2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-PGF compounds

Abstract

The present specification relates to novel 9-deoxy-9-methylene-trans-2,3-didehydro-PGF compounds with improved pharmacological properties. While these compounds are useful in inducing a wide variety of prostaglandin-like pharmacological effects, they are specifically useful as regulators of procreation and fertility.

Description

Claims

1. A prostaglandin analog of the formula ##STR1## wherein Y.sub.1 is trans-CH.dbd.CH-, -C.tbd.C-, --CH.sub.2 CH.sub.2 --, or cis-CH.dbd.CH-;

wherein M.sub.1 is ##STR2## wherein R.sub.5 is hydrogen or methyl; wherein L.sub.1 is ##STR3## 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 g is 4, 5, or 6;

wherein R.sub.7 is ##STR4## wherein h is zero, one, two, or three, wherein m is one to 5, inclusive, 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, with the further proviso that R.sub.7 is ##STR5## wherein T and s are as defined above, only when R.sub.3 and R.sub.4 are hydrogen or methyl, being the same or different.

2. A prostaglandin analog according to claim 1, wherein R.sub.7 is ##STR6##

3. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-17-phenyl-18, 19,20-trinor-PGF.sub.1, a prostaglandin analog according to claim 2.

4. A prostaglandin analog according to claim 1, wherein R.sub.7 is ##STR7##

5. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1, a prostaglandin analog according to claim 4.

6. A prostaglandin analog according to claim 1, wherein R.sub.7 is -(CH.sub.2).sub.m -CH.sub.3.

7. A prostaglandin analog according to claim 6, wherein m is 3.

8. A prostaglandin analog according to claim 7, wherein g is 4.

9. A prostaglandin analog according to claim 8, wherein Y.sub.1 is -C.tbd.C-.

10. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-13,14-didehydro-PGF.sub.1, a prostaglandin analog according to claim 9.

11. A prostaglandin analog according to claim 8, wherein Y.sub.1 is -CH.sub.2 CH.sub.2 -.

12. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-13,14-dihydro-PGF.sub.1, a prostaglandin analog according to claim 11.

13. A prostaglandin analog according to claim 8, wherein Y.sub.1 is trans-CH.dbd.CH-.

14. A prostaglandin analog according to claim 13, wherein at least one of R.sub.3 and R.sub.4 is fluoro.

15. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-16,16-difluoro-PGF.sub.1, a prostaglandin analog according to claim 14.

16. A prostaglandin analog according to claim 13, wherein at least one of R.sub.3 and R.sub.4 is methyl.

17. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-16,16-dimethyl-PGF.sub.1, a prostaglandin analog according to claim 16.

18. A prostaglandin analog according to claim 13, wherein R.sub.3 and R.sub.4 are both hydrogen.

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

20. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-15-methyl-PGF.sub.1, a prostaglandin analog according to claim 19.

21. A prostaglandin analog according to claim 20, wherein R.sub.5 is hydrogen.

22. 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-PGF.sub.1, a prostaglandin analog according to claim 21.