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Dpp-IV Inhibitors

  • US 20070265261A1
  • Filed: 06/08/2005
  • Published: 11/15/2007
  • Est. Priority Date: 06/08/2004
  • Status: Abandoned Application
First Claim
Patent Images

1. A compound of the formula (I) or a pharmaceutically acceptable salt thereof, wherein Z is selected from the group consisting of phenyl;

  • naphthyl;

    indenyl;

    C3-7 cycloalkyl;

    indanyl;

    tetralinyl;

    decalinyl;

    heterocycle; and

    heterobicycle, wherein Z is optionally substituted with one or more R4, wherein R4 is independently selected from the group consisting of halogen;

    CN;

    OH;

    NH2;

    oxo (═

    O), where the ring is at least partially saturated;

    R5; and

    R6;

    R5 is selected from the group consisting of C1-6 alkyl;

    O—

    C1-6 alkyl; and

    S—

    C1-6 alkyl, wherein R5 is optionally interrupted by oxygen and wherein R5 is optionally substituted with one or more halogen independently selected from the group consisting of F; and

    Cl;

    R6 is selected from the group consisting of phenyl;

    heterocycle; and

    C3-7 cycloalkyl, wherein R6 is optionally substituted with one or more R7, wherein R7 is independently selected from the group consisting of halogen;

    CN;

    OH;

    NH2;

    oxo (═

    O), where the ring is at least partially saturated;

    C1-8 alkyl;

    O—

    C1-6 alkyl; and

    S—

    C1-6 alkyl;

    R1 is selected from the group consisting of H;

    F;

    OH; and

    R8;

    R2 is selected from the group consisting of H;

    F; and

    R9;

    R8 is independently selected from the group consisting of C1-6 alkyl;

    O—

    C1-6 alkyl;

    N(R8a)—

    C1-6 alkyl;

    S—

    C1-6 alkyl;

    C3-7 cycloalkyl;

    O—

    C3-7 cycloalkyl;

    N(R8a

    C3-7 cycloalkyl;

    S—

    C3-7 cycloalkyl;



    C1-6 alkyl-C3-7 cycloalkyl;

    O—

    C1-6 alkyl-C3-7 cycloalkyl;

    N(R8a)—

    C1-6 alkyl-C3-7 cycloalkyl;

    S—

    C1-6 alkyl-C3-7 cycloalkyl;

    heterocycle;

    O-heterocycle;

    N(R8a)-heterocycle;

    S-heterocycle;

    C1-6 alkyl-heterocycle;

    O—

    C1-6 alkyl-heterocycle;

    N(R8a)—

    C1-6 alkyl-heterocycle;

    S—

    C1-6 alkyl-heterocycle;

    wherein R8 is optionally substituted with one or more halogen independently selected from the group consisting of F; and

    Cl;

    R8a is selected from the group consisting of H; and

    C1-6 alkyl;

    R9 is independently selected from the group consisting of C1-6 alkyl;

    C3-7 cycloalkyl; and



    C3-7 alkyl-C3-7 cycloalkyl, wherein R9 is optionally substituted with one or more R9a, wherein R9a is independently selected from the group consisting of F;

    Cl; and

    OH;

    R3 is selected from the group consisting of H; and

    C1-6 alkyl;

    Optionally one or more pairs of R1, R2, R3 independently selected from the group consisting of R1/R2; and

    R2/R3;

    form a C3-7 cycloalkyl ring, which is optionally substituted with one or more of R9b, wherein R9b is independently selected from the group consisting of F;

    Cl; and

    OH;

    A is selected from the group consisting of A0; and

    A1;

    A0 is selected from the group consisting of C3-7 cycloalkyl; and

    a saturated heterocycle with at least one nitrogen as ring atom;

    wherein A0 is substituted with one or more R10a, wherein R10a is independently selected from the group consisting of NR10R10B;

    NR10S(O)2R10b;

    NR10S(O)R10b;

    S(O)2NR10R10b;

    C(O)NR10R10b;

    R10, provided that R10 is bound to a nitrogen, which is a ring atom of the saturated heterocycle; and

    C1-3 alkyl, which is optionally substituted with one or more R10c, wherein R10c is independently selected from the group consisting of F;

    C1-3 alkyl; and

    C3-4 cycloalkyl, wherein C1-3 alkyl and C3-4 cycloalkyl are optionally substituted with one or more F;

    Optionally R10a is independently selected from group consisting of F;

    Cl, and oxo (═

    O);

    A1 is selected from the group consisting of X;

    Y are independently selected from the group consisting of —

    CH2;



    NR10b

    ;



    O—

    ; and



    S—

    ;

    W is selected from the group consisting of R10, R10b are independently selected from the group consisting of T1-T2; and

    T2;

    T1 is selected from the group consisting of —

    C1-6 alkyl-;



    C1-6 alkyl-O—

    ;



    C1-6 alkyl-S—

    ;



    C1-6 alkyl-N(R11);



    C(O)—

    ;



    C(O)—

    C1-6 alkyl-;



    C(O)—

    C1-6 alkyl-O—

    ;



    C(O)—

    C1-6 alkyl-S—

    ;



    C(O)C1-6 alkyl-N(R11)—

    ;



    C(O)O—

    ;



    C(O)O—

    C1-6 alkyl-;



    C(O)O—

    C1-6 alkyl-O—

    ;



    C(O)O—

    C1-6 alkyl;



    C(O)C—

    C1-6 alkyl-N(R11)—

    ;



    C(O)N(R11)—

    ;



    C(O)N(R11)—

    C1-6 alkyl-;



    C(O)N(R11)C1-6 alkyl-O—

    ;



    C(O)N(R11)—

    C1-6 alkyl-S—

    ;



    C(O)N(R11)—

    C1-6 alkyl-N(R11a)—

    ;



    S(O)2

    ;



    S(O)2

    C1-6 alkyl-;



    S(O)2

    C1-6 alkyl-O—

    ;



    S(O)2

    C1-6 alkyl-S—

    ;



    S(O)2

    C1-6 alkyl-N(R11)—

    ;



    S(O)—

    ;



    S(O)—

    C1-6 alkyl-;



    S(O)—

    C1-6 alkyl-O—

    ;



    S(O)—

    C1-6 alkyl-S—

    ; and



    S(O)—

    C1-6 alkyl-N(R11)—

    ;

    wherein each C1-6 alkyl is optionally substituted with one or more halogen selected from the group consisting of F; and

    Cl;

    R11, R11a are independently selected from the group consisting of H;

    C1-6 alkyl;

    C3-7 cycloalkyl; and



    C1-6 alkyl-C3-7 cycloalkyl;

    T2 is selected from the group consisting of H;

    T3; and

    T4;

    T3 is selected from the group consisting of phenyl;

    naphthyl; and

    indenyl;

    wherein T3 is optionally substituted with one or more R12;

    wherein R12 is independently selected from the group consisting of halogen;

    CN;

    COOR13;

    OC(O)R13;

    OR13;



    C1-6alkyl-OR13;

    SR13;

    S(O)R13;

    S(O)2R13;

    C(O)N(R13R14);

    S(O)2N(R13R14);

    S(O)N(R13R14);

    C1-6 alkyl;

    N(R13)S(O)2R14; and

    N(R13)S(O)R14;

    wherein each C1-6 alkyl is optionally substituted with one or more halogen selected from the group consisting of F; and

    Cl;

    T4 is selected from the group consisting of C3-7 cycloalkyl;

    indanyl;

    tetralinyl;

    decalinyl;

    heterocycle; and

    heterobicycle;

    wherein T4 is optionally substituted with one or more R15, wherein R15 is independently selected from the group consisting of halogen;

    CN;

    OR13;



    C1-6alkyl-OR13SR13;

    oxo (═

    O), where the ring is at least partially saturated;

    N(R13R14);

    COOR13;

    OC(O)R13;

    C(O)N(R13R14);

    S(O)2N(R13R14);

    S(O)N(R13R14);

    C1-6 alkyl;

    N(R13)C(O)R14;

    S(O)2R13;

    S(O)R13;

    N(R13)S(O)2R14; and

    N(R13)S(O)R14;

    wherein each C1-6 alkyl is optionally substituted with one or more halogen selected from the group consisting of F; and

    Cl;

    Optionally R15 is C(O)R13, provided that C(O)R13 is bound to a nitrogen, which is a ring atom of a heterocycle or heterobicycle;

    R13, R14 are independently selected from the group consisting of H;

    C1-6 alkyl;

    C3-7 cycloalkyl; and



    C1-6 alkyl-C3-7 cycloalkyl;

    wherein each C1-4 alkyl is optionally substituted with one more halogen selected from the group consisting of F; and

    Cl.

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