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US 7,560,586 B2Granted
Acid and ester compounds and methods of using the same
AssigneeSmithKline Beecham Corporation
InventorsScott K. Thompson, Lara S. Kallander, Chun Ma, Joseph Marino, Dennis Lee
Life of this patent
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Abstract
Disclosed is a compound of having the formula: pharmaceutically acceptable salts or solvates thereof and pharmaceutical compositions containing the same, wherein the structural variables are as defined herein. The compounds, salts and solvates of this invention are useful as LXR agonists.
Claims27
A compound of Formula I:
- wherein:
- Z is CH or CR3;
- wherein k is 0-4;
- p is 0-8;
- n is 2-8;
- q is 0 or 1;
- Q is C3-C8 cycloalkyl or phenyl;
- wherein said C3-C8 cycloalkyl, or phenyl are optionally unsubstituted or substituted with one or more groups independently selected from halo, cyano, nitro, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, —C0-C6 alkyl-CO2R11, —C0-C6 alkyl-C(O)SR11, —C0-C6 alkyl-CONR12R13, —C0-C6 alkyl-COR14, —C0-C6 alkyl-NR12R13, —C0-C6 alkyl-SR11, —C0-C6 alkyl-OR11, —C0-C6 alkyl-SO3H, —C0-C6 alkyl-SO2NR12R13, —C0-C6 alkyl-SO2R11, —C0-C6 alkyl-SOR14, —C0-C6 alkyl-OCOR14, —C0-C6 alkyl-OC(O)NR12R13, —C0-C6 alkyl-OC(O)OR14, —C0-C6 alkyl-NR12C(O)OR14, —C0-C6 alkyl-NR12C(O)NR12R13, and —C0-C6 alkyl-NR12COR14, where said C1-C6 alkyl is optionally unsubstituted or substituted by one or more halo substituents;
- W1 and W2 are each independently C3-C8 cycloalkyl or aryl;
- each R1 and R2 is independently selected from H, C1-C6 alkyl, —OH, —O—C1-C6 alkyl, —SH, and —S—C1-C6 alkyl;
- each R3 is the same or different and is independently selected from halo, cyano, nitro, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, —C0-C6 alkyl-Ar, —C0-C6 alkyl-C3-C7 cycloalkyl, —C0-C6 alkyl-CO2R11, —C0-C6 alkyl-C(O)SR11, —C0-C6 alkyl-CONR12R13, —C0-C6 alkyl-COR14, —C0-C6 alkyl-NR12R13, —C0-C6 alkyl-SR11, —C0-C6 alkyl-OR11, —C0-C6 alkyl-SO3H, —C0-C6 alkyl-SO2NR12R13, —C0-C6 alkyl-SO2R11, —C0-C6 alkyl-SOR14, —C0-C6 alkyl-OCOR14, —C0-C6 alkyl-OC(O)NR12R13, —C0-C6 alkyl-OC(O)OR14, —C0-C6 alkyl-NR12C(O)OR14, —C0-C6 alkyl-NR12C(O)NR12R13, and —C0-C6 alkyl-NR12COR14, wherein said C1-C6 alkyl is optionally unsubstituted or substituted by one or more halo substituents;
- each R4 and R5 is independently H or C1-C4 alkyl;
- R6 and R7 are each independently H or C1-C4 alkyl;
- R8 and R9 are each independently H or C1-C4 alkyl;
- R10 is H, C1-C8 alkyl, C3-C8 alkenyl, C3-C8 alkynyl, —C0-C6 alkyl-Ar, or —C0-C6 alkyl-C3-C7 cycloalkyl;
- R11 is H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, —C0-C6 alkyl-Ar, or —C0-C6 alkyl-C3-C7 cycloalkyl;
- each R12 and each R13 are independently selected from H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, —C0-C6 alkyl-Ar, and —C0-C6 alkyl-C3-C7 cycloalkyl;
- and
- R14 is C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, —C0-C6 alkyl-Ar, or —C0-C6 alkyl-C3-C7 cycloalkyl;
- provided that R10 is not H or methyl when p is 1 and R1 and R2 are each H, k is 0, n is 3 and each R4 and R5 are H, q is 1 and R8 and R9 are each H, Q is unsubstituted phenyl or 4-methoxyphenyl or 2-chloro-3-trifluoromethyl-phenyl, R6 and R7 are each H, W1 is unsubstituted phenyl and W2 is unsubstituted phenyl or unsubstituted cyclohexyl;
- or a pharmaceutically acceptable salt thereof.
18 more elements
A compound of Formula II:
- wherein:
- Z is CH;
- Q is phenyl;
- wherein said phenyl is optionally unsubstituted or substituted with one or more groups independently selected from halo, cyano, nitro, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, —C0-C4 alkyl-CO2R11, —C0-C6 alkyl-C(O)SR11, —C0-C4 alkyl-CONR12R13, —C0-C4 alkyl-COR14, —C0-C4 alkyl-NR12R13, —C0-C4 alkyl-SR11, —C0-C4 alkyl-OR11, —C0-C4 alkyl-SO3H, —C0-C4 alkyl-SO2NR12R13, —C0-C4 alkyl-SO2R11, —C0-C4 alkyl-SOR14, —C0-C4 alkyl-OCOR14, —C0-C4 alkyl-OC(O)NR12R13, —C0-C4 alkyl-OC(O)OR14, —C0-C4 alkyl-NR12C(O)OR14, —C0-C4 alkyl-NR12C(O)NR12R13, and —C0-C4 alkyl-NR12COR14, where said C1-C6 alkyl is optionally unsubstituted or substituted by one or more halo substituents,
- p is 0-4;
- k is 0, 1 or 2;
- n is 2-4;
- q is 0 or 1;
- W1 and W2 are each independently C3-C6 cycloalkyl or aryl;
- each R1 and R2 is independently selected from H, C1-C4 alkyl, —OH, —O—C1-C4 alkyl, —SH, and —S—C1-C4 alkyl;
- each R3 is the same or different and is independently selected from halo, cyano, C1-C6 alkyl, —C0-C4 alkyl-NR12R13, —C0-C4 alkyl-OR11, —C0-C4 alkyl-SO2NR12R13, and —C0-C4 alkyl-CO2H, wherein said C1-C6 alkyl is optionally unsubstituted or substituted by one or more halo substituents;
- each R4 and R5 is independently H or C1-C4 alkyl;
- R6 and R7 are each independently H or C1-C4 alkyl;
- R8 and R9 are each independently H or C1-C4 alkyl;
- R10 is H, C1-C6 alkyl, —C0-C4 alkyl-Ar, or —C0-C4 alkyl-C3-C6 cycloalkyl;
- R11 is H, C1-C6 alkyl, —C0-C4 alkyl-Ar, or —C0-C4 alkyl-C3-C7 cycloalkyl;
- each R12 and each R13 are independently selected from H, C1-C6 alkyl, —C0-C4 alkyl-Ar, and —C0-C4 alkyl-C3-C7 cycloalkyl;
- and
- R14 is C1-C6 alkyl, —C0-C4 alkyl-Ar, or —C0-C4 alkyl-C3-C7 cycloalkyl;
- provided that R10 is not H or methyl when p is 1 and R1 and R2 are each H, k is 0, n is 3 and each R4 and R5 are H, q is 1 and R8 and R9 are each H, Q is unsubstituted phenyl or 4-methoxyphenyl or 2-chloro-3-trifluoromethyl-phenyl, R6 and R7 are each H, W1 is unsubstituted phenyl and W2 is unsubstituted phenyl or unsubstituted cyclohexyl;
- or a pharmaceutically acceptable salt thereof.
18 more elements
Dependencies are inferred from the claim text.