9-Deoxy-9-methylene-PGF compounds
AssigneeThe Upjohn Company
InventorGordon L. Bundy
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Abstract
This invention comprises certain analogs PGE or 11-deoxy-PGE compounds in which the carbonyl at C-9 is replaced by methylene. Also provided in this invention, are novel chemical processes and novel chemical intermediates 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.
Claims226
A prostaglandin analog of the formula:
- ##STR41## wherein Y.sub.1 is trans--CH.dbd.CH--, --C.tbd.C--, or --CH.sub.2 CH.sub.2 --;
- wherein M.sub.1 is ##STR42## wherein R.sub.5 is hydrogen or methyl;
- wherein L.sub.1 is ##STR43## or a mixture of ##STR44## 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 Z.sub.7 is
- 1. cis--CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --,
- 2. cis--CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.g --CF.sub.2 --,
- 3. cis--CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.g --CH.sub.2 --,
- 4. --(ch.sub.2).sub.3 --(ch.sub.2).sub.g --CH.sub.2 --,
- 5. --(ch.sub.2).sub.3 --(ch.sub.2).sub.g --CF.sub.2 --,
- 6. --ch.sub.2 --o--ch.sub.2 --(ch.sub.2).sub.g --CH.sub.2 --,
- 7. --c.tbd.c--ch.sub.2 --(ch.sub.2).sub.g --CH.sub.2 --, or
- --CH.sub.2 --C.tbd.C--(CH.sub.2).sub.g --CH.sub.2 --,
- wherein g is one, 2, or 3;
- wherein m is one to 5, inclusive;
- 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.
Dependencies are inferred from the claim text.