Biheterocyclic-9,11-trideoxy-PGF compounds

Claim 1

A prostaglandin analog of the formula ##STR57## wherein W 1 is ##STR58## wherein R 2 is alkyl of one to 4 carbon atoms, inclusive or alkylcarbonyl of one to 4 carbon atoms, inclusive; wherein Y 1 is (1) trans--CH═CH--CH 2 --, (2) --(ch 2 ) 3 -, (3) --c|c--ch 2 --, (4) trans---CH 2 --CH═CH--,or (5) cis--CH═CH--CH 2 -- wherein L 1 is ##STR59## or a mixture of ##STR60## wherein R 3 and R 4 are hydrogen, methyl, or fluoro, being the same or different, with the provisio that one of R 3 and R 4 is fluoro only when the other is hydrogen or fluoro; wherein Z 1 is (1) cis--CH═CH--CH 2 --(CH 2 ) g --CH 2 --, (2) cis--CH═CH--CH 2 --(CH 2 ) g --CF 2 , (3) cis--CH 2 --CH═CH--(CH 2 ) g --CH 2 --, (4) --(ch 2 ) 3 --(ch 2 ) g --CH 2 --, (5) --(ch 2 ) 3 --(ch 2 ) g --CF 2 --, (6) --ch 2 --o--ch 2 --(ch 2 ) g --CH 2 --, ##STR61## wherein g is one, 2, or 3; wherein R 7 is (1) --(CH 2 ) m --CH 3 , ##STR62## wherein h is zero to 3, inclusive, wherein m is one to 5, inclusive, T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive and s is zero, one, 2, or 3, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl, with the further proviso that R 7 is ##STR63## wherein T and s are as defined above, only when R 3 and R 4 are hydrogen or methyl, being the same or different; 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 ##STR64## 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, or a pharmacologically acceptable cation; (2) --CH 2 OH; (3) --col 4 , wherein L 4 is (a) amido 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 four carbon atoms, inclusive; carbamoylalkyl of one to four carbon atoms, inclusive; cyanoalkyl of one to four carbon atoms, inclusive, acetylalkyl of one to four carbon atoms, inclusive; benzoylalkyl of one to four 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 of one to 4 carbon atoms, inclusive; pyridylalkyl substituted by one, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive; hydroxy, alkoxy of one to 3 carbon atoms, inclusive; hydroxyalkyl of one to 4 carbon atoms, inclusive; dihydroxyalkyl 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) cycloamido selected from the group consistng of ##STR65## wherein R 21 and R 22 are as defined above; (c) carbonylamido 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) sulphonylamido 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 24 is amido of the formula --NR 21 R 22 , as defined above, or cycloamido, as defined above; or (4) --CH 2 NL 2 L 3 , wherein L 2 and L 3 are hydrogen or alkyl of one to 4 carbon atoms, inclusive, being the same or different; or the pharmacologically acceptable acid addition salts thereof when X 1 is not --COOR 1 and R 1 a pharmacologically acceptable cation.