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Sulfonamides and derivatives thereof that modulate the activity of endothelin

  • US 6,686,382 B2
  • Filed: 12/29/2000
  • Issued: 02/03/2004
  • Est. Priority Date: 12/31/1999
  • Status: Expired due to Fees
First Claim
Patent Images

1. A compound that has formula IV:

  • embedded imageor pharmaceutically acceptable derivatives thereof, wherein;

    X is S or —

    C(R3)═

    (C(R4)—

    ;

    R1 is lower alkyl;

    R2 is lower alkyl;

    R3 and R4 are independently selected from among hydrogen, halo, cyano, cyanoalkyl, C(O)R41, alkyl, alkenyl, cycloalkyl and aryl, or together form alkylene or alkenylene, where R41 is alkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, cycloalkyl, alkylamino, dialkylamino, arylamino, diarylamino, alkylsulfonylamino, arylsulfonylamino, alkylsulfonylalkylamino, alkylsulfonylarylamino, arylsulfonylalkylamino or arylsulfonylarylamino;

    R5 is lower alkyl or —

    (CH2)xC(O)(CH2)yCH3;

    R6 is lower alkyl, —

    (CH2)xC(O)(CH2)yCH3, or heteroaryl;

    R7 is hydrogen, hydroxy, alkoxy, lower alkyl, S(O)2NHR50 or OS(O)2NR38R39;

    R38 and R39 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, haloalkyl, alkylaryl, heterocyclyl, arylalkyl, arylalkoxy, alkoxy, aryloxy, cycloalkyl, cycloalkenyl and cycloalkynyl;

    x and y are each independently 0 to 14;

    R50 is hydrogen, lower alkyl, lower alkoxy or heteroaryl;

    Y and R8 are selected from (i) or (ii) as follows;

    (i) Y is O; and

    R8 is CONR38R39, CN, heteroaryl, alkylsulfonyl, halide, pseudohalide, hydroxyalkyl, C(O)(CH2)xS(O)2(CH2)yCH3 or C(═

    N—

    OR38)(CH2)yCH3;

    or (ii) Y and R8 together with the atoms to which they are attached, form a 3 to 16 membered unsubstituted or substituted cyclic or heterocyclic ring;

    R9 is H;

    Y1 and Y2 are each independently carbon;

    a is 1;

    b is 1; and

    W is NH.

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