1,1,2-TRIPHENYLPROPANE- AND PROPENE DERIVATIVES, A PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE NEW COMPOUNDS

摘要

The invention rotates to new 1,1,2-tri-phenylprepane and -propene derivatives of the general formual (I), (I) wherein A and B each stand for hydrogen or they fore to gether a valence bond, X and Y are identical or different and stand for phenyl group or a phenyl group having a halogen, hydroxy, methoxymethoxy, C1-6 alkoxy or benzyloxy substituent in the para position, R1 is a C1-6 alkyl, epoxyalkyl, azidoalkyl, methoxy methyl or benzyl group or a group of the general formual (II), (II) wherein R2 and R3 each represent hydrogen or a C1-6 alkyl, hydroxyalkyl or haloalkyl group, or R2 and R3 form together with the adjacent nitrogen atom an up in 8-mem-bered heterocyclic group, an up to 6-membered heterocyclic group optionally containing further hetero atom(s), which heterocyclic groups optionally have a lower alkyl or hydroxyalkyl substitutent, a guanidino group, an ?inoguanidino group or a nitroguanidino group, with the proviso that if A and B form together a valence bond and X and Y each stand for phenyl or X is phenyl and Y is p-methoxyphenyl, R1 may not stand for a dimethylaminoethyl, diethylaminoethyl, pyrrolidinoethyl, piperidinoethyl or morpholinoethyl group in the (Z) isomers, stereosiomers and isomeric mixtures thereof, furthermore to acid additon salts of the basic compounds of the general formual (I). The compounds of the general formula (I) can be prepared so that a) a compound of the general formula (III), (III) is reacted with an amino of the general formula H2R3NH or with an allkali metal azide, or b) a compound of the general formual (IV) (IV) is reacted with an alcohol derivative of the general formula R1OM, and, if desired, the methoxymethyl or benzyl protecting group is split off, or c) a compound of the general formula (V), (V) is reacted with an R1-halido or an R1-sulfonate in the presence of an acid binding agent, or d) a propane derivative of the general formula (I) in dehydrogenated. In the above formulae A, B, X, Y and R1 are as defined above, Z is halogen or sulfonyloxy and M represents an alkali metal atom. The new compounds of the general formual (I) act on the endoorine system. They exert oestrogenic or antioestrogenic effects of varying strength, furthermore inhibit the growth of the mammary tumor induced by 7, 12-dimethyl-benz(a)anthracene.