GB1000192A - - Google Patents

Abstract

1,000,192. Iminodibenzyl derivatives. J. R. GEIGY A.G. Feb. 9, 1962 [Feb. 17, 1961], No. 5009/62. Heading C2C. The invention comprises iminodibenzyl compounds of the formula and non-toxic acid addition salts thereof, wherein R is a methyl or ethyl radical, Z is a straight or branched alkylene radical of 2-4 carbon atoms and Am is a low alkylamino or dialkylamino group, wherein the alkyl radical may be joined directly to the alkylene group Z, or both alkyl radicals of the dialkylamino group may be joined directly or through an oxygen atom or an alkylimino, hydroxyalkylimino or alkancycloxyalkylimino group, and processes for the production of these compounds by (a) treating a reactive iminodibenzyl-5-alkyl ester with an amine Am-H; (b) alkylating a compound of the above general formula wherein Am is a primary amine or a monoalkylamine group; (c) treating a 5- unsubstituted iminodibenzyl with a reactive ester of an aimoalkanol Am-Z-OH, wherein Am represents a tertiary amino group; (d) heating an iminodibenzyl 5-amino-alkoxycarbonyl compound until one mol of carbon dioxide is split out and (e) reacting an intermediate compound wherein Am is an N- arylmethyl-alkylamine or N-acyl-alkylamino radical with catalytically activated hydrogen or a hydrolysing agent, respectively to produce a compound wherein Am is a low alkylene group. 3 - Methyl (or ethyl) sulphonyl - iminodibenzyl - 5 - alkyl - esters used as starting materials in process (a) are made by treating a 5-methyl (or ethyl) sulphonyl-iminodibenzyl with an ankylene oxide to give a 3-hydroxyalkyl compound which is then treated with an inorganic acid halide to give a 5-alkylhalide or with an organic sulphonic halide to give 5 - arylsulphonyl - oxyalkyl or 5 - methanesulphonyloxyalkyl compound. Alternatively the iminodibenzyl may be reacted directly with a dihalo-alkone or an arylsulphonic haloalkyl ester. 5 - Primary aminoalkyl - 3 - alkylsulphonyliminodibenzyls used as starting materials in (b) are made by reduction of corresponding 5- cyano-alkyl compounds. 5 - Aminoalkoxycarbonyl - 3 - alkylsulphonyliminodibenzyls used as starting materials in (d) are made by reacting the corresponding iminodibenzyls successively with phosgene (giving a chlorocarbonyl compound) and an aminoalkanol Am-Z-OH. 5 - N - Arylmethyl - N - alkylaminoalkyl-3- alkylsulphonyl - iminodibenzyls and 5 - N- acyl (e.g. N - carbethoxy) - N - alkylaminoalkyl- 3 - alkylsulphonyl - iminodibenzyls used as starting materials in (e) are made by methods analogous to processes (a) and (c). 3 - Methylsulphonyl - 5 [3 - (4 - carbethoxy-1- piperazinyl) - 2- methyl - 1 - propyl] - iminodibenzyl is made by the action of ethyl chloroformate on 3 - methylsulphonyl - 5 - [3 - (4- methyl - 1 - piperazinyl) - 2 - methyl - 1 - propyl] - iminodibenzyl. 3 - (N - Methyl - N - carbethoxy - amino)- propyl chloride is made by treating 3-dimethylaminopropyl chloride with ethyl chloroformate. Pharmaceutical preparations, having antiallergic, antiemetic and sedative activity and potentiating other medicines, especially anaesthetics, comprise the above compounds of the invention, including the salts with non-toxic organic or inorganic acids, and a diluent or excipient. Specification 1,000,191 is referred to.