ES265235A1 - Substituted 5-h-dibenz[b,f]azepines and their preparation - Google Patents

Abstract

The invention comprises 5H-dibenz[b,f]azepines of general formula <PICT:0914718/IV (b)/1> wherein X represents -CH2.CH2-, Y1 and Y2 each represent hydrogen, halogen, or an alkyl group of at most three carbon atoms, Z represents a straight or branched alkylene chain of at most six carbon atoms, and Am represents a hexamethylenimine radical which may be substituted with one or more alkyl radicals having at most 3 carbon atoms, their acidaddition and quaternary ammonium salts, and their preparation by (1) reaction of a compound of general formula <PICT:0914718/IV (b)/2> in the presence of a condensing agent with a reactive ester of an aminoalcohol of general formula HO-Z-Am (III) (2) thermal decarboxylation of a compound of general formula <PICT:0914718/IV (b)/3> (3) reaction of a reactive ester of a compound of general formula <PICT:0914718/IV (b)/4> with an amine of general formula Am-H (VI) or (4) by treating a compound of general formula <PICT:0914718/IV (b)/5> wherein Z1 and Am1 represent radicals that correspond to Z and Am respectively except that in at least one of them there is at least one carbonyl group instead of a methylene group bound to a nitrogen atom, with an alkali metal-earth hydride. The products are useful as pharmaceutical agents. Esters of general formula (IV) are obtained by reaction of phosgene with heterocycles of general formula (II), and reaction of the 5-chlorocarbonyliminodibenzyls so obtained with aminoalcohols of general formula (III). g -Hexamethyleniminopropanol is prepared by reduction of g -hexamethyleniminopropionic acid ethyl ester with lithium aluminium hydride. Hexamethylenimines of general formula (VI) are prepared by reduction of the corresponding e -caprolactams with lithium aluminium hydride. g -Hexamethylenimino-n-butyl chloride is obtained from 1,3-butylene glycol by reaction with acetyl chloride to form 3-chloro-n-butyl acetate, reaction of the latter with hexamethylenimine and conversion of the g -hexamethyleniminobutanol formed into the chloride, and g -hexamethylenimino-b -methylpropyl chloride is obtained by adding hydrogen bromide to b -methallyl chloride in the presence p of dibenzoyl peroxide and reacting the g -bromo-b -methylpropyl chloride formed with hexamethylenimine. 5-(a -Tert-aminocarbonylalkyl)iminodibenzyls are obtained by reaction of alkali metal derivatives of iminodibenzyls of general formula (II) with low a -bromoalkane carboxylic acid N,Nhexamethylene amides. 5-Hexamethyleniminoalkanoyliminodibenzyls are obtained by reacting alkali metal derivatives of compounds of general formula (II) with halogen alkane carboxylic acid halides and then reacting the halogen alkanoyl compounds obtained with a hexamethylenimine of general formula (VI). Other intermediates of general formula (VII) are obtained by reaction of esters of compounds of general formula (V) with alkali metal compounds of e -caprolactam or adipimide. Specifications 912,013 and 914,717 are referred to.