5,9α-Imino- or 6,9α-iminomethylene-9-deoxy-PGF1 compounds

Claim 1

A prostacyclin analog of the formula ##STR1## wherein R 2 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, or alkylcarbonyl of one to 4 carbon atoms, inclusive; Wherein one of p and q is the integer one and the other is the integer zero; Wherein Z 1 is (1) --(CH 2 ) g --CH 2 --CH 2 --, (2) --(ch 2 ) g --CH 2 --CF 2 --, or (3) trans--(CH 2 ) g --CH═CH--, wherein g is the integer zero, one, or 2; Wherein R 8 is hydrogen, hydroxy, or hydroxymethyl; Wherein Y 1 is (1) trans--CH═CH-- (2) cis--CH═CH--, (3) --ch 2 ch 2 --, (4) trans--CH═C(Hal)--, or (5) --C.tbd.C-- wherein Hal is chloro or bromo; Wherein M 1 is ##STR2## wherein R 5 is hydrogen or alkyl with one to 4 carbon atoms, inclusive, Wherein L 1 is ##STR3## A MIXTURE OF ##STR4## and ##STR5## 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; wherein X 1 is (1) --COOR 1 wherein R 1 is hydrogen; alkyl of one to 12 carbon atoms, inclusive; cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive; phenyl; phenyl substituted with one, two, or three chloro or alkyl of one to 3 carbon atoms; phenyl substituted in the para position by ##STR6## wherein R 26 is methyl, phenyl, acetamidophenyl, benzamidophenyl, or --NH 2 ; R 26 is methyl, phenyl, --NH 2 , or methoxy; and R 27 is hydrogen or acetamido, inclusive; or a pharmacologically acceptable cation; (2) --CH 2 OH; or (3) --COL 4 , wherein L 4 is (a) amino of the formula --NR 2 LR 22 , wherein R 21 and R 22 are (i) hydrogen; (ii) alkyl of one to 12 carbon atoms, inclusive; (iii) cycloalkyl of 3 to 10 carbon atoms, inclusive; (iv) aralkyl of 7 to 12 carbon atoms, inclusive; (v) phenyl; (vi) phenyl substitutted with one, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive, hydroxy, inclusive, carboxy, alkoxycarbonyl of one to 4 carbon atoms, inclusive, or nitro; (vii) carboxyalkyl of one to four carbon atoms, inclusive; (viii) carbamoylalkyl of one to four carbon atoms, inclusive; (ix) cyanoalkyl of one to four carbon atoms, inclusive; (x) acetylalkyl of one to four carbon atoms, inclusive; (xi) benzoylalkyl of one to four carbon atoms, inclusive; (xii) benzoylalkyl substituted by one, 2, or 3 chloro, alkyl of one to 3 carbon atoms inclusive; hydroxy, alkoxy of one to 3 carbon atoms, inclusive; carboxy, alkoxycarbonyl of one to 4 carbon atoms, inclusive, or nitro; (xiii) hydroxyalkyl of one to 4 carbon atoms, inclusive; (xiv) dihydroxyalkyl of one to 4 carbon atoms; and (xv) trihydroxyalkyl of one to 4 carbon atoms; with the further proviso that not more than one of R 21 and R 22 is other than hydrogen or alkyl; (b) carbonylamino of the formula --NR 23 COR 21 , wherein R 23 is hydrogen or alkyl of one to 4 carbon atoms and R 21 is as defined above; (c) sulphonylamino of the formula --NR 23 SO 2 R 21 , wherein R 21 and R 22 are as defined above; or (d) hydrazino of the formula --NR 23 R 24 , wherein R 24 is amino of the formula --NR 2 LR 22 , as defined above; wherein R 7 is (1) --(CH 2 ) m --CH 3 , ##STR7## wherein m is the integer one to 5, inclusive, h is the integer zero to 3, inclusive; s is the integer zero, one, 2, or 3, and T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, or with the proviso that not more than two T's are other than alkyl; and the pharmacologically acceptable acid addition salts thereof when R 2 is not alkylcarbonyl and R 1 is not a pharmacologically acceptable cation.