11-Aryl-benzo[b]naphtho[2,3-d]furans and 11-aryl-aryl-benzo[b]anphtho[2,3-d]thiophenes useful in the treatment of insulin resistance and hyperglycemia

• Main Authors: A.J.D. DIETRICH, J.E. WROBEL, LI ZENAN
• Format: Patent
• Language: English
• Published: 15.08.2001
• Edition: 7
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

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, -COR , -CH2CO2R , -CH(R )CO2R , or -SO2R ; R and R are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms or aryl; E is S, SO, SO2, 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 ; R is hydrogen or alkyl of 1-6 carbon atoms; Y and Z are each, independently, hydrogen or OR ; R is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, or -CH2CO2R ; R is hydrogen or alkyl of 1-6 carbon atoms; C is hydrogen, halogen or OR ; R is hydrogen, alkyl of 1-6 carbon atoms, -CH(R )W, -C(CH3)2CO2R , 5-thiazolidine-2,4-dione, -CH(R )CH2CO2R , -COR , PO3(R )2, or -SO2R ; R is hydrogen, alkyl of 1-6 carbon atoms, aralkyl, aryl, CH2(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 , -CONH2, -CONHOH, CN, -CONH(CH2)2CN, 5-tetrazole, -PO3(R )2, -CH2OH, or -CH2Br, -CONR CHR CO2R , R is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R 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.