Aliphatic 2-decarboxy-2-hydroxymethyl-13,14-didehydro-PG compounds
AssigneeThe Upjohn Company
InventorHerman W. Smith
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Abstract
This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. 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.
Claims154
A prostaglandin analog of the formula:
- ##STR150## wherein R.sub.8 is hydrogen or hydroxy;
- wherein M.sub.1 is ##STR151## wherein R.sub.5 is hydrogen or methyl;
- wherein L.sub.1 is ##STR152## or a mixture of ##STR153## 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 --, or
- (6) --CH.sub.2 --O--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --,
- wherein g is one, 2, or 3;
- and
- wherein m is one to 5, inclusive.
Dependencies are inferred from the claim text.