| 摘要 |
1,155,580. Imidazole derivatives. J. R. GEIGY A.G. 20 Oct., 1966 [21 Oct., 1965], No. 46982/66. Heading C2C. Novel imidazoles (including tautomeric forms and acid addition salts thereof) of the general formula wherein R 1 signifies C 1-4 alkyl, alkoxyalkyl having at most 5 carbons with at least 2 in the alkyl portion, a pyridyl group, or a monocarbocyclic aryl group mono-, di- or tri-substituted by C 1 or C 2 alkoxy, F, Cl, Br and CF 3 , or di- or tri-substituted by two or three C 1 or C 2 alkyl groups or one or two C 1 or C 2 alkyl groups in conjunction with one or two C 1 or C 2 alkoxy groups, F, Cl, Br and/or CF 3 , R 2 signifies H or C 1-4 alkyl, and R 3 signifies a monocarbocyclic aryl group mono-, di- or tri-substituted by C 1 or C 2 alkoxy, F, Cl, Br and CF 3 , or di- or trisubstituted by two or three C 1 or C 2 alkyl groups or one or two C 1 or C 2 alkyl in conjunction with one or two C 1 or C 2 alkoxy groups, F, Cl, Br or CF 3 , or when R 1 is other than alkyl R 3 can signify H or a monocarbocyclic aryl group mono-substituted by C 1 or C 2 alkyl, or when R 1 is a pyridyl group R 3 can represent C 1-4 alkyl, are obtained: (a) by heating in solution a compound (as such or generated in situ) of the general formula R 1 .NH.C(: S).NH.CHR 2 .C(: X).R 3 or its tautomeric forms, wherein .C(:X) signifies a carbonyl group or a functional group which can be transformed into a carbonyl group by hydrolysis or oxidation; (b) by reacting in formaldehyde an amine, R 1 NH 2 , and anα- isonitroso ketone, R 3 .C(: O).C(: NOH).R 2 , or its tautomeric forms and treating the reaction mixture with a reactant which gives off hydrosulphide ions; or (c) by decarboxylating an imidazole related to that illustrated above such that instead of R 2 there is a carboxy group, or its tautomeric forms, to yield a product wherein R 2 is a hydrogen atom. 1 - Methyl - 4 - carboxy - 5 - (4 - chlorophenyl)- 2-mercaptoimidazole is prepared by treating a mixture of 37% aqueous formaldehyde, methylamine and methyl-α-isonitroso-4-chlorobenzoyl acetate in ethanol with hydrogen sulphide; the mixture is subsequently heated under reflux in the presence of 3N sodium hydroxide and then acidified. 3-Pyridine isothiocyanate is prepared by adding thiophosgene to a cooled mixture of 3-aminopyridine calcium carbonate, chloroform and water. Aminoacetaldehyde diethylacetal isothiocyanate is prepared by adding aminoacetaldehyde diethylacetal in chloroform to a mixture of thiophosgene, calcium carbonate, water and chloroform. Pharmaceutical preparations showing analgesic, anti-inflammatory and antipyretic properties contain as active ingredient the above novel compounds and administration is orally, rectally or parenterally.
|
