4,5-Cis-didehydro-PGE.sub.1 analogs
AssigneeThe Upjohn Company
InventorBarney J. Magerlein
Life of this patent
Estimating the term…
Abstract
This invention is a group of 4,5-didehydro PG.sub.1 (prostaglandin-type) analogs having variable chain length, branching and fluoro substitution in the hydroxy-substituted side-chain, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.
Claims22
An optically active compound of the formula ##STR2## or a racemic compound of that formula and the mirror image thereof, wherein M is ##STR3## wherein R.sub.5 is hydrogen, methyl, or ethyl;
- and wherein R.sub.1 is hydrogen or 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, or phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive;
- including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
An optically active compound of the formula ##STR5## or a racemic compound of that formula and the mirror image thereof, wherein M is ##STR6## wherein R.sub.5 is hydrogen, methyl, or ethyl;
- wherein R.sub.1 is hydrogen or 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, or phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive;
- wherein R.sub.2 is alkyl of 2 to 4 carbon atoms, inclusive, substituted with one or 2 fluoro;
- and wherein E is trans--CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --;
- including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
An optically active compound of the formula ##STR7## or a racemic compound of that formula and the mirror image thereof, wherein M is ##STR8## wherein R.sub.5 is hydrogen, methyl, or ethyl;
- wherein R.sub.1 is hydrogen or 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, or phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive;
- wherein R.sub.3 is alkyl of 5 carbon atoms substituted with one or 2 fluoro;
- and wherein E is trans--CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --;
- including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
An optically active compound of the formula ##STR9## or a racemic compound of that formula and the mirror image thereof, wherein M is ##STR10## wherein R.sub.5 is hydrogen, methyl, or ethyl;
- wherein R.sub.1 is hydrogen or 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, or phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.4 is alkyl of 6 to 10 carbon atoms, inclusive, substituted with one or 2 fluoro;
- and wherein E is trans--CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --;
- including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
Dependencies are inferred from the claim text.