Phenyl oxo-acetic acids useful in the treatment of insulin...

Details Phenyl oxo-acetic acids useful in the treatment of insulin... Phenyl oxo-acetic acids useful in the treatment of insulin...

C - Chemistry, Metallurgy

07

D

C07D 307/80 (2006.01) A61K 31/34 (2006.01) A61K 31/38 (2006.01) C07D 333/56 (2006.01)

Patent

CA 2331120

This invention provides compounds of structural Formula (I) wherein A is O, S, or N; B is -(CH2)m-, -CH(OH)-, or carbonyl; R1 is hydrogen, halogen, alkyl of 1-6 carbon atoms, alcoxy of 1-6 carbon atoms, or trifluoromethyl; R2 is alkyl of 1-18 carbon atoms, aryl of 6-10 carbon atoms, arylalkyl of 7-15 carbon atoms, Het-alkyl wherein the alkyl moiety is 1-6 carbon atoms; Het is (a) or (b); R2a is alkylene of 1-3 carbon atoms; G is oxygen, sulfur, or nitrogen; R3, R4 are each, independently, hydrogen, halogen, alkyl of 1-3 carbon atoms, aryl of 6-10 carbon atoms or a heterocyclic ring of 5 to 7 ring atom containing 1 to 3 heteroatoms selected from oxygen, nitrogen, sulfur; R5 is hydrogen, alkyl of 1-6 carbon atoms, -CH(R7)R8, -C(CH2)nCO2R9, -C(CH3)2CO2R9, - CH(R7)(CH2)nCO2R9, or CH(R7)C6H4CO2R9; R6 is hydrogen, halogen, alkyl of 1-6 carbon atoms, or -OR5; m=1-6; n=1-6; R7 is hydrogen, alkyl of 1-6 carbons atoms, aryl of 6-10 carbon atoms, or arylalkyl of 7-15 carbon atoms; R8 is - CO2R10, -CONHR10, tetrazole, or -PO3; R9 and R10 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aryl of 6-10 carbon atoms, or arylalkyl of 7-15 carbon atoms; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

L'invention concerne des composés de la formule structurelle (I) dans laquelle A représente O, S, ou N, B représente -(CH¿2?)¿m?-, -CH(OH)- ou carbonyle, R?1¿ représente hydrogène, halogène, alkyle C¿1-6?, alcoxy C¿1-6?, ou trifluorométhyle, R?2¿ représente alkyle C¿1-18?, aryle C¿6-10?, arylalkyle C¿7-15?, Het-alkyle où la fraction alkyle possède 1 à 6 atomes de carbone, Het représente un groupe (a) ou (b); R?2a¿ représente alkylène C¿1-3?, G représente oxygène, soufre ou azote, R?3¿ et R?4¿ représentent chacun indépendamment hydrogène, halogène, alkyle C¿1-3?, aryle C¿6-10?, ou un noyau hétérocyclique possédant 5 à 7 chaînons contenant 1 à 3 hétéroatomes choisis parmi oxygène azote, soufre; R?5¿ représente hydrogène, alkyle C¿1-6?, -CH(R?7¿)R?8¿, -C(CH¿2?)¿n?CO¿2?R?9¿, -C(CH¿3?)¿2?CO¿2?R?9¿, -CH(R?7¿)(CH¿2?)¿n?CO¿2?R?9¿, ou CH(R?7¿)C¿6?H¿4?CO¿2?R?9¿; R?6¿ représente hydrogène, halogène, alkyle C¿1-6?, ou OR?5¿; m vaut 1 à 6, n vaut 1 à 6 ; R?7¿ représente hydrogène, alkyle C¿1-6?, aryle C¿6-10?, ou arylalkyle C¿7-15?; R?8¿ représente CO¿2?R?10¿, -CONHR?10¿, tétrazole ou PO¿3?; R?9¿ et R?10¿ représentent chacun indépendamment hydrogène, alkyle C¿1-6?, aryle C¿6-10?, ou arylalkyle C¿7-15?. L'invention concerne également un sel de ces composés, acceptable sur le plan pharmacologique. Ces composés et ce sel sont utiles dans le traitement des troubles métaboliques associés à l'insulinorésistance ou à l'hyperglycémie.

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