3- AND 5-SUBSTITUTED 1,2,3,4-OXATRIAZOLE-5-IMINE COMPOUNDS, METHOD FOR THEIR PREPARATION, PHARMACEUTICAL PREPARATIONS CONTAINING THEM, AND THE USE OF THE COMPOUNDS FOR THE PRODUCTION OF MEDICAMENTS

摘要

The compounds have the general formula wherein R1 is the same or different and represents alkyl or alkoxy groups of 1 to 3 carbon atoms, halogen, trifluoromethyl, nitro, cyano, phenyl or alkylsulfonyl groups, n is a number from 1 to 3, and R1 is not halogen or alkyl when n is 1, X is -SO2 or -C (O) NH-, Y is - (CHR2) m -, wherein m is a number from 1 to 4 and R2 is -CH2-aryl, and Q is 10-camphoryl, -C 0 -C 0 -alkyl, aryl, -SO 2 -alkyl or -SO 2 -aryl, wherein aryl is phenyl or 4-alkyl-1,3-thiazol-5- group is substituted with 1 to 3 Z groups, with Z being -NH -C (O) -C1-6alkyl, -C (O) -C1-6alkyl or -O- (CHR3) p-OH, p is a number from 1 to 4 and R3 is H or OH, Z may represent methoxy, when the aryl group in -SO2-aryl is a phenyl group. Are obtained by ring closure of a 1-arylthiosemicarbazide derivative of the general formula wherein R1 and n are as defined in formula I by treatment with alkylene nitrite of 1 to 6 carbon atoms or alkali metal nitrite in acidic medium at a temperature of 0 to 100. The resulting salt is then converted to the corresponding free compound which subsequently reacts with a compound of the type C1SO2-YQ or O = C = NYQ, wherein Y and Q are as defined in formula I. The compounds of general formula I may form part of a pharmaceutical preparation together o with a pharmaceutically acceptable carrier or diluent. They can be used to prepare a drug for the treatment of asthma, an inhibitor drug