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Compounds useful in the treatment of inflammatory diseases

  • US 6,867,192 B1
  • Filed: 12/16/1999
  • Issued: 03/15/2005
  • Est. Priority Date: 12/18/1998
  • Status: Expired due to Term
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Assignment
First Claim
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1. A compound of formula I:

  • embedded imagewherein R1 and R2 independently represent(i) —

    C1-6 alkyl, —

    C3-8 cycloalkyl or —

    C1-3 alkylC3-8 cycloalkyl, or such a group in which alkyl or cycloalkyl is substituted by one or more halogen, —

    CN, nitro, hydroxy or —

    OC1-6 alkyl groups;

    (ii) —

    (CH2)eAr1 or —

    (CH2)eOAr1;

    or NR1R2 together represent pyrrolidinyl, piperidinyl, piperazinyl, thiomorpholinyl, morpholinyl or azepinyl, or such a group fused to a benzene ring, optionally substituted by one or more —

    (CO)n(CH2)tAr1, —

    (CO)nC1-6 alkylAr1Ar2, —

    (CO)nC1-6alkyl, —

    (CH2)rOH, —

    (CH2)rO(CH2)pOH, —

    (CH2)rOC1-6 alkyl, —

    O(CH2)tAr1, —

    (CH2)rSO2Ar1, piperidin-1-yl, —

    (CH2)tCONR8R9, —

    NR10(CO)n(CH2)tAr1, —

    NR10(CO)nC1-3alkylC3-6 cycloalkyl, —

    NR10(CO)nC1-6 alkyldiC3-6 cycloalkyl, —

    CONR10(CH2)tAr1, halogen, —

    NHSO2C1-6alkyl, —

    SO2NR10R11, —

    SO2C1-6 alkyl or —

    SO2Ar2 groups;

    R3 represents —

    C1-6alkylNHC(═

    NH)NH2, —

    C2-6alkenylNHC(═

    NH)NH2, —

    C2-6alkynylNHC(═

    NH)NH2, —

    C1-6alkylNR14R18, —

    (CH2)hCONR14R18, —

    (CH2)hCOC1-6alkyl, —

    (CH2)dCHNR18CONR20R21, —

    (CH2)mNR18CONR14R18, —

    (CH2)dNR18Ar3, —

    (CH2)dCONR18Ar3, —

    (CH2)hCOOR18, —

    (CH2)cAr3, —

    O(CH2)cAr3, —

    (CH2)dCO(CH2)sAr3 or —

    (CH2)dOAr3;

    or R3 represents —

    (CH2)c-2,4-imidazolidinedione, —

    (CH2)c(piperidin-4-yl), —

    (CH2)c(piperidin-3-yl), —

    (CH2)c(piperidin-2-yl), —

    (CH2)c(morpholin-3-yl) or —

    (CH2)c(morpholin-2-yl) optionally substituted on nitrogen by —

    (CO)fC1-6alkyl, —

    (CO)f(CH2)cAr2 or —

    C(═

    NH)NH2;

    or R3 represents —

    (CH2)zdibenzofuran optionally substituted by —

    C1-6alkyl or halogen;

    or R3 represents —

    (CH2)c-thioxanthen-9-one;

    R4 represents hydrogen, —

    C1-6 alkyl, —

    C1-3 alkylC3-6 cycloalkyl, —

    (CH2)qAr2, —

    C1-4alkyl-X—

    R7, —

    C1-4alkyl SO2C1-4 alkyl, —

    C1-6alkylNR12R13 or —

    C1-6 alkylNR12COC1-6 alkyl;

    R5 represents hydrogen, or R4R5 together with the carbon to which they are attached form a C5-7 cycloalkyl ring;

    R6 represents hydrogen or —

    C1-6alkyl;

    R7 represents hydrogen, —

    (CH2)wNR12R13, —

    (CH2)uAr2 or —

    (CH2)wNR12COC1-6 alkyl;

    R8, R9, R16 and R17 independently represent hydrogen, —

    C1-6alkyl, —

    C3-6cycloalkyl, —

    C1-3 alkylC3-6 cycloalkyl, —

    C2-6alkenyl or NR8R9 or NR16R17 together represents morpholinyl, pyrrolidinyl, piperidinyl, piperazinyl or piperazinyl N-substituted by —

    C1-6 alkyl, —

    COphenyl or —

    SO2methyl;

    R10, R11, R12, R13, R15, R18, R20 and R21 independently represent hydrogen or —

    C1-6alkyl;

    R14, R19 and R22 independently represent hydrogen, —

    C1-6alkyl, —

    C3-6 cycloalkyl or —

    (CH2)xAr4 or NR14R18 or NR15R22 together represents morpholinyl, pyrrolidinyl, piperidinyl, piperazinyl or N—

    C1-6alkylpiperazinyl;

    Ar1 represents phenyl or a 5 or 6 membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S optionally substituted by one or more halogen, —

    C1-6alkyl, hydroxy, —

    OC1-6alkyl, —

    CF3, nitro, —

    Ar2 or —

    OAr2 groups;

    Ar2 represents phenyl optionally substituted by one or more halogen, —

    C1-6alkyl, hydroxy, —

    OC1-6alkyl, —

    CF3 or nitro groups;

    Ar3 represents phenyl, a 5 or 6 membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N or S, or such a group fused to a benzene ring, optionally substituted by one or more —

    CO(CH2)gAr4, —

    (CH2)yAr4, —

    (CH2)yCOAr4, —

    (CO)aC1-6 alkyl, —

    (CO)aC2-6 alkenyl, —

    (CO)aC2-6 alkynyl, —

    (CO)aC3-8cycloalkyl, —

    (CO)aC1-6haloalkyl, halogen, —

    COCH2 CN, —

    (CH2)bNR16R17, —

    (CH2)bNHC(═

    NH)NH2, —

    CYNR16(CO)aR17, —

    (CH2)bNR15COR19, —

    (CH2)bCONR15R22, —

    (CH2)bNR15CONR15R22, —

    (CH2)bCONR15(CH2)jNR15R22, —

    (CH2)bSO2NR15R22, —

    (CH2)bSO2NR15COAr2, —

    (CH2)bNR15SO2R19, —

    SO2R19, —

    SOR19, —

    (CH2)zOH, —

    COOR15, —

    CHO, —

    OC1-10alkyl, —

    O(CH2)jNR15R22, —

    O(CH2)jNHC(═

    NH)NH2, —

    O(CH2)bCONR16R17, —

    O(CH2)kCOOR15, —

    O(CH2)jOAr2, —

    O(CH2)bAr2, 3-phenyl-2-pyrazolin-5-one or 4,5-dihydro-3(2H)-pyridazinone groups;

    Ar4 represents phenyl or a 5 or 6 membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S optionally substituted by one or more halogen, —

    C1-6alkyl, hydroxy, —

    OC1-6alkyl, —

    CF3, nitro or —

    CONH2 groups;

    X and Y independently represent O or S;

    a, f, k, s and n independently represent 0 or 1;

    b, c, r, x, y and z independently represent an integer 0 to 2;

    d, g and u independently represent 1 or 2;

    e, h, q and w independently represent an integer 1 to 3;

    j and p independently represent an integer 2 to 4;

    m independently represents an integer 0 to 4;

    t independently represents an integer 0 to 3;

    or salts or solvates thereof.

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