Antihypertensive compounds having both diuretic and angiotensin converting enzyme inhibitory activity

Claim 1

A compound represented by the formula ##STR23## and the pharmaceutically acceptable salts thereof, wherein: A is ##STR24## 1is 1 or 2; n is 0 or 1; p and q are 0, 1 or 2, provided that in structures IIb and IIc the sum of p and q is 1 or 2, and that in formula IId, p is not 0; B is --[J]--[L]--[M]--; D is ##STR25## E is --NH--,--O--, --S--, or --CH 2 --; G is --SO 2 -- J is --(CH 2 ) s -- or --((CH 2 ) t --W)--; L is a chemical bond, cis- or trans-lower alkene, lower alkyne, --Z--aryl, --aryl--Z--, --Z--cycloalkyl--, or --cycloalkyl-Z--, wherein aryl is ##STR26## and cycloalkyl is ##STR27## wherein w is 1, 2 or 3; M is --(CH 2 ) u -- or --((CH 2 ) t --X--(CH 2 ) v )--; W is ##STR28## X and Z are independently a chemical bond, -NR 9 -, -O-, -S-, ##STR29## s, u and v are independently 0-5; t is 1-5; R 1 , R 2 are independently hydrogen, lower alkyl or lower acyl; R 3 is hydrogen, lower alkyl, haloloweralkyl, phenylloweralkyl, (cycloalkyl)loweralkyl, aminomethyl, loweralkylaminomethyl, phenyl(lower)alkylaminomethyl, (cycloalkyl)loweralkylaminomethyl, loweralkylthiomethyl or haloloweralkylthiomethyl; R 4 is chlorine or CF 3 ; R 5 is hydrogen, halogen, lower alkyl, lower acyl, lower alkoxy, haloloweralkyl or phenylloweralkyl; R 7 is hydrogen, lower alkyl or aminoloweralkyl; R 6 and R 8 are independently hydroxy, alkoxy having from 1 to 8 carbon atoms, benzyl, allyl, R lO -Qr-(CH 2 ) m -O-, wherein Q is oxygen or sulfur, r is O or 1 and m is 2 to 4, ##STR30## wherein the alkyl has from 3 to 8 carbon atoms, ##STR31## wherein the phenyl may be substituted with group T defined below, 1-glyceryl, ##STR32## R 10 is phenyl, substituted phenyl wherein the substituents are chosen from group T, 1-naphthyl or 2-naphthyl; T is halogen, hydroxy, trifluoromethyl, lower alkoxy, lower alkyl, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, phenyl and substituted phenyl wherein the substituents are chosen from halogen, hydroxy, trifluoromethyl, lower alkoxy or lower alkyl; R 11 is hydrogen or alkyl having from 1 to 8 carbon atoms; R 12 is hydrogen, lower alkyl, unsubstituted or substituted phenyl and substituted or unsubstituted phenyl lower alkyl, wherein phenyl may be substituted by group T; R 13 is hydrogen or lower alkyl; provided that if L is alkene or alkyne, J is --(CH 2 ) s -- wherein s is 1-5; provided that if L is --Z-aryl--or --Z-cycloalkyl--, J is --(CH 2 ) s -- wherein s is 2-5; provided that if L is alkene, alkyne, --aryl-Z-- or --cycloalkyl-Z--, M is --(CH 2 ) u -- wherein u is 1-5; provided that if s and u are each zero, L is aryl or cycloalkyl (i.e. Z is a bond); and provided that if s and v are each zero, L is aryl or cycloalkyl (ie. Z is a bond).