MX9504230A - 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. - Google Patents

Abstract

3- and 5-substitued 1,2,3,4-oxatriazole-5-imine compounds of the general formula I (see formula) wherein R1 is the same 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 - C(O)NH-; -SO2-; C(O)- or a direct bond; y means -S-Z; or S, and A is any pharmaceutically acceptable anion; and Z is the same or different groups and represents h, cyano, trifluoromethyl, nitro, -CH = CH2, -C=CH, straight or branched C1-C6-alkyl, C3-C7-cycloalkyl, phenyl or optionally substituted phenyl; are prepared by ring closing a 1-arylthiosemicarbazide derivative of the general formula II (see formula).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 degree C, whereafter the resulting salt is converted into the corresponding free compound, which is subsequently reacted with a compound of the type CISO2-CH2- Y or O = C =N-CH2-Y, wherein Y has the same meaning as in formula I. The compounds of the general formula I may form part of a pharmaceutical preparation in association with a pharmaceutically acceptable carrier or diluent. The compounds of the general formula I may be used for the preparation of a medicament for the treatment of asthma, a medicament for the treatment of blood clots (thrombosis), a medicament being effective against impotence and a medicament being effective against pre-eclampsia.