13,14-Didehydro-9-deoxy-9-methylene-19-oxo-PGF2 compounds

Claim 1

A compound of the formula ##STR2## wherein D is (1) cis--CH═CH--CH 2 --(CH 2 ) g --CH 2 --, (2) cis--CH═CH--CH 2 --(CH 2 ) g --CF 2 --, (3) cis--CH 2 --CH═CH--CH 2 --CH 2 --, or (4) trans--(CH 2 ) 3 --CH═CH--; wherein g is zero, one, two, or three; wherein Q is α--OH:β--R 5 or α--R 5 :β--OH, wherein R 5 is hydrogen or methyl; wherein R 6 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 groups of one to 3 carbon atoms, inclusive, (g) --(p--Ph)--CO--CH 3 , (h) --(p--Ph)--NH--CO--(p--Ph)--NH--CO--CH 3 , (i) --(p--Ph)--NH--CO--(p--Ph), (j) --(p--Ph)--NH--CO--CH 3 , (k) --(p--Ph)--NH--CO--NH 2 , (l) --(p--Ph)--CH═N--NH--CO--NH 2 , (m) β-naphthyl, (n) --CH 2 --CO--R 28 , wherein (p--Ph) is para-phenyl or inter-para-phenylene, wherein R 28 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, or (o) a pharmacologically acceptable cation; wherein R 3 and R 4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R 3 and R 4 is fluoro only when the other is hydrogen or fluoro; and wherein X is --C.tbd.C--.