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Substituted heteroarylalkanoic acids

  • US 20030166668A1
  • Filed: 11/14/2002
  • Published: 09/04/2003
  • Est. Priority Date: 11/15/2001
  • Status: Active Grant
First Claim
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1. A compound of the formula D-A-C(O)R′

  • or a pharmaceutically acceptable salt thereof wherein D is a heteroaryl group selected from the group consisting of where Y is -Z-Ar where Z is a bond, O, S, C(O)NH, or C1-C6 alkylene optionally substituted with C1-C2 alkyl; and

    Ar represents an aryl or aryl(C1-C6)alkyl group, where the aryl portion is optionally substituted with up to 5 groups independently selected from (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2 wherein each R7 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy; and

    (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR17, SR17, S(O)R17, S(O)2R17 and N(R17)2 wherein each R17 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;

    a heteroaryl or heteroaryl(C1-C6)alkyl group, where the heteroaryl portion is optionally substituted by one, two or three groups independently selected from (1) halogen, (C1-C6)alkyl, hydroxy, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6) alkanoyl, (C1-C6) alkylthio, (C1-C6)haloalkylthio, OR27, SR27, S(O)R27, S(O)2R27 and N(R27)2 wherein each R27 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy; and

    (2) phenyl, pyridyl, furyl, and thienyl, each of which is optionally substituted with one, two, or three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR37, SR37, S (O)R37, S(O)2R37 and N(R37)2 wherein each R37 is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 haloalkoxy;

    R3 is hydrogen, halogen, hydroxy, (C1-C6)alkyl, (C1-C6)haloalkyl, amino, (C1-C6)alkylamino, di(C1-C6)alkylamino, aryl, —

    SR15 or —

    OR1s, where R15 is (C1-C6)alkyl, aryl, or aryl(C1-C6)alkyl where each aryl is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O) R7, S(O)2R7 and N (R7)2, R4 is hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkanoyl, or benzoyl where the phenyl portion is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N (R7)2;

    R5 is hydrogen, halogen, hydroxy, (C1-C6)alkoxy, (C1-C6) alkyl, halo(C1-C6)alkyl, hydroxy, amino, mono- or di(C1-C6)alkylamino, or aryl where aryl is optionally substituted with up to three groups independently selected from halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2;

    R6 is hydrogen, (C1-C6)alkyl, oxo, (C3-C7)cycloalkyl, (C3-C7)cycloalkyl (C1-C6)alkyl or aryl (C1-C6)alkyl where the aryl portion is optionally mono-, di-, or trisubstituted with halogen, (C1-C6)alkyl, hydroxy, halogen, (C1-C6)haloalkyl, (C2-C6)haloacetyl, cyano, nitro, (C1-C6)alkanoyl, (C1-C6)alkylthio, (C1-C6)haloalkylthio, OR7, SR7, S(O)R7, S(O)2R7 and N(R7)2;

    A is a C1-C4 alkylene group optionally substituted with C1-C2 alkyl or mono- or disubstituted with halogen; and

    R′

    is hydroxy, benzyloxy, di(C1-C6)alkylaminoethyloxy, acetoxymethyl, pivaloyloxymethyl, phthalidoyl, ethoxycarbonyloxyethyl, 5-methyl-2-oxo-1,3-dioxol-4-yl methyl, or (C1-C6)alkoxy optionally substituted by N-morpholino or di(C1-C6)alkylamino.

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