Cassella Farbwerke Mainkur Aktiengesellschaft

Cassella Farbwerke Mainkur Akt

Klaus Resag

Heinz Gunter Greve

Rolf-Eberhard Nitz

Eckhard Schraven

Rudi Beyerle

Adolf Stachel, Deceased

Ingeburg Lydia Stachel, Heiress

The present invention relates to pharmacologically valuable new benzophenone 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 ##STR1## and the pharmaceutically-acceptable acid-addition salts thereof in which R.sub.1 and R.sub.2 are substituents selected from the group consisting of hydrogen, saturated and unsaturated alkyl groups having 1-4 carbon atoms; R.sub.3 is selected from the group consisting of --COOC.sub.3 H.sub.7, --COOC.sub.4 H.sub.9, --COOC.sub.6 H.sub.5, --C.sub.6 H.sub.5, ##STR2## whereby R.sub.4 is an aliphatic radical with 1 to 4 carbon atoms or phenyl and Y is an oxygen or sulfur atom; if m is O R.sub.3 is further selected from the group consisting of --COOCH.sub.3 and --COOC.sub.2 H.sub.5 ; 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-position, and ring B being preferably substituted in the 2'-position with chlorine or fluorine. The radicals R.sub.1 and R.sub.2 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 ##STR3## with a compound having the formula Y -- C.sub.m H.sub.2m -- R.sub.3, one of X and Y signifying the substituent R.sub.2 -- NH -- and the other signifying a halogen atom, preferably a bromine or chlorine atom, so as to form the above specified benzophenone derivative with the elimination of H -- Hal; R.sub.1, R.sub.2, R.sub.3, 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.

Benzophenone derivatives

The present invention relates to new coumarin compounds useful as coronary dilators and having the formula ##SPC1## Or the hydrochloric acid addition salts thereof, and to methods of preparing same either by acylating, in the presence of acid-binding agents, if desired, coumarin derivatives having the formula ##SPC2## With acylating agents selected from the group consisting of alkoxybenzoic acid having the formula ##SPC3## And functional derivatives thereof, or by condensing, in the presence of acid-binding agents, if desired, coumarin derivatives having the formula ##SPC4## With an amine having the formula RH, wherein R is piperazino which is free of acyloxy groups and is bound via a nitrogen atom; R.sub.1 is selected from the group consisting of alkyl radicals having 1-4 carbon atoms and phenyl; R.sub.2 is selected from the group consisting of 5,7-, 6,7- and 7,8-positioned alkoxy groups having 1-4 carbon atoms; R.sub.3 is selected from alkoxy groups having 1-4 carbon atoms; R.sub.4 is selected from the group consisting of chlorine and bromine; R' is piperazino which is free of hydroxy groups and is bound via a nitrogen group; and m is selected from the group consisting of 1, 2, and 3.

Piperazino substituted coumarin derivatives

The present invention relates to pharmacologically valuable new benzophenone 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 ##SPC1## And their addition salts, in which

Cyanoalkylamino-amido benzophenones

The present invention relates to pharmacologically valuable new benzophenone 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 ##SPC1## And their acid addition salts, in which

Benzophenone derivatives and process for their preparation III

The present invention relates to pharmacologically valuable new benzophenone 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 ##EQU1## and their acid addition salts, in which R.sub.1 and R.sub.2 are substituents selected from the group consisting of hydrogen, saturated and unsaturated alkyl groups having 1-4 carbon atoms; R.sub.3 is a substituent selected from the group consisting of --CN, --CONH.sub.2, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --COOH, and --COOMe, where Me is a metallic cation; n is an integer selected from 1 and 2; and m is an integer selected from 1,2, and 3, and wherein the rings A and B may be substituted, ring A being substituted preferably with a halogen such as chlorine or with nitro, trifluoromethyl, methyl, methoxy or methylmercapto, preferably in the 5 position, and ring B being preferably substituted in the 2' position with chlorine or fluorine. The radicals R.sub.1 and R.sub.2 preferably signify hydrogen or a methyl group, or a n-butyl group in the case of Ring B.

Growing community of inventors

Frankfurt-am-Main, Germany

Klaus Resag