Benzophenone derivatives and process for their production

Details Benzophenone derivatives and process for their production Benzophenone derivatives and process for their production

C - Chemistry, Metallurgy

07

C

260/545.1, 260/5

C07C 49/76 (2006.01) A61K 31/00 (2006.01) A61K 31/165 (2006.01) A61K 31/195 (2006.01) A61K 31/215 (2006.01) A61K 31/22 (2006.01) A61K 31/275 (2006.01)

Patent

CA 1043348

ABSTRACT OF THE DISCLOSURE The present invention relates to pharmacologically valuable new benzophenonc derivatives having a pronounced sedative action on the central nervous system and some of which also possess muscle-relaxing and aggression-inhibiting properties. These new derivatives have the structural formula Image and the pharmaceutically acceptable acid addition salts thereof in which R1 and R2 are substituents selected from the group consisting of hydrogen, saturated and unsaturated alkyl groups having 1-4 carbon atoms; R3 is selected from the group consisting of -COOC3H7, -COOC4H9, -COOC6H5, -C6H5, -?-NHR4, whereby R4 is an aliphatic radical with 1 to 4 carbon atoms or phenyl and Y is an oxygen or sulfur atom: if m is o R3 13 further selected from the group consisting of -COOCH3 and -COOC2H5; n is an integer selected from 1 and 2 ; and m is an integer selected from 0, 1, 2 and 3, and wherein the rings A and B may be substituted, ring A being substituted preferably with halogen such as chlorine or with nitro, trifluoromethyl, methyl, methoxy or methylmercapto, preferably in the 5 positon. - 1 - and ring B being preferably substituted in the 2' position with chlorine or fluorine. The radicals R1 and R2 preferably signify hydrogen or a methyl group, or a n-butyl group in the case of Ring b. Compounds represented by the above structural formula may be produced by reacting a compound represented by the formula Image with a compound having the formula Y - CmH2m - R3, one of X and Y signifying the substituent R2 - NH - and the other signifying a halogen atom, preferably a bromine of chlorine atom, so as to form the above specified benzophenone derivative with the elimination of H - Hal, R1, R2, R3, n and m being as defined above, and the rings A and B being optionally substituted as discussed above. The hydrogen halide which is eliminated is advantageously bound by the addition of an acid-binding agent, as for example, a molar excess of the amine used in the reaction or, for example, triethylamine, dimethylaniline, potassium or sodium carbonate or sodium bicarbonate. The reaction is carried out in a suitable solvent, preferably at an elevated temperature, typically the reflux temperature of the solvent used. - 2 -

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