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US 5,294,617 AGranted
Angiotensin II receptor blocking 2,3,6 substituted quinazolinones
AssigneeAmerican Cyanamid Company
InventorsAranapakam M. Venkatesan, Jeremy I, Levin
Life of this patent
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Abstract
This disclosure describes novel 2, 3, 6 substituted quinazolinones having the formula ##STR1## wherein R.sup.6, X and R are defined in the specification which have activity as angiotensin II (AII) antagonists.
Claims21
A quinazolinone compound having the formula:
- ##STR21## wherein:
- R is ##STR22## X is straight or branched chain lower alkyl of 3 to 5 carbon atoms;
- R.sup.6 is ##STR23## R.sup.1 is H, straight chain lower alkyl of 1 to 4 atoms, --CF.sub.3, --CN,
- phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene or furan;
- R.sup.2 is straight or branched chain lower alkyl of 1 to 4 carbon atoms, cycloalkyl (rings of 3 to 8 carbon atoms), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms), --CF.sub.3 , nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms);
- R.sup.3 is H, straight or branched lower alky of 1 to 4 carbon atoms, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR24## R.sup.4 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR25## R.sup.9 is hydrogen, straight chain or branched chain lower alkyl of 1 to 4 carbon atoms;
- R.sup.10 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, or furan;
- R.sup.11 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, subsituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.12 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.13 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.19 is straight or branched chain lower alkyl of 1 to 4 carbon atoms;
- R.sup.26 is --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR26## and pharmaceutically acceptable salts thereof.
9 more elements
A quinazolinone compound having the formula:
- ##STR28## wherein:
- X is straight or branched chain alkyl of 3to 5 carbon atoms;
- R.sup.18 is --CN or ##STR29## R.sup.6 is ##STR30## R.sup.1 is H, straight chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, --CN,
- phenyl, substituted phenyl (substitution selection from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene or furan;
- R.sup.2 is straight or branched chain lower alkyl of 1 to 4 carbon atoms, cycloalkyl (rings of 3 to 8 carbon atoms), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms);
- R.sup.3 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, or furan;
- --CHO, --CO.sub.2 R.sup.19 or ##STR31## R.sup.4 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR32## R.sup.9 is hydrogen, straight or branched chain lower alkyl of 1 to 4 carbon atoms;
- R.sup.10 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, or furan;
- R.sup.11 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, subsituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.12 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.13 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.19 is straight or branched chain lower alkyl of 1 to 4 carbon atoms;
- R.sup.26 is --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR33##
10 more elements
A quinazolinone compound having the formula. ##STR35## X is straight or branched chain lower alkyl of 3 to 5 carbon atoms;
- R.sup.6 is ##STR36## R.sup.1 is H, straight chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, --CN,
- phenyl, substituted phenyl (substitution selection from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene or furan;
- R.sup.2 is straight or branched chain lower alkyl of 1 to 4 carbon atoms, cycloalkyl (rings of 3 to 8 carbon atoms), phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms);
- R.sup.3 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, or furan;
- --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR37## R.sup.4 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR38## R.sup.9 is hydrogen, straight or branched chain lower alkyl of 1 to 4 carbon atoms;
- R.sup.10 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, or furan;
- R.sup.11 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl (substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, subsituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.12 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.13 is H, straight or branched chain lower alkyl of 1 to 4 carbon atoms, --CF.sub.3, phenyl, substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), pyridine, thiophene, furan, benzyl, substituted benzyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), --OR.sup.9, O-phenyl, O-substituted phenyl(substitution selected from mono-lower alkyl of 1 to 3 carbon atoms, --CF.sub.3, nitro, O-alkyl of 1 to 3 carbon atoms), O-pyridine, O-thiophene, O-furan, --NH.sub.2, --NHR.sup.19, --NR.sup.19 R.sup.19, --CO.sub.2 R.sup.19, or --CONR.sup.9 R.sup.9 ;
- R.sup.19 is straight or branched chain lower alkyl of 1 to 4 carbon atoms;
- R.sup.26 is --CHO, --OR.sup.19, --CO.sub.2 R.sup.19 or ##STR39##
8 more elements
Dependencies are inferred from the claim text.