Förfarande för framställning av basiskt substituerade propyletrar av hydroxisubstituerade heterocykliska föreningar

摘要

Racemic compounds of the general formula (I) (wherein R1 stands for a hydrogen atom or an alkyl radical, R2 stands for an alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl or alkenyl radical, or an aralkyl radical optionally substituted by one or more alkyl or alkoxy radicals, the ring B may optionally bear one or more halogen substituents and the ring A is a 5-, 6-, 7- or 8-membered heterocyclic ring containing one or two oxygen and/or nitrogen atoms and optionally bearing one or more substituents selected from alkyl, oxo and hydroxy radicals and the radical of the formula -CH = CH-CH = CH-) and their acid addition salts, but excluding 1-diethylamino - 3 - (quinolin - 8 - yloxy) - 2 - propanol and its acid addition salts, are prepared by (a) reacting a compound of the formula (II) (wherein Y stands for the group wherein X stands for a halogen atom) with NHR1R2, (b) reacting a compound of the formula (III) with a compound of the formula (IV) (which may be generated in situ), (c)-in the case of compounds wherein R1 stands for a hydrogen atom and R2 stands for an alkyl, hydroxyalkyl, alkoxyalkyl or cycloalkyl radical, or an aralkyl radical optionally substituted by one or more alkyl or alkoxy radicals, apart from a benzyl or substituted benzyl radical-hydrogenolysing a compound of the formula (V) (wherein R5 stands for a hydrogenolysable radical) or an acid addition salt thereof, (d)-in the case of compounds of the formula (VI) (wherein R6 stands for a hydrogen atom or a hydroxy radical)-reducing a compound of the formula (VII) or (e)-in the case of compounds wherein R2 stands for an alkyl, hydroxyalkyl, alkoxyalkyl or cycloalkyl radical, or an aralkyl radical optionally substituted by one or more alkyl or alkoxy radicals, and ring B bears one or more halogen substituents-halogenating a compound of the formula (VIII) (wherein R7 stands for an alkyl, hydroxyalkyl, alkoxyalkyl or cycloalkyl radical, or an aralkyl radical optionally substituted by one or more alkyl or alkoxy radicals), optionally followed in each case by acid addition salt formation. Oxazolidine derivatives of the general formula (IX) (wherein R4 stands for a hydrogen atom or an alkyl radical) and their acid addition salts are prepared by reacting a compound of the formula (X) with R4CHO, optionally followed by acid addition salt formation. The preparation of compounds of formulae (II), (III) and (V) and of 1,2-dihydro-6-methoxy-1,4-dimethyl-2-oxoquinoline is described. Compounds of the formulae (I) and (IX) and their acid addition salts are useful in the treatment or prophylaxis of heart diseases, and may be administered in the form of pharmaceutical preparations containing them together with a diluent or carrier.