Cis-13-9-deoxy-9,10-didehydro-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 Apr. 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 outer 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 --,

(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 g is 3.

6. 2a,2b-Dihomo-9-deoxy-9,10-didehydro-15-epi-cis-13-PGD.sub.2, a compound according to claim 5.

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

8. 9-Deoxy-9,10-didehydro-15-epi-cis-13-PGD.sub.2, a compound according to claim 7.

9. cis-4,5-Didehydro-9-deoxy-9,10-didehydro-15-epi-cis-13-PGD.sub.1, a compound according to claim 7.