11-Deoxy-trans-4,5,13,14-tetradehydro-PGI1 compounds

Claim 1

A prostacyclin analog of the formula ##STR1## wherein Y 2 is -C.tbd.C-; wherein Z 2 is ##STR2## wherein Z 1 is (1) -(CH 2 ) g -CH 2 -CH 2 -, or (2) -(CH 2 ) g -CH 2 -CF 2 -, wherein g is the integer zero, one, or 2; wherein R 8 is hydrogen or hydroxymethyl; wherein M 1 is ##STR3## wherein R 5 is hydrogen or alkyl with one to 4 carbon atoms, inclusive, Wherein L 1 is ##STR4## or a mixture of ##STR5## and ##STR6## 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 ##STR7## WHEREIN R 25 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, phenacyl, i.e., ##STR8## phenacyl substituted in the para position by chloro, bromo, phenyl, or benzamido; or a pharmacologically acceptable cation; (2) -CH 2 OH; (3) -ch 2 nl 2 l 3 , wherein L 2 and L 3 are hydrogen or alkyl of one to 4 carbon atoms inclusive or (4) -COL 4 , wherein L 4 is (a) amino of the formula -NR 21 R 22 ; wherein R 21 and R 22 are 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, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive: hydroxy, carboxy, alkoxycarbonyl of one to 4 carbon atoms, inclusive, or nitro; carboxyalkyl of one to 4 carbon atoms, inclusive, carbamoylalkyl of one to 4 carbon atoms, inclusive; cyanoalkyl of one to 4 carbon atoms, inclusive: acetylalkyl of one to 4 carbon atoms, inclusive; benzoylalkyl of one to 4 carbon atoms, inclusive; 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; pyridyl; pyridyl substituted by one, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive; pyridylalkyl of one to 4 carbon atoms, inclusive; pyridylalkyl substituted by one, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive, hydroxy, or alkoxy of one to 3 carbon atoms, inclusive; hydroxyalkyl of one to 4 carbon atoms, inclusive; dihydroxylakyl of one to 4 carbon atoms, and 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) cycloamino selected from the group consisting of ##STR9## wherein R 21 and R 22 are as defined above; (c) 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; (d) sulfonylamino of the formula -NR 23 SO 2 R 21 , wherein R 21 and R 23 are as defined above; or (e) hydrazino of the formula -NR 23 R 24 , wherein R 23 is as defined above and R 24 is amino of the formula -NR 21 R 22 , as defined above, or cycloamino, as defined above; wherein R 7 is (1) -(CH 2 ) m -CH 3 , ##STR10## 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, with the proviso that not more than two T's are other than alkyl; and the pharmacologically acceptable acid addition salts thereof when Z 1 is -CH 2 NL 2 L 3 .