Apixaban

CAT#: H 300170

CAS#: 503612-47-3

Description: Apixaban, also known as BMS-56224701, is an anticoagulant for the treatment of venous thromboembolic events. Apixaban is a direct factor Xa inhibitor. Apixaban was approved in 2012. Apixaban is indicated for the following: (1) To lower the risk of stroke and embolism in patients with nonvalvular atrial fibrillation. (2) Deep vein thrombosis (DVT) prophylaxis. DVT's may lead to pulmonary embolism (PE) in knee or hip replacement surgery patients. (3) Treatment of both DVT and PE. (4) To reduce the risk of recurring DVT and PE after initial therapy.

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Synthetic Routes

Apixaban - Synthetic Route 1

Apixaban route01

Synthetic reference

Sun, Xiaoqing; Hong, Zexin; Liu, Moyi; Guo, Su; Yang, Di; Wang, Yong; Lan, Tian; Gao, Linyu; Qi, Hongxia; Gong, Ping; Liu, Yajing. Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity. Bioorganic & Medicinal Chemistry. Volume 25. Issue 10. Pages 2800-2810. Journal; Online Computer File. (2017).

Apixaban - Synthetic Route 2

Apixaban route02

Synthetic reference

: Pinto, Donald J. P.; Orwat, Michael J.; Koch, Stephanie; Rossi, Karen A.; Alexander, Richard S.; Smallwood, Angela; Wong, Pancras C.; Rendina, Alan R.; Luettgen, Joseph M.; Knabb, Robert M.; He, Kan; Xin, Baomin; Wexler, Ruth R.; Lam, Patrick Y. S. Discovery of 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxo-1-piperidinyl]phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (Apixaban, BMS-562247), a Highly Potent, Selective, Efficacious, and Orally Bioavailable Inhibitor of Blood Coagulation Factor Xa. Journal of Medicinal Chemistry. Volume 50. Issue 22. Pages 5339-5356. Journal. (2007).

Apixaban - Synthetic Route 3

Apixaban route03

Synthetic reference

Nevuluri, Narasimha Rao; Rapolu, Rajesh Kumar; Iqbal, Javed; Kandagatla, Bhaskar; Sen, Saikat; Dahanukar, Vilas H.; Oruganti, Srinivas. A morpholine-free process amenable convergent synthesis of apixaban: a potent factor Xa inhibitor. Monatshefte fuer Chemie. Volume 148. Issue 8. Pages 1477-1482. Journal; Online Computer File. (2017).

Apixaban - Synthetic Route 4

Apixaban route04

Synthetic reference

Tao, Hai-yan; Mi, Bin; Guo, Guo-xian; Gong, Ping. Synthesis of apixaban. Zhongguo Yaowu Huaxue Zazhi. Volume 23. Issue 5. Pages 385-389. Journal. (2013)

Apixaban - Synthetic Route 5

Apixaban route05

Synthetic reference

Gu, Xifeng; Xu, Jun; Lu, Ming. Synthesis method of apixaban from its precursor. Assignee ChemFuture PharmaTech (Jiangsu) Ltd., Peop. Rep. China. CN 103896940. (2014).