Patent ID: 6174901
Filing Date: 2001-01-16
Classification: C07D

Abstract:
A compound of formula ##STR106##or a pharmaceutically acceptable salt thereof, whereinW is R.sub.1, R.sub.2, or N--R.sub.3 ;A is R.sub.11 and Q is R.sub.12, or A is R.sub.12 and Q is R.sub.11 ;X is N and J is C--R.sub.1 or C--R.sub.2, or X is C--H and J is N--R.sub.3 or N; andwhen W is R.sub.1, then a is a double bond, b is a single bond and J is other than N--R.sub.3 or C--R.sub.1 ; when W is R.sub.2, then a is a double bond, b is a single bond and J is other than N--R.sub.3 or C--R.sub.2 ; and when W is O or N--R.sub.3, then a is a single bond, b is a double bond and J is N--R.sub.3 ;R.sub.1 is --Z--Y or --Y; and each R.sub.3 is independently a hydrogen radical or --Z--Y; provided that the total number of aryl, heteroaryl, cycloalkyl and heterocyclyl radicals in R.sub.1, R.sub.2 and R.sub.3 is 0-3;R.sub.2 is (1) a hydrogen, halo, trifluoromethyl, cyano, --C(O)--OR.sub.21 or --C(O)--NR.sub.5 R.sub.23 radical;(2) alkyl radical optionally substituted by (a) 1-2 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy or alkylthio, and (b) a radical of heterocyclyl, aryl or heteroaryl optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, halo, alkyl, carboxy, carboxamide, trifluoromethoxy or trifluoromethyl radicals; or(3) aryl or heteroaryl radical optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, halo, alkyl, carboxy, carboxamide, trifluoromethoxy or trifluoromethyl radicals;Z is independently a(1) alkyl, alkenyl or alkynyl radical optionally substituted by (a) 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio or halo, and (b) 1-2 radicals of heterocyclyl, aryl or heteroaryl; or(2) heterocyclyl, aryl or heteroaryl radical;wherein the heterocyclyl radicals are optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, alkyl, arylalkyl, heteroarylalkyl or haloalkyl; and the aryl and heteroaryl radicals are optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, halo, alkyl or haloalkyl;each Y is independently a(1) hydrogen radical;(2) halo or nitro radical;(3) --C(O)--R.sub.20, --C(O)--OR.sub.21, --C(O)--NR.sub.5 R.sub.21 or --C(NR.sub.5)--NR.sub.5 R.sub.21 radical;(4) --OR.sub.21, --O--C(O)--R.sub.21, --O--C(O)--NR.sub.5 R.sub.21 or --O--C(O)--NR.sub.22 --S(O).sub.2 --R.sub.20 radical;(5) --SR.sub.21, --S(O)--R.sub.20, --S(O).sub.2 --R.sub.20, --S(O).sub.2 --NR.sub.5 R.sub.21, --S(O).sub.2 --NR.sub.22 --C(O)--R.sub.21, --S(O).sub.2 --NR.sub.22 --C(O)--OR.sub.20 or --S(O).sub.2 --NR.sub.22 --C(O)--NR.sub.5 R.sub.21 radical; or(6) --NR.sub.5 R.sub.21, --NR.sub.22 --C(O)--R.sub.21, --NR.sub.22 --C(O)--OR.sub.20, --NR.sub.22 --C(O)--NR.sub.5 R.sub.21, --NR.sub.22 --C(NR.sub.5)--NR.sub.5 R.sub.21, --NR.sub.22 --S(O).sub.2 --R.sub.20 or --NR.sub.22 --S(O).sub.2 --NR.sub.5 R.sub.21 radical;each R.sub.5 is independently(1) hydrogen radicals;(2) alkyl, alkenyl or alkynyl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, hydroxy, alkoxy, alkylthio, --SO.sub.3 H or halo; or(3) aryl, heteroaryl, aralkyl, heteroaralkyl, heterocyclyl, heterocyclylalkyl, cycloalkyl or cycloalkylalkyl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, hydroxy, alkoxy, alkylthio, alkyl or haloalkyl;each R.sub.20 is independently(1) alkyl, alkenyl or alkynyl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, N-(alkoxycarbonyl)-N-(alkyl)amino, aminocarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halo or aralkoxy, aralkylthio, aralkylsulfonyl, cycloalkyl, heterocyclyl, aryl or heteroaryl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, alkanoyl, hydroxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halo, alkyl or haloalkyl;(2) heterocyclyl radical optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, alkyl or haloalkyl; or(3) aryl or heteroaryl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, alkoxycarbonyl, hydroxy, alkoxy, alkylthio, cyano, halo, azido, alkyl or haloalkyl;each R.sub.21 is independently hydrogen radical or R.sub.20 ;each R.sub.22 is independently(1) hydrogen radical;(2) alkyl radical optionally substituted by a radical of heterocyclyl, aryl or heteroaryl optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, cyano, halo, alkyl or haloalkyl; or(3) heterocyclyl, aryl or heteroaryl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, cyano, halo, alkyl or haloalkyl;R.sub.12 is an ""N""-heteroaryl radical, and R.sub.11 is an aryl radical or heteroaryl radical other than an ""N""-heteroaryl radical, wherein the ""N""-heteroaryl radical, aryl radical and heteroaryl radical other than an ""N""-heteroaryl radical are each optionally substituted by 1-3 radicals of(1) R.sub.30 ;(2) halo or cyano radicals;(3) --C(O)--R.sub.30, --C(O)--OR.sub.29, --C(O)--NR.sub.31 R.sub.32 or --C(NR.sub.31)--NR.sub.31 R.sub.32 radicals;(4) --OR.sub.29, --O--C(O)--R.sub.29, --O--C(O)--NR.sub.31 R.sub.32 or --O--C(O)--NR.sub.33 --S(O).sub.2 --R.sub.30 radicals;(5) --SR.sub.29, --S(O)--R.sub.30, --S(O).sub.2 --R.sub.30, --S(O).sub.2 --NR.sub.31 R.sub.32, --S(O).sub.2 --NR.sub.33 --C(O)--R.sub.30, --S(O).sub.2 --NR.sub.33 --C(O)--OR.sub.30 or --S(O).sub.2 --NR.sub.33 --C(O)--NR.sub.31 R.sub.32 radicals; or(6) --NR.sub.31 R.sub.32, --NR.sub.33 --C(O)--R.sub.29, --NR.sub.33 --C(O)--OR.sub.30, --NR.sub.33 --C(O)--NR.sub.31 R.sub.32, --NR.sub.33 --C(NR.sub.31)--NR.sub.31 R.sub.32, --NR.sub.33 --S(O).sub.2 --R.sub.30 or --NR.sub.33 --S(O).sub.2 --NR.sub.31 R.sub.32 radicals;provided that the total number of aryl, heteroaryl, cycloalkyl and heterocyclyl radicals substituted on each of R.sub.11 and R.sub.12 is 0-1;each R.sub.30 is independently(1) alkyl, alkenyl or alkynyl radicals optionally substituted by 1-3 radicals of --NR.sub.31 R.sub.31, --CO.sub.2 R.sub.23, hydroxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, cyano, halo or aralkoxy, aralkylthio, aralkylsulfonyl, heterocyclyl, aryl or heteroaryl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, cyano, halo, alkyl or haloalkyl;(2) heterocyclyl radical optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, alkyl or haloalkyl; or(3) aryl or heteroaryl radicals optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, halo, alkyl or haloalkyl;R.sub.29 is independently hydrogen radical or R.sub.30 ;each R.sub.31 is independently(1) hydrogen radicals;(2) alkyl radical optionally substituted by an cycloalkyl, aryl, heterocyclyl or heteroaryl radical optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, alkyl or haloalkyl; or(3) aryl, heteroaryl, heterocyclyl or cycloalkyl radical optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, alkyl or haloalkyl;each R.sub.32 is independently(1) hydrogen radicals;(2) alkyl radical optionally substituted by an cycloalkyl, aryl, heterocyclyl or heteroaryl radical optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, alkyl or haloalkyl; or(3) aryl, heteroaryl, heterocyclyl or cycloalkyl radical optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, alkyl or haloalkyl; andeach R.sub.33 is independently(1) hydrogen radical; or(2) alkyl radical optionally substituted by a radical of heterocyclyl, aryl or heteroaryl optionally substituted by 1-3 radicals of amino, alkylamino, dialkylamino, alkanoylamino, alkoxycarbonylamino, alkylsulfonylamino, hydroxy, alkoxy, alkylthio, cyano, alkyl or haloalkyl; andprovided that the compound is not 3-phenyl-2-(trifluoromethylpyrazolyl)pyridine; and when X is C--H, then Q is other than a phenyl radical; and when X is N and J is C--R.sub.1 or C--R.sub.2, R.sub.11 is other than an (alkylsulfonyl)phenyl, (aminosulfonyl)phenyl, (haloalkylsulfonyl)phenyl, 4-(trifluoromethylcarbonylaminosulfonyl)phenyl, 4-(methylaminosulfonyl)phenyl or 4-(tertbutylaminosulfonyl)phenyl radical.