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Thiadiazole derivatives useful for the treatment of diseases related to connective tissue degradation

  • US 5,847,148 A
  • Filed: 04/10/1997
  • Issued: 12/08/1998
  • Est. Priority Date: 04/10/1997
  • Status: Expired due to Fees
First Claim
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1. A compound of formula Ior pharmaceutical acceptable salts thereof wherein:

  • x isa) O, orb) S;

    R1 isa) H,b) C1-6 alkyl,c) --(CH2)i -aryl,d) --(CH2)j -cycloalkyl,e) --(C1-4 alkyl)--O--R4,f) --(C1-4 alkyl)--S--R4,f) --(CH2)j -Het,g) --C(═

    O)--O--R4,h) --C(═

    O)--NR5 R5, ori) --(CH2) --O--Si(R4)3 ;

    R2 isa) --O--R5, orb) --NR6 R7 ;

    R3 isa) H,b) C1-6 alkyl,c) --(CH2)i -aryl,d) --(CH2)j -cycloalkyl,e) --(C1-4 alkyl)--O--R4,f) --(C1-4 alkyl)--S--R4, org) --OR4 ;

    R4 isa) H,b) C1-6 alkyl, orc) --(CH2)i -aryl;

    R5 isa) H,b) C1-6 alkyl, orc) aryl;

    R6 and R7 may be the same or differentlya) H,b) C1-6 alkyl,c) C1-6 OR4,d) --(CH2)i -aryl,e) --(CH2)j -cycloalkyl,f) --(CH2)j -Het,g) --(CH2)--Q,h) --(CH2) --C(═

    O)--OR4,i) --(CH2)j --C(═

    O)--NR5 R5,j) 5-(((5-(dimethylamino)-1-naphthalenyl)sulfonyl)amino)pentyl, orR6 and R7 taken together with the linking N-atom to formk) azetidinyl,l) pyrrolidinyl,m) piperidinyl,n) morpholino,o) 4-thiomorpholinyl, or ##STR94## R8 is a) H,b) C1-6 alkyl,c) --(CH2)i -aryl,d) benzhydryl, ore) --(CH2)i -Het;

    aryl isphenyl, biphenyl, or naphthalene, optionally substituted with one to five of the following;

    a) C1-4 alkyl,b) --OR4,c) halogen,d) --NR5 R5,e) --C(═

    O)--NR5 R5,f) --NHC(═

    O)R4,g) --SO2 NR5 R5,h) --NHSO2 R5,i) --NO2,j) --CF3, ork) --O--Si(R4)3 ;

    Het isa 5-, 6-, 9-, or 10-membered heteroaromatic moiety having one or more atoms selected from the group consisting of N, O, and S;

    Q isa saturated 5-, or 6-membered heterocyclic moiety having 1-2 atoms selected from the group consisting of N, O, and S;

    i is 0, 1, 2, 3, or 4;

    j is 1, 2, 3, or 4;

    n is 0, or 1;

    with the following provisos;

    a) where R1 is isobutyl, R6 and R7 are other than methyl,b) where R1 is isobutyl, R5 is other than methyl.c) where X is O at least one of R1 and R3 is other than H, or C1-6 alkyld) where R1 and R3 is C1-6 alkyl, R5 is other than H or C1-6 alkyl, ande) where R1 and R3 is C1-6 alkyl, at least one of R6 and R7 is other than H or C16 alkyl.

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