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KINASE INHIBITORS

  • US 20090124602A1
  • Filed: 08/07/2008
  • Published: 05/14/2009
  • Est. Priority Date: 01/31/2007
  • Status: Active Grant
First Claim
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1. A compound represented by the following structural formula:

  • or a pharmaceutically acceptable salt thereof, wherein;

    B is a monocyclic heteroaromatic ring, a 6,6 bicyclic heteroaromatic ring, or a 6,5 bicyclic heteroaromatic ring wherein B is optionally and independently substituted with R12′ and

    independently optionally and independently substituted with one or more R12 groups in addition to R3, and the point of attachment to —

    C(Z)- of the 6,5 bicyclic ring is on the 6 membered ring;

    Z is O or S;

    R1 is —

    H, halogen, —

    CN, —

    NO2, or -T1-Q1;

    T1 is absent or C1-10 aliphatic, wherein up to three methylene units of T1 are optionally and independently replaced by G wherein G is —

    O—

    , —

    S—

    , —

    S(O)—

    , —

    S(O)2

    , —

    N(R4)—

    , or —

    C(O)—

    ;

    T1 is optionally and independently substituted with one or more JT1;

    Q1 is absent, a 3-8-membered saturated, partially unsaturated, or fully unsaturated monocyclic ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, and sulfur, or an 8-12 membered saturated, partially unsaturated, or fully unsaturated bicyclic ring system having 0-5 heteroatoms independently selected from nitrogen, oxygen, and sulfur, wherein Q1 is optionally and independently substituted with J1 and independently optionally and independently substituted with one or more R13 groups;

    J1 is —

    Y1-M1;

    Y1 is absent, oxo, or C1-10 aliphatic wherein up to three methylene units of Y1 are optionally and independently replaced with G1 wherein G1 is —

    N(R$)—

    , —

    O—

    , —

    S—

    , —

    C(O)—

    , —

    S(O)—

    , or —

    S(O)2

    , Y1 is optionally and independently substituted with one or more JT1;

    M1 is C1-6 aliphatic, C3-8 cycloaliphatic, halo C1-4 aliphatic, —

    O(halo C1-4 aliphatic), 3-8 membered heterocyclyl, 5-6 membered heteroaryl, phenyl, —

    OR$, —

    SR$, —

    N(R$)2, —

    C(O)R$, —

    C(O)2R$, —

    C(O)N(R$)2, —

    OC(O)R$, —

    OC(O)N(R$)2, —

    NR$C(O)R$, —

    NR$C(O)2R$, —

    NR$C(O)N(R$)2, —

    SO2N(R$)2, —

    NR$S(O)2R$, —

    S(O)R$, —

    S(O)2R$, —

    P(O)R$, —

    P(O)2R$, —

    P(O)(R$)2, or —

    PO(OR$)2;

    M1 is optionally and independently substituted with one or more J;

    or M1 is absent, halogen, —

    N(O)2, or —

    CN;

    R2 is —

    H, halogen, —

    CN, —

    N(O)2, or optionally and independently substituted C1-C6 alkyl;

    R3 is halogen, —

    CN, —

    NO2, or -T2-Q2;

    T2 is absent or C1-10 aliphatic, wherein up to three methylene units of T2 are optionally and independently replaced by G′

    wherein G′

    is —

    O—

    , —

    S—

    , —

    S(O)—

    , —

    S(O)2

    , —

    N(R4)—

    , or —

    C(O)—

    ;

    T2 is optionally and independently substituted with one or more JT2;

    Q2 is absent, a 3-8-membered saturated, partially unsaturated, or fully unsaturated monocyclic ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, and sulfur, or an 8-12 membered saturated, partially unsaturated, or fully unsaturated bicyclic ring system having 0-5 heteroatoms independently selected from nitrogen, oxygen, and sulfur, wherein Q2 is optionally and independently substituted with J2 and independently optionally and independently substituted with one or more R13 groups;

    wherein when R1 and R2 are —

    H, R12 is absent, R12 is absent, Z is O, R3 is -T2-Q2 then -T2-Q2 is not absent, —

    NHCH2CH(OH)CH2OH, or J2 is —

    Y2-M2;

    Y2 is absent, oxo, or C1-10 aliphatic, wherein up to three methylene units of Y2 are optionally and independently replaced with G1′

    wherein G1′

    is —

    N(R$)—

    , —

    O—

    , —

    S—

    , —

    C(O)—

    , —

    S(O)—

    , or —

    S(O)2

    , Y2 is optionally and independently substituted with one or more JT2;

    M2 is C1-6 aliphatic, C3-8 cycloaliphatic, halo C1-4 aliphatic, —

    O(halo C1-4 aliphatic), 3-8 membered heterocyclyl, heteroaryl, aryl, —

    OR$, —

    SR$, —

    N(R$)2, —

    C(O)R$, —

    C(O)2R$, —

    C(O)N(R$)2, —

    OC(O)R$, —

    OC(O)N(R$)2, —

    NR$C(O)R$, —

    NR$C(O)2R$, —

    NR$C(O)N(R$)2, —

    SO2N(R$)2, —

    NR$S(O)2R$, —

    S(O)R$, —

    S(O)2R$, —

    P(O)R$, —

    P(O)2R$, —

    P(O)(R$)2, or —

    PO(OR$)2;

    wherein M2 is optionally and independently substituted with one or more J;

    or M2 is absent, halogen, —

    N(O)2, or —

    CN;

    each J is independently halogen, C1-6 aliphatic, C3-6 cycloaliphatic, —

    NO2, —

    CN, —

    N(R$)2, —

    OR$, —

    C(O)R$, —

    C(O)N(R$)2, —

    C(O)2R$, oxo, —

    O(haloC1-4 aliphatic), or halo C1-4 aliphatic;

    R4 is —

    H or an optionally and independently substituted C1-C6 alkyl;

    each JT1 is independently halogen, —

    CN, —

    N(O)2, or hydroxy;

    each JT2 is independently halogen, —

    CN, —

    N(O)2, or hydroxy;

    each R$ is independently —

    H or C1-C6 alkyl;

    each R12 is independently halogen, amino, aminoalkyl, alkylaminoalkyl, alkoxy, hydroxy, —

    CN, —

    NO2, or optionally and independently substituted C1-C6 alkyl;

    each R12

    is independently halogen, amino, aminoalkyl, alkylaminoalkyl, alkoxy, hydroxy, —

    CN, —

    NO2, or optionally and independently substituted C1-C10 aliphatic wherein up to three methylene units are optionally and independently replaced by G′

    wherein G′

    is —

    O—

    , —

    S(O)p

    , —

    N(R4)—

    , or —

    C(O)—

    , and each methylene unit is optionally and independently substituted with one or more JT3;

    or each R12 is cycloaliphatic, phenyl, heteroaryl, each independently and optionally substituted with one or more JT4;

    each JT3 is independently halogen, —

    CN, —

    NO2, cycloaliphatic, or phenyl;

    each JT4 is independently halogen, C1-C6 alkyl, or C1-C6 alkoxy;

    each R13 is independently halogen, amino, aminoalkyl, alkylaminoalkyl, alkoxy, hydroxy, —

    CN, —

    NO2, oxo or optionally and independently substituted C1-C6 alkyl; and

    p is 0, 1 or 2;

    with the proviso the compound is not (2-amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl)(6-aminopyridin-3-yl)methanone, (2-amino-5-bromopyridin-3-yl)(6-(2-methoxyethylamino)pyridin-3-yl)methanone, (2-amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl)(6-(2-methoxyethylamino)pyridin-3-yl)methanone, (2-amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl)(6-(isobutylamino)pyridin-3-yl)methanone, (2-amino-5-bromopyridin-3-yl)(6-fluoropyridin-3-yl)methanone, methanone (2-amino-5-chloro-3-pyridinyl)-4-pyridinyl-, benzenesulfonamide, N-[2-[(2-amino-3pyridinyl)carbonyl]-5-chloro-3-pyridinyl]-4-chloro-(trifluoromethyl) or methanone, (2-amino-5-chloro-3-pyridinyl)-4-pyridinyl-.

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