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Crizotinib

CAT#: H202222

CAS#: 877399-52-5

Description: Crizotinib, also known as PF-02341066, is an orally bioavailable agent belonging to the class of c-met/hepatocyte growth factor receptor (HGFR) tyrosine kinase inhibitors with potential antineoplastic activity. Crizotinib was approved for treatment of some non-small cell lung carcinoma (NSCLC) in the US, and undergoing clinical trials testing its safety and efficacy in anaplastic large cell lymphoma, neuroblastoma, and other advanced solid tumors in both adults and childre. Crizotinib inhibits the membrane receptor MET and activation of the MET signaling pathway, which may block tumor cell growth, migration and invasion, and tumor angiogenesis in susceptible tumor cell populations. Crizotinib was approved in 2011.

Synthetic Routes

Crizotinib - Synthetic Route 1

Synthetic reference

Cui, J. Jean; Tran-Dube, Michelle; Shen, Hong; Nambu, Mitchell; Kung, Pei-Pei; Pairish, Mason; Jia, Lei; Meng, Jerry; Funk, Lee; Botrous, Iriny; McTigue, Michele; Grodsky, Neil; Ryan, Kevin; Padrique, Ellen; Alton, Gordon; Timofeevski, Sergei; Yamazaki, Shinji; Li, Qiuhua; Zou, Helen; Christensen, James; Mroczkowski, Barbara; Bender, Steve; Kania, Robert S.; Edwards, Martin P. Structure Based Drug Design of Crizotinib (PF-02341066), a Potent and Selective Dual Inhibitor of Mesenchymal-Epithelial Transition Factor (c-MET) Kinase and Anaplastic Lymphoma Kinase (ALK). Journal of Medicinal Chemistry. Volume 54. Issue 18. Pages 6342-6363. Journal; Online Computer File. (2011).

Crizotinib - Synthetic Route 2

Synthetic reference

Qian, Jian-Qiang; Yan, Pu-Cha; Che, Da-Qing; Zhou, Qi-Lin; Li, Yuan-Qiang. A novel approach for the synthesis of Crizotinib through the key chiral alcohol intermediate by asymmetric hydrogenation using highly active Ir-Spiro-PAP catalyst. Tetrahedron Letters. Volume 55. Issue 9. Pages 1528-1531. Journal; Online Computer File. (2014).

Crizotinib - Synthetic Route 3

Synthetic reference

de Koning, Pieter D.; McAndrew, Douglas; Moore, Robert; Moses, Ian B.; Boyles, David C.; Kissick, Kyle; Stanchina, Corey L.; Cuthbertson, Timothy; Kamatani, Asayuki; Rahman, Leera; Rodriguez, Rick; Urbina, Armando; Sandoval, Alison; Rose, Peter R. Fit-for-Purpose Development of the Enabling Route to Crizotinib (PF-02341066). Organic Process Research & Development. Volume 15. Issue 5. Pages 1018-1026. Journal; Online Computer File. (2011).

Crizotinib - Synthetic Route 4

Synthetic reference

Wang, Xin; Liu, Wei-Gang; Tung, Chen-Ho; Wu, Li-Zhu; Cong, Huan. A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions. Organic Letters. Volume 21. Issue 20. Pages 8158-8163. Journal; Online Computer File. (2019).

Crizotinib - Synthetic Route 5

Synthetic reference

Yang, Ming; Shen, Chao; Wang, Dong; Yang, Yong; Ren, Yongqi. Method for synthesizing antitumor drug Crizotinib. Assignee Zhejiang Keju Biopharmaceutical Co., Ltd., Peop. Rep. China. CN 108341802. (2018).

Crizotinib - Synthetic Route 6

Synthetic reference

Zhang, Junyong. Process for synthesis of Crizotinib and intermediates thereof. Assignee Shanghai Run Biotech Co., Ltd., Peop. Rep. China. CN 107365301. (2017).

Crizotinib - Synthetic Route 7

Synthetic reference

Liu, Hai; Li, Hanpu; Li, Jianzhi; Chi, Wangzhou; Zheng, Xiaoli; Sun, Li. Process for preparation of micromolecule kinase inhibitor. Assignee Shanghai Tianci Biological Valley Engineering Co., Ltd., Peop. Rep. China. CN 106632260. (2017).

Crizotinib - Synthetic Route 8

Synthetic reference

Pi, Hongjun; Ma, Jun; Liu, Xingwei. Method for synthesizing Crizotinib. Assignee Gansu Haojun Pharmaceutical Technology Co., Ltd., Peop. Rep. China. CN 105924431. (2016).