Compounds having angiotensin converting enzyme inhibitory activity and

Abstract

Novel compounds possessing both angiotensin enzyme inhibitory activity and diuretic activity are disclosed. The compounds are represented by the general formula ##STR1## in which X is ##STR2## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, and cycloalkyl, and may be the same or different; n is an integer from 0 to 4 inclusive; M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cyloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl, or M and R.sub.6 taken together with the nitrogen to which M is bonded and the carbon to which R.sub.6 is bonded form a saturated unsubstituted heterocyclic group containing 3 or 4 ring carbon atoms; Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy; Z.sub.1 and Z.sub.2 each is a chemical bond, the group X.sub.3 --(CH.sub.2).sub.m, an amino acid group or the group X.sub.3 --(CH.sub.2).sub.m --X.sub.3 wherein X.sub.3 is oxygen, sulfur or NH and m is an integer from 0 to 4 inclusive; A and B each is the same as R.sub.1 or halogen, trifluoromethyl, OR.sub.1, NO.sub.2, NR.sub.1 R.sub.2, SO.sub.2 NH.sub.2, CN, SR.sub.1, SOR.sub.1, SO.sub.2 R.sub.1, CONR.sub.1 R.sub.2, COOR.sub.1 ; C is hydrogen alkyl, heteroallyl, amino, --CR.sub.1 .dbd.CR.sub.2 --, ##STR3## aminoalkyl, furfurylmethylamino, aminoaryl or aminobenzyl; X.sub.1 and X.sub.2 are each S, SO, SO.sub.2, NR.sub.1, O, chemical bond, (CR.sub.9 R.sub.10).sub.m, --CR.sub.9 .dbd.CR.sub.10 --, and CHOH, with the proviso that at least one of X.sub.1 and X.sub.2 be (CR.sub.9 R.sub.10).sub.m, wherein R.sub.9 and R.sub.10 are each hydrogen or lower alkyl, and m is an integer from 1 to 5; Ar is a divalent arylene or heteroarylene; and R.sub.7 and R.sub.8 are each hydrogen, alkyl, halo, cyano, hydroxy, alkoxy, amino, alkylamino, dialkylamino, mercapto, alkylmercapto, nitro, trifluoromethyl, carboxy, carbalkoxy, COY and NHCONHR.sub.1 wherein R.sub.1 and Y are as hereindefined; and pharmaceutically-acceptable salts thereof.