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Plasminogen activator inhibitor antagonists

  • US 6,638,977 B1
  • Filed: 11/19/1999
  • Issued: 10/28/2003
  • Est. Priority Date: 11/19/1999
  • Status: Expired due to Fees
First Claim
Patent Images

1. A pharmaceutical composition, comprising a compound having the formula:

  • embedded imageor a pharmaceutically acceptable derivative thereof, in a pharmaceutically acceptable carrier, wherein;

    Z and Z′

    are each carbon;

    X′

    is (CH2)dO or (CH2)dS;

    d is an integer from 1 to 6;

    R1 is halide or pseudohalide;

    m is 2;

    R2, R3, n and p are selected from (i) or (ii) as follows;

    (i) R2 is alkyl, aryl, alkoxy, haloalkyl, haloalkoxy, halide or pseudohalide;

    n is an integer from 1 to 5;

    R3 is hydroxy or alkoxy;

    p is an integer from 0 to 3;

    or (ii) n and p are 1; and

    R2 and R3, together form, with the carbon to which each is attached, an aryl, aromatic ring, heteroaromatic ring, carbocyclic or heterocyclic ring, which is saturated or unsaturated, containing from about 3 to about 16 members;

    R4 and R5 are each independently selected from —

    SO3

    , —

    NO2, alkyl, hydroxy, alkoxy, halide or pseudohalide;

    q is an integer from 0 to 1;

    r is an integer from 0 to 2;

    X is H, C1-17alkyl-L-, C2-17alkenyl-L-, or C2-17alkynyl-L-;

    L is a direct link, amido, carboxy, carbonyl, carbamoyl, sulfonyl, carbamide, ureido, sulfonamide, hydrazinyl, hydrazide, semicarbazide, carbazate, thiocarbazate, isothiocarbazate or sulfonyl hydrazide;

    Y′

    is selected from a direct link, alkylene, a heterocyclylene group, —

    COO—

    , —

    S(O)2O—

    , —

    S(O)O—

    , —

    P(O)(OH)O—

    , —

    P(OH)O— and



    B(OH)O—

    ;

    Y is a direcalky link, C1-4alkyl(W)(carboxy), C2-4alkenyl(W)(carboxy), C2-4alkynyl(W)(carboxy), C1-4alkyl(W)(sulfo), C2-4alkenyl(W)(sulfo) or C2-4alkynyl(W)(sulfo);

    where W is H, amino or A-D-E-G, where A is C1-4alkylene, C2-4alkenylene or C2-4alkynylene;

    D is a direct link, amido, ureido, imino, azido, carbamoyl, thio or thionyl;

    E is a direct link, C1-3alkylene, arylene or heteroarylene; and

    G is H, amino, nitro, cyano, hydrazinyl, thio or sulfonamido;

    with the provisos that (i) if m, n or p are not 0, then q and r are 0;

    (ii) if q or r are not 0, then m, n and p are 0;

    (iii) if X is not H, then Y is a direct link;

    (iv) if Y is not a direct link, then Y′

    is a direct link;

    (v) if Y′

    is not a direct link, then Y is a direct link;

    (vi) if D is not a direct link, then G is H;

    (vii) if D is a single bond and G is not H, then E is a single bond; and

    (viii) if E is not a direct link or C1-3alkylene, then G is H.

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