New di-oxadiazole derivatives as antihyperglycemic agents

C - Chemistry – Metallurgy – 07 – D

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Details

C07D 413/12 (2006.01) A61K 31/42 (2006.01) C07D 271/07 (2006.01)

Patent

CA 2190017

This invention relates to novel 2-[4-(5-substituted-1,2,4-oxadiazol-3- ylmethoxy)benzyl]-1,2,5-oxadiazolidine-3,5-diones which have demonstrated antihyperglycemic activity in diabetic (ob/ob and db/db) mice, genetic animal models of non-insulin dependent diabetes mellitus (NDDM or Type II diabetes). These compounds are represented by Formula (I), wherein R1 is C6-C10 aryl, optionally substituted by one to three substituents independently selected from C1-C6 alkyl, C1-C6 alkoxy, fluorine, chlorine, bromine, iodine, C1-C3 trifluoroalkyl or C1-C3 trifluoroalkoxy; and R2 is selected from the group consisting of hydrogen, C1-C6 alkyl, fluorine, chlorine, bromine, iodine, C1- C6 alkoxy, C1-C3 trifluoroalkyl, and C1-C3 trifluoroalkoxy, or a pharmaceutically acceptable salt thereof.

Cette invention concerne de nouvelles 2[4-(1,2,4-oxadiazol-3-ylméthoxy)benzyl]-1,2,5-oxadiazolidine-3,5-diones substituées en position 5 du groupe oxadiazole, ayant des propriétés antihyperglycémiques chez les souris diabétiques ob/ob et db/db, qui sont des modèles génétiques animaux du diabète du type II (ou diabète sucré non insulinodépendant). Ces composés sont représentés par la formule (I). Dans cette formule, R?1¿ est un C¿6?-C¿10?aryle, portant éventuellement un à trois substituants choisis d'une manière indépendante parmi C¿1?-C¿6?alkyle, C¿1?-C¿6?alcoxy, fluoro, chloro, bromo, iodo, C¿1?-C¿3?-trifluoroalkyle et C¿1?-C¿3?-trifluoroalcoxy et R?2¿ est choisi parmi l'hydrogène, C¿1?-C¿6?alkyle, fluoro, chloro, bromo, iodo, C¿1?-C¿6?alcoxy, C¿1?-C¿3?trifluoroalkyle et C¿1?-C¿3?trifluoroalcoxy. L'invention concerne également les sels de ces composés acceptables sur le plan pharmaceutique.

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