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Thiazole derivatives

  • US 6,720,427 B2
  • Filed: 05/13/2002
  • Issued: 04/13/2004
  • Est. Priority Date: 05/11/2001
  • Status: Expired due to Fees
First Claim
Patent Images

1. A compound of the formula embedded imagewherein R1 is a straight chain or branched (C2-C8)alkyl, a straight chain or branched (C2-C8)alkenyl, a straight chain or branched (C2-C8)alkynyl, (C3-C8)cycloalkyl, (C4-C8)cycloalkenyl, (3-8 membered) heterocycloalkyl, (C5-C11)bicycloalkyl, (C7-C11)bicycloalkenyl, (5-11 membered) heterobicycloalkyl, (C6-C14) aryl, (5-14 membered) heteroaryl, or ABN-;

  • and wherein R1 is optionally substituted with from one to six substituents R5 independently selected from F, Cl, Br, I, nitro, cyano, —

    CF3, —

    NR7R8, —

    NR7C(═

    O)R8, —

    NR7C(═

    O)OR8, —

    NR7C(═

    O)NR8R9, —

    NR7S(═

    O)2R8, —

    NR7S(═

    O)2NR8R9, —

    OR7, —

    OC(═

    O)R7, —

    OC(═

    O)OR7, —

    C(═

    O)OR7, —

    C(═

    O)R7, —

    C(═

    O)NR7R8, —

    OC(═

    O)NR7R8, —

    OC(═

    O)SR7, —

    SR7, —

    S(═

    O)R7, —

    S(═

    O)2R7, —

    S(═

    O)2NR7R8, and R7;

    A and B are each independently selected from straight or branched (C1-C8)alkyl, straight chain or branched (C2-C8)alkenyl, straight chain or branched (C2-C8)alkynyl, (C3-C6)cycloalkyl, (C4-C8)cycloalkenyl, (3-8 membered) heterocycloalkyl, (C5-C11)bicycloalkyl, (C7-C11)bicycloalkenyl, and (5-11 membered) heterocycloalkyl;

    or A and B may be connected to form a 3-8 membered heterocyclic ring optionally containing one or two double bonds and optionally containing one or two further hetero atoms selected independently from O, S, and N; and

    A and B, or the heterocyclic ring formed thereby, can be optionally independently substituted with from one to six substituents R5 independently selected from F, Cl, Br, I, nitro, cyano, —

    CF3, —

    NR7R8, —

    NR7C(═

    O)R8, —

    NR7C(═

    O)OR8, —

    NR7C(═

    O)NR8R9, —

    NR7S(═

    O)2R8, —

    NR7S(═

    O)2NR8R9, —

    OR7, —

    OC(═

    O)R7, —

    OC(═

    O)OR7, —

    C(═

    O)OR7, —

    C(═

    O)R7, —

    C(═

    O)NR7R8, —

    OC(═

    O)NR7R8, —

    OC(═

    O)SR7, —

    SR7, —

    S(═

    O)R7, —

    S(═

    O)2R7, —

    S(═

    O)2NR7R8, and R7;

    R3 is —

    C(═

    O)NR9

    , —

    C(═

    O)O—

    , —

    C(═

    O)(CR10R11)n

    , or —

    (CR10R11)n

    ;

    R4 is a straight chain or a branched (C1-C8)alkyl, a straight chain or a branched (C2-C8)alkenyl, a straight chain or branched (C2-C8 alkynyl), (C3-C8)cycloalkyl, (C4-C8)cycloalkenyl, (3-8 membered) heterocycloalkyl, (C5-C11)bicycloalkyl, (C7-C11)bicycloalkenyl, (5-11 membered) heterobicycloalkyl, (C6-C14)aryl, or (5-14 membered) heteroaryl; and

    wherein R4 is optionally substituted with from one to three substituents R6 independently selected from F, Cl, Br, I, nitro, cyano, —

    CF3, —

    NR7R8, —

    NR7C(═

    O)R8, —

    NR7C(═

    O)OR8, —

    NR7C(═

    O)NR8R9, —

    NR7S(═

    O)2R8,—

    NR7S(═

    O)2NR8R9, —

    OR7, —

    OC(═

    O)R7, —

    OC(═

    O)OR7, —

    C(═

    O)OR7, —

    C(═

    O)R7, —

    C(═

    O)NR7R8, —

    OC(═

    O)NR7R8, —

    OC(═

    O)SR7, —

    SR7, —

    S(═

    O)R7, —

    S(═

    O)2R7, —

    S(═

    O)2NR7R8, or R7;

    each R7, R8, and R9 is independently selected from H, straight chain or branched (C1-C8)alkyl, straight chain or branched (C2-C8)alkenyl, straight chain or branched (C2-C8 alkynyl), (C3-C8)cycloalkyl, (C4-C8)cycloalkenyl, (3-8 membered) heterocycloalkyl, (C5-C11)bicycloalkyl, (C7-C11)bicycloalkenyl, (5-11 membered) heterobicycloalkyl, (C6-C14)aryl, and (5-14 membered) heteroaryl, wherein R7, R8, and R9 are each independently optionally substituted with from one to six substituents independently selected from F, Cl, Br, I, NO2, —

    CN, —

    CF3, —

    NR10R11, —

    NR10C(═

    O)R11, —

    NR10C(═

    O)OR11, —

    NR10C(═

    O)NR11R12, —

    NR10S(═

    O)2R11, —

    NR10S(═

    O)2NR11R12, —

    OR10, OC(═

    O)R10, —

    OC(═

    O)OR10, —

    OC(═

    O)NR10R11, —

    OC(═

    O)SR10, —

    SR10, —

    S(═

    O)R10, —

    S(═

    O)2R10, —

    S(═

    O)2NR10R11, —

    C(═

    O)R10, —

    C(═

    O)OR10, —

    C(═

    O)NR10R11, and R10;

    or, when R7 and R8 are as in NR7R8, they may instead optionally be connected to form with the nitrogen of NR7R8 to which they are attached a heterocycloalkyl moiety of from three to seven ring members, said heterocycloalkyl moiety optionally comprising one or two further heteroatoms independently selected from N, O, and S;

    each R10, R11, and R12 is independently selected from H, straight chain or branched (C1-C8)alkyl, straight chain or branched (C2-C8)alkenyl, straight chain or branched (C2-C8 alkynyl), (C3-C8)cycloalkyl, (C4-C8)cycloalkenyl, (3-8 membered) heterocycloalkyl, (C5-C11)bicycloalkyl, (C7-C11)bicycloalkenyl, (5-11 membered) heterobicycloalkyl, (C6-C14)aryl, and (5-14 membered) heteroaryl, wherein R10, R11, and R12 are each independently optionally substituted with from one to six substituents independently selected from F, Cl, Br, I, NO2, —

    CN, —

    CF3, —

    NR13R14, —

    NR13C(═

    O)R14, —

    NR13C(═

    O)OR14, —

    NR13C(═

    O)NR14R15, —

    NR13S(═

    O)2R14, —

    NR13S(═

    O)2NR14R15, —

    OR13, —

    OC(═

    O)R13, —

    OC(═

    O)OR13, —

    OC(═

    O)NR13R14, —

    OC(═

    O)SR13, —

    SR13, —

    S(═

    O)R13, —

    S(═

    O)2R13, —

    S(═

    O)2NR13R14, —

    C(═

    O)R13, —

    C(═

    O)OR13, —

    C(═

    O)NR13R14, and R13;

    each R13, R14, and R15 is independently selected from H, straight chain or branched (C1-C8)alkyl, straight chain or branched (C2-C8)alkenyl, straight chain or branched (C2-C8 alkynyl), (C3-C8)cycloalkyl, (C4-C8)cycloalkenyl, (3-8 membered) heterocycloalkyl, (C5-C11)bicycloalkyl, (C7-C11)bicycloalkenyl, (5-11 membered) heterobicycloalkyl, (C6-C14)aryl, and (5-14 membered) heteroaryl, wherein R13, R14, and R15 are each independently optionally substituted with from one to six substituents independently selected from F, Cl, Br, I, NO2, —

    CN, —

    CF3, —

    NR16R17, —

    NR16C(═

    O)R17, —

    NR16C(═

    O)OR17, —

    NR16C(═

    O)NR17R18, —

    NR16S(═

    O)2R17, —

    NR16S(═

    O)2NR17R18, —

    OR16, —

    OC(═

    O)R16, —

    OC(═

    O)OR16, —

    OC(═

    O)NR16R17, —

    OC(═

    O)SR16, —

    SR16, —

    S(═

    O)R16, —

    S(═

    O)2R16, —

    S(═

    O)2NR16R17, —

    C(═

    O)R16, —

    C(═

    O)OR16, —

    C(═

    O)NR16R17, and R16;

    each R16, R17, and R18 is independently selected from H, straight chain or branched (C1-C8)alkyl, straight chain or branched (C2-C8)alkenyl, straight chain or branched (C2-C8 alkynyl), (C3-C8)cycloalkyl, (C4-C8)cycloalkenyl, (3-8 membered) heterocycloalkyl, (C5-C11)bicycloalkyl, (C7-C11)bicycloalkenyl, (5-11 membered) heterobicycloalkyl, (C6-C14)aryl, and (5-14 membered) heteroaryl;

    n is 0, 1, 2, or 3;

    wherein R10 and R11 in —

    C(═

    O)(CR10R11)n— and



    (CR10R11)n

    are for each iteration of n defined independently as recited above;

    or a pharmaceutically acceptable salt thereof.

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