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SUBSTITUTED HETEROCYCLIC DERIVATIVES AND THEIR PHARMACEUTICAL USE AND COMPOSITIONS

  • US 20080280879A1
  • Filed: 05/08/2008
  • Published: 11/13/2008
  • Est. Priority Date: 05/09/2007
  • Status: Abandoned Application
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1. A compound of the formula:

  • or a pharmaceutically acceptable salt or prodrug thereof or a hydrate or solvate of such compound, salt or prodrug wherein;

    at least one of X1, X2, X3, X4, X5, or X6 is selected from N or N-oxide and the remaining are selected from N or CR1;

    each R1 is independently selected from hydrogen, halogen, cyano, (C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkyl, amino, hydroxyl, thiol, or (C1-C6)alkylthio;

    R2 is independently selected from hydrogen, hydroxyl, halogen, amino, (C1-C6)alkyl, (C1-C6)alkylthio, (C3-C10)cycloalkyl, (C3-C10)cycloalkyl(C1-C6)alkyl, (C1-C6)alkyl(C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C2-C9)heterocyclo(C1-C6)alkyl, (C6-C10)aryloxy, (C2-C9)heterocycloxy, (C2-C9)heterocyclo(C1-C6)alkoxy, (C1-C6)alkoxy, (C1-C6)alkoxy(C1-C6)alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoromethoxy, difluoromethoxy, trifluoromethoxy, (C3-C10)cycloalkyloxy, (C3-C10)cycloalkylthio, (C1-C6)acyloxy, cyano, nitro, where any of the aforementioned groups (with the exception of hydrogen, halogen, hydroxyl, cyano, and nitro) is optionally substituted with at least one moiety selected from (C1-C6)alkyl, (C3-C10)cycloalkyl, (C1-C6)alkoxy, (C3-C10)cycloalkoxy, (C6-C10)aryl, (C5-C9)heteroaryl, carboxyl, (C1-C6)alkyloxycarbonyl, (C3-C10)cycloalkyloxycarbonyl, (C1-C6)acyl, halogen, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C5)alkylsulfonyl, aminocarbonyl, ((C1-C6)alkyl)aminocarbonyl, ((C1-C6)alkyl)2aminocarbonyl, hydroxyl, (C2-C9)heterocycloxy, (C6-C10)aryloxy, or (C1-C6)acyloxy;

    X7 is selected from O, NR5, CH2, —

    S—

    , SO, or SO2 or —

    CR5H—

    ;

    R4 is selected from hydrogen, hydroxyl, (C1-C6)alkoxy, fluoro, NH2, ((C1-C6)alkyl)NH, ((C1-C6)alkyl)2N or (C2-C9)heterocycloalkyl, cyano, or (C1-C6)alkylthio;

    R5 is selected from hydrogen, (C1-C6)alkyl, (C1-C6)alkyloxycarbonyl, aminocarbonyl, (C1-C6)alkylsulfonyl, or (C1-C6)alkylcarbonyl;

    D is C is selected from wherein indicates a point of attachment;

    Y1 is CR6 where R6 is selected from hydrogen, hydroxyl, halogen, (C1-C6)alkyl or R7;

    or Y1 is N; and

    wherein one of the carbon ring atoms of each of the foregoing C ring groups, together with the group to which it is attached, may optionally be replaced by —

    C(O)—

    ;

    each R7 is independently selected from hydrogen, halogen, hydroxyl, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, trifluoromethoxy, or amino provided that when Y1 is N and R7 is hydroxyl, (C1-C6)alkoxy, amino, trifluoromethoxy, or halogen, R7 may not be located on an atom adjacent to Y1;

    R8 is selected from (C6-C10)aryl, (C6-C10)aryloxy, (C6-C10)aryl(C1-C6)alkyl, (C6-C10)aryl(C1-C6)alkoxy, (C3-C10)cycloalkyl, (C3-C10)cycloalkoxy, (C3-C10)cycloalkyl(C1-C6)alkoxy, C3-C10)cycloalkyl(C1-C6)alkyl, (C5-C9)heteroaryl(C1-C6)alkyl, (C5-C9)heteroaryl, (C5-C9)heteroaryl(C1-C6)alkoxy, (C5-C9)heteroaryloxy, (C3-C10)cycloalkoxy(C1-C6)alkyl, (C2-C9)heterocycloalkyl, (C2-C9)heterocycloxy, (C2-C9)heterocyclo(C1-C6)alkyl, (C2-C9)heterocyclo(C1-C6)alkoxy, where any of the aforementioned groups may be optionally substituted with 1 to 4 moieties each independently selected from halogen, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkoxy(C1-C6)alkyl, carboxyl, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, thiol (C1-C6)alkylthio, hydroxyl, nitro, cyano, amino, mono- or di-(C1-C6)alkylamino, (C6-C10)aryl, (C5-C9)heteroaryl, (C1-C6)alkoxycarbonyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, (C3-C10)cycloalkyl, (C1-C6)alkylcarbonyl, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, aminocarbonyl, mono- and di-(C1-C6)alkylaminocarbonyl, (C1-C6)acylthio, or (C1-C6)acyloxy;

    or R7 and R8 together with the atoms to which they are bonded form a three to eight membered saturated or unsaturated or aromatic ring system that may be monocyclic or bicyclic, wherein said ring system may optionally contain at least one heteroatom selected from nitrogen, oxygen or sulfur, and wherein said ring system may be optionally substituted with 1 to 4 moieties each independently selected from hydroxyl, halogen, cyano, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, (C3-C10)cycloalkyl, (C3-C10)cycloalkoxy, formyl, (C1-C6)acyl, (C1-C6)alkoxycarbonyl, (C2-C9)heterocycloalkyl, (C6-C10)aryl, or (C5-C9)heteroaryl;

    R9 is selected from carboxyl, (C1-C6)alkoxycarbonyl, aminocarbonyl, (C1-C6)alkylaminocarbonyl, (C1-C6)alkylsulfonylaminocarbonyl, hydroxyl, hydroxymethyl, or tetrazole;

    R10 is selected from hydrogen, halogen, hydroxyl, (C1-C6)alkyl or halo(C1-C6)alkyl;

    n is 0, 1, 2, or 3;

    m is 0, 1, 2, or 3;

    p is 0 or 1; and

    q is 0, 1 or 2.

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