6-Keto prostaglandin E-type compounds

Claim 1

A compound of the formula ##STR144## or a mixture comprising that compound and the enantiometer thereof wherein D is (1) --(CH 2 ) 3 --C(R 2 ) 2 -- (2) --CH 2 --O--CH 2 --Y-- or (3) --CH 2 CH═CH-- wherein d is zero to 5, R 2 is hydrogen, methyl, or fluoro, being the same or different with the proviso that one R 2 is not methyl when the other is fluoro, and Y is a valence bond, --CH 2 -- or --(CH 2 ) 2 --, wherein Q is ##STR145## wherein R 8 is hydrogen, methyl, or ethyl, wherein R 3 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, (c) cycloalkyl of 3 to 10 carbon atoms, inclusive, (d) aralkyl of 7 to 12 carbon atoms, inclusive, (e) phenyl, (f) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR146## wherein R 10 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R 11 is hydrogen or benzoyl, or (n) a pharmacologically acceptable cation, wherein R 18 is ##STR147## wherein R 38 is ##STR148## wherein C g H 2g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR 5 R 6 -- and terminal methyl, wherein R 5 and R 6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R 5 and R 6 is fluoro only when the other is hydrogen or fluoro, and wherein X is (1) trans--CH═CH-- (2) cis--CH═CH-- (3) --C.tbd.C-- (4) --CH 2 CH 2 --, including the lower alkanoates thereof.