Certain chemical entities, compositions, and methods

A method of inhibiting KDR kinase activity in a subject, comprising administering to the subject a therapeutically effective amount of a compound of Formula I:

• or a pharmaceutically acceptable salt thereof, wherein:
• R1, R2, R3, R4, R5, R6, R7, R8, and R10 are independently hydrogen, cyano, halo, hydroxy, azido, nitro, carboxy, sulfinyl, sulfanyl, sulfonyl, alkoxy, cycloalkyloxy, aryloxy, heteroaryloxy, heterocycloalkyloxy, alkyl, alkenyl, aryl, heteroaryl, heterocycloalkyl, amino, acyl, alkoxycarbonyl, aminocarbonyl, aminosulfonyl, carbamimidoyl, or alkynyl;
• R9 is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;
• R11 is hydroxy, formyl, alkoxy, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —COR12, —CO2R12, —CONR12R13, —C(NR14)NR12R13, —C(NCN)NR12R13, or —SO2NR12R13;
• or
• R9 and R11 may be joined together with any intervening atoms to form a heterocycloalkyl ring;
• R12 is alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;
• R13 and R14 are independently hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;
• or
• R12 and R13 may be joined together with any intervening atoms to form a heterocycloalkyl ring;
• wherein:
• any of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, the heterocycloalkyl ring formed by R9 and R11, and the heterocycloalkyl ring formed by R12 and R13 may be substituted with one or more substituents independently selected from the group consisting of C1-C4 alkyl, aryl, heteroaryl, aryl-C1-C4 alkyl-, heteroaryl-C1-C4 alkyl-, C1-C4 haloalkyl, —OC1-C4 alkyl, —OC1-C4 alkylphenyl, —C1-C4 alkyl-OH, —OC1-C4 haloalkyl, halo, —OH, —NH2, —C1-C4 alkyl-NH2, —N(C1-C4 alkyl)(C1-C4 alkyl), —NH(C1-C4 alkyl), —N(C1-C4 alkyl)(C1-C4 alkylphenyl), —NH(C1-C4 alkylphenyl), cyano, nitro, oxo, —CO2H, —C(O)OC1-C4 alkyl, —CON(C1-C4 alkyl)(C1-C4 alkyl), —CONH(C1-C4 alkyl), —CONH2, —NHC(O)(C1-C4 alkyl), —NHC(O)(phenyl), —N(C1-C4 alkyl)C(O)(C1-C4 alkyl), —N(C1-C4 alkyl)C(O)(phenyl), —C(O)C1-C4 alkyl, —C(O)C1-C4 alkylphenyl, —C(O)C1-C4 haloalkyl, —OC(O)C1-C4 alkyl, —SO2(C1-C4 alkyl), —SO2(phenyl), —SO2(C1-C4 haloalkyl), —SO2NH2, —SO2NH(C1-C4 alkyl), —SO2NH(phenyl), —NHSO2(C1-C4 alkyl), —NHSO2(phenyl), and —NHSO2(C1-C4 haloalkyl).