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ChemicalBook CAS DataBase List Cabozantinib
849217-68-1

Cabozantinib synthesis

4synthesis methods
Cabozantinib, also known as XL-184 or BMS-907351, is an orally bioavailable, small molecule receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. Cabozantinib strongly binds to and inhibits several tyrosine receptor kinases. Specifically, cabozantinib appears to have a strong affinity for the hepatocyte growth factor receptor (Met) and vascular endothelial growth factor receptor 2 (VEGFR2), which may result in inhibition of tumor growth and angiogenesis, and tumor regression. Cabozantinib was approved by the U.S. FDA in November 2012 for the treatment of medullary thyroid cancer.
Synthetic Routes
  • ROUTE 1
  • 202112076800149584.jpg

    Laus, Gerhard; Schreiner, Erwin; Nerdinger, Sven; Kahlenberg, Volker; Wurst, Klaus; Vergeiner, Stefan; Schottenberger, Herwig. Crystal structures of intermediates in a new synthesis of antitumor drug cabozantinib. Heterocycles. Volume 93. Issue 1, Spec. Issue. Pages 323-332. Journal; Online Computer File. (2016).

  • ROUTE 2
  • 202112078496880618.jpg

    Lien, Vegard Torp; Klaveness, Jo; Olberg, Dag Erlend. One-step synthesis of [18F]cabozantinib for use in positron emission tomography imaging of c-Met. Journal of Labelled Compounds and Radiopharmaceuticals. Volume 61. Issue 1. Pages 11-17. Journal; Online Computer File. (2018).

  • ROUTE 3
  • 202112072394496434.jpg

    Xu, Wei; Donnelly, David J.; Chow, Patrick L.; Henley, Benjamin J. Method of preparing fluorine-18 labeled cabozantinib and its analogs. Assignee Exelixis, Inc., USA. WO 2016019285. (2016).

  • ROUTE 4
  • 202112073995788958.jpg

    Shi, Xiangfei; Zhao, Rui; Meng, Qingyi; Zhang, Xiquan. Process for the preparation of cabozantinib and its intermediate. Assignee Chia Tai Tianqing Pharmaceutical Group Co., Ltd., Peop. Rep. China. CN 103664776. (2014).

  • ROUTE 5
  • 202112077564641024.jpg

    Wang, Zhiguo; Song, Yanhong; Ma, Xiujuan; Tian, Beibei; Li, Shijiang; Li, Chao; Li, Tao; Zhang, Xin. Preparation method of Cabozantinib from diethyl malonate and 4-fluoroaniline. Assignee Shanghai Zaiqi Bio-Tech Co., Ltd., Peop. Rep. China. CN 106632028. (2015).

  • ROUTE 6
  • 202112071783771674.jpg

    Wang, Kunpeng; Han, Yuelin. New preparation method of cabozantinib. Assignee Nanjing Finetech Chemical Co., Ltd., Peop. Rep. China. CN 110240563. (2019).

202112076800149584.jpg

Laus, Gerhard; Schreiner, Erwin; Nerdinger, Sven; Kahlenberg, Volker; Wurst, Klaus; Vergeiner, Stefan; Schottenberger, Herwig. Crystal structures of intermediates in a new synthesis of antitumor drug cabozantinib. Heterocycles. Volume 93. Issue 1, Spec. Issue. Pages 323-332. Journal; Online Computer File. (2016).

1140909-48-3 Synthesis
Cabozantinib Malate

1140909-48-3
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Yield:849217-68-1 100%

Reaction Conditions:

with sodium hydrogencarbonate in water;ethyl acetate at 45; for 2 h;

Steps:

41 Example 41

A cabozantinib monolauryl sulfate salt was prepared by the following general procedure: a. 37 g of cabozantinib S-malate was added to a co-solvent of (1850 mL/740 mL) of ethyl acetate/l0% aqueous NaHC03 (50V/20V) and stirred at 45°C for 2 hour; (0518) b. The organic layer of the reaction mixture of step (a) was separated and washed twice with 740 mL of purified water (20V x 2); (0519) c. The organic extracts of step (b) were combined and concentrated to obtain cabozantinib free base as a white powder (29.2 g, 100% yield)

References:

WO2019/241504,2019,A1 Location in patent:Page/Page column 110

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