Phosphinylmethylaminocarbonyl imino acid compounds useful for treating hypertension

Claim 1

A compound of the formula ##STR174## and a pharmaceutically acceptable salt thereof wherein: X is an imino acid of the formula ##STR175## R 5 is hydrogen, lower alkyl, halogen, keto, hydroxy, ##STR176## a 1- or 2-naphthyl of the formula ##STR177## a 1- or 2-naphthyloxy of the formula ##STR178## or a 1- or 2-naphthylthio of ##STR179## R 6 is keto, halogen, ##STR180## --O--lower alkyl, a 1- or ##STR181## or a 1- or ##STR182## R 7 is keto or ##STR183## R 8 is halogen or --Y--R 16 ; R 11 is lower alkyl, benzyl, or phenethyl; R 12 is hydrogen, lower alkyl, benzyl or phenethyl; R 13 is hydrogen, lower alkyl or 1 to 4 carbons, lower alkoxy or 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, hydroxy, phenyl, phenoxy, phenylthio, or benzyl; R 14 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 is zero, one, two, three or four; p is one, two or three provided that p is more than one only if R 13 or R 14 is hydrogen, methyl, methoxy, chloro, or fluoro; R 15 is hydrogen or lower alkyl of 1 to 4 carbons; Y is oxygen or sulfur; R 16 is lower alkyl of 1 to 4 carbons, ##STR184## or the R 16 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 1 is hydrogen, lower alkyl, halo substituted lower alkyl, amino substituted lower alkyl, benzyl, or phenethyl; R 2 and R 4 are independently selected from the group consisting of hydrogen, lower alkyl, benzyl, benzhydryl, and ##STR185## wherein R 17 is hydrogen, alkyl, cycloalkyl, or phenyl, and R 18 is hydrogen, alkyl, cycloalkyl, lower alkoxy, phenyl, benzyl, phenethyl, or R 17 and R 18 taken together are --(CH 2 ) 2 --, --(CH 2 ) 3 --, --CH═CH--, or ##STR186## and R 3 is alkyl, halo substituted lower alkyl, amino substituted lower alkyl, cycloalkyl-(CH 2 ) n -, ##STR187## wherein R 13 , m and p are as defined above and n is zero or an integer from 1 to 7.