Patent ID: 6559152
Filing Date: 2003-05-06
Classification: A61P,C07D

Abstract:
A compound of formula (I) or its tautomer, formula (II): or a stereoisomer or pharmaceutically acceptable salt form thereof, wherein:Q is selected from the group consisting of: H, OH, and C1-7 alkyl; Y is selected from the group consisting of: F, Cl, Br, and I; Z is selected from the group consisting of: N, Câ€”H, Câ€”F, Câ€”Cl, Câ€”Br, Câ€”I, Câ€”CF3, Câ€”NO2, Câ€”C1-4 alkyl optionally containing from 1-8 substitution groups, Câ€”C2-4 alkenyl optionally containing from 1-8 substitution groups, Câ€”C2-4 alkynyl optionally containing from 1-8 substitution groups, Câ€”C1-4 alkoxy optionally containing from 1-8 substitution groups, Câ€”CO2H, Câ€”CHO, Câ€”CONR6R9, Câ€”CO2C1-3 alkyl, Câ€”C(O)C1-2 alkyl, Câ€”CH2NHR6, Câ€”CONR6NR6R9, Câ€”NR6R9; Câ€”SO2NR6R9, Câ€”CR&boxH;NNR6R9, Câ€”CR6&boxH;NOR6, and Câ€”R6; R1 is selected from the group consisting of aryl and 5-10 membered aromatic heterocycle containing from 1-4 heteroatoms selected from O, N, and S, and wherein the aryl or the 5-10 membered aromatic heterocycle is optionally substituted with 1-5 R7 groups; R2 is selected from the group consisting of: C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, Sâ€”C1-3 alkyl, Oâ€”C1-3 alkyl, NH2, NHâ€”C1-3 alkyl, N(C1-2 alkyl)2, OCF3, cyclopropyl optionally containing from 1-4 substitution groups, cyclobutyl, cyclopropylmethyl, cyclobutylmethyl, 1-methylcyclopropyl, 1-methylcyclobutyl, CH2CN, CH2OH, CH2OCH3, CH2, NH2, CH2NHC1-3 alkyl, CH2NMe2, CF3, CHO, OCH2CH2OH, OCH(Me)CH2OH, OCH2CH(Me)OH, OCH2CH2NMe2, and CHF2; R3 is selected from the group consisting of: H, F, Cl, Br, I, CF3, CHO, CHR6OH, COCF3, CH&boxH;NOH, CH&boxH;NOCH3, CH&boxH;NNH2, CH&boxH;NNHMe, CH&boxH;NNMe2, CH&boxH;CHR6, C1-3 alkyl, C1-3 alkoxy, CO2H, CONH2, CONH(C1-3 alkyl), CONR6R9, CO2C1-3 alkyl, C(O)C1-2 alkyl, NH2, NHR6, and NR6R9; R4 is selected from the group consisting of: H, F, Cl, Br, I, CF3, C1-3 alkyl, C2-3 alkenyl, NH2, NHR6, and NR6R9; R5 is selected from the group consisting of: H, C1-3 alkyl, F, Cl, Br, I, CF3, and C2-3 alkenyl; R6 and R9 are independently, at each occurrence, the same or different, and are selected from the group consisting of: H, C1-8 alkyl optionally containing from 1-8 substitution groups, and C3-7 cyclo-alkyl; alternatively, R6 and R9, together with the atoms to which they are attached, form a heterocycle having 5-7 atoms in the ring and containing 0-1 additional N, O, or S atom; or, R6 and R9, together with the atoms to which they are attached, form a bicyclic heterocycle having 9-11 atoms in the ring and containing one additional N, S, or O atom; or, R6 and R9, together with the atoms to which they are attached, form a 5-7 membered ring and containing 0-3 additional N, S, or O atoms; R7 is independently, at each occurrence, selected from the group consisting of: OH, C1-6 alkoxy, OC2-6 alkyl-CO2H, Oâ€”C2-6-alkyl-NR6R9, F, Cl, Br, I, CF3, OCF3, â€”CN, â€”NO2, CO2H, CO2(C1-6 alkyl), CONR6R9, NR6CONHOR6, NR6CONHSO2R6, NHNR6C(O)OR6, NR6C(O)NR6R9, NH2, NH(C1-3 alkyl), N(C1-3 alkyl)2, â€”SO2NR6R9, NHSO2NHCO2C1-4 alkyl, NR6SO2NR6R9, NR6SO2CHR6CH2NR6R9, NR6COCHR6NR6R9, NR6COCHR6NR6CHR6R9, NR6COCH2CHR6NR6R9, NR6COCHR6CH2NR6R9. NR6CO(CH2)mNR6R9, NR6CONR6(CH2)nNR6R9, NR6CO2(CHR6)nNR6R9, CONR6NR6R9, NR6CONR6NR6R9, C3-10 carbocycle, NHCONR6, NHCONHCH2R6, NHCOR6, NHCOCH2R6, C1-10 alkyl optionally substituted with 1-5 substitution groups, C2-10 alkenyl optionally substituted with 1-5 substitution groups, C2-10 alkynyl optionally substituted with 1-5 substitution groups, and C3-10 heterocycle containing 1-4 heteroatoms selected from O, N, and S; R8 is independently, at each occurrence, selected from the group consisting of: &boxH;O, OH, C3-6 cycloalkyl, C1-16 alkoxy, NH2, NH(C1-6 alkyl), N(C1-6 alkyl)2, F, Cl, Br, I, CO2H, COR6, CO2(benzyl), CO2(C1-6 alkyl), and CONR6R9; n at each occurrence is independently selected from 2, 3, 4, 5, and 6; and, m at each occurrence is independently selected from 3, 4, 5, and 6.