GB1443602A - Aminoquinoline derivatives - Google Patents

Abstract

1443602 1 - [p - (4 - Quinolylamino)benzamide N-oxide and derivatives thereof UPJOHN CO 11 June 1974 [15 June 1973] 25906/74 Heading C2C [Also in Division A5] Novel compounds of the Formula I wherein R 1 is hydrogen, alkyl, alkoxy, halogen or CF 3 , and either R 2 and R 3 are taken independently, in which case R 2 and R 4 are both hydrogen and R 3 is hydrogen or alkyl or R 2 and R 3 together with the nitrogen atom to which they are attached represent pyrrolidino, piperidino, hexamethyleneimino, morpholino, piperazino, piperazino substituted in the 4- position by phenyl, halo, alkyl, alkoxy or trihalomethyl substituted phenyl or benzyl, or mono- or poly-alkyl-substituted pyrrolidino, piperidino, hexamethyleneimino, morpholino, piperazino, 4 - phenylpiperazino or 4 - benzylpiperazino and R 4 is hydrogen or alkyl, wherein alkyl groups have 1 to 4 carbon atoms, and hydrates and pharmaceutically acceptable salts thereof may be prepared by (1) reacting a quinoline N-oxide III with a p-aminobenzamide of the Formula IV or (2) when R 4 is hydrogen and -NR 2 R 3 is a heterocyclic group reacting a cyanomethylester of the appropriately substituted p-(4- quinolyl)amino benzoic acid N-oxide with an amine HNR 2 R 3 . The intermediates of the Formula IV are prepared by catalytic hydrogenatin of the corresponding p-nitrobenzamide. The intermediates of Formula III are prepared by N-oxidation of the appropriate quinoline. p - [7 - Chloro - 4 - quinolyl)amino]benzoic acid N - oxide cyanomethyl ester hydrate may be prepared by N-oxidation of the corresponding quinoline derivative.