2-Decarboxy-2-hydroxymethyl-deoxy-9,10-didehydro-PGD.sub.2 analogs

Abstract

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. 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 disclosure therefor is incorporated by reference here from Serial No. 647,369, filed January 8, 1976, now pending issuance as a United States Patent.

Claims

1. A prostaglandin analog of the formula ##STR1## wherein M.sub.1 is ##STR2## wherein R.sub.5 is hydrogen or methyl;

wherein L.sub.1 is ##STR3## or a mixture of ##STR4## 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 methyl only when the other is hydrogen or methyl;

wherein g is one, 2, or 3; and

wherein m is one to 5, inclusive;

with the proviso that at least one of R.sub.3, R.sub.4, and R.sub.5 is methyl or at least one of R.sub.3 and R.sub.4 is fluoro.

2. A compound according to claim 1, wherein m is one or 2.

3. A compound according to claim 1, wherein m is 4 or 5.

4. A compound according to claim 1, wherein m is 3.

5. A compound according to claim 4, wherein g is one.

6. A compound according to claim 5, wherein at least one of R.sub.3 and R.sub.4 is fluoro.

7. A compound according to claim 6, wherein R.sub.3 and R.sub.4 are both fluoro.

8. A compound according to claim 7, wherein R.sub.5 is hydrogen.

9. 2-Decarboxy-2-hydroxymethyl-16,16-difluoro-9-deoxy-9,10-didehydro-PGD.sub.2, a compound according to claim 8.

10. A compound according to claim 5, wherein at least one of R.sub.3 and R.sub.4 is methyl.

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

12. A compound according to claim 11, wherein R.sub.5 is hydrogen.

13. 2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-9-deoxy-9,10-didehydro-PGD.sub.2, a compound according to claim 12.

14. A compound according to claim 5, wherein R.sub.3 and R.sub.4 are hydrogen and R.sub.5 is methyl.

15. 2-Decarboxy-2-hydroxymethyl-15-methyl-9-deoxy-9,10-didehydro-PGD.sub.2, a compound according to claim 14.