3- AND 5-SUBSTITUTED 1,2,3,4-OXATRIAZOLE-5-IMINE COMPOUNDS, A PROCESS FOR THE PREPARATION THEREOF, A PHARMACEUTICAL PREPARATION CONTAINING SAID COMPOUNDS AND THE USE OF SAID COMPOUNDS FOR THE PREPARATION OF MEDICAMENTS

摘要

3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds of general formula (I) 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 C1SO2-Y-Q or O=C=N-Y-Q, wherein Y and Q have the same meaning as in formula (I).