Regorafenib monohydrate
|
|
|
- CAS-Nr.
- 1019206-88-2
- Englisch Name:
- Regorafenib monohydrate
- Synonyma:
- Regorafenib hydrate;Refined Sunflower Oil;4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-2-pyridinecarboxamide hydrate;Regorafenib H2O;Regfini hydrate;Regfenib monohydrate;Regorafenib (200 mg);Regorafenib monohydrate;BAY 73-4506 Monohydrate;Regorafenibhydrate USP/EP/BP
- CBNumber:
- CB52641189
- Summenformel:
- C21H17ClF4N4O4
- Molgewicht:
- 500.83
- MOL-Datei:
- 1019206-88-2.mol
|
Regorafenib monohydrate Eigenschaften
- storage temp.
- 2-8°C
- L?slichkeit
- ≥25.05 mg/mL in DMSO; insoluble in H2O
- Aggregatzustand
- solid
- Farbe
- Light yellow to orange
- InChI
- 1S/C21H15ClF4N4O3.H2O/c1-27-19(31)18-10-13(6-7-28-18)33-12-3-5-17(16(23)9-12)30-20(32)29-11-2-4-15(22)14(8-11)21(24,25)26;/h2-10H,1H3,(H,27,31)(H2,29,30,32);1H2
- 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
Regorafenib monohydrate Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
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.
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.
Nebenwirkungen
Common side effects of regorafenib monohydrate include hand-foot skin reaction, diarrhea, nausea, vomiting, decreased appetite, fatigue, hypertension, and fever.
Synthese
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.
Regorafenib monohydrate Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Regorafenib monohydrate Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 272)Lieferanten
1019206-88-2()Verwandte Suche:
- Regorafenib monohydrate
- Regorafenib (BAY 73-4506)Monohydrate
- 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
- Regfenib monohydrate
- Regorafenib (200 mg)
- 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)-N-methylpicolinamide hydrate , Regorafenib monohydrate
- Regfini hydrate
- Regorafenib monohydrate, 10 mM in DMSO
- Regorafenib monohydrate (BAY 73-4506 monohydrate)
- 2-Pyridinecarboxamide, 4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-, hydrate (1:1)
- 4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]-3-fluorophenoxy]-N-methyl-2-pyridinecarboxamide hydrate
- Refined Sunflower Oil
- Regorafenib hydrate
- 1019206-88-2
- C21H15ClF4N4O3H2O
- C21H17ClF4N4O4
- API
