ES251413A1 - New iminodibenzyl derivatives and methods for their preparation - Google Patents

Abstract

The invention comprises N-substituted iminodibenzyls (5-substituted 10,11-dihydro-5-dibenzo[b.f]azepines) of the general formula <FORM:0918462/IV (b)/1> (wherein the two symbols X represent hydrogen atoms, identical halogen atoms, or methyl radicals, Alkylene represents a C2-6 alkylene radical, and R represents a hydroxy- or alkanoyloxy-substituted C1-4 alkyl radical, and the preparation thereof by: (a) reacting a reactive ester of a compound of the general formula <FORM:0918462/IV (b)/2> with an N-substituted piperazine of the general formula <FORM:0918462/IV (b)/3> (b) reacting a compound of the general formula <FORM:0918462/IV (b)/4> with an alkylene oxide or with a reactive ester of a compound of the general formula R-OH (V) (c) (when R is alkanoyloxyalkyl) reacting, in the presence of an acid-binding agent, a compound of the general formula <FORM:0918462/IV (b)/5> with a reactive ester of a compound of the general formula <FORM:0918462/IV (b)/6> (wherein R1 represents an alkanoyloxy-substituted C1-4 alkyl radical) (d) (when R is alkanoyloxyalkyl) reacting a 5-chlorocarbonyliminodibenzyl of the general formula <FORM:0918462/IV (b)/7> with a compound of the general formula VII above to form an ester of the general formula <FORM:0918462/IV (b)/8> and heating this until carbon dioxide is split off or (e) hydrolysing a compound I in which R is alkanoyloxyalkyl or esterifying a compound I in which R is hydroxyalkyl. The products, which form mono- and di-addition salts with inorganic and organic acids, have sedative, antidepressive, antiallergic and antiemetic activity. Reactive esters of compounds II are prepared by reacting compounds VI with reactive diesters of alkanediols, preferably those having two different acid components (e.g. a -bromo-b -or o -chloroalkanes, or arylsulphonic esters of chloro- or bromo-alkanols). N - Piperazinoalkyliminodibenzyls of the general formula IV are prepared by reacting the reactive esters of compounds II with N-acylpiperazines and then hydrolytically splitting off the acyl radical. Acid chlorides of the general formula VIII are prepared by reacting compounds VI with phosgene.