5,6-Didehydro-.omega.-phenoxy-PGE.sub.2.alpha. analogs

Abstract

This invention comprises certain analogs of the prostaglandins in which there is a triple bond between C-5 and C-6 or C-4 and C-5. Also provided in this invention, are novel chemical processes 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.

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. 4,013,695, issued Mar. 22, 1977.

Claims

1. A prostaglandin analog of the formula ##STR1## WHEREIN G IS ONE, 2, OR 3; WHEREIN Y is trans--CH.dbd.CH--;

wherein M.sub.1 is

R.sub.5 OH

or

R.sub.5 OH,

wherein R.sub.5 is hydrogen or methyl;

Wherein T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, and s is zero, one, 2, or 3, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl;

Wherein L.sub.1 is

R.sub.3 R.sub.4,

r.sub.3 r.sub.4,

or a mixture of

R.sub.3 R.sub.4

and

R.sub.3 R.sub.4,

wherein R.sub.3 and R.sub.4 are hydrogen or methyl being the same or different; 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 one, two or three chloro or alkyl of one to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation.

2. A compound according to claim 1, wherein M.sub.1 is

R.sub.5 OH.

3. A compound according to claim 1, wherein M.sub.1 is

R.sub.5 OH.

4. A compound according to claim 3, wherein g is 3.

5. A compound according to claim 4, wherein m is 3.

6. A compound according to claim 5, wherein R.sub.3, R.sub.4, and R.sub.5 are all hydrogen.

7. 2A,2B-Dihomo-5,6-didehydro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., methyl ester, a compound according to claim 6.

8. A compound according to claim 3, wherein g is one.

9. A compound according to claim 8, wherein m is 3.

10. A compound according to claim 9, wherein R.sub.3 and R.sub.4 are both hydrogen.

11. A compound according to claim 10, wherein R.sub.5 is methyl.

12. 5,6-Didehydro-15-methyl-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., methyl ester, a compound according to claim 11.

13. 5,6-Didehydro-15-methyl-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 11.

14. A compound according to claim 10, wherein R.sub.5 is hydrogen.

15. 5,6-Didehydro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1a, a compound according to claim 14.

16. 5,6-Didehydro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., methyl ester, a compound according to claim 14.

17. A compound according to claim 9, wherein at least one of R.sub.3 and R.sub.4 is methyl.

18. A compound according to claim 17, wherein R.sub.3 and R.sub.4 are both methyl.

19. A compound according to claim 18, wherein R.sub.5 is methyl.

20. 5,6-Didehydro-15,16-dimethyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 19.

21. 5,6-Didehydro-15,16-dimethyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha., methyl ester, a compound according to claim 19.

22. A compound according to claim 18, wherein R.sub.5 is hydrogen.

23. 5,6-Didehydro-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 22.

24. 5,6-Didehydro-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha., methyl ester, a compound according to claim 22.