Patent ID: 6534502
Filing Date: 2003-03-18
Classification: C07D

Abstract:
A compound represented by the structural formula or a pharmaceutically acceptable salt thereof, wherein:a is 0, 1, 2 or 3; b and d are independently 0, 1 or 2; R is H, C1-6 alkyl, â€”OR6 or â€”F; A is &boxH;Nâ€”OR1 or &boxH;Nâ€”N(R2)(R3); when d is not 0, X is a bond, â€”C(O)â€”, â€”Oâ€”, â€”NR9â€”, â€”S(O)eâ€”, â€”N(R6)C(O)â€”, â€”C(O)N(R6)â€”, â€”OC(O)NR6â€”, â€”OC(&boxH;S)NR6â€”, â€”N(R6)C(&boxH;S)Oâ€”, â€”S(O)2N(R6)â€”, â€”N(R6)S(O)2â€”, â€”N(R6)C(O)Oâ€”, â€”OC(O)â€” or â€”N(R6)C(O)NR7â€”; and when d is 0, X is a bond or â€”NR6â€”; T is H, R4-aryl, R4-heterocycloalkyl or R4-heteroaryl; Q is R5-phenyl, R5-naphthyl or R5-heteroaryl; R1 is H, C1-6 alkyl, â€”(C(R6)(R7))nâ€”G, â€”G2, â€”(C(R6)(R7))pâ€”Mâ€”)(C(R13)(R14))nâ€”G or â€”(C(R6)(R7))pâ€”Mâ€”(R4-heteroaryl); R2 and R3 are independently selected from the group consisting of H, C1-6 alkyl, â€”(C(R6)(R7))nâ€”G, â€”G2 and â€”S(O)eR13; or R2 and R3, together with the nitrogen to which they are attached, form a ring of 5 to 6 members, wherein 0, 1 or 2 ring members are selected from the group consisting of â€”Oâ€”, â€”Sâ€” and â€”N(R19)â€”; R4 and R5 are independently 1-3 substituents independently selected from the group consisting of H, halogeno, â€”OR6, â€”OC(O)R6, â€”OC(O)N(R6)(R7), â€”N(R6)(R7), C1-6 alkyl, â€”CF3, â€”C2F5, â€”COR6, â€”CO2R6, â€”CON(R6)(R7), â€”S(O)eR13, â€”CN, â€”OCF3, â€”OCHF2, â€”NR6CO2R16, â€”NR6COR7, â€”NR8CON(R6)(R7), NO2, â€”N(R6)S(O)2R13 or â€”S(O)2N(R6)(R7); or adjancent R4 substituents or adjacent R5 substituents can form a â€”Oâ€”CH2â€”Oâ€” group; R6, R7, R8, R13 and R14 are independently selected from the group consisting of H, C1-6 alkyl, C2-C6 hydroxyalkyl, C1-C6 alkoxy-C1-C6 alkyl, R15-phenyl, and R15-benzyl; R9 is independently selected from the group consisting of R6 and â€”OR6; or R6 and R7, or R7 and R9, together with the nitrogen to which they are attached, form a ring of 5 to 6 members, wherein 0, 1 or 2 ring members are selected from the group consisting of â€”Oâ€”, â€”Sâ€” and â€”N(R19)â€”; R6a, R7a, R8a, R9a, R10 and R10a are independently selected from the group consisting of H and C1-6 alkyl; R15 is 1 to 3 substituents independently selected from the group consisting of H, â€”OH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogeno, â€”CF3, â€”C2F5, â€”COR10, â€”CO2R10, â€”C(O)N(R10)2, â€”S(O)eR10a, â€”CN, â€”N(R10)COR10, â€”N(R10)CON(R10)2 and â€”NO2; R16 is C1-6 alkyl, R15-phenyl or R15-benzyl; R19 is H, C1-C6 alkyl, â€”C(O)N(R10)2 or â€”CO2R10; n and p are independently 1-6; G is selected from the group consisting of H, R4-aryl, R4-hetero-cycloalkyl, R4-heteroaryl, R4-cycloalkyl, â€”CH2F, â€”CHF2, â€”CF3, â€”OR6, â€”N(R6)(R7), â€”COR6, â€”CO2R6, â€”CON(R7)(R9), â€”S(O)eR13, â€”NR6CO2R16, â€”NR6COR7, â€”NR8CON(R6)(R7), â€”N(R6)S(O)2R13, â€”N(R6)S(O)2N(R33)(R34), â€”S(O)2N(R6)(R7), â€”OC(O)R6, â€”OC(O)N(R6)(R7), â€”C(&boxH;NOR8)N(R6)(R7), â€”C(&boxH;NR25)N(R6)(R7), â€”N(R8)C(&boxH;NR25)N(R6)(R7), â€”CN, â€”C(O)N(R6)OR7, and â€”C(O)N(R9)-(R4-heteroaryl), provided that when n is 1, G is not â€”OH or â€”N(R6)(R7); M is selected from the group consisting of a double bond, â€”Oâ€”, â€”N(R6)â€”, â€”C(O)â€”, â€”C(R6)(OR7)â€”, â€”C(R8)(N(R6)(R7))â€”, â€”C(&boxH;NOR6)N(R7)â€”, â€”C(N(R6)(R7))&boxH;NOâ€”, â€”C(&boxH;NR25)N(R6)â€”, â€”C(O)N(R9)â€”, â€”N(R9)C(O)â€”, â€”C(&boxH;S)N(R9)â€”, â€”N(R9)C(&boxH;S)â€” and â€”N(R6)C(O)N(R7)â€”, provided that when n is 1, G is not OH or â€”NH(R6); and when p is 2-6, M can also be â€”N(R6)C(&boxH;NR25)N(R7)â€” or â€”OC(O)N(R6)â€”; G2 is R4-aryl, R4-heterocycloalkyl, R4-heteroaryl, R4-cycloalkyl, â€”COR6, â€”CO2R16, â€”S(O)2N(R6)(R7) or â€”CON(R6)(R7); e is 0, 1 or 2, provided that when e is 1 or 2, R13 and R10a are not H; R25 is H, C1-C6 alkyl, â€”CN, R15-phenyl or R15-benzyl; Z is j is 0-2; X1 is â€”Oâ€”, â€”Sâ€” or â€”NR9â€”; J1 and J2 are independently selected from the group consisting of two hydrogen atoms, &boxH;O, &boxH;S, &boxH;NR9 and &boxH;NOR1; R27 and R29 are independently selected from the group consisting of H, C1-6 alkyl, â€”(C(R6)(R7))nâ€”G, â€”G2, â€”C(O)â€”(C(R8)(R9))nâ€”G and â€”S(O)eR13; R28 is H, â€”(C(R6)(R7))tâ€”G or â€”CON(R6)(R7); t is 0, 1, 2 or 3, provided that when j is 0, t is 1, 2 or 3; and R33 and R34 are independently selected from the group consisting of H, C1-C6 alkyl, R15-phenyl and R15-benzyl; wherein heteroaryl is a 5- to 10-membered single or benzofuzed aromatic ring comprising 1 to 4 heteroatoms independently selected from the group consisting of â€”Oâ€”, â€”Sâ€” and â€”N&boxH;, provided that the rings do not include adjacent oxygen atoms, adjacent sulfur atoms, or adjacent oxygen and sulfur atoms; and wherein heterocycloalkyl is a 4- to 6-membered saturated ring comprising 1 to 3 heteroatoms independently selected from the group consisting of â€”Oâ€”, â€”Sâ€” and â€”N(R19)â€”, with the remaining members being carbon.