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filingDate 1972-03-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1974-02-06-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1346029-A
abstract 1346029 Ketone derivatives CASSELLA FARBWERKE MAINKUR AG 30 March 1972 [2 April 1971] 15036/72 Heading C2C The invention comprises novel ketone derivatives of the formula and their pharmaceutically acceptable acid addition salts, wherein R 1 is CN, CONH 2 , COOH, COONa or COOK; R 2 is a radical of the formula or wherein X is C 1-4 alkylene, Y is -OCO- or -CONH-; R 3 and R 4 each are H or C 1-6 alkyl; and R 5 is H or OH, the nucleus I is optionally substituted by 1 to 3 alkoxy, alkyl or NO 2 radicals or halogen atoms; the nucleus II is optionally substituted by 1 to 3 alkoxy or alkyl radicals or halogen atoms; and the nucleus III is optionally substituted by 1 to 3 methoxy radicals and their preparation. The compounds are prepared by reacting compounds of the formula HR 2 with compounds of the formula or alternatively compounds in which Y is -OCO- may be obtained by esterifying the corresponding hydroxyalkylpiperazine derivatives, compounds in which R 1 is CN by the addition of hydrogen cyanide to compounds of the formula and compounds in which R 1 is COOH, COOK 1 or COONa by acid hydrolysis of the corresponding nitriles of the formula or by the diazotization of the corresponding carboxamides of the formula following by, if desired, conversion to the sodium or potassium salts. 3 - Benzoylacrylonitriles, in which the benzene ring is optionally substituted, are obtained by reacting KCN with the appropriate quaternary ammonium salts resulting from the reaction between trimethylamine and the corresponding 2-benzoylvinyl chlorides, obtained by treating the corresponding benzoyl chlorides with acetylene. 3 - (2,3,4 - Trimethoxybenzoyl)acrylic acid is obtained by diazotizing 3-(2,3,4-trimethoxybenzoyl)acrylamide, resulting from the hydrolysis of the corresponding acrylonitrile. 3<SP>1</SP>,4<SP>1</SP>,5<SP>1 </SP>- Trimethoxy - 2 - (1 - piperazine)- acetanilide is obtained by reacting piperazine with 2 - chloro - 3<SP>1</SP>,4<SP>1</SP>,5<SP>1</SP> - trimethoxyacetanilide resulting from the reaction between 3,4,5- trimethoxyaniline und chloroacetyl chloride. 1 - (2 - Hydroxyethyl) - 4 - [2 - (3 - methoxybenzoyl) - 1 - cyanoethyl]piperazine is prepared by 1 - (2 - hydroxyethyl)piperazine with 3- (3 - methoxybenzoyl)acrylonitrile, obtained by reacting KCN with 2-(3-methoxybenzoyl)vinyl chloride resulting from the reaction of thionyl chloride on 2-(3-methoxybenzoyl)vinyl alcohol sodium salt, which is made by reacting 3- methoxyacetophenone with ethyl formate and sodium methylate. Other methoxy substituted benzoylvinyl chlorides are obtained in a similar manner. Pharmaceutical compositions, suitable for oral, parenteral or rectal administration, contain the above novel compounds or acid addition salts thereof together with pharmaceutically acceptable diluents or carriers. The compounds exert dilatory action on the cerebral vessels.
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