Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts compositions and method of use

US4207320A · kind A · utility

Assignee

• WARNER-LAMBERT COMPANY LLC · US

Inventors

• David B. Capps · Ann Arbor, US
• Mario M. Angelo · Ypsilanti, US
• Townley P. Culbertson · Ann Arbor, US

Key dates

• Filing date: Aug 28, 1978
• Grant date: Jun 10, 1980
• Expiry date: Aug 28, 1998

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D471/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts having the formula I: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, C.sub.4 -C.sub.6 cycloalkyl, di(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, 4-morpholinyl or 2,2-dimethylhydrazino; PA1 R.sub.2 is hydrogen, lower alkyl, lower alkylamino, di(lower alkyl)amino, C.sub.4 -C.sub.6 cycloalkylamino, lower alkoxy(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, hexahydro-1H-azepin-1-yl, 4-morpholinyl, benzylamino, N-methylbenzylamino or 2-phenylethylamino; PA1 R.sub.3 is hydrogen or methyl; PA1 X is an anion; with the proviso that at least one of R.sub.1 and R.sub.2 is other than hydrogen, lower alkyl or C.sub.4 -C.sub.6 cycloalkyl; and with the further proviso that when R.sub.2 is dimethylamino, at least one of R.sub.1 and R.sub.3 is other than hydrogen, and intermediates used in the preparation thereof are disclosed. The compounds of the invention are prepared by amination of the corresponding chloro or fluoro-substituted imidazo [1,2-a:3,4-a']diquinolin-15-ium salts; either the halo substituted …