GB905198A - New n-heterocyclic compounds and processes for preparing them - Google Patents

Abstract

The invention comprises 5-dibenzo [b.?] azepines and their 10,11-dihydro-derivatives, of the general formula <FORM:0905198/IV (b)/1> (wherein X represents -CH = CH- or -CH2-CH2- and R represents a low molecular (i.e. C1-4) alkyl radical), as well as the acid addition salts thereof and the quaternary ammonium compounds formed by addition of reactive esters of aliphatic or araliphatic alcohols, and the preparation of compounds I by reacting a reactive ester of a compound of the general formula <FORM:0905198/IV (b)/2> with a secondary amine R-NH-cyclopentyl. The products, which are useful as antiallergics, anticonvulsants or sedatives, for the treatment of mental disorders or for potentiating other pharmaceuticals (e.g., anaesthetics), may also be made by reacting, in the presence of a condensing agent, a compound of the general formula <FORM:0905198/IV (b)/3> with a reactive ester of a compound of the general formula HO-CH2-CH3-CH2-N(R)-cyclopentyl, and, if desired, converting the product into an acid addition of quaternary ammonium salt, or by heating a compound of the general formula <FORM:0905198/IV (b)/4> until one molecular proportion of carbon dioxide is split off, or by treating a compound of the general formula <FORM:0905198/IV (b)/5> (wherein one of the symbols R1 and R11 represents hydrogen and the other a cyclopentyl radical or a low molecular alkyl radical) with a low molecular alkylating agent or a cyclopentylating agent respectively, or by reacting a compound of the general formula <FORM:0905198/IV (b)/6> (wherein Z and R111 represent trimethylene and R respectively except that in at least one of them at least one methylene group attached to nitrogen is replaced by a carbonyl group) with an alkali metal-earth metal hydride. Alcohols of the second general formula above are prepared by reacting an alkali metal derivative of a compound of the third general formula above with propylene oxide, and are converted into reactive esters by treatment with inorganic acid halides, methanesulphonyl halides or arylsulphonyl halides. Reactive esters are also obtainable by reacting the said alkali metal derivatives with a ,g -dihalopropanes preferably having two different halogen atoms, or with halopropyl esters of arylsulphonic acids.