Patent GB-1427190-A (GB)
Title: 4-1h-pyrimidinone compounds a method for producing them and  medicamentss containing them
IPC: C07C253/00
Filed: 1973-09-05
Abstract: 1427190 5-Cyano-4-pyrimidinone derivatives BYK GULDEN LOMBERG CHEMISCHE FABRIK GmbH 5 Sept 1973 [8 Sept 1972 (4)] 41668/73 Heading C2C Novel compounds I in which R<SP>3</SP> is in which R<SP>4</SP> is hydrogen, a C 1-14  alkyl C 2-7  alkenyl or C 2-7  alkynyl group in which a methylene group may be replaced by oxygen and the alkyl group may be substituted by an NR<SP>5</SP>R<SP>6</SP> group C 3-6  cycloalkyl optionally substituted by an NR<SP>5</SP>R<SP>6</SP> group, a phenyl or phenyl-C 1-6  alkyl group (optionally substituted in the ring by C 1-7  alkyl, C 1-7  alkoxy, C 1-7  alkylthio, C 2-5  alkoxycarbonyl halogen, trifluoromethyl, nitro and/or cyano) R<SP>5</SP> and R<SP>6</SP> are hydrogen, a C 1-7  alkyl, C 2-7  alkenyl or C 2-7  alkynyl group in which a methylene group may be replaced by oxygen, or C 3-6  cycloalkyl or R 5  and R 6  together represent C 2-5  alkylene (in which one or more methylene groups may be replaced by O, S or NR<SP>7</SP>), X is O, S or NR<SP>7</SP>, Y is O, S or NH and R<SP>7</SP> is hydrogen, C 1-7  alkyl, C 2-7  alkenyl or C 2-7  alkynyl and their salts are prepared by (1) treating a compound II in which R<SP>1</SP> and R<SP>2</SP> are C 1-7  alkyl or R<SP>1</SP> and R<SP>2</SP> together represent C 2-5  alkylene in which one or more methylene groups may be replaced by O, S or NR<SP>7</SP> (in which R<SP>7</SP> is hydrogen or C 1-7  alkyl) with an acid (2) heating or reacting with an acid or compound III in which A and B are hydrogen, hydroxy, C 1-7  alkoxy NR<SP>8</SP>R<SP>9</SP> or NR<SP>8</SP>-COR<SP>9</SP> (in which R<SP>8</SP> and R<SP>9</SP> are hydrogen, C 1-7  alkyl in which a methylene group may be replaced by oxygen, C 3-6  cycloalkyl or R<SP>8</SP> and R<SP>9</SP> together represent C 2-5  alkylene in which one or more methylene groups may be replaced by O, S or NR<SP>7</SP> and R<SP>7</SP> is hydrogen or C 1-7  alkyl) (3) heating or treating with an acid a compound IV in which R<SP>1</SP> and R<SP>2</SP> is addition to the above definitions, may be a phenyl group or one of R<SP>1</SP> and R<SP>2</SP> may additionally be hydrogen or (4) cyanacetamide is reacted with a trialkyl orthoformate HC(OR) 3  or a dialkoxymethyl ester of an organic carboxylic acid R*COOCH(OR) 2  (in which R is C 1-7  alkyl, and R* is hydrogen, C 1-7  alkyl, aryl, aralkyl or cycloalkyl) in the presence of an acid anhydride and the resulting product reacted with a hydrazine R 3 -NHNH 2 . In the compounds prepared R<SP>3</SP> is C 1-12  alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl cyclohexyloxycarbonyl, #-methoxyethoxycarbonyl, benzamido, #-iso-propoxyethoxycarbonyl, allyloxycarbonyl, acetyl or pmethoxybenzoyl. 2 - Morpholinomethylidene - 3 - oxo - 4 - aza- 5 - (N<SP>1</SP> - acetylhydrazino) - 4 - pentenenitrile is prepared by heating together 3-morpholino-2- cyano-acrylamide, triethylorthoformate, acetic anhydride and formic acid. Compounds I are used to prepare compounds IV or its tautomers by reaction with an amine R 1 R 2 NH; compound IV (R 1 R 2 N=N-methylpiperazine, R<SP>3</SP>=COOMe) is prepared. Compounds I may be used to treat gout, coronary insufficiency and arrhythmia. They form with a suitable vehicle a pharmaceutical composition which may be administered orally or parenterally.