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US 8,026,262 B2Granted
Chemical compounds
AssigneeGlaxoSmithKline LLC
InventorsPhilip Stewart Turnbull, Rodolfo Cadilla, Andrew Larkin, Huiquiang Zhou, Eugene L. Stewart, Katherine Stetson, Darryl Lynn McDougald, Amarjit Sab Randhawa, John A. Ray
Life of this patent
Estimating the term…
Abstract
This invention relates to non-steroidal compounds that are modulators of androgen receptor, and also to the methods for the making and use of such compounds.
Claims20
A compound of formula (I)
- or a salt thereof, wherein
- X and Y are each independently C or N;
- X and Y are not both N;
- R1 is CN, halogen, C1-6alkoxy, or nitro;
- R2 is H, C1-6alkyl, C1-6haloalkyl, or CN;
- R3 is H, halogen, C1-6alkyl, C2-6alkenyl, C1-6haloalkyl, —C(O)R6, —CH2OH, or (CH2)qRx;
- Rx is —C3-6cycloalkyl, —C(O)OCH3, —C(O)OR7, or —CN;
- q is 0, 1, 2, or 3;
- R4 is (R8)(R9);
- R5 is H, C1-6alkyl, or halogen;
- R6 is H, C1-6alkyl, or NH2;
- R7 is C1-6alkyl;
- R8 is C1-6alkylene;
- R9 is oxadiazolyl, wherein said oxadiazolyl is optionally substituted with one or more substituents independently selected from Ra and Rb;
- wherein
- Ra is CN, —C(O)R6, —NR12R13, C1-6alkyl, C3-6cycloalkyl, C1-3haloalkyl, halogen, or heterocyclyl, wherein said heterocyclyl is optionally substituted with one or more substituents independently selected from halogen, CN, C1-6alkyl, C1-3haloalkyl, —SCH3, and —S(O)2CH3;
- Rb is phenyl optionally substituted with one or more substitutents independently selected from —OH, halogen, C1-6alkyl, C1-3haloalkyl, C1-3haloalkoxy, CN, nitro, C1-3alkoxy, C3-6cycloalkyl, heterocyclyl, —C(O)OCH3, —SCH3, —C(O)OH, —C(O)NR12R13, —S(O)2CH3, and —C(O)CH3;
- R10 is —OC1-6alkyl, —NH2, —NHCH2CH3, or —N(CH3)2;
- R11 is C1-6alkyl, C1-6alkoxyC1-6alkylene, or H;
- or
- R11 is heterocyclyl or phenyl, wherein said heterocyclyl or phenyl is optionally substituted with one or more substituents independently selected from C1-3alkyl, C1-3alkoxy, halogen, CN, —SO2CH3, —NHC(O)CH3, and C1-3haloalkyl;
- R12 and R13 are each independently selected from H and C1-6alkyl;
- m is 0 or 1;
- p is 0 or 1;
- R1 and R2 are not both H;
- when R4 is H, R3 is not H;
- when Y is N, m is 0;
- and
- when X is N, p is 0.
26 more elements
Dependencies are inferred from the claim text.