Patent ID: 6414011
Filing Date: 2002-07-02
Classification: A61P,C07D

Abstract:
A compound having the Formula I: or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein:Het is a heteroaryl selected from the group consisting of R1 is selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl, aralkyl, heteroaryl, C(O)R14, CH2C(O)R14, S(O)R14, and SO2R14 all of which may be optionally substituted; R2, R3, and R4 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, aryl, aminoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, carboxyalkyl, cyano, amino, alkylamino, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, aralkylaminocarbonyl, alkylcarbonylamino, arylcarbonylamino, aralkylcarbonylamino, alkylcarbonyl, heterocyclocarbonyl, aminosulfonyl, alkylaminosulfonyl, alkylsulfonyl, and heterocyclosulfonyl, or the R groups in adjacent carbon atoms can be taken together with the carbon atoms to which they are attached to form a carbocycle or a heterocycle; R5, R6, R7, R8, R9, R10, R11, R12, and R13 are independently selected from the group consisting of hydrogen, halo, haloalkyl, aryl, cycloalkyl, saturated or partially unsaturated heterocycle, heteroaryl, alkyl, alkenyl, alkynyl, arylalkyl, arylalkenyl, arylalkynyl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, cycloalkylalkyl, heterocycloalkyl, hydroxyalkyl, aminoalkyl, carboxyalkyl, alkoxyalkyl, nitro, amino, ureido, cyano, acylamino, amide, hydroxy, thiol, acyloxy, azido, alkoxy, carboxy, carbonylamido and alkylthiol; or R9 and R10 or R10 and R11 are taken together with the carbon atoms to which they are attached to form a carbocycle or a heterocycle; R14 is selected from the group consisting of amino, alkyl, alkenyl, alkynyl, OR16, alkylamino, dialkylamino, alkenylamino, cycloalkyl, aralkyl, aryl, heteroaryl, arylalkenyl, arylalkynyl, arylalkylamino, dialkylaminoalkenyl, heterocycle, heterocycloalkylamino, and cycloalkylalkylamino, all of which can be optionally substituted; wherein R16 is selected from the group consisting of hydrogen, optionally substituted alkyl, and an alkalimetal; and X is one of O, S, NR15, NR15C(O), or C(O)NR15, wherein R15 is hydrogen, alkyl or cycloalkyl, with the provisos that: 1) when Het is (i) or (ii),a) R1 is H and X is O or S, at least one of R2, R3 and R5-R13 is other than H, except that R11 is not NO2 when R3 is CH3, and R3 is not â€”CH2CH2COOH when the other substituents are each H; b) R1 is H, X is O and one of R9-R13 is NO2 or OCH3, at least one the other substituents is other than H; c) X is O, R9 or R13 is CN and a Cl group is ortho to CN, at least one of R2, R3 and R5-R8 is other than H; d) X is O, R5 and R11 are Cl, at least one of R6, R7, R8, R9, R10, R12 and R13 is other than H; e) X is O, R2 is methylthio, R1 is H or C(O)R14 wherein R14 is optionally substituted phenyl, at least one of R5-R13 is other than H; or f) R1 is C(O)NH2 and X is O, at least one of R2, R3 and R5-R13 is other than H; or 2) when Het is (vi),a) X is O or S, R2 and R4 do not together form â€”CH&boxH;CHâ€”CH&boxH;CHâ€”; b) R1 is H and X is O or S, R5-R13 are not all H; or c) X is S and R1 and R2 both are Me, at least one of R3 and R4 is other than â€”CH2OH.