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filingDate 1972-07-18-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1975-02-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1383220-A
titleOfInvention Triazole derivatives and the manufacture thereof
abstract 1383220 3 - Aminomethyl - 4 - (o - benzyl- and benzoyl - phenyl) - 4H - 1,2,4 - triazoles UPJOHN CO 18 July 1972 [18 Aug 1971] 33589/72 Heading C2C 3 - Aminomethyl - 4 - (o - benzoylphenyl)- 4H-1,2,4-triazoles and novel 3-aminomethyl-4- (o-benzylphenyl)-4H-1,2,4-triazoles of the respective general formulae wherein R 1 is a hydrogen atom or a C 1-3 alkyl, C 3-8 cycloalkyl, phenyl, benzyl or -COOR<SP>1</SP> group (R<SP>1</SP> is a C 1-3 alkyl group) or a heterocyclic aromatic group of 5 or 6 ring atoms, 1-4 of which are selected from O, N and S, each of R<SP>11</SP> and R<SP>111</SP> is a C 1-3 alkyl group or R<SP>11</SP> R<SP>111</SP>N is a pyrrolidino, piperidino or morpholino group, and each of R 2 , R 3 , R 4 and R 5 is a hydrogen or halogen atom or a C 1-3 alkyl, nitro, cyano, trifluoromethyl, C 1-3 alkoxy, C 1-3 alkylthio, C 1-3 alkylsulphinyl, C 1-3 alkylsulphonyl, amino, C 1-3 alkanoylamino or di-C 1-3 alkylamine group, and pharmacologically acceptable acid addition salts thereof are prepared by heating in an organic solvent a 4-(o-benzoylphenyl)-4H-1,2,4-triazole or 4 - (o - benzylphenyl) - 4H - 1,2,4 - triazole of the respective general formulae with formaldehyde, paraformaldehyde and water or formalin and either hydrochloric acid and an amine of the general formula R<SP>11</SP> R<SP>111</SP>NH or the hydrochloride of the said amine, followed optionally by salification of the product. The 3 - aminomethyl - 4 - (o - benzoylphenyl)- 4H-1,2,4-triazoles may also be obtained by oxidizing the 3 - aminomethyl - 4 - (o - benzylphenyl) - 4H - 1,2,4 - triazoles with Jones' reagent. 4 - (o - Benzoylphenyl) - 4H - 1,2,4 - triazoles of the third general formula above are prepared (a) by treatment of the corresponding triazole-3- carboxaldehyde methanol solvate with silver oxide in aqueous methanol and (b) by treatment of an appropriate 2-chloro-4-phenyl-quinoline with hydrazine hydrate, reaction of the resulting 2 - hydrazino - 4 - phenylquinoline with an appropriate triethyl ortho-carboxylate and oxidation of the resulting 5-phenyl-s-triazolo- [4,3-a]-quinoline at a low temperature with sodium periodate and ruthenium dioxide. 2<SP>1</SP>-Benzoyl-4<SP>1</SP>-chloroacetanilide is prepared by reaction of 2-amino-5-chlorobenzophenone with acetyl chloride. Pharmaceutical compositions having sedative, tranquillizing, hypnotic, muscle-relaxant and anticonvulsant activity comprise, as active ingredient, a 3-aminomethyl-4-(o-benzylphenyl)- 4H-1,2,4-triazole of the second general formula above or a pharmacologically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier.
priorityDate 1971-08-18-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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