US 4,105,682 AGrant
13,14-Dihydro-9-deoxy-PGF.sub.2 Compounds
Issue Date:1978-08-08
•25 Claims
Abstract
Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins.
Metadata
Assignee
- The Upjohn Company
Inventor
- Gordon L. Bundy
Application Information
Application Number:US 7866992
Filing Date:1977-04-11
Priority Date:1975-09-17
Art Unit:126
Classifications
IPC:
C07C17700
Field of Search:
260560514 D;408;410;410.5;410.9 R;413121
Patent Drawings
This patent does not have any drawings.
Description
The present invention relates to prostaglandin analogs for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,033,989, issued July 5, 1977.
Claims
I claim:
1. A prostaglandin analog of the formula ##STR2## wherein m is one to 5, inclusive; wherein M.sub.1 is ##STR3## 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.1 is ##STR4## or a mixture of ##STR5## wherein R.sub.3 and R.sub.4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R.sub.3 and R.sub.4 is fluoro only when the other is hydrogen or fluoro; 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 one, two, or three chloro or alkyl of one to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation; and Wherein Z.sub.6 is (1) cis--CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.g --CF.sub.2 -- or (2) cis--CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --, wherein g is one, 2, or 3.
2. A compound according to claim 1, wherein M.sub.1 is ##STR6##
3. A compound according to claim 1, wherein M.sub.1 is ##STR7##
4. A compound according to claim 3, wherein m is 3.
5. A compound according to claim 4, wherein Z.sub.6 is
6. A compound according to claim 5, wherein g is 3.
7. A compound according to claim 5, wherein g is one.
8. A compound according to claim 7, wherein R.sub.5 and R.sub.6 are both hydrogen.
9. A compound according to claim 8, wherein R.sub.3 and R.sub.4 are both hydrogen.
10. 13,14-Dihydro-9-deoxy-PGF.sub.2, a compound according to claim 9.
11. A compound according to claim 8, wherein R.sub.3 and R.sub.4 are both fluoro.
12. 16,16-Difluoro-13,14-dihydro-9-deoxy-PGF.sub.2, a compound according to claim 11.
13. A compound according to claim 4, wherein Z.sub.6 is
14. A compound according to claim 13, wherein g is 3.
15. A compound according to claim 14, wherein R.sub.5 and R.sub.6 are both hydrogen.
16. A compound according to claim 15, wherein R.sub.3 and R.sub.4 are both hydrogen.
17. 2a,2b-Dihomo-2,2-difluoro-13,14-dihydro-9-deoxy-PGF.sub.2, a compound according to claim 15.
18. A compound according to claim 15, wherein R.sub.3 and R.sub.4 are both fluoro.
19. 2a,2 b-Dihomo-16,16-difluoro-2,2-difluoro-13,14-dihydro-9-deoxy-PGF.sub.2, a compound according to claim 17.
20. A compound according to claim 13, wherein g is one.
21. A compound according to claim 20, wherein R.sub.5 and R.sub.6 are both hydrogen.
22. A compound according to claim 21, wherein R.sub.3 and R.sub.4 are both hydrogen.
23. 2,2-Difluoro-13,14-dihydro-9-deoxy-PGF.sub.2, a compound according to claim 22.
24. A compound according to claim 21, wherein R.sub.3 and R.sub.4 are both fluoro.
25. 2,2,16,16-Tetrafluoro-13,14-dihydro-9-deoxy-PGF.sub.2, a compound according to claim 24.
Patent Citations (1)
| Patent | Date | Inventor | Cited By |
|---|---|---|---|
| US3894009 | 1975-07-01 | Sakai et al. |