Patent ID: 6306890
Filing Date: 2001-10-23
Classification: A61P,C07D

Abstract:
A compound of the formula ##STR273##where:R=C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 branched alkyl, C.sub.4 to C.sub.8 cycloalkyl, C.sub.1 to C.sub.6 hydroxyalkyl, branched C.sub.1 to C.sub.6 hydroxyalkyl, hydroxy substituted C.sub.4 to C.sub.8 aryl, primary, secondary or tertiary C.sub.1 to C.sub.6 alkylamino, primary, secondary or tertiary branched C.sub.1 to C.sub.6 alkylamino, primary, secondary or tertiary C.sub.4 to C.sub.8 arylamino, C.sub.1 to C.sub.6 alkylcarboxylic acid, branched C.sub.1 to C.sub.6 alkylcarboxylic acid, C.sub.1 to C.sub.6 alkylester, branched C.sub.1 to C.sub.6 alkylester, C.sub.4 to C.sub.8 aryl, C.sub.4 to C.sub.8 arylcarboxylic acid, C.sub.4 to C.sub.8 arylester, C.sub.4 to C.sub.8 aryl substituted C.sub.1 to C.sub.6 alkyl, C.sub.4 to C.sub.8 heterocyclic alkyl or aryl with O, N or S in the ring, alkyl-substituted or aryl-substituted C.sub.4 to C.sub.8 heterocyclic alkyl or aryl with O, N or S in the ring, or halo-substituted versions of the afore mentioned moieties defining R, where halo is chloro, bromo, fluoro or iodo,R.sub.1 =C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 branched alkyl, C.sub.4 to C.sub.8 cycloalkyl, C.sub.4 to C.sub.8 aryl, C.sub.4 to C.sub.8 aryl-substituted C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkoxy, C.sub.1 to C.sub.6 branched alkoxy, C.sub.4 to C.sub.8 aryloxy, or halo-substituted versions of the afore mentioned moieties defining R.sub.1, or R.sub.1 is halo, where halo is chloro, fluoro, bromo, or iodo,R.sub.2 =hydrogen, C.sub.1 to C.sub.6 alkyl or C.sub.1 to C.sub.6 branched alkyl,n=1, 2, 3, or 4, andwhen R.sub.3 =halobenzyl, then X=NH or N--R.sub.4, where R.sub.4 =C.sub.1 to C.sub.6 alkyl or C.sub.1 to C.sub.6 branched alkyl, andwhen R.sub.3 =halobenzoyl, then X=O,and the compound possesses selectivity for inhibition of cyclooxygenase-2, where selectivity is at least 1015 for the ratio of IC.sub.50 for cyclooxygenase-1 divided by IC.sub.50 for cyclooxygenase-2.