Thiazolidinedione derivatives as anti-hyperglycemic agents

Details Thiazolidinedione derivatives as anti-hyperglycemic agents Thiazolidinedione derivatives as anti-hyperglycemic agents

C - Chemistry, Metallurgy

07

D

C07D 277/36 (2006.01) A61K 31/425 (2006.01) A61K 31/435 (2006.01) A61K 31/505 (2006.01) C07D 277/74 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2184739

This invention relates to novel 5-[3-aryl-prop- 2-ynyl]-5-(arylsulfonyl)- thiazolidine-2,4-diones and 5-[3-aryl-prop-2-ynyl]-5- (arylsulfanyl)thiazolidine- 2,4-diones characterized by general formula (I), wherein Ar is phenyl, 2-naphthyl, alkyl substituted phenyl, alkoxy substituted phenyl, halogen substituted phenyl, 2-pyridinyl, substituted 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-quinolinyl, 2-pyrimidinyl, 2-benzoxazolyl, 2-benzthiazolyl, 2-benzimidazolyl, 2-furanyl, 2-benzo-[b]-furanyl, 2-thienyl, 2-benzo-[b]-thienyl; n is 0 or 2; and Ar' is phenyl, alkyl substituted phenyl, perfluoroalkyl substituted phenyl, halogen substituted phenyl, alkoxy substituted phenyl, perfluoroalkoxy substituted phenyl and alkylthio substituted phenyl. This invention also relates to the use of the abovementioned compounds in lowering the blood glucose levels in hyperglycemic mammals and pharmaceutical compositions containing the same.

L'invention concerne de nouvelles 5-[3-aryl-prop-2-ynyl]-5-(arylsulfonyl)-thiazolidine-2,4-diones et 5-[3-aryl-prop-2-ynyl]-5-(arylsulfanyl)thiazolidine-2,4-diones caractérisées par la formule générale (I), où Ar représente phényle, 2-naphtyle, phényle substitué par alkyle, phényle substitué par alcoxy, phényle substitué par halogène, 2-pyridinyle, 2-pyridinyle substitué, 3-pyridinyle, 4-pyridinyle, 2-quinolinyle, 2-pyrimidinyle, 2-benzoxazolyle, 2-benzthiazolyle, 2-benzimidazolyle, 2-furanyle, 2-benzo-[b]-furanyle, 2-thiényle, 2-benzo-[b]-thiényle; n est égal à 0 ou 2; et Ar' représente phényle, phényle substitué par alkyle, phényle substitué par perfluoroalkyle, phényle substitué par halogène, phényle substitué par alcoxy, phényle substitué par perfluoroalcoxy et phényle substitué par alkylthio. L'invention concerne également l'utilisation des composés mentionnés ci-dessus pour abaisser les taux de glycémie chez les mammifères hyperglycémiques, et les compositions pharmaceutiques contenant ces composés.

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