GB935591A - Substituted acridans and processes for preparing same - Google Patents

Abstract

The invention comprises acridan derivatives (tranquilisers and anaesthesia-potentiating and reserpine-antagonistic agents) of the general formula <FORM:0935591/IV(a)/1> (wherein R1 and R2 each represents an alkyl radical of at most 4 carbon atoms which can also be bound to each other direct or by way of an oxygen atom or a methylimino, hydroxyethylimino or acetoxyethylimino group, forming together with the nitrogen atom the pyrrolidyl, piperidino, morpholino, methylpiperazinyl, b -hydroxypiperazinyl or b -acetoxyethylpiperazinyl radical, and R3 represents a hydrogen atom or a methyl group), their acid addition salts, processes for preparing them by (a) reacting a metallic derivative of 9-methylacridan with a reactive ester of an aminoalkanol of the general formula <FORM:0935591/IV(a)/2> optionally followed by salt formation, or (b) reacting a reactive ester of 10-(g -hydroxypropyl)-9-methylacridan or 10-(g -hydroxy-b -methylpropyl)-9-methylacridan with NHR1R2, and the preparation of 10-\sTg -[41-(b 1-acetoxyethyl) - piperazinyl- (11)]-b - methylpropyl\sV-9-methylacridan by acetylation of the parent alcohol. The acridan derivatives may also be prepared by (a) heating a compound of the general formula <FORM:0935591/IV(a)/3> (b) alkylating a compound of the general formula <FORM:0935591/IV(a)/4> (wherein R11 represents a hydrogen atom or an alkyl radical of at most 4 carbon atoms), (c) treating compound of the general formula <FORM:0935591/IV(a)/5> (wherein Z, R111 and R21 represent aliphatic radicals which correspond to the propylene-(1,3) radical or 2-methyl-propylene-(1,3) radical, to the radical R1 and to the radical R2 respectively, except that in at least one of them, instead of at least one methylene group linked to a nitrogen atom, there is a carbonyl group) with lithium aluminium hydride, and (d) heating a compound of the general formula <FORM:0935591/IV(a)/6> (wherein X represents a chlorine or bromine atom) with a basic condensing agent, preferably in the presence of copper powder. 10-Chlorocarbonyl-9-methyacridan is prepared by reacting 9-methylacridan with phosgene. 10-(g -Chloropropyl)-9-methylacridan is prepared by reacting the sodium derivative of 9-methylacridan with 1-bromo-3-chloropropane.