Patent ID: 6251936
Filing Date: 2001-06-26
Classification: C07D

Abstract:
A compound of formula I having the structure ##STR30##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, hydroxyalkyl of 1-6 carbon atoms, hydroxyalkyl of 6-12 carbon atoms, cycloalkyl of 3-8 carbon atoms, nitro, amino, --NR.sup.1 R.sup.1a, --NR.sup.1 COR.sup.1a, --NR.sup.1 CO.sub.2 R.sup.1a, cycloalkylamino of 3-8 carbon atoms, morpholino, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, --COR.sup.1b or OR;R is hydrogen, alkyl of 1-6 carbon atoms, --COR.sup.1, --(CH.sub.2).sub.n CO.sub.2 R.sup.1, --CH(R.sup.1a)CO.sub.2 R.sup.1, --SO.sub.2 R.sup.1, --(CH.sub.2).sub.m CH(OH)CO.sub.2 R.sup.1, --(CH.sub.2).sub.m COCO.sub.2 R.sup.1, --(CH.sub.2).sub.m CH.dbd.CHCO.sub.2 R.sup.1, or --(CH.sub.2).sub.m O(CH.sub.2).sub.o CO.sub.2 R.sup.1 ;R.sup.1 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, aryl, or CH.sub.2 CO.sub.2 R.sup.1' ;R.sup.1 ' is hydrogen or alkyl of 1-6 carbon atomsE is S, SO, SO.sub.2, or O;X is hydrogen, halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, CN, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyalkyl of 6-12 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy; arylalkoxy, nitro, amino, NR.sup.2 R.sup.2a, NR.sup.2 COR.sup.2a, cycloalkylamino of 3-8 carbon atoms, morpholino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, --OCH.sub.2 CO.sub.2 R.sup.2b or --COR.sup.2c ;Y is hydrogen, halogen, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, hydroxyalkyl of 6-12 carbon atoms, --OR.sup.3, SR.sup.3, NR.sup.3 R.sup.3a, --COR.sup.3b, morpholine or piperidine;R.sup.1a, R.sup.2, R.sup.2a R.sup.3, R.sup.3a are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, or aryl;R.sup.1b is alkyl of 1-6 carbon atoms or aryl;R.sup.2b is hydrogen, alkyl of 1-6 carbon atoms;R.sup.2c and R.sup.3b are each, independently, alkyl of 1-6 carbon atoms, aryl, or aralkyl of 6-12 carbon atoms;C is hydrogen, halogen or OR.sup.4 ;R.sup.4 is hydrogen, alkyl of 1-6 carbon atoms, --CH(R.sub.5)W, --C(CH.sub.3).sub.2 CO.sub.2 R.sup.6, 5-thiazolidine-2,4-dione, --CH(R.sup.7)(CH.sub.2).sub.m CO.sub.2 R.sup.6, --COR.sup.6, --PO.sub.3 (R.sup.6).sub.2, --SO.sub.2 R.sup.6, --(CH.sub.2).sub.p CH(OH)CO.sub.2 R.sup.6, --(CH.sub.2).sub.p COCO.sub.2 R.sup.6, --(CH.sub.2).sub.p CH.dbd.CHCO.sub.2 R.sup.6, or --(CH2).sub.p O(CH.sub.2).sub.q CO.sub.2 R.sup.6 ;R.sup.5 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, aryl, --CH.sub.2 (1H-imidazol-4-yl), --CH.sub.2 (3-1H-indolyl), --CH.sub.2 CH.sub.2 (1,3-dioxo-1,3-dihydro-isoindol-2-yl), --CH.sub.2 CH.sub.2 (1-oxo-1,3-dihydro-isoindol-2-yl), --CH.sub.2 (3-pyridyl), --CH.sub.2 CO.sub.2 H, or --(CH.sub.2).sub.n G;G is NR.sup.6a R.sup.7a, NR.sup.6a COR.sup.7a, ##STR31##W is CO.sub.2 R.sup.6, CONH.sub.2, CONHOH, CN, CONH(CH.sub.2).sub.2 CN, 5-tetrazole, --PO.sub.3 (R.sup.6).sub.2, --CH.sub.2 OH, --CONR.sup.6b CHR.sup.7b, --CH.sub.2 NR.sup.6b CHR.sup.7b CO.sub.2 R.sup.6 ; --CH.sub.2 OCHR.sup.7b CO.sub.2 R.sup.6 --CH.sub.2 Br, or --CONR.sup.6b CHR.sup.7b CO.sub.2 R.sup.6 ;R.sup.6, R.sup.6a, R.sup.7, R.sup.7a are each, independently, is hydrogen, alkyl of 1-6 carbon atoms, or aryl; R.sup.6b is hydrogen or --COR.sup.6c ;R.sup.6c is alkyl of 1-6 carbon atoms or aryl;R.sup.7b is hydrogen, alkyl of 1-6 carbon atoms, or hydroxyalkyl of 1-6 carbon atoms;Z.sup.1 and Z.sup.2 are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, cycloalkyl of 3-8 carbon atoms, nitro, amino, --NR.sup.1 R.sup.1a, --NR.sup.1 COR.sup.1a, cycloalkylamino of 3-8 carbon atoms, morpholino, or OR.sup.8, or Z.sup.1 and Z.sup.2 may be taken together as a diene unit having the formula --CH.dbd.CR.sup.9 --CR.sup.10.dbd.CR.sup.11 --;R.sup.8 is hydrogen, alkyl of 1-6 carbon atoms, or aryl;R.sup.9, R.sup.10, and R.sup.11 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aryl, halogen, hydroxy, or alkoxy of 1-6 carbon atoms;m is 1 to 4;n is 1 or 2;p is 1 to 4;q is 1 to 4;with the proviso that when E is O, Y is hydrogen, Ar is ##STR32##and A, B, C, and D are hydrogen,then Z.sup.1, Z.sup.2, and X are not all hydrogen,or a pharmaceutically acceptable salt thereof.