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Water soluble azoles as broad-spectrum antifungals

  • US 6,384,030 B1
  • Filed: 11/09/2000
  • Issued: 05/07/2002
  • Est. Priority Date: 05/14/1998
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound of formula embedded imagea N-oxide form, a pharmaceutically acceptable addition salt or a stereochemically isomeric form thereof, whereinL represents a radical of formula embedded image

  • wherein each Alk independently represents C1-6 alkanediyl optionally substituted with hydroxy or C1-4alkyloxy;

    each n independently is 1, 2 or 3;

    Y represents O, S or NR2;

    each R1 independently represents hydrogen, aryl, Het1, or C1-6alkyl optionally substituted with one, two or three substituents each independently selected from halo, hydroxy, mercapto, C1-4alkyloxy, C1-4alkylthio, aryloxy, arylthio, arylC1-4alkyloxy, arylC1-4alkylthio, cyano, amino, mono- or di(C1-4alkyl)amino, mono- or di(aryl)amino, mono- or di(arylC1-4alkyl)amino, C1-4alkyloxycarbonylamino, benzyloxycarbonylamino, aminocarbonyl, carboxyl, C1-4alkyloxycarbonyl, guanidinyl, aryl or Het2;

    each R2 independently represents hydrogen or C1-6alkyl;

    or in case R1 and R2 are attached to the same nitrogen atom, they may be taken together to form a heterocyclic radical selected from morpholinyl, pyrrolidinyl, piperidinyl, homopiperidinyl or piperazinyl;

    said heterocyclic radical may optionally be substituted with C1-4alkyl, aryl, Het2, arylC1-4alkyl, Het2C1-4alkyl, hydroxyC1-4alkyl, amino, mono- or di(C1-4alkyl)amino, aminoC1-4alkyl, mono- or di(C1-4alkyl)aminoC1-4alkyl, carboxyl, aminocarbonyl, C1-4alkyloxycarbonyl, C1-4alkyloxycarbonylamino or mono- or di(C1-4alkyl)aminocarbonyl;

    or they may be taken together to form an azido radical;

    each R3 independently represents hydrogen, hydroxy or C1-4alkyloxy;

    aryl represents phenyl, naphthalenyl, 1,2,3,4-tetrahydro-naphthalenyl, indenyl or indanyl;

    each of said aryl groups may optionally be substituted with one or more substituents selected from halo, C1-4alkyl, hydroxy, C1-4alkyloxy, nitro, amino, trifluoromethyl, hydroxyC1-4alkyl, C1-4alkyloxyC1-4alkyl, aminoC1-4alkyl, mono- or di(C1-4alkyl)aminoC1-4alkyl;

    Het1 represents a monocyclic or bicyclic heterocyclic radical;

    said monocyclic heterocyclic radical being selected from the group pyridinyl, piperidinyl, homopiperidinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, triazolyl, pyranyl, tetrahydropyranyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, thiazolyl, thiazolidinyl, isothiazolyl, oxazolyl, oxazolidinyl, isoxazolyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, furanyl, tetrahydrofuranyl, thienyl, thiolanyl, dioxolanyl;

    said bicyclic heterocyclic radical being selected from the group quinolinyl, 1,2,3,4-tetrahydro-quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phtalazinyl, cinnolinyl, chromanyl, thiochromanyl, 2H-chromenyl, 1,4-benzodioxanyl, indolyl, isoindolyl, indolinyl, indazolyl, purinyl, pyrrolopyridinyl, furanopyridinyl, thienopyridinyl, benzothiazolyl, benzoxazolyl, benzisothiazolyl, benzisoxazolyl, benzimidazolyl, benzofuranyl, benzothienyl;

    whereby each of said mono- or bicyclic heterocycle may optionally be substituted with one or where possible more substituents selected from halo, C1-4alkyl, hydroxy, C1-4alkyloxy, nitro, amino, trifluoromethyl, hydroxyC1-4alkyl, C1-4alkyloxy-C1-4alkyl, aminoC1-4alkyl, mono- or di(C1-4alkyl)aminoC1-4alkyl, aryl or arylC1-4alkyl;

    Het2 is the same as Het1 and may also be a monocyclic heterocycle selected from piperazinyl, homopiperazinyl, 1,4-dioxanyl, morpholinyl, thiomorpholinyl;

    whereby each of said monocyclic heterocycle may optionally be substituted with one or where possible more substituents selected from halo, C1-4alkyl, hydroxy, C1-4alkyloxy, nitro, amino, trifluoromethyl, hydroxyC1-4alkyl, C1-4alkyloxyC1-4alkyl, aminoC1-4alkyl, mono- or di-(C1-4alkyl)aminoC1-4alkyl, aryl or arylC1-4alkyl;

    R6 represents hydrogen or C1-4alkyl;

    R7 represents hydrogen or C1-4alkyl;

    or R6 and R7 taken together form a bivalent radical of formula —

    R6

    R7

    wherein —

    R6

    R7

    is;

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