Imidazole derivatives

Details Imidazole derivatives Imidazole derivatives

C - Chemistry, Metallurgy

07

D

260/298.3

C07D 495/04 (2006.01)

Patent

CA 1160635

EV RAN 4044/54 ABSTRACT Process for the preparation of novel imidazole deriva- tives having antihyperglycaemic and blood platelet aggregation inhibiting properties and of the formula I wherein X is hydrogen or C1-4-alkyl, Y is sulphur or a sulphinyl or sulphonyl group and Z is thienyl, optionally substituted by methyl or fluorine, or a group of the formula Z Image I Image Z wherein R1, R2 and R3 are hydrogen, methyl fluorine, hydroxy, methoxy, methylthio or two of R1, R2 and R3 on adjacent carbon atoms are together methylenedioxy or ethylenedioxy or one of R1, R2 and R3 is mono- or di-(C1-4-alkyl)-amino and the other two are hydrogen, and physiologically compatible acid addition salts thereof, characterised in that for the manufacture of a compound of formula I wherein X is hydrogen a diketone of the formula II wherein Y has the above significance, is reacted with an aldehyde of the formula III Image II Z-CH=O III wherein Z has the above significance, in the presence of a polar solvent containing ammonium ions, in that for the manu- facture of a compound of formula I wherein X is C1-4-alkyl a compound of formula I wherein X is hydrogen is alkylated, if desired, a compound of formula I wherein Y is sulphur is oxidised to give a compound of formula I wherein Y is sulphinyl, and, if desired, a compound of formula I is converted into a physiologically compatible acid addition salt.

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