Canagliflozin

CAT#: H314203

CAS#: 842133-18-0

Description: Canagliflozin (INN, trade name Invokana) is a drug for the treatment of type 2 diabetes. It was developed by Mitsubishi Tanabe Pharma and is marketed under license by Janssen, a division of Johnson & Johnson. Canagliflozin is an inhibitor of subtype 2 sodium-glucose transport protein (SGLT2), which is responsible for at least 90% of the glucose reabsorption in the kidney. Blocking this transporter causes blood glucose to be eliminated through the urine. In March 2013, canagliflozin became the first SGLT2 inhibitor to be approved in the United States.

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Synthetic Routes

Canagliflozin - Synthetic Route 1

Canagliflozin route01

Synthetic reference

Nomura, Sumihiro; Sakamaki, Shigeki; Hongu, Mitsuya; Kawanishi, Eiji; Koga, Yuichi; Sakamoto, Toshiaki; Yamamoto, Yasuo; Ueta, Kiichiro; Kimata, Hirotaka; Nakayama, Keiko; Tsuda-Tsukimoto, Minoru. Discovery of Canagliflozin, a Novel C-Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Co-transporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus. Journal of Medicinal Chemistry. Volume 53. Issue 17. Pages 6355-6360. Journal. (2010).

Canagliflozin - Synthetic Route 2

Canagliflozin route02

Synthetic reference

Metil, Dattatray S.; Sonawane, Swapnil P.; Pachore, Sharad S.; Mohammad, Aaseef; Dahanukar, Vilas H.; McCormack, Peter J.; Reddy, Ch. Venkatramana; Bandichhor, Rakeshwar. Synthesis and Optimization of Canagliflozin by Employing Quality by Design (QbD) Principles. Organic Process Research & Development. Volume 22. Issue 1. Pages 27-39. Journal; Online Computer File. (2018).

Canagliflozin - Synthetic Route 3

Canagliflozin route03

Synthetic reference

Henschke, Julian P.; Wu, Ping-Yu; Lin, Chen-Wei; Chen, Shi-Feng; Chiang, Pei-Chen; Hsiao, Chi-Nung. β-Selective C-Arylation of Silyl Protected 1,6-Anhydroglucose with Arylalanes: The Synthesis of SGLT2 Inhibitors. Journal of Organic Chemistry. Volume 80. Issue 4. Pages 2295-2309. Journal; Online Computer File. (2015).

Canagliflozin - Synthetic Route 4

Canagliflozin route04

Synthetic reference

Patkar, Laxmikant Narahari; Mondkar, Harish Kashinath; Deshpande, Manoj Madhukarrao; Wagh, Yogesh Sambhaji; Vengurlekar, Rupesh Sudhir; Jadhav, Rupesh Sheshrao. Synthesis and purification of canagliflozin. Assignee USV Private Limited, India. IN 201621009743. (2017).

Canagliflozin - Synthetic Route 5

Canagliflozin route05

Synthetic reference

Vellanki, Siva Ram Prasad; Balusu, Raja Babu; Pilli, Ramakrishna; Javvaji, Rajeswara Rao; Annadasu, Ankama Nayudu. Process for the preparation of canagliflozin. Assignee Mylan Laboratories Ltd., India. IN 2014CH04366. (2016).

Canagliflozin - Synthetic Route 6

Canagliflozin route06

Synthetic reference

Liu, Yongjian; Wu, Mingjun; Xiao, Xinqiang; Tang, Guijun; Huang, Yinghao; Zhang, Rongxia; Li, Haihong. Method for preparation of 2,5-disubstituted thiophene compounds and their use in the preparation of canagliflozin. Assignee Topharman Shanghai Co., Ltd., Peop. Rep. China; Topharman Shandong Co., Ltd.. WO 2011079772. (2011).