Carbacyclin analogs

A compound of the formula

• wherein Q is
• (1) --COOR.sub.5, wherein R.sub.5 is
• (a) hydrogen,
• (b) (C.sub.1 -C.sub.12)alkyl,
• (c) (C.sub.3 -C.sub.10)cycloalkyl,
• (d) (C.sub.7 -C.sub.12)aralkyl,
• (e) phenyl optionally substituted with one, 2 or 3 chloro or (C.sub.1 -C.sub.4)alkyl,
• (f) phenyl substituted in the para-position with --NHCOR.sub.6, --COR.sub.7, --OC(O)R.sub.8 or --CH.dbd.N--NHCONH.sub.2, wherein R.sub.6 is methyl, phenyl, acetamidophenyl, benzamidophenyl or --NH.sub.2 ;
• R.sub.7 is methyl, phenyl, --NH.sub.2, or methoxy;
• and R.sub.8 is phenyl or acetamidophenyl;
• (g) phthalidyl,
• (h) 3-(5,5-dimethyl-1,3,2-dioxaphosphorinan-2-yl)-2-oxopropan-1-yl P-oxide,
• (i) 3-(5,5-di(hydroxymethyl)-1,3,2-dioxaphosphorinan-2yl)-2-oxopropan-1-yl P-oxide, or
• (j) a pharmacologically acceptable cation;
• (2) --CH.sub.2 OH;
• (3) --COL.sub.2, wherein L.sub.2 is
• (a) an amino group of the formula --NR.sub.9 R.sub.10 wherein R.sub.9 is hydrogen or (C.sub.1 -C.sub.12)alkyl and R.sub.10 is
• (i) hydrogen
• (ii) (C.sub.1 -C.sub.12)alkyl
• (iii) (C.sub.3 -C.sub.10)cycloalkyl,
• (iv) (C.sub.7 -C.sub.12)aralkyl
• (v) phenyl optionally substituted with one, 2 or 3 chloro, (C.sub.1 -C.sub.3)alkyl, hydroxy, carboxy, (C.sub.2 -C.sub.5)alkoxycarbonyl, or nitro,
• (vi) (C.sub.2 -C.sub.5)carboxyalkyl,
• (vii) (C.sub.2 -C.sub.5)carbamoylalkyl,
• (viii) (C.sub.2 -C.sub.5)cyanoalkyl,
• (ix) (C.sub.3 -C.sub.6)acetylalkyl,
• (x) (C.sub.7 -C.sub.12)benzoalkyl, optionaly substituted by one, 2, or 3 chloro, (C.sub.1 -C.sub.3)alkyl, hydroxy, (C.sub.1 -C.sub.3)alkoxy, carboxy, (C.sub.2 -C.sub.5)-alkoxycarbonyl, or nitro,
• (xi) pyridyl, optionally substituted by one, 2, or 3 chloro, (C.sub.1 -C.sub.3)alkyl, or (C.sub.1 -C.sub.3)alkoxy,
• (xii) (C.sub.6 -C.sub.9)pyridylalkyl optionally substituted by one, 2, or 3 chloro, (C.sub.1 -C.sub.3)alkyl, hydroxy, or (C.sub.1 -C.sub.3)alkyl,
• (xiii) (C.sub.1 -C.sub.4)hydroxyalkyl,
• (xiv) (C.sub.1 -C.sub.4)dihydroxyalkyl,
• (xv) (C.sub.1 -C.sub.4)trihydroxyalkyl;
• (b) cycloamino selected from the group consisting of pyrolidino, piperidino, morpholino, piperazino, hexamethyleneimino, pyrroline, or 3,4-didehydropiperidinyl optionally substituted by one or 2(C.sub.1 -C.sub.12)alkyl;
• (c) carbonylamino of the formula --NR.sub.11 COR.sub.10, wherein R.sub.11 is hydrogen or (C.sub.1 -C.sub.4)alkyl and R.sub.10 is other than hydrogen, but otherwise defined as above;
• (d) sulfonylamino of the formula --NR.sub.11 SO.sub.2 R.sub.10, wherein R.sub.11 and R.sub.10 are defined in (c);
• (4) --CH.sub.2 NL.sub.3 L.sub.4, wherein L.sub.3 and L.sub.4 are hydrogen or (C.sub.1 -C.sub.4)alkyl, being the same or different, or the pharmacologically acceptable acid addition salts thereof when Q is --CH.sub.2 NL.sub.3 L.sub.4 ;
• or
• (5) --CN;
• wherein Z.sub.4 is --CH.sub.2 -- or --(CH.sub.2).sub.f --CF.sub.2 -- wherein f is zero, one, 2, or 3;
• wherein
• (1) R.sub.20, R.sub.21, R.sub.22, R.sub.23, and R.sub.24 are all hydrogen with R.sub.22 being either .alpha.-hydrogen or .beta.-hydrogen;
• or
• (2) R.sub.20 is hydrogen, R.sub.21 and R.sub.22 taken together form a second valence bond between C-9 and C-6a, and R.sub.23 taken together with R.sub.24 form a second valence bond between C-7 and C-8 or are both hydrogen, or
• (3) R.sub.22, R.sub.23, and R.sub.24 are all hydrogen with R.sub.22 being either .alpha.-hydrogen or .beta.-hydrogen, and
• (a) R.sub.20 and R.sub.21 taken together are oxo, or
• (b) R.sub.20 is hydrogen and R.sub.21 is hydroxy, being .alpha.-hydroxy or .beta.-hydroxy;
• wherein L is H,H;
• .alpha.-OH,.beta.-H;
• .alpha.-H,.beta.-OH;
• .alpha.-CH.sub.2 OH,.beta.-H;
• .alpha.-H,.beta.-CH.sub.2 OH;
• wherein Y is trans --CH.dbd.CH--, cis--CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, or --C.tbd.C--;
• wherein M is .alpha.-OH,.beta.-R.sub.14 ;
• or .alpha.-R.sub.14,.beta.-OH, wherein R.sub.14 is hydrogen or methyl;
• wherein L.sub.1 is .alpha.-R.sub.15,.beta.-R.sub.16 ;
• .alpha.-R.sub.16,.beta.-R.sub.15 ;
• or a mixture thereof wherein R.sub.15 and R.sub.16 are hydrogen, methyl, or fluoro being the same or different with the proviso that one of R.sub.15 and R.sub.16 is fluoro only when the other of R.sub.15 and R.sub.16 is hydrogen or fluoro;
• wherein ##STR19## (2) --C.tbd.C--C.sub.q H.sub.2.sbsb.q CH.sub.3 wherein q is an integer of from 2 to 6, or
• (3) --C.sub.p H.sub.2.sbsb.p CH.dbd.CH.sub.2 wherein p is an integer of from 3 to 7;
• and pharmacologically acceptable salts and individual optical isomers thereof.