Patent ID: 6495558
Filing Date: 2002-12-17
Classification: C07D

Abstract:
A compound having the formula or a pharmaceutically acceptable salt thereof, whereinR2 is â€”NH-aryl; R3 is a phenyl substituted with 1-3 independent R4; wherein each R4 is independently selected from H; C1-C10 alkyl; C2-C10 alkenyl; C2-C10 alkynyl; C3-C10 cycloalkyl; C4-C10 cycloalkenyl; aryl; R8; halo; haloalkyl; SR5; OR5; NR5R5; COOR5; NO2; CN; C(O)R5; C(O)C(O)R5; C(O)NR5R5; OC(O)R5; S(O)2R5; S(O)2NR5R5; NR5C(O)NR5R5; NR5C(O)C(O)R5; NR5C(O)R5; NR5(COOR5); NR5C(O)R8; NR5S(O)2NR5R5; NR5S(O)2R5; NR5S(O)2R8; NR5C(O)C(O)NR5R5; NR5C(O)C(O)NR5R6; C1-C10 alkyl substituted with aryl, R7 or R8; or C1-C10 alkenyl substituted with aryl, R7 or R8; each R5 is independently H; C1-C10 alkyl; C2-C10 alkenyl; C2-C10 alkynyl; C3-C10 cycloalkyl; C4-C10 cycloalkenyl; aryl; R9; C1-C10 alkyl substituted with 1-3 independent aryl, R7 or R9 groups; C3-C10 cycloalkyl substituted with 1-3 independent aryl, R7 or R9 groups; or C1-C10 alkenyl substituted with 1-3 independent aryl, R7 or R9; each R6 is independently C(O)R5, COOR5, or S(O)2R5; each R7 is independently halo, CF3, SR10, OR10, OC(O)R10, NR10R10, NR10R11, NR11R11, COOR10, NO2, CN, C(O)R10, or C(O)NR10R10; each R8 is independently a 5-8 membered monocyclic, 8-12 membered bicyclic, or 11-14 membered tricyclic ring system having 1-3 heteroatoms if monocyclic, 1-6 heteroatoms if bicyclic, or 1-9 heteroatoms if tricyclic, said heteroatoms selected from O, N, or S, which may be saturated or unsaturated, and wherein 0, 1, 2 or 3 atoms of each ring may be substituted by a substituent independently selected from C1-C10 alkyl; C2-C10 alkenyl; C2-C10 alkynyl; C3-C10 cycloalkyl; C4-C10 cycloalkenyl; aryl; R9; halo; sulfur; oxygen; haloalkyl; SR5; OR5; OC(O)R5; NR5R5; NR5R6; NR6R6; COOR5; NO2; CN; C(O)R5; C(O)NR5R5; C1-C10 alkyl substituted with 1-3 independent R7, R9 or aryl; or C1-C10 alkenyl substituted with 1-3 independent R7, R9 or aryl; each R9 is independently a 5-8 membered monocyclic, 8-12 membered bicyclic, or 11-14 membered tricyclic ring system having 1-3 heteroatoms if monocyclic, 1-6 heteroatoms if bicyclic, or 1-9 heteroatoms if tricyclic, said heteroatoms selected from O, N, or S, which may be saturated or unsaturated, and wherein 0, 1, 2 or 3 atoms of each ring may be substituted by a substituent independently selected from C1-C10 alkyl; C2-C10 alkenyl; C2-C10 alkynyl; C3-C10 cycloalkyl; C4-C10 cycloalkenyl; halo; sulfur; oxygen; CF3; haloalkyl; SR10; OR10; NR10R10; NR10R11; NR11R11; COOR10; NO2; CN; C(O)R10; or C(O)NR10R10; each R10 is independently H, C1-C10 alkyl; C2-C10 alkenyl; C2-C10 alkynyl; C3-C10 cycloalkyl; C4-C10 cycloalkenyl; haloalkyl; C1-C10 alkyl optionally substituted with 1-3 independent C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C4-C10 cycloalkenyl, halo, CF3, OR13, SR13, NR13R13, COOR13, NO2, CN, C(O)R13, C(O)NR13R13, NHC(O)R13, or OC(O)R13; or phenyl optionally substituted with 1-3 independent C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C4-C10 cycloalkenyl, halo, CF3, OR13, SR13, NR13R13, COOR13, NO2, CN, C(O)R13, C(O)NR13R13, NHC(O)R13, or OC(O)R13; each R11 is independently C(O)R10, COOR10, or S(O)2R10; each R12 is independently H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C4-C10 cycloalkenyl, or phenyl optionally substituted with 1-3 independent C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C4-C10 cycloalkenyl, halo, CF3, OR13, SR13, NR13R13, COOR13, NO2, CN, C(O)R13, C(O)NR13R13, NHC(O)R13, or OC(O)R13; each R13 is independently H; C1-C10 alkyl; C2-C10 alkenyl; C2-C10 alkynyl; C3-C10 cycloalkyl; C4-C10 cycloalkenyl; C1-C10 alkyl optionally substituted with halo, CF3, OR19, SR19, NR19R19, COOR19, NO2, CN; or phenyl optionally substituted with halo, CF3, OR19, SR19, NR19R19, COOR9, NO2, CN; each R19 is independently H; C1-C10 alkyl; C3-C10 cycloalkyl or phenyl; each haloalkyl is independently a C1-C10 alkyl substituted with one or more halogen atoms, selected from F, Cl, Br, or I, wherein the number of halogen atoms may not exceed that number that results in a perhaloalkyl group; and each aryl is independently a 6-carbon monocyclic or 10-carbon bicyclic aromatic ring system optionally substituted with 1-3 independent C1-C10 alkyl; C2-C10 alkenyl; C2-C10 alkynyl; C3-C10 cycloalkyl; C4-C10 cycloalkenyl; R9; halo; haloalkyl; OR12; SR12; NR12R12; COOR12; NO2; CN; C(O)R12; C(O)C(O)R12; C(O)NR12R12; S(O)2R12; N(R12)C(O)R12; N(R12)(COOR12); N(R12)S(O)2R12; S(O)2NR12R12; OC(O)R12; NR12C(O)NR12R12; NR12C(O)C(O)R12; NR12C(O)R9; NR12S(O)2NR12R12; NR12S(O)2R9; NR12C(O)C(O)NR12R12; C1-C10 alkyl substituted with 1-3 independent R9, halo, CF3, OR12, SR12, NR12R12, COOR12, NO2, CN, C(O)R12, C(O)NR12R12, NHC(O)R12, NH(COOR12), S(O)2NR12R12, OC(O)R12; C2-C10 alkenyl substituted with 1-3 independent R9, halo, CF3, OR12, SR12, NR12R12, COOR12, NO2, CN, C(O)R12, C(O)NR12R12, NHC(O)R12, NH(COOR12), S(O)2NR12R12, OC(O)R12; or R12; and provided that (1) R2 is other than unsubstituted phenyl-NHâ€”; (2) when R3 is 4-methoxyphenyl, then R2 is other than 4-methoxyphenyl-NHâ€” or 4-nitrophenyl-NHâ€”; and (3) when R3 is 2,4-dichlorophenyl, then R2 is other than 4-chlorophenyl-NHâ€”.