METHOD FOR THE PREPARATION OF NOVEL HETEROAROMATIC AMINODERIVATIVES

摘要

The invention relates to new heteroaromatic amine derivatives of formula (I) wherein A represents a -CH2-CH2-, -CH=CH-or group and B represents a methylene, carbonyl or thiocarbonyl group or A represents a -CO-CO or group and B represents a methylene group, in which the carbon atom marked x is linked to the phenyl nucleus, E represents a straight-chained alkylene group optionally substituted by an alkyl group, G represents a straight-chained alkylene group optionally substituted by an alkyl group, R1 represents a hydrogen, fluorine, chlorine or bromine atom, a trifluoromethyl, nitro, amino, alkylamino, dialkylamino, alkyl, alkylmercapto, hydroxy, alkoxy or phenylalkoxy group, R2 represents a hydrogen, chlorine or bromine atom or a hydroxy, alkoxy, phenylalkoxy or alkyl group or R1 and R2 together represent an alkylenedioxy group, R3 represents a hydrogen atom, an alkenyl group, an alkyl or phenylalkyl group, and Het represents a 5- or 6-membered heteroaromtic ring bonded via a carbon or nitrogen atom, which contains an oxygen, sulphur or nitrogen atom, two nitrogen atoms or a nitrogen atom and an oxygen or sulphur atom, and onto which additionally a phenyl ring can be condensed, in which case the bond can also be via the phenyl nucleus, or an imidazo[1,2-a]pyridyl group wherein the carbon structure of the above-mentioned groups can be substituted by a methylenedioxy or ethylenedioxy group or can be mono- or disubstituted by a halogen atom or an alkyl, hydroxy, alkoxy, phenylalkoxy, phenyl, dimethoxyphenyl, nitro, amino, acetylamino, carbamoylamino, N-alkyl-carbamoylamino, hydroxymethyl, mercapto, alkylmercapto, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, alkylsulphonylamino, alkoxycarbonylmethoxy, carboxymethoxy or alkoxymethyl group, and at the same time any imino group present in the above-mentioned heteroaromatic groups can be substituted by an alkyl, phenylalkyl or phenyl group, the N-oxides and the acid addition salts thereof with inorganic or organic acids, which have valuable pharmacological properties, particularly the effect of lowering heart rate and oxygen requirement of the heart. They can be used to treat sinus tachycardia or ischaemic heart disease.