13,14-Dihydro-9.beta.-PGD.sub.2 compounds

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 the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.

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. 4,016,184, issued April 5, 1977.

Claims

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, or 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 --,

(2) cis-CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --, or

(3) cis-CH.sub.2 --CH.dbd.CH--(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

cis-CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --.

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.beta.-PGD.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.beta.-PGD.sub.2, a compound according to claim 11.

13. A compound according to claim 4, wherein Z.sub.6 is

cis-CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.6 --CH.sub.2 --.

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-cis-4,5-didehydro-13,14-dihydro-9.beta.-PGD.sub.1, a compound according to claim 16.

18. A compound according to claim 15, wherein R.sub.3 and R.sub.4 are both fluoro.

19. 2a,2b-Dihomo-16,16-difluoro-cis-4,5-didehydro-13,14-dihydro-9.beta.-PDG.sub.1, a compound according to claim 18.

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. cis-4,5-Didehydro-13,14-dihydro-9.beta.-PGD.sub.1, 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. 16,16-Difluoro-cis-4,5-didehydro-13,14-dihydro-9.beta.-PGD.sub.1, a compound according to claim 24.