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Aza-bicycles which modulate the inhibition of cell adhesion

  • US 6,608,084 B1
  • Filed: 10/17/2001
  • Issued: 08/19/2003
  • Est. Priority Date: 08/26/1998
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound of general formula (I):

  • embedded imagewherein;

    R1 represents R3

    L3

    Ar1

    L4

    Z3

    ;

    R2 represents hydrogen, halogen, C1-4alkyl or C1-4alkoxy;

    R3 represents alkyl, alkenyl allynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, cycloalkenyl, cycloalkenylalkyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, heterocycloalkyl or heterocycloalylalkyl;

    R5 represents hydrogen or C1-4alkyl;

    R7 and R7a are each independently hydrogen or C1-4alkyl;

    R8 represents hydrogen, alkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl or heterocycloalkylalkyl;

    R9 represents alkyl, aryl, cycloalkyl, heteroaryl or heterocycloalkyl, or alkyl substituted by aryl, carboxy, cycloalkyl, heteroaryl, heterocycloallyl, —

    S(O)mR3, —

    C(═

    O)—

    NY4Y5 or —

    NY4Y5;

    R10 represents hydrogen, R3 or alkyl substituted with alkoxy, cycloalkyl, hydroxy, mercapto, alkylthio or —

    NY4Y5;

    R14 represents alkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, hetetoarylalkyl, heterocycloalkyl or heterocycloalkylalkyl;

    A1 represents a methylene or ethylene linkage;

    Ar1 represents arylene;

    L1 represents;

    an allylene linkage optionally substituted by (a) carboxy, hydroxy, mercapto, R3, —

    N(R8)—

    C(═

    O)—

    R9, —

    N(R8)—

    C(═

    O)—

    OR9, —

    N(R8)—

    SO2

    R9 or —

    NY4Y5, or by (b) alkyl substituted by carboxy, hydroxy, mercapto, S(O)mR9, —

    C(═

    O)—

    NY4Y5 or —

    NY4Y5;

    L3 represents an —

    NR5

    C(═

    Z)—

    NR5

    linkage;

    L4 represents an alkylene chain;

    Y1 and Y2 are independently hydrogen, alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl or heteroarylalkyl;

    or the group —

    NY1Y2 may form a cyclic amine;

    Y4 and Y5 are independently hydrogen, alkenyl, alkyl, alkynyl, aryl, cycloalkenyl, cycloalkyl, heteroaryl, heterocycloalkyl, or alkyl substituted by alkoxy, aryl, cyano, cycloalkyl, heteroaryl, heterocycloalkyl, hydroxy, oxo, —

    NY1Y2, or one or more —

    CO2 R8 or —

    C(═

    O)—

    NY1Y2 groups;

    or the group —

    NY4Y5 may form a 5- to 7-membered cyclic amine which (i) may be optionally substituted with one or more substituents selected from alkoxy, carboxamido, carboxy, hydroxy, oxo, or a 5-, 6- or 7-membered cyclic acetal derivative thereof, or R10;

    (ii) may also contain a after heteroatom selected from O, S, SO2, or NY6; and

    (iii) may also be fused to additional aryl, heteroaryl, heterocycloalkyl or cycloalkyl rings to form a bicyclic or tricyclic ring system;

    Y6 represents hydrogen, alkyl, aryl, arylalkyl, —

    C(═

    O)—

    R14, —

    C(═

    O)OR14 or SO2R14;

    Z is an oxygen or sulphur atom;

    Z1 is C(R7)(R7a);

    Z3 is C(═

    O) or OC(═

    O);

    m is an integer 1 or 2; and

    Y is carboxy;

    and their ester prodrugs; and

    phamaceutically acceptable salts and solvates of such compounds and their ester prodrugs.

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