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Regorafenib monohydrate

Regorafenib monohydrate Structure
CAS No.
1019206-88-2
Chemical Name:
Regorafenib monohydrate
Synonyms
Regorafenib H2O;Regorafenib hydrate;Regfenib monohydrate;Regorafenib (200 mg);Refined Sunflower Oil;BAY 73-4506 Monohydrate;Regorafenib monohydrate;Regorafenibhydrate USP/EP/BP;Regorafenib (BAY 73-4506)Monohydrate;Regorafenib monohydrate (BAY 73-4506)
CBNumber:
CB52641189
Molecular Formula:
C21H17ClF4N4O4
Molecular Weight:
500.83
MOL File:
1019206-88-2.mol
MSDS File:
SDS
Modify Date:
2024/7/25 20:04:46
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Regorafenib monohydrate Properties

storage temp. 2-8°C
solubility ≥25.05 mg/mL in DMSO; insoluble in H2O
form solid
color Light yellow to orange
InChIKey ZOPOQLDXFHBOIH-UHFFFAOYSA-N
SMILES O(C1C=CC(NC(=O)NC2C=CC(Cl)=C(C(F)(F)F)C=2)=C(F)C=1)C1=CC=NC(C(=O)NC)=C1.O

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08,GHS09
Signal word  Warning
Hazard statements  H361fd-H373-H410
Precautionary statements  P201-P273-P308+P313

Regorafenib monohydrate Chemical Properties,Uses,Production

Description

Regorafenib monohydrate (BAY 73-4506) is an orally active and potent multi-targeted receptor tyrosine kinase inhibitor with potent anti-tumour and anti-angiogenic activity. It is approved for the treatment of metastatic colorectal cancer, advanced gastrointestinal mesenchymal stromal tumours and hepatocellular carcinoma.

Mechanism of action

The mechanism of anticancer action of Regorafenib monohydrate is similar to that of Regorafenib, an oral multikinase inhibitor that blocks tyrosine kinases that are active in angiogenesis, cancer development and growth, and maintenance of the tumour microenvironment. It is superior to sorafenib in blocking both vascular endothelial growth factor receptor and TIE2, a molecule with an important role in angiogenesis.

Clinical Use

Regorafenib was approved by the U.S. Food and Drug Administration (FDA) in September 2012 for the treatment of metastatic colorectal cancer in patients who have previously undergone fluoropyrimidine-, oxaliplatin-, and irinotecan-based therapies. The FDA expanded the approved use of the drug to include patients with advanced gastrointestinal stromal tumors (GIST) that cannot be surgically removed and no longer respond to imatinib and sunitinib, two other drugs approved for treatment of GIST. Regorafenib, marketed under the trade name Stivarga®, was discovered and developed by Bayer Pharmaceuticals and marketed jointly with Onyx Pharmaceuticals. The active metabolites of the drug inhibit multiple targets within a variety of kinase families including those in the RET, VEGF, FGFR, PTK, and Abl pathways.

Synthesis

Among several published synthesis, the most likely process scale synthesis will be highlighted from the two published syntheses, and this is described in the scheme. Commercially available picolinic acid (148) was heated with thionyl chloride to provide the crude intermediate 4-chloro-2- pyridyl acid chloride which was subsequently reacted with aqueous methyl amine in toluene to give 4- chloro-2-methylcarboxamide as its hydrochloride salt 149 in quantitative yield after treatment with acetyl chloride in toluene and ethanol. The hydrochloride salt was free based with sodium hydroxide and then immediately reacted with imine 150 (formed upon exposure to 4-amino-3-fluorophenol (153) in refluxing 3-methyl 2-butanone) in base to provide diaryl ether 151 in 84% yield. Reaction of amine 151 with the commercially available isocyanate 152 ultimately delivered regorafenib hydrate (XXIII) in 83% yield.

Synthesis_1019206-88-2

Regorafenib monohydrate Preparation Products And Raw materials

Raw materials

Regorafenib

Preparation Products

Regorafenib monohydrate Suppliers

Global( 244)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
SynZeal Research Pvt Ltd +1 226-802-2078 Gujarat, India 6522 58 Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6773 58 Inquiry
Pharma Affiliates 172-5066494 Haryana, India 6761 58 Inquiry
A.J Chemicals 91-9810153283 New Delhi, India 6124 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
Yangzhou Qinyuan Pharmatech Co.,ltd +86-18752526868 China 71 58 Inquiry
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD. +86-18600796368 +86-18600796368 China 123 58 Inquiry
Hebei Yanxi Chemical Co., Ltd. +86-17531190177; +8617531190177 China 5873 58 Inquiry
Capot Chemical Co.,Ltd. 571-85586718 +8613336195806 China 29798 60 Inquiry
Henan Tianfu Chemical Co.,Ltd. +86-0371-55170693 +86-19937530512 China 21668 55 Inquiry
Supplier Advantage
SynZeal Research Pvt Ltd 58
Pharmaffiliates Analytics and Synthetics P. Ltd 58
Pharma Affiliates 58
A.J Chemicals 58
CLEARSYNTH LABS LTD. 58
Yangzhou Qinyuan Pharmatech Co.,ltd 58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD. 58
Hebei Yanxi Chemical Co., Ltd. 58
Capot Chemical Co.,Ltd. 60
Henan Tianfu Chemical Co.,Ltd. 55

Regorafenib monohydrate Spectrum

4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-2-pyridinecarboxamide hydrate(1019206-88-2)1HNMR

1019206-88-2(Regorafenib monohydrate)Related Search:

Alectinib Hydrochloride PLX4032 Nintedanib Ethanesulfonate Salt Olaparib 4-Amino-3-fluorophenol
4-(4-AMINO-3-FLUOROPHENOXY)-N-METHYLPICOLINAMIDE 4-Chloro-alpha,alpha,alpha-trifluoro-m-toluidine Regorafenib Crizotinib Afatinib (BIBW 2992)
PLERIXAFOR Regorafenib (Hydrochloride) SOLITHROMYCIN Afatinib dimaleate Dacomitinib (PF299804)
Cabozantinib Malate 918504-65-1 1110813-31-4
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4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-2-pyridinecarboxamide hydrate Regorafenib monohydrate Regorafenib (BAY 73-4506)Monohydrate Regorafenib hydrate BAY 73-4506 Monohydrate Regorafenib monohydrate 4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-2-pyridinecarboxamide hydrate 4-[4-({[4-Chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-N-methyl-2-pyridinecarboxamide hydrate (1:1) 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]-3-fluorophenoxy]-N-methylpyridine-2-carboxamide,hydrate Regorafenib monohydrate (BAY 73-4506) Regorafenib H2O 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)-N-methylpicolinamide hydrate Regorafenibhydrate USP/EP/BP 4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-2-pyridinecarboxamide hydrate USP/EP/BP 4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-2-pyridi Refined Sunflower Oil Regfenib monohydrate Regorafenib (200 mg) 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)-N-methylpicolinamide hydrate , Regorafenib monohydrate 1019206-88-2 C21H15ClF4N4O3H2O C21H17ClF4N4O4 API