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Epothilone derivatives

  • US RE41,911 E1
  • Filed: 08/11/2009
  • Issued: 11/02/2010
  • Est. Priority Date: 07/08/1997
  • Status: Expired due to Term
First Claim
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1. A compound of the formula:

  • embedded imagewherein;

    Q is selected from the group consisting of;

    embedded imageG is selected from the group consisting of alkyl;

    substituted alkyl;

    substituted aryl;

    a 4 to 7 membered monocyclic, 7 to 11 membered bicyclic, or 10 to 15 membered tricyclic saturated or unsaturated ring system having between 1 and 3 heteroatoms selected from nitrogen, oxygen, and sulfur;

    embedded imageW is O or NR15;

    X is O or H, H;

    Y is selected from the group consisting of O;

    H, OR16;

    OR17, OR17;

    NOR18;

    H,NHOR19;

    H, NR20R21;

    H, H; and

    CHR22;

    wherein OR17, OR17 can be a cyclic ketal;

    Z1 and Z2 are independently CH2;

    B1 and B2 are independently selected from the group consisting of OR24, OCOR25, and O—

    C(═

    O)—

    NR26R27, and when B1 is OH and Y is OH, H, they can form a six-membered ring ketal or acetal;

    R1, R2, R3, R4, R5, R7, R13, R14, R18, R19, R20, R21, R22, R26 and R27 are selected from the group consisting of H, alkyl, substituted alkyl, and aryl, and when R1 and R2 are alkyl can be joined to form a cycloalkyl, and when R3 and R4 are alkyl can be joined to form a cycloalkyl;

    R6 is methyl;

    R9, R10, R16, R17, R24, R25 and R31 are selected from the group consisting of H, alkyl, and substituted alkyl;

    R11, R12, R28, R30, R32, and R33 are selected from the group consisting of H;

    alkyl;

    substituted alkyl;

    aryl;

    substituted aryl;

    cycloalkyl containing 1 to 3 rings and 3 to 7 carbons per ring which may be further fused with an unsaturated C3-C7 carbocyclic ring; and

    a 4 to 7 membered monocyclic, 7 to 11 membered bicyclic, or 10 to 15 membered tricyclic saturated or unsaturated ring system having between 1 and 3 heteroatoms selected from nitrogen, oxygen, and sulfur;

    R8 is hydrogen or methyl;

    R15, R23 and R29 are selected from the group consisting of H;

    alkyl;

    substituted alkyl;

    aryl;

    substituted aryl;

    cycloalkyl containing 1 to 3 rings and 3 to 7 carbons per ring which may be further fused with an unsaturated C3-C7 carbocyclic ring;

    a 4 to 7 membered monocyclic, 7 to 11 membered bicyclic, or 10 to 15 membered tricyclic saturated or unsaturated ring system having between 1 and 3 heteroatoms selected from nitrogen, oxygen, and sulfur;

    R32C═

    O;

    R33SO2;

    hydroxy;

    O-alkyl or O-substituted alkyl;

    or pharmaceutically acceptable salts thereof, hydrates, solvates or geometric, optical or stereoisomers thereof;

    with the proviso that compounds wherein W and X are both O; and

    R1, R2 and R7 are H; and

    R3, R4 and R6 are methyl; and

    R8 is H or methyl; and

    G is 1-methyl-2-(substituted-4-thiazolyl)ethenyl; and

    Q is as defined above are excluded.

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