19-Hydroxy-PGI2 compounds

Claim 1

A prostacyclin-type compound of the formula wherein A 1 is --O--(oxa) and E 1 is --CH 2 -- wherein L 1 is (1) --(CH 2 ) n -- wherein n is one to 5, inclusor (2) --(CH 2 ) p --CF 2 -- wherein P is 2, 3, or 4, wherein M 1 is ##STR48## wherein ˜ indicates attachment in alpha or beta configuration, wherein Q is ##STR49## wherein R 4 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R 1 is (1) --COOR 3 (2) --CH 2 OH (3) --CH 2 N(R 7 )(R 8 ) ##STR50## 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 groups of one to 3 carbon atoms, inclusive; ##STR51## wherein R 16 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, or (o) a pharmacologically acceptable cation; wherein R 7 and R 8 are hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different, and wherein R 15 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl groups of one to 3 carbon atoms, inclusive, or phenyl substituted with hydroxycarbonyl or alkoxycarbonyl of one to 4 carbon atoms, inclusive, wherein R 2 is hydrogen, hydroxyl, or hydroxymethyl, 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-- or (4) --CH 2 CH 2 --.