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Substituted pyridinones

  • US 7,067,540 B2
  • Filed: 02/14/2003
  • Issued: 06/27/2006
  • Est. Priority Date: 02/14/2002
  • Status: Active Grant
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Assignments
First Claim
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1. A compound of the formula:

  • embedded imageor a pharmaceutically acceptable salt thereof, whereinR1 is halogen substituted with 1, 2, 3, 4, or 5 groups that are independently halogen, —

    (C1-C6)alkyl-N(R)—

    CO2R30, haloalkyl, heteroaryl, heteroarylalkyl, —

    NR6R7, R6R7N—

    (C1-C6 alkyl)-, —

    C(O)NR6R7, —

    (C1-C4)alkyl-C(O)NR6R7, —

    (C1-C4 alkyl)-NRC(O)NR16R17, haloalkoxy, alkyl, CN, hydroxyalkyl, dihydroxyalkyl, alkoxy, alkoxycarbonyl, phenyl, —

    SO2-phenyl wherein the phenyl and —

    SO2-phenyl groups are optionally substituted with 1, 2, or 3 groups that are independently halogen or NO2, or —

    OC(O)NR6R7, wherein R16 and R17 are independently H or C1-C6 alkyl;

    or R16, R17 and the nitrogen to which they are attached form a morpholinyl ring;

    R6 and R7 are independently at each occurrence H, alkyl, hydroxyalkyl, dihydroxyalkyl, alkoxy, alkanoyl, arylalkyl, arylalkoxy, alkoxycarbonyl, —

    SO2-alkyl, OH, alkoxy, alkoxyalkyl, arylalkoxycarbonyl, —

    (C1-C4)alkyl-CO2-alkyl, heteroarylalkyl, or arylalkanoyl, wherein each is unsubstituted or substituted with 1, 2, or 3 groups that are independently, halogen, OH, SH, heterocycloalkyl, heterocycloalkylalkyl, C3-C7 cycloalkyl, alkoxy, NH2, NH(alkyl), N(alkyl)(alkyl), —

    O-alkanoyl, alkyl, haloalkyl, carboxaldehyde, or haloalkoxy;

    or R6, R7, and the nitrogen to which they are attached form a morpholinyl, pyrrolidinyl, thiomorpholinyl, thiomorpholinyl S-oxide, thiomorpholinyl S,S-dioxide, piperidinyl, pyrrolidinyl, or piperazinyl ring which is optionally substituted with 1 or 2 groups that are independently C1-C4 alkyl, alkoxycarbonyl, C1-C4 alkoxy, hydroxyl, hydroxyalkyl, dihydroxyalkyl, or halogen;

    R30 is C1-C6 alkyl optionally substituted with 1 or 2 groups that are independently OH, SH, halogen, amino, monoalkylamino, dialkylamino or C3-C6 cycloalkyl;

    R3 is H, halogen, alkoxycarbonyl, arylalkoxycarbonyl, aryloxycarbonyl, arylalkyl, —

    OC(O)NH(CH2)naryl, arylalkoxy, —

    OC(O)N(alkyl)(CH2)naryl, aryloxy, arylthio, thioalkoxy, arylthioalkoxy, alkenyl, —

    NR6R7, NR6R7—

    (C1-C6)alkyl, or alkyl, wherein the aryl portion of arylalkoxycarbonyl, aryloxycarbonyl, arylalkyl, —

    OC(O)NH(CH2)naryl, arylalkoxy, —

    OC(O)N(alkyl)(CH2)naryl, and arylthioalkoxy, is unsubstituted or substituted with 1, 2, 3, 4, or 5 groups that are independently, halogen, alkoxy, alkyl, haloalkyl, or haloalkoxy, wherein n is 0, 1, 2, 3, 4, 5, or 6;

    or R4 is alkyl unsubstituted or substituted with one or two groups that are independently CO2R, —

    CO2—

    (C1-C6)alkyl, —

    C(O)NR6R7, —

    C(O)R6, —

    N(R30)C(O)NR16R17, —

    N(R30)C(O)—

    (C1-C6)alkoxy, or —

    NR6R7, arylalkoxy, arylalkyl, heteroaryl, heteroarylalkyl, hydroxyalkyl, dihydroxyalkyl, haloalkyl, R6R7N—

    (C1-C6 alkyl)-, —

    NR6R7, alkoxy, carboxaldehyde, —

    C(O)NR6R7, CO2R, alkoxyalkyl, or alkoxyalkoxy, wherein the heteroaryl or aryl portions of is the above are unsubstituted or substituted with 1, 2, 3, 4, or 5 groups that are independently halogen, hydroxy, alkoxy, alkyl, —

    CO2—

    (C1-C6)alkyl, —

    CONR6R7, —

    NR6R7, R6R7N—

    (C1-C6)alkyl-, nitro, haloalkyl, or haloalkoxy; and

    R5 is H, aryl, arylalkyl, arylthioalkyl, alkyl optionally substituted with 1, 2, or 3 groups that are independently arylalkoxycarbonyl, —

    NR8R9, halogen, —

    C(O)NR8R9, alkoxycarbonyl, C3-C7 cycloalkyl, or alkanoyl, alkoxy, alkoxyalkyl optionally substituted with one trimethylsilyl group, amino, alkoxycarbonyl, hydroxyalkyl, dihydroxyalkyl, alkynyl, —

    SO2-alkyl, alkoxy optionally substituted with one trimethylsilyl group, heterocycloalkylalkyl, cycloalkyl, cycloalkylalkyl, -alkyl-S-aryl, -alkyl-SO2-aryl, heteroarylalkyl, heterocycloalkyl, heteroaryl, or alkenyl optionally substituted with alkoxycarbonyl, wherein each of the above is unsubstituted or substituted with 1, 2, 3, 4, or 5 groups that are independently alkyl, halogen, alkoxy, hydroxyalkyl, dihydroxyalkyl, arylalkoxy, thioalkoxy, alkoxycarbonyl, arylalkoxycarbonyl, CO2R, CN, OH, hydroxyalkyl, dihydroxyalkyl, amidinooxime, —

    NR6R7, —

    NR8R9, R6R7N—

    (C1-C6 alkyl)-, carboxaldehyde, SO2 alkyl, —

    SO2H, —

    SO2NR6R7, alkanoyl wherein the alkyl portion is optionally substituted with OH, halogen or alkoxy, —

    C(O)NR6R7, —

    (C1-C4 alkyl)-C(O)NR6R7, amidino, haloalkyl, —

    (C1-C4 alkyl)-NR15C(O)NR16R17, —

    (C1-C4 alkyl)-NR15C(O)R18, —

    O—

    CH2—

    O, —

    O—

    CH2CH2—

    O—

    , or haloalkoxy;

    wherein R15 is H or C1-C6 alkyl; and

    R18 is C1-C6 alkyl optionally substituted with —

    O—

    (C2-C6 alkanoyl, C1-C6 hydroxyalkyl, C1-C6 dihydroxyalkyl, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl;

    amino C1-C6 alkyl, mono or dialkylamino C1-C6 alkyl.

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