Patent GB-872279-A (GB)
Title: Improvements in or relating to iminodibenzyl derivatives
IPC: D01D7/00
Filed: 1959-06-24
Abstract: The invention comprises compounds of the formula <FORM:0872279/IV (b)/1> wherein A represents a straight or branched C2-4 saturated aliphatic hydrocarbon group with at least two carbon atoms separating the two nitrogen atoms to which A is attached, X represents hydrogen atoms or identical halogen atoms, and R1 and R2 are the same or different and represent hydrogen atoms or C1-4 alkyl groups, and one or more of the carbon atoms of the piperazine nucleus may carry a C1-4 alkyl group; and acid addition and quaternary ammonium salts thereof; and the preparation thereof by reacting a compound of the formula <FORM:0872279/IV (b)/2> with Halogeno-CO.NR1R2 or methyl isocyanate or isocyanic acid or an alkali metal salt thereof and, if desired, converting the products into their acid addition or quaternary ammonium salts; and pharmaceutical compositions (see Group VI) containing the compounds.  The compounds may also be prepared by interacting compounds having the formulae <FORM:0872279/IV (b)/3> and <FORM:0872279/IV (b)/4> or reactive derivatives thereof, or by interacting compounds having the formulae <FORM:0872279/IV (b)/5> and <FORM:0872279/IV (b)/6> or (when R1 = R2 = H) by heating a compound of the second general formula above with urea. 5-(w-11-Piperazinylalkyl)-iminodibenzyls, in which the carbon atoms of the piperazinyl ring may carry alkyl groups, are prepared by condensing iminodibenzyl with appropriate 1-(w-chloroalkyl) - 4 - acyl - piperazines and deacylating the products or by condensing reactive esters of appropriate 5-(w-hydroxyalkyl)-iminodibenzyls with piperazine or alkyl substituted piperazines.  3,7-Dichloro - 5 - (w - 11 - piperazinylalkyl) - iminodibenzyls are prepared by condensing 3,7-dichloro-iminodibenzyl with appropriate 1-(w-chloroalkyl)-4-acyl-piperazines and deacylating the products. 5-(w-Hydroxyalkyl)-iminodibenzyls are prepared by condensing iminodibenzyl with appropriate 1-chloro-w-tetrahydropyranyloxyalkanes and hydrolysing the products.  5 - (w - Toluene - p - sulphonyloxyalkyl) - iminodibenzyls are prepared by treating the appropriate hydroxy compounds above with toluene-p-sulphonyl chloride.ALSO:Pharmaceutical compositions comprise compounds of the general formula  <FORM:0872279/VI/1> (wherein A represents a straight or branched C2-4 saturated aliphatic hydrocarbon group with at least two carbon atoms dividing the two nitrogen atoms, X represents hydrogen atoms or identical halogen atoms, and R1 and R2 are the same or different and represent hydrogen atoms or C1-4 alkyl groups, and one or more of the carbon atoms of the piperazine nucleus may carry a C1-4 alkyl group) or acid addition or quaternary ammonium salts thereof with pharmaceutical diluents.  The preparations may be in the form of tablets, pills, dispersible powders, granules, capsules, solutions, emulsions, suspensions, syrups and elixirs.  Specified salts are hydrohalides, phosphates, nitrates, sulphates, acetates, propionates, succinates, benzoates, fumarates, maleates, oxalates, tartrates, methanesulphonates, ethanedisulphonates, chlorotheophyllinates, theophyllineacetates, phenolphthaleinates and methylene-bis-b -hydroxynaphthoates, and quaternary halides, alkylsulphates and toluene-p-sulphonates.