1005785-71-6

Basic information

• Product Name: 6-iodoimidazo[1,2-b]pyridazin-2-amine
• Synonyms: 6-iodoimidazo[1,2-b]pyridazin-2-amine
• CAS NO: 1005785-71-6
• Molecular Formula: C₆H₅IN₄
• Molecular Weight: 260.03517
• Mol File: 1005785-71-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-iodoimidazo[1,2-b]pyridazin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-iodoimidazo[1,2-b]pyridazin-2-amine(1005785-71-6)
• EPA Substance Registry System: 6-iodoimidazo[1,2-b]pyridazin-2-amine(1005785-71-6)

Safety Data

• Hazardous Substances Data: 1005785-71-6(Hazardous Substances Data)

Upstream product

• 1005785-69-2 ethyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamate 
• 1005787-84-7 tert-butyl N-[6-iodoimidazo[1,2-b]pyridazin-2-yl]carbamate 

Downstream Products

• 1005782-74-0 6-(3-aminophenoxy)imidazo[1,2-b]pyridazine-2-amine 
• 1005777-50-3 N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazine-2-yl]cyclopropanecarboxamide 
• 1429334-61-1 N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-4-(trifluoromethyl)benzamide 
• 1005780-65-3 N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-3-(trifluoromethyl)benzamide 
• 1005788-57-7 N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclohexanecarboxamide 
• 1005780-85-7 N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide 
• 1005781-18-9 N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-3,5-dimethylisoxazole-4-carboxamide 
• 1005781-10-1 N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1,5-dimethyl-1H-pyrazole-3-carboxamide 
• 1005781-21-4 N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-1-methyl-1H-1,2,3-triazole-5-carboxamide 
• 1005780-56-2 N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-3-methylisoxazole-5-carboxamide 
• 1005778-31-3 C₂₀H₁₆N₆O₄ 
• 1005782-14-8 N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]isonicotinamide 
• 1005778-10-8 C₂₁H₂₃N₅O₃ 
• 1005778-04-0 C₂₀H₁₉N₅O₃ 

Relevant articles and documents

Discovery of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin- 6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (TAK-593), a highly potent VEGFR2 kinase inhibitor

Vascular endothelial growth factor (VEGF) plays important roles in tumor angiogenesis, and the inhibition of its signaling pathway is considered an effective therapeutic option for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of 2-acylamino-6-phenoxy-imidazo[1,2-b]pyridazine derivatives. Hybridization of two distinct imidazo[1,2-b]pyridazines 1 and 2, followed by optimization led to the discovery of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl} oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (23a, TAK-593) as a highly potent VEGF receptor 2 kinase inhibitor with an IC50 value of 0.95 nM. The compound 23a strongly suppressed proliferation of VEGF-stimulated human umbilical vein endothelial cells with an IC50 of 0.30 nM. Kinase selectivity profiling revealed that 23a inhibited platelet-derived growth factor receptor kinases as well as VEGF receptor kinases. Oral administration of 23a at 1 mg/kg bid potently inhibited tumor growth in a mouse xenograft model using human lung adenocarcinoma A549 cells (T/C = 8%).

FUSED HETEROCYCLIC DERIVATIVE AND USE THEREOF

The present invention provides a fused heterocyclic derivative having a potent kinase inhibitory activity and use thereof. A compound represented by the formula (I): wherein each symbol is as defined in the specification, except a particular compound, or a salt thereof, and a pharmaceutical agent containing the compound or a prodrug thereof, which is a kinase (VEGFR, VEGFR2, PDGFR, Raf) inhibitor, an angiogenesis inhibitor, an agent for the prophylaxis or treatment of cancer, a cancer growth inhibitor or a cancer metastasis suppressor.