3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds,...

Details 3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds,... 3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds,...

C - Chemistry, Metallurgy

07

D

C07D 273/00 (2006.01) A61K 31/41 (2006.01) C07D 413/12 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2140641

3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds of general formula (1) wherein R1 is the same or different groups and represents alkyl or alkoxy groups having 1 to 3 carbon atoms, halogen, trifluoromethyl, nitro, cyano, phenyl or alkylsulphonyl groups, n is 1 to 3, X is -SO2 or -C(O)NH-, Y is -(CHR2)m-, wherein m = 1 to 4, and R2 means -CH2-aryl, alkyl, hydrogen or a direct bond, and Q means 10-camphoryl, -C(O)O-alkyl, aryl, -SO2-alkyl or -SO2-aryl, are prepared by ring closing a 1-arylthiosemicarbazide derivative of general formula (II) wherein R1 and n have the same meaning as in formula (I), by treatment with alkyl nitrite having 1 to 6 carbon atoms or alkali metal nitrite under acidic conditions at 0 to 10°C, whereafter the resulting salts is converted into the corresponding free compound, which is subsequently reacted with a compound of the type CISO2-Y-Q or O=C=N-Y-Q, wherein Y and Q have the same meaning as in formula (I).

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