above at any substitutable positions on the alkyl. Examples include benzyl, phenethyl, phenylpropyl (e.g., 3-phenylpropyl), naphtylmethyl (e.g., α-naphtylmethyl), anthrylmethyl (e.g., 9-anthrylmethy), phenanthrylmethyl (e.g., 3-phenanthrylmethyl), and the like.

[0057] The term “acyl” means C₁-C₉acyl derived from aliphatic carboxylic acid, for example, formyl, acetyl, propionyl, butyryl, valeryl, and the like.

[0058] The term “alkylsulfonyl” means a group formed by substituting a sulfonyl with an alkyl above, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, and the like.

[0059] The term “alkenyl” is C₂-C₂₀straight or branched chain alkenyl, which corresponds to an alkyl above containing one or more double bonds. Examples include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,2-butadienyl, 1-pentenyl, 1,2-pentadienyl, 2-hexyenyl, 1,2-hexadienyl, 3-heptenyl, 1,5-heptadienyl, and the like.

[0060] The term “alkynyl” is C₂-C₂₀straight or branched chain, alkynyl, which corresponds to an alkyl above containing one or more triple bonds. Examples include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and the like.

[0061] The term “heterocyclic group” means 5-7 membered cyclic group containing one or more hetero atoms selected independently from the group consisting of oxygen, sulfur and/or nitrogen atom on the ring, and is optionally condensed with a carbon ring or other heterocyclic group at any substitutable positions. Examples include pyrrolyl (e.g., 1-pyrrolyl, 3-pyrrolyl), indolyl (e.g., 2-indolyl, 3-indolyl, 6-indolyl), carbazolyl (e.g., 2-carbazolyl, 3-carbazolyl), imidazolyl (e.g., 1-imidazolyl, 4-imidazolyl), pyrazolyl (e.g., 1-pyrazolyl, 3-pyrazolyl), benzimidazolyl (e.g., 2-benzimidazolyl, 5-benzimidazolyl), indazolyl (e.g., 3-indazolyl), indolizinyl (e.g., 6-indolyzinyl), pyridyl (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl), quinolyl (e.g., 8-quinolyl), isoquinolyl (e.g., 3-isoquinolyl), acridyl (e.g., 1-acridyl), phenanthrydinyl (e.g., 2-phenanthrydinyl, 3-phenanthrydinyl), pyridazinyl (e.g., 3-pydidazinyl), pyrimidinyl (e.g., 4-pyrimidinyl), pyrazinyl (e.g., 2-pyrazinyl), cinnolinyl (e.g., 3-cinnolinyl), phthaladinyl (e.g., 5-phthaladinyl), quinazolinyl (e.g., 2-quinazolinyl), isoxazolyl (e.g., 3-isoxazolyl, 4-isoxazolyl), benzisoxazolyl (e.g., 1,2-benzisoxazol-4-yl, 2,1-benzisoxazol-3-yl), oxazolyl (e.g., 2-oxazolyl, 4-oxazolyl, 5-oxazolyl), benzoxazolyl (e.g., 2-benzoxazolyl), benzoxadiazolyl (e.g., 4-benzoxadiazolyl), isothiazolyl (e.g., 3-isothiazolyl, 4-isothiazolyl) benzisothiazolyl (e.g., 1,2-benzisothiazol-3-yl, 2,1-benzisothizol-5-yl), thiazolyl (e.g., 2-thiazolyl), benzothiazolyl (e.g., 2-benzothiazolyl), thiadiazolyl (e.g., 1,2,3-thiadiazol-4-yl), oxadiazolyl (e.g., 1,3,4-oxadiazol-2-yl), dihydroxadiazolyl (e.g., 4,5-dihydro-1,2,4-oxadiazol-3-yl), furyl (e.g., 2-furyl, 3-furyl), benzofuryl (e.g., 3-benzofuryl), isobenzofuryl (e.g., 1-isobenzofuryl), thienyl (e.g., 2-thienyl, 3-thienyl), benzothienyl (1-benzothiophen-2-yl, 2-benzothiophen-1-yl), tetrazolyl (e.g., 5-tetrazolyl), benzodioxolyl (e.g., 1,3-benzodioxol-5-yl), dibenzofuryl (e.g., 2-dibenzofuryl, 3-dibenzofuryl), dibenzoxepinyl (e.g., dibenz[b,f]oxepin-2-yl), dihydrodibenzoxepinyl (e.g., dihydrodibenz[b,f]oxepin-2-yl, chromenyl (e.g., 2H-chromen-3-yl, 4H-chromen-2-yl), dibenzothiepinyl (e.g., dibenzo[b,f]thiepin-3-yl, dihydrodibenzo[b,f]thiepin-3-yl), morpholinyl (e.g., 1,4-morpholin-4-yl), phenothiadinyl (2-phenothiadinyl), cyclopentathienyl (e.g., cyclopenta[b]thiophen-3-yl), cyclohexathienyl (e.g., cyclohexa[b]thiophen-3-yl), and the like.

[0062] The term “cycloalkyl” means C₃-C₈cyclic alkyl, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

[0063] The term “cycloalkenyl” means C₃-C₈cyclic alkenyl, for example, cyclopropenyl (e.g., 1-cyclopropenyl), cyclobutenyl (e.g., 2-cyclobuten-1-yl), cyclopentenyl (1-cyclopenten-1-yl), cyclohexenyl (1-cyclohexen-1-yl), and the like.

[0064] The term “alkoxy” means C₁-C₆alkoxy, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, and the like.

[0065] Examples of the substituted amino in the definition of “substituted- or un-substituted-amino” include mono- or di-substituted amino such as methylamino, ethylamino, dimethylamino, cyclohexylamino, phenylamino, diphenylamino, or cyclic amino such as piperidino, piperadino or morpholino.

[0066] The term “acyloxy” means an acyloxy derived from the “acyl” above, for example, acetyloxy, propionyloxy, butyryloxy, valeryloxy, and the like.

[0067] The term “halogen” means fluorine, chlorine, bromine and iodine.

[0068] The term “alkoxycarbonyl” means an alkoxycarbonyl group derived from the “alkoxy” above, for example, methoxycarbonyl, ethoxycarbonyl, phenyloxycarbonyl, and the like.

[0069] The term “aralkyloxycarbonyl” means an aralkyloxycarbonyl group derived from the “aralkyl” above, for example, benzyloxycarbonyl, phenethyloxycarbonyl, and the like.

[0070] The term “aryloxycarbonyl” means an aryloxycarbonyl group derived from the “aryl” above, for example, phenyloxycarbonyl, naphtyloxycarbonyl, and the like.

[0071] The term “alkenyloxy” means an alkenyloxy group derived from the “alkenyl” above, for example, vinyloxy, 1-propenyloxy, 2-butenyloxy, and the like.

[0072] The term “hydroxyalkyl” means a hydroxyalkyl group derived from the “alkyl” above, for example, hydroxymethyl, hydroxyethyl, hydroxypropyl, and the like.

[0073] The term “alkylthio” means an alkylthio group derived from the “alkyl” above, for example, methylthio, ethylthio, propylthio, and the like.

[0074] The term “alkylenedioxy” means C₁-C₃alkylenedioxy, for example, methylenedioxy, ethylenedioxty, propylenedioxy, and the like.

[0075] In the case of “phenylene, “naphtylene”, “thiophenediyl”, “indolediyl”, “oxazolediyl”, “oxadiazolediyl” and tetrazolediyl”, the said group can bind to the neighboring groups at any two substitutable sites.

[0076] In the definitions above, when a substituent(s) is cyclic, it may be substituted by one to three substituents selected from nitro, alkoxy, sulfamoyl, substituted- or un-substituted-amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, trifluoromethyl, alkylthio, —N═PPh₃, oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy. The substituent(s) may bind to any substitutable positions on the ring.

[0077] Examples of salts of the compound (I) include those formed with an alkali metal (e.g., lithium, sodium or potassium), an alkali earth metal (e.g., calcium), an organic base (e.g., tromethamine, trimethylamine, triethylamine, 2-aminobutane, t-butylamine, diisopropylethylamine, n-butylmethylamine, cyclohexylamine, dicyclohexylamine, N-isopropylcyclohexylamine, furfurylamine, benzylamine, methylbenzylamine, dibenzylamine, N,N-dimethylbenzylamine, 2-chlorobenzylamine, 4-methoxybenzylamine, 1-naphthylenemethylamine, diphenylbenzylamine, triphenylamine, 1-naphthylamine, 1-aminoanthoracene, 2-aminoanthoracene, dehydroabiethylamine, N-methylmorpholine or pyridine), an amino acid (e.g., lysine, or arginine), and the like.

[0078] The term “hydrate” means a hydrate of the compound of the formula (I) or its salt. Examples include. mono- and dihydrates.

[0079] The present compounds are shown by the formula (I) and are inclusive of the form of any types of stereoisomers (e.g., diastereomer, epimer, enantiomer) and racemic compounds.

[0080] Among the compounds of the general formula (I), those wherein m=1, especially, those shown in Tables 3b and 3c below are known compounds described in Japanese Patent Publication (KOKAI) No. 180862/1990.

[0081] Among the compounds of the general formula (I), those wherein m=0, [i.e., those shown by the general formula (I′)], can be prepared by reacting an amino compound of the general formula (II) with a reactive derivative of sulfonic acid or carboxylic acid corresponding to the partial structure: Z—X₁—X₂—X₃as shown below.

[0082] Wherein A, B, R, X₁, X₂, X₃, Y and Z are as defined above.

[0083] A sulfonic acid corresponding to the partial structure: Z—X₁—X₂—X₃is a compound of the general formula X₃—X₂—X₁—SO₂OH and a carboxylic acid corresponding to the said partial structure is a compound of the general formula X₃—X₂—X₁—COOH. Reactive derivative of these sulfonic or carboxylic acids means a corresponding halide (e.g., chloride, bromide, iodide), acid anhydride (e.g., mixed acid anhydride with formic acid or acetic acid), active ester (e.g., succinimide ester), and examples thereof generally include acylating agents used for the acylation of amino group. The carboxylic acid X₃—X₂—X₁—COOH can be used in the reaction as it is without converting into a reactive derivative, in the presence of a condensing agent (e.g., dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimetylaminopropyl)carbodiimide, N,N′-carbonyldiimidazole) which are used in the condensing reaction between amine and carboxylic acid.

[0084] The reaction can be conducted under the conditions generally used for the acylation of amino group. For example, in the case of condensation using an acidhalide, the reaction is carried out using a solvent such as an ether solvent (e.g., diethylether, tetrahydrofuran, dioxane), benzene solvent (e.g., benzene, toluene, xylene), halogenated hydrocarbon solvent (e.g., dichlorbmethane, dichloroethane, chloroform), ethyl acetate, dimethylformamide, dimethyl sulfoxide, acetonitrile, or the like, if necessary, in the presence of a base (e.g., organic base such as triethylamine, pyridine, N,N-dimethylaminopyridine, N-methylmorpholine; inorganic base such as sodium hydroxide, potassium hydroxide, potassium carbonate, or the like) under cooling, at room temperature or under heating, preferably at temperature ranging from −20° C. to a temperature under cooling, or from room temperature to a refluxing temperature of the reaction system, for several min to several hr, preferably for 0.5 hr to 24 hr, more preferably, for 1 hr to 12 hr.

[0085] The reaction conditions for the reaction between other reactive derivative or a free acid and an amine (II) can be determined in a conventional manner depending on the characteristics of the respective reactive derivative or free acid.

[0086] The reaction product can be purified by conventional purification methods, for example, the extraction with a solvent, chromatography, recrystallization, or the like.

[0087] Specific examples of the compound (II) as a starting material for the present method are as follows. Examples of 3-amino[2.2.1]bicyclic compound include 7-(3-aminobicyclo[2.2.1]hept-2-yl)-5-heptenoic acid, 7-(3-aminobicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-5-heptenoic acid, 7-(N-methyl-3-aminobicyclo[2.2.1]hept-2-yl)-5-heptenoic acid, 6-(3-aminobicyclo[2.2.1]hept-2-yl)-5-hexenoic acid. Specific examples of 2-amino-6,6-dimethyl[3.1.1]bicyclic compound include 7-(2-amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)-5-heptenoic acid. In these starting compounds, the heptenoic acid chain may be saturated to form heptanoic acid chain, intervened by a hetero atom(s) or a hetero group(s) such as —O—, —S—, —NH—, or a phenylene(s), or substituted with an oxo group. Examples of such compounds include 7-(3-aminobicyclo[2.2.1]hept-2-yl)heptanoic acid, 4-[2-(2-aminobicyclo[3.1.1]hept-3-yl)ethoxyphenylacetic acid, 7-(3-aminobicyclo[2.2.1]hept-2-yl)-6-oxo-heptanoic acid. These starting compounds are either described in the Japanese Patent Publication (KOKOKU) No. 79060/1993 or 23170/1991, or can be prepared according to the method described therein.

[0088] Sulfonic acid X₃—X₂—X₁—SO₂OH and carboxylic acid X₃—X₂—X₁—COOH corresponding to the partial structure Z—X₁—X₂—X₃mean a sulfonic acid or carboxylic acid having substituents corresponding to the Xs above. That is, examples include alkane-sulfonic acid or -carboxylic acid, alkene-sulfonic acid or -carboxylic acid, alkyne-sulfonic acid or -carboxylic acid, cycloalkane-sulfonic acid or -carboxylic acid, cycloalkene-sulfonic acid or -carboxylic acid, aryl-sulfonic acid or -carboxylic acid, aralkyloxy-sulfonic acid or -carboxylic acid, heterocyclic-substituted-sulfonic acid or -carboxylic acid, heteroarylalkyl-sulfonic acid or -carboxylic acid, and substituted-amino-sulfonic acid or -carboxylic acid. Each of sulfonic and carboxylic acids may have a substituent(s) above. These sulfonic acids and carboxylic acids are commercially available or can be easily synthesized from a known compound(s) in accordance with a known method. Upon reaction, the sulfonic or carboxylic acid can be converted into the corresponding reactive derivative above, if necessary. For example, when an acid halide is needed, the compound is reacted with thionyl halide (e.g., thionyl chloride), phosphorous halide (e.g., phosphorous trichloride, phosphorous pentachloride) or oxalyl halide (e.g., oxalyl chloride) in accordance with a known method such as those described in a literature (e.g., Shin-Jikken-Kagaku-Koza, vol. 14, pp. 1787 (1978); Synthesis, 852-854 (1986); Shin-Jikken-Kagaku-Koza, vol. 22, pp. 115 (1992)). The other reactive derivatives can also be prepared in accordance with a known method.

[0089] Among the objective compounds (I), those wherein the side chain A contains an unsaturated bond, especially, a double bond, can also be prepared by reacting an aldehyde derivative of the general formula (III) below with an ylide compound corresponding to the rest part of the side chain A—R under the conditions for the Wittig reaction:

[0090] wherein A, B, R, X₁, X₂, X₃, Y and Z are as defined above.

[0091] The starting compound (III) can be prepared in accordance with a method described in, for example, Japanese Patent Publication (KOKAI) No. 256650/1990. Further, an ylide compound corresponding to the rest part of the side chain A—R can be synthesized by reacting triphenylphosphine with a corresponding halogenated alkanoic acid, or an ester derivative, ether derivative or amide derivative thereof in the presence of a base according to a known method.

[0092] Among the objective compounds (I), those wherein R is COOH can be converted into a corresponding ester derivative, alcohol derivative, ether derivative, amide derivative, if desired. For example, ester derivatives can be prepared by esterifying a carboxylic acid in a conventional manner. An ester derivative, when reduced, gives an alcohol derivative, and amidated, gives an amide derivative. An ether derivative can be obtained by O-alkylating an alcohol derivative.

[0093] The compound (I) of the present invention shows antagonistic effect against PGD₂in vitro through the binding to PGD₂receptor, and is useful as a drug for treating diseases in which mast cell dysfunction due to excessive production of PGD₂is involved. For example, the compound (I) is useful as a drug for treating diseases, such as systemic mastocytosis and disorder of systemic mast cell activation, and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, injury due to ischemic reperfusion, and inflammation. The compound (I) shows preventive effect on nasal occlusion in vivo, and therefore is especially useful as a drug for treating them.

[0094] When using a compound (I) of the present invention in treatment, it can be formulated into ordinary formulations for oral and parenteral administration. A pharmaceutical composition containing a compound (I) of the present invention can be in the form for oral and parenteral administration. Specifically, it can be formulated into formulations for oral administration such as tablets, capsules, granules, powders, syrup, and the like; those for parenteral administration such as injectable solution or suspension for intravenous, intramuscular or subcutaneous injection, inhalant, eye drops, nasal drops, suppositories, or percutaneous formulations such as ointment.

[0095] In preparing the formulations, carriers, excipients, solvents, and bases known to one ordinary skilled in the art may be used. In case of tablets, they are prepared by compressing or fomulating an active ingredient together with auxiliary components. Examples of usable auxiliary components include pharmaceutically acceptable excipients such as binders (e.g., cornstarch), fillers (e.g., lactose, microcrystalline cellulose), disintegrants (e.g., starch sodium glycolate) or lubricants (e.g., magnesium stearate). Tablets may be coated appropriately. In the case of liquid formulations such as syrups, solutions, or suspensions, they may contain suspending agents (e.g., methyl cellulose), emulsifiers (e.g., lecithin), preservatives, and the like. In the case of injectable formulations, it may be in the form of solution or suspension, or oily or aqueous emulsion, which may contain suspension-stabilizing agent or dispensing agent, and the like. In the case of an inhalant, it is formulated into a liquid formulation applicable to an inhaler. In the case of eye drops, it is formulated into a solution or a suspension. Especially, in the case of nasal drug for treating nasal occlusion, it can be used as a solution or suspension prepared by a conventional formulating method, or as a powder formulated using a powdering agent (e.g., hydro-xypropyl cellulose, carbopole), which are administered into the nasal cavity. Alternatively, it can be used as an aerosol after filling into a special container together with a solvent of lowboiling point.

[0096] Although an appropriate dosage of the compound (I) varies depending on the administration route, age, body weight, sex, or conditions of the patient, and the kind of drug(s) used together, if any, and should be determined by the physician in the end, in the case of oral administration, the daily dosage can generally be between about 0.01-100 mg, preferably about 0.01-10 mg, more preferably about 0.1-10 mg, per kg body weight. In the case of parenteral administration, the daily dosage can generally be between about 0.001-100 mg, preferably about 0.001-1 mg, more preferably about 0.01-1 mg, per kg body weight. The daily dosage can be administered in 1-4 divisions.

[0097] The following Examples are provided to further illustrate the present invention and are not to be construed as limiting the scope thereof.

[0098]

[0099] Methyl (Z)-7-[(1S,2R,3R,4R)-3-aminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (II-1) (251 mg, 1.00 mmol) was dissolved in methylene chloride (8 ml) and triethylamine (0.238 ml, 2.00 mmol) was added thereto under a nitrogen atmosphere. To the mixture was added 2-chlorosulfonyldibenzofuran (350 mg, 1.31 mmol) under ice-cooling, and the mixture was stirred for 30 min and allowed to warm up to room temperature. The reaction mixture was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:4)) and recrystallized from n-hexane (10 ml) to yield methyl (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1a-1) (342 mg, 0.710 mmol). Yield 71%, mp 115-116° C.

[0100] Elemental analysis (C₂₇H₃₁NO₅S); Calcd. (%): C, 67.34; H, 6.49; N, 2.91; S, 6.66; Found (%): C, 67.16; H, 6.47; N, 2.99; S, 6.66; IR (CHCl₃): 3382, 3024, 2952, 2874, 1726, 1583, 1465, 1442, 1319, 1245, 1154, 1121, 1104, 1071, 1019, 890, 840, 817/cm. ¹H NMR (CDCl₃) δ: 0.94-1.92(14H, m), 2.15-2.24(3H, m), 2.99-3.07(1H, m), 3.66(3H, s), 4.98(1H, d, J=6.6 Hz), 5.10-5.22(2H, m), 7.39-7.46(1H, m), 7.51-7.70(3H, m), 7.87-8.13(2H, m), 8.53(1H, d, J=2.1 Hz); [α]_D=−0.6° (CHCl₃, c=1.01%, 23° C.). ([α]₃₆₅=+37.0° (CHCl₃, c=1.01%, 23° C.).

[0101] Methyl (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1a-1) (234 mg, 0.50 mmol) was dissolved in methanol (6 ml)/tetrahydrofuran (4 ml). To the solution was added 1 N potassium hydroxide (1.50 ml, 1.50 mmol) under ice-cooling. After the reaction mixture was warmed up to room temperature, it was allowed to react for 16 hr and concentrated to remove the solvent. To the residue were added ethyl acetate (50 ml) and water (10 ml), and then 1 N HCl (2.00 ml, 2.00 mmol), and the organic layer was separated. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:1) containing 0.2% acetic acid) to yield (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1a-2) (203 mg, 0.434 mmol). Yield 87%, oil.

[0102] IR (CHCl₃): 3266, 3026, 2952, 2874, 1708, 1465, 1443, 1423, 1319, 1267, 1245, 1153, 1121, 1104, 1072, 906/cm. ¹H NMR (CDCl₃) δ: 0.93-1.94(14H, m), 2.12-2.19(1H, m), 2.26(2H, t, J=7.2 Hz), 3.00-3.08(1H, m), 5.12-5.25(2H, m), 5.26(1H, d, J=6.6 Hz), 7.38-7.45(1H, m), 7.51-7.70(3H, m), 7.87-8.13(2H, m), 8.54(1H, d, J=2.1 Hz). [α]_D=+6.8° (CHCl₃, c=1.08%, 23° C.).

[0103] (Z)-7-[(1S,2R,3R,4R)-3-(2-Dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1a-2) (453 mg, 0.97 mmol) was dissolved in methanol (5 ml). After addition of 1 N sodium methoxide/methanol (1.034 N, 0.937 ml, 0.97 mmol), the mixture was allowed to warm up to room temperature and to react for 1 hr. The solvent was removed by distillation to yield the sodium salt (1a-3) (457 mg, 0.933 mmol). Yield 96%.

[0104] Amorphous powder. Elemental analysis (C₂₆H₂₈NO₅SNa 0.6H₂O); Calcd. (%): C, 62.41; H, 5.88; N, 2.80; S, 6.41; Na, 4.59; Found (%): C, 62.45; H, 5.92; N, 2.99; S, 6.49; Na, 4.46; IR (KBr): 434, 3280, 3074, 3007, 2952, 2873, 1566, 1467, 1444, 1417, 1344, 1315, 1270, 1248, 1200, 1189, 1154, 1124, 1107, 1075, 1058, 895, 842, 818/cm. ¹H NMR (CD₃OD) δ: 1.02-2.05(16H, m), 2.16-2.23(1H, m), 2.94-3.00(1H, m), 4.98-5.05(2H, m), 7.41-7.48(1H, m), 7.53-7.62(1H, m), 7.66(1H, d, J=8.4 Hz), 7.77(1H, d, J=8.4 Hz), 8.57(1H, d, J=2.1 Hz). [α]_D=−15.2° (CH₃OH, c=1.07%, 22° C.).

[0105]

[0106] Methyl (Z)-7-[(1S,2R,3R,4R)-3-aminobicyclo[2.2.1]hept-2-yl]-5-heptenoate trifrluroroacetate (II-2) (232 mg, 0.636 mmol), which was prepared by the method described in Reference Example 4 of the Japanese Patent Publication (KOKOKU) No. 79060/1993, was dissolved in methylene chloride (5 ml). To the solution were added triethylamine (0.279 ml, 2.00 mmol) and 4-biphenylcarbonyl chloride under ice-cooling and stirred for 7 hr at the same temperature. The reaction mixture was purified by column chromatography on silica gel (ethyl acetate/n-hexane (1:4)) to yield methyl (Z)-7-[(1S,2R,3R,4R)-3-(4-biphenyl)carbonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1k-11) (221mg, 0.512 mmol). The compound (1k-11) (190mg, 0.440mmol) was dissolved in methanol (6ml). To the solution was added 1 N KOH (1.10 ml, 1.10 mmol) under ice-cooling and stirred for 15 hr at room temperature. The reaction mixture was concentrated, in vacuo. The residue, after the addition of water (20 ml) and 1 N HCl (2 ml), was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane (1:1) containing 0.3% acetic acid) to yield (Z)-7-[(1S,2R,3R,4R)-3-(4-biphenyl)carbonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1k-12) (172 mg, 0.412 mmol). Yield 94%.

[0107] The following compounds can also be prepared in the following manner.

[0108]

[0109] To a suspension of 4-carboxybutyltriphenylphosphonium bromide (14.8 g, 33.3 mmol) and tetrahydrofuran (80 ml) was added potassium t-butyrate (7.55 g, 67.3 mmol) at room temperature under a nitrogen atmosphere. After stirring for 1 hr at room temperature, the mixture was cooled to −20° C. and a solution of N-[(1S,2S,3S,4R)-3-formylmethylbicyclo[2.2.1]hept-2-yl]benzenesulfonamide (III-1) (Japanese Patent Publication (KOKAI) No. 256650/1990, Reference Example 2) (3.25 g, 11.1 mmol) in tetrahydrofuran (20 ml) was added slowly. After stirring for about 1 hr at −20° C., the ice bath was removed and the mixture was further stirred for 1 hr. To the reaction solution was added 2 N HCl and the mixture was extracted with ethyl acetate, washed with water and brine, and concentrated. After the addition of toluene and 1 N sodium hydroxide to the resultant crude product, aqueous layer was separated. The organic layer was washed with water again and the washing was combined with the previously obtained aqueous layer. After the addition of 2 N HCl, the aqueous solution was extracted with ethyl acetate. The extract was washed with water and brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel to obtain calcium (Z)-7-[(1R,2S,3S,4S)-3-phenylsulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1d-1) (3.29 g, yield 79%, mp 62° C.).

[0110] Elemental analysis (C₂₀H₂₇NO₄S); Calcd. (%): C, 63.63; H, 7.21; N, 3.71; S, 8.49; Found (%): C, 63.56; H, 7.21; N, 3.83; S, 8.43; [α]_D=+5.3±0.5° (CHCl₃, c=1.003%, 22° C.); [α]_D=+27.1±0.7° (MeOH, c=1.015% 24° C.); IR (Nujol) 3282, 3260, 3300, 2400, 1708, 1268, 1248, 1202, 1162, 1153, 1095, 1076/cm. ¹H NMR δ 0.88-2.10(m, 14H), 2.14(br S, 1H), 2.34(t, J=7.2 Hz, 2H), 2.95-3.07(m, 1H), 5.13-5.35(m, 3H), 7.45-7.64(m, 3H), 7.85-7.94(m, 2H), 9.52(brS, 1H).

[0111] Compounds prepared in accordance with a method described in Examples above are shown in Tables below.

[0112] Physicochemical properties of compounds above are shown below. The compound number below corresponds to that described in Tables above.

[0113] No.1a-4

[0114] [α]_D=−11.5° (CHCl₃, c=1.01, 23.5° C.).

[0115] No.1a-5

[0116] [α]_D=−10.0° (CHCl₃, c=1.01, 25.0° C.).

[0117] No.1a-6

[0118] CDCl₃300 MHz 0.93-1.96(14H, m), 2.20-2.26(3H, m), 3.03(1H, m), 3.67(3H, s), 4.99(1H, d, J=6.6 Hz), 5.10-5.24(2H, m), 7.37-7.51(3H, m), 7.54-7.64(3H, m), 7.76-7.88(2H, m), 8.11(1H, m). IR (CHCl₃): 3384, 3278, 3026, 2952, 2874, 1727, 1436, 1411, 1324, 1155, 1097/cm. [α]_D=−9.0° (CHCl₃, c=1.04, 22.0° C.).

[0119] No.1a-7

[0120] CDCl₃300 MHz 0.93-2.00(14H, m), 2.18(1H, m), 2.28(2H, t, J=7.2 Hz), 3.04(1H, m), 5.15-5.25(2H, m), 5.28(1H, d, J=6.9 Hz), 7.36-7.50(3H, m), 7.54-7.63(3H, m), 7.76-7.89(2H, m), 8.12(1H, m). IR (CHCl₃): 3268, 3028, 2952, 2872, 1708, 1452, 1410, 1324, 1155, 1097/cm. [α]_D=−9.1° (CHCl₃, c=1.01, 24.0° C.).

[0121] No.1a-8

[0122] CDCl₃300 MHz; 0.94-1.99(14H, m), 2.21-2.29(3H, m), 3.05(1H, m), 3.67(3H, s), 4.92(1H, d, J=6.3 Hz), 5.14-5.30(2H, m), 7.70-7.78(6H, m), 7.96-8.01(2H, m). IR (CHCl₃): 3376, 3272, 3018, 2946, 2868, 1727, 1616, 1435, 1388, 1324, 1162, 1130, 1069/cm. [α]_D=+1.6° (CHCl₃, c=1.01, 24.0° C.). mp. 117-119° C.

[0123] No.1a-9

[0124] CDCl₃300 MHz; 0.95-2.08(14H, m), 2.19(1H, m), 2.32(2H, t, J=7.2 Hz), 3.06(1H, m), 5.20-5.30(2H, m), 5.34(1H, d, J=6.6 Hz), 7.69-7.78(6H, m), 7.96-8.03(2H, m). IR (CHCl₃): 3260, 3020, 2950, 2868, 1708, 1389, 1324, 1162, 1130, 1069/cm. [α]_D=+13.3° (CHCl₃, c=1.05, 24.0° C.). mp. 118-120° C.

[0125] No.1a-10

[0126] CDCl₃300 MHz; 0.96-1.98(14H, m), 2.15-2.32(3H, m), 3.04(1H, m), 3.66(3H, s), 5.12-5.26(5H, m), 7.67-7.78(4H, m), 7.93-8.07(4H, m). IR (CHCl₃): 3276, 3018, 2946, 2868, 1726, 1595, 1435, 1341, 1162, 1095/cm. [α]_D=−1.5° (CHCl₃, c=1.01, 25.0° C.). mp. 133-139° C.

[0127] No.1a-11

[0128] CD₃OD 300 MHz; 1.05-1.98(14H, m), 2.13-2.22(3H, m), 2.97(1H, m), 5.09-5.22(2H, m), 7.85-7.92(4H, m), 7.95-8.05(4H, m). IR (KBr): 3385, 3261, 3069, 3003, 2954, 2872, 1708, 1596, 1428, 1413, 1378, 1343, 1326, 1236, 1186, 1160, 1096/cm. mp. 144-146° C.

[0129] No.1a-12

[0130] CDCl₃300 MHz; 0.96-1.96(14H, m), 2.22-2.27(3H, m), 3.03(1H, m), 3.66(3H, s), 3.87(3H, s), 4.86(1H, d, J=6.9 Hz), 5.18-5.24(2H, m), 6.99-7.02(2H, m), 7.55-7.66(2H, m), 7.66-7.69(2H, m), 7.89-7.92(2H, m). IR (CHCl₃): 3374, 3270, 3016, 2948, 2870, 1726, 1608, 1518, 1487, 1458, 1437, 1248, 1157, 1037. [α]_D=+4.2° (CHCl₃, c=1.01, 24° C.). mp. 85-87° C.

[0131] No.1a-13

[0132] CDCl₃300 MHz; 0.97-1.99(14H, m), 2.18(1H, m), 2.30(2H, t, J=7.2 Hz), 3.04(1H, m), 3.86(3H, s), 5.18(1H, d, J=5.7 Hz), 5.23-5.26(2H, m), 6.99-7.02(₂H, m), 7.55-7.58(2H, m), 7.66-7.68(2H, m), 7.89-7.92(2H, m). IR (CHCl₃): 3380, 3260, 3020, 2948, 2868, 1708, 1608, 1519, 1487, 1458, 1306, 1293, 1248, 1156/cm. [α]_D=+18.3° (CHCl₃, c=1.00, 25.5° C.).

[0133] No.1a-14

[0134] CDCl₃300 MHz; 0.98-2.00(14H, m), 2.20(1H, m), 2.25(2H, t, J=7.2 Hz), 3.02(1H, m), 3.67(3H, B), 4.8(1H, d, J=6.3 Hz), 5.19-5.25(2H, m), 7.13(1H, dd, J=4.8, 3.6 Hz), 7.39(1H, d, J=4.8 Hz), 7.40(1H, d, J=3.6 Hz), 7.71-7.74(2H, m), 7.86-7.89(2H, m). IR (CHCl₃): 3374, 3270, 3018, 2946, 2868, 1727, 1593, 1434, 1322/cm. [α]_D=+5.6° (CHCl₃, c=1.01, 24° C.). mp. 69-71° C.

[0135] No.1a-15

[0136] CDCl₃300 MHz; 0.95-2.00(14H, m), 2.17(1H, m), 2.32(2H, t, J=7.2 Hz), 3.03(1H, m), 5.20(1H, d, J=6.9 Hz), 5.24-5.28(2H, m), 7.13(1H, dd, J=4.8, 3.3 Hz), 7.38(1H, d, J=4.8 Hz), 7.43(1H, d, J=3.3 Hz), 7.73(2H, d, J=8.4 Hz), 7.87(2H, d, J=8.4 Hz). IR (CHCl₃): 3260, 3022, 2948, 2868, 1709, 1593, 1404, 1321, 1154/cm. [α]_D=+20.8° (CHCl₃, c=1.07, 23° C.). mp. 71-73° C.

[0137] No.1a-16

[0138] CDCl₃300 MHz; 0.98-2.00(14H, m), 2.27(2H, t, J=7.5 Hz), 2.28(1H, m), 3.13(1H, m), 3.66(3H, s), 4.90(1H, d, J=6.9 Hz), 5.25-5.29(2H, m), 7.40-7.65(6H, m), 7.76(1H, d, J=8.4 Hz), 7.90-8.02(4H, m). IR (CHCl₃): 3376, 3276, 3018, 2946, 2868, 1726, 1593, 1435, 1394, 1322, 1159/cm. [α]_D=+7.0° (CHCl₃, c=1.07, 24° C.).

[0139] No.1a-17

[0140] CDCl₃300 MHz; 1.02-2.07(14H, m), 2.25(1H, m), 2.34(2H, t, J=6.6 Hz), 3.14(1H, m), 5.28-5.33(3H, m), 7.39-7.57(4H, m), 7.62-7.65(2H, m), 7.76(1H, d, J=8.1 Hz), 7.89-8.00(4H, m). IR (CHCl₃): 3260, 2948, 2868, 1709, 1593, 1394, 1324, 1157/cm. [α]_D=+20.2° (CHCl₃, c=1.02, 24° C.).

[0141] No.1a-18

[0142] CDCl₃300 MHz; 1.05-1.97(14H, m), 2.25(2H, t, J=7.2 Hz), 2.33(1H, m), 3.12(1H, m), 3.67(3H, s), 4.91(1H, d, J=6.6 Hz), 5.24-5.29(2H, m), 7.24(1H, d, J=3.9 Hz), 7.39-7.45(3H, m), 7.56(1H, d, J=3.9 Hz), 7.59-7.62(2H, m). IR (CHCl₃): 3372, 3272, 3018, 2946, 2868, 1727, 1433, 1331, 1152/cm. [α]_D=−5.7° (CHCl₃, c=1.01, 23° C.).

[0143] No.1a-19

[0144] CDCl₃300 MHz; 1.05-2.05(14H, m), 2.28-2.33(3H, m), 3.13(1H, m), 5.18(1H, d, J=6.3 Hz), 5.27-5.31(2H, m), 7.24(1H, d, J=4.2 Hz), 7.39-7.42(3H, m), 7.56(1H, d, J=4.2 Hz), 7.58-7.62(2H, m). IR (CHCl₃): 3372, 3254, 3018, 2948, 2868, 1707, 1431, 1328, 1151/cm. [α]_D=+4.5° (CHCl₃, c=1.01, 21.5° C.).

[0145] No.1a-20

[0146] CDCl₃300 MHz; 1.05-2.00(14H, m), 2.26(2H, t, J=7.5 Hz), 2.33(1H, m), 3.11(1H, m), 3.68(3H, s), 4.92(1H, d, J=6.0 Hz), 5.27(2H, m), 7.05(1H, m), 7.10(1H, d, J=3.6 Hz), 7.25(1H, m), 7.32(1H, m), 7.49(1H, d, J=3.6 Hz). IR (CHCl₃): 3372, 3272, 3018, 2946, 2686, 1727, 1438, 1417, 1333, 1151/cm. [α]_D=−9.2° (CHCl₃, c=1.01, 25° C.).

[0147] No.1a-21

[0148] CDCl₃300 MHz; 1.02-2.01(14H, m), 2.28-2.34(3H, m), 3.13(1H, m), 5.12(1H, d, J=6.9 Hz), 5.28-5.32(2H, m), 7.06(1H, m), 7.10(1H, d, J=3.9 Hz), 7.25(1H, m), 7.32(1H, m), 7.50(1H, d, J=3.9 Hz). IR (CHCl₃): 3350, 3250, 2948, 1709, 1440, 1420, 1330, 1151. [α]_D=+2.5° (CHCl₃, c=1.00, 25° C.).

[0149] No.1a-22

[0150] CDCl₃300 MHz; 0.96-2.05(14H, m), 2.25(1H, m), 2.35(2H, t, J=7.0 Hz), 3.11(1H, m), 5.20-5.34(2H, m), 5.41(1H, d, J=6.6 Hz), 7.31-7.49(5H, m), 7.62(1H, d, J=7.8 Hz), 8.11(1H, d, J=1.8 and 7.8 Hz), 8.35(1H, d, J=1.8 Hz). IR (CHCl₃): 3384, 3271, 3025, 2958, 1708, 1608, 1559, 1537, 1357, 1168/cm. [α]_D=+18.3° (CHCl₃, c=0.31, 220° C.).

[0151] No.1a-23

[0152] CDCl₃300 MHz; 0.97-2.07(14H, m), 2.24(1H, m), 2.35(2H, t, J=6.9 Hz), 3.09(1H, m), 3.86(3H, s), 5.24-5.35(2H, m), 5.44(1H, d, J=6.3 Hz), 6.97-7.00(2H, m), 7.26-7.28(2H, m), 7.59(1H, d, J=8.1 Hz), 8.06(1H, d.d, J=2.1 and 8.1 Hz), 8.29(1H, d, J=2.1 Hz). IR (CHCl₃): 3384, 3270, 2959, 1709, 1609, 1535, 1519, 1357, 1302, 1255, 1226, 1169/cm. [α]_D=+17.0° (CHCl₃, c=1.00, 210° C.).

[0153] No.1a-24

[0154] CDCl₃300 MHz; 0.95-2.00(14H, m), 2.20-2.25(1H, m), 2.26(2H, t, J=7.2 Hz), 3.02-3.10(1H, m), 3.66(3H, s), 4.92(H, d, J=6.6 Hz), 5.16-5.31(2H, m), 7.52-7.60(3H, m), 7.94-8.06(6H, m). IR (CHCl₃): 3376, 3020, 2946, 2868, 1726, 1436, 1366, 1298, 1164, 1090, 890/cm. [α]_D=+11.2±0.5° (CHCl₃, c=1.04, 23.5° C.); mp. 101-103° C.

[0155] No.1a-25

[0156] CDCl₃300 MHz; 0.95-2.08(14H, m), 2.15-2.22(1H, m), 2.33(2H, t, J=6.9 Hz), 3.02-3.10(1H, m), 5.21-5.31(2H, m), 5.34(1H, d, J=6.3 Hz), 7.51-7.59(3H, m), 7.92-8.07(6H, m). IR (CHCl₃): 3258, 3022, 2948, 2868, 1707, 1399, 1328, 1298, 1163, 1089, 1051, 892/cm. [α]_D=+29.8±0.7° (CHCl₃, c=1.05, 25° C.); mp. 158-160° C.

[0157] No.1a-26

[0158] Anal. Calcd for C₂₆H₃₀N₃O₄SNa 0.8H₂O: C, 60.29; H, 6.15; N, 8.11; S, 6.19; Na, 4.44; Found: C, 60.15; H, 6.19; N, 8.15; S, 6.03; Na, 4.98. [α]_D=16.6° (CHCl₃, c=1.04, 25.0° C.).

[0159] No.1a-27

[0160] CDCl₃300 MHz; 0.92-1.98(14H, m), 2.20(1H, m), 2.26(2H, t, J=7.5 Hz), 3.03(1H, m), 3.12(6H, s), 3.66(3H, s), 4.87(1H, d, J=6.6 Hz), 5.16-5.32(2H, m), 6.73-6.80(2H, m), 7.88-8.00(6H, m). IR (CHCl₃): 3376, 3020, 2946, 1726, 1601, 1518, 1442, 1419, 1362, 1312, 1163, 1133, 1088/cm. [α]_D=+55.3° (CHCl₃, c=0.53, 24.0° C.). mp. 158-168° C.

[0161] No.1a-28

[0162] CDCl₃+CD₃OD 300 MHz; 0.99-2.14(14H, m), 2.21(1H, m), 2.31(2H, t, J=7.2 Hz), 2.94(1H, m), 3.12(6H, s), 5.22-5.38(2H, m), 6.73-6.81(2H, m), 7.87-8.00(6H, m). IR (KBr): 3434, 3309, 2946, 1708, 1604, 1520, 1442, 1416, 1366, 1312, 1252, 1164, 1155, 1134, 1091/cm. [α]_D=not measurable (colored, insufficient energy); mp. 193-196° C.

[0163] No.1a-29

[0164] CD₃OD 300 MHz; 1.02-1.96(14H, m), 2.10(2H, t, J=7.8 Hz), 2.16(1H, m), 2.98(1H, m), 3.11(6H, s), 5.07-5.27(2H, m), 6.80-6.87(2H, m), 7.84-8.00(6H, m). IR (KBr): 3433, 3087, 3004, 2949, 2871, 1604, 1565, 1520, 1444, 1420, 1864, 1312, 1253, 11638, 1136, 1090/cm. [α]_D=not measurable.

[0165] No.1a-30

[0166] CDCl₃300 MHz; 0.95-1.99(14H, m), 2.22(1H, m), 2.26(2H, t, J=7.2 Hz), 2.35(3H, s), 3.06(1H, m), 3.66(3H, s), 4.95(1H, d, J=6.9 Hz), 5.15-5.30(2H, m), 7.26-7.32(2H, m), 7.97-8.06(6H, m). IR (CHCl₃): 3374, 2996, 2946, 2868, 1763, 1728, 1591, 1495, 1435, 1368, 1299, 1228, 1192, 1163, 1139/cm. [α]_D=+12.9° (CHCl₃, c=1.04, 26.0° C.).

[0167] No.1a-31

[0168] CDCl₃300 MHz; 0.93-2.01(14H, m), 2.19(1H, m), 2.31(2H, t, J=7.2 Hz), 2.35(3H, s), 3.06(1H, m), 5.17-5.32(2H, m), 7.25-7.32(2H, m), 7.96-8.07(6H, m). IR (CHCl₃): 3267, 3028, 2952, 2874, 1759, 1708, 1592, 1495, 1368, 1328, 1299, 1163, 1138, 1088, 1050, 1008/cm. [α]_D=+21.7° (CHCl₃, c=0.51, 22° C.).

[0169] No.1a-32

[0170] CDCl₃300 MHz; 0.93-1.99(14H, m), 2.21(1H, m), 2.27(2H, t, J=7.2 Hz), 3.05(1H, m), 3.67(3H, s), 4.92(1H, d, J=6.6 Hz), 5.15-5.30(2H, m), 6.72(1H, s), 6.96-7.00(2H, m), 7.86-8.04(6H, m). IR (CHCl₃): 3374, 3276, 3018, 2946, 2686, 1725, 1605, 1589, 1502, 1433, 1396, 1330, 1271, 1164, 1135, 1089/cm. [α]_D=+18.6° (CHCl₃, c=1.00, 26.0° C.).

[0171] No.1a-33

[0172] CDCl₃+CD₃OD 300 MHz; 0.98-2.08(14H, m), 2.20(1H, m), 2.28(2H, t, J=7.2 Hz), 2.98(1H, m), 5.18-5.32(2H, m), 6.92-6.99(2H, m), 7.85-8.02(6H, m). IR (KBr): 3385, 3248, 2948, 2876, 1717, 1601, 1505, 1430, 1399, 1296, 1280, 1219, 1165, 1136, 1092/cm. [α]_D=−16.0° (CH₃OH, c=1.08, 26.0° C.). mp. 208-210° C.

[0173] No.1a-34

[0174] mp. 82-83° C. [α]_D=+10.6° (CHCl₃, c=1.01, 23.5° C.).

[0175] No.1a-35

[0176] mp. 80-82° C. [α]_D=−1.8° (CHCl₃, c=1.07, 22.0° C.).

[0177] No.1a-36

[0178] TLC Rf=0.25 (ethyl acetate/n-hexane=1:1 (0.3% acetic acid)).

[0179] No.1a-37

[0180] CDCl₃300 MHz; 0.92-1.96(14H, m), 2.21(1H, m), 2.27(2H, t, J=7.4 Hz), 3.01(1H, m), 3.66(3H, s), 4.71(1H, d, J=6.6 Hz), 5.14-5.29(2H, m), 7.12(1H, d, J=16.2 Hz), 7.24(1H, d, J=16.2 Hz), 7.28-7.42(3H, m), 7.52-7.56(2H, m), 7.62(2H, d, J=8.7 Hz), 7.85(2H, d, J=8.7 Hz). IR (CHCl₃): 3384, 3283, 3023, 2954, 2876, 1730, 1595, 1494, 1317, 1163, 1147/cm. [α]_D=+10.5° (CHCl₃, c=1.01, 24° C.). mp 116-117° C.

[0181] No.1a-38

[0182] CDCl₃300 MHz; 0.92-1.99(14H, m), 2.17(1H, m), 2.32(2H, t, J=7.2 Hz), 3.02(1H, m), 5.23-5.29(3H, m), 7.11(1H, d, J=16.2 Hz), 7.23(1H, d, J=>16.2 Hz), 7.28-7.41(3H, m), 7.52-7.55(2H, m), 7.61(2H, d, J=8.7 Hz), 7.86(2H, d, J=8.7 Hz). IR (CHCl₃): 3516, 3384, 3270, 3022, 3015, 2957, 2876, 2669, 1708, 1595, 1496, 1320, 1157/cm. [α]_D=+27.1° (CHCl₃, c=1.02, 24° C.).

[0183] No.1a-39

[0184] CDCl₃300 MHz; 0.92-1.99+(14H, m), 2.15(1H, m), 2.28(2H, t, J=7.4 Hz), 3.01(1H, m), 3.68(3H, s), 4.96(1H, d, J=6.6 Hz), 5.16-5.32(2H, m), 6.60(1H, d, J=12.0 Hz), 6.74(1H, d, J=12.0 Hz), 7.16-7.23(5H, m), 7.35(2H, d, J=8.4 Hz), 7.72(2H, d, J=8.4 Hz). IR (CHCl₃): 3384, 3283, 3023, 3015, 2954, 2876, 1730, 1595, 1493, 1324, 1163, 1147/cm. [α]_D=+13.7° (CHCl₃, c=1.00, 24° C.).

[0185] No.1a-40

[0186] CDCl₃300 MHz; 0.90-2.16(14H, m), 2.12(1H, m), 2.34(2H, t, J=7.2 Hz), 3.02(1H, m), 5.16(1H, d, J=6.9 Hz), 5.23-5.34(2H, m), 6.60(1H, d, J=12.3 Hz), 6.74(1H, d, J=12.3 Hz), 7.14-7.24(5H, m), 7.35(2H, d, J=8.1 Hz), 7.72(2H, d, J=8.1 Hz). IR (CHCl₃): 3515, 3384, 3269, 3025, 3021, 3014, 2957, 2876, 2668, 1709, 1595, 1322, 1162, 1147/cm. [α]_D=+26.4° (CHCl₃, c=1.00, 24° C.).

[0187] No.1a-41

[0188] CDCl₃300 MHz; 0.98-1.99(14H, m), 2.17(1H, m), 2.32(2H, t, J=7.2 Hz), 3.00(1H, m), 3.84(3H, s), 5.20-5.26(3H, m), 6.90-6.95(2H, m), 6.98(1H, d, J=16.2 Hz), 7.17(1H, d, J=16.2 Hz), 7.46-7.49(2H, m), 7.58(2H, d, J=8.4 Hz), 7.83(2H, d, J=8.4 Hz). IR (CHCl₃): 3258, 3018, 3002, 2950, 1709, 1590, 1509, 1457, 1404, 1302, 1250, 1153/cm. [α]_D=+30.2° (CHCl₃, c=1.00, 23° C.). mp. 99-100° C.

[0189] No.1a-42

[0190] CDCl₃300 MHz; 1.01-1.99(14H, m), 2.28(2H, t, J=7.2 Hz), 2.30(1H, m), 3.10(1H, m), 3.66(3H, s), 5.07(1H, br), 5.25-5.30(2H, m), 6.98-7.04(2H, m), 7.16(1H, d, J=16.2 Hz), 7.28-7.37(3H, m), 7.47-7.50(3H, m). IR (CHCl₃): 3372, 3276, 3020, 2946, 2870, 1727, 1491, 1433, 1331, 1152/cm. [α]_D=−11.5° (CHCl₃, c=1.07, 21.5° C.).

[0191] No.1a-43

[0192] CDCl₃300 MHz; 0.98-2.00(14H, m), 2.11-2.36(3H, m), 3.12(1H, m), 5.10(1H, d, J=6.6 Hz), 5.29-5.32(2H, m), 6.99-7.04(2H, m), 7.23(1H, d, J=21.6 Hz), 7.32-7.49(6H, m). IR (CHCl₃): 3380, 3248, 3020, 2948, 2868, 1709, 1491, 1430, 1329, 1151/cm. [α]_D=+3.4° (CHCl₃, c=1.03, 25° C.).

[0193] No.1a-44

[0194] CDCl₃300 MHz; 1.00-2.00(14H, m), 2.13(1H, m), 2.29(2H, t, J=7.4 Hz), 2.90-3.13(5H, m), 3.68(3H, s), 4.74(1H, d, J=6.6 Hz), 5.15-5.30(2H, m), 7.18-7.29(7H, m), 7.76(2H, d, J=8.1 Hz), IR (CHCl₃): 3384, 3282, 3063, 3028, 3023, 3016, 2953, 2876, 1730, 1599, 1496, 1319, 1157/cm. [α]_D=+2.3° (CHCl₃, c=1.00, 25° C.). mp. 85.0-86.0° C.

[0195] No.1a-45

[0196] CDCl₃300 MHz; 0.90-2.05(14H, m), 2.09(1H, m), 2.35(2H, t, J=6.9 Hz), 2.90-3.13(5H, m), 5.18(1H, d, J=6.6 Hz), 5.24-5.34(2H, m), 7.10-7.27(7H, m), 7.76(2H, d, J=8.4 Hz). IR (CHCl₃): 3510, 3384, 3270, 3087, 3063, 3026, 3018, 3014, 2955, 2876, 2670, 1708, 1599, 1496, 1318, 1157/cm. [α]_D=+8.5° (CHCl₃, c=1.01, 25° C.).

[0197] No.1a-46 [α]_D=+6.8° (CHCl₃, c=1.05, 25° C.). mp. 99-100° C.

[0198] No.1a-47

[0199] CDCl₃300 MHz; 0.97-2.01(14H, m), 2.14(1H, m), 2.36(2H, t, J=7.2 Hz), 3.02(1H, m), 5.23(1H, d, J=5.4 Hz), 5.26-5.30(2H, m), 7.37-7.39(3H, m), 7.54-7.58(2H, m), 7.85-7.88(2H, m). IR (CHCl₃): 3375, 3260, 3022, 2948, 2212, 1707, 1596, 1497, 1396, 1322, 1160/cm. [α]_D=+25.0° (CHCl₃, c=1.02, 24° C.). mp. 117-118° C.

[0200] No.1a-48

[0201] CD₃OD 300 MHz; 1.05-1.93(14H, m), 2.10-2.15(3H, m), 2.96(1H, m), 5.08-5.28(2H, m), 7.38-7.40(3H, m), 7.554-7.56(2H, m), 7.69(1H, d, J=8.4 Hz), 7.87(1H, d, J=8.4 Hz).

[0202] No.1a-49

[0203] CDCl₃300 MHz; 0.96-1.97(14H, m), 2.24(1H, m), 2.31(2H, t, J=6.9 Hz), 3.05(1H, m), 3.69(3H, s), 5.15(1H, d, J=6.6 Hz), 5.25-5.27(2H, m), 7.40-7.43(3H, m), 7.61-7.64(2H, m), 7.85(1H, d, J=8.1 Hz), 8.07(1H, dd, J=8.1, 1.8 Hz), 8.58(1H, d, J=1.8 Hz). IR (CHCl₃): 3374, 3020, 2948, 2870, 2212, 1726, 1606, 1530, 1493, 1437, 1345, 1167/cm. [α]_D=+2.4° (CHCl₃, c=1.03, 25° C.). mp. 77-79° C.

[0204] No.1a-50

[0205] CDCl₃300 MHz; 1.00-2.02(14H, m), 2.20(1H, m), 2.34(2H, t, J=6.6 Hz), 3.08(1H, m), 5.26-5.29(2H, m), 5.41(1H, d, J=6.9 Hz), 7.40-7.43(3H, m), 7.61-7.64(2H, m), 7.84(1H, d, J=8.1 Hz), 8.07(1H, dd, J=8.4, 1.8 Hz), 8.57(1H, dd, J=1.8 Hz). IR (CHCl₃): 3380, 3254, 2952, 2880, 2212, 1707, 1606, 1531, 1493, 1409, 1344, 1166. [α]_D=+23.4° (CHCl₃, c=1.00, 25° C.):

[0206] No.1a-51

[0207] CDCl₃300 MHz; 0.95-1.98(14H, m), 2.23(1H, m), 2.30(2H, t, J=7.2 Hz), 3.00(1H, m), 3.66(3H, s), 4.56(2H, br), 4.70(1H, d, J=6.9 Hz), 5.20-5.29(2H, m), 7.15(1H, dd, J=7.8, 1.8 Hz), 7.23(1H, d, J=1.8 Hz), 7.36-7.39(3H, m), 7.46(1H, d, J=7.8 Hz), 7.53-7.56(2H, m). IR (CHCl₃): 3494, 3386, 3028, 2952, 2874, 1725, 1611, 1559, 1497, 1422, 1317, 1162/cm.

[0208] No.1a-52

[0209] CDCl₃300 MHz; 0.96-2.04(16H, m), 2.20(1H, m), 2.36(2H, t, J=6.9 Hz), 2.99(1H, m), 5.17(1H, d, J=6.3 Hz), 5.28-5.31(2H, m), 7.18(1H, dd, J=9.6, 1.8 Hz), 7.25(1H, m), 7.36-7.39(3H, m), 7.46(1H, d, J=7.8 Hz), 7.52-7.56(2H, m). IR (CHCl₃): 3482, 3378, 3260, 3022, 2948, 2868, 1708, 1612, 1495, 1422, 1317/cm. [α]_D=+15.0° (CHCl₃, c=1.00, 24° C.).

[0210] No.1a-53

[0211] CDCl₃300 MHz; 1.01-2.05(15H, m), 2.31(2H, t, J=7.2 Hz), 3.10(1H, m), 3.67(3H, s), 5.02(1H, br), 5.26-5.33(2H, m), 7.18(1H, d, J=4.2 Hz), 7.36-7.39(3H, m), 7.48(1H, d, J=4.2 Hz), 7.51-7.55(2H, m). IR (CHCl₃): 3372, 3270, 3018, 3004, 2946, 2868, 2202, 1726, 1486, 1433, 1336, 1154/cm. [α]_D=+0.6° (CHCl₃, c=1.11, 25° C.), [α]₄₃₆+17.8° (CHCl₃, c=1.11, 250° C.).

[0212] No.1a-54

[0213] CDCl₃300 MHz; 0.99-2.11(14H, m), 2.27(1H, m), 2.37(2H, t, J=7.5 Hz), 3.13(1H, m), 5.16(1H, d, J=6.6 Hz), 5.31-5.35(2H, m), 7.18(1H, d, J=3.6 Hz), 7.37-7.39(3H, m), 7.50(1H, d, J=3.6 Hz), 7.52-7.55(2H, m). IR (CHCl₃): 3484, 3370, 3246, 2948, 2868, 2202, 1708, 1486, 1429, 1335, 1153/cm. [α]_D=+17.8° (CHCl₃, c=1.00, 24° C.). mp. 95-96° C.

[0214] No.1a-55

[0215] CDCl₃300 MHz; 0.95-1.92(14H, m), 2.15(1H, m), 2.24(2H, t, J=7.5 Hz), 3.00(1H, m), 3.66(3H, s), 5.10-5.30(3H, m), 7.40-7.60(7H, m), 7.70(1H, d, J=7.8 Hz), 8.08(1H, d, J=8.1 Hz). IR (CHCl₃): 3356, 3020, 2948, 2868, 2210, 1727, 1490, 1458, 1437, 1341, 1165/cm. [α]_D=58.4° (CHCl₃, c=1.00, 26° C.). mp. 84-85° C.

[0216] No.1a-56

[0217] CDCl₃300 MHz; 0.95-1.95(14H, m), 2.10(1H, m), 2.27(2H, t, J=6.9 Hz), 3.00(1H, m), 5.17-5.21(2H, m), 5.38(1H, d, J=6.9 Hz), 7.39-7.60(7H, m), 7.70(1H, dd, J=7.8, 1.5 Hz), 8.07(1H, J=6.6, 1.5 Hz). IR (CHCl₃): 3364, 3026, 2952, 2874, 2212, 1707, 1597, 1491, 1458, 1411, 1341, 1164/cm. [α]_D=−43.1° (CHCl₃, c=1.00, 25° C.).

[0218] No.1a-57

[0219] CDCl₃300 MHz; 0.99-1.97(14H, m), 2.23-2.30(3H, m), 3.01(1H, m), 3.67(3H, s), 5.17-5.26(3H, m), 7.36-7.38(3H, m), 7.50-7.56(3H, m), 7.60(1H, m), 7.83(1H, m), 8.05(1H, m). IR (CHCl₃): 3376, 3020, 2946, 2870, 1727, 1598, 1491, 1437, 1412, 1330, 1245, 1163/cm. [α]_D=−12.7° (CHCl₃, c=1.00, 24° C.).

[0220] No.1a-58

[0221] CDCl₃300 MHz; 0.97-1.98(14H, m), 2.20(1H, m), 2.33(2H, t, J=6.9 Hz), 3.02(1H, m), 5.19-5.28(3H, m), 7.36-7.38(3H, m), 7.47-7.55(3H, m), 7.69(1H, m), 7.83(1H, m), 8.04(1H, m). IR (CHCl₃): 3376, 3260, 3022, 3002, 2948, 2868, 2220, 1708, 1598, 1490, 1455, 1412, 1327, 1162/cm. [α]_D=−8.6° (CHCl₃, c=1.01, 24° C.).

[0222] No.1a-59

[0223] CDCl₃300 MHz; 0.95-1.99(24H, m), 2.20(1H, m), 2.28(2H, t, J=7.8 Hz), 2.53(1H, s), 2.96(1H, m), 3.69(3H, s), 4.99(1H, d, J=6.6 Hz), 5.18-5.20(2H, m), 7.53(2H, d, J=8.4 Hz), 7.82(2H, d, J=8.4 Hz). IR (CHCl₃): 3583, 3376, 3002, 2936, 2852, 1725, 1591, 1490, 1437, 1393, 1325, 1160/cm. [α]_D=−8.8° (CHCl₃, c=1.00, 24° C.).

[0224] No.1a-60

[0225] CDCl₃300 MHz; 0.96-2.05(24H, m), 2.22(1H, m), 2.33(2H, m), 2.88(1H, m), 5.22-5.26(2H, m), 5.30(1H, d, J=5.7 Hz), 7.50(2H, d, J=8.7 Hz), 7.80(2H, d, J=8.7 Hz). IR (CHCl₃): 3376, 3260, 3022, 2936, 2852, 1710, 1592, 1491, 1452, 1395, 1325, 1159/cm. [α]_D=−8.9° (CHCl₃, c=1.06, 24° C.), mp. 88-91° C.

[0226] No.1a-61

[0227] CDCl₃300 MHz; 0.95-2.24(23H, m), 2.29(2H, m), 2.99(1H, m), 3.69(3H, s), 4.76(1H, d, J=6.3 Hz), 5.21-5.24(2H, m), 6.28(1H, m), 7.50-7.53(2H, m), 7.77-7.80(2H, m). IR (CHCl₃): 3374, 3270, 3018, 2942, 2868, 2196, 1726, 1589, 1490, 1435, 1324, 1158/cm. [α]_D=+7.7° (CHCl₃, c=1.02, 24° C.), mp. 93-95° C.

[0228] No.1a-62

[0229] CDCl₃300 MHz; 0.96-2.45(23H, m), 2.36(2H, d, J=6.9 Hz), 2.99(1H, m), 5.24(1H, d, J=6.3 Hz), 5.24-5.32(2H, m), 6.28(1H, m), 7.50-7.53(2H, m), 7.78-7.81(2H, m). IR (CHCl₃): 3468, 3374, 3260, 3020, 2942, 2868, 2196, 1598, 1490, 1455, 1398, 1322, 1157/cm. [α]_D=+19.4° (CHCl₃, c=1.03, 24° C.).

[0230] No.1a-63

[0231] CDCl₃300 MHz; 0.93-1.95(25H, m), 2.16(1H, m), 2.29(2H, t, J=7.2 Hz), 2.43(2H, t, J=6.9 Hz), 2.94(1H, m), 3.69(3H, s), 4.95(1H, d, J=6.9 Hz), 5.21-5.24(2H, m), 7.49(2H, d, J=8.7 Hz), 7.79(2H, J=8.7 Hz). IR (CHCl₃): 3376, 3018, 2946, 2866, 2222, 1727, 1592, 1456, 1435, 1325, 1158/cm. [α]_D=+3.7° (CHCl₃, c=1.00, 25° C.).

[0232] No.1a-64

[0233] CDCl₃300 MHz; 0.93-1.97(26H, m), 2.35(2H, t, J=7.2 Hz), 2.43(2H, t, J=7.2 Hz), 3.00(1H, m), 5.08(1H, d, J=6.6 Hz), 5.26-5.27(2H, m), 7.49(2H, d, J=8.7 Hz), 7.78(2H, d, J=8.7 Hz). IR (CHCl₃): 3260, 3020, 2948, 2864, 2222, 1708, 1592, 1489, 1456, 1397, 1324, 1156/cm. [α]_D=+14.4° (CHCl₃, c=1.00, 25° C.) mp. 70-71° C.

[0234] No.1a-65

[0235] CDCl₃300 MHz; 0.95-1.98(14H, m), 2.18(1H, m), 2.30(2H, t, J=7.2 Hz), 3.00(1H, m), 3.67(3H, s), 4.83(1H, d, J=6.9 Hz), 5.22-5.25(2H, m), 5.54(1H, br), 6.82-6.85(2H, m), 7.42-7.45(2H, m), 7.59-7.62(2H, m), 7.82-7.85(2H, m). IR (CHCl₃): 3576, 3374, 3018, 2946, 2868, 2208, 1725, 1607, 1587, 1514, 1435, 1325, 1270, 1162, 1133/cm. [α]_D=+9.1° (CHCl₃, c=1.03, 24° C.), mp. 111-112° C.

[0236] No.1a-66

[0237] CDCl₃300 MHz; 0.97-2.03(14H, m), 2.15(1H, m), 2.35(2H, t, J=7.5 Hz), 3.00(1H, m), 5.17(1H, d, J=6.6 Hz), 5.26-5.30(2H, m), 6.82-6.85(2H, m), 7.42-7.45(2H, m), 7.59-7.62(2H, m), 7.82-7.85(2H, m). IR (CHCl₃): 3260, 2948, 2870, 2208, 1709, 1607, 1587, 1514, 1396, 1325, 1270, 1162, 1133/cm. [α]_D=−21.0° (CHCl₃, c=1.00, 23° C.), mp. 161-162° C.

[0238] No.1a-67

[0239] CDCl₃300 MHz; 0.95-1.98(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.01(1H, m), 3.67(3H, s), 4.82(1H, d, J=6.6 Hz), 5.19-5.27(2H, m), 7.05-7.10(2H, m), 7.51-7.56(2H, m), 7.61-7.64(2H, m), 7.84-7.87(2H, m). IR (CHCl₃): 3374, 3280, 3020, 2946, 2868, 2214, 1727, 1589, 1509, 1435, 1327, 1233, 1161, 1134/cm. [α]_D=+6.7° (CHCl₃, c=1.01, 24° C.), mp. 84-85° C.

[0240] No.1a-68

[0241] CDCl₃300 MHz; 0.96-2.01(14H, m), 2.15(1H, m), 2.34(2H, t, J=6.9 Hz), 3.02(1H, m), 5.23-5.27(3H, m), 7.04-7.10(2H, m), 7.51-7.56(2H, m), 7.61-7.64(2H, m), 7.85-7.88(2H, m). IR (CHCl₃): 3374, 3258, 3020, 2948, 2868, 2214, 1708, 1589, 1509, 1455, 1398, 1322, 1156/cm. [α]_D=+22.6° (CHCl₃, c=1.02, 24° C.), mp. 135-136° C.

[0242] No.1a-69

[0243] CDCl₃300 MHz; 0.95-1.98(14H, m), 2.19(1H, m), 2.29(2H, t, J=7.2 Hz), 2.39(3H, s), 3.01(1H, m), 3.69(3H, s), 4.80(1H, d, J=6.6 Hz), 5.20-5.29(2H, m), 7.18(2H, d, J=8.1 Hz), 7.44(2H, d, J=8.1 Hz), 7.62(2H, d, J=8.4 Hz), 7.84(2H, d, J=8.4 Hz). IR (CHCl₃): 3374, 3022, 2946, 2868, 2210, 1727, 1589, 1511, 1436, 1323, 1161, 1133/cm. [α]_D=+9.2° (CHCl₃, c=1.02, 24° C.). mp. 116-118° C.

[0244] No.1a-70

[0245] CDCl₃300 MHz; 1.15-2.00(14H, m), 2.13(1H, m), 2.33-2.38(5H, m), 3.04(1H, m), 5.14(1H, d, J=6.6 Hz), 5.25-5.30(2H, m), 7.17(2H, d, J=7.8 Hz), 7.44(2H, d, J=7.8 Hz), 7.62(2H, d, J=8.4 Hz), 7.85(2H, d, J=8.4 Hz). IR (CHCl₃): 3380, 3260, 3020, 2948, 2868, 2210, 1708, 1590, 1511, 1396, 1324, 1160, 1133/cm. [α]_D=+24.6° (CHCl₃, c=1.00, 24° C.).

[0246] No.1a-71

[0247] CDCl₃300 MHz; 0.95-1.96(14H, m), 2.19(1H, m), 2.29(2H, t, J=7.2 Hz), 3.00(1H, m), 3.20(1H, s), 3.65(3H, s), 4.81(1H, d, J=6.6 Hz), 5.20-5.27(2H, m), 7.46-7.54(4H, m), 7.62-7.65(2H, m), 7.85-7.88(2H, m). IR (CHCl₃): 3374, 3290, 3018, 3002, 2946, 2868, 2212, 2110, 1726, 1591, 1507, 1435, 1401, 1324, 116/cm. [α]_D=+9.6° (CHCl₃, c=1.01, 24° C.), mp. 136-138° C.,

[0248] No.1a-72

[0249] CDCl₃300 MHz; 0.96-2.01(14H, m), 2.14(1H, m), 2.35(2H, t, J=7.2 Hz), 3.05(1H, m), 3.20(1H, s), 5.16(1H, d, J=7.2 Hz), 5.26-5.29(2H, m), 7.45-7.53(4H, m), 7.63(2H, d, J=8.4 Hz), 7.87(2H, d, J=8.4 Hz). IR (CHCl₃): 3462, 3374, 3290, 3024, 2948, 2868, 2212, 2110, 1708, 1591, 1508, 1455, 1401, 1321, 1274, 1160, 1132/cm. [α]_D=+24.3° (CHCl₃, c=1.03, 24° C.), mp. 96-99° C.

[0250] No.1a-73

[0251] CDCl₃300 MHz; 0.95-1.98(14H, m), 2.19(1H, m), 2.27-2.32(5H, m), 3.01(1H, m), 3.67(3H, s), 4.08(1H, d, J=6.6 Hz), 5.20-5.27(2H, m), 7.12(2H, m), 7.56(2H, m), 7.63(2H, m), 7.84(2H, m). IR (CHCl₃): 3374, 3276, 3018, 2946, 2868, 2214, 1762, 1730, 1589, 1506, 1435, 1368, 1161/cm. [α]_D=+7.8° (CHCl₃, c=1.02, 24c), mp. 102-104° C.

[0252] No.1a-74

[0253] CDCl₃300 MHz; 0.95-2.05(14H, m), 2.15(1H, m), 2.32-2.37(5H, m), 3.02(1H, m), 5.14(1H, d, J=6.6 Hz), 5.26-5.30(2H, m), 7.10-7.13(2H, m), 7.54-7.57(2H, m), 7.62-7.64(2H, m), 7.84-7.87(2H, m). IR (CHCl₃): 3482, 3250, 3022, 2946, 2868, 2214, 1716, 1709, 1589, 1507, 1454, 1396, 1368, 1322, 1195, 1161/cm. [α]_D=+15.0° (CHCl₃, c=1.00, 24° C.), mp. 129-131° C.

[0254] No.1a-75

[0255] CDCl₃300 MHz; 0.95-1.99(14H, m), 2.20(1H, m), 2.30(2H, t, J=7.2 Hz), 3.02(1H, m), 3.67(3H, s), 3.94(3H, s), 4.79(1H, d, J=6.6 Hz), 5.19-5.29(2H, m), 7.60-7.63(2H, m), 7.65-7.67(2H, m), 7.86-7.89(2H, m), 8.04-8.06(2H, m). IR (CHCl₃): 3378, 3018, 2946, 2880, 1720, 1604, 1435, 1307, 1276, 1161, 1106/cm. [α]_D=+7.3° (CHCl₃, c=1.01, 25° C.), mp. 132-133° C.

[0256] No.1a-76

[0257] CDCl₃+CD₃OD 300 MHz; 1.04-2.05(14H, m), 2.19(1H, m), 2.32(2H, t, J=6.9 Hz), 2.93(1H, m), 5.27-5.31(2H, m), 7.60-7.63(2H, m), 7.65-7.68(2H, m), 7.86-7.89(2H, m), 8.05-8.07(2H, m). IR (CHCl₃): 3402, 3299, 2955, 2876, 2665, 2549, 1455, 1422, 1313, 1281, 1164/cm. [α]_D=−21.1° (CH₃OH, c=1.03, 23° C.), mp. 227-229(dec.)

[0258] No.1a-77

[0259] CDCl₃300 MHz; 0.96-1.99(14H, m), 2.20(1H, m), 2.30(2H, t, J=7.2 Hz), 3.02(1H, m), 3.68(3H, s), 4.88(1H, d, J=6.3 Hz), 5.19-5.29(2H, m), 7.67-7.72(4H, m), 7.89-7.91(2H, m), 8.2.24-87(2H, m). IR (CHCl₃): 3376, 3276, 3020, 2946, 2870, 2214, 1726, 1594, 1519, 1455, 1435, 1389, 1344, 1161/cm. [α]_D=+7.7° (CHCl₃, c=1.02), mp. 87-89° C.

[0260] No.1a-78

[0261] CDCl₃300 MHz; 0.98-2.00(14H, m), 2.18(1H, m), 2.34(2H, t, J=7.2 Hz), 3.02(1H, m), 5.24-5.28(2H, m), 5.32(1H, d, J=5.7 Hz), 7.67-7.72(4H, m), 7.89-7.92(2H, m), 8.23-8.26(2H, m). IR (CHCl₃): 3374, 3260, 2948, 2214, 1708, 1595, 1344, 1160/cm. [α]_D=+23.3° (CHCl₃, c=1.00), mp. 102-103° C.

[0262] No.1a-79

[0263] CDCl₃300 MHz; 0.93-2.02(14H, m), 2.13(1H, m), 2.36(2H, t, J=7.1 Hz), 3.05(1H, m), 3.84(3H, s), 5.18(1H, br), 5.27-5.31(2H, m), 6.88-6.91(2H, m), 7.48-7.50(2H, m), 7.60-7.63(2H, m), 7.83-7.85(2H, m). IR (CHCl₃): 3380, 3252, 3020, 2950, 2868, 2208, 1708, 1589, 1511, 1457, 1396, 1321, 1286, 1160/cm. [α]_D=+26.7° (CHCl₃, c=1.00). mp. 75-77° C.

[0264] No.1a-80

[0265] CDCl₃300 MHz; 0.96-1.99(14H, m), 2.21(1H, m), 2.30(2H, t, J=7.8 Hz), 3.02(1H, m), 3.68(3H, s), 4.80(1H, d, J=6.6 Hz), 5.19-5.28(2H, m), 7.51-7.77(5H, m), 7.87-7.90(2H, m), 8.13(1H, m). IR (CHCl₃): 3374, 3270, 3018, 2946, 2868, 2216, 1726, 1607, 1567, 1527, 1495, 1456, 1436, 1344, 1296, 1161/cm. [α]_D=+7.4° (CHCl₃, c=1.00, 22° C.), mp. 68-70° C.

[0266] No.1a-81

[0267] CDCl₃300 MHz; 0.97-2.01(14H, m), 2.16(1H, m), 2.34(2H, t, J=7.2 Hz), 3.01(1H, m), 5.22-5.28(3H, m), 7.51(1H, m), 7.65(1H, m)7.70-7.76(3H, m), 7.88-7.91(2H, m), 8.12(1H, dd, J=6.9 Hz, 1.5 Hz). IR (CHCl₃): 3480, 3382, 3262, 3026, 2952, 2872, 2218, 1708, 1607, 1567, 1526, 1396, 1343, 1225, 1160/cm. [α]_D=+22.0° (CHCl₃, c=1.00), mp. 92-94° C.

[0268] No.1a-82

[0269] CDCl₃300 MHz; 0.95-1.98(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.01(1H, m), 3.67(3H, s), 4.30(2H, br), 4.79(1H, d, J=6.9 Hz), 5.20-5.29(2H, m), 6.71-6.76(2H, m), 7.18(1H, m), 7.37(1H, dd, J=7.8, 1.2 Hz), 7.61-7.65(2H, m), 7.83-7.87(2H, m). IR (CHCl₃): 3376, 3020, 2946, 2868, 2202, 1725, 1613, 1589, 1484, 1454, 1315, 1253, 1161/cm. [α]_D=+8.9° (CHCl₃, c=1.00, 22° C.). mp. 68-70° C.

[0270] No.1a-83

[0271] CDCl₃300 MHz; 0.97-1.99(14H, m), 2.17(1H, m), 2.33(2H, t, J=6.9 Hz), 2.99(1H, m), 5.20-5.28(2H, m), 5.37(1H, d, J=6.9 Hz), 6.45(2H, br), 6.71-6.76(2H, m), 7.19(1H, dd, J=7.8, 6.6 Hz), 7.37(1H, m), 7.62(2H, d, J=8.4 Hz), 7.85(2H, d, J=8.4 Hz). IR (CHCl₃): 3478, 3378, 3260, 3022, 2950, 2868, 2204, 1708, 1613, 1589, 1484, 1454, 1396, 1316, 1160/cm. [α]_D=+17.1° (CHCl₃, c=1.01).

[0272] No.1a-84

[0273] CDCl₃300 MHz; 1.00-2.08(14H, m), 2.21(1H, m), 2.37(2H, t, J=6.9 Hz), 3.06(1H, m), 3.86(3H, s), 5.29-5.33(2H, m), 5.45(1H, d, J=6.6 Hz), 6.91-6.94(2H, m), 7.56-7.59(2H, m), 7.81(1H, d.t, J=8.1 Hz), 8.04(1H, d.d, J=8.1&1.8 Hz), 8.57(1H, d, J=2.1 Hz). IR (CHCl₃): 3492, 3254, 3028, 2954, 2202, 1708, 1597, 1512, 1344, 1291, 1250/cm. [α]_D=+27.4° (CHCl₃, c=0.53, 23° C.).

[0274] No.1a-85

[0275] CDCl₃300 MHz; 0.96-2.06(14H, m), 2.20(1H, m), 2.35(2H, t, J=6.9 Hz), 2.99(1H, m), 3.84(3H, s), 5.22-5.31(3H, m), 6.89(2H, d, J=8.7 Hz), 7.19(1H, brs), 7.29(1H, brs), 7.45-7.50(3H, m). IR (CHCl₃): 3478, 3378, 3020, 2950, 2868, 2202, 1708, 1606, 1511, 1421, 1311, 1287, 1248, 1155/cm. [α]_D=+17.1° (CHCl₃, c=1.00, 23° C.).

[0276] No.1a-86

[0277] CDCl₃300 MHz; 1.03-2.05(14H, m), 2.21(1H, m), 2.37(2H, t, J=6.9 Hz), 3.04(1H, m), 5.29-5.33(2H, m), 5.57(1H, d, J=6.3 Hz), 6.84-6.87(2H, m), 7.50-7.53(2H, m), 7.79(1H, d, J=8.1 Hz), 8.03(1H, d, d, J=1.5and 8.1 Hz), 8.57(1H, d, J=1.5 Hz). IR (CHCl₃): 3250, 3024, 2950, 2868, 2200, 1707, 1515, 1344, 1271, 1166, 1143/cm. [α]_D=+21.2° (CHCl₃, c=0.26, 22° C.).

[0278] No.1a-87

[0279] CD₃OD 300 MHz; 1.04-2.00(14H, m), 2.18(1H, m), 2.26(2H, t, J=5.4 Hz), 2.93(1H, m), 5.19-5.24(2H, m), 6.77-6.80(2H, m), 7.05(1H, d.d, J=2.1 and 8.1 Hz), 7.22(1H, d, J=2.1 Hz), 7.38-7.42(3H, m). IR (CHCl₃): 3377, 2952, 2873, 2204, 1705, 1607, 1515, 1425, 1312, 1267, 1222, 1153/cm. [α]_D=−15.6° (CH₃OH, c=1.02, 22° C.).

[0280] No.1a-88

[0281] CDCl₃300 MHz; 0.90-1.96(14H, m), 2.22-2.31(3H, m), 2.95(1H, m), 3.65(3H, s), 4.87(1H, d, J=6.6 Hz), 5.13-5.28(2H, m), 7.46-7.6 2(3H, m), 7.82-7.89(4H, m), 7.90-7.96(2H, m), 8.42(1H, brs). IR (CHCl₃): 3376, 3016, 2946, 2868, 1720, 1677, 1592, 1514, 1498, 1429, 1376, 1314, 1241, 1156, 1094/cm. [α]_D=−10.7° (CHCl₃, c=1.04, 22.0° C.) mp. 134-136° C.

[0282] No.1a-89

[0283] CDCl₃+CD₃OD 300 MHz; 0.96-2.08(14H, m), 2.23(1H, m), 2.28(2H, t, J=7.2 Hz), 2.89(1H, m), 5.20-5.32(2H, m), 7.46-7.62(3H, m), 7.82-7.97(6H, m). IR (KBr): 3272, 3007, 2952, 2874, 1708, 1660, 1592, 1527, 1498, 1433, 1400, 1317, 1260, 1152, 1094/cm. [α]_D=−24.4° (CH₃OH, c=1.02, 25.0° C.).

[0284] No.1a-90

[0285] CDCl₃300 MHz; 0.89-1.96(14H, m), 2.23-2.33(3H, m), 2.92(1H, m), 3.67(3H, s), 4.85(1H, d, J=6.3 Hz), 5.10-5.25(2H, m), 7.81-7.90(4H, m), 8.10-8.18(2H, m), 8.31-8.40(2H, m), 8.77(1H, s). IR (CHCl₃): 3372, 3018, 2946, 2868, 1718, 1685, 1592, 1527, 1436, 1397, 1346, 1318, 1256, 1154, 1099/cm. [α]_D=−16.1° (CHCl₃, c=1.00, 23.0° C.).

[0286] No.1a-91

[0287] CDCl₃+CD₃OD 300 MHz; 0.94-2.02(14H, m), 2.18-2.36(3H, m), 2.87(1H, m), 5.15-5.30(2H, m), 7.82-7.92(4H, m), 8.09-8.16(2H, m), 8.30-8.37(2H, m). IR (KBr): 3284, 3112, 3006, 2952, 2874, 1707, 1593, 1528, 1498, 1399, 1348, 1320, 1259, 1153, 1093/cm. [α]_D=−26.3° (CH₃OH, c=1.01, 22° C.).

[0288] No.1a-92

[0289] CDCl₃300 MHz; 0.93-1.95(14H, m), 2.22-2.31(3H, m), 2.98(1H, m), 3.68(3H, s), 5.07(1H, d, J=6.9 Hz), 5.10-5.24(2H, m), 7.18(1H, m), 7.35-7.43(2H, m), 7.70(2H, d, J=7.8 Hz), 7.88-8.05(4H, m), 8.50(1H, brs). IR (CHCl₃): 3382, 3008, 2952, 1720, 1675, 1599, 1525, 1499, 1438, 1321, 1253, 1161, 1087/cm. [α]_D=−16.6° (CHCl₃, c=1.03, 24.0° C.) mp. 100-101° C.

[0290] No.1a-93

[0291] CDCl₃+CD₃OD 300 MHz; 0.96-2.00(14H, m), 2.18-2.35(3H, m), 2.90(1H, m), 5.15-5.30(2H, m), 7.18(1H, m), 7.33-7.42(2H, m), 7.65-7.74(2H, m), 7.90-8.08(4H, m). IR (KBr): 3347, 3194, 3011, 2955, 2875, 1706, 1650, 1602, 1544, 1499, 1443, 1325, 1265, 1165, 1091/cm. [α]_D=−19.4° (CH₃OH, c=1.00, 24.0° C.) mp. 158-159° C.

[0292] No.1a-94

[0293] CD₃OD 300 MHz; 1.05-2.00(14H, m), 2.14(1H, m), 2.23(2H, t, J=7.2 Hz), 2.98(1H, m), 3.80(3H, s), 5.13-5.27(2H, m), 6.88-6.98(2H, m), 7.54-7.64(2H, m), 7.94-8.12(4H, m). IR (KBr): 3370, 3006, 2953, 1708, 1649, 1604, 1541, 1512, 1460, 1441, 1414, 1328, 1302, 1248, 1162, 1107, 1090, 1032/cm. [α]_D=−19.1° (CH₃OH, c=1.01, 24° C.).

[0294] No.1a-95

[0295] CD₃OD 300 MHz; 1.04-2.02(14H, m), 2.14(1H, m), 2.23(2H, t, J=7.2 Hz), 2.93-3.02(7H, m), 5.13-5.27(2H, m), 6.82-6.92(2H, m), 7.51-7.59(2H, m), 7.95-8.02(2H, m), 8.04-8.11(2H, m). IR (KBr): 3370, 3006, 2953, 1708, 1649, 1604, 1541, 1512, 1460, 1441, 1414, 1328, 1302, 1248, 1162, 1107, 1090, 1032/cm. [α]_D=−17.6° (CH₃OH, c=1.01, 24° C.).

[0296] No.1a-96

[0297] CD₃OD 300 MHz; 1.05-2.02(14H, m), 2.14(1H, m), 2.23(2H, t, J=7.2 Hz), 2.98(1H, m), 5.13-5.27(2H, m), 6.75-6.84(2H, m), 7.43-7.52(2H, m), 7.94-8.12(4H, m). IR (KBr): 3339, 3197, 2953, 2875, 1707, 1644, 1606, 1541, 1514, 1446, 1325, 1293, 1259, 1240, 1225, 1161, 109/cm. [α]_D=−18.7° (CH₃OH, c=1.00, 24° C.). mp. 193-196° C.

[0298] No.1a-97

[0299] d₈-DMSO 300 MHz; 1.05-2.08(15H, m), 2.15(2H, t, J=7.5 Hz), 2.89(1H, m), 5.18-5.28(2H, m), 6.78-7.12(3H, m), 7.73(1H, d.d, J=1.4and 7.8 Hz), 7.91-7.95(3H, m), 8.14(2H, d, J=8.4 Hz), 9.71(1H, s). IR (KBr): 3407, 3191, 2953, 1711, 1646, 1614, 1603, 1537, 1457, 1326, 1162, 1151/cm. [α]_D=−20.7° (CH₃OH, c=1.01, 21° C.).

[0300] No.1a-98

[0301] CDCl₃300 MHz; 0.93-2.00(14H, m), 2.21(1H, m), 2.31(2H, t, J=7.2 Hz), 2.93(1H, m), 3.84(3H, s), 3.85(6H, s), 5.15-5.30(2H, m), 5.45(1H, d, J=6.3 Hz), 7.04(2H, s), 7.78-7.86(2H, m), 7.90-7.98(2H, m), 8.58(1H, s). IR (CHCl₃): 3264, 3008, 2954, 2874, 1707, 1670, 1607, 1537, 1506, 1451, 1421, 1308, 1158, 1129, 1088/cm. [α]_D=7.2° (CHCl₃, c=1.01, 23.5° C.). mp. 147-149° C.

[0302] No.1a-99

[0303] CD₃OD 300 MHz; 1.04-1.98(14H, m), 2.21(1H, m), 2.10(2H, t, J=7.2 Hz), 2.95(1H, m), 3.76(3H, s), 3.86(6H, s), 5.07-5.24(2H, m), 7.19(2H, s), 7.99(2H, d, J=8.7 Hz), 8.13(1H, d, J=8.7 Hz). IR (KBr): 3354, 3002, 2950, 2874, 1656, 1607, 1570, 1508, 1452, 1413, 1314, 1233, 1185, 1157, 1127, 1092/cm. [α]_D=−20.3° (CH₃OH, c=1.00, 23.5° C.).

[0304] No.1a-100

[0305] CDCl₃300 MHz; 1.14-1.97(14H, m), 2.19(1H, m), 2.28(2H, t, J=7.4 Hz), 3.04(1H, m), 3.69(3H, s), 5.03(1H, d, J=6.9 Hz), 5.15-5.29(2H, m), 7.65(2H, d, J=8.4 Hz), 7.87(1H, s), 7.98(2H, d, J=8.4 Hz). IR (CHCl₃): 3386, 3271, 3025, 3015, 2955, 2877, 1755, 1712, 1608, 1331, 1162/cm. [α]_D=−29.4° (CH₃OH, c=1.01, 25° C.).

[0306] No.1a-101

[0307] d₆-DMSO 1.00-2.20(17H, m), 2.84(1H, m), 5.00-5.20(2H, m), 7.78(2H, d, J=8.2 Hz), 7.84(1H, s), 7.89-7.95(3H, m). IR (KBr): 3269, 3065, 3008, 2952, 2874, 2763, 1746, 1707, 1607, 1322, 1157/cm. [α]_D=−26.2° (CH₃OH, c=1.01, 25° C.).

[0308] No.1a-102

[0309] CD₃OD 1.00-2.25(17H, m), 2.92(1H, s), 3.64(3H, s), 5.07-5.21(2H, m), 7.53(1H, s), 7.77(2H, d, J=8.6 Hz), 7.90(2H, d, J=8.6). IR (KBr): 3430, 3277, 3006, 2952, 2873, 1720, 1687, 1620, 1571, 1438, 1312, 1156/cm. [α]_D=−27.3° (CH₃OH, c=0.51, 26° C.), mp 230-232° C.

[0310] No.1a-103

[0311] CDCl₃300 MHz; 0.94-1.96(14H, m), 2.19(1H, m), 2.28(2H, t, J=7.2 Hz), 3.04(1H, m), 3.69(3H, s), 5.11(1H, d, J=6.6 Hz), 5.15-5.28(2H, m), 7.60(2H, d, J=8.4 Hz), 7.67(1H, s), 7.98(2H, d, J=8.4 Hz). IR (CHCl₃): 3381, 3021, 2955, 2876, 1735, 1605, 1437, 1411, 1325, 1231, 1177/cm. [α]_D=+8.6° (CHCl₃, c=1.00, 23° C.).

[0312] No.1a-104

[0313] CDCl₃300 MHz; 0.94-1.96(14H, m), 2.21(1H, m), 2.31(2H, t, J=6.8 Hz), 2.99(1H, m), 5.18-5.28(2H, m), 5.45(1H, d, J=6.6 Hz), 7.61(2H, d, J=8.7 Hz), 7.67(1H, s), 7.99(2H, d, J=8.7 Hz). IR (CHCl₃): 3382, 3222, 3028, 3019, 2957, 2876, 1736, 1709, 1604, 1412, 1322, 1301, 1286, 1179, 1162/cm. [α]_D=+10.4° (CHCl₃, c=1.00, 23° C.).

[0314] No.1a-105

[0315] CDCl₃300 MHz; 0.92-1.98(14H, m), 2.17(1H, m), 2.26(2H, d, J=7.5 Hz), 3.01(1H, m), 3.69(3H, s), 4.01(3H, s), 4.84(1H, d, J=6.3 Hz), 5.14-5.30(2H, m), 7.71(2H, d, J=8.7 Hz), 7.87(2H, d, J=8.7 Hz), 8.09(1H, s). IR (CHCl₃): 3385, 3284, 3025, 3015, 2954, 2877, 2821, 1730, 1598, 1459, 1438, 1403, 1341, 1160, 1052/cm. [α]_D=+3.6° (CHCl₃, c=1.00, 26° C.).

[0316] No.1a-106

[0317] CDCl₃300 MHz; 0.92-2.08(14H, m), 2.14(1H, m), 2.34(2H, d, J=7.2 Hz), 3.02(1H, m), 4.01(3H, s), 5.19(1H, d, J=6.9 Hz), 5.23-5.32(2H, m), 7.71(2H, d, J=8.4 Hz), 7.88(2H, d, J=8.4 Hz), 8.09(1H, s). IR (CHCl₃): 3510, 3384, 3268, 3028, 3021, 3014, 2957, 2877, 2821, 2667, 2821, 2666, 1707, 1598, 1459, 1404, 1341, 1324, 1160, 1052/cm. [α]_D=+11.8° (CHCl₃, c=1.01, 25° C.). mp 95-96° C.

[0318] No.1a-107

[0319] CDCl₃300 MHz; 0.92-1.97(14H, m), 1.34(3H, t, J=7.2 Hz), 2.18(1H, m), 2.28(2H, d, J=7.4 Hz), 3.01(1H, m), 3.68(3H, s), 4.26(2H, q, J=7.2 Hz), 4.86(1H, d, J=6.6 Hz), 5.15-5.29(2H, m), 7.71(2H, d, J=8.7 Hz), 7.87(2H, d, J=8.7 Hz), 8.09(1H, s). IR (CHCl₃): 3385, 3282, 3025, 3026, 3015, 2954, 2877, 1729, 1599, 1480, 1458, 1438, 1403, 1338, 1161/cm. [α]_D=+4.4° (CHCl₃, c=1.00, 25° C.).

[0320] No.1a-108

[0321] CDCl₃300 MHz; 0.90-2.04(14H, m), 1.34(3H, t, J=7.2 Hz), 2.14(1H, m), 2.34(2H, d, J=7.1 Hz), 3.01(1H, m), 4.27(2H, q, J=7.2 Hz), 5.20(1H, d, J=6.6 Hz), 5.21-5.35(2H, m), 7.71(2H, d, J=8.4 Hz), 7.88(2H, d, J=8.4 Hz), 8.10(1H, s). IR (CHCl₃): 3514, 3384, 3270, 3025, 3015, 3015, 2957, 2877, 1708, 1599, 1458, 1403, 1324, 1324, 1160, 1050/cm. [α]_D=+12.7° (CHCl₃, c=1.00, 25° C.).

[0322] No.1a-109

[0323] [α]_D=+8.5° (CHCl₃, c=1.00, 25° C.). mp 109.0-111.0° C.

[0324] No.1a-110

[0325] CDCl₃: CD₃OD (95:5) 0.92-2.06(14H, m), 2.20(1H, m), 2.80(2H, d, J=7.2 Hz), 2.99(1H, m), 5.22-5.33(2H, m), 7.54-7.66(3H, m), 8.07(2H, d, J=9.0 Hz), 8.12-8.20(2H, m), 8.29(2H, d, J=9.0 Hz). IR (Nujol): 3270, 2956, 2924, 2854, 1716, 1548, 1485, 1319, 1167/cm. [α]_D=+17.0° (CHCl₃, c=1.00, 25° C.). mp. 166.5-168° C.

[0326] No.1a-111

[0327] [α]_D=+2.6° (CHCl₃, c=1.00, 24° C.).mp 120.0-121.0° C.

[0328] No.1a-112

[0329] CDCl₃300 MHz; 0.96-2.04(14H, m), 2.19(1H, m), 2.33(2H, d, J=7.1 Hz), 3.07(1H, m), 5.28-5.31(2H, m), 5.33(1H, d, J=6.6 Hz), 7.54-7.63(3H, m), 8.05(2H, d, J=8.4 Hz), 8.18-8.23(2H, m), 8.41(2H, d, J=8.4 Hz). IR (CHCl₃): 3384, 3269, 3025, 3015, 2957, 2877, 1708, 1598, 1496, 1457, 1417, 1326, 1164/cm. [α]_D=+12.2° (CHCl₃, c=1.00, 24° C.). mp. 163-164° C.

[0330] No.1a-113

[0331] [α]_D=+22.1° (CHCl₃, c=1.05, 25° C.). mp. 90-92° C.

[0332] No.1a-14

[0333] [α]_D=+2.2° (CHCl₃, c=1.02;25° C.).

[0334] No.1a-115

[0335] CDCl₃300 MHz; 0.90-1.98(14H, m), 2.15-2.22(1H, m), 2.27(2H, t, J=7.2 Hz), 2.95-3.04(1H, m), 3.68(3H, s), 4.04(2H, s), 4.85(1H, d, J=6.6 Hz), 5.10-5.27(2H, m), 7.12-7.34(7H, m), 7.76-7.82(2H, m). IR (CHCl₃): 3384, 3026, 2952, 1727, 1595, 1493, 1436, 1318, 1155, 1091, 890/cm. [α]_D=0°; [α]₄₃₆=+4.9±0.4° (CHCl₃, c=1.05, 23° C.).

[0336] No.1a-116

[0337] CDCl₃300 MHz; 0.90-2.10(14H, m), 2.10-2.18(1H, m), 2.32(2H, t, J=7.2 Hz), 2.96-3.04(1H, m), 4.04(2H, s), 5.14(1H, d, J=6.6 Hz), 5.16-5.28(2H, m), 7.12-7.34(7H, m), 7.76-7.82(2H, m). IR (CHCl₃): 3260, 3020, 2950, 1709, 1407, 1318, 1154, 1091, 892/cm. [α]_D=+9±0.5° (CHCl₃, c=1.04, 23° C.).

[0338] No.1a-117

[0339] CD₃OD 300 MHz; 0.96-2.18(17H, m), 2.89-2.92(1H, m), 4.05(2H, s), 4.95-5.22(2H, m), 7.15-7.42(7H, m), 7.75-7.81(2H, m). IR (KBr): 3429, 3279, 2951, 2872, 1563, 1494, 1453, 1408, 1313, 1155, 1093, 1057/cm. [α]_D=−16.3±0.5° (CH₃OH, c=1.06, 25° C.).

[0340] No.1a-118

[0341] CDCl₃300 MHz; 0.98-1.70(15H, m), 1.80-2.00(5H, m), 2.20-2.40(3H, m), 2.98(1H, m), 4.06(2H, s), 4.72(1H, d, J=6.3 Hz), 5.00-5.23(3H, m), 7.16(2H, d, J=8.4 Hz), 7.26-7.33(5H, m), 7.79(2H, d, J=8.1 Hz). IR (CHCl₃): 3376, 3020, 2948, 2868, 1716, 1596, 1492, 1453, 1407, 1318, 1155, 1105/cm. [α]_D=+2.4° (CHCl₃, c=1.08, 24°C.).

[0342] No.1a-119

[0343] CDCl₃300 MHz; 0.90-2.02(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.00(1H, m), 3.68(3H, s), 4.86(1H, d, J=6.9 Hz), 5.13-5.34(2H, m), 7.00-7.09(4H, m), 7.22(1H, m), 7.37-7.45(2H, m), 7.79-7.86(2H, m). IR (CHCl₃): 3376, 3018, 2946, 2868, 1727, 1582, 1486, 1321, 1243, 1151, 1093/cm. [α]_D=+4.5° (CHCl₃, c=1.05, 23.5° C.).

[0344] No.1a-120

[0345] CD₃OD 300 MHz; 1.00-2.00(14H, m), 2.13(2H, t, J=7.5 Hz), 2.16(1H, m), 2.91(1H, m), 5.05-5.33(2H, m), 7.04-7.11(4H, m), 7.18-7.25(1H, m), 7.38-7.48(2H, m), 7.80-7.87(2H, m). IR (KBr): 3430, 3278, 3006, 2952, 2873, 1583, 1487, 1410, 1322, 1298, 1245, 1152, 1095/cm. [α]_D=−8.8° (CH₃OH, c=1.05, 25.0° C.).

[0346] No.1a-121

[0347] CDCl₃300 MHz; 0.90-2.10(14H, m), 2.15(1H, m), 2.35(2H, t, J=7.2 Hz), 3.01(1H, m), 5.20(1H, d, J=6.9 Hz), 5.22-5.35(2H, m), 7.00-7.09(4H, m), 7.18-7.25(1H, m), 7.37-7.45(2H, m), 7.79-7.86(2H, m). IR (CHCl₃): 3260, 3020, 2948, 2868, 1708, 1582, 1486, 1409, 1321, 1296, 1243, 1151, 1093/cm. [α]_D=+13.1° (CHCl₃, c=1.04, 24.0° C.).

[0348] No.1a-122

[0349] CDCl₃300 MHz; 0.90-2.00(14H, m), 2.23(1H, m), 2.28(2H, t, J=7.5 Hz), 2.96(1H, m), 3.67(3H, s), 4.69(1H, d, J=6.6 Hz), 5.15-5.32(2H, m), 6.22(1H, s), 6.98-7.40(5H, m), 7.30-7.38(2H, m), 7.68-7.74(2H, m). IR (CHCl₃): 3416, 3370, 3018, 2946, 2868, 1725, 1587, 1508, 1437, 1400, 1320, 1149, 1094/cm. [α]_D=+6.2° (CHCl₃, c=1.04, 25.0° C.).

[0350] No.1a-123

[0351] CDCl₃300 MHz; 0.90-2.04(14H, m), 2.18(1H, m), 2.33(2H, t, J=7.2 Hz), 2.96(1H, m), 5.04-5.35(3H, m), 6.98-7.12(3H, m), 7.12-7.20(2H, m), 7.28-7.38(2H, m), 7.66-7.74(2H, m). IR (CHCl₃): 3424, 3270, 3028, 2952, 2872, 1708, 1587, 1508, 1445, 1399, 1320, 1148, 1092/cm. [α]_D=+20.9° (CHCl₃, c=1.06, 23.0° C.).

[0352] No.1a-124

[0353] CDCl₃300 MHz; 0.90-2.00(14H, m), 2.18(1H, m), 2.28(2H, t, J=7.2 Hz), 3.00(1H, m), 3.14(3H, s), 3.68(3H, s), 4.56(2H, s), 4.84(1H, d, J=6.3 Hz), 5.10-5.29(2H, m), 7.16-7.26(4H, m), 7.26-7.34(2H, m), 7.78-7.84(2H, m). IR (CHCl₃): 3384, 3028, 2952, 2874, 1727, 1598, 1501, 1435, 1410, 1370, 1329, 1172, 1148, 1091/cm. [α]_D=+2.7° (CHCl₃, c=1.09, 23.0° C.).

[0354] No.1a-125

[0355] CDCl₃300 MHz; 0.90-2.00(14H, m), 2.18(1H, m), 2.28(2H, t, J=7.2 Hz), 2.29(3H, s), 3.00(1H, m), 3.68(3H, s), 4.04(2H, s), 4.80(1H, d, J=6.6 Hz), 5.11-5.29(2H, m), 6.99-7.06(2H, m), 7.12-7.19(2H, m), 7.31(2H, d, J=8.1 Hz), 7.79(2H, d, J=8.1 Hz). IR (CHCl₃): 3382, 3280, 3024, 2950, 2874, 1730, 1596, 1504, 1435, 1407, 1367, 1318, 1196, 1155, 1091/cm. [α]_D=+2.9° (CHCl₃, c=1.06, 23.0° C.).

[0356] No.1a-126

[0357] CDCl₃300 MHz; 0.90-2.02(14H, m), 2.14(1H, m), 2.29(3H, s), 2.32(2H, t, J=7.2 Hz), 3.01(1H, m), 4.03(2H, s), 5.10(1H, d, J=6.6 Hz), 5.15-5.30(2H, m), 6.98-7.06(2H, m), 7.11-7.18(2H, m), 7.30(2H, d, J=8.1 Hz), 7.79(2H, d, J=8.1 Hz). IR (CHCl₃): 3374, 3260, 3020, 2948, 2868, 1749, 1708, 1596, 1504, 1407, 1369, 1317, 1195, 1155, 1091/cm. [α]_D=+10.0° (CHCl₃, c=1.09, 23.0° C.).

[0358] No.1a-127

[0359] CDCl₃300 MHz; 0.87-1.95(14H, m), 2.18-2.32(3H, m), 2.95(1H, m), 3.69(3H, s), 3.96(2H, s), 4.79(1H, d, J=6.6 Hz), 4.97-5.17(2H, m), 5.54(1H, s), 6.75-6.82(2H, m), 6.97-7.05(2H, m), 7.25-7.33(2H, m), 7.75-7.81(2H, m). IR (CHCl₃): 3382, 3026, 2950, 2874, 1722, 1595, 1511, 1436, 1407, 1317, 1257, 1154, 1090/cm. [α]_D=−2.1° (CHCl₃, c=1.00, 21.5° C.).

[0360] No.1a-128

[0361] CDCl₃300 MHz; 0.85-2.02(14H, m), 2.18(1H, m), 2.31(2H, t, J=7.2 Hz), 2.96(1H, m), 3.95(2H, s), 5.05-5.27(3H, m), 6.73-6.82(2H, m), 6.96-7.04(2H, m), 7.25-7.32(2H, m), 7.74-7.81(2H, m). IR (CHCl₃): 3262, 3020, 2948, 2868, 1708, 1596, 1511, 1407, 1315, 1242, 1154, 1091/cm. [α]_D=+4.8° (CHCl₃, c=1.04, 22° C.).

[0362] No.1a-129

[0363] CDCl₃300 MHz; 0.89-1.98(14H, m), 2.18(1H, m), 2.27(2H, t, J=7.2 Hz), 2.99(1H, m), 3.68(3H, s), 3.79(3H, s), 3.98(2H, s), 4.81(1H, d, J=6.6 Hz), 5.10-5.27(2H, m), 6.81-6.87(2H, m), 7.03-7.10(2H, m), 7.25-7.32(2H, m), 7.75-7.82(2H, m). IR (CHCl₃): 3382, 3276, 3006, 2950, 2874, 1726, 1609, 1509, 1457, 1436, 1407, 1315, 1244, 1154, 1091, 1033/cm. [α]_D=+19.3° (CHCl₃, c=1.05, 23° C.).

[0364] No.1a-130

[0365] CDCl₃300 MHz; 0.90-2.00(14H, m) 2.20(1H, m), 2.30(2H, t, J=7.2 Hz), 2.98(1H, m), 3.69(3H, s), 4.81(1H, d, J=6.6 Hz), 5.12-5.32(2H, m), 5.46(1H, brs), 6.84-7.01(6H, m), 7.76-7.83(2H, m); IR (CHCl₃): 3380, 3284, 3024, 2952, 2874, 1724, 1588, 1504, 1488, 1436, 1321, 1296, 1149, 1091/cm. [α]_D=+28.9° (CHCl₃, c=1.01, 23° C.).

[0366] No.1a-131

[0367] CDCl₃300 MHz; 0.92-2.10(14H, m), 2.18(1H, m), 2.34(2H, t, J=6.9 Hz), 2.96(1H, m), 5.18-5.35(3H, m), 6.84-7.01(6H, m), 7.75-7.83(2H, m). IR (CHCl₃): 3270, 3028, 2952, 2874, 1708, 1589, 1505, 1489, 1456, 1322, 1297, 1238, 1148, 1091/cm. [α]_D=+7.7° (CHCl₃, c=1.09, 24° C.).

[0368] No.1a-132

[0369] CDCl₃300 MHz; 0.91-2.02(14H, m), 2.19(1H, m), 2.29(2H, t, J=7.2 Hz), 2.99(1H, m), 3.68(3H, s), 3.83(3H, s), 4.82(1H, d, J=6.6 Hz), 5.14-5.33(2H, m), 6.90-7.04(6H, m), 7.76-7.83(2H, m). IR (CHCl₃): 3384, 3006, 2952, 2874, 1727, 1589, 1502, 1488, 1459, 1438, 1321, 1295, 1231, 1150, 1092, 1033/cm. [α]_D=+3.1° (CHCl₃, c=1.01, 23° C.).

[0370] No.1a-133

[0371] TLC Rf=0.21 (ethyl acetate/n-hexane=1:1 (0.3% acetic acid)).

[0372] No.1a-134

[0373] CDCl₃300 MHz; 5 0.97-2.10(14H, m), 2.20(1H, m), 2.36(2H, t, J=6.9 Hz), 3.04(1H, m), 5.22-5.33(2H, m), 5.41(1H, d, J=6.6 Hz), 7.02(1H, d, J=9.0 Hz), 7.09-7.13(2H, m), 7.26-7.32(1H, m), 7.43-7.49(2H, m), 7.93(1H, d.d, J=2.4and 9.0 Hz), 8.46(1H, d, J=2.4 Hz). IR (CHCl₃): 3384, 3270, 3020, 2958, 1709, 1610, 1587, 1537, 1479, 1352, 1271, 1252, 1167/cm. [α]_D=+20.9° (CHCl₃, c=0.51, 22° C.).

[0374] No.1a-135

[0375] CDCl₃300 MHz; 0.96-2.02(14H, m), 2.21(1H, m), 2.29(2H, t, J=7.2 Hz), 3.07(1H, m), 3.68(3H, s), 5.04(1H, d, J=6.9 Hz), 5.16-5.33(2H, m), 7.48-7.55(2H, m), 7.64(1H, m), 7.76-7.82(2H, m), 7.88-7.94(2H, m), 7.98-8.04(2H, m). IR (CHCl₃): 3384, 3282, 3026, 2952, 2874, 1727, 1663, 1596, 1446, 1396, 1316, 1274, 1163, 1090/cm. [α]_D=+3.1° (CHCl₃, c=1.03, 22.0° C.).

[0376] No.1a-136

[0377] CDCl₃300 MHz; 0.95-2.05(14H, m), 2.19(1H, m), 2.34(2H, t, J=7.2 Hz), 3.08(1H, m), 5.10-5.40(2H, m), 5.35(1H, d, J=6.8 Hz), 7.45-7.58(2H, m), 7.64(1H, m), 7.74-7.84(2H, m), 7.84-7.95(2H, m), 7.95-8.06(2H, m). IR (CHCl₃): 3260, 3018, 2950, 2870, 1708, 1662, 1595, 1446, 1395, 1316, 1274, 1162, 1090/cm. [α]_D=+12.9° (CHCl₃, c=1.05, 21.5° C.).

[0378] No.1a-137

[0379] CDCl₃300 MHz; 0.97-2.04(14H, m), 2.27(1H, m), 2.31(2H, t, J=7.2 Hz), 3.07(1H, m), 3.70(3H, s), 5.15-5.30(3H, m), 7.48-7.68(5H, m), 7.96-8.02(2H, m). IR (CHCl₃): 3382, 3030, 2952, 2878, 1725, 1446, 1329, 1154, 1098/cm. [α]_D=−12.1° (CHCl₃, c=1.03, 22.0° C.).

[0380] No.1a-138

[0381] CDCl₃300 MHz; 0.95-2.04(14H, m), 2.25(1H, m), 2.35(2H, t, J=7.2 Hz), 3.08(1H, m), 5.15-5.34(2H, m), 5.41(1H, d, J=6.6 Hz), 7.48-7.68(5H, m), 7.98-8.03(2H, m). IR (CHCl₃): 3370, 3242, 3022, 2950, 2870, 1707, 1445, 1408, 1329, 1154, 1099/cm. [α]_D=−0.6° (CHCl₃, c=1.06, 21.5° C.) [α]₃₆₅+30.7° (CHCl₃, c=1.06, 21.50° C.).

[0382] No.1a-139

[0383] CDCl₃300 MHz; 0.92-2.19(14H, m), 2.27-2.34(3H, m), 3.26(1H, m), 3.65(3H, s), 4.28(2H, s), 4.37(1H, d, J=7.4 Hz), 5.34-5.50(2H, m), 7.37-7.62(9H, m). IR (CHCl₃): 3389, 3294, 3028, 3015, 2954, 2877, 1730, 1600, 1488, 1325, 1151, 1129/cm. [α]_D=−24.8° (CHCl₃, c=1.01, 24° C.).

[0384] No.1a-140

[0385] CDCl₃300 MHz; 0.92-2.22(15H, m), 2.34(2H, t, J=7.1 Hz), 3.24(1H, m), 4.29(2H, s), 4.81(1H, d, J=7.4 Hz), 5.32-5.52(2H, m), 7.36-7.62(9H, m). IR (CHCl₃): 3510, 3388, 3251, 3031, 3015, 2956, 2877, 2668, 1708, 1601, 1488, 1318, 1151, 1129/cm. [α]_D=−24.6° (CHCl₃, c=1.02, 25° C.).

[0386] No.1a-141

[0387] CDCl₃300 MHz; 0.92-2.19(15H, m), 2.32(2H, t, J=7.2 Hz), 3.26(1H, m), 3.65(3H, s), 4.31(2H, s), 4.48(1H, d, J=7.4 Hz), 5.33-5.49(2H, m), 7.42-7.80(8H, m). IR (CHCl₃): 3388, 3285, 3018, 2955, 2877, 2225, 1730, 1597, 1479, 1320, 1152, 1129/cm. [α]_D=−20.1° (CHCl₃, c=0.96, 25° C.).

[0388] No.1a-142

[0389] CDCl₃300 MHz; 0.92-2.22(15H, m), 2.35(2H, t, J=6.8 Hz), 3.25(1H, m), 4.32(2H, s), 4.86(1H, d, J=7.4 Hz), 5.33-5.53(2H, m), 7.43-7.80(8H, m). IR (CHCl₃): 3512, 3388, 3258, 3031, 3023, 3014, 2956 2877, 2225, 1708, 1597, 1479, 1319, 1151, 1128/cm. [α]_D=−19.3° (CHCl₃, c=1.09, 23° C.).

[0390] No.1a-143

[0391] CDCl₃300 MHz; 1.00-1.93(14H, m), 2.17(1H, m), 2.27(2H, t, J=7.2 Hz), 3.07(1H, m), 5.17-5.22(2H, m), 5.36(1H, d, J=6.9 Hz), 7.77(1H, d, J=9.0 Hz), 8.11-8.17(2H, m), 8.36(1H, d.d, J=2.1 and 9.0 Hz), 8.51(1H, d, J=1.8 Hz), 8.65(1H, d, J=2.1 Hz). IR (CHCl₃): 3382, 3266, 3026, 2954, 2874, 1708, 1632, 1585, 1528, 1458, 1419, 1345, 1153/cm. [α]_D=+7.6° (CHCl₃, c=1.04, 22° C.).

[0392] No.1a-144

[0393] CDCl₃300 MHz; 0.95-1.90(14H, m), 2.17(1H, m), 2.25(2H, t, J=7.5 Hz), 3.02(1H, m), 5.09(1H, d, J=6.6 Hz), 6.15-5.21(2H, m), 6.72(1H, d, J=8.4 Hz), 6.85(1H, s), 7.54(1H, d, J=8.4 Hz), 7.72(1H, d, J=9.0 Hz), 7.83(1H, d.d, J=1.8and 9.0 Hz), 8.32(1H, d, J=1.8 Hz). IR (CHCl₃): 3380, 3260, 3022, 2948, 2868, 2352, 1709, 1636, 1460, 1425, 1313, 1291, 1265, 1148, 1130/cm. [α]_D=+12.9° (CHCl₃, c=1.02, 22.50° C.).

[0394] No.1a-145

[0395] CDCl₃300 MHz; 0.97-1.90(14H, m), 2.15(1H, m), 2.27(2H, t, J=6.9 Hz), 3.02(1H, m), 3.08(6H, s), 5.12(1H, d, J=6.3 Hz), 5.19-5.25(2H, m), 6.78-6.84(2H, m), 7.53(1H, d, J=8.7 Hz), 7.76-7.83(2H, m), 8.30(1H, d, J=1.8 Hz). IR (CHCl₃): 3272, 3030, 2950, 2874, 1708, 1635, 1601, 1511, 1457, 1425, 1357, 1328, 1151, 1124/cm. [α]_D=+6.3° (CHCl₃, c=1.04, 23° C.).

[0396] No.1a-146

[0397] CDCl₃300 MHz; 0.95-2.00(14H, m), 2.16(1H, m), 2.29(2H, t, J=7.2 Hz), 3.05(1H, m), 4.10(3H, s), 5.13-5.28(2H, m), 5.38(1H, d, J=6.9 Hz), 7.67-7.74(2H, m), 8.08(1H, d.d, J=1.8 and 9.0 Hz), 8.11(1H, s), 8.61(1H, d, J=1.8 Hz). IR (CHCl₃): 3260, 3020, 2948, 2868, 1708, 1639, 1606, 1528, 1470, 1455, 1424, 1349, 1311, 1238, 1174, 1149, 1120, 1079, 1060, 1022/cm. [α]_D=+7.8° (CHCl₃, c=1.00, 23° C.).

[0398] No.1a-147

[0399] CDCl₃300 MHz; 0.92-1.92(14H, m), 2.17(1H, m), 2.25(2H, t, J=7.2 Hz), 3.01(1H, m), 3.97(3H, s), 5.10-5.27(5H, m), 6.92(1H, s), 7.29(1H, s), 7.52(1H, d, J=8.7 Hz), 7.82(1H, d.d, J=2.1 and 8.7 Hz), 8.33(1H, d, J=2.1 Hz). IR (CHCl₃): 3380, 3264, 3002, 2950, 2868, 1708, 1634, 1476, 1452, 1426, 1317, 1264, 1218, 1169, 1147, 1115, 1068, 1031/cm. [α]_D=+5.6° (CHCl₃, c=1.02, 23° C.).

[0400] No.1a-148

[0401] CDCl₃300 MHz; 0.90-1.98(14H, m), 2.15(1H, m), 2.28(2H, t, J=6.9 Hz), 2.91(6H, s), 3.03(1H, m), 4.01(3H, s), 5.15-5.26(3H, m), 7.18(1H, s), 7.38(1H, s), 7.59(1H, d, J=8.7 Hz), 7.87(1H, d.d, J=2.1 and 8.7 Hz), 8.40(1H, d, J=2.1 Hz). IR (CHCl₃): 3384, 3266, 2956, 1709, 1632, 1602, 1495, 1473, 1458, 1430, 1317, 1231, 1148, 1121/cm. [α]_D=+11.2° (CHCl₃, c=1.01, 23° C.).

[0402] No.1a-149

[0403] CDCl₃300 MHz; 0.99-1.90(14H, m), 2.17(1H, m), 2.28(2H, t, J=7.2 Hz), 3.00(1H, m), 5.13-5.19(2H, m), 5.43(1H, d, J=6.0 Hz), 7.02(1H, d.d, J=2.4 and 9.0 Hz), 7.38-7.41(2H, m), 7.58(1H, d, J=8.7 Hz), 7.96(1H, d.d, J=1.8 and 8.7 Hz), 8.45(1H, d, J=1.8 Hz). IR (CHCl₃): 3270, 3020, 2948, 2868, 1709, 1601, 1478, 1448, 1419, 1315, 1147, 1120/cm. [α]_D=−11.4° (CHCl₃, c=1.01, 23° C.).

[0404] No.1a-150

[0405] CDCl₃300 MHz; 0.97-1.88(14H, m), 2.12-2.31(3H, m), 2.38(3H, s), 3.01(1H, m), 5.14-5.19(2H, m), 5.36(1H, d, J=6.6 Hz), 7.24(1H, d.d, J=2.4 and 9.0 Hz), 7.59(1H, d, J=6.3 Hz), 7.66(1H, d, J=8.7 Hz), 7.72(1H, d, J=2.4 Hz), 8.01(1H, d.d, J=1.8 and 8.7 Hz), 8.49(1H, d, J=1.8 Hz). IR (CHCl₃): 3470, 3374, 3260, 3018, 2950, 2868, 1709, 1474, 1444, 1412, 1370, 1319, 1266, 1162, 1145, 1118/cm. [α]_D=+4.9° (CHCl₃, c=1.00, 24° C.).

[0406] No.1a-151

[0407] CDCl₃300 MHz; 0.97-1.89(14H, m), 2.17(1H, m), 2.25(2H, t, J=7.2 Hz), 3.03(1H, m), 3.92(3H, s), 5.15-5.20(2H, m), 5.32(1H, d, J=6.6 Hz), 7.11(1H, d.d, J=2.4 and 9.3 Hz), 7.45(1H, d, J=2.4 Hz), 7.50(1H, d, J=9.3 Hz), 7.62(1H, d, J=8.7H), 7.97(1H, d.d, J=2.1 and 8.7 Hz), 8.50(1H, d, J=2.1 Hz). IR (CHCl₃): 3260, 3018, 2948, 1708, 1483, 1454, 1432, 1314, 1287, 1268, 1188, 1169, 1147/cm. [α]_D=+4.9° (CHCl₃, c=1.01, 23.5° C.).

[0408] No.1a-152

[0409] CDCl₃300 MHz; 0.98-2.04(14H, m), 2.15(1H, m), 2.30(2H, t, J=6.6 Hz), 3.04(1H, m), 5.17-5.29(3H, m), 7.41(1H, d.d, J=1.5 and 8.1 Hz), 7.64-7.68(2H, m), 7.92(1H, d, J=8.4 Hz), 8.00(1H, d.d, J=1.8 and 8.4 Hz), 8.49(1H, d, J=1.8 Hz). IR (CHCl₃): 3266, 3028, 2952, 2872, 1707, 1629, 1591, 1456, 1416, 1318, 1275, 1150/cm. [α]_D=+3.2° (CHCl₃, c=1.04, 23° C.).

[0410] No.1a-153

[0411] CDCl₃300 MHz; 0.97-1.88(14H, m), 2.16(1H, m), 2.26(2H, t, J=7.2 Hz), 3.03(1H, m), 4.64-4.65(2H, m), 5.16-5.50(5H, m), 6.13(1H, m), 7.14(1H, d.d, J=2.7 and 9.0 Hz), 7.46-7.52(2H, m), 7.63(1H, d, J=8.7 Hz), 7.97(1H, d.d, J=1.8 and 8.7 Hz), 8.49(1H, d, J=1.8 Hz). IR (CHCl₃): 3374, 3260, 3020, 2948, 2868, 1708, 1599, 1478, 1446, 1414, 1314, 1284, 1268, 1184, 1148, 1120/cm. [α]_D=+5.3° (CHCl₃, c==1.00, 23° C.).

[0412] No.1a-154

[0413] CDCl₃300 MHz; 0.99-2.00(15H, m), 2.26(2H, t, J=7.2 Hz), 3.03(1H, m), 4.07(3H, s), 5.23-5.27(2H, m), 5.36(1H, d, J=7.2 Hz), 7.20(1H, s), 7.36-7.48(2H, m), 7.55-7.58(1H, m), 7.91-7.93(1H, m), 8.52(1H, s). IR (CHCl₃): 3362, 3257, 3020, 2948, 2868, 1708, 1637, 1602, 1579, 1488, 1457, 1437, 1413, 1345, 1318, 1301, 1276, 1182, 1104/cm. [α]_D=+19.4° (CHCl₃, c=1.01, 25° C.). mp. 88-90° C.

[0414] No.1a-155

[0415] CDCl₃300 MHz; 0.92-2.02(14H, m), 2.15(1H, m), 2.31(2H, t, J=7.2 Hz), 3.01(1H, m), 4.10(2H, s), 5.10(1H, d, J=6.6 Hz), 5.18-5.35(2H, m), 7.04-7.26(5H, m), 7.67-7.76(2H, m). IR (CHCl₃): 3266, 3028, 2952, 2952, 2872, 1708, 1599, 1574, 1478, 1457, 1418, 1301, 1258, 1147, 1124, 1101, 1080/cm. [α]₃₆₅+33.4° (CHCl₃, c=1.00, 23° C.).

[0416] No.1a-156

[0417] CDCl₃300 MHz; 0.91-2.21(15H, m), 2.33(2H, t, J=6.9 Hz), 3.01(1H, m), 5.11(1H, d, J=6.6 Hz), 5.27-5.35(2H, m), 6.85-6.96(5H, m), 7.35(1H, d, J=2.1 Hz), 7.42(1H, d.d, J=2.1 and 8.7 Hz). IR (CHCl₃): 3384, 3263, 2957, 1708, 1587, 1489, 1462, 1416, 1290, 1222, 1151, 1123/cm. [α]_D=+6.4° (CHCl₃, c=1.00, 23° C.).

[0418] No.1a-157

[0419] CDCl₃300 MHz; 0.97-1.91(14H, m), 2.18(1H, m), 2.26(2H, t, J=6.9 Hz), 3.04(1H, m), 5.18-5.26(3H, m), 7.52-7.56(2H, m), 7.88-8.00(3H, m), 8.25(1H, m), 8.69(1H, m). IR (CHCl₃): 3382, 3268, 2952, 2874, 1707, 1457, 1425, 1409, 1318, 1152/cm. [α]_D=+4.4° (CHCl₃, c=1.02, 22° C.).

[0420] No.1a-158

[0421] CDCl₃300 MHz; 1.02-1.97(14H, ml), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.06(1H, m), 5.19-5.24(2H, m), 5.58(1H, d, J=6.6 Hz), 7.62(1H, m), 7.72(1H, m), 7.86-7.91(2H, m), 7.96(1H, d, J=7.8 Hz), 8.04(1H, d.d, J=1.5 and 8.1 Hz), 8.34(1H, d, J=1.2 Hz). IR (CHCl₃): 3490, 3260, 3020, 2950, 2870, 1707, 1456, 1399, 1312, 1165/cm. [α]_D=−8.3° (CHCl₃, c=1.00, 23° C.).

[0422] No.1a-159

[0423] CDCl₃300 MHz; 0.92-1.88(14H, m), 2.13(1H, m), 2.24(2H, m), 3.02(1H, m), 3.90(3H, s), 5.12-5.26(3H, m), 7.29-7.58(4H, m), 7.97(1H, d.d, J=1.8 and 7.5 Hz), 8.13(1H, d, J=7.5 Hz), 8.64(1H, d, J=1.8 Hz). IR (CHCl₃): 3382, 3266, 3018, 2956, 1708, 1629, 1594, 1476, 1467, 1325, 1245, 1227, 1158, 1146/cm. [α]_D=+14.6° (CHCl₃, c=1.00, 22° C.).

[0424] No.1a-160

[0425] CDCl₃300 MHz; 0.93-1.88(14H, m), 2.18-2.24(3H, m), 3.00(1H, m), 5.08-5.21(3H, m), 7.28-7.33(1H, m), 7.47-7.51(3H, m), 7.90(1H, d.d, J=1.5 and 7.8 Hz), 8.10(1H, d, J=7.8 Hz), 8.63-8.64(2H, m). IR (CHCl₃): 3465, 3380, 3275, 3020, 2957, 2876, 1708, 1627, 1604, 1495, 1473, 1457, 1328, 1240, 1222, 1156, 1149/cm. [α]_D=+8.2° (CHCl₃, c=1.01, 22° C.).

[0426] No.1a-161

[0427] CDCl₃300 MHz; 0.98-1.88(14H, m), 2.17(1H, m), 2.24(2H, t, J=7.2 Hz), 3.05(1H, m), 5.16-5.20(2H, m), 5.35(1H, d, J=6.6 Hz), 7.40(1H, m), 7.55(1H, m), 7.63(1H, d, J=8.1 Hz), 7.89(1H, d.d, J=1.5 and 8.1 Hz), 8.01(1H, m), 8.06(1H, d, J=8.1 Hz), 8.12(1H, d, J=1.5 Hz). IR (CHCl₃): 3478, 3266, 3028, 2952, 2874, 1708, 1454, 1417, 1323, 1196, 1148/cm. [α]_D=+21.9° (CHCl₃, c=1.01, 23° C.).

[0428] No.1a-162

[0429] CDCl₃300 MHz; 0.96-1.98(14H, m), 2.02(1H, m), 2.25(2H, t, J=7.2 Hz), 3.05(1H, m), 4.10(3H, s), 5.14-5.25(2H, m), 5.41(1H, d, J=7.2 Hz), 7.35-7.42(1H, m), 7.51-7.64(3H, m), 7.94-8.00(1H, m), 8.16(1H, s). IR (CHCl₃): 3368, 3274, 3028, 2952, 2874, 1708, 1633, 1583, 1465, 1452, 1438, 1413, 1315, 1151, 1103, 1053, 1024/cm. [α]_D=+15.1° (CHCl₃, c=1.01, 23° C.). mp. 108-110° C.

[0430] No.1a-163

[0431] d₆-DMSO 300 MHz; 0.97-1.84(14H, m), 1.92(1H, m), 2.04(2H, t, J=7.5 Hz), 2.90(1H, m), 5.08-5.23(2H, m), 7.32(1H, s), 7.38-7.61(2H, m), 7.62(1H, s) 7.68-7.71(1H, m), 7.92(1H, s), 8.14-8.17(1H, m), 10.7(1H, s), 11.9(1H, s). IR (KBr): 3350, 3295, 2952, 2874, 1707, 1636, 1601, 1466, 1431, 1389, 1315, 1251, 1174, 1146, 1106/cm. [α]_D=−25.3° (CH₃OH, c=1.01, 25° C.). mp. 159-162° C.

[0432] No.1a-164

[0433] CDCl₃300 MHz; 0.98-1.96(17H, m), 2.05(1H, m), 2.25(2H, t, J=7.2 Hz), 3.07(1H, m), 4.32(2H, q, J=7.2 Hz), 5.19-5.23(2H, m), 5.31(1H, d, J=7.8 Hz), 7.38(1H, m), 7.41-7.62(3H, m), 7.95(1H, m), 8.15(1H, s). IR (CHCl₃): 3360, 30 18, 2946, 2870, 1709, 1633, 1457, 1445, 1425, 1394, 1314, 1176, 1152, 1105/cm. [α]_D=+12.7° (CHCl₃, c=1.02, 25° C.). mp. 108-109° C.

[0434] No.1a-165

[0435] CDCl₃300 MHz; 0.95-1.98(15H, m), 2.26(2H, t, J=7.5 Hz), 3.04(1H, m), 4.15(3H, s), 5.20-5.26(2H, m), 5.34(1H, d, J=6.9 Hz), 7.41-7.47(1H, m), 7.65-7.68(2H, m), 7.89-7.92(1H, m), 8.32(1H, s). IR (CHCl₃): 3366, 3087, 3022, 2957, 1708, 1632, 1538, 1463, 1408, 1364, 1346, 1308, 1227, 1212, 1205, 1167/cm. [α]_D=+19.6° (CHCl₃, c=1.01, 25° C.).

[0436] No.1a-166

[0437] CDCl₃300 MHz; 0.97-2.02(15H, m), 2.27(2H, t, J=6.9 Hz), 3.07(1H, m), 4.14(3H, s), 5.21-5.27(2H, m), 5.47(1H, d, J=6.9 Hz), 7.64(1H, s), 7.72(1H, d.d, J=0.6 and 9.0 Hz), 8.25(1H, s), 8.47(1H, d.d, J=2.4 and 9.0 Hz), 8.94(1H, d.d, J=0.6 and 2.4 Hz). IR (CHCl₃): 3373, 2957, 1708, 1639, 1587, 1528, 1467, 1428, 1415, 1345, 1221, 1184, 1155/cm. [α]_D=+14.4° (CHCl₃, c=0.60, 256° C.).

[0438] No.1a-167

[0439] CDCl₃300 MHz; 0.92-2.00(14H, m), 2.15(1H, m), 2.27(2H, t, J=7.2 Hz), 3.04(1H, m), 3.97(2H, s), 5.15-5.30(3H, m), 7.35-7.47(2H, m), 7.55-7.63(1H, m), 7.80-7.96(3H, m), 8.05(1H, d, J=0.3 Hz). IR (CHCl₃): 3260, 3020, 2948, 2868, 1707, 1451, 1413, 1319, 1172, 1144, 1101, 1071/cm. [α]_D=+18.2° (CHCl₃, c=1.04, 220° C.).

[0440] No.1a-168

[0441] CDCl₃300 MHz; 0.90-1.88(14H, m), 2.16(1H, m), 2.25(2H, t, J=6.9 Hz), 3.00(1H, m), 5.00-5.19(2H, m), 5.35(1H, d, J=6.6 Hz), 7.25-7.30(1H, m), 7.48-7.50(2H, m), 7.73(1H, d.d, J=1.5 and 8.1 Hz), 8.08-8.14(3H, m), 8.93(1H, s). IR (CHCl₃): 3466, 3380, 3276, 3016, 2957, 1708, 1630, 1495, 1458, 1324, 1241, 1150/cm. [α]_D=+18.0° (CHCl₃, c=1.00, 22° C.).

[0442] No.1a-169

[0443] CDCl₃300 MHz; 0.87-1.86(14H, m), 2.15(1H, m), 2.25(2H, t, J=6.9 Hz), 2.98(1H, m), 3.89(3H, s), 5.00-5.22(2H, m), 5.27(1H, d, J=6.9 Hz), 6.88(1H, d.d, J=2.1 and 8.4 Hz), 6.94(1H, d, J=2.1 Hz), 7.69(1H, d.d, J=1.5 and 7.8 Hz), 7.92-8.01(3H, m), 8.83(1H, s). IR (CHCl₃): 3465, 3378, 3276, 3022, 2957, 1708, 1630, 1609, 1569, 1459, 1433, 1314, 1281, 1229, 1151/cm. [α]_D=+19.3° (CHCl₃, c=1.01, 21° C.).

[0444] No.1a-170

[0445] CDCl₃300 MHz; 0.88-2.25(17H, m), 3.04(1H, m), 3.84(3H, s), 3.95(3H, s), 5.06-5.26(3H, m), 6.87-6.93(2H, m), 7.69(1H, d.d, J=1.6 and 8.2 Hz), 7.93-9.05(3H, m). IR (CHCl₃): 3026, 2957, 1708, 1630, 1601, 1460, 1331, 1243, 1224, 1152/cm. [α]_D=+17.2° (CHCl₃, c=1.00, 22° C.).

[0446] No.1a-171

[0447] CDCl₃300 MHz; 0.95-2.00(14H, m), 2.16-2.32(3H, m), 2.66(3H, s), 3.14(1H, m), 3.68(3H, s), 5.09(1H, d, J=6.8 Hz), 5.10-5.28(2H, m), 7.45(1H, d.d., J=1.8&8.6 Hz), 7.75-7.84(2H, m). IR (CHCl₃): 3374, 3018, 2946, 2868, 1725, 1585, 1513, 1436, 1340, 1278, 1153, 1112/cm. [α]_D=−14.7° (CHCl₃, c=1.07, 25.0° C.).

[0448] No.1a-172

[0449] CDCl₃300 MHz; 0.97-2.02(14H, m), 2.23(1H, m), 2.28(2H, t, J=7.2 Hz), 2.66(3H, s), 3.14(1H, m), 5.12-5.22(2H, m), 5.41(1H, d, J=7.2 Hz), 7.45(1H, d.d., J=2.1&8.7 Hz), 7.76(1H, d, J=8.7 Hz), 7.78(1H, d, J=2.1 Hz). IR (CHCl₃): 3372, 3250, 3022, 2950, 2868, 1707, 1514, 1419, 1336, 1279, 1154, 1112/cm. [α]_D=−4.1° (CHCl₃, c=1.08, 26.0° C.) m.p. 141-143° C.

[0450] No.1a-173

[0451] CDCl₃300 MHz; 1.15-2.42(17H, m), 2.91(1H, m), 5.15(1H, d, J=4.2 Hz), 5.25-5.40(2H, m), 7.85(1H, t, J=7.2 Hz), 8.00(1H, t, J=8.1 Hz), 8.15-8.20(2H, m), 8.67(1H, d, J=8.1 Hz), 8.73(1H, d, J=8.1 Hz), 8.83(1H, s), 9.43(1H, s). IR (KBr): 3422, 3269, 3046, 2952, 2871, 1711, 1617, 1447, 1333, 1243, 1161, 1146/cm. [α]_D=−41.0° (CH₃OH, c=1.01, 23° C.).

[0452] No.1a-174

[0453] CDCl₃+d₆-DMSO 300 MHz; 1.00-1.92(14H, m), 2.20(2H, t, J=6.6 Hz), 2.35(1H, m), 2.92(1H, m), 5.05-5.22(2H, m), 6.63(1H, d, J=5.4 Hz), 7.77-7.92(3H, m), 8.31(1H, d.d, J=1.8 and 8.7 Hz), 8.59(1H, d, J=8.7 Hz), 8.73(1H, d, J=8.7 Hz), 9.01(1H, s), 9.55(1H, d, J=1.8 Hz). IR (KBr): 3433, 3252, 2952, 2871, 1696, 1578, 1423, 1335, 1308, 1219, 1185, 1160, 1106/cm. [α]_D=−19.3° (DMSO, c=0.50, 23° C.).

[0454] No.1a-175

[0455] CDCl₃300 MHz; 0.96-1.87(14H, m), 2.20-2.25(3H, m), 2.95(1H, m), 3.66(3H, s), 4.74(1H, d, J=6.6 Hz), 5.10-5.12(2H, m), 6.88(1H, d, J=1.2 Hz), 7.37-7.50(3H, m), 7.56(1H, dd, J=8.7, 1.5 Hz), 7.68-7.77(3H, m), 8.06(1H, s), 9.44(1H, dd, J=1.2 Hz). IR (CHCl₃): 3462, 3374, 3026, 3006, 2952, 2872, 1724, 1610, 1580, 1484, 1452, 1358, 1309, 1147. [α]_D=+16.4° (CHCl₃, c=1.05, 26° C.). mp. 130-132° C.

[0456] No.1a-176

[0457] CDCl₃+CD₃OD 300 MHz; 1.00-2.02(14H, m), 2.22(1H, m), 2.29(2H, t, J=6.9 Hz), 2.88(1H, m), 5.16-5.26(2H, m), 6.87(1H, s), 7.28-7.57(4H, m), 7.69(1H, d, J=8.4 Hz), 7.75-7.78(2H, m), 7.99(1H, s). IR (KBr): 3254, 2944, 1704, 1484, 1453, 1358, 1305, 1147. [α]_D=+13.0° (CH₃OH, c=1.02, 24° C.), mp. 160-161° C.

[0458] No.1a-177

[0459] CDCl₃300 MHz; 0.96-1.88(14H, m), 1.88-2.26(3H, m), 2.94(1H, m), 3.67(3H, s), 3.87(3H, s), 4.67(1H, brs), 5.08-5.14(2H, m), 6.77(1H, d, J=1.5 Hz), 6.99-7.02(2H, m), 7.53-7.5 7(1H, m), 7.65-7.70(3H, m), 8.00(1H, s), 9.27(1H, brs). IR (CHCl₃): 3426, 3376, 3006, 2952, 1724, 1610, 1495, 1438, 1357, 1308, 1282, 1249, 1177, 1147/cm. [α]_D=+18.1° (CHCl₃, c=1.02, 22° C.).

[0460] No.1a-178

[0461] CDCl₃+CD₃OD 300 MHz; 0.96-1.91(14H, m), 2.19(1H, m), 2.27(2H, t, J=6.0 Hz), 2.85(1H, m), 3.87(3H, s), 5.16-5.23(2H, m), 6.99-7.02(2H, m), 7.41(1H, m), 7.64-7.73(3H, m), 7.92(1H, m). IR (CHCl₃): 3366, 3261, 3004, 2954, 2873, 1705, 1611, 1496, 1458, 1438, 1304, 1286, 1253, 1180, 1149, 1128/cm. [α]_D=+14.6° (CHCl₃, c=1.02, 22° C.).

[0462] No.1a-179

[0463] CDCl₃+CD₃OD 300 MHz; 0.96-1.87(14H, m), 2.15-2.23(3H, m), 2.93(1H, m), 3.85(3H, s), 5.10-5.16(2H, m), 6.90-6.93(2H, m), 7.50(1H, m), 7.60-7.65(3H, m), 7.91(1H, d, J=0.9 Hz). IR (CHCl₃): 3369, 3270, 2950, 2873, 1719, 1612, 1498, 1456, 1440, 1359, 1306, 1269, 1219, 1146, 1127/cm. [α]_D=+18.1° (CH₃OH, c=1.00, 22° C.).

[0464] No.1a-180

[0465] CDCl₃+CD₃OD 300 MHz; 1.03-1.86(14H, m), 2.08-2.17(3H, m), 2.91(1H, m), 5.06-5.10(2H, m), 6.76(1H, m), 6.86-6.90(2H, m), 7.48(1H, m), 7.61-7.69(3H, m), 7.89(1H, m). IR (CHCl₃): 3360, 3259, 2954, 2873, 1706, 1612, 1497, 1457, 1360, 1306, 1272, 1230, 1176, 1148, 1126/cm. [α]_D=+20.3° (CH₃OH, c=1.00, 22° C.).

[0466] No.1a-181

[0467] CDCl₃300 MHz; 0.97-1.96(14H, m), 2.15(1H, m), 2.29(2H, t, J=6.9 Hz), 3.05(1H, m), 3.81(3H, s), 5.08(1H, d, J=6.9 Hz), 5.23-5.25(2H, m), 6.62(1H, s), 7.47-7.54(5H, m), 7.59(1H, m), 7.70(1H, m), 7.97(1H, m). IR (CHCl₃): 3380, 3260, 3020, 2946, 2868, 1708, 1466, 1388;, 1328, 1149/cm. [α]_D=+32.9° (CHCl₃, c=1.07, 22° C.).

[0468] No.1a-182

[0469] CDCl₃300 MHz; 0.94-1.90(14H, m), 2.25(2H, t, J=7.5 Hz), 2.30(1H, m), 2.98(1H, m), 3.70(3H, s), 4.83(1H, d, J=6.6 Hz), 5.13-5.16(2H, m), 6.95(1H, d, J=1.5 Hz), 7.11-7.23(2H, m), 7.43(1H, d, J=8.1 Hz), 7.65(1H, d, J=8.1 Hz), 7.79-7.93(4H, m), 9.08(1H, br). IR (CHCl₃): 3458, 3372, 3020, 3002, 2946, 2868, 1719, 1598, 1452, 1422, 1321, 1300, 1157/cm. [α]_D=−6.6° (CHCl₃, c=1.00), mp 150-151° C.

[0470] No.1a-183

[0471] CDCl₃300 MHz; 0.95-1.94(14H, m), 2.26(1H, m), 2.28(2H, t, J=7.5 Hz), 3.00(1H, m), 5.16-5.19(2H, m), 5.32(1H, d, J=7.2 Hz), 6.93(1H, d, J=1.2 Hz), 7.13(1H, m), 7.22(1H, dd, J=7.8, 6.6 Hz), 7.42(1H, d, J=7.8 Hz), 7.63(1H, d, J=7.8 Hz), 7.76(2H, d, J=8.4 Hz), 7.90(2H, d, J=8.4 Hz), 8.95(1H, br). IR (CHCl₃): 3458, 3374, 3260, 3020, 3002, 2948, 2868, 1708, 1598, 1452, 1422, 1301, 1156/cm. [α]_D=+17.9° (CHCl₃, c=1.01, 22° C.).

[0472] No.1a-184

[0473] CDCl₃200 MHz; 0.92-2.00(14H, m), 2.20(1H, m), 2.34(2H, t, J=6.8 Hz), 3.05(1H, m), 5.20-5.36(3H, m), 7.39-7.44(2H, m), 7.61-7.66(1H, m), 7.80-7.84(1H, m), 8.05(2H, d, J=8.6 Hz), 8.40(2H, d, J=8.6 Hz). IR (CHCl₃): 3384, 3271, 3019, 2958, 1709, 1615, 1599, 1551, 1453, 1405, 1344, 1326, 1243, 1163/cm. [α]_D=+18.5° (CHCl₃, c=1.00, 21° C.).

[0474] No.1a-185

[0475] CDCl₃300 MHz; 0.89-2.20(15H, m), 2.26(2H, d.t, J=2.1 and 7.2 Hz), 2.99(1H, m), 5.08(1H, d, J=6.3 Hz), 5.09-5.24(2H, m), 6.90(1H, d, J=1.2 Hz), 7.32-7.48(4H, m), 7.64-7.72(3H, m), 8.20(1H, d, J=1.2 Hz), 9.00(1H, s). IR (CHCl₃): 3464, 3375, 3275, 3022, 2956, 1707, 1605, 1490, 1449, 1356, 1322, 1219, 1147, 1131/cm. [α]_D=+21.6° (CHCl₃, c=1.01, 23° C.).

[0476] No.1a-186

[0477] CDCl₃: 300 MHz; 1.36-2.24(14H, m), 2.31(2H, t, J=7.4 Hz), 2.49(1H, brs), 3.37(1H, m), 3.67(3H, s), 5.38-5.50(2H, m), 7.40-7.68(9H, m). IR (CHCl₃): 3375, 1727, 1602, 1435, 1362, 1221, 1207, 1168, 1045/cm.

[0478] No.1a-187

[0479] CDCl₃: 300 MHz; 1.10-2.25(14H, m), 2.36(2H, t, J=7.2 Hz), 2.47(1H, m), 3.37(1H, m), 5.35-5.54(2H, m), 5.62(1H, d, J=7.2 Hz), 7.39-7.70(9H, m). IR (CHCl₃): 3674, 3496, 3376, 3234, 3012, 2952, 2880, 2650, 1725(sh), 1709, 1602, 1485, 1420, 1360, 1167/cm. [α]_D=+32° (CHCl₃, c=1.69).

[0480] No.1a-188

[0481] CDCl₃200 MHz; 0.86-1.92(14H, m) 2.22(3H, m), 2.36(3H, m), 2.95(1H, m), 3.67(3H, s), 3.93(3H, s), 4.81(1H, d, J=6.2 Hz), 5.04-5.20(2H, m), 7.02-7.05(2H, m), 7.31(1H, d, J=8.6 Hz), 7.39(1H, d, J=7.8 Hz), 7.79-7.89(3H, m). IR (CHCl₃): 3385, 3286, 3029, 3019, 3015, 2954, 2877, 1718, 1617, 1598, 1567, 1507, 1311, 1269, 1153/cm. [α]_D=−29.4° (CHCl₃, c=1.01, 25° C.).

[0482] No.1a-189

[0483] [α]_D=−7.7° (CHCl₃, c=1.00, 24° C.).

[0484] No.1a-190

[0485] [α]_D=−17.3° (CHCl₃, c=1.00, 24° C.).

[0486] No.1a-191

[0487] CDCl₃300 MHz; 0.95-2.20(14H, m), 2.30(1H, m), 2.36(2H, d, J=6.9 Hz), 3.21(1H, m), 4.25(2H, s), 5.07(1H, d, J=7.8 Hz), 5.35-5.48(2H, m), 7.25(1H, dd, J=1.8 and 8.1 Hz), 7.32-7.35(2H, m), 7.59(1H, d, J=8.1 Hz), 7.94(1H, s), 8.14(1H, d, J=2.7 Hz), 8.23(1H, d.d, J=2.7 and 8.7 Hz). IR (CHCl₃): 3386, 3026, 3015, 2957, 2877, 2633, 1702, 1617, 1573, 1530, 1348, 1123/cm. [α]_D=−6.1° (CHCl₃, c=1.01, 25° C.).

[0488] No.1a-192

[0489] CDCl₃300 MHz; 0.92-2.20(14H, m), 2.13(3H, m), 3.23(1H, m), 3.64(3H, s), 3.94(3H, s), 4.22(2H, s), 4.36(1H, d, J=7.8 Hz), 5.37-5.42(2H, m), 7.16-7.42(6H, m), 7.53(1H, d, J=8.4Hz), 7.94(1H, s). IR (CHCl₃): 3389, 3022, 3013, 2953, 2877, 1716, 1616, 1560, 1485, 1340, 1326, 1124/cm. [α]_D=−15.2° (CHCl₃, c=1.01, 25° C.).

[0490] No.1a-193

[0491] CDCl₃300 MHz; 0.92-2.20(14H, m), 2.25(1H, m), 2.35(2H, t, J=7.2 Hz), 3.17(1H, m), 4.22(2H, s), 4.91(1H, d, J=7.5 Hz), 5.37-5.42(2H, m), 7.13-7.43(6H, m), 7.60(1H, d, J=8.1 Hz), 8.05(1H, s). IR (CHCl₃): 3511, 3387, 3029, 3020, 3011, 2957, 2877, 2651, 1698, 1614, 1560, 1505, 1320, 1280, 1252, 1126/cm. [α]_D=−0.9° (CHCl₃, c=1.00, 25° C.).

[0492] No.1b-1

[0493] CDCl₃300 MHz; 0.98-1.56(15H, m), 1.85-1.90(5H, m), 2.23(1H, m), 3.05(1H, m), 3.66(3H, s), 4.77(1H, d, J=6.0 Hz), 6.08-5.28(2H, m), 7.46(3H, m), 7.38-7.54(2H, d, J=7.5 Hz), 7.72(2H, d, J=8.4 Hz), 7.93(2H, d, J=8.4 Hz).

[0494] IR (CHCl₃): 3384, 3028, 2952, 2876, 1719, 1595, 1391, 1322, 1155/cm. [α]₄₃₆+4.0˜6.0(CHCl₃, c=1.00, 23° C.). mp. 96-98° C.

[0495] No.1b-2

[0496] CDCl₃300 MHz; 0.98-1.52(15H, m), 1.85-1.90(5H, m), 2.17(1H, m), 3.00(1H, m), 3.67(3H, s), 4.05(2H, s), 4.83(1H, d, J=6.0 Hz), 5.05-5.23(2H, m), 7.14(2H, d, J=7.2 Hz), 7.17-7.32(5H, m), 7.78(2H, d, J=8.4 Hz). IR (CHCl₃): 3384, 3026, 2952, 2874, 1719, 1595, 1453, 1407, 1320, 1180/cm. [α]_D=+2.5° (CHCl₃, c=1.02, 24° C.).

[0497] No.1b-3

[0498] CDCl₃300 MHz; 0.96-2.06(20H, m), 2.07(1H, m), 3.07(1H, m), 4.04(2H, s), 5.21-5.35(2H, m), 5.55(1H, d, J=6.9 Hz), 7.14(2H, d, J=6.6 Hz), 7.20-7.32(5H, m), 7.78(2H, d, J=8.1H). IR (CHCl₃): 3250, 3022, 2950, 1699, 1596, 1495, 1453, 1405, 1318, 1153/cm. [α]_D=+17.1° (CHCl₃, c=1.01, 25° C.). mp. 129-131° C.

[0499] No.1b-4

[0500] CDCl₃200 MHz; 0.90-2.10(15H, m), 1.19(3H, s), 1.20(3H, s), 3.11(1H, m), 6.24-5.32(2H, m), 5.70(1H, d, J=6.6 Hz), 7.38-7.68(4H, m), 7.96-8.04(2H, m), 8.53(1H, d, J=1.4 Hz). IR (CHCl₃): 3384, 3246, 2958, 1701, 1632, 1595, 1468, 1445, 1322, 1216, 1202, 1190, 1155, 1122/cm. [α]_D=+10.8° (CHCl₃, c=0.51, 23° C.).

[0501] No.1b-5

[0502] 1.02-2.10(15H, m), 1.16(6H, s), 3.02(1H, m), 4.09(3H, s), 5.23-5.28(2H, m), 5.76(1H, d, J=7.2 Hz), 7.36-7.63(4H, m), 7.97(1H, d, J=7.8 Hz), 8.16(1H, s). IR (CHCl₃): 3369, 2959, 1702, 1635, 1585, 1468, 1454, 1441, 1415, 1318, 1222, 1189, 1170, 1154/cm. [α]_D=+9.9° (CHCl₃, c=1.00, 23° C.).

[0503] No.1c-1

[0504] CDCl₃300 MHz; 1.10-2.02(14H, m), 2.27(2H, t, J=7.5 Hz), 2.60(1H, m), 2.89(3H, s), 3.31(1H, m), 3.64(3H, s), 5.16-5.30(2H, m), 7.34-7.42(3H, m), 7.50-7.59(2H, m), 7.62-7.68(2H, m), 7.76-7.82(2H, m). IR (CHCl₃): 3020, 2946, 2868, 2212, 1727, 1596, 1495, 1437, 1339, 1156, 1135, 1084/cm. [α]_D=−16.1° (CHCl₃, c=1.05, 25.0° C.). m.p. 100-102° C.

[0505] No.1c-2

[0506] CDCl₃300 MHz; 1.10-2.05(14H, m), 2.23(2H, t, J=7.5 Hz), 2.53(1H, m), 2.91(3H, s), 3.35(1H, m), 3.62(3H, s), 5.02-5.30(2H, m), 7.50-7.60(3H, m), 7.90-8.08(6H, m). IR (CHCl₃): 3016, 2946, 2868, 1728, 1437, 1398, 1340, 1160, 1086/cm. [α]_D=−32.5° (CHCl₃, c=1.00, 25.0° C.).

[0507] No.1c-3

[0508] CD₃OD 300 MHz; 1.15-2.05(14H, m), 2.13(2H, t, J=7.2 Hz), 2.47(1H, m), 2.91(3H, s), 3.27(1H, m), 4.90-6.30(2H, m), 7.37-7.44(3H, m), 7.53-7.61(2H, m), 7.71-7.77(2H, m), 7.81-7.87(2H, m). IR (KBr): 3412, 2999, 2951, 2871, 2217, 1560, 1399, 1243, 1159, 1137, 1103, 1084. [α]_D=−8.6° (CH₃OH, c=1.03, 23° C.).

[0509] No.1d-1

[0510] CDCl₃300 MHz; 1.00-2.16(15H, m), 2.36(2H, t, J=7.2 Hz), 3.17(1H, m), 3.33(3H, s), 5.23-5.43(3H, m), 7.51-7.59(3H, m), 7.91-8.10(6H, m), 9.02(1H, brs). IR (CHCl₃): 3382, 3268, 3028, 2954, 2874, 1715, 1442, 1400, 1337, 1162, 1120, 1089/cm. [α]_D=+40.0° (CHCl₃, c=0.53, 22° C.).

[0511] No.1d-2

[0512] CDCl₃300 MHz; 1.03-2.30(17H, m), 3.03(1H, m), 4.03(2H, s), 5.26(2H, m), 5.84(1H, br), 5.25-5.29(1H, d, J=6.6 Hz), 6.03(1H, br), 7.14(2H, d, J=8.1 Hz), 7.26-7.31(5H, m), 7.80(2H, d, J=8.1 Hz). IR (CHCl₃): 3376, 3002, 2946, 1669, 1595, 1492, 1454, 1406, 1318, 1154/cm. [α]_D=+4.3° (CHCl₃, c=1.00, 23° C.).

[0513] No.1d-3

[0514] CDCl₃300 MHz; 0.96-2.17(17H, m), 2.33(2H, t, J=6.9 Hz), 3.01(1H, m), 4.04(2H, s), 5.10(1H, d, J=6.6 Hz), 5.21-5.26(2H, m), 7.14(2H, d, J=8.7 Hz), 7.16-7.32(5H, m), 7.78(2H, d, J=8.4 Hz). IR (CHCl₃): 3260, 3020, 2946, 1711, 1596, 1492, 1457, 1407, 1318, 1154/cm. [α]_D=+9.3° (CHCl₃, c=1.09, 25° C.).

[0515] No.1d-4

[0516] CDCl₃300 MHz; 0.95-2.14(15H, m), 2.34(2H, t, J=7.2 Hz), 3.09(1H, m), 3.30(3H, m), 4.04(2H, s), 5.19(1H, d, J=7.2 Hz), 5.22-5.39(2H, m), 7.10-7.35(7H, m), 7.81(2H, d, J=8.1 Hz), 9.10(1H, brs). IR (CHCl₃): 3382, 3260, 3028, 2952, 2874, 2670, 1713, 1595, 1492, 1450, 1405, 1338, 1160, 1120, 1092/cm. [α]_D=+22.2° (CHCl₃, c=1.07, 22° C.).

[0517] No.1d-5

[0518] CDCl₃300 MHz; 1.00-2.10(14H, m), 2.30-2.39(3H, m), 3.15(1H, m), 3.35(3H, s), 5.18-5.40(3H, m), 7.41(1H, d. t., J=0.9and 7.8 Hz), 7.50-7.69(3H, m), 7.88-8.15(2H, m), 8.60(1H, d, J=1.5 Hz), 9.06(1H, s). IR (CHCl₃): 3382, 3268, 3028, 2954, 2874, 1714, 1442, 1402, 1338, 1188, 1155, 1121, 1072/cm. [α]_D=+15.3° (CHCl₃, c=1.00, 22° C.).

[0519] No.1e-1

[0520] CDCl₃300 MHz; 1.19-2.45(19H, m), 2.58(1H, m), 5.63(1H, d, J=3.0 Hz), 7.42-7.65(4H, m), 7.94(2H, m), 8.49-8.50(1H, m). IR (CHCl₃): 3293, 3024, 1710, 1595, 1584, 1467, 1445, 1410, 1324, 1222, 1213, 1206, 1190, 1160/cm. [α]_D=−41.1° (CHCl₃, c=1.01, 23° C.).

[0521] No.1e-2

[0522] CDCl₃300 MHz; 1.10-2.25(19H, m), 2.94(1H, m), 4.12(3H, s), 5.53(1H, d, J=7.2 Hz), 7.39(1H, m), 7.50-7.62(3H, m), 7.96(1H, d, J=7.5 Hz), 8.13(1H, s). IR (CHCl₃): 3367, 3025, 2955, 1711, 1634, 1600, 1584, 1468, 1454, 1440, 1415, 1342, 1317, 1222, 1189, 1157/cm. [α]_D=+1.2° (CHCl₃, c=1.00, 25° C.).

[0523] No.1f-1

[0524] CDCl₃300 MHz; 1.08-2.47(19H, m), 2.56(1H, m), 3.52(2H, t, J=6.6 Hz), 5.59(1H, d, J=2.4 Hz), 7.40-7.66(4H, m), 7.95-8.04(2H, m), 8.50(1H, d, J=1.8 Hz). IR (CHCl₃): 3624, 3383, 3295, 2950, 2877, 1705, 1595, 1584, 1468, 1445, 1405, 1347, 1337, 1324, 1224, 1190, 1160/cm. [α]_D=−54.1° (CHCl₃, c=1.01, 23° C.).

[0525] No.1f-2

[0526] CDCl₃300 MHz; 1.08-2.24(19H, m), 2.94(1H, m), 3.53(2H, t, J=6.3 Hz), 4.13(3H, s), 5.47(1H, d, J=6.6 Hz), 7.36-7.63(4H, m), 7.96(1H, d, J=6.3 Hz), 8.14(1H, s). IR (CHCl₃): 3625, 3368, 3025, 3013, 2949, 2877, 1710, 1634, 1600, 1584, 1468, 1454, 1440, 1415, 1342, 1317, 1232, 1220, 1189, 1157/cm. [α]_D=−5.6° (CHCl₃, c=1.00, 25° C.).

[0527] No.1g-1

[0528] CDCl₃200 MHz; 1.17-2.34(15H, m), 3.22(1H, m), 5.10-5.16(2H, m), 5.45(1H, d, J=7.0 Hz), 7.35-7.66(4H, m), 7.95-8.01(2H, m), 8.51(1H, d, J=2.0 Hz). IR (CHCl₃): 3383, 3275, 2959, 1707, 1595, 1584, 1468, 1445, 1425, 1319, 1269, 1248, 1190, 1149, 1123/cm. [α]_D=+64.3° (CHCl₃, c=1.01, 23° C.).

[0529] No.1g-2

[0530] CDCl₃300 MHz; 1.10-2.15(13H, m), 2.36(2H, t, J=7.2 Hz), 3.21(1H, m), 4.09(3H, s), 5.10-5.22(2H, m), 5.43(1H, d, J=7.8 Hz), 7.36-7.62(4H, m), 7.96(1H, d, J=7.8 Hz), 8.12(1H, s). IR (CHCl₃): 3366, 2959, 1708, 1635, 1600, 1585, 1467, 1454, 1440, 1415, 1345, 1318, 1233, 1189, 1152/cm. [α]_D=+103.1° (CHCl₃, c=1.01, 23° C.).

[0531] No.1h-1

[0532] CDCl₃300 MHz; 0.90.1.60(17H, m), 1.83(1H, m), 2.11(1H, m), 2.22(2H, t, J=7.2 Hz), 3.07(1H, m), 5.11(1H, d, J=7.2 Hz), 7.38-7.47(1H, m), 7.50-7.60(1H, m), 7.60-7.72(2H, m), 7.88-8.12(2H, m), 8.54(1H, d, J=0.9 Hz). IR (CHCl₃): 3382, 3274, 2926, 1707, 1464, 1442, 1318, 1266, 1188, 1153, 1121, 1105, 1071, 1019/cm. [α]_D=−2.8° (CHCl₃, c=1.01, 23° C.).

[0533] No.1i-1

[0534] [α]₃₆₅+50.9° (CHCl₃, c=1.01, 24° C.).

[0535] No.1i-2

[0536] CDCl₃300 MHz; 0.98-1.70(11H, m), 1.80-2.00(5H, m), 2.19(1H, m), 3.03(1H, m), 3.64(2H, t, J=6.6 Hz), 4.05(2H, s), 4.69(1H, d, J=6.6 Hz), 5.15(1H, m), 5.25(1H, m), 7.16(2H, d, J=7.2 Hz), 7.27-7.32(5H, m), 7.77(2H, d, J=8.4 Hz). IR (CHCl₃): 3376, 3004, 2946, 2316, 1596, 1492, 1453, 1407, 1318, 1154/cm. [α]_D=+3.5° (CHCl₃, c=1.00, 22° C.). mp. 80.5-82.0° C.

[0537] No.1j-1

[0538] [α]₄₃₆=±0.5° (CHCl₃, c=1.05, 22° C.).

[0539] No.1j-2

[0540] [α]_D=−9.7±0.6° (CHCl₃, c=1.06, 22° C.).

[0541] No.1j-3

[0542] [α]_D=+15.0±0.5° (CH₃OH, c=1.06, 24.5° C.). mp. 101-108° C.

[0543] No.1j-4

[0544] [α]_D=−28.0±0.6° (CHCl₃, c=1.06, 24° C.). mp. 159-161° C.

[0545] No. 1j-5

[0546] [α]_D=−12.5±0.5° (CHCl₃, c=1.04, 23° C.). mp. 99-101° C.

[0547] No.1j-6

[0548] CDCl₃300 MHz; 0.90-2.03(14H, m), 2.20(1H, m), 2.30(2H, t, J=7.3 Hz), 3.00(1H, m), 3.68(3H, s), 4.76(1H, d, J=6.8 Hz), 5.13-5.35(2H, m), 7.01-7.08(4H, m), 7.19-7.26(1H, m), 7.37-7.46(2H, m), 7.80-7.84(2H, m). IR (CHCl₃): 3382, 3280, 3080, 3016, 2952, 2900, 1727, 1582, 1486, 1432, 1322, 1150/cm. [α]_D=−31.0° (CHCl₃, c=1.05, 26° C.).

[0549] No.1j-7

[0550] CDCl₃300 MHz; 0.91-2.09(14H, m), 2.15(1H, m), 2.35(2H, t, J=7.5 Hz), 3.01(1H, m), 5.17(1H, d, J=6.8 Hz), 5.21-5.34(2H, m), 7.01-7.08(4H, m), 7.15-7.27(1H, m), 7.37-7.43(2H, m), 7.80-7.85(2H, m). IR (CHCl₃): 3474, 3386, 3270, 3024, 2958, 2900, 2675, 1711, 1584, 1488, 1420, 1323, 1298, 1150/cm. [α]_D=−13.4° (CHCl₃, c=1.01, 26° C.).

[0551] No.1j-8

[0552] CDCl₃300 MHz; 0.95-2.14(13H, m), 2.30(2H, t, J=7.5 Hz), 2.36(1H, m), 2.84(1H, m), 2.91(1J=4.9 Hz), 3.66(3H, s), 5.33-5.52(2H, m), 6.82-6.87(1H, m), 6.93-7.00(2H, m), 7.09-7.15(4H, m), 7.28-7.36(2H, m), 7.54-7.59(1H, m). IR (CHCl₃): 3350, 3010, 2950, 2880, 1728, 1603, 1582, 1489 1461, 1438, 1360, 1160/cm. [α]_D=+75.1° (CHCl₃, c=1.13, 26° C.).

[0553] No.1j-9

[0554] CDCl₃300 MHz; 0.95-2.03(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.5 Hz), 3.06(1H, m), 3.68(3H, s), 4.98(1H, d, J=7.4 Hz), 5.14-5.34(2H, m), 7.46-7.54(2H, m), 7.60-7.68(1H, m), 7.75-7.80(2H, m), 7.88-7.92(2H, m), 7.99-8.03(2H, m).

[0555] IR (CHCl₃): 3384, 3280, 3020, 2960, 2888, 1727, 1662, 1600, 1316, 1273, 1163/cm. [α]_D=−41.0° (CHCl₃, c=1.17, 26° C.).

[0556] No.1j-10

[0557] CDCl₃+CD₃OD 300 MHz; 0.94-2.08(14H, m), 2.21(1H, m), 2.34(2H, t, J=6.2 Hz), 3.04(1H, m), 5.21-5.35(2H, m), 5.40(1H, m), 7.49-7.58(2H, m), 7.64-7.68(1H, m), 7.79-8.06(6H, m). IR (CHCl₃): 3475, 3370, 3250, 3018, 2956, 2976, 2650, 1709, 1662, 1595, 1445, 1420, 1395, 1317, 1274, 1163/cm. [α]_D=−17.1° (CHCl₃, c=1.13, 25° C.).

[0558] No.1j-11

[0559] CDCl₃300 MHz; 1.06-1.98(14H, m), 2.24-2.29(3H, m), 3.13(1H, m), 3.66(3H, s), 5.10-5.24(2H, m), 5.40(1H, d, J=6.3 Hz), 7.39-7.49(3H, m), 7.59-7.64(3H, m), 7.80-7.83(2H, m), 8.08-8.11(1H, m). IR (CHCl₃): 3302, 3012, 2948, 2905, 1727, 1661, 1593, 1436, 1332, 1312, 1287, 1271, 1165/cm. [α]_D=+15.6° (CHCl₃, c=1.03, 26° C.).

[0560] No.1j-12

[0561] CDCl₃300 MHz; 1.08-1.98(14H, m), 2.23(1H, m), 2.33(2H, t, J=7.5 Hz), 3.16(1H, m), 5.18-5.26(2H, m), 5.39-5.45(1H, m), 7.39-7.49(3H, m), 7.60-7.64(3H, m), 7.80-7.83(2H, m), 8.09-8.12(1H, m). IR (CHCl₃): 3325, 3022, 2956, 2872, 2680, 1708, 1662, 1603, 1598, 1425, 1340, 1316, 1288, 1271, 1165/cm. [α]_D=+9.7° (CHCl₃, c=0.52, 25° C.).

[0562] No.1j-13

[0563] CDCl₃300 MHz; 0.95-2.00(14H, m), 2.20(1H, m), 2.27(2H, t, J=6.3 Hz), 3.03(1H, m), 3.67(3H, s), 4.99(1H, d, J=6.6 Hz), 5.12-5.31(2H, m), 7.47-7.55(2H, m), 7.60-7.69(2H, m), 7.76-7.81(2H, m), 7.96-8.05(1H, m), 8.08-8.14(1H, m), 8.27-8.28(1H, m). IR (CHCl₃): 3674, 3538, 3376, 3276, 3012, 2948, 2860, 1726, 1662, 1595, 1440, 1335, 1317, 1297, 1274, 1166, 1150/cm. [α]_D=+10.2° (CHCl₃, c=1.00, 25° C.).

[0564] No.1j-14

[0565] CDCl₃300 MHz; 0.93-2.08(14H, m), 2.21(1H, m), 2.32(2H, t, J=6.3 Hz), 3.00(1H, m), 5.20-5.36(2H, m), 5.38(1H, d, J=6.2 Hz), 7.50-7.55(2H, m), 7.63-7.71(2H, m), 7.77-7.81(2H, m), 7.99-8.04(1H, m), 8.10-8.18(1H, m), 8.32-8.36(1H, m). IR (CHCl₃): 3674, 3480, 3374, 3258, 3012, 2950, 2875, 2650, 1709, 1662, 1598, 1418, 1335, 1317, 1274, 1143/cm. [α]_D=+61.0° (CHCl₃, c=1.19, 25° C.).

[0566] No.1j-15

[0567] CDCl₃300 MHz; 0.90-2.00(14H, m), 2.19(1H, m), 2.30(2H, t, J=7.3 Hz), 3.01(1H, m), 3.67(3H, s), 4.82(1H, d, J=6.6 Hz), 5.14-5.34(2H, m), 7.36-7.39(3H, m), 7.53-7.57(2H, m), 7.62-7.66(2H, m), 7.83-7.88(2H, m). IR (CHCl₃): 3376, 3276, 3010, 2948, 2868, 2212, 1727, 1597, 1500, 1437, 1325, 1161/cm. [α]_D=−7.2° (CHCl₃, c=1.00, 26° C.).

[0568] No.1j-16

[0569] CDCl₃300 MHz; 0.93-2.03(14H, m), 2.15(1H, m), 2.36(2H, t, J=7.5 Hz), 3.05(1H, m), 5.20-5.40(3H, m), 7.36-7.39(3H, m), 7.55-7.66(4H, m), 7.84-7.88(2H, m). IR (CHCl₃): 3470, 3376, 3260, 3012, 2950, 2868, 2675, 2212, 1708, 1596, 1503, 1416, 1396, 1322, 1160. [α]_D=22.4° (CHCl₃, c=1.00, 26° C.).

[0570] No.1j-17

[0571] CDCl₃300 MHz; 1.00-1.60(9H, m), 1.79-1.89(5H, m), 2.17(1H, brs), 2.23(2H, t, J=7.2 Hz), 3.03(1H, m), 5.10-5.23(2H, m), 5.49(1H, d, J=6.6 Hz), 7.40(1H, t, J=7.4 Hz), 7.53(1H, t, J=7.2 Hz), 7.60-7.68(2H, m), 7.98-8.03(2H, m), 8.55(1H, d, J=1.5 Hz). IR (CHCl₃): 3516, 3384, 3270, 2666, 1708, 1632, 1595, 1584, 1467, 1445, 1425, 1374, 1345, 1321, 1269, 1248, 1218/cm. [α]_D=−7.8° (CHCl₃, c=1.01, 22° C.).

[0572] No.1j-18

[0573] CDCl₃300 MHz; 0.90-2.03(14H, m), 2.19(1H, m), 2.30(2H, t, J=7.5 Hz), 3.00(1H, m), 3.67(3H, s), 4.80(1H, d, J=6.4 Hz), 5.14-5.35(2H, m), 6.99-7.04(2H, m), 7.16-7.22(2H, m), 7.34-7.49(4H, m), 7.57-7.6 1(1H, m). IR (CHCl₃): 3376, 3276, 3012, 2948, 2875, 1727, 1583, 1488, 1471, 1432, 1330, 1311, 1150/cm. [α]_D=+54.0° (CHCl₃, c=0.99, 25° C.).

[0574] No.1j-19

[0575] CDCl₃300 MHz; 0.91-2.09(14H, m), 2.15(1H, m), 2.34(2H, t, J=7.5 Hz), 3.01(1H, m), 5.16(1H, d, J=6.6 Hz), 5.24-5.40(2H, m), 7.01-7.08(2H, m), 7.15-7.25(2H, m), 7.35-7.53(4H, m), 7.59-7.65(1H, m). IR (CHCl₃): 3470, 3376, 3260, 3012, 2950, 2875, 2640, 1708, 1583, 1488, 1471, 1430, 1335, 1305, 1149/cm. [α]_D=−21.0° (CHCl₃, c=1.30, 25° C.).

[0576] No.1j-20

[0577] CDCl₃300 MHz; 1.17(1H, m), 1.26-1.34(2H, m), 1.54-2.24(11H, m), 2.31(2H, t, J=7.4 Hz), 2.48(1H, brs), 3.37(1H, m), 3.67(3H, s), 5.35-5.50(2H, m), 7.39-7.68(9H, m). IR (CHCl₃): 3377, 1727, 1601, 1435, 1362, 1168/cm.

[0578] No.1j-21

[0579] CDCl₃300 MHz; 1.10-2.25(14H, m), 2.36(2H, t, J=7.2 Hz), 2.47(1H, m), 2.89(1H, m), 5.35-5.53(2H, m), 5.63(1H, d, J=7.2 Hz), 7.40-7.71(9H, m). IR (CHCl₃): 3674, 3496, 3374, 3234, 3010, 2952, 2870, 2640, 1730(sh), 1710, 1605, 1485, 1425, 1360, 1167/cm. [α]_D=−43.0° (CHCl₃, c=1.01, 25° C.).

[0580] No.1j-22

[0581] CDCl₃300 MHz; 0.98-1.95(14H, m), 2.25-2.31(3H, m), 2.95(1H, m), 5.19-5.30(2H, m), 5.33(1H, d, J=3.9 Hz), 6.58(1H, d, J=7.5 Hz), 6.80(1H, t, J=7.5 Hz), 6.99-7.05(1H, m), 7.44-7.53(6H, m), 7.60-7.73(9H, m), 7.94-7.73(3H, m), 8.23-8.26(2H, m), 10.66(1H, s). IR (CHCl₃): 3475, 3372, 3260, 3008, 2952, 2868, 2722, 1725, 1710(sh), 1663, 1590, 1571, 1525, 1448, 1437, 1345, 1314, 1161, 1112/cm. [α]_D=+12.9° (CHCl₃, c=0.12, 23° C.).

[0582] No.1j-23

[0583] CDCl₃300 MHz; 0.94˜1.94(14H, m), 2.23-2.30(3H, m), 2.98(1H, m), 3.68(3H, s), 5.09(1H, d, J=6.2Hz), 5.15-5.28(2H, m), 7.14-7.22(1H, m), 7.34-7.42(2H, m), 7.68-7.73(2H, m), 7.89-8.03(4H, m), 8.51(1H, s). IR (CHCl₃): 3372, 3275, 1724, 1673, 1599, 1438, 1320, 1161/cm. [α]_D=+17.0° (CHCl₃, c=1.38, 25° C.).

[0584] No.1j-24

[0585] CDCl₃+CD₃OD 300 MHz; 0.96-2.05(14H, m), 2, 25-2.34(3H, m), 2.92(1H, m), 5.16-5.34(2H, m), 7.14-7.22(1H, m), 7.29-7.42(2H, m), 7.70(2H, d, J=7.6 Hz), 7.92-8.05(4H, m). IR (CHCl₃): 3616, 3426, 3375, 3010, 2950, 2828, 2645, 1708, 1672, 1599, 1439, 1323, 1161/cm. [α]_D=+21.0° (CH₈OH, c=1.00, 22° C.).

[0586] No.1j-25

[0587] CDCl₃300 MHz; 1.03(1H, m), 1.18-2.01(13H, m), 2.20(1H, brs), 2.27(2H, t, J=7.4 Hz), 3.08(1H, m), 3.66(3H, s), 5.11(H, d, J=6.6 Hz), 5.14-5.34(2H, m), 7.54-7.62(3H, m), 8.04-8.32(

[0588] 6H, m). IR (CHCl₃): 3384, 3278, 1726, 1605, 1484, 1448, 1331, 1161/cm.

[0589] No.1j-26

[0590] CDCl₃+CD₈OD 300 MHz; 1,03-2.10(14H, m), 2.22(1H, m), 2.31(2H, t, J=7.5 Hz), 2.98(1H, m), 5.23-5.38(2H, m), 7.55-7.66(3H, m), 8.05-8.08(2H, m), 8.14-8.18(2H, m), 8.28-8.31(2H, m). IR (Nujol): 3260, 2720, 2660, 1711, 1545, 1460, 1317, 1163/cm. [α]_D=+15.8° (CH₃OH, c=1.01, 22° C.).

[0591] No.1j-27

[0592] [α]_D=+16.7° (CHCl₃, c=1.00, 23° C.).

[0593] No.1j-28

[0594] CDCl₃300 MHz; 1.01(1H, m), 1.14-1.29(2H, m), 1.46-2.19(11H, m), 2.33(2H, t, J=7.2 Hz), 2.41(1H, brs), 3.18-3.21(5H, m), 3.68(3H, s), 3.73-3.76(4H, m), 4.37(1H, d, J=7.2 Hz), 5.35-5.45(2H, m). IR (CHCl₃): 3392, 1727, 1435, 1335, 1148/cm. [α]_D=+10.7° (CHCl₃, c=1.39, 26° C.).

[0595] No.1j-29

[0596] CDCl₃300 MHz; 1.00(1H, m), 1.20-1.29(2H, m), 1.48-2.25(12H, m), 2.37(2H, t, J=7.2 Hz), 3.17-3.22(5H, m), 3.74-3.79(4H, m), 4.79(1H, d, J=7.8 Hz), 5.34-5.54(2H, m). IR (CHCl₃): 3470, 3390, 3270, 2675, 1709, 1455, 1420, 1315, 1147/cm. [α]_D=+16.8° (CHCl₃, c=1.42, 26° C.).

[0597] No.1k-1

[0598] [α]_D=−25.4° (CHCl₃, c=1.08, 23° C.).

[0599] No.1k-2

[0600] CDCl₃200 MHz; 1.07-2.28(14H, m), 2.32(2H, t, J=7.4 Hz), 2.63(1H, m), 3.63(3H, s), 3.93(1H, m), 5.30-5.52(2H, m), 6.35(1H, d, J=7.0 Hz), 7.48-7.60(3H, m), 7.88-8.02(6H, m). IR (CHCl₃): 3438, 3002, 2946, 2868, 1727, 1652, 1514, 1485, 1363, 1310, 1245, 1154/cm. [α]_D=80.4° (CHCl₃, c=1.01, 24.0° C.).

[0601] No.1k-3

[0602] CDCl₃200 MHz; 1.10-2.26(14H, m), 2.37(2H, t, J=7.2 Hz), 2.60(1H, m), 3.93(1H, m), 5.30-5.50(2H, m), 6.33(1H, d, J=7.5 Hz), 7.48-7.58(3H, m), 7.88-7.99(6H, m). IR (CHCl₃): 3446, 3004, 2952, 2874, 1709, 1652, 1515, 1485, 1305, 1153/cm. [α]_D=−96.4° (CHCl₃, c=1.05, 23.0° C.).

[0603] No.1k-4

[0604] CDCl₃300 MHz; 1.05-2.17(14H, m), 2.38(2H, t, J=7.2 Hz), 2.52(1H, m), 3.81(1H, m), 5.33-5.50(2H, m), 6.08(1H, d, J=7.6 Hz), 7.39-7.53(3H, m), 7.57-7.62(6H, m). IR (CHCl₃): 3420, 3250, 3008, 2948, 2870, 2660, 2208, 1735(sh), 1705, 1640, 1500/cm. [α]_D=−21.9±0.6° (CHCl₃, c=1.02, 22° C.).

[0605] No.1k-5

[0606] CDCl₃300 MHz; 1.05-2.14(14H, m), 2.38(2H, t, J=7.2 Hz), 2.51(1H, m), 3.81(1H, m), 5.34-5.46(2H, m), 6.07(1H, d, J=7.6 Hz), 7.33-7.56(5H, m). IR (CHCl₃): 3422, 3250, 3010, 2950, 2876, 2664, 2558, 2210, 1735(sh), 1705, 1645, 1502, 1441, 1410, 1307, 1276/cm. [α]_D=−63.6±1.9° (CHCl₃, c=0.56, 22° C.).

[0607] No.1k-6

[0608] CDCl₃300 MHz; 1.04-2.24(14H, m), 2.36(2H, t, J=7.5 Hz), 2.58(1H, m), 3.88(1H, m), 5.30-5.43(2H, m), 6.21(1H, d, J=7.2 Hz), 7.41-7.49(3H, m), 7.73-7.77(2H, m). IR (CHCl₃): 3447, 3011, 2955, 1708, 1653, 1603, 1578, 1515, 1486, 1457, 1312, 1211, 1164/cm. [α]_D=−60.3° (CHCl₃, c=1.00, 23° C.).

[0609] No.1k-7

[0610] CDCl₃300 MHz; 1.04-2.22(14H, m), 2.36(2H, t, J=7.2 Hz), 2.57(1H, m), 3.87(1H, m), 5.30-5.44(2H, m), 6.17(1H, d, J=8.7 Hz), 6.99-7.40(7H, m), 7.73(2H, d, J=7.5 Hz). IR (CHCl₃): 3449, 3013, 2955, 1739, 1708, 1651, 1609, 1588, 1522, 1487, 1243, 1227, 1169/cm. [α]_D=−60.2° (CHCl₃, c=0.92, 23° C.).

[0611] No.1k-8

[0612] CDCl₃300 MHz; 1.04-2.25(14H, m), 2.34(2H, t, J=7.5 Hz), 2.56(1H, m), 3.87(1H, m), 5.30-5.44(2H, m), 6.19(1H, d, J=7.5 Hz), 6.83-6.94(6H, m), 7.69(2H, d, J=8.7 Hz). IR (CHCl₃): 3599, 3455, 3012, 2955, 1711, 1644, 1604, 1577, 1524, 1507, 1492, 1290, 1236, 1197, 1170/cm. [α]_D=−47.7° (CHCl₃, c=1.01, 22° C.).

[0613] No.1k-9

[0614] CDCl₃300 MHz; 1.04-2.20(14H, m), 2.31(3H, s), 2.36(2H, t, J=7.2 Hz), 2.56(1H, m), 3.86(1H, m), 5.30-5.43(2H, m), 6.16(1H, d, J=7.2 Hz), 7.00-7.11(6H, m), 7.74(2H, d, J=8.7 Hz). IR (CHCl₃): 3450, 3010, 2955, 1750, 1709, 1651, 1609, 1596, 1523, 1489, 1370, 1247, 1227, 1183/cm. [α]_D=−54.7° (CHCl₃, c=1.01, 22° C.).

[0615] No.1k-10

[0616] CDCl₃300 MHz; 1.04-2.22(14H, m), 2.35(2H, t, J=7.2 Hz), 2.56(1H, m), 3.82(3H, s), 3.86(1H, m), 5.30-5.43(2H, m), 6.17(1H, d, J=6.9 Hz), 6.89-7.01(6H, m), 7.70(2H, d, J=8.7 Hz). IR (CHCl₃): 3023, 2955, 1742, 1708, 1649, 1613, 1602, 1577, 1522, 1507, 1490, 1227, 1210, 1170/cm. [α]_D=−58.1° (CHCl₃, c=1.01, 22° C.).

[0617] No.1m-1

[0618] CDCl₃300 MHz; 1.06-2.25(14H, m), 2.32(2H, t, J=7.4 Hz), 2.61(1H, m), 3.63(3H, s), 3.91(1H, m), 5.33-5.47(2H, m), 6.24(1H, d, J=6.9 Hz), 7.35-7.38(3H, m), 7.53-7.60(4H, m), 7.78(2H, m). IR (CHCl₃): 3438, 3008, 2946, 2875, 2212, 1732, 1650, 1605, 1519, 1496/cm. [α]_D=+76° (CHCl₃, c=1.39, 24° C.).

[0619] No.1m-2

[0620] CDCl₃300 MHz; 1.05-2.20(14H, m), 2.36(2H, t, J=6.2 Hz), 2.59(1H, m), 3.89(1H, m), 5.29-5.48(2H, m), 6.26(1H, d, J=7.0 Hz), 7.26-7.38(3H, m), 7.52-7.60(4H, m), 7.73-7.77(2H, m). IR (CHCl₃): 3444, 3012, 2952, 2874, 2664, 2214, 1718(sh), 1708, 1649, 1605, 1520, 1498/cm. [α]_D=+81.4° (CHCl₃, c=1.01, 23° C.).

[0621] No.1m-3

[0622] CDCl₃300 MHz; 1.06-2.23(14H, m), 2.32(2H, t, J=7.0 Hz), 2.62(1H, m), 3.63(3H, s), 3.93(1H, m), 5.30-5.50(2H, m), 6.28(1H, d, J=7.0 Hz), 7.38-7.51(3H, m), 7.58-7.67(4H, m), 7.88(2H, m). IR (CHCl₃): 3438, 3008, 2948, 2875, 1783(w), 1727, 1650, 1608, 1580(w), 1523, 1501, 1482/cm. [α]_D=+59° (CHCl₃, c=1.49, 25° C.).

[0623] No.1m-4

[0624] CDCl₃300 MHz; 1.08-2.25(14H, m), 2.36(2H, t, J=7.4 Hz), 2.59(1H, m), 3.91(1H, m), 5.28-5.48(3H, m), 6.29(1H, d, J=7.4 Hz), 7.38-7.50(3H, m), 7.61-7.67(4H, m), 7.81-7.86(2H, m). IR (CHCl₃): 3436, 3010, 2948, 2868, 1727, 1715(sh), 1649, 1615(w), 1524, 1502, 1482, 1372/cm. [α]_D=+72° (CHCl₃, c=0.98, 25° C.).

[0625] No.1m-5

[0626] CDCl₃300 MHz; 1.09-2.20(14H, m), 2.32(2H, t, J=7.2 Hz), 2.63(1H, m), 3.63(3H, s), 3.92(1H, m), 5.31-5.51(2H, m), 6.35(1H, d, J=7.0 Hz), 7.51-7.60(3H, m), 7.92-7.97(6H, m). IR (CHCl₃): 3436, 3008, 2946, 2875, 1727, 1652, 1608(w), 1515, 1484/cm. [α]_D=+82° (CHCl₃, c=0.99, 25° C.).

[0627] No.1m-6

[0628] CDCl₃300 MHz; 1.09-2.23(14H, m), 2.37(2H, t, J=7.2 Hz), 2.60(1H, m), 3.92(1H, m), 5.30-5.49(2H, m), 6.32(1H, d, J=7.4 Hz), 7.51-7.55(3H, m), 7.85-7.98(6H, m). IR (CHCl₃): 3436, 3010, 2950, 2875, 2670, 1727, 1715(sh), 1650, 1605(w), 1515, 1484/cm. [α]_D=+84° (CHCl₃, c=1.54, 25° C.).

[0629] No.1m-7

[0630] CDCl₃300 MHz; 1.03-2.18(14H, m), 2.32(2H, t, J=7.4 Hz), 2.59(1H, m), 3.64(3H, s), 3.89(1H, m), 5.29-5.49(2H, m), 6.16(1H, d, J=7.8 Hz), 6.98-7.06(4H, m), 7.14-7.20(1H, m), 7.34-7.41(2H, m), 7.73-7.78(2H, m). IR (CHCl₃): 3438, 3008, 2946, 2868, 1727, 1648, 1610, 1586, 1519, 1485/cm. [α]_D=+54° (CHCl₃, c=1.29, 25° C.).

[0631] No.1m-8

[0632] CDCl₃300 MHz; 1.06-2.21(14H, m), 2.36(2H, t, J=7.5 Hz), 2.58(1H, m), 3.88(1H, m), 5.31-5.46(2H, m), 6.17(1H, d, J=6.9 Hz), 6.99-7.05(4H, m), 7.15-7.21(H, m), 7.36-7.41(2H, m), 7.72-7.75(2H, m). IR (CHCl₃): 3436, 3010, 2948, 2868, 2675, 1730(sh), 1709, 1647, 1608, 1586, 1520, 1485/cm. [α]_D=+56° (CHCl₃, c=0.97, 25° C.).

[0633] No.1m-9

[0634] CDCl₃300 MHz; 1.05-2.18(14H, m), 2.29-2.34(5H, m), 2.59(1H, m), 3.64(3H, s), 3.89(1H, m), 5.32-5.46(2H, m), 6.16(1H, d, J=7.5 Hz), 7.00-7.11(6H, m), 7.74-7.77(2H, m). IR (CHCl₃): 3440, 3010, 2946, 2868, 1729, 1649, 1595, 1519, 1488/cm. [α]_D=+47° (CHCl₃, c=0.82, 25°C.).

[0635] No.1m-10

[0636] CDCl₃300 MHz; 1.04-2.20(14H, m), 2.31-2.39(5H, m), 2.57(1H, m), 3.87(1H, m), 5.28-5.47(2H, m), 6.17(1H, d, J=7.0 Hz), 6.99-7.12(6H, m), 7.72-7.76(2H, m). IR (CHCl₃): 3674, 3572, 3438, 3010, 2948, 2868, 2626, 1748, 1710, 1648, 1615, 1520, 1489/cm. [α]_D=+51° (CHCl₃, c=0.91, 25° C.).

[0637] No.1m-11

[0638] CDCl₃300 MHz; 10 1.04-2.16(14H, m), 2.31(2H, t, J=7.2 Hz), 2.59(1H, m), 3.63(1H, m), 5.29-5.49(2H, m), 6.24(H, d, J=7.4 Hz), 6.54(H, s), 6.83-6.93(6H, m), 7.69-7.73(2H, m). IR (CHCl₃): 3674, 3588, 3438, 3296, 3010, 2946, 2868, 1725, 1646, 1603, 1520, 1504, 1489/cm. [α]_D=+51° (CHCl₃, c=0.91, 25° C.).

[0639] No.1m-12

[0640] CDCl₃300 MHz; 1.04-2.21(14H, m), 2.33(2H, t, J=8.0 Hz), 2.56(1H, m), 3.87(1H, m), 5.28-5.48(2H, m), 6.23(1H, d, J=8.0 Hz), 6.75(1H, m), 6.87-6.94(6H, m), 7.66-7.71(2H, m), 9.63(1H, brs). IR (CHCl₃): 3674, 3582, 3436, 3275, 3010, 2950, 2868, 2675, 1727, 1710(sh), 1643, 1603, 1522, 1504, 1490/cm. [α]_D=+30° (CHCl₃, c=0.97, 25° C.).

[0641] No.1m-13

[0642] CDCl₃300 MHz; 1.01-2.18(14H, m), 2.31(2H, t, J=7.4 Hz), 2.58(1H, m), 3.63(3H, s), 3.82(3H, s), 3.89(1H, m), 5.29-5.48(2H, m), 6.14(1H, d, J=7.0 Hz), 6.88-7.02(6H, m), 7.70-7.74(2H, m). IR (CHCl₃): 3442, 3402, 3004, 2946, 2868, 1727, 1648, 1600, 1518, 1499/cm. [α]_D=+42° (CHCl₃, c=1.82, 26° C.).

[0643] No.1m-14

[0644] CDCl₃300 MHz; 1.06-2.21(14H, m), 2.35(2H, t, J=7.2 Hz), 2.55(1H, m), 3.82(3H, s), 3.88(1H, m), 5.27-5.46(2H, m), 6.16(1H, d, J=7.2 Hz), 6.88-7.02(6H, m), 7.68-7.73(2H, m). IR (CHCl₃): 3438, 3012, 2948, 2870, 2650, 1730(sh), 1709, 1647, 1615(sh), 1601, 1519, 1492/cm. [α]_D=+64° (CHCl₃, c=0.70, 25° C.).

[0645] No.1m-15

[0646] CDCl₃300 MHz; 1.05-2.20(14H, m), 2.29-2.36(5H, m), 2.62(1H, m), 3.63(3H, s), 3.92(1H, m), 5.30-5.50(2H, m), 6.25(1H, d, J=7.2 Hz), 7.16-7.21(2H, m), 7.59-7.64(4H, m), 7.83-7.87(2H, m). IR (CHCl₃): 3446, 3010, 2946, 2868, 1745(sh), 1728, 1650, 1615, 1525, 1507, 1486/cm. [α]_D=+65.0° (CHCl₃, c=1.02, 23° C.).

[0647] No.1m-16

[0648] CDCl₃300 MHz; 1.08-2.21(14H, m), 2.34-2.40(5H, m), 2.59(1H, m), 3.90(1H, m), 5.29-5.48(2)H, m), 6.29(1H, d, J=7.0 Hz), 7.18(2H, d, J=8.6 Hz), 7.58-7.64(4H, m), 7.83(2H, d, J=8.2 Hz). IR (CHCl₃): 3438, 3012, 2948, 2870, 2622, 1749, 1710, 1649, 1610, 1526, 1508, 1487/cm. [α]_D=+66° (CHCl₃, c=1.21, 24° C.).

[0649] No.1m-17

[0650] CDCl₃300 MHz; 201.06-2.19(14H, m), 2.32(2H, t, J=7.2 Hz), 2.62(1H, m), 3.63(3H, s), 3.93(1H, m), 5.30-5.50(2H, m), 6.32(1H, d, J=7.6 Hz), 6.41(1H, s), 6.94(2H, d, J=9.0 Hz), 7.47(2H, d, J=9.0 Hz), 7.58(2H, d, J=8.6 Hz), 7.81(2H, d, J=8.6 Hz). IR (CHCl₃): 3580, 3434, 3284, 3010, 2946, 2868, 1726, 1646, 1606, 1528, 1490/cm. [α]_D=+62.4° (CHCl₃, c=1.01, 23° C.).

[0651] No.1m-18

[0652] CDCl₃+CH₃OD 300 MHz; 1.11-2.18(14H, m), 2.32(2H, t, J=7.4 Hz), 2.59(1H, m), 3.88(1H, m), 5.30-5.49(2H, m), 6.55(1H, d, J=7.0 Hz), 6.92(2H, d, J=8.6 Hz), 7.47(2H, d, J=8.6 Hz), 7.59(2H, d, J=8.6 Hz), 7.79(2H, d, J=8.2 Hz). IR (Nujol): 3398, 3175, 2725, 1696, 1635, 1601, 1531, 1510/cm. [α]_D=+99.5° (CH₃OH, c=1.011, 25° C.).

[0653] No.1m-19

[0654] CDCl₃300 MHz; 1.05-2.20(14H, m), 2.32(2H, t, J=7.4 Hz), 2.61(1H, m), 3.63(3H, s), 3.83(3H, s), 3.94(1H, m), 5.30-5.50(2H, m), 6.24(1H, d, J=7.0 Hz), 6.99(2H, d, J=8.6 Hz), 7.63-7.63(4H, m), 7.82(2H, d, J=8.6 Hz). IR (CHCl₃): 3440, 3006, 2946, 2875, 1726, 1649, 1606, 1527, 1510, 1489/cm. [α]_D=+68° (CHCl₃, c=0.88, 26° C.).

[0655] No.2m-20

[0656] CDCl₃300 MHz; 1.09-2.20(14H, m), 2.35(2H, t, J=7.3 Hz), 2.58(1H, m), 3.85(3H, s), 3.89(1H, m) 5.28-5.48(2H, m), 6.35(1H, d, J=7.2 Hz), 6.98(2H, d, J=8.8 Hz), 7.51-7.61(4H, m), 7.81(2H, d, J=8.4 Hz), 8.34(1H, brs).

[0657] IR (CHCl₃): 3446, 3012, 2952, 2881, 2640, 1730(sh), 1707, 1647, 1606, 1527, 1510, 1489/cm. [α]_D=+83° (CHCl₃, c=1.00, 25° C.).

[0658] No.1m-21

[0659] CDCl₃300 MHz; 1.05-2.14(14H, m), 2.37(2H, t, J=7.2 Hz), 2.51(1H, m), 3.81(1H, m), 5.34-5.46)2H, m), 6.11(1H, d, J=7.5 Hz), 7.33-7.48(3H, m), 7.53-7.55(2H, m). IR (CHCl_3):3420, 3250, 3008, 2948, 2870, 2660, 2210, 1735(sh), 1705, 1645, 1503, 1441, 1409/cm. [α]_D=+59.2±1.0° (CHCl₃, c=1.023, 22° C.).

[0660] No.1m-22

[0661] CDCl₃300 MHz; 1.05-2.17(14H, m), 2.37(2H, t, J=7.2 Hz), 2.52(1H, m), 3.82(1H, m), 5.32-5.47(2H, m), 6.20(1H, d, J=7.6 Hz), 7.38-7.53(3H, m), 7.58-7.61(6H, m), 9.11(1H, brs). IR (CHCl₃): 3420, 3250, 3010, 2984, 2870, 2675, 2208, 1730(sh), 1705, 1640, 1500, 1406/cm. [α]_D=+57.4° (CHCl₃, c=1.83, 23° C.).

[0662] No.1m-23

[0663] CDCl₃300 MHz; 1.05-2.18(14H, m), 2.31(2H, t, J=7.5 Hz), 2.60(1H, m), 3.63(3H, s), 3.90(1H, m), 5.32-5.47(2H, m), 6.22(1H, d, J=6.9 Hz), 7.40-7.49(3H, m), 7.76-7.79(2H, m). IR (CHCl₃): 3438, 3008, 2946, 2868, 1727, 1651, 1603, 1585, 1521, 1484/cm. [α]_D=+52° (CHCl₃, c=1.49, 25° C.).

[0664] No.1m-24

[0665] CDCl₃300 MHz; 1.05-2.21(14H, m), 2.36(2H, t, J=7.2 Hz), 2.57(1H, m), 3.89(1H, m), 5.28-5.47(2H, m), 6.22(1H, d, J=7.0 Hz), 7.39-7.55(3H, m), 7.73-7.79(2H, m). IR (CHCl₃): 3676, 3572, 3436, 3010, 2948, 2875, 1730(sh), 1709, 1650, 1600, 1580, 1514, 1484/cm. [α]_D=+57° (CHCl₃, c=0.97, 26° C.).

[0666] No.1m-25

[0667] CDCl₃300 MHz; 1.04-2.18(14H, m), 2.28-2.35(5H, m), 2.59(1H, m), 3.62(3H, s), 3.88(1H, m), 5.29-5.49(2H, m), 6.20(1H, d, J=7.2 Hz), 7.15(2H, d, J=9.0 Hz), 7.80(2H, d, J=8.8 Hz). IR (CHCl₃): 3436, 3010, 2946, 2868, 1752, 1727, 1653, 1602, 1519, 1491/cm. [α]_D=+53° (CHCl₃, c=1.63, 25° C.).

[0668] No.1m-26

[0669] CDCl₃300 MHz; 1.05-2.19(14H, m), 2.32-2.38(5H, m), 2.56(1H, m), 3.88(1H, m), 5.29-5.47(2H, m), 6.25(1H, d, J=7.4 Hz), 7.15(2H, d, J=9.0 Hz), 7.78(2H, d, J=8.6 Hz). IR (CHCl₃): 3434, 3016, 3006, 2948, 2880, 2622, 1752, 1730(sh), 1710, 1651, 1605, 1520, 1492/cm. [α]_D=+58° (CHCl₃, c=3.68, 24° C.).

[0670] No.1m-27

[0671] CDCl₃300 MHz; 1.05-2.16(14H, m), 2.30(2H, t, J=7.5 Hz), 2.57(1H, m), 3.62(3H, s), 3.87(1H, m), 5.27-5.47(2H, m), 6.32(1H, d, J=7.4 Hz), 6.85(2H, d, J=8.6 Hz), 7.62(2H, d, J=8.6 Hz), 8.35(1H, s). IR (CHCl₃): 3580, 3450, 3216, 3010, 2946, 2868, 1726, 1640, 1608, 1584, 1528, 1496/cm. [α]_D=+56.2° (CHCl₃, c=0.713, 23° C.).

[0672] No.1m-28

[0673] CDCl₃200 MHz; 1.10-2.25(14H, m), 2.32(2H, t, J=7.2 Hz), 2.55(1H, brs), 3.82-3.93(1H, m), 5.27-5.47(2H, m), 6.25(1H, d, J=7.4 Hz), 6.86(2H, d, J=8.6 Hz), 7.62(2H, d, J=8.6 Hz). IR (CHCl₃): 3438, 3242, 2675, 1730(sh), 1708, 1639, 1607, 1585/cm.

[0674] No.1m-29

[0675] CDCl₃300 MHz; 1.05-2.18(14H, m), 2.31(2H, t, J=7.4 Hz), 2.58(1H, m), 3.64(3H, s), 3.85(3H, s), 3.89(1H, m), 5.29-5.48(2H, m), 6.14(1H, d, J=6.6 Hz), 6.92(2H, d, J=9.0 Hz), 7.74(2H, d, J=9.0 Hz). IR (CHCl₃): 3445, 3008, 2946, 2868, 1727, 1646, 1606, 1578, 1523, 1493/cm. [α]_D=+53° (CHCl₃, c=2.03, 24° C.).

[0676] No.1m-30

[0677] CDCl₃300 MHz; 1.04-2.21(14H, m), 2.36(2H, t, J=7.3 Hz), 2.56(1H, m), 3.85(3H, s), 3.88(1H, m), 5.27-5.46(2H, m), 6.15(1H, d, J=7.2 Hz), 6.92(2H, d, J=8.6 Hz), 7.73(2H, d, J=8.6 Hz). IR (CHCl₃): 3440, 3010, 2950, 2870, 2645, 1727, 1710(sh), 1646, 1606, 1575, 1524, 1494/cm. [α]_D=+62° (CHCl₃, c=1.10, 24° C.).

[0678] No.1m-31

[0679] CDCl₃+CD₃OD 300 MHz; 1.16-2.20(14H, m), 2.31(2H, t, J=7.2 Hz), 2.59(1H, m), 3.85(1H, m), 5.31-5.51(2H, m), 7.13-7.21(1H, m), 7.31-7.42(2H, m), 7.68-7.93(6H, m). IR (Nujol): 3344, 3175, 2715, 2675, 1699, 1631, 1566/cm. [α]_D=+67° (CH₃OH, c=1.01, 24° C.).

[0680] No.1m-32

[0681] CDCl₃200 MHz; 1.09-2.23(14H, m), 2.33(2H, t, J=7.1 Hz), 2.57(1H, brs), 3.40-3.93(9H, m), 4.41(1H, brs), 5.29-5.48(2H, m), 6.44(1H, d, J=7.4 Hz), 7.43(2H, d, J=8.2 Hz), 7.80(2H, d, J=7.8 Hz). IR (CHCl₃): 3434, 3354, 1726, 1720(sh), 1660(sh), 1626/cm.

[0682] No.1m-33

[0683] CDCl₃200 MHz; 1.14-2.25(14H, m), 2.37(2H, t, J=7.3 Hz), 2.64(1H, brs), 3.93-4.01(1H, m), 5.30-5.51(2H, m), 6.47(1H, d, J=7.4 Hz), 7.63-7.74(2H, m), 7.79(2H, s), 7.89-7.93(1H, m), 8.00(1H, dd, J=2.3, 1.0 Hz), 8.30(1H, d, J=1.0 Hz), 8.65-8.73(2H, m). IR (CHCl₃): 3450, 2675, 1728, 1707, 1649, 1528, 1509/cm. [α]_D=+82.8±1.2° (CHCl₃, c=1.01, 23° C.).

[0684] No.2a-1

[0685] [α]_D=+69.0° (MeOH, c=1.01, 25° C.)

[0686] No.2a-2

[0687] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.15 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 4.30(1H, m), 5.35-5.52(2H, m), 6.32(1H, d, J=8.7 Hz), 7.36-7.49(3H, m), 7.58-7.62(2H, m), 7.66 and 7.80(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3116, 3014, 2925, 2870, 2663, 1708, 1651, 1610, 1524, 1504, 1484, 1472/cm. [α]_D=+64.1° (MeOH, c=1.02, 25° C.).

[0688] No.2a-3

[0689] [α]_D=+76.6° (MeOH, c=1.18, 26° C.).

[0690] No.2a-4

[0691] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.15 and 1.25(each 3H, each s), 1.64-2.51(14H, m), 4.31(1H, m), 5.36-5.53(2H, m), 6.33(1H, d, J=8.4z), 7.50-7.56(3H, m), 7.85-7.98(6H, m). IR (CHCl₃): 3515, 3452, 3014, 2925, 2870, 1740, 1708, 1654, 1517, 1486, 1470/cm. [α]_D=+79.5° (MeOH, c=1.18, 22° C.).

[0692] No.2a-5

[0693] CD₃OD 300 MHz; 0.98(1H, d, J=9.9 Hz), 1.18 and 1.25(each 3H, each s), 1.56-1.71(3H, m), 1.98-2.40(11H, m), 4.17(1H, m), 5.41-5.52(2H, m), 7.52-7.61(3H, m), 7.91-8.01(6H, m). IR (KBr): 3416, 3063, 2983, 2921, 2869, 1704, 1643, 1566, 1518, 1488, 1408/cm. [α]_D=+62.0° (MeOH, c=1.00, 25° C.).

[0694] No.2a-6

[0695] [α]_D=+64.1° (MeOH, c=1.01, 25° C.).

[0696] No.2a-7

[0697] [α]_D=+65.3° (MeOH, c=0.99, 25° C.).

[0698] No.2a-8

[0699] [α]_D=+74.0° (MeOH, c=1.01, 25° C.).

[0700] No.2a-9 [α]_D=+71.0° (MeOH, c=1.10, 25° C.).

[0701] No.2a-10 [α]_D=+74.7° (MeOH, c=1.00, 25° C.).

[0702] No.2a-11

[0703] [α]_D=+72.1° (MeOH, c=1.00, 25° C.).

[0704] No.2a-12

[0705] [α]_D=+53.1° (CHCl₃, c=1.01, 26° C.). m.p. 155.0-156.0° C.

[0706] No.2a-13

[0707] CDCl₁300 MHz; 0.98(1H, d, J=10.2 Hz), 1.18 and 1.25(each 3H, each s), 1.63-2.40(14H, m), 4.30(1H, m), 5.46-5.58(2H, m), 6.44(1H, d, J=8.4 Hz), 7.49 and 7.77(each 2H, each d, J=8.7 Hz), 7.54(1H, s). IR (CHCl₃): 3689, 3378, 3028, 3014, 2924, 1713, 1652, 1602, 1522, 1496/cm. [α]_D=+78.3° (MeOH, c=0.84, 25° C.). m.p. 205.0-206.0° C.

[0708] No.2a-14 [α]_D=+72.5° (MeOH, c=1.07, 25° C.).

[0709] No.2a-15

[0710] CDCl₃300 MHz; 0.99(1H, d, J=9.9 Hz), 1.14 and 1.24(each 3H, each s), 1.55-2.44(14H, m), 4.27(1H, m), 5.30-5.50(2H, m), 6.29(1H, d, J=9.0 Hz), 7.11 and 7.20(each 1H, each d, J=16.2 Hz), 7.29-7.55(5H, m), 7.57 and 7.72(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3453, 3083, 3022, 3013, 2925, 2870, 1708, 1650, 1607, 1560, 1522, 1496/cm. [α]_D=+72.3° (MeOH, c=1.00, 27° C.). m.p. 115.0-117.0° C.

[0711] No.2a-16

[0712] CDCl₃300 MHz; 0.92(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.48(14H, m), 3.62(3H, s), 4.29(1H, m), 5.30-5.50(2H, m), 6.20(1H, d, J=8.7 Hz), 6.59 and 6.68(each 1H, each, d, J=12.3 Hz), 7.23(5H, s), 7.29 and 7.59(each 2H, each d, J=8.1 Hz). IR (CHCl₃): 3453, 3024, 3016, 2924, 2870, 1730, 1651, 1607, 1520, 1495/cm. [α]_D=+56.8° (MeOH, c=1.04, 24° C.).

[0713] No.2a-17

[0714] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.38(14H, m), 4.26(1H, m), 5.30-5.50(2H, m), 6.23(1H, d, J=8.4 Hz), 6.59 and 6.70(each 1H, each d, J=12.3 Hz), 7.23(5H, s), 7.30 and 7.57(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3452, 3081, 3019, 3014, 2925, 2870, 2665, 1708, 1650, 1607, 1521, 1495/cm. [α]_D=+61.6° (MeOH, c=1.00, 27° C.).

[0715] No.2a-18

[0716] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each, s), 1.50-2.50(14H, m), 3.61(3H, s), 4.31(1H, m), 5.35-5.51(2H, m), 6.33(1H, d, J=8.4 Hz), 7.48-7.64(4H, m), 7.79-7.83(2H, m), 7.91(1H, dt, J=1.5 and 7.8 Hz), 8.01(1H, dt, J=1.5 and 7.8 Hz), 8.13(1H, t, J=1.5 Hz). IR (CHCl₃): 3450, 3026, 3013, 2925, 2870, 1730, 1659, 1600, 1510/cm. [α]_D=+56.0° (MeOH, c=1.01, 25° C.).

[0717] No.2a-19

[0718] CDCl₃300 MHz; 0.95(1H, d, J=9.9 Hz), 1.14 and 1.21(each 3H, each s), 1.53-2.60(14H, m), 4.25(1H, m), 5.35-5.64(2H, m), 7.21(1H, d, J=7.8 Hz), 7.49-7.68(4H, m), 7.76-7.84(3H, m), 8.25(1H, m), 8.43(1H, m). IR (CHCl₃): 3382, 3196, 3025, 3015, 2925, 2870, 1725, 1652, 1599, 1577, 1521/cm. [α]_D=+55.9° (MeOH, c=1.00, 25° C.).

[0719] No.2a-20

[0720] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.13 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 3.62(3H, s), 4.31(1H, m), 5.35-5.51(2H, m), 6.24(1H, d, J=8.4 Hz), 7.40-7.52(3H, m), 7.71-7.76(2H, m). IR (CHCl₃): 3453, 3025, 3013, 2925, 2870, 1730, 1753, 1579, 1514, 1486/cm. [α]_D=+61.2° (MeOH, c=1.04, 25° C.).

[0721] No.2a-21

[0722] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.13 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.28(1H, m), 5.34-5.51(2H, m), 6.27(1H, d, J=8.7 Hz), 7.41-7.53(3H, m), 7.71-7.74(2H, m). IR (CHCl₃): 3452, 3063, 3027, 3014, 2925, 2871, 1708, 1652, 1578, 1515, 1486/cm. [α]_D=+62.0° (MeOH, c=1.01, 27° C.).

[0723] No.2a-22

[0724] d₆-DMSO 300 MHz; 0.86(1H, d, J=9.9 Hz), 1.10 and 1.16(each 3H, each s), 1.42-1.52(3H, m), 1.85-2.46(11H, m), 3.98(1H, m), 5.32-5.43(2H, m), 7.41(3H, m), 7.88(2H, d, J=6.6 Hz), 8.19(1H, d, J=6.6 Hz). IR (KBr): 3367, 3060, 2984, 2922, 2868, 1634, 1563, 1529, 1487/cm. [α]_D=+47.7(MeOH, c=1.00, 25°C.).

[0725] No.2a-23

[0726] [α]_D=+62.7° (MeOH, c=1.01, 27° C.).

[0727] No.2a-24

[0728] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.14 and 1.25(each 3H, each s), 1.52-2.50(14H, m), 4.31(1H, m), 5.36-5.52(2H, m), 6.34(1H, d, J=8.4 Hz), 7.47-7.52(2H, m), 7.59-7.64(1H, m), 7.78-7.83(6H, m). IR (CHCl₃): 3449, 3027, 3013, 2925, 2869, 1708, 1656, 1599, 1518, 1493/cm. [α]_D=+63.1° (MeOH, c=1.00, 25° C.).

[0729] No.2a-25

[0730] [α]_D=+35.1° (MeOH, c=1.00, 25° C.).

[0731] No.2a-26

[0732] [α]_D=+35.5° (MeOH, c=1.02, 25° C.).

[0733] No.2a-27

[0734] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 3.63(3H, s), 4.29(1H, m), 5.36-5.51(2H, m), 6.18(1H, d, J=8.4 Hz), 7.01 and 7.71 (each 2H, each d, J=8.7 Hz, ), 6.98-7.05(2H, m), 7.16(1H, t, J=7.5 Hz), 7.34-7.41(2H, m). IR (CHCl₃): 3455, 3024, 3016, 2924, 2870, 1730, 1651, 1588, 1520, 1487/cm. [α]_D=+56.4° (MeOH, c=1.01, 25° C.).

[0735] No.2a-28

[0736] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.26(1H, m), 5.34-5.51(2H, m), 6.20(1H, d, J=9.0 Hz), 7.01 and 7.70(each 2H, each d, J=9.0 Hz,), 6.98-7.15(2H, m), 7.17(1H, t, J=7.5 Hz), 7.34-7.40(2H, m). IR (CHCl₃): 3454, 3031, 3018, 2925, 2870, 1708, 1650, 1588, 1523, 1487/cm. [α]_D=+56.2° (MeOH, c=1.00, 25°C.).

[0737] No.2a-29

[0738] [α]_D=+53.0° (MeOH, c=1.03, 25° C.).

[0739] No.2a-30

[0740] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.10 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.25(1H, m), 5.30-5.50(2H, m), 6.23(1H, d, J=8.7 Hz), 6.36(1H, s), 7.26-7.39(10H, m), 7.60 and 7.68(each 2H, each d, J=8.4 Hz,). IR (CHCl₃): 3451, 3088, 3064, 3029, 3014, 2925, 2869, 1707, 1652, 1522, 1495/cm. [α]_D=+54.2° (MeOH, c=1.00, 25° C.).

[0741] No.2a-31

[0742] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 3.63(3H, s), 4.31(1H, m), 5.30-5.50(2H, m), 6.26(1H, d, J=8.4 Hz), 6.90(1H, t, J=7.4 Hz), 7.13(1H, d, J=8.7 Hz), 7.29(2H, t, J=8.0 Hz), 7.67-7.75(5H, m), 7.82(1H, s). IR (Nujol): 3380, 3244, 1723, 1638, 1601, 1578, 1535, 1495/cm. [α]_D=+73.6° (MeOH, c=0.50, 26° C.). m.p. 133.0-134.0° C.

[0743] No.2a-32

[0744] [α]_D=+56.1° (MeOH, c=1.02, 26° C.).

[0745] No.2a-33

[0746] CDCl₃300 MHz; 0.95(1H, d, J=10.2 Hz), 1.10 and 1.21(each, 3H, each s), 1.50-2.50(14H, m), 4.25(1H, m), 5.13(2H, s), 5.30-5.70(3H, m), 6.41(1H, d, J=8.2 Hz), 6.89(1H, s), 7.09(1H, s), 7.17 and 7.72(each 2H, each d, J=8.2 Hz), 7.62(1H, s). IR (CHCl₃): 3450, 3125, 3031, 3013, 2925, 2870, 2467, 1917, 1708, 1654, 1615, 1575, 1523, 1497/cm. [α]_D=+55.2° (MeOH, c=1.01, 26° C.).

[0747] No.2a-34

[0748] [α]_D=+72.9° (MeOH, c=1.03, 25° C.).

[0749] No.2a-35

[0750] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.13 and 1.24(each 3H, each s), 1.52-2.48(14H, m), 4.28(1H, m), 5.35-5.51(2H, m), 6.28(1H, d, J=8.7 Hz), 7.34-7.37(3H, m), 7.52-7.55(2H, m), 7.58 and 7.71(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3515, 3452, 3030, 3012, 2925, 2870, 1739, 1708, 1652, 1607, 1555, 1521, 1497/cm. [a]_D=+74.3° (MeOH, c=1.01, 25° C.).

[0751] No.2a-36 [a]_D=+23.4(MeOH, c=1.07, 25° C.).

[0752] No.2a-37

[0753] CDCl₃300 MHz; 0.83(1H, d, J=10.5 Hz), 0.95 and 1.18(each 3H, each s), 1.44-2.46(14H, m), 3.92(1H, m), 5.34-5.52(3H, m), 7.26-7.54(9H, m), 7.62(1H, s). IR (CHCl₃): 3432, 3310, 3189, 3023, 3014, 2924, 2870, 1704, 1610, 1594, 1523, 1487/cm. [α]_D=+25.3° (MeOH, c=1.00, 26° C.).

[0754] No.2a-38

[0755] [α]_D=+70.9° (MeOH, c=1.02, 25° C.).

[0756] No.2a-39

[0757] [α]_D=+70.6° (MeOH, c=1.01, 25° C.).

[0758] No.2a-40

[0759] [α]_D=+74.7° (MeOH, c=1.00, 25° C.).

[0760] No.2a-41

[0761] [α]_D=+72.1° (MeOH, c=1.01, 24° C.).

[0762] No.2a-42

[0763] [α]_D=+69.2° (MeOH, c=1.00, 25° C.).

[0764] No.2a-43

[0765] [α]_D=+70.8° (MeOH, c=1.00, 25° C.).

[0766] No.2a-44

[0767] a]_D=+60.4° (MeOH, c=1.00, 26° C.).

[0768] No.2a-45

[0769] CDCl₃300 MHz; 0.97(1H, d, J=9.9 Hz), 1.13 and 1.23(each 3H, each s), 1.55-2.52(14H, m), 4.29(1H, m), 5.34-5.54(2H, m), 6.33(1H, d, J=9.0 Hz), 7.10(1H, t, J=7.4 Hz), 7.34(2H, t, J=7.4 Hz), 7.52(2H, m), 7.68 and 7.75(each 2H, each d, J=8.4 Hz), 7.80(1H, s), 8.10(1H, s), 10.09(1H, s). IR (CHCl₃): 3393, 3195, 3093, 3033, 3013, 2925, 2870, 1698, 1656, 1598, 1537, 1498/cm. [α]_D=+59.4° (MeOH, c=1.01, 24° C.).

[0770] No.2a-46

[0771] [α]_D=+63.5° (MeOH, c=1.00, 25° C.).

[0772] No.2a-47

[0773] CDCl₃300 MHz; 0.97(1H, d, J=9.9 Hz), 1.12 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 4.29(1H, m), 5.35-5.52(2H, m), 6.32(1H, d, J=8.7 Hz), 7.26(1H, m), 7.41(2H, t, J=7.8 Hz), 7.64(2H, d, J=7.5 Hz), 7.73 and 7.77(each 2H, each d, J=8.4 Hz), 7.95(1H, s), 9.20(1H, s), 10.38(1H, s). IR (CHCl₃): 3450, 3339, 3003, 2992, 2925, 2870, 1706, 1653, 1596, 1523, 1495/cm. [α]_D=+63.3(MeOH, c=1.00, 25° C.).

[0774] No.2a-48 [α]_D=+63.8° (MeOH, c=1.00, 24° C.).

[0775] No.2a-49

[0776] CDCl₃300 MHz; 1.00(1H, d, J=10.5 Hz), 1.17 and 1.26(each 3H, each s), 1.55-2.52(14H, m), 4.34(1H, m), 5.36-5.54(2H, m), 6.35(1H, d, J=9.0 Hz), 7.50-7.62(3H, m), 7.90 and 3(each 2H, each d, J=8.4 Hz), 8.21(2H, m). IR (CHCl₃): 3451, 3029, 3022, 3016, 2925, 2870, 1708, 1655, 1542, 1508, 1498, 1471, 1459/cm. [α]_D=+63.5° (MeOH, c=1.02, 250° C.). m.p. 135.0-137.0° C.

[0777] No.2a-50

[0778] [α]_D=+68.9° (MeOH, c=1.02, 24° C.).

[0779] No.2a-51

[0780] d₆-DMSO 300 MHz; 0.87(1H, d, J=9.9 Hz), 1.10 and 1.17(each 3H, each s), 1.40-1.60(3H, m), 1.90-2.40(11H, m), 3.98(1H, m), 5.35-5.46(2H, m), 7.64(1H, s), 7.65 and 7.91(each 2H, each d, J=8.7 Hz), 8.06(1H, d, J=6.0 Hz), 9.32(1H, brs). IR (KBr): 3385, 2962, 1734, 1707, 1632, 1529, 1498/cm. [α]_D=+68.4° (MeOH, c=1.01, 24° C.).

[0781] No.2a-52

[0782] [α]_D=+76.2° (MeOH, c=1.01, 24° C.).

[0783] No.2a-53

[0784] [α]_D=+73.9° (MeOH, c=1.02, 24° C.).

[0785] No.2a-54

[0786] [α]_D=+68.1° (MeOH, c=1.00, 24° C.).

[0787] No.2a-55 [α]_D=+67.8° (MeOH, c=1.00, 24° C.).

[0788] No.2a-56

[0789] [α]_D=+65.4° (MeOH, c=1.03, 25° C.).

[0790] No.2a-57

[0791] [α]_D=+63.4° (MeOH, c=1.01, 24° C.).

[0792] No.2a-58

[0793] [α]_D=+66.6° (MeOH, c=1.01, 24° C.).

[0794] No.2a-59

[0795] [α]_D=+65.5° (MeOH, c=1.00, 24° C.).

[0796] No.2a-60

[0797] [α]_D=+60.9° (MeOH, c=1.02, 25° C.).

[0798] No.2a-61

[0799] CDCl₃300 MHz; 0.97(1H, d, J=10.0 Hz), 1.10 and 1.22(each 3H, each s), 1.50-2.50(14H, m), 4.26(1H, m), 5.30-5.54(2H, m), 6.28(1H, d, J=8.6 Hz), 6.60 and 6.82(each 1H, each d, J=12.4 Hz, ), 7.12(2H, d, J=6.0 Hz), 7.25 and 7.62(each 2H, each d, J=8.6 Hz), 8.47(2H, d, J=6.0 Hz). IR (CHCl₃): 3452, 3027, 3019, 3013, 2925, 2870, 2480, 1708, 1651, 1606, 1520, 1494/cm. [α]_D=+61.6° (MeOH, c=1.01, 25° C.).

[0800] No.2a-62

[0801] [α]_D=+72.0° (MeOH, c=0.93, 25° C.).

[0802] No.2a-63

[0803] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 4.29(1H, m), 5.36-5.55(2H, m), 6.35(1H, d, J=9.1 Hz), 7.04 and 7.27(each 1H, each d, J=16.5 Hz), 7.37(2H, d, J=6.6 Hz), 7.56 and 7.76(each 2H, each d, J=8.4 Hz), 8.57(2H, d, J=6.6 Hz). IR (CHCl₃): 3452, 3024, 3018, 3014, 2925, 2870, 2470, 1933, 1708, 1652, 1605, 1521, 1496/cm. [α]_D=+69.2° (MeOH, c=1.01, 25° C.).

[0804] No.2a-64 [α]_D=+5^6.9(MeOH, c=1.24, 25° C.).

[0805] No.2a-65

[0806] CDCl₃300 MHz; 0.98(1H, d, J=10.5 Hz), 1.12 and 1.23(each 3H, each s), 1.54-2.46(14H, m), 4.27(1H, m), 5.23(2H, s), 5.34-5.52(2H, m), 6.26(1H, d, J=8.4 Hz), 7.32-7.45(5H, m), 7.64 and 7.71(each 2H, each d, J=8.4 Hz), 8.15(1H, s). IR (CHCl₃): 3452, 3088, 3065, 3032, 3013, 2925, 2870, 1708, 1653, 1611, 1559, 1522, 1496/cm. [α]_D=+61.0° (MeOH, c=0.91, 25° C.).

[0807] No.2a-66

[0808] [α]_D=+76.0° (MeOH, c=1.01, 25° C.).

[0809] No.2a-67

[0810] CDCl₃300 MHz; 0.98(1H, d, J=10.4 Hz), 1.14 and 1.24(each 3H, each s), 1.54-2.46(14H, m), 4.28(1H, m), 5.32-5.53(2H, m), 6.27(1H, d, J=8.6 Hz), 6,92-7.31(each 1H, each d, J=16.4 Hz), 7.02(1H, dd, J=5.8 and 3.6 Hz), 7.12(1H, d, J=3.6 Hz), 7.24(1H, d, J=5.8 Hz), 7.51 and 7.70(each 2H, each d, J=8.4 Hz). IR (CHCl₃): 3453, 3029, 3013, 2925, 2870, 1739, 1650, 1604, 1524, 1515, 1494/cm. [α]_D=+76.2° (MeOH, c=1.00, 24° C.). m.p. 104.0-106.0° C.

[0811] No.2a-68

[0812] [α]_D=+5^7.7° (MeOH, c=1.01, 25° C.).

[0813] No.2a-69

[0814] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.54-2.48(14H, m), 4.28(1H, m), 5.34-5.53(2H, m), 6.29(1H, d, J=9.0 Hz), 6,54-6.74(each 1H, each d, J=12.0 Hz), 7.02(1H, dd, J=4.8 and 3.3 Hz), 6.97(1H, dd, J=3.3 and 1.2 Hz), 7.13(1H, dd, J=4.8 and 1.2 Hz), 7.44 and 7.70(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3453, 3025, 3010, 2925, 2870, 1708, 1650, 1607, 1559, 1523, 1493/cm. [α]_D=+58.4° (MeOH, c=1.00, 25° C.).

[0815] No.2a-70

[0816] [α]_D=+48.6° (MeOH, c=1.00, 25° C.).

[0817] No.2a-71

[0818] CDCl₃300 MHz; 0.98(1Hd, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.31(3H, s), 4.26(1H, m), 5.33-5.52(2H, m), 6.20(1H, d, J=9.3 Hz), 7.02-7.11(6H, m), 7.70(2H, d, J=9.0 Hz). IR (CHCl₃): 3460, 3031, 3022, 3011, 2925, 2870, 1750, 1708, 1650, 1608, 1597, 1523, 1490/cm. [α]_D=+48.9° (MeOH, c=1.01, 25° C.).

[0819] No.2a-72

[0820] [α]_D=+51.2° (MeOH, c=1.02, 25° C.).

[0821] No.2a-73

[0822] CDCl₃300 MHz; 0.97(1H, d, J=9.9 Hz), 1.11 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 4.27(1H, m), 5.32-5.52(2H, m), 6.24(1H, d, J=9.0 Hz), 6.83-6.94(6H, m), 7.65(2H, d, J=9.0 Hz). IR (CHCl₃): 3598, 3451, 3199, 3033, 3012, 2925, 2870, 1708, 1642, 1604, 1524, 1507, 1491/cm. [α]_D=+52.2° (MeOH, c=1.01, 25°C.).

[0823] No.2a-74

[0824] [α]_D=+51.5° (MeOH, c=0.92, 250° C.).

[0825] No.2a-75

[0826] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.55-2.46(14H, m), 3.82(3H, s), 4.25(1H, m), 5.32-5.52(2H, m), 6.19(1H, d, J=8.7 Hz), 6.89-7.01(6H, m), 7.65-7.68(2H, m). IR (CHCl₃): 3450, 3025, 3008, 2925, 2870, 2837, 1741, 1649, 1612, 1521, 1505, 1490/cm. [α]_D=+51.1° (MeOH, c=1.00, 25° C.).

[0827] No.2a-76

[0828] [α]_D=+60.4° (MeOH, c=0.98, 25° C.).

[0829] No.2a-77

[0830] CDCl₃300 MHz; 0.99(1H, d, J=10.5 Hz), 1.15 and 1.24(each 3H, each s), 1.54-2.48(14H, m), 2.34(3H, s), 4.29(1H, m), 5.32-5.54(2H, m), 6.32(1H, d, J=8.4 Hz), 7.19 and 7.60 (each 2H, each d, J=8.4 Hz), 7.63 and 7.79(each 2H, each d, J=8.4 Hz). IR (CHCl₃): 3452, 302-7, 3012, 2925, 2870, 1751, 1709, 1651, 1611, 1560, 1527, 1509, 1489/cm. [α]_D=+61.2° (MeOH, c=1.00, 25° C.).

[0831] No.2a-78

[0832] [α]_D=+67.4° (MeOH, c=1.01, 25° C.).

[0833] No.2a-79

[0834] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.15 and 1.24(each 3H, each s), 1.54-2.54(14H, m), 4.31(1H, m), 5.32-5.54(2H, m), 6.36(1H, d, J=8.2 Hz), 6.93 and 7.48(each 2H, each d, J=8.6 Hz), 7.59 and 7.75(each 2H, each d, J=8.4 Hz). IR (CHCl₃): 3593, 3448, 3192, 3030, 3010, 2925, 2870, 1708, 1644, 1608, 1591, 1559, 1530, 1516, 1491/cm. [α]_D=+65.8° (MeOH, c=1.01, 25° C.).

[0835] No.2a-80

[0836] [α]_D=+66.9° (MeOH, c=1.01, 25° C.).

[0837] No.2a-81

[0838] CDCl₃300 MHz; 0.99(1H, d, J=10.5 Hz), 1.15 and 1.24(each 3H, each s), 1.54-2.48(14H, m), 3.86(3H, s), 4.29(1H, m), 5.34-5.52(2H, m), 6.20(1H, d, J=8.7 Hz), 6.99 and 7.55 (each 2H, each d, J=9.0 Hz), 7.61 and 7.77 (each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3450, 3009, 2925, 2870, 2838, 1740, 1708, 1650, 1608, 1557, 1528, 1512, 1491/cm. [a]_D=+66.2° (MeOH, c=1.01, 25° C.).

[0839] No.2a-82

[0840] [α]_D=+57.7° (MeOH, c=1.02, 24° C.).

[0841] No.2a-83

[0842] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 2.33(3H, s), 4.26(1H, m), 5.32-5.52(2H, m), 6.25(1H, d, J=8.7 Hz), 7.16 and 7.75 (each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3452, 3030, 3022, 3012, 2925, 2870, 1754, 1709, 1654, 1604, 1585, 1522, 1493/cm. [α]_D=+57.4° (MeOH, c=1.01, 24° C.).

[0843] No.2a-84

[0844] [α]_D=+57.8° (MeOH, c=1.01, 24° C.).

[0845] No.2a-85

[0846] CDCl₃300 MHz; 0.95(1H, d, J=10.2 Hz), 1.12 and 1.22(each 3H, each s), 1.54-2.48(14H, m), 4.25(1H, m), 5.32-5.52(2H, m), 6.28(1H, d, J=8.7 Hz), 6.87 and 7.57(each 2H, each d, J=9.0 Hz). IR (CHCl.): 3590, 3450, 3166, 3019, 3012, 2925, 2871, 1708, 1637, 1608, 1583, 1531, 1498/cm. [α]_D=+56.0° (MeOH, c=1.01, 24° C.).

[0847] No.2a-86 [α]_D=+59.3° (MeOH, c=1.01, 22° C.).

[0848] No.2a-87

[0849] CDCl₃300 MHz; 0.98(1H, d, J=10.0 Hz), 1.13 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 3.85(3H, s), 4.25(1H, m), 5.32-5.53(2H, m), 6.19(1H, d, J=8.8 Hz), 6.93 and 7.69 (each 2H, each d, J=9.0 Hz). IR (CHCl₃): 3450, 3030, 3017, 3012, 2925, 2870, 2840, 1740, 1708, 1647, 1606, 1575, 1525, 1496/cm. [α]_D=+58.2° (MeOH, c=0.99, 22° C.).

[0850] No.2a-88 [α]_D=+50.9° (MeOH, c=1.02, 25° C.).

[0851] No.2a-89

[0852] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.18 and 1.26(each 3H, each s), 1.56-2.48(14H, m), 4.29(1H, m), 5.36-5.54(2H, m), 7.03(1H, d, J=8.7 Hz), 7.21(1H, s), 7.43(2H, m), 7.74(1H, ddd, J=1.8, 6.9 and 8.7 Hz), 8.22(1H, dd, J=1.8 and 8.1 Hz). IR (CHCl₃): 3443, 3087, 3023, 3014, 2925, 2870, 1708, 1685, 1658, 1630, 1517, 1466/cm. [α]_D=+57.1° (MeOH, c=1.01, 22° C.). m.p. 117.0-118.0° C.

[0853] No.2a-90 [α]_D=+54.1° (MeOH, c=1.01, 22° C.).

[0854] No.2a-91

[0855] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.13 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 4.24(1H, m), 5.34-5.52(2H, m), 6.49-6.53(2H, m), 7.11(1H, dd, J=0.9 and 3.6 Hz), 7.44(1H, dd, J=0.9 and 1.8 Hz). IR (CHCl₃): 3437, 3033, 3022, 3014, 2925, 2870, 1739, 1708, 1655, 1595, 1520, 1472/cm. [α]_D=+55.0° (MeOH, c=1.00, 22° C.).

[0856] No.2a-92

[0857] [α]_D=+50.3° (MeOH, c=1.00, 22° C.).

[0858] No.2a-93

[0859] CDCl₃300 MHz; 0.95(1H, d, J=10.5 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 4.25(1H, m), 5.34-5.52(2H, m), 6.12(1H, d, J=8.7 Hz) 7.07(1H, dd, J=3.9 and 5.1 Hz), 7.45-7.48(2H, m). IR (CHCl₃): 3450, 3023, 3011, 2925, 2870, 1739, 1708, 1645, 1531, 1501, 1471/cm. [α]_D=+49.1° (MeOH, c=1.02, 24° C.).

[0860] No.2a-94

[0861] [α]_D=+51.5° (MeOH, c=1.00, 24° C.).

[0862] No.2a-95

[0863] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.11 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 4.25(1H, m), 5.34-5.56(2H, m), 6.14(1H, d, J=8.7 Hz), 7.34(2H, d, J=2.0 Hz), 7.85(1H, t, J=2.0 Hz). IR (CHCl₃): 3452, 3114, 3030, 3013 2925, 2870, 1708, 1649, 1535, 1498, 1471/cm. [α]_D=+55.5° (MeOH, c=1.00, 25° C.). m.p. 87.0-88.0° C.

[0864] No.2a-96

[0865] CD₃OD 300 MHz; 0.94(1H, d, J=10.2 Hz), 1.13 and 1.22(each 3H, each s), 1.50-1.76(3H, m), 1.94-2.39(11H, m), 4.11(1H, m), 5.39-5.49(2H, m), 7.43-7.51(2H, m), 8.05(1H, m). IR (KBr): 3369, 3084, 2985, 2921, 2868, 1630, 1566, 1538, 1503/cm. [α]_D=+38.8(MeOH, c=1.01, 22° C.).

[0866] No.2a-97

[0867] CD₃OD 300 MHz; 0.93(1H, d, J=9.9 Hz), 1.13 and 1.22(each 3H, each s), 1.48-1.58(3H, m), 1.96-2.36(11H, m), 4.10(1H, m), 5.35-5.50(2H, m), 7.42-7.51(2H, m), 8.06(1H, m). IR (KBr): 3447, 3087, 2987, 2922, 2868, 1629, 1545, 1501/cm. [α]_D=+52.9° (MeOH, c=1.01, 24° C.).

[0868] No.2a-98

[0869] [α]_D=+53.2° (MeOH, c=1.02, 23° C.).

[0870] No.2a-99

[0871] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.12 and 1.22(each 3H, each s), 1.26-2.45(24H, m), 4.25(2H, m), 5.34-5.52(2H, m), 6.18(1H, d, J=8.7 Hz), 6.91 and 7.66(each 2H, each d, J=9.0 Hz). IR (CHCl₃): 3455, 3029, 3019, 2939, 2862, 1738, 1709, 1645, 1605, 1523, 1494/cm. [α]_D=+51.4° (MeOH, c=1.00, 23° C.).

[0872] No.2a-100

[0873] [α]_D=+49.3° (MeOH, c=1.00, 24° C.).

[0874] No.2a-101

[0875] [α]_D=+51.3° (MeOH, c=1.00, 24° C.).

[0876] No.2a-102

[0877] [α]_D=+48, 8° (MeOH, c=1.01, 23° C.).

[0878] No.2a-103

[0879] CDCl₃300 MHz; 0.94(1H, d, J=10.2 Hz), 1.12 and 1.22(each 3H, each s), 1.52-2.46(14H, m), 2.48(3H, d, J=0.3 Hz), 4.20(1H, m), 5.32-5.54(2H, m), 6.46(1H, brs), 7.12(1H, d, J=Hz). IR (CHCl₃): 3415, 3144, 3029, 3011, 2926, 2871, 1708, 1671, 1598, 1538, 14564/cm. [α]_D=+49.6° (MeOH, c=1.01, 23° C.).

[0880] No.2a-104 [α]_D=+77.0° (MeOH, c=1.02, 23° C.).

[0881] No.2a-105

[0882] CDCl₃300 MHz; 93(1H, d, J=9.9 Hz), 1.09 and 1.21(each 3H, each s), 1.51-2.44(14H, m), 3.90(6H, s), 4.20(1H, m), 5.38-5.50(2H, m), 5.87(1H, d, J=9.0 Hz), 6.25 and 7.54 (each 1H, each d, J=15.6 Hz), 6.84(1H, d, J=8.1 Hz), 7.03(1H, d, J=1.8 Hz), 7.09(1H, dd, J=1.8 and 8.1 Hz). IR (CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm. [α]_D=+77.3° (MeOH, c=1.01, 23° C.).

[0883] No.2a-106

[0884] [α]_D=+67.0° (MeOH, c=1.00, 25° C.).

[0885] No.2a-107 [α]_D=+66.6° (MeOH, c=1.01, 24° C.). m.p. 168.0-170.0° C.

[0886] No.2a-108 [α]_D=+61.8(MeOH, c=1.00, 22° C.).

[0887] No.2a-109

[0888] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.10 and 1.22(each 3H, each s), 1.51-2.45(14H, m), 4.25(1H, m), 5.33-5.49(2H, m), 6.21(1H, d, J=8.7 Hz), 7.25 and 7.60(each 2H, each d, J=8.7 Hz), 7.33-7.41(5H, s). IR (CHCl₃): 3453, 3062, 3028, 3014, 2925, 2870, 1739, 1708, 1651, 1594, 1557, 1515, 1481/cm. [α]_D=+61.0° (MeOH, c=1.01, 22° C.).

[0889] No.2a-110

[0890] CD₃OD 300 MHz; 0.94(1H, d, J=9.9 Hz), 1.13 and 1.22(each 3H, each s), 1.54-2.37(14H, m), 4.12(1H, m), 5.38-5.49(2H, m), 7.25 and 7.68(each 2H, each d, J=8.7 Hz), 7.41(5H, s). IR (KBr): 3435, 3058, 2986, 2920, 2866, 1635, 1595, 1562, 1521, 1482, 1439, 1411/cm. [α]_D=+47.3° (MeOH, c=1.01, 23° C.).

[0891] No.2a-111

[0892] [α]_D=+65.6° (MeOH, c=1.01, 24° C.).

[0893] No.2a-112

[0894] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.51-2.46(14H, m), 4.27(1H, m), 5.35-5.50(2H, m), 6.22(1H, d, J=8.4 Hz), 7.40 and 7.66(each 2H, each d, J=9.0 Hz). IR (CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 15135/cm. [α]_D=+65.6° (MeOH, c=1.01, 22° C.).

[0895] No.2a-113

[0896] [α]_D=+59.6° (MeOH, c=1.00, 24° C.).

[0897] No.2a-114

[0898] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.12 and 1.24(each 3H, each s), 1.52-2.46(14H, m), 4.29(1H, m), 5.35-5.51(2H, m), 6.28(1H, d, J=8.4 Hz), 7.70 and 7.83(each 2H, each d, J=8.4 Hz). IR (CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm. [α]_D=+60.6° (MeOH, c=1.01, 22° C.).

[0899] No.2a-115 [α]_D=+59.7° (MeOH, c=0.99, 24° C.).

[0900] No.2a-116

[0901] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.39(3H, s), 4.27(1H, m), 5.33-5.51(2H, m), 6.24(1H, d, J=9.0 Hz), 7.23 and 7.62(each 2H, each d, J=8.4 Hz). IR (CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm. [α]_D=+59.7° (MeOH, c=0.99, 24° C.).

[0902] No.2a-117

[0903] [α]_D=+56.7° (MeOH, c=1.00, 23° C.).

[0904] No.2a-118

[0905] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.53-2.44(14H, m), 4.23(1H, m), 5.34-5.51(2H, m), 6.02(2H, s), 6.13(1H, d, J=8.7 Hz), 6.83(1H, dd, J=1.2 and 7.8 Hz), 7.22-7.25(2H, m). IR (CHCl₃): 3453, 3031, 3020, 3012, 2924, 2870, 1740, 1708, 1650, 1619, 1605, 1519, 1504, 1480/cm. [α]_D=+57.2° (MeOH, c=1.02, 23° C.).

[0906] No.2a-119

[0907] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.07 and 1.23(each 3H, each s), 1.51-2.44(14H, m), 2.32(3H, s), 4.26(1H, m), 5.37-5.52(2H, m), 6.40(1H, d, J=9.0 Hz), 7.09(1H, m), 7.30(1H, m), 7.46(1H, m), 7.66(1H, m). IR (CHCl₃): 3443, 3028, 3012, 2925, 2870, 1766, 1747, 1709, 1657, 1607, 1516, 1479/cm. [α]_D=+53.2° (MeOH, c=0.99, 21° C.).

[0908] No.2a-120

[0909] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.53-2.44(14H, m), 4.30(1H, m), 5.35-5.52(2H, m), 6.42(1H, d, J=8.7 Hz), 6.85(1H, m), 6.99(1H, dd, J=1.2 and 8.4 Hz), 7.27(1H, m), 7.39(1H, m). IR (CHCl₃): 3463, 3033, 3021, 3014, 2992, 2924, 2870, 1708, 1643, 1597, 1523, 1488/cm. [α]_D=+46.3° (MeOH, c=1.01, 21° C.).

[0910] No.2a-121

[0911] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.14 and 1.23(each 3H, each s), 1.47-2.47(14H, m), 3.95(3H, s), 4.31(1H, m), 5.32-5.50(2H, m), 6.98(1H, dd, J=0.9 and 8.4 Hz), 7.09(1H, ddd, J=0.9, 7.7 and 8.4 Hz), 7.45(1H, m), 8.19(1H, dd, J=2.1 and 8.1 Hz), 8.32(1 H, d, J=9.0 Hz). IR (CHCl₃): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470/cm. [α]_D=+38.1° (MeOH, c=1.02, 23° C.).

[0912] No.2a-122

[0913] [α]_D=+42.3° (MeOH, c=0.99, 23° C.).

[0914] No.2a-123

[0915] [α]_D=+38.7° (MeOH, c=1.00, 21° C.).

[0916] No.2a-124

[0917] [α]_D=+45.0° (MeOH, c=1.01, 21° C.). m.p. 119.0-120.0° C.

[0918] No.2a-125

[0919] [α]_D=+49.8° (MeOH, c=1.01, 22° C.).

[0920] No.2a-126

[0921] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.52-2.47(14H, m), 4.26(1H, m), 5.34-5.50(2H, m), 6.22(1H, d, J=8.7 Hz), 7.55-7.61(4H, m). IR (CHCl₃): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470/cm. [α]_D=+63.0(MeOH, c=1.01, 23°C.).

[0922] No.2a-127

[0923] CDCl₃300 MHz; 0.91(1H, d, J=10.2 Hz), 1.10 and 1.20(each 3H, each s), 1.50-2.42(14H, m), 4.23(1H, m), 5.31-5.51(2H, m), 6.45(1H, d, J=8.4 Hz), 7.01(1H, t, J=7.4 Hz), 7.22(2H, m), 7.33-7.40(4H, m), 7.53(2H, d, J=9.0 Hz), 8.30 and 8.48(each 1H, each s) IR (CHCl₃): 3452, 3028, 3022, 3015, 2925, 2870, 1708, 1654, 1590, 1514, 1478/cm. [α]_D=+5^9.5° (MeOH, c=1.01, 23° C.).

[0924] No.2a-128

[0925] d₆-DMSO 300 MHz; 0.84(1H, d, J=9.9 Hz), 1.06 and 1.19(each 3H, each s), 1.37-2.37(14H, m), 3.79(1H, m), 5.35-5.51(2H, m), 6.08(1H, d, J=8.7 Hz), 6.85-6.90(1H, m), 7.18-7.23(2H, m), 7.35-7.38(2H, m), 8.42(1H, s), 12.00(1H, s). IR (Nujol): 3395, 3345, 2925, 2866, 2623, 2506, 1697, 1658, 1638, 1597, 1557/cm. [α]_D=+26.0° (MeOH, c=1.01, 23° C.). m.p. 164.0-166.0° C.

[0926] No.2a-129

[0927] CDCl₃300 MHz; 1.01(1H, d, J=10.0 Hz), 1.17 and 1.25(each 3H, each s), 1.54-2.52(14H, m), 4.34(1H, m), 5.36-5.57(2H, m), 6.42(1H, d, J=8.6 Hz), 7.51-7.60(2H, m), 7.77(1H, dd, J=1.8 and 8.6 Hz), 7.85-7.96(3H, m), 8.24(1H, brs). IR (CHCl₃): 3451, 3060, 3028, 3010, 2925, 2870, 1708, 1652, 1629, 1600, 1517, 1502/cm. [α]_D=+68.6° (MeOH, c=1.00, 22° C.).

[0928] No.2a-130

[0929] CDCl₃300 MHz; 1.02(1H, d, J=10.2 Hz), 1.04 and 1.26(each 3H, each s), 1.54-2.52(14H, m), 4.41(1H, m), 5.41-5.58(2H, m), 6.14(1H, d, J=9.0 Hz), 7.43-7.59(4H, m), 7.85-7.92(2H, m), 8.27(1H, dd, J=1.8 and 7.2 Hz). IR (CHCl₃): 3436, 3032, 3010, 2924, 2870, 2664, 1708, 1652, 1512, 1498/cm. [α]_D=+93.9° (MeOH, c=1.00, 22° C.) m.p. 94.0-96.0° C.

[0930] No.2a-131

[0931] [α]_D=+50.2° (MeOH, c=0.95, 21° C.).

[0932] No.2a-132

[0933] [α]_D=+10.9° (MeOH, c=0.92, 21° C.).,

[0934] No.2a-133

[0935] [α]_D=+60.4° (MeOH, c=1.00, 21° C.).

[0936] No.2a-134

[0937] [α]_D=+38.5° (MeOH, c=1.01, 23° C.).

[0938] No.2a-135

[0939] [α]_D=+52.5° (MeOH, c=1.01, 23° C.). m.p. 180.0-182.0° C.

[0940] No.2a-136 [α]_D=+35.3° (MeOH, c=1.02, 23° C.). m.p. 79.0-80.0° C.

[0941] No.2a-137

[0942] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.43(3H, t, J=6.9 Hz), 1.52-2.44(14H, m), 4.03(2H, q, J=6.9 Hz), 4.26(1H, m), 5.33-5.50(2H, m), 6.19(1H, d, J=8.7 Hz), 6.88-7.00(6H, m), 7.65-7.68(2H, m). IR (CHCl₃): 3455, 3031, 3024, 3014, 2988, 2925, 2870, 1741, 1708, 1649, 1602, 1521, 1504, 1490/cm. [α]_D=+52.0° (MeOH, c=1.01, 23° C.).

[0943] No.2a-138

[0944] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.35(6H, d, J=6.0 Hz), 1.53-2.46(14H, m), 4.25(1H, m), 4.51(1H, m), 5.33-5.50(2H, m), 6.12(1H, d, J=9.0 Hz), 6.87-6.99(6H, m), 7.65-7.68(2H, m). IR (CHCl₃): 3454, 3031, 3014, 2980, 2925, 2870, 1741, 1708, 1649, 1602, 1522, 1490/cm. [α]_D=+50.0° (MeOH, c=1.05, 22° C.).

[0945] No.2a-139

[0946] CDCl₃300 MHz; 1.00(1H, d, J=10.2 Hz), 1.16 and 1.24(each 3H, each s), 1.59-2.52(14H, m), 4.31(1H, m), 5.40-5.53(2H, m), 6.36(1H, d, J=8.7 Hz), 6.70(1H, d, J=1.5 Hz), 7.12(1H, m), 7.30(1H, m), 7.47(1H, dd, J=0.6 and 8.1 Hz), 7.61(1H, d, J=8.4 Hz). IR (CHCl₃): 3449, 8243, 3029, 3022, 3013, 2925, 2871, 1707, 1631, 1542, 1505/cm. [α]_D=+63.4° (MeOH, c=1.00, 23° C.). m.p. 178.0-179.0° C.

[0947] No.2a-140

[0948] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.18 and 1.23(each 3H, each s), 1.57-2.50(14H, m), 4.35(1H, m), 5.32-5.56(2H, m), 6.42(1H, d, J=8.7 Hz), 6.70(1H, d, J=1.5 Hz), 7.21-7.24(2H m), 7.46(1H, m), 7.76(1H, m), 7.86(1H, d, J=3.0 Hz), 10.20(1H, s). IR (CHCl₃): 3465, 3010, 2924, 1739, 1604, 1546, 1504/cm. [α]_D=+39.4° (MeOH, c=1.01, 22° C.). m.p. 167.0-168.0° C.

[0949] No.2a-141

[0950] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.55-2.44(14H, m), 3.84(3H, s), 4.27(1H, m), 5.34-5.52(2H, m), 6.28(1H, d, J=9.0 Hz), 6.91 and 7.47(each 2H, each d, J=9.0 Hz), 6.98 and 7.14(each 1H, each d, J=16.5 Hz), 7.54 and 7.70(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3453, 3025, 3015, 2925, 2870, 2839, 1740, 1708, 1649, 1602, 1510, 1493, 1470/cm. [α]_D=+73.4° (MeOH, c=1.02, 22° C.). m.p. 155.0-157.0° C.

[0951] No.2a-142

[0952] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.52-2.45(14H, m), 3.79(3H, s), 4.27(1H, m), 5.34-5.50(2H, m), 6.24(1H, d, J=9.0 Hz), 6.49 and 6.62(each 1H each d, J=12.3 Hz), 6.77 and 7.16(each 2H, each d, J=8.7 Hz), 7.32 and 7.59(each 2H, each d, J=8.1 Hz). IR (CHCl₃): 3453, 3025, 3014, 2925, 2870, 2839, 1739, 1708, 1649, 1606, 1510, 1494/cm. [α]_D=+60.7° (MeOH, c=0.99, 22° C.).

[0953] No.2a-143 [α]_D=+57.3° (MeOH, c=1.01, 23° C.).

[0954] No.2a-144 [α]_D=+12.2° (MeOH, c=1.00, 23° C.). m.p. 114.0-116.0° C.

[0955] No.2a-145

[0956] CDCl₃300 MHz; 0.95(1H, d, J=10.2 Hz), 1.10 and 1.21(each 3H, each s), 1.52-2.44(14H, m), 4.25(1H, m), 5.33-5.49(2H, m), 6.37(1H, d, J=8.7 Hz), 7.45-7.47(3H, m), 7.62-7.66(2H m), 7.69 and 7.80(each 2H, each d, J=7.5 Hz, ). IR (CHCl₃): 3449, 3058, 3027, 3012, 2925, 2870, 1708, 1655, 1513, 1481, 1043/cm. [α]_D=+61.0° (MeOH, c=1.01, 23° C.).

[0957] No.2a-146

[0958] CDCl₃300 MHz; 0.95(1H, d, J=10.5 Hz), 1.09 and 1.21(each 3H, each s), 1.50-2.41(14H, m), 4.25(1H, m), 5.33-5.49(2H, m), 6.33(1H, d, J=8.4 Hz), 7.49-7.61(3H, m), 7.91-7.92(2H, m), 7.82 and 7.97(each 2H, each d, J=8.7 Hz,). IR (CHCl₃): 3447, 3029, 3023, 3015, 2925, 2870, 1708, 1660, 1514, 1484, 1321, 1161/cm. [α]_D=+62.0° (MeOH, c=1.00, 22° C.).

[0959] No.2a-147

[0960] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.51(3H, s), 4.26(1H, m), 5.34-5.51(2H, m), 6.23(1H, d, J=8.4 Hz), 7.26 and 7.64(each 2H, each d, J=8.4 Hz). IR (CHCl₃): 3453, 3027, 3015, 2925, 2870, 2665, 1708, 1648, 1596, 1516, 1484/cm. [α]_D=+67.7° (MeOH, c=0.82, 226° C.).

[0961] No.2a-148 [α]_D=+72.5° (MeOH, c=1.01, 25° C.).

[0962] No.2a-149 [α]_D=+67.8° (MeOH, c=0.98, 25° C.).

[0963] No.2a-150

[0964] CDCl₃300 MHz; 0.94(1H, d, J=10.2 Hz), 1.10 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.22(1H, m), 5.36-5.55(2H, m), 6.48(1H, d, J=8.4 Hz), 8.35(1H, s), 8.90(1H, s). IR (CHCl₃): 3443, 3374, 3091, 3024, 3012, 2925, 2871, 1709, 1652, 1525, 1494/cm. [α]_D=+58.1° (MeOH, c=1.01, 23° C.). m.p. 120.0-122.0° C.

[0965] No.2a-151 [α]_D=+40.6° (MeOH, c=1.01, 23° C.).

[0966] No.2a-152

[0967] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.10 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 2.71(3H, s), 4.26(1H, m), 5.37-5.51(2H, m), 6.02(1H, d, J=9.0 Hz), 8.73(1H, s). IR (CHCl₃): 3463, 3435, 3087, 3025, 3014, 2925, 2870, 1708, 1649, 1523, 1503/cm. [α]_D=+54.1° (MeOH, c=1.02, 22° C.).

[0968] No.2a-153

[0969] CDCl₃300 MHz; 0.95(1H, d, J=9.9 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.50(14H, m), 2.50(3H, s), 4.26(1H, m), 5.36-5.51(2H, m), 6.01(1H, d, J=8.4 Hz), 6.88(1H, d, J=5.1 Hz), 7.26(1H, d, J=5.1 Hz). IR (CHCl₃): 3469, 3431, 3025, 3013, 2925, 2871, 2664, 1708, 1639, 1544, 1505/cm. [α]_D=+35.8° (MeOH, c=1.03, 22° C.).

[0970] No.2a-154

[0971] CDCl₃300 MHz; 0.95(1H, d, J=9.9 Hz), 1.10 and 1.22(each 3H, each s), 1.52-2.46(14H, m), 2.51(3H, d, J=1.2 Hz), 4.26(1H, m), 5.34-5.50(2H, m), 6.00(1H, d, J=8.4 Hz), 6.73(1H, dd, J=5.1 and 3.6 Hz), 7.29(1H, d, J=3.6 Hz). IR (CHCl₃): 3450, 3431, 3026, 3011, 2925, 2869, 1739, 1708, 1639, 1547, 1508/cm. [α]_D=+50.5° (MeOH, c=1.01, 22° C.).

[0972] No.2a-155

[0973] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.19 and 1.25(each 3H, each s), 1.53-2.48(14H, m), 4.31(1H, m), 5.36-5.51(2H, m), 6.79(1H, d, J=9.3 Hz), 7.29(1H, m), 7.41(1H, m), 7.48(1H, s), 7.51(1H, m), 7.66(1H, d, J=8.1 Hz). IR (CHCl₃): 3436, 3029, 3024, 3015, 2925, 2871, 2670, 1708, 1659, 1598, 1510/cm. [α]_D=+69.1° (MeOH, c=1.01, 22° C.).

[0974] No.2a-156

[0975] CDCl₃:CD₃O_D=10:1 300 MHz; 0.99(1H, d, J=9.9 Hz), 1.11 and 1.21(each 3H, each s), 1.56-2.58(14H, m), 4.22(1H, m), 5.35-5.59(2H, m), 6.83(1H, d, J=8.4 Hz), 7.48(1H, d, J=8.4 Hz), 7.61(1H, dd, J=1.5 and 8.4 Hz), 8.09(1H, d, J=1.5 Hz), 8.12(1H, s). IR (KBr): 3422, 3115, 2985, 2922, 2869, 2609, 1708, 1636, 1578, 1529, 1470/cm. [α]_D=+62.8° (MeOH, c=1.01, 22° C.).

[0976] No.2a-157 [α]_D=+40.0° (MeOH, c=0.95, 22° C.).

[0977] No.2a-158

[0978] CDCl₃300 MHz; 1.00(1H, d, J=10.5 Hz), 1.17 and 1.24(each 3H, each s), 1.54-2.50(14H, m), 4.34(1H, m), 5.36-5.52(2H, m), 7.80(1H, d, J=9.0 Hz), 9.30(1H, s). IR (CHCl₃): 3410, 3122, 3030, 3012, 2925, 2871, 2668, 1709, 1667, 1538, 1466/cm. [α]_D=+44.9° (MeOH, c=0.99, 220° C.).

[0979] No.2a-159

[0980] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.13 and 1.22(each 3H, each s), 1.55-2.43(14H, m), 3.03(6H, s), 4.23(1H, m), 5.32-5.51(2H, m), 6.16(1H, d, J=8.7 Hz), 6.87 and 7.63(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3457, 3028, 3006, 2924, 2870, 2654, 1739, 1709, 1637, 1608, 1608, 1534, 1501/cm. [α]_D=+64.8° (MeOH, c=1.01, 22° C.).

[0981] No.2a-160

[0982] d₆-DMSO 300 MHz; 0.83(1H, d, J=9.9 Hz), 1.02 and 1.19(each 3H, each s), 1.38-1.61(3H, m), 1.90-2.32(11H, m), 3.90(1H, m), 5.41-5.44(2H, m), 7.32(1H, dd, J=0.9 and 7.2 Hz), 7.45-7.60(2H, m), 7.77(1H, dd, J=0.9 and 7.8 Hz), 8.03(1H, d, J=6.9 Hz), 12.40(1H, s). IR (Nujol): 3315, 2924, 2856, 2656, 2535, 1737, 1703, 1637, 1598, 1581, 1541/cm. [α]_D=+78.5° (MeOH, c=1.01, 24° C.). m.p. 161.0-162.0° C.

[0983] No.2a-161 [α]_D=+65.3° (MeOH, c=1.00, 22° C.).

[0984] No.2a-162

[0985] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.13 and 1.25(each 3H, each s), 1.53-2.45(14H, m), 4.30(1H, m), 5.36-5.51(2H, m), 6.32(1H, d, J=8.4 Hz), 7.88 and 8.28(each 2H, each d, J=9.0 Hz). IR (CHCl₃): 3448, 3029, 3016, 2925, 2870, 1708, 1664, 1602, 1527, 1484, 1347/cm. [α]_D=+72.7° (MeOH, c=1.02, 22° C.).

[0986] No.2a-163

[0987] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.55-2.51(14H, m), 4.26(1H, m), 5.36-5.57(2H, m), 6.68(1H, d, J=7.8 Hz), 7.41(1H, dd, J=4.8 and 8.1Hz), 8.20(1H, d, J=8.1 Hz), 8.66(1H, d, J=4.8 Hz), 9.00(1H, s). IR (CHCl₃): 3448, 3026, 3013, 2925, 2870, 2534, 1709, 1658, 1590, 1515, 1471/cm. [α]_D=+71.3° (MeOH, c=1.01, 22° C.).

[0988] No.2a-164 [α]_D=+40.8° (MeOH, c=0.98, 22° C.).

[0989] No.2a-165

[0990] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.11 and 1.24(each 3H, each s), 1.55-2.52(14H, m), 4.24(1H, m), 5.37-5.57(2H, m), 6.63(1H, d, J=7.8 Hz), 7.59 and 8.63(each 2H each d, J=6.0 Hz). IR (CHCl₃): 3447, 3346, 3028, 3016, 2925, 2870, 2538, 1941, 1708, 1662, 1556, 1516/cm. [α]_D=+75.4° (MeOH, c=1.01, 22° C.).

[0991] No.2a-166

[0992] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.51-2.44(14H, m), 2.95(6H, s), 4.25(1H, m), 5.33-5.50(2H, m), 6.19(1H, d, J=8.7 Hz), 6.77 and 6.97(each 2H, each d, J=8.4 Hz), 6.94 and 7.65(each 2H, each d, J=9.0 Hz). IR (CHCl₃): 3453, 3024, 3016, 2924, 2871, 2806, 1739, 1708, 1647, 1612, 1604, 1515, 1490/cm. [α]_D=+53.1° (MeOH, c=1.02, 23° C.). m.p. 104.0-105.5° C.

[0993] No.2a-167

[0994] CDCl₃300 MHz; 1.01(1H, d, J=9.9 Hz), 1.19 and 1.26(each 3H, each s), 1.56-2.53(14H, m), 4.37(1H, m), 5.35-5.55(2H, m), 6.47(1H, d, J=8.4Hz), 7.61-7.71(2H, m), 7.79(2H, s), 7.89-7.97(2H, m), 8.27(1H, d, J=2.1 Hz), 8.66-8.73(2H, m). IR (CHCl₃): 3450, 3024, 3014, 2925, 2870, 2667, 1707, 1650, 1531, 1509/cm. [α]_D=+70.5° (MeOH, c=1.00, 22° C.).

[0995] No.2a-168

[0996] CDCl₃300 MHz; 1.02(1H, d, J=10.2 Hz), 1.20 and 1.26(each 3H, each s), 1.56-2.50(14H, m), 4.38(1H, m), 5.36-5.56(2H, m), 6.51(1H, d, J=8.4 Hz), 7.61-7.93(7H, m), 8.74(1H, d, J=8.4 Hz), 9.15(1H, s). IR (CHCl₃): 3517, 3451, 3060, 3028, 3011, 2925, 2870, 2664, 1709, 1651, 1519, 1498/cm. [α]_D=+54.4° (MeOH, c=1.00, 23° C.).

[0997] No.2a-169

[0998] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.09 and 1.21(each 3H, each s), 1.50-2.44(14H, m), 3.85(3H, s), 4.24(1H, m), 5.32-5.48(2H, m), 6.19(1H, d, J=8.4 Hz), 6.94 and 7.45(each 2H, each d, J=9.0 Hz), 7.11 and 7.45(each 2H, each d, J=8.7 Hz). IR (CHCl₃): 3516, 3453, 3029, 3009, 2925, 2870, 2840, 2665, 1708, 1650, 1593, 1515, 1493, 1482/cm. [α]_D=+57.8° (MeOH, c=1.00, 23° C.).

[0999] No.2a-170

[1000] CDCl₃300 MHz; 0.98(1H, d, J=10.2 Hz), 1.15 and 1.24(each 3H, each s), 1.52-2.50(14H, m), 4.28(1H, m), 5.33-5.54(2H, m), 6.25(1H, d, J=8.2 Hz), 7.38-7.44(2H, m), 7.74(1H, s), 7.81-7.86(2H, m). IR (CHCl₃): 3517, 3448, 3427, 3024, 3013, 2925, 2870, 2669, 1708, 1650, 1562, 1535, 1500/cm. [α]_D=+61.6° (MeOH, c=1.00, 23° C.).

[1001] No.2a-171

[1002] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz, 1.11 and 1.22(each 3H, each s), 1.52-2.42(14H, m), 2.48(3H, s), 4.21(1H, m), 6.31-5.52(2H, m), 6.06(1H, d, J=8.2 Hz), 6.97 and 7.59(each 1H, each d, J=1.2 Hz). IR (CHCl₃): 3452, 3113, 3028, 3007, 2925, 2870, 2669, 1708, 1645, 1554, 1509/cm. [α]_D=+52.4° (MeOH, c=1.00, 23° C.).

[1003] No.2a-172

[1004] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.09 and 1.28(each 3H, each s), 1.50-2.40(14H, m), 2.69(3H, s), 4.24(1H, m), 5.35-5.51(2H, m), 5.96(1H, d, J=8.7 Hz), 7.03 and 7.07(each 1H, each d, J=5.4 Hz). IR (CHCl₃): 3451, 3031, 3013, 2925, 2870, 2666, 1708, 1647, 1542, 1497/cm. [α]_D=+51.2° (MeOH, c=1.00, 23° C.).

[1005] No.2a-173

[1006] CDCl₃300 MHz; 0.95(1H, d, J=10.2 Hz), 1.10 and 1.23(each 3H, each s), 1.50-2.45(14H, m), 4.22(1H, m), 5.35-5.49(2H, m), 6.05(1H, d, J=8.4 Hz), 7.26 and 7.75(each 1H, each d, J=1.5 Hz). IR (CHCl₃): 3451, 3011, 3029, 3011, 2925, 2870, 1708, 1652, 1538, 1500/cm. [α]_D=+50.6° (MeOH, c=1.01, 23° C.).

[1007] No.2a-174

[1008] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.13 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.29(1H, m), 5.35-5.51(2H, m), 7.02(1H, d, J=8.4 Hz), 7.32 and 8.16(each 1H, each d, J=3.9 Hz). IR (CHCl₃): 3417, 3115, 3023, 3014, 2925, 2870, 1708, 1645, 1530/cm. [α]_D=+48.8° (MeOH, c=1.02, 23° C.).

[1009] No.2a-175

[1010] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.14 and 1.23(each 3H, each s), 1.50-2.52(14H, m), 2.52(3H, s), 4.29(1H, m), 5.34-5.51(2H, m), 7.78(1H, d, J=9.0 Hz), 7.24 and 7.52(each 1H, each d, J=5.4 Hz). IR (CHCl₃): 3329, 3093, 3023, 3015, 2924, 2871, 1708, 1640, 1526/cm. [α]_D=+45.0° (MeOH, c=1.01, 23° C.).

[1011] No.2a-176

[1012] CDCl₃300 MHz; 0.95(1H, d, J=10.5 Hz), 1.09 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.40(3H, d, J=0.9 Hz), 4.24(1H, m), 5.35-5.51(2H, m), 6.05(1H, d, J=8.7 Hz), 6.95(1H, m), 7.57(1H, d, J=3.3 Hz). IR (CHCl₃): 3517, 3444, 3103, 3024, 3013, 2926, 2870, 1739, 1708, 1649, 1636, 1507/cm. [α]_D=+54.8° (MeOH, c=1.01, 23° C.). m.p. 97.0-99.0° C.

[1013] No.2a-177

[1014] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.19 and 1.23(each 3H, each s), 1.52-2.45(14H, m), 3.93(3H, s), 4.27(1H, m), 5.34-5.50(2H, m), 6,35(1H, d, J=3.3 Hz), 7.80(1H, d, J=8.7 Hz), 8.10(1H, d, J=3.3 Hz). IR (CHCl₃): 3395, 3121, 3031, 3019, 3012, 2925, 2871, 1739, 1709, 1640, 1557, 1533/cm. [α]_D=+22.8° (MeOH, c=1.01, 23° C.). m.p. 109.0-112.0° C.

[1015] No.2a-178

[1016] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.10 and 1.23(each 3H, each s), 1.51-2.45(14H, m), 4.24(1H, m), 5.35-5.50(2H, m), 6.09(1H, d, J=8.4 Hz), 7.17-7.31(6H, m), 7.95(1H, d, J=1.5 Hz). IR (CHCl₃): 3510, 3451, 3062, 3031, 3022, 3011, 2925, 2870, 2662, 1708, 1651, 1582, 1535, 1497, 1477/cm. [α]_D=+47.9° (MeOH, c=1.01, 25° C.).

[1017] No.2a-179

[1018] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.52-2.48(14H, m), 4.30(1H, m), 5.36-5.52(2H, m), 6.73(1H, d, J=9.0 Hz), 6.26 and 7.37(each 1H, each d, J=6.0 Hz). IR (CHCl₃): 3509, 3429, 3115, 3094, 3025, 3014, 2925, 2871, 2666, 1708, 1649, 1529, 1510/cm. [α]_D=+51.0° (MeOH, c=1.02, 25° C.).

[1019] No.2a-180

[1020] CDCl₃300 MHz; 0.95(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.52-2.46(14H, m), 3.89(3H, s), 4.21(1H, m), 5.35-5.50(2H, m), 6.05(1H, d, J=8.4 Hz), 6.46 and 7.04(each 1H, each d, J=1.8 Hz). IR (CHCl₃): 3516, 3450, 3114, 3031, 3010, 2925, 2871, 1708, 1648, 1546, 1511, 1477/cm. [α]_D=+49.1° (MeOH, c=1.01, 25° C.).

[1021] No.2a-181

[1022] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.14 and 1.23(each 3H, each s), 1.52-2.48(14H, m), 2.42(3H, s), 4.31(1H, m), 5.34-5.52(2H, m), 8.07(1H, d, J=9.3 Hz), 7.27 and 8.17(each 1H, each d, J=3.3 Hz). IR (CHCl₃): 3510, 3301, 3112, 3023, 3007, 2924, 2871, 2663, 1708, 1636, 1534/cm. [α]_D=+41.0° (MeOH, c=0.96, 25° C.).

[1023] No.2a-182

[1024] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.53-2.46(14H, m), 2.51(3H, s), 4.21(1H, m), 5.35-5.51(2H, m), 6.05(1H, d, J=8.1 Hz), 7.26 and 7.78(each 1H, each d, J=1.8 Hz). IR (CHCl₃): 3509, 3450, 3109, 3024, 3012, 2925, 2870, 2666, 1708, 1650, 1535, 1498, 1471/cm. [α]_D=+52.9° (MeOH, c=0.95, 25° C.).

[1025] No.2a-183

[1026] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.12 and 1.22(each 3H, each s), 1.52-2.46(14H, m), 4.25(1H, m), 5.33-5.51(2H, m), 6.17(1H, d, J=8.7 Hz), 7.01-7.05(3H, m). 7.14 and 7.62(each 2H, each d, J=8.7 Hz), 7.27-7.34(2H, m). IR (CHCl₃): 3428, 3026, 3015, 2925, 2870, 2666, 1739, 1708, 1643, 1613, 1594, 1526, 1499/cm. [α]_D=+64.8° (MeOH, c=1.02, 23° C.).

[1027] No.2a-184

[1028] CDCl₃300 MHz; 1.01(1H, d, J=10.2 Hz), 1.18 and 1.26(each 3H, each s), 1.55-2.50(14H, m), 4.35(1H, m), 5.35-5.55(2H, m), 6.42(1H, d, J=8.7 Hz), 7.46-7.52(2H, m), 7.73(1H, dd, J=1.8 and 8.4 Hz), 7.83-7.89(2H, m), 8.21(1H, m), 8.59(1H, d, J=1.5 Hz). IR (CHCl₃): 3451, 3031, 3014, 2925, 2870, 2660, 1739, 170821650, 1604, 1513, 1463/cm. [α]_D=+58.3° (MeOH, c=1.00, 23° C.).

[1029] No.2a-185

[1030] CDCl₃300 MHz; 1.00(1H, d, J=10.2 Hz), 1.18 and 1.25(each 3H, each s), 1.55-2.50(14H, m), 4.34(1H, m), 5.35-5.54(2H, m), 6.36(1H, d, J=8.7 Hz), 7.37(1H, t, J=7.4 Hz), 7.50(1H, m), 7.57-7.59(2H, m), 7.79(1H, dd, J=1.8 and 8.1 Hz), 7.99(1H, d, J=7.8 Hz), 8.39(1H, d, J=1.8 Hz). IR (CHCl₃): 3451, 3030, 3020, 2870, 2665, 1708, 1652, 1632, 1603, 1586, 1514, 1469, 1448/cm. [α]_D=+59.4° (MeOH, c=1.01, 24° C.).

[1031] No.2a-186

[1032] CDCl₃300 MHz; 1.00(1H, d, J=10.5 Hz), 1.17 and 1.25(each 3H, each s), 1.54-2.50(14H, m), 4.33(1H, m), 5.35-5.54(2H, m), 6.37(1H, d, J=8.7 Hz), 7.37(1H, t, J=7.4 Hz), 7.51(1H, t, J=7.8 Hz), 7.56(1H, m), 7.70(1H, dd, J=1.2 and 8.4 Hz), 7.97(3H, m). IR (CHCl₃): 3451, 3030, 3014, 2924, 2870, 2671, 1739, 1708, 1652, 1577, 1517, 1488, 1471/cm. [α]_D=+72.2° (MeOH, c=1.00, 24° C.).

[1033] No.2a-187

[1034] CDCl₃300 MHz; 1.00(1H, d, J=9.8 Hz), 1.18 and 1.25(each 3H, each s), 1.54-2.53(14H, m), 4.07(3H, s), 4.37(1H, m), 5.30-5.54(2H, m), 7.34(1H, m), 7.47(1H, s), 7.47-7.60(2H, m), 7.93(1H, d, J=7.8 Hz), 8.43(1H, s), 8.49(1H, d, J=9.0 Hz). IR (CHCl₃): 3397, 3074, 3027, 3020, 3009, 2924, 1738, 1708, 1647, 1633, 1534, 1465, 1453/cm. [α]_D=+43.7° (MeOH, c=1.01, 25° C.).

[1035] No.2a-188

[1036] CDCl₃300 MHz; 0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.53-2.50(14H, m), 4.23(1H, m), 5.37-5.50(2H, m), 6.10(1H, d, J=9.0 Hz), 6.20(1H, m), 6.51(1H, m), 6.97(1H, m), 10.81(1H, brs). IR (CHCl₃): 3450, 3236, 3112, 3029, 3015, 2925, 2871, 2645, 1701, 1616, 1558, 1516/cm. [α]_D=+50.6° (MeOH, c=1.01, 24° C.).

[1037] No.2a-189

[1038] CDCl₃300 MHz; 0.94(1H, d, J=9.9 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.46(14H, m), 3.93(3H, s), 4.18(1H, m), 5.35-5.52(2H, m), 6.03(1H, d, J=9.3 Hz), 6.09(1H, m), 6.48(1H, m), 6.73(1H, m). IR (CHCl₃): 3452, 3102, 3028, 3007, 2925, 2871, 2666, 1739, 1708, 1650, 1536, 1499, 1471/cm. [α]_D=+49.8° (MeOH, c=1.01, 23° C.). m.p. 101.5-103.5° C.

[1039] No.2a-190

[1040] CDCl₃300 MHz; 0.94(1H, d, J=10.2 Hz), 1.11 and 1.21(each 3H, each s), 1.54-2.47(14H, m), 4.23(1H, m), 5.33-5.52(2H, m), 6.06(1H, d, J=9.0 Hz), 6.34(1H, m), 6.75(1H, m), 6.36(1H, m), 9.71(1H, brs). IR (CHCl₃): 3470, 3215, 3030, 3020, 3010, 2925, 2871, 2664, 1709, 1613, 1564, 1510/cm. [α]_D=+43.3° (MeOH, c=1.01, 24° C.).

[1041] No.2a-191

[1042] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.55-2.44(14H, m), 3.66(3H, s), 4.20(1H, m), 5.35-5.51(2H, m), 5.93(1H, d, J=8.4 Hz), 6.27(1H, dd, J=1.8 and 2.7 Hz), 6.56(1H, t, J=2.7 Hz), 7.19(1H, t, J=1.8 Hz). IR (CHCl₃): 3452, 3031, 3018, 3006, 2925, 2871, 2662, 1736, 1710, 1634, 1609, 1556, 1498/cm. [α]_D=+43.1° (MeOH, c=1.01, 23° C.).

[1043] No.2a-192

[1044] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.11 and 1.21(each 3H, each s), 1.43(3H, t, J=7.5 Hz), 1.54-2.44(14H, m), 3.93(2H, q, J=7.5 Hz), 4.21(1H, m), 5.33-5.51(2H, m), 5.94(1H, J=8.4 Hz), 6.27(1H, dd, J=1.8 and 2.7 Hz), 6.62(1H, t, J=2.7 Hz), 7.26(1H, t, J=1.8 Hz). IR (CHCl₃): 3630, 3452, 3032, 3018, 3006, 2925, 2871, 2661, 1735, 1710, 1633, 1610, 1555, 1497/cm. [α]_D=+40.1° (MeOH, c=1.00, 23° C.).

[1045] No.2a-193

[1046] CDCl₃300 MHz; 0.95(1H, d, J=10.2 Hz), 1.10 and 1.22(each 3H, each s), 1.53-2.49(14H, m), 2.58(3H, s), 4.21(1H, m), 5.35-5.54(2H, m), 6.15(1H, d, J=8.1 Hz), 6.52(1H, dd, J=1.8 and 3.6 Hz), 7.29(1H, t, J=3.6 Hz), 7.94(1H, t, J=1.8 Hz). IR (CHCl₃): 3516, 3450, 3410, 3152, 3027, 3015, 2925, 2871, 2670, 1732, 1648, 1574, 1509/cm. [α]_D=+45.0° (MeOH, c=1.01, 25° C.).

[1047] No.2a-194

[1048] CDCl₃300 MHz; 0.99(1H, d, J=10.2 Hz), 1.11 and 1.24(each 3H, each s), 1.52-2.53(14H, m), 4.34(1H, m), 5.33-5.57(2H, m), 6.21(1H, d, J=8.6 Hz), 7.35-7.50(2H, m), 7.83(1H, s) 7.86(1H, m), 8.31(1H, m). IR (CHCl₃): 3443, 3067, 3013, 2925, 2870, 2665, 1708, 1651, 1515, 1493/cm. [α]_D=+55.7° (MeOH, c=1.01, 23° C.).

[1049] No.2a-195

[1050] CDCl₃300 MHz; 1.01(1H, d, J=10.0 Hz), 1.06 and 1.26(each 3H, each s), 1.50-2.64(14H, m), 2.68(3H, s), 4.40(1H, m), 5.36-5.61(2H, m), 6.02(1H, d, J=9.4 Hz), 7.30-7.42(2H, m), 7.73-7.86(2H, m). IR (CHCl₃): 3510, 3434, 3062, 3029, 3014, 2924, 2871, 2669, 1708, 1650, 1563, 1539, 1500/cm. [α]_D=+72.4° (MeOH, c=1.00, 23° C.). m.p. 111.0-112.0° C.

[1051] No.2a-196

[1052] CDCl₃300 MHz; 0.42 and 1.04(each 3H, each s), 0.80(1H, d, J=10.0 Hz), 1.11-2.48(14H, m), 2.24(3H, s), 4.02(1H, m), 5.23-5.44(2H, m), 5.53(1H, d, J=8.8 Hz), 7.27-7.31(2H, m), 7.42-7.48(3H, m), 7.93(1H, s). IR (CHCl₃): 3419, 3114, 3025, 3006, 2924, 2871, 2662, 1737, 1709, 1636, 1540, 1519/cm. [α]_D=+43.7° (MeOH, c=1.01, 23° C.).

[1053] No.2a-197

[1054] CDCl₃300 MHz; 0.95(1H, d, J=10.0 Hz), 1.09 and 1.23(each 3H, each s), 1.54-2.46(18H, m), 2.77(4H, brs), 4.21(1H, m), 5.32-5.54(2H, m), 6.02(1H, d, J=8.6 Hz), 7.43(1H, s). IR (CHCl₃): 3445, 3101, 3024, 3014, 2928, 2865, 2661, 1739, 1708 1646, 1550, 1507/cm. [α]_D=+51.9° (MeOH, c=1.01, 23° C.).

[1055] No.2a-198

[1056] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.50-2.44(14H, m), 4.24(1H, m), 4.42(2H, s), 5.35-5.49(2H, m), 6.25(1H, d, J=8.1 Hz), 7.33(1H, m), 7.43(1H, dd, J=1.5 and 7.5 Hz), 7.49(1H, d, J=8.1 Hz), 7.60-7.63(1H, m), 7.68(1H, dd, J=1.8 and 7.8 Hz), 8.02(1H, d, J=1.8 Hz), 8.19(1H, dd, J=1.5 and 8.1 Hz). IR (CHCl₃): 3448, 3030, 3012, 2925, 2870, 1739, 1708, 1671, 1588, 1559, 1514, 1472/cm. [α]_D=+56.9° (MeOH, c=1.01, 24° C.).

[1057] No.2a-199

[1058] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.51-2.46(14H, m), 3.40(1H, m), 3.76(1H, m), 4.24(1H, m), 5.33-5.51(3H, m), 6.25(1H, m), 7.16(1H, m), 7.24-7.33(2H, m), 7.46(1H, d, J=7.5 Hz), 7.52-7.60(2H, m), 7.85(1H, dd, J=1.8 and 5 Hz). IR (CHCl₃): 3583, 3447, 3062, 3028, 3013, 2924, 2871, 2663, 1708, 1651, 1600, 1557, 1514, 1471/cm. [α]_D=+54.8° (MeOH, c=1.00, 23° C.).

[1059] No.2a-200

[1060] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.51-2.46(14H, m), 4.25(1H, m), 5.34-5.51(2H, m), 6.25(1H, d, J=8.4 Hz), 7.02 and 7.10(each, 1H, each d, J=12.3 Hz), 7.23-7.33(4H, m), 7.50(1H, m), 7.64(1H, dd, J=1.8 and 7.8 Hz), 7.82(1H, d, J=1.8 Hz). IR (CHCl₃): 3450, 3060, 3025, 3014, 2925, 2871, 2662, 1708, 1653, 1596, 1542, 1513, 1473/cm. [α]_D=+62.5° (MeOH, c=1.00, 24° C.).

[1061] No.2a-201

[1062] CDCl₃300 MHz; 0.95(1H, d, J=9.9 Hz), 1.15 and 1.22(each 3H, each s), 1.55-2.60(14H, m), 4.26(1H, m), 5.35-5.63(2H, m), 7.14(1H, d, J=9.9 Hz), 7.34 and 7.40(each, 1H, each d, J=12.9 Hz), 7.62-7.73(4H, m), 8.25-8.30(2H, m), 8.72(1H, d, J=1.5 Hz). IR (CHCl₃): 3443, 3389, 3297, 3061, 3030, 3016, 2925 2870, 1726, 1708 1652, 1603, 1521, 1483, 1472, 1309/cm. [α]_D=+61.1° (MeOH, c=1.01, 23° C.).

[1063] No.2a-202

[1064] CDCl₃300 MHz; 0.96(1H, d, J=10.2 Hz), 1.09 and 1.22(each 3H, each s), 1.52-2.43(14H, m), 2.63(3H, s), 4.25(1H, m), 5.33-5.49(2H, m), 6.19(1H, d, J=8.4 Hz), 7.10 and 7.58(15 each, 2H, each d, J=9.0 Hz), 7.21(1H, m), 7.30-7.32(2H, m), 7.46(1H, d, J=7.5 Hz) IR (CHCl₃): 3511, 3453, 3062, 3032, 3014, 2925 2870, 1739, 1708, 1650, 1595, 1556, 1516, 1482, 1471/cm. [α]_D=+60.2° (MeOH, c=1.01, 25° C.).

[1065] No.2a-203

[1066] CDCl₃300 MHz; 0.96(1H, d, J=10.5 Hz), 1.09 and 1.23(each 3H, each s), 1.52-2.43(14H, m), 4.23(1H, m), 5.35-5.51(2H, m), 5.93(1H, d, J=8.7 Hz), 6.56(1H, dd, J=0.9 and 1.8Hz), 7.43(1H, t, J=1.8 Hz), 7.92(1H, dd, J=0.9 and 1.8 Hz). IR (CHCl₃): 3517, 3450, 3134, 3031, 3008, 2925, 2870, 2667, 1708, 1656, 1588, 1570, 1514/cm. [α]_D=+46.7° (MeOH, c=0.92, 25° C.).

[1067] No.2b-1

[1068] [α]_D=+25.6° (MeOH, c=1.01, 23° C.).

[1069] No.2b-2

[1070] [α]_D=+38.9° (MeOH, c=1.01, 24° C.).

[1071] No.2c-1

[1072] [α]_D=+60.5° (MeOH, c=1.01, 22° C.).

[1073] No.2c-2

[1074] [α]_D=+55.8° (MeOH, c=0.92, 22° C.).

[1075] No.2c-3

[1076] [α]_D=+54.7° (MeOH, c=1.01, 22° C.).

[1077] No.2d-1

[1078] [α]_D=−6.2° (MeOH, c=1.00, 21° C.).

[1079] No.2d-2

[1080] [α]_D=+15.8° (MeOH, c=0.34, 22° C).

[1081] No.2d-3

[1082] [α]_D=+31.6° (MeOH, c=1.01, 22° C.).

[1083] No.2e-1

[1084] [α]_D=−9.4° (MeOH, c=1.00, 22° C.).

[1085] No.2e-2

[1086] [α]_D=−1.8° (MeOH, c=1.02, 23° C.).

[1087] No.2e-3

[1088] [α]_D=−6.7° (MeOH, c=1.01, 23° C.).

[1089] No.2f-1

[1090] [α]_D=+6.8° (MeOH, c=1.01, 23° C.).

[1091] No.2f-2

[1092] [α]_D=−2.6° (MeOH, c=1.00, 22° C.).

[1093] No.2f-3

[1094] [α]_D=−3.5° (MeOH, c=1.01, 22° C.).

[1095] No.2g-1

[1096] [α]_D=+54,6° (MeOH, c=1.01, 24° C.).

[1097] No.3a-2

[1098] CDCl₃300 MHz; 0.98-2.15(14H, m), 2.31(2H, t, J=7.2 Hz), 2.35-2.40(1H, m), 3.10-3.20(1H, m), 5.00(1H, d, J=6.9 Hz), 5.30-5.48(2H, m), 6.75(1H, d, J=10.2 Hz), 7.38-7.52(6H, m). IR (CDCl₃): 3266, 3028, 2954, 2874, 1709, 1620, 1448, 1412, 1318, 1141, 970, 892/cm. [α]_D=+20.3±0.6° (CHCl₃, c=1.05, 24° C.).

[1099] No.3a-3

[1100] CDCl₃300 MHz; 0.95-2.00(14H, m), 2.20-2.29(3H, m), 3.00-3.08(1H, m), 3.66(3H, s), 5.00(1H, d, J=6.6 Hz), 5.13-5.29(2H, m), 7.38-7.52(3H, m), 7.59-7.65(2H, m), 7.69-7.75(2H, m), 7.92-7.98(2H, m). IR (CHCl₃): 3376, 3018, 2946, 2868, 1727, 1594, 1436, 1395, 1322, 1157, 1095, 890/cm. [α]_D=+2.3±0.4° (CHCl₃, c=1.03, 22° C.). mp. 65-66.5° C.

[1101] No.3a-4

[1102] CDCl₃300 MHz; 0.93-2.05(14H, m), 2.15-2.22(1H, m), 2.31(2H, t, J=7.2 Hz), 3.01-3.10(1H, m), 5.18-5.31(3H, m), 7.38-7.52(3H, m), 7.58-7.66(2H, m), 7.69-7.76(2H, m), 7.92-7.98(2H, m) IR (CHCl₃): 3374, 3260, 3020, 2948, 2868, 1708, 1594, 1479, 1396, 1319, 1156, 1095, 1052, 891/cm. [α]_D=+13.10.5° (CHCl₃, c=1.16, 24° C.).

[1103] No.3a-6

[1104] CD₃OD 300 MHz; 1.04-1.95(14H, m), 2.07(2H, t, J=7.8 Hz), 2.14-2.22(1H, m), 2.94-3.00(1H, m), 5.04-5.25(2H, m), 7.36-7.52(3H, m), 7.66-7.71(2H, m), 7.78-7.85(2H, m), 7.91-7.97(2H, m). IR (KBr): 3421, 3278, 2951, 2872, 1562, 1481, 1409, 1317, 1156, 1097, 1057, 895/cm [α]_D=−15.3±0.5° (CHCl₃, c=1.06, 23° C.). mp. 105-112° C.

[1105] No.3a-11

[1106] CDCl₃300 MHz; 0.90-2.04(14H, m), 2.08-2.19(1H, m), 2.35(2H, t, J=7.2 Hz), 2.95-3.04(1H, m), 5.17-5.32(3H, m), 7.56-7.63(2H, m), 7.83-7.95(2H, m). IR (CHCl₃): 3260, 3020, 2948, 2868, 1707, 1569, 1456, 1383, 1325, 1268, 1160, 1088, 1053, 1006, 892/cm. [α]_D=+8.3±0.5° (CHCl₃, c=1.00, 22° C.).

[1107] No.3a-16

[1108] CDCl₃300 MHz; 0.80-1.90(14H, m), 1.98-2.04(1H, m), 2.27(2H, t, J=7.2 Hz), 2.88(6H, s), 2.90-2.98(1H, m), 4.88-5.00(2H, m), 5.13(1H, d, J=7.2 Hz), 7.18(1H, d, J=7.5 Hz), 7.48-7.60(2H, m), 8.25-8.33(2H, m), 8.53(1H, d, J=8.7 Hz). IR (CHCl₃): 3272, 3020, 2946, 2866, 2782, 1708, 1573, 1455, 1407, 1311, 1229, 1160, 1142, 1070, 942, 891/cm. [α]_D=−19.7±0.6° (CHCl₃, c=1.08, 23.5° C.).

[1109] No.3a-31

[1110] CDCl₃300 MHz; 0.80-1.85(14H, m), 2.02-2.08(1H, m), 2.20(2H, t, J=7.2 Hz), 2.85-2.95(1H, m), 3.68(3H, s), 4.80-4.92(2H, m), 4.96(1H, d, J=6.9 Hz), 7.50-7.70(3H, m), 7.92-7.98(1H, m), 8.07(1H, d, J=8.4 Hz), 8.29(1H, dd, J=1.5&7.5 Hz), 8.65(1H, d, J=8.7 Hz). IR (CHCl₃): 3374, 3016, 2946, 2868, 1727, 1506, 1435, 1318, 1160, 1133, 1105, 1051, 984, 890/cm. [α]_D=−39.3±0.8° (CHCl₃, c=1.07, 22° C.).

[1111] No.3a-32

[1112] CDCl₃300 MHz; 0.80-1.90(14H, m), 1.95-2.05(1H, m), 2.27(2H, t, J=7.2 Hz), 2.90-2.96(1H, m) 4.85-5.00(2H, m), 5.23(1H, d, J=6.6 Hz), 7.50-7.72(3H, m), 7.95(1H, d, J=8.1 Hz), 8.07(1H, d, J=8.4 Hz), 8.29(1H, dd, J=1.2&7.5 Hz), 8.66(1H, d, J=9.0 Hz). IR (CHCl₃): 3270, 3020, 2948, 2868, 1708, 1455, 1412, 1317, 1159, 1132, 1104, 1079, 1051, 983, 891/cm. [α]_D=−29.2±0.6° (CHCl₃, c=1.08, 220° C.).

[1113] No.3a-33

[1114] CD₃OD 300 MHz; 0.94-1.84(14H, m), 1.96-2.08(3H, m), 2.77-2.84(1H, m), 4.67-4.84(2H, m), 7.55-7.75(3H, m), 8.02(1H, d, J=7.8 Hz), 8.12-8.26(2H, m), 8.74(1H, d, J=8.7 Hz). IR (KBr): 3432, 3298, 2951, 2872, 1564, 1412, 1315, 1159, 1134, 1107, 1082, 1058, 986/cm. [α]_D=−79.9±1.2° (CH₈OH, c=1.00, 23° C.).

[1115] No.3a-34

[1116] CDCl₃300 MHz; 0.97-1.91(14H, m), 2.13-2.20(1H, m), 2.42(2H, t, J=7.2 Hz), 3.00-3.07(1H, m), 5.06-5.24(2H, m), 5.33(1H, d, J=6.9 Hz), 7.57-7.68(2H, m), 7.82-8.00(4H, m), 8.45(1H, d, J=1.2 Hz) IR (CHCl₃): 3260, 3020, 2948, 1708, 1408, 1319, 1154, 1129, 1073, 953, 893/cm. [α]_D=+20.7±0.6° (CHCl₃, c=1.07, 22° C.).

[1117] No.3a-35

[1118] CD₈OD 300 MHz; 1.03-2.20(m, 17H), 2.97(m, 1H), 5.02(m, 2H), 7.64(m, 2H), 8.00(m, 4H), 8.43(S, 1H). IR (KBr): 3360, 3285, 1562, 1407, 1316, 1153, 1130, 1075/cm. [α]÷0 [α]₃₆₅=+20.9±0.6° (CH₃OH, c=1.04, 23° C.).

[1119] No.3d-1

[1120] CDCl₃300 MHz; 93-2.55(m, 17H), 3.02(m, 1H), 5.24(m, 2H), 6.48(m, 1H), 7.35-7.60(m, 3H), 7.85-8.00(m, 2H) IR (Nujol): 3275, 1548, 1160, 1094, 758, 719, 689, 591, 557/cm. [α]_D=+19.0±0.6° (CH₃OH, c=1.010, 26.5° C.). Elemental analysis (C₂₀H₂₆NO₄S 1/2Ca 1.0 H₂O) Calcd.: C, 57.94; H, 6.82; N, 3.38; Ca, 4.83; H₂O, 4.35 Found: C, 57.80; H, 6.68; N, 3.68; Ca, 5.06; H₂O, 4.50

[1121] No.3d-6

[1122] [α]_D=−20.7±0.6° (CHCl₃, c=1.00, 24° C.).

[1123] No.3d-7

[1124] [α]_D=−3.2±0.4° (CHCl₃: c=1.03, 22° C.). mp. 65-67° C.

[1125] No.3d-8

[1126] [α]_D=−14.5±0.5° (CHCl₃, c=1.07, 24° C.).

[1127] No.3d-9

[1128] [α]_D=+12.2±0.5° (CH₃OH, c=1.00, 23° C.). mp. 119-125° C.

[1129] No.3d-10

[1130] [α]_D=+39.7±0.8° (CHCl₃, c=1.07, 22° C.).

[1131] No.3d-11

[1132] [α]_D=+29.2±0.7° (CHCl₃, c=1.06, 22° C.).

[1133] No.3d-12

[1134] [α]_D=+76.4±1.1° (CH₃OH, c=1.03, 24° C.).

[1135] No.3d-14

[1136] [α]_D=−20.6±0.6° (CHCl₃, c=1.07, 22° C.).

[1137] No.3d-15

[1138] [α]₃₆₅=−28.0±0.7° (CH₃OH, c=1.03, 24.5° C.).

[1139] No.3d-16

[1140] [α]_D=−8.7±0.5° (CHCl₃, c=1.06, 22° C.).

[1141] No.3d-17

[1142] CDCl₃300 MHz; 0.80-2.15(m, 24H), 2.32(t, J=7 Hz, 2H), 2.68(t, J=7 Hz, 2H), 3.02(m, 1H), 2.15(m, 24H), 2.32(t, J=7 Hz, 2H), 2.68(t, J=7 Hz, 2H), 3.02(m, 1H), 5.22(m, 2H), 5.38(d, J=7 Hz, 1H), 7.30(A2B2q-Apart, J=8 Hz, 2H), 7.81(A2B2qBpart, J=8 Hz, 2H), 9.86(brs, 1H). [α]₃₆₅=−9.7±0.5° (CHCl₃, c=1.03, 22° C.).

[1143] No.3d-24

[1144] [α]_D=+19.2±0.6° (CHCl₃, c=1.05, 23° C.).

[1145] No.3d-26

[1146] CD₃OD 300 MHz; 0.90-2.20(20H, m), 2.88(1H, m), 3.07(2H, q, J=7.0 Hz), 5.00-5.40(2H, m), 7.20-7.60(4H, m), 7.95(1H, m). IR (KBr): 3415, 3254, 1698, 1564, 1314, 1154/cm.

[1147] No.3d-28

[1148] CD₃OD 300 MHz; 0.90-2.20(20H, m), 2.73(2H, q, J=7.0 Hz), 2.93(1H, m), 5.00-5.30(2H, m), 7.40-7.50(2H, m), 7.60-7.77(2H, m). IR (KBr): 3435, 3280, 1562, 1323, 1304, 1151/cm.

[1149] No.3d-30

[1150] Elemental analysis (C₂₀H₂₅BrNO₄SNa); Calcd.: C, 50.21; H, 5.27; Br, 16.70; N,2.93; S, 6.70; Na4.81 Found: C, 50.22; H, 5.40; Br, 15.57; N, 2.88; S, 6.41; Na5.10 IR (KBr): 3425, 3280, 3085, 1697, 1570, 1410, 1321, 1165, 1155/cm.

[1151] No.3e-1

[1152] CD₃OD 300 MHz; 0.71(1H, d, J=10.2 Hz), 1.04(3H, s), 1.12(3H, s), 1.35-2.28(14H, m), 2.42(3H, s), 3.17-3.25(1H, m), 5.18-5.39(2H, m), 7.37(2H, d, J=8.4 Hz), 7.75(2H, d, J=8.4 Hz). IR (CHCl₃): 3400, 3289, 2986, 2924, 2870, 1559, 1424, 1322, 1305, 1160, 1095, 1075, 1030/cm. [α]_D=+25.9±0.7° (CH₃OH, c=1.00, 23° C.).

[1153] Compounds prepared in Examples above were tested for the in vivo and in vitro activity according to the method shown in Experimental examples below.

[1154] (1) Preparation of Human Platelet Membrane Fraction

[1155] Blood sample was obtained using a plastic syringe containing 3.8% sodium citrate from a venous of healthy volunteers (adult male and female), put into a plastic test tube and mixed gently by inversion. The sample was the n centrifuged at 1800 rpm, 10 min at room temperature, and supernatant containing PRP (platelet rich plasma) was collected. The PRP was re-centrifuged at 2300 rpm, 22 min at room temperature to obtain platelets. The platelets were homogenized using a homogenizer (Ultra-Turrax) followed by centrifugation 3 times at 20,000 rpm, 10 min at 4° C. to obtain platelet membrane fraction. After protein determination, the membrane fraction was adjusted to 2 mg/ml and preserved in a refrigerator at −80° C. until use.

[1156] (2) Binding to PGD₂Receptor

[1157] To a binding-reaction solution (50 mM Tris/HCl, pH 7.4, 5 mM MgCl₂) (0.2 ml) were added human platelet membrane fraction (0.1 mg) and 5 nM [³H]PGD₂(115 Ci/mmol), and reacted at 4° C. for 90 min. After the reaction completed, the reaction mixture was filtered through the glass fiber filter paper, washed several times with cooled saline, and measured radioactivity retained on the filter paper. The specific binding was calculated by subtracting the non-specific binding (the binding in the presence of 10 μM PGD₂) from the total binding. The binding-inhibitory activity of each compound was expressed as concentration required for 50% inhibition (IC₅₀), which was determined by depicting a substitution curve by plotting the binding ratio (%) in the presence of each compound, where the binding ratio in the absence of a test compound is 100%. The results are shown in Table below.

[1158] Peripheral blood was obtained from a healthy volunteer using a syringe in which 1/9 volume of citric acid/dextrose solution has been previously added. The syringe was subjected to centrifugation at 180 g for 10 min to obtain the supernatant (PRP: platelet rich plasma). The resultant RRP was washed 3 times with a washing buffer and the number of platelet was counted with a micro cell counter. A suspension adjusted to contain platelet at a final concentration of 5×10⁸/ml was warmed at 37° C., and then subjected to the pretreatment with 3-isobutyl-1-methylxanthine (0.5 mM) for 5 min. To the suspension was added a test compound diluted at various concentration. Ten-minute later, the reaction was induced by the addition of 0.1-2.0 μM PGD, and, 15-minute later, stopped by the addition of HCl. The platelet was destroyed with an ultrasonic homogenizer. After centrifugation, the cAMP in the supernatant was determined by radioassay. PGD₂receptor antagonism of a drug was evaluated as follows. The inhibition rate regarding CAMP increased by the addition of PGD, was determined at individual concentration, and then the concentration of the drug required for 50% inhibition (IC₅₀) was calculated. The results are shown in Table below.

[1159] The method used for measuring the nasal cavity resistance and evaluating the anti-nasal occlusion using a guinea pig are described below.

[1160] A 1% ovalbumin (OVA) solution was treated with ultrasonic nebulizer to obtain an aerosol. Hartley male guinea pig was sensitized by inhaling twice the aerosol for 10 min at one-week interval. Seven-day after the sensitization, the guinea pig was exposed to an antigen to initiate the reaction. Then the trachea was incised under the anesthesia with pentobarbital (30 mg/kg, i.p.) and cannulas were inserted into the trachea at the pulmonary and nasal cavity sides. The canal inserted at the pulmonary side was connected with an artificial respirator that provides 4 ml air 60 times/min. After arresting the spontaneous respiration of a guinea pig with Garamin (2 mg/kg, i.v.), air was supplied to the snout side with an artificial respirator at the frequency of 70 times/min, and the flow rate of 4 ml air/time, and the atmospheric pressure required for the aeration was measured by the use of a transducer fitted at the branch. The measurement was used as a parameter of the nasal cavity resistance. The exposure of an antigen was carried out by generating aerosol of 3% OVA solution for 3 min between the respirator and nasal cavity cannula. The test drug was injected intravenously 10 min before the antigen exposure. The nasal resistance between 0 to 30 min was measured continuously and the effect was expressed as inhibition rate to that obtained for vehicle using the AUC for 30 min (on the vertical axis, nasal cavity resistance (cm H₂O), and on the horizontal axis, time (0-30 min)) as an indication. The result is shown below.

[1161] Tablets each containing 40 mg of active ingredient were prepared in a conventional manner. The ingredients for 40 mg tablet are as follows:

[1162] Calcium (+)-(Z)-7-[(1R,2S,3S,4S)-3-benzenesulfonamidobicyclo[2.2.1]hept-2-yl]-

[1163] Ingredients:

[1164] Calcium (+)-(Z)-7-[(1R,2S,3S,4S)-3-benzenesulfonamidobicyclo[2.2.1]hept-2-yl]-