Verfahren zur Herstellung von Derivaten des Cumarins

1,135,907. Coumarin derivatives. CASSELLA FARBWERKE MAINKUR A.G. 1 Nov., 1967 [2 Nov., 1966; 21 Sept., 1967; 26 Sept., 1967], No. 49723/67. Heading C2C. Novel coumarin derivatives of the general Formula I and pharmaceutically acceptable salts thereof, wherein R 1 means hydrogen, lower alkyl or aryl, R 2 represents 6,7- or 7,8- positioned alkoxy, R 3 represents alkoxy, m is the integer 1,2 or 3, A 1 is a straight or branched alkylene radical having 2-3 carbon atoms, A 2 is a straight or branched alkylene radical having 2-4 carbon atoms and Y represents hydrogen, a hydroxy group or an m-alkoxy benzoyl group, m being as defined above, are prepared by reacting a coumarin derivative of the general Formula II wherein R 1 , R 2 , A 1 and A 2 are as defined above and X represents hydrogen or a hydroxy group, if desired, in the presence of an acid-binding agent with an m-alkoxy benzoic acid or functional derivative thereof, m being as defined above. Compounds of Formula I are also prepared by condensing a coumarin derivative of the general formula wherein R 1 , R 2 , A 1 and X are as defined above, if desired in the presence of an acid-binding agent, with an alkoxy benzoic haloalkyl ester of the general formula wherein A 2 , R 3 and m are as defined above and hal represents a halogen atom. Compounds of general Formula II are prepared by reacting the corresponding 3-(#- haloethyl or γ-halopropyl)-4-R 1 -6,7- or 7,8- dialkoxy coumarin with the corresponding N-(#-hydroxy ethyl or γ-hydroxypropyl or 8- hydroxybutyl)-piperazine. The 3-(#-haloethyl or γ-halopropyl)-4-R 1 -6,7- or 7,8-dialkoxy coumarin is prepared by alkylating the corresponding dihydroxy compound. The 3-(#-haloethyl or γ-halopropyl)-4-R 1 -6,7- or 7,5-dihydroxy coumarin is prepared by halogenating the corresponding 3-(#-hydroxyethyl or γ-hydroxypropyl) compound. Pharmaceutical compositions containing as active ingredients compounds of Formula I in admixture with a suitable carrier are administered orally or parenterally and have coronary dilatory activity.