US 7,550,598 B2
Kinase inhibitors
Sheldon X. Cao, San Diego, Calif. (US); Anthony R. Gangloff, San Diego, Calif. (US); Bheema R. Paraselli, San Diego, Calif. (US); Jeffrey A. Stafford, San Diego, Calif. (US); and Hasanthi P. Wijesekera, San Diego, Calif. (US)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (Japan)
Filed on Aug. 18, 2005, as Appl. No. 11/208,437.
Claims priority of provisional application 60/602902, filed on Aug. 18, 2004.
Prior Publication US 2006/0041137 A1, Feb. 23, 2006
Int. Cl. C07D 215/38 (2006.01); A61K 38/40 (2006.01)
U.S. Cl. 546—167  [546/153; 514/312; 514/314] 47 Claims
 
1. A compound consisting of the formula:

OG Complex Work Unit Drawing
wherein:
R1 is hydrogen;
R2 is hydrogen or (C1-6)alkyl;
R3 is selected from the group consisting of hydrogen, (C1-12)alkyl, alkoxy, thio, hydroxy, (C3-12)cycloalkyl, hetero(C2-12)cycloalkyl, hetero(C2-12)cycloalkoxy, (C9-12)bicycloaryl, hetero(C4-12)bicycloaryl, aryl, heteroaryl, heteroaryloxy, aryloxy, amino, carbonyl, imino, sulfonyl, sulfinyl, halo, cyano, nitro, trifluoromethoxy, and aryl(C1-12)alkyl, each unsubstituted or substituted, with the proviso that R3 is not hetero(C2-12)cycloalkyl, hetero(C4-12)bicycloaryl, or heteroaryl when Q is CO;
Q is selected from the group consisting of CO and CS;
R5 and R6 are each independently selected from the group consisting of hydrogen, halo, halo(C1-10)alkyl, amino, nitro, cyano, thio, sulfonamide, (C1-10)alkyl, (C3-12)cycloalkyl, hetero(C2-12)cycloalkyl, aryl(C1-10)alkyl, heteroaryl(C1-5)alkyl, (C9-12)bicycloaryl, hetero(C4-12)bicycloaryl, carbonyl(C1-3)alkyl, thiocarbonyl(C1-3)alkyl, sulfonyl(C1-3)alkyl, sulfinyl(C1-3)alkyl, imino(C1-3)alkyl, (C1-10)alkylamino, amino (C1-10)alkyl, aryl, heteroaryl, hydroxy, alkoxy, aryloxy, heteroaryloxy, carbonyl, imino, sulfonyl, and sulfinyl, each unsubstituted or substituted, or R5 and R6 are taken together to form an unsubstituted or substituted ring; and
R7, R8, R9, and R10 are each independently selected from the group consisting of hydrogen, halo, halo(C1-10)alkyl, amino, nitro, cyano, thio, sulfonamide, (C1-10)alkyl, (C3-12)cycloalkyl, hetero(C2-12)cycloalkyl, aryl(C1-10)alkyl, heteroaryl(C1-5)alkyl, (C9-12)bicycloaryl, hetero(C4-12)bicycloaryl, carbonyl(C1-3)alkyl, thiocarbonyl(C1-3)alkyl, sulfonyl(C1-3)alkyl, sulfinyl(C1-3)alkyl, imino(C1-3)alkyl, aryl, heteroaryl, hydroxy, alkoxy, aryloxy, heteroaryloxy, carbonyl group, imino group, sulfonyl group and sulfinyl group, each unsubstituted or substituted, or R6 and R7, R7 and R8, R8 and R9, or R9 and R10 are taken together to form an unsubstituted or substituted ring.