| abstract |
This invention provides compounds of Formula I having the structure n n n wherein: n B and D are each, independently, hydrogen, halogen, alkyl of 1-6 carbon atoms, cycloalkyl of 3-8 carbon atoms, aryl, heteroaryl, aralkyl of 6-12 carbon atoms, or heteroaralkyl of 6-12 carbon atoms except where B and D both are hydrogen; n R 1 is hydrogen, alkyl of 1-6 carbon atoms, —SO 2 Ph(OH)(CO 2 H), —CH(R 2 )W, —CH 2 CH 2 Y, or —CH 2 CH 2 CH 2 Y; n R 2 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, —CH 2 (1H-imidazol-4-yl), —CH 2 (3-1H-indolyl), —CH 2 CH 2 (1,3-dioxo-1,3-dihydro-isoindol-2-yl), —CH 2 CH 2 (1-oxo-1,3-dihydro-isoindol-2-yl), or —CH 2 (3-pyridyl); n W is —CO 2 R 3 , —CONHOH, —CN, —CONHR 3 , aryl, heteroaryl, —CHO, —CH═NOR 3 , or —CH═NHNHR 3 ; n Y is —W, —OCH 2 CO 2 R 3 , aryl, heteroaryl, —C(═NOH)NH 2 , —OR 3 , —O(C═O)NR 4 R 5 , —NR 3 (C═O)OR 3 , —NR 3 (C═O)NR 4 R 5 , or —NR 4 R 5 ; n R 3 is hydrogen or alkyl of 1-6 carbon atoms; n R 4 and R 5 are each, independently, hydrogen, or alkyl of 1-6 carbon atoms or R 4 and R 5 are, together, —(CH 2 ) n —, or —CH 2 CH 2 XCH 2 CH 2 —; n X is O, S, SO, SO 2 , NR 3 , or CH 2 ; n n is 2 to 5; n C is alkyl of 1-18 carbon atoms, aryl, heteroaryl, aralkyl of 6-20 carbon atoms, heteroaralkyl of 6-20 carbon atoms, —CONR 6 R 7 , —NR 3 CONR 6 R 7 , —NR 3 COR 6 , —OR 6 , —O 2 CNR 6 R 7 , —NR 3 CO 2 R 6 , —O 2 CR 6 , —CH 2 OR 6 , —NR 6 R 7 , —CR 3 ═CR 3 R 8 , —CPh 3 , —CH 2 NR 6 R 7 , or n n n R 6 and R 7 are each, independently, hydrogen, alkyl of 1-18 carbon atoms, aryl, heteroaryl, aralkyl of 6-20 carbon atoms, heteroaralkyl of 6-20 carbon atoms, cycloalkyl of 3-10 carbon atoms, —(CH 2 CH 2 O) n CH 3 , —(CH 2 ) m A or R 6 and R 7 are, together, —(CH 2 ) p —, —(CH 2 ) 2 N(CH 3 )(CH 2 ) 4 —, —(CH 2 ) 2 N(R 8 )(CH 2 ) 2 —, or —(CH 2 ) 2 CH(R 8 )—(CH 2 ) 2 —; n R 8 is hydrogen, alkyl of 1-18 carbon atoms, aryl, heteroaryl, aralkyl of 6-20 carbon atoms, heteroaralkyl of 6-20 carbon atoms, cycloalkyl of 3-10 carbon atoms, —(CH 2 CH 2 O) n CH 3 , —(CH 2 CH 2 CH 2 O) n CH 3 , or —(CH 2 ) m A; n A is aryl, heteroaryl, aryloxy, heteroaryloxy, arylthio, heteroarylthio, arylsulfoxy, heteroarylsulfoxy, arylsulfonyl, heteroarylsulfonyl, —CHF 2 , —CH 2 F, —CF 3 , —(CH 2 CH 2 O) n CH 3 , —(CH 2 CH 2 CH 2 O) n CH 3 , —CO 2 R 3 , —O(C═O)NR 6 R 7 , aralkyloxy, or heteroaralkyloxy; n m is 2 to 16 n p is 2 to 12 n or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia. |