| abstract |
The invention provides compounds of formula (I) having a structure wherein A is hydrogen, halogen, or OH; B and D are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, nitro, amino or OR; R is hydrogen, alkyl of 1-6 carbon atoms, -COR1, -CH2CO2R?1, -CH(R1a)CO¿2R1, or -SO¿2?R?1; R1 and R1a¿ are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms or aryl; E is S, SO, SO¿2?, O; X is hydrogen, halogen, alkyl of 1-6 carbon atoms, CN, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy, arylalkoxy of 6-12 carbon atoms, nitro, amino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, or -OCH2CO2R?1b; R1b¿ is hydrogen or alkyl of 1-6 carbon atoms; Y and Z are each, independently, hydrogen or OR2; R2 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, or -CH¿2?CO2R?3; R3¿ is hydrogen or alkyl of 1-6 carbon atoms; C is hydrogen, halogen or OR4; R4 is hydrogen, alkyl of 1-6 carbon atoms, -CH(R5)W, -C(CH¿3?)2CO2R?6¿, 5-thiazolidine-2,4-dione, -CH(R7)CH2CO2R?6, -COR6, PO¿3(R6)2, or -SO2R6; R5 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl, aryl, CH¿2?(1H-imidazol-4-yl), -CH2(3-1H-indolyl), -CH2CH2(1,3-dioxo-1,3-dihydro-isoindol-2-yl), -CH2CH2(1-oxo-1,3-dihydro-isoindol-2-yl), -CH2(3-pyridyl), or -CH2CO2H; W is -CO2R?6¿, -CONH¿2?, -CONHOH, CN, -CONH(CH2)2CN, 5-tetrazole, -PO3(R?6)¿2, -CH2OH, or -CH2Br, -CONR?6CHR7CO2R8, R6¿ is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R7 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R8 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insuling resistance or hyperglycemia. |