Patent ID: 6469006
Filing Date: 2002-10-22
Classification: A61P,C07D

Abstract:
A compound of formula I, including pharmaceutically-acceptable salts thereof, wherein:R1, R2, R3, R4 and R5 are each independently H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C3-C6 cycloalkenyl, C2-C6 alkynyl, halogen CN, nitro, COOR6 or XR7, each of said alkyl and cycloalkyl being optionally substituted with one to three same or different halogen, amino, OH, CN or NO2; R6 is H, C1-C6 alkyl, or C3-C6 cycloalkyl, benzyl, each of said alkyl, cycloalkyl and benzyl being optionally substituted with one to three same or different halogen, amino, OH, CN or NO2; X is O, S or NR6R7+: R7 is H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C3-C6 cycloalkenyl, C2-C6 alkynyl or C(O)R8, each of said alkyl and cycloalkyl being optionally substituted with one to three same or different halogen, OH, amino, CN or NO2; R8 is H, C1-C6 alkyl or C3-C6 cycloalkyl; â€”Wâ€” is R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22 are each independently H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C3-C6 cycloalkenyl, C2-C6 alkynyl, CR23R24OR25, COR26, COOR27 or C(O)NR28R29, each of said alkyl and cycloalkyl being optionally substituted with one to three same or different halogen, amino, OH, CN or NO2; R23, R24, R25, R26, R27, R28, R29 are each independently H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 cycloalkenyl or C2-C6 alkynyl; Ar is a 4-7 membered aromatic ring which may contain one to five heteroatoms independently selected from the group consisting of O, S, N or NR6, wherein said aromatic ring is optionally fused to group B; B is an aromatic group selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, indenyl, azulenyl, fluorenyl, and anthracenyl; or a heteroaryl group selected from the group consisting of 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrolyl, oxaz thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, and 1,3,5-trithianyl; or the resulting fused aromatic ring with B is indolizinyl, indolyl, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, benzo[b]thiophenyl, 1H-indazolyl, benzimidazolyl, benzthiazolyl, purinyl, 4H-quinolizinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 1,8-naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, or phenoxazinyl; B and said 4-7 membered aromatic ring may each independently contain one to five substituents which are each independently selected from R30 R31, R32, R33 or R34; Ra and Rb are each independently H, C1-6 alkyl or phenyl; Z is 4-methoxyphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrazyl, quinolyl, 3,5-dimethylisoxazoyl, isoxazoyl, 2-methylthiazoyl, thiazoyl, 2-thienyl, 3-thienyl, or pyrimidyl; and p is 1-2; R30 R31, R32, R33, and R34 are each independently H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C3-C6 cycloalkenyl, C2-C6 alkynyl, halogen, CN, nitro, C(O)R35, COXR36, hydroxyl, hydroxymethyl, trifluoromethyl, trifluoromethoxy, O-benzyl, O-phenyl, OC(O)C1-6 alkyl, SC(O)C1-6 alkyl, S(O)m C1-6 alkyl, S(O)2 NRaRb, amino, O-Z, CH2â€”(CH2)p-Z, Oâ€”(CH2)p-Z, (CH2)tâ€”O-Z, CH&boxH;CH-Z or XR37, each of said alkyl and cycloalkyl being optionally substituted with one to three same or different halogen, amino, OH, CN or NO2; m is 0-2; R35 and R36 are each independently H, C1-C6 alkyl or C3-C6 cycloalkyl; R37 is H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C3-C6 cycloalkenyl, C2-C6 alkynyl, C(O)R38 or C(O)OR39, each of said alkyl and cycloalkyl being optionally substituted with one to three same or different halogen, amino, OH, CN or NO2; R38, R39 are each independently H, C1-C6 alkyl or C3-C6 cycloalkyl, each of said alkyl and cycloalkyl being optionally substituted with one to three same or different halogen, amino, OH, CN or NO2; provided R39 is not H; R40 is (CH2)nâ€”Y, where n is 0-6; Y is selected from: (1) H, C1-6 alkyl, C3-6 cycloalkyl, C2-6 alkenyl, C3-6 cycloalkenyl, C2-6 alkynyl, halogen, CN, nitro, Ar, COOR6, COOAr, â€”CONRaRb, TR6, NRaRb, â€”NC(O)NRaRb, â€”OC(O)R6, â€”C[N(Ra)2]=N-T-Rb, XR6, â€”C(O)R6, â€”C(O)Ar, â€”S(O)Ra or â€”S(O)2Ra, provided when Y is â€”S(O)Ra or â€”S(O)2Ra then Ra is not H; and (2) a 4-7 membered heterocyclic ring, optionally substituted with R6, which may contain 1-3 heteroatoms selected from the group consisting of O, S, SO, SO2, N, and NR41, wherein R41 is selected from the group consisting of hydrogen, (C1-C4)-straight or branched alkyl, (C2-C4)-straight or branched alkenyl or alkynyl; T is S or O; provided R1-R5, R9-R16 and R30-R34 are not all H at the same time and Ar is phenyl; and provided R1-R5, R9-R16 and R30-R34 are not all H at the same time and Ar is 2-furyl.