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N, N-disubstituted amides that inhibit the binding of integrins to their receptors

  • US 6,194,448 B1
  • Filed: 10/14/1999
  • Issued: 02/27/2001
  • Est. Priority Date: 04/16/1998
  • Status: Expired due to Term
First Claim
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1. A compound of the structure whereinA is selected from the group consisting of —

  • O—

    , —

    S—

    , and —

    NR6

    ;

    E is selected from the group consisting of —

    CH2

    , —

    O—

    , —

    S—

    , and —

    NR7

    ;

    each J is independently selected from the group consisting of —

    O—

    , —

    S— and



    NR8

    ;

    T is selected from the group consisting of —

    C(O)— and



    (CH2)b

    wherein b is an integer of from 0 to 3;

    s and t are each independently integers of zero to three;

    L is selected from the group consisting of —

    O—

    , —

    NR9

    , —

    S—

    , and —

    (CH2)n

    wherein n is an integer of 0 or 1;

    M is selected from the group consisting of —

    C(R10)(R11)— and



    (CH2)u

    wherein u is an integer of from 0 to 3;

    X is selected from the group consisting of —

    CO2B, —

    PO3H2, —

    SO3H, —

    OPO3H2, —

    C(O)NHC(O)R12, —

    C(O)NHSO2R13, oxazolyl, tetrazolyl and hydrogen;

    B, R1, R2, R3, 0R4, R5, R6, R7, R8, R9, R10, R11, R12 and R13 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkynoxy, thioalkoxy, aliphatic acyl, —

    CF3, nitro, amino, cyano, —

    N(C1-C3 alkyl)—

    C(O)(C1-C3 alkyl), —

    C1-C3 alkylamino, alkenylamino, alkynylamino, di(C1-C3 alkyl)amino, —

    C(O)O—

    (C1-C3 alkyl), —

    C(O)NH—

    (C1-C3 alkyl), —

    CH═

    NOH, —

    PO3H2, —

    OPO3H2, —

    C(O)N(C1-C3 alkyl)2, haloalkyl, alkoxylcarbonyl, alkoxyalkoxy, carboxaldehyde, carboxamide, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, aroyl, aryloxy, arylamino, biaryl, thioaryl, heterocyclyl, heterocycloyl, alkylaryl, aralkenyl, aralkyl, alkylheterocyclyl, heterocyclylalkyl, sulfonyl, sulfonamido, carbamate, aryloxyalkyl, carboxyl and —

    C(O)NH(benzyl);

    wherein B, X, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 and R13 are unsubstituted or substituted with at least one electron donating or electron withdrawing group;

    and wherein R3 and R4 taken together may form a first ring;

    R5 and R9 taken together may form a second ring;

    R10 and R11 taken together may form a third ring;

    R1 and R2 taken together may form a fourth ring;

    and pharmaceutically acceptable salts thereof.

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