Phenyl-substituted prostaglandin-F type analogs

An optically active compound of the formula ##SPC59##

• or a racemic compound of that formula and the mirror image thereof, wherein E is -CH.sub.2 CHR.sub.4 - or trans-CH=CR.sub.4 -:
• wherein R.sub.1 is hydrogen, alkyl of one to 8 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl-substituted with one, 2, or 3 chloro or alkyl or one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro;
• wherein M is ##EQU10## or ##EQU11## wherein R.sub.2, R.sub.3, and R.sub.4 are hydrogen or alkyl of one to 4 carbon atoms, inclusive;
• wherein C.sub.t H.sub.2t represents a valence bond or alkylene of one to 10 carbon atoms, inclusive, substituted with zero, one, or 2 fluoro, with one to 7 carbon atoms, inclusive, between ##EQU12## and the phenyl ring;
• wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or -OR.sub.9, wherein R.sub.9 is hydrogen, or alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl;
• wherein V is (a) alkylene of 3 to 12 carbon atoms, inclusive, substituted with zero, one, 2, 3 or 4 fluoro, with 3 to 7 carbon atoms, inclusive, between -CHR.sub.2 - and COOR.sub.1, with the proviso that when 3 or 4 fluoro are present, they are all substituents of the carbon atoms alpha and beta to -COOR.sub.1, (b) -CH=CH-A-, cis or trans, or (c) -C.tbd.C-A-, wherein A is alkylene of one to 10 carbon atoms, inclusive, substituted with zero, one, 2, 3, or 4 fluoro, with one to 5 carbon atoms, inclusive, between =CH- (or .tbd.C-) and -COOR.sub. 1, with the proviso that when 3 or 4 fluoro are present, they are all substituents of the carbon atoms alpha and beta to -COOR.sub.1, with the further proviso that when E is -CH.sub.2 -CHR.sub.4 - V is (a) above;
• and wherein .about. indicates attachment of the group to the cyclopentane ring in alpha or beta configuration;
• including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.