Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors

Claim 1

A compound of the formula ##STR309## and pharmaceutically acceptable salts thereof, wherein R 1 is lower alkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, aminoalkyl, furyl, furylalkyl, thienyl, thienylalkyl, pyridyl, pyridylalkyl or ##STR310## and R 5 and R 6 are independently selected from hydrogen, lower alkyl, haloalkyl, aryl, alkylaryl, cycloalkyl, cycloalkylalkyl furyl, furylalkyl, thienyl, thienylalkyl, pyridyl or pyridylalkyl; R 2 and R 4 each is independently hydrogen, lower alkyl, arylalkyl, benzhydryl or ##STR311## wherein R 7 is hydrogen, lower alkyl or phenyl, R 8 is hydrogen, lower alkyl, lower alkoxy or phenyl or R 7 and R 8 taken together are --(CH 2 ) 2 --, --(CH 2 ) 3 --, --CH═CH--, or ##STR312## n is 0 or 1; R 3 is NH 2 (CH 2 ) m --, ##STR313## R 9 is hydrogen, lower alkyl, aryl or arylalkyl, and m is 0 or an integer of from 1 to 5, and --XOR 4 is an imino or amino acid derivative of the formula ##STR314## R 10 is hydrogen, lower alkyl, halogen, keto, hydroxy, ##STR315## a 1- or 2-naphthyl of the formula ##STR316## a 1- or 2-naphthyloxy of the formula ##STR317## or a 1- or 2-naphthylthio of the formula ##STR318## R 11 is keto, halogen, ##STR319## --O--lower alkyl, a 1- or 2-naphthyloxy of the formula ##STR320## or a 1- or 2-naphthylthio of the formula ##STR321## R 12 is keto or ##STR322## R 13 is halogen or --Y--R 23 ; R 20 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, hydroxy, phenyl, phenoxy, phenylthio, or phenylmethyl; R 21 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, or hydroxy; m 1 is 0 or an integer from 1 to 5; p is 1, 2 or 3 provided that p is more than 1 only if R 20 or R 21 is hydrogen, methyl, methoxy, chloro, or fluoro; R 22 is hydrogen or lower alkyl of 1 to 4 carbons; Y is oxygen or sulfur; R 23 is lower alkyl of 1 to 4 carbons, ##STR323## or the R 23 groups join to complete an unsubstituted 5- or 6-membered ring or said ring in which one or more of the carbons has a lower alkyl of 1 to 4 carbons or a di(lower alkyl of 1 to 4 carbons) substituent; R 18 is lower alkyl, benzyl, or phenethyl; and R 19 is hydrogen, lower alkyl, benzyl or phenethyl.