19-Hydroxy-19-methyl-PGI.sub.1 compounds

A prostacyclin-type compound of the formula ##STR3## wherein A.sub.1 is --O-- (oxa) and E.sub.1 is --CH.sub.2 wherein L.sub.1 is

• (1) --(CH.sub.2).sub.n --, wherein n is one to 5, inclusive,
• (2) --(CH.sub.2).sub.p --CF.sub.2 --, wherein p is 2, 3, or 4, or
• (3) --CH.sub.2 --CH.dbd.CH--;
• wherein M.sub.1 is ##STR4## wherein Q is oxo, .alpha.-H:.beta.-H, .alpha.-OH:.beta.-R.sub.4, or .alpha.-R.sub.4 :.beta.-OH,
• wherein R.sub.4 is hydrogen or alkyl of one to 4 carbon atoms, inclusive,
• wherein R.sub.1 is
• (1) --COOR.sub.3,
• (2) --CH.sub.2 OH,
• (3) --CH.sub.2 N(R.sub.7)(R.sub.8),
• (4) --CO--N(R.sub.7)(R.sub.8),
• (5) --CO--NH--SO.sub.2 --R.sub.15, or
• (6) tetrazolyl,
• wherein R.sub.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;
• (g) --(p-Ph)--CO--CH.sub.3,
• (h) --(p-Ph)--NH--CO--(p-Ph)--NH--CO--CH.sub.3,
• (i) --(p-Ph)--NH--CO--(Ph),
• (j) --(p-Ph)--NH--CO--CH.sub.3,
• (k) --(p-Ph)--NH--CO--NH.sub.2,
• (l) --(p-Ph)--CH.dbd.N--NH--CO--NH.sub.2,
• (m) .beta.-napthyl,
• (n) --CH.sub.2 --CO--R.sub.16,
• wherein --(p-Ph)-- is para-phenylene and --(Ph) is phenyl;
• wherein R.sub.16 is phenyl, p-bromophenyl, p-biphenyl, p-nitrophenyl, p-benzamidophenyl, or 2-napthyl, or
• (o) a pharmacologically acceptable cation;
• wherein R.sub.7 and R.sub.8 are hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different, and wherein R.sub.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.sub.2 is hydrogen, hydroxyl, or hydroxymethyl,
• wherein R.sub.5 and R.sub.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.sub.5 and R.sub.6 is fluoro only when the other is hydrogen or fluoro, and
• wherein X is
• (1) trans--CH.dbd.CH--,
• (2) cis-CH.dbd.CH--,
• (3) --C.tbd.C--, or
• (4) --CH.sub.2 CH.sub.2 --;
• with the proviso that when L.sub.1 is --(CH.sub.2).sub.n -- and R.sub.1 is other than --CH.sub.2 NR.sub.7 R.sub.8 or --CONHSO.sub.2 R.sub.15, one of R.sub.5 and R.sub.6 is other than hydrogen.