Substituted pyrazole derivatives condensed with six-membered heterocyclic rings

  • US 6,743,798 B1
  • Filed: 04/11/2001
  • Issued: 06/01/2004
  • Est. Priority Date: 07/29/1998
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound of the formula (I) embedded imagein whichR1 represents pyrimidinyl group, which is optionally substituted up to 2 times by identical or different radicals from the group (i) consisting of hydrogen, amino, azido, formyl, mercaptyl, carboxyl, hydroxyl, straight-chain or branched acyl, alkoxy, alkylthio or alkoxycarbonyl having in each case up to 6 carbon atoms, nitro, cyano, halogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms which for its part may be substituted by hydroxyl, amino, azido, carboxyl, straight-chain or branched acyl, alkoxy, alkoxycarbonyl or acylamino having in each case up to 5 carbon atoms or by a radical of the formula —

  • OR4

    in which R4 represents straight-chain or branched acyl having up to 5 carbon atoms and/or is substituted by a radical of the formula embedded image



    S(O)c

    NR6R7

    in which a, b and b′

    are identical or different and each represents a number 0, 1, 2 or 3, R5 is hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, c is a number 1 or 2 and R6 and R7 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 10 carbon atoms which is optionally substituted by cycloalkyl having 3 to 8 carbon atoms or by aryl having 6 to 10 carbon atoms which for its part may be substituted by halogen, or represents aryl having 6 to 10 carbon atoms which is optionally substituted by halogen,  

    or represents cycloalkyl having 3 to 7 carbon atoms,  

    or R6 and R7 together with the nitrogen atom form a 5- to 7-membered saturated heterocycle which may optionally contain a further oxygen atom or a radical —

    NR8

    in which R8 represents hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms or a radical of the formula embedded image

    or benzyl or phenyl where the ring systems are optionally substituted by halogen, and which is substituted by at least one radical selected from the group (ii) consisting of imidazolyl, imidazolinyl, imidazolidinyl, morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, triazolyl, pyrrolyl, thiomorpholinyl, S-oxothiomorpholinyl, S,S-dioxothiomorpholinyl, thiazolyl, and thiadiazolyl, and which is optionally mono- or polysubstituted by a 5- or 6-membered ring which contains two oxygen atoms as ring members and forms a bicyclic unit or a spiro unit with the ring to which it is attached, and/or by hydroxyl, cyano, straight-chain or branched alkyl, acyl or alkoxycarbonyl having in each case up to 6 carbon atoms, where alkyl, acyl and alkoxycarbonyl may be substituted by hydroxyl, amino, halogen, carboxyl, straight-chain or branched acyl, alkoxy, alkoxycarbonyl or acylamino having in each case up to 5 carbon atoms, and an aryl ring having 6 to 10 carbon atoms which is substituted by straight-chain or branched alkyl having up to 4 carbon atoms, and (C2-C10)alkenyl, (C2-C10)alkinyl, (C7-C20)alkyl, which is optionally substituted by aryl, halogen, cyano, dialkylamino, cycloalkyl, alkylamine, hydroxyl, amino, azido, carboxyl, straight-chain or branched acyl, alkoxy, alkoxycarbonyl or acylamino having in each case up to 5 carbon atoms or by a radical of the formula —

    OR4

    in which R4 represents straight-chain or branched acyl having up to 5 carbon atoms and (C1-C6)alkyl which is substituted 1- to 3 times by aryl, halogen(s), cyano, dialkylamino, alkylamino or cycloalkyl and acyl, which is substituted by halogen, acyloxy, or arylthio, and —

    NO or radicals of the formulae —

    SO3H and —

    S(O)dR9,  

    in which d represents a number 1 or 2, R9 represents straight-chain or branched alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or thienyl, where the ring systems may optionally be substituted by halogen or by straight-chain or branched alkyl or alkoxy having in each case up to 4 carbon atoms, and a radical of the formula PO(OR10)(OR11)  

    in which R10 and R11 are identical or different and each represents hydrogen, straight-chain or branched alkyl having up to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, aryl having 6 to 10 carbon atoms or benzyl, and oxycycloalkyl having 3 to 8 ring members or radicals of the formulae —

    CON═

    C(NH2)2, —

    C═

    NH(NH2), —

    NH—

    C(═

    NH)NH2 or (CO)eNR12R13

    in which e represents a number 0 or 1, R12 and R13 are identical or different and each represents hydrogen, straight-chain or branched alkyl having up to 14 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, or aryl having 6 to 10 carbon atoms, where the abovementioned radicals may optionally be substituted by aryl having 6 to 10 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, hydroxyl, amino or straight-chain or branched alkoxy, acyl or alkoxycarbonyl having in each case up to 6 carbon atoms, and, in the case that e=1, R12 and R13, together with the nitrogen atom to which they are attached, may also form a morpholinyl, pyrrolidinyl, or piperidinyl group, which may optionally be substituted up to 3 times by hydroxyl, alkoxy or alkyl having in each case up to 8 carbon atoms, and, in the case that e=0, R12 and R13 may also represent straight-chain, branched or cyclic acyl having up to 14 carbon atoms, hydroxyalkyl, straight-chain or branched alkoxycarbonyl or acyloxyalkyl having in each case up to 6 carbon atoms, or a radical of the formula —

    SO2R14

    in which R14 represents straight-chain or branched alkyl having up to 4 carbon atoms, and/or R12 and R13 also represent radicals of the formulae embedded image

    in which R15-R16 and R18-R31 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, g represents a number 0, 1 or 2, and R17 represents phenyl, straight-chain or branched alkyl having up to 6 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, with the proviso that, if e=0, R12 and R13 do not simultaneously represent hydrogen, or R1 represents a purine radical which may optionally be substituted up to three times by halogen, azido, cyano, hydroxyl, amino, monoalkylamino having up to 5 carbon atoms, dialkylamino having in each case up to 5 carbon atoms, alkyl having up to 5 carbon atoms and/or alkoxy having up to 5 carbon atoms, R2 and R3, together with the double bond, form a fused pyridyl ring, which is optionally substituted up to three times by identical or different substituents from the group consisting of formyl, carboxyl, hydroxyl, mercaptyl, straight-chain or branched acyl, alkylthio or alkoxycarbonyl having in each case up to 6 carbon atoms, nitro, cyano, halogen or straight-chain or branched alkyl or alkoxy having in each case up to 6 carbon atoms which for its part may be substituted by hydroxyl, amino, carboxyl, straight-chain or branched acyl, alkoxy or alkoxycarbonyl having in each case up to 5 carbon atoms, and/or which is optionally substituted by a group of the formula —

    NR32R33

    in which R32 and R33 are identical or different and each represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, or R32 represents hydrogen and R33 represents acyl, and/or which is optionally substituted by phenyl which for its part may be substituted up to 2 times by identical or different substituents from the group consisting of halogen and straight-chain or branched alkyl or alkoxy having in each case up to 6 carbon atoms, and/or which is optionally substituted by a group of the formula —

    N═

    CH—

    NR34R35

    in which R34 and R35 are identical or different and each represents hydrogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms, A represents thienyl tetrahydropyranyl, tetrahydrofuranyl, phenyl, morpholinyl, pyrimidyl, pyrazinyl, pyridazinyl or pyridyl which are optionally substituted up to 3 times by identical or different substituents from the group consisting of amino, mercaptyl, hydroxyl, formyl, carboxyl, straight-chain or branched acyl, alkylthio, alkyloxyacyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, nitro, cyano, trifluoromethyl, azido, halogen, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms which for its part may be substituted by hydroxyl, carboxyl, straight-chain or branched acyl, alkoxy or alkoxycarbonyl having in each case up to 5 carbon atoms, and/or is substituted by a group of the formula —

    (CO)h

    NR36R37

    in which h represents a number 0 or 1, R36 and R37 are identical or different and each represents hydrogen, phenyl, benzyl or straight-chain or branched alkyl or acyl having in each case up to 5 carbon atoms, or a stereoisomeric form or salt thereof.

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