GB900352A - Dextro- and laevo-rotatory 5-(3-dimethylamino-2-methylpropyl)iminodibenzyl - Google Patents

Abstract

The invention comprises dextrorotatory and laevorotatory 5-(3-dimethylamino - 2 - methylpropyl)-iminodibenzyl, their pharmaceutically acceptable salts, their production (1) by reaction of dimethylamine with an enantiomorph of a compound of formula <FORM:0900352/IV (b)/1> wherein Z represents a reactive ester group and (2) by resolution of the racemic form of the required compound by diastereoisomeric salt formation with an optically active acid (e.g. di-(p-toluyl)-D-tartaric acid), and pharmaceutical compositions containing the foregoing compounds. 5-(d,l-3-hydroxy - 2 - methylpropyl)iminodibenzyl is converted into its phthalic acid half-ester by heating under reflux with phthalic anhydride in toluene. This half-ester is resolved by crystallisation of its strychnine salt, from which the required enantiomorph is liberated with hydrochloric acid. Hydrolysis of the resolved half-ester gives the d or l form of 5-(3-hydroxy - 2 - methylpropyl)iminodibenzyl, which is esterified with toluene-p-sulphonyl chloride in the presence of pyridine to give d- or l-5-(3-toluene-p-sulphonyloxy-2-methylpropyl)-iminodibenzyl, a reactive ester used for process (1) above. Pharmaceutical compositions containing the laevo base or its pharmaceutically acceptable acid-addition salts are sedatives, while those containing the corresponding dextro compounds are neurotonic agents. They may be in forms suitable for oral or parenteral administration, e.g. tablets, pills, dispersible powders, granules, emulsions, solutions, suspensions, syrups, elixir or capsules. Specification 668,659 is referred to.