US 4,122,100 AGrant
Cis-4,5-didehydro-11-deoxy-PGF.sub.1 Analogs
Issue Date:1978-10-24
•18 Claims
Abstract
This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
Metadata
Assignee
- The Upjohn Company
Inventor
- Ernest W. Yankee
Application Information
Application Number:US 7740859
Filing Date:1977-03-03
Priority Date:1975-07-14
Art Unit:126
Classifications
IPC:
C07C17700
Field of Search:
260560468 D;514 D;408;410;410.5;410.9R;413121
Patent Drawings
This patent does not have any drawings.
Description
The present invention relates to prostaglandin analogos for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,026,909, issued May 31, 1977.
Claims
I claim:
1. A compound of the formula ##STR1## wherein Y.sub.1 is cis-CH.dbd.-CH--; wherein g is 2, 3, or 4; WHEREIN M.sub.1 is ##STR2## wherein R.sub.5 and R.sub.6 are hydrogen or methyl, with the proviso that one of R.sub.5 and R.sub.6 is methyl only when the other is hydrogen; Wherein L.sub.2 is ##STR3## or a mixture of ##STR4## WHEREIN R.sub.3 and R.sub.4 are hydrogen or fluoro, being the same or different, with the proviso that at least one of R.sub.3 and R.sub.4 is fluoro; Wherein m is 1 to 5, inclusive; and Wherein R.sub.1 is hydrogen, alkyl of 1 to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation.
2. A compound according to claim 1, wherein g is 4.
3. A compound according to claim 2, wherein m is 3.
4. A compound according to claim 3, wherein R.sub.3 and R.sub.4 are both fluoro.
5. A compound according to claim 4, wherein R.sub.5 and R.sub.6 are hydrogen.
6. 15-EPI- 2A,2B-Dihomo-16,16-difluoro-cis-4,5-didehydro-11-deoxy-cis-13-PGF.sub.1.alp ha., methyl ester, a compound according to claim 5.
7. A compound according to claim 1, wherein g is 2.
8. A compound according to claim 7, wherein m is 3.
9. A compound according to claim 8, wherein both R.sub.3 and R.sub.4 are fluoro.
10. A compound according to claim 9, wherein R.sub.5 and R.sub.6 are hydrogen.
11. 15-epi -16,16-difluoro-cis-4,5-didehydro-11-deoxy-cis-13-PGF.sub.1.alpha., methyl ester, a compound according to claim 10.
12. A compound of the formula ##STR5## wherein Y.sub.1 is cis-CH.dbd.CH--; wherein g is 2, 3, or 4; wherein M.sub.2 is ##STR6## wherein L.sub.3 is ##STR7## or a mixture of ##STR8## wherein R.sub.3 and R.sub.4 are hydrogen or methyl, being the same or different; wherein m is 1 to 5, inclusive; and wherein R.sub.1 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with 1, 2, or 3 chloro or alkyl of 1 to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation.
13. A compound according to claim 12, wherein g is 2.
14. A compound according to claim 13, wherein m is 3.
15. A compound according to claim 14, wherein at least one of R.sub.3 and R.sub.4 is methyl.
16. A compound according to claim 15, wherein R.sub.3 and R.sub.4 are both methyl.
17. A compound according to claim 14, wherein R.sub.3 and R.sub.4 are hydrogen.
18. 15-epi-cis-4,5-didehydro-11-deoxy-cis-13-PGF.sub.1.alpha., methyl ester, 15-methyl ether, a compound according to claim 17.
Patent Citations (1)
| Patent | Date | Inventor | Cited By |
|---|---|---|---|
| US3932479 | 1976-01-01 | Bernady et al. |