Patent GB-874980-A (GB)
Title: Quinoline derivatives
Inventor: BIRTWELL STANLEY
IPC: C07D215/18
Filed: 1958-12-17
Abstract: The invention comprises compounds of the formula <FORM:0874980/IV (b)/1> wherein R represents a hydrogen or halogen atom or a hydroxyl, carboxyl or carboxyamide radical or the group -NR1R11 wherein R1 and R11, which may be the same or different, represent hydrogen atoms or alkyl radicals which may be substituted by hydroxyl or dialkylamino groups or R1 and R11 together with the nitrogen atom to which they are attached may represent a piperidino or morpholino radical and X and Y, which may be the same or different, represent hydrogen, chlorine or bromine atoms and Z represents a chlorine or bromine atom and the ring A may be substituted by a halogen atom or a carboxyl, alkyl or alkoxy radical; and the preparation thereof where R represents the group -NR1R11 by reacting a compound of the formula <FORM:0874980/IV (b)/2> with a compound of the formula HNR1R11, or where R represents a hydrogen or halogen atom or a carboxyl or carboxyamide radical by bromination or chlorination of the corresponding 6-nitroquinaldine derivatives, or where X represents hydrogen and Y represents hydrogen or bromine and Z represents bromine by reducing a compound of the formula <FORM:0874980/IV (b)/3> (wherein W represents a hydrogen or bromine atom), or where R represents a hydrogen or halogen atom or a carboxyamide radical or the group -NR1R11 and where X represents hydrogen and Y represents chlorine or bromine by reacting the corresponding 6-nitroquinoline-2-aldehyde derivative with phosphorus pentachloride or phosphorus pentabromide, or where R represents a hydroxyl radical by hydrolysing a compound of the formula II above; and pharmaceutical compositions containing the products. 6 - Nitro - 2 - trichloromethylquinoline - 8 - carboxylic acid is prepared by oxidising the corresponding 8-methyl compound. 2-Formyl-6-nitro-quinaldine is prepared by oxidising 6-nitro-quinaldine.  6-Nitro-quinaldine-4-carboxamide is prepared by treating 5-nitroisatin with ammonia and acetone. 6-Nitro-quinaldine-4-carboxylic acid is prepared by hydrolysing the corresponding carboxamide.  8-Chloro-6-nitro-quinaldine is prepared by treating 2-chloro-4-nitro-aniline with paraldehyde. 8-Methoxy-6-nitro-quinaldine is prepared by treating 2-methoxy-4-nitro-aniline with crotonaldehyde. 8-Methyl-6-nitro-quinaldine is prepared by treating 2-methyl-4-nitro-aniline with crotonaldehyde.ALSO:Pharmaceutical compositions containing compounds of the formula <FORM:0874980/VI/1> wherein R represents a hydrogen or halogen atom or a hydroxyl, carboxyl or carboxyamide radical or the group -NR1R11, wherein R1 and R11, which may be the same or different, represent hydrogen atoms or alkyl radicals which may be substituted by hydroxyl or dialkylamino groups or -NR1R11 may represent a piperidino or morpholino radical and X and Y, which may be the same or different, represent hydrogen, chlorine or bromine atoms and Z represents a chlorine or bromine atom and the ring A may be substituted by a halogen atom or a carboxyl, alkyl, or alkoxy radical, and a carrier may be in the form of ointments, creams, jellies, lotions and pastes.