Verfahren zur Herstellung von Derivaten des Cumarins

1,184,762. 7-Alkoxycoumarin derivatives. CASSELLA FARBWERKE MAINKUR A.G. 5 Jan., 1968 [7 Jan., 1967; 3 Nov., 1967], No. 786/68. Heading C2C. The invention comprises compounds of the Formula I and pharmaceutioally acceptable salts thereof wherein R 1 represents a hydrogen atom or a C 1-4 alkyl, alkenyl or dialkylaminoalkyl group where the alkyl groups attached to the nitrogen atom may be linked directly or via a hetero atom to form a 5- or 6-membered heterocyclic ring; R 2 represents a hydrogen atom or a C 1-4 alkyl or aryl group; R 3 represents a C 1-4 alkoxy group; m represents 1, 2 or 3; A 1 and A 2 represent straight or branched C 2-4 alkylene residues and Y represents a hydrogen atom, a hydroxy group or a group of the Formula II and their preparation by acylating a coumarin of the Formula III where X represents a hydrogen atom or a hydroxy group with the appropriate alkoxybenzoic acid for a functional derivative thereof, by condensing a coumarin of the Formula IV with a haloalkyl ester of the Formula V where Hal represents a halogen atom, by etherifying a 7-hydroxy-coumarin of the Formula VI with a haloalkylpiperazine of the Formula VII or by reacting a haloalkyl derivative of the Formula VIII with an alkali metal salt of the appropriate alkoxybenzoic acid. Hydroxyalkyl-piperazines of the Formula IX may be prepared by reacting 7-(#-chloroethoxy) coumarins with hydroxyalkylpiperazines. 2,3 - Disubstituted - 7 - (# chloroalkyl) coumarins may be prepared by reacting the corresponding 7-hydroxycoumarins with the appropriate #-chloroethyl p-toluenesulphonates. Hydroxyalkylpiperazines of the Formula X may be prepared from the corresponding 7- hydroxycoumarins with epichlorhydrin and reacting the resulting epoxypropoxycoumarins with the appropriate 1-hydroxyalkylpiperazines. 3 - n - Butyl - 4 - n - propyl - 7 - (γ - piperazino - # - hydroxypropoxy) coumarin may be prepared by reacting 3-n-butyl-4-n-propyl-7- (21,31-epoxypropoxy) coumarin with piperazine. Therapeutic compositions with coronary-dilating properties in forms suitable for oral or parenteral administration comprise the compounds of the Formula I or salts thereof, with a suitable carrier.