Design and synthesis of novel DFG-Out RAF/vascular endothelial growth factor receptor 2 (VEGFR2) inhibitors. 1. Exploration of [5,6]-fused bicyclic scaffolds

Journal of Medicinal Chemistry

Volumn 55, Issue 7, 2012, Pages 3452-3478

  Okaniwa, Masanori ^a   Hirose, Masaaki ^a   Imada, Takashi ^a   Ohashi, Tomohiro ^a   Hayashi, Youko ^a   Miyazaki, Tohru ^a   Arita, Takeo ^a   Yabuki, Masato ^a   Kakoi, Kazuyo ^a   Kato, Juran ^a   Takagi, Terufumi ^a   Kawamoto, Tomohiro ^a   Yao, Shuhei ^a   Sumita, Akihiko ^a   Tsutsumi, Shunichirou ^a   Tottori, Tsuneaki ^a   Oki, Hideyuki ^a   Sang, Bi Ching ^b   Yano, Jason ^b   Aertgeerts, Kathleen ^b   Yoshida, Sei ^a   Ishikawa, Tomoyasu ^a   more..

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

^b Takeda San Diego Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 3 (1 CYANOCYCLOPROPYL) N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO][1,3]THIAZOLO[5,4 B]PYRIDIN 5 YL]OXY]PHENYL]BENZAMIDE; 2 CHLORO 3 (1 CYANOCYCLOPROPYL) N [5 [[2 [(CYCLOPROPYLCARBONYL)AMINO][1,3]THIAZOLO[5,4 B]PYRIDIN 5 YL]OXY] 2 FLUOROPHENYL] BENZAMIDE; 2 CHLORO 3 (1 CYANOCYCLOPROPYL) N [5 [[2 [(CYCLOPROPYLCARBONYL)AMINO][1,3]THIAZOLO[5,4 B]PYRIDIN 5 YL]OXY] 2 FLUOROPHENYL]BENZAMIDE; 2 CHLORO N [2 CHLORO 5 [[2 [(CYCLOPROPYLCARBONYL)AMINO][1,3]THIAZOLO[5,4 B]PYRIDIN 5 YL]OXY]PHENYL] 3 (1 CYANOCYCLOPROPYL)BENZENE; 3 (1 CYANO 1 METHYLETHYL) N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO] 1 METHYL 1H BENZIMIDAZOL 6 YL]OXY]PHENYL]BENZAMIDE; 3 (1 CYANO 1 METHYLETHYL) N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO] 1H BENZIMIDAZOL 6 YL]OXY]PHENYL]BENZAMIDE; 3 (1 CYANO 1 METHYLETHYL) N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 A]PYRIDIN 6 YL]OXY]PHENYL]BENZAMIDE; 3 (1 CYANO 1 METHYLETHYL) N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL]BENZAMIDE; 3 (1 CYANO 1 METHYLETHYL) N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO][1,3]THIAZOLO[5,4 B]PYRIDIN 5 YL]OXY]PHENYL]BENZAMIDE; 3 (1 CYANOCYCLOPROPYL) N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO][1,3]THIAZOLO[5,4 B]PYRIDIN 5 YL]OXY]PHENYL]BENZAMIDE; 3 TERT BUTOXY N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL]BENZAMIDE; ANTINEOPLASTIC AGENT; ETHYL 6 (3 AMINOPHENOXY)IMIDAZO[1,2 B]PYRIDAZINE 2 CARCARBOXYLATE; METHYL 3 [[[3 ([2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL]AMINO]CARBONYL]BENZOATE; N [3 [(2 ACETAMIDOIMIDAZO[1,2 B]PYRIDAZIN 6 YL)OXY]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [[2 (ISOBUTYRYLAMINO)IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL) 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [[2 (PROPIONYLAMINO)IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [[2 [(CYCLOBUTYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [[2 [(CYCLOPENTYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 2 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 3 (1 HYDROXY 1 METHYLETHYL)BENZAMIDE; N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 3 (TRIFLUOROMETHYL)BENZAMIDE; N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 3 METHOXYBENZAMIDE; N [3 [[2 [(CYCLOPROPYLCARBONYL)AMINO]IMIDAZO[1,2 B]PYRIDAZIN 6 YL]OXY]PHENYL] 4 (TRIFLUOROMETHYL)BENZAMIDE; N [5 [(5 AMINOPYRIDIN 2 YL)OXY] 2 CHLOROPHENYL] 2,2,2 TRIFLUOROACETAMIDE; N [6 [3 [[[3 (TRIFLUOROMETHYL)PHENYL]CARBONYL]AMINO]PHENOXY]IMIDAZO[1,2 B]PYRIDAZIN 2 YL]TETRAHYDRO 2H PYRAN 4 CARBOXAMIDE; RAF PROTEIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VASCULOTROPIN INHIBITOR; VASCULOTROPIN RECEPTOR 2;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL INTERACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG FORMULATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME PHOSPHORYLATION; HYDROGEN BOND; MELANOMA; NONHUMAN; RAT; SINGLE DRUG DOSE; TUMOR REGRESSION; TUMOR XENOGRAFT; X RAY;

EID: 84859805869     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300126x     Document Type: Article

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