GB1028913A - Basically substituted diphenyl-methyl ethers, processes for their manufacture and their use - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:1028913/C2/1> in which R and R1 each represents a hydrogen or halogen atom, a C1-3 alkyl group or a C1-3 alkoxy group, R2 represents a hydrogen atom or a methyl group and R4 and R5 each represents a hydrogen atom or a methoxy group, and their physiologically tolerable acid addition salts. The compounds may be prepared by (a) condensing an amine of the formula <FORM:1028913/C2/2> with a phenyl acetone compound, which may be substituted by one or two methoxy groups in the phenyl nucleus, with simultaneous or subsequent hydrogenation, or (b) condensing an amine of Formula II with a 1-phenyl-2-halopropane compound or a 1-phenyl-2-halo-propene compound, which may be substituted by one or two methoxy groups in the phenyl nucleus, and when a propene compound is used, hydrogenating the product, or (c) condensing a compound of the formula <FORM:1028913/C2/3> in which Hal represents Cl, Br or I with a 1-phenyl-2-amino propane compound which may be substituted by one or two methoxy groups in the phenyl nucleus, or (d) condensing a benzhydrol compound, the phenyl moieties of which may each be substituted by a halogen atom or a C1-3 alkyl or C1-3 alkoxy group, with a compound of the formula <FORM:1028913/C2/4> in which R3 represents a hydrogen atom or a methyl or benzyl group, and, if R3 represents a benzyl group, hydrogenating the product to replace the benzyl group by a hydrogen atom, or (e) condensing a diphenyl-bromomethane compound, the phenyl moieties of which may each be substituted by a halogen atom or a C1-3 alkyl or C1-3 alkoxy group, with a compound of the formula <FORM:1028913/C2/5> and, if R3 represents a benzyl group, hydrogenating the product to replace the benzyl group by a hydrogen atom, or (f) reducing a compound of the formula <FORM:1028913/C2/6> or (g) N-methylating a compound of the invention in which R2 represents a hydrogen atom. 1 - m - Methoxyphenyl - 2 - (N - chloroethyl-N-methylamino)-propan is prepared by reacting m-methoxyphenylacetone with 2-aminoethanol, hydrogenating the Schiff's base so obtained, methylating the resulting compound and treating the basic alcohol obtained with thionyl chloride. 1 - (3,4 - Dimethoxyphenyl)-2-(N - chloroethyl - N - methylamino) - propane and 1 - (3,5 - dimethoxyphenyl) - 2 - (N - chloroethyl - N - methylamino) - propane are similarly prepared. Pharmaceutical compositions for oral or parenteral administration, having a physiological effect on the heart and blood circulation, comprise a compound of the invention together with a pharmaceutically acceptable carrier. The compositions may be in the form of tablets or drag<\>aees.