Compounds Which Inhibit Complement and/or Suppress Immune Activity

Patent Citations (18)

Non-Patent Literature (90)

• Bradbury and Sindelar, 1986, "Regioselective metalation in the synthesis of partial derivatives of the complement inhibitor K-76," Abstract No. 14, p. 24, 13th Annual MALTO Medicinal Chemistry/Pharmacognosy Meeting-In-Miniature, May 21-23, New Orleans, La.
• Hong et al., 1979, "An anti-complementary agent, K-76 monocarboxylic acid: Its site and mechanism of inhibition of the complement activation cascade," J. Immunol., 122:2418.
• Hong et al., 1981, "Inhibitory effect of K-76 monocarboxylic acid, an anticomplementary agent, on the C3b, inactivator system," J. Immunol., 127:104.
• Hong et al., 1981, "Simple methods for preparing EAC1, 4b, 2a, 3b, and EAC4b, 3b with human or guinea pig complement components using an anticomplementary agent, K-76 monocarboxylic acid," J. Immunol., 127:109.
• Bumpers and Baum, 1983, "The effect of a novel C5 inhibitor (K-76 CONNa) on tumor cell chemotaxis,"]J. Lab. Clin. Med., 102:421.
• Konno and Tsunifugi, 1983, "Induction of zymosan air pouch inflammation in rats and its characterization with reference to the effects of anticomplementary and anti-inflammatory agents," Dr. J. Pharmacol., 80:269.
• Miyazaki et al., 1983, "Complement inhibitor, K-76 COOH," Farumashia (Japan) 19:912.
• Ramm et al., 1983, "Size distribution and stability of the trans-membrane channels formed by complement complex C5b-9," Mol. Immunol., 20:155.
• Hudig et al., 1984, "Inhibition of human lymphocyte natural cytotoxicity and antibody-dependent cell-mediated cytotoxicity by K-76 COONa, a reagent that blocks complement activity," J. Immunol., 133:408.
• Miyazaki et al., 1984, "Effects of K-76 monocarboxylic acid, an anticomplementary agent, in various in vivo immunological reactions and on experimental glomerulonaphritis,"]Complement 1:134.
• Rudelman et al., 1984, "The mechanism of cell-mediated cytotoxicity, II. K-76 COONa, which inhibits the activity of Factor I and CS, inhibits early events in cytotoxic T-lymphocyte-mediated cytolysis and in T-lymphocyte activation," Cell Immunol., 88:16.
• Konno and Tsurufugi, 1985, "Inhibitory effect of a novel anti-complementary agent, K-76 COONa, on the release of histamine induced by zymosan and compound 48/80," Jpn. J. Pharmacol., 38:116.
• Redelman et al., 1986, "The induction of T-cell growth factor receptor precedes the reduction of RNA and occurs in the presence of inhibitors of RNA synthesis," Cytometry 7:453.
• Iida et al., 1987, "Effect of the anticomplementary agent, K-76 monocarboxylic acid on experimental immune complex glomerulonephritis in rats," Clin. Exp. Immunol., 67:130.
• Miyazaki et al., 1980, "A complement inhibitor produced by Stachybotrys complementi, nov. sp. K-76, a new species of fungi imperfecti," Microbiol. Immunol., 24(11):1091.
• Kaise et al., 1979, "Structure of K-76, a complement inhibitor produced by Stachybotyrys complementi nov. sp. K-76," J. Chem. Soc. Chem. Commun., 726.
• McMurry and Erion, 1985, "Stereoselective total synthesis of the complement inhibitor K-76," J. Am. Chem. Soc., 107:2712.
• Corey and Das, 1982, "Total synthesis of the complement inhibitor K-76 in racemic form. Structural assignment to K-76 monocarboxylic acid," J. Am. Chem. Soc., 104:5551.
• Spanevello et al., 1982, "Regioselective synthesis of the spiro-benzofuran unit, present in several natural products, by an intramolecular Michael cyclization," Syn. Commun. 16(7):749.
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• Becker, 1967, "The relationship of the structure of phosphonate esters to their ability to inhibit chymotrypsin, trypsin, acetylcholinesterase and C'ia, Biochim. Biophys. Acta., 147:289.
• Bradbury and Sindelar, 1989, "Synthesis of 4,7-disubstituted spirobenzofuran-2(3H)-cyclohexanes," J. Heterocyclic Chem., 26:1827.
• Bult and Herman, 1983, "Inflammatory mediators released by complement-derived peptides," Agents and Actions 13(5/6):405.
• Burge et al., 1978, "Inhibition of the alternative pathway of complement by gold sodium thiomalate in vitro," J. Immunol., 120(5):1625.
• Cavarocchi et al., 1986, "Oxygen free radical generation during cardiopulmonary bypass: correlation with complement activation," Circulation 74(suppl.III):130.
• Crawford et al., 1972, "Metalation of limonene. A novel method for the synthesis of bisabolane sesquiterpenes," J. Am. Chem. Soc., 94:4298.
• Djura and Sargent, 1983, "The structure of isopannarin," Aust. J. Chem., 36:1057-1059.
• Eisen, 1979, "Cell-mediated hypersensitivity and immunity," Immunology Ch. 20, Harper and Row, Hagerstown, Md., pp. 558-595.
• Eisen et al., 1974, "Complement," Immunology Ch. 18, Harper and Row, Publishers Inc., Hagerstown, Md., pp. 512.
• Fuji et al., 1979, "Hard acid and soft nucleophile system. New efficient method for removal of benzyl protecting group," J. Org. Chem., 44(10):1661.
• Fujimoto et al., 1983, "Spontaneous release of the Leu-2 (T8) molecule from human T cells," J. Exp. Med., 159:752.
• Fujita et al., 1976, "Biosynthesis of natural products. Part 1. Incorporation of ent-kaur-16-ene and ent-kaur-16-en-15-one into enmein and oridonin," J. Chem. Soc., 23:2098.
• Glovsky et al., 1969, "Role of fumaropimaric acid in guinea pig complement dependent and non-complement dependent biologic reactions," J. Immunol., 102(1):1.
• Greco et al., 1975, "Model studies directed toward the total synthesis of vernolepin. III. Synthesis of the .alpha.-methylene-.delta.-valerolactone AB ring model," J. Org. Chem., 40(10):1450.
• Hansch and Yoshimoto, 1974, "Structure-activity relationships in immunochemistry. 2. Inhibition of complement by benzamidines," J. Med. Chem., 17(11):1160.
• Hood et al., 1984, "Antigen-bound IgM and IgG antibodies initiate complement fixation," Immunology, 2d ed., The Benjamin/Cummings Publishing Co., Menlo Park, Calif., p. 339.
• Hugli, 1981, "The structural basis for anaphylatoxin and chemotactic functions of C3a, C4a, and C5a," CRC Crit. Rev. Immunol., 1:321.
• Johnson et al., 1975, "Release of histamine from rat mast cells by the complement peptides C3a and C5a," Immunology 28:1067.
• Jolly et al., 1986, "Reduction of myocardial infarct size by neutrophil depletion: Effect of duration of occlusion," Am. Heart J., 112(4):682.
• Kaufman and Sindelar, 1989, "A short and efficient synthesis of grisan," J. Heterocyclic Chem., 26:879.
• Kaufman et al., 1989, ".sup.13 C NMR chemical shifts of the carbon atoms of the methoxymethyl group of di-ortho-substituted aromatic methoxymethyl ethers," J. Heterocyclic Chem. 27:1178.
• Kirklin et al., 1983, "Complement and the damaging effects of the cardiopulmonary bypass," J. Thorac. Cardiovasc. Surg., 86:845.
• Lythgoe et al., 1956, "Calciferol and its relatives. Part II. An alternative synthesis of trans-1,2'cyclohexylidene-ethylidene-2-methylenecyclohexane," J. Chem. Soc., Part IV:4060-4065.
• Meuer et al., 1984, "Triggering of the T3-Ti antigen-receptor complex results in clonal T-cell proliferation through an interleukin 2-dependent autocrine pathway," Proc. Natl. Acad. Sci. USA 81:1509.
• Miescher and Muller-Eberhard, 1976, Text Book of Immunopathology, 2d ed., Vols. I and II, Grune and Stratton, New York.
• Miller et al., 1980, "Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate," J. Med. Chem., 23:242.
• Mori and Komatsu, 1988, "Synthesis of the complement inhibitor (-)-K-76 and of related compounds," Liebigs Ann. Chem., pp. 107-119.
• Muller-Eberhard, 1978, "Complement: Molecular mechanisms, regulation and biologic function," Molecular Basis of Biological Degradative Processes, Berlin, R. D. et al., eds. Academic Press, N.Y., p. 65.
• Narasimhan et al., 1979, "Synthetic application of lithiation reactions; Part XIII. Synthesis of 3-phenylcoumarins and their benzo derivatives," Synthesis, p. 906.
• Rall et al., 1976, "Crown ethers. Application in the synthesis of chalcones," Tetrahedron Letters No. 13, p. 1033.
• Regal and Pickering, 1983, "C5a and antigen-induced tracheal contraction: Effect of a combination of an antihistamine and cyclo-oxygenase inhibitors," Int. J. Immunopharmac. 5(1):71.
• Rossen et al., 1985, "Selective accumulation of the first component of complement and leukocytes in ischemic canine heart muscle," Circulation Research 57(1):119.
• Rubin et al., 1985, "Soluble interleukin-2 receptors are shed by activated human lymphocytes in vitro," (Abstract No. 3131).
• Rubin et al., 1985, "Soluble interleukin 2 receptors are released from activated human lymphoid cells in vitro," J. Immunol., 135(5):3172.
• Sandberg, 1981, "Complement," in Cellular Functions in Immunity and Inflammation, Oppenheim, J. J. et al., eds., Elsevier/North Holland, N.Y., p. 373.
• Schafer et al., 1986, "Deposition of the terminal C5b-9 complement complex in infarcted areas of human myocardium," J. Immunol. 137(6):1945.
• Simpson and Lucchesi, 1987, "Free radicals and myocardial ischemia and reperfusion injury," J. Lab. Clin. Med., 110(1):13.
• Tack et al., 1979, "Fifth component of human complement: Purification from plasma and polypeptide chain structure,"]Biochemistry 18(8):1490.
• Takada et al., 1978, "Inhibition of the classical and alternative pathways by amino acids and their derivatives," Immunology 34:509.
• Tsudo et al., 1984, "Expression of tac antigen on activated normal human B cells," J. Exp. Med., 160:612.
• Vogt et al., 1979, "Interference of propamidine with binding of the fifth component of complement to surface-fixed C3b, and with C5 activation,"]Immunology 36:139.
• Waldmann et al., 1984, "Expression of interleukin 2 receptors on activated human B cells," J. Exp. Med., 160:1450.
• Webster et al., 1980, "Biological effects of the human complement fragments C5a and C5a (desarg) on neutrophil function," Immunopharmacol., 2:201.
• Wheeler and Lerner, 1956, "Structure and Properties of cyclic compounds. III. Dissociation constants of simple .alpha.,.beta.-unsaturated cyclic acids," J. Am. Chem. Soc., 78:63.
• WHO Scientific Group, 1977, "Chemotherapy of solid tumours," WHO Tech. Rep. Ser., 606:3.
• Wissler, 1972, "Chemistry and Biology of the anaphylatoxin related serum peptide system," Eur. J. Immunol., 2:73.
• Bradbury, 1988, "Synthesis of substituted spiro[benzofuran-2(3H)-cyclohexanes] as partial derivatives of the complement inhibitor, K-76," Dissertation Submitted to the Faculty of the University of Mississippi.
• Bradbury and Sindelar, 1987, "Synthesis and evaluation of partial derivatives of the complement inhibitor K-76," 14th Annual Malto Medicinal Chemistry-Pharmacognosy Meeting, May 17-19, Abstract Only.
• Bradbury and Sindelar, 1987, "Synthesis of 4,7-disubstituted spirobenzofuran-2(3H)-cyclohexanes," National American Chemical Society 194th Meeting, Sep. 4, New Orleans, La., Abstract Only.
• Sindelar et al., 1990, "Potential complement inhibitors blocking release of C5a based on a natural product model," American Chemical Society Division of Medicinal Chemistry, 200th ACS National Meeting, Aug. 26-31, Washington, D.C., Abstract No. 178.
• Sindelar et al., 1989, "Synthesis and evaluation of B/C/D-ring analogues of the anti-complement natural product K-76," American Chemical Society National 198th Meeting September 10, Miami, Fla., Abstract No. 35.
• Sindelar et al., 1988, "Synthesis of A/C/D-ring analogues of the anticomplement natural product K-76," American Chemical Society 196th National Meeting, Sep. 29, Los Angeles, Calif., Abstract only.
• Sindelar et al., 1988, "Synthesis and evaluation of B/C/D-ring analogues of the natural product complement inhibitor K-76," American Association of Pharmaceutical Scientists, AAPS Meeting Nov. 2, Orlando, Fla., Abstract Only.