GB925017A - Quaternary ammonium compounds and their preparation - Google Patents

Abstract

The invention comprises quaternary amine compounds of the formula: <FORM:0925017/IV(a)/1> wherein A is a cyclopentyl, cyclohexyl or cycloheptyl ring optionally bearing C1-C4 alkyl groups as substituents and R1 is an ethyl, hydroxyethyl, n-propyl, isopropyl or allyl group when NR2R3 is a dimethylamino or pyrrolidino group, or is a methyl group when R2 and R3 are ethyl or hydroxyethyl, and comprises also the preparation of these compounds by quaternizing the appropriate tertiary amine. The products suitably take the form of salts with halide, methylsulphate, sulphate or p-toluenesulphonate anions, obtainable by usual methods of salt formation and double decomposition. Tertiary amines used as starting materials such as N-cyclohexylmethyl-N-ethyl-N-methylamine, N-cyclohexylmethyl-dimethylamine, N-cyclohexylmethylpyrrolidine, N-cyclopentylmethyl-dimethylamine, N-cycloheptylmethyl-dimethylamine and N-cycloheptylmethyl-N-hydroxyethyl-methylamine are made by treating the appropriate secondary amine with a cycloalkylmethyl bromide. N-2-methylcyclohexylmethyl-dimethylamine is made by chlorinating 2-methylcyclohexylcarboxylic acid with thionyl chloride, reacting the resulting chloride with dimethylamine and reducing the dimethylamide obtained, with lithium aluminium hydride. Pharmaceutical preparations having sympatholytic activity comprise the above quaternary compounds together with an acceptable carrier, suitably in the form of powders, granules, capsules, cachets, tablets, suspensions, solutions or emulsions for oral administration, aqueous solutions or suspensions for injection or as suppositories or pessaries.