Alectinib synthetic routes

CAT#: 326661 | Name: Ertugliflozin | CAS# 1210344-57-2

Purchases for research

Description:

Ertugliflozin, also known as also known as PF-04971729, is a potent and selective inhibitor of the sodium-dependent glucose cotransporter 2 and clinical candidate for the treatment of type 2 diabetes mellitus. clinical study showed that Ertugliflozin (1-25 mg/day) improved glycaemic control, body weight and blood pressure in patients with T2DM suboptimally controlled on metformin, and was well tolerated.

Synthetic Routes

Ertugliflozin - Synthetic Route 1

Ertugliflozin - Synthetic Route 1

Synthetic reference

Bernhardson, David; Brandt, Thomas A.; Hulford, Catherine A.; Lehner, Richard S.; Preston, Brian R.; Price, Kristin; Sagal, John F.; St. Pierre, Michael J.; Thompson, Peter H.; Thuma, Benjamin. Development of an Early-Phase Bulk Enabling Route to Sodium-Dependent Glucose Cotransporter 2 Inhibitor Ertugliflozin. Org. Process Res. Dev.201418157-65. Publication Date:January 3, 2014. https://doi.org/10.1021/op400289z.

Ertugliflozin - Synthetic Route 2

Ertugliflozin - Synthetic Route 2

Synthetic reference

Bowles, Paul; Brenek, Steven J.; Caron, Stephane; Do, Nga M.; Drexler, Michele T.; Duan, Shengquan; Dube, Pascal; Hansen, Eric C.; Jones, Brian P.; Jones, Kris N.; Ljubicic, Tomislav A.; Makowski, Teresa W.; Mustakis, Jason; Nelson, Jade D.; Olivier, Mark; Peng, Zhihui; Perfect, Hahdi H.; Place, David W.; Ragan, John A.; Salisbury, John J.; Stanchina, Corey L.; Vanderplas, Brian C.; Webster, Mark E.; Weekly, R. Matt. Commercial Route Research and Development for SGLT2 Inhibitor Candidate Ertugliflozin. Org. Process Res. Dev.201418166-81. Publication Date:December 20, 2013. https://doi.org/10.1021/op4002802.

Ertugliflozin - Synthetic Route 3

Ertugliflozin - Synthetic Route 3

Synthetic reference

Mascitti V, Préville C. Stereoselective synthesis of a dioxa-bicyclo[3.2.1]octane SGLT2 inhibitor. Org Lett. 2010 Jul 2;12(13):2940-3. doi: 10.1021/ol100940w. PubMed PMID: 20527898.

Ertugliflozin - Synthetic Route 4

Ertugliflozin - Synthetic Route 4

Synthetic reference

Mascitti, Vincent. Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives. WO 2011051864. (Assignee Pfizer Inc., USA)

Ertugliflozin - Synthetic Route 5

Ertugliflozin - Synthetic Route 5

Synthetic reference

Brenek, Steven J.; Caron, Stephanie; Nelson, Jade D.; Webster, Mark E.; Weekly, Rodney Matthew. Methods for preparing SGLT2 inhibitors. WO 2014159151. (Assignee MSD International GmbH, Switz.)

Ertugliflozin - Synthetic Route 6

Ertugliflozin - Synthetic Route 6

Synthetic reference

Ali, Israr; Kumar, Rajesh; Barman, Dhiren Chandra; Nath, Asok; Prasad, Mohan. Processes for the preparation of ertugliflozin via cyclization reaction. WO 2016088081. (Assignee SUN Pharmaceutical Industries Limited, India)

Ertugliflozin - Synthetic Route 7

Ertugliflozin - Synthetic Route 7

Synthetic reference

Lauring, Brett; Engel, Samuel S.; Terra, Steven G.; Rusnak, James M. Methods of treating or reducing the risk of cardiovascular events and related diseases using SGLT-2 inhibitors. WO 2017155841. (Assignee Merck Sharp & Dohme Corp., USA; Pfizer Inc.)

Ertugliflozin - Synthetic Route 8

Ertugliflozin - Synthetic Route 8

Synthetic reference

Zheng, Xuchun; Zhang, Yiping; Fu, Chenchen. Preparation and intermediate of ertugliflozin. CN 107382952. (Assignee Hangzhou Cheminspire Technologies Co., Ltd., Peop. Rep. China)

Ertugliflozin - Synthetic Route 9

Ertugliflozin - Synthetic Route 9

Synthetic reference

Wu, Guaili; Qiu, Zhenjun; Bian, Lin; Lu, Yun. Method for one-pot preparing sodium-glucose cotransporter 2 inhibitor. CN 107686496. (Assignee Jiangsu Hengrui Medicine Co., Ltd., Peop. Rep. China)

Ertugliflozin - Synthetic Route 10

Ertugliflozin - Synthetic Route 10

Synthetic reference

Virginia V. Triantakonstanti, Olga G. Mountanea, Kyriaki-Eleni C. Papoulidou, Thanos Andreou, Theocharis V. Koftis, John K. Gallos. Studies towards the synthesis of ertugliflozin from l-Arabinose. Tetrahedron, Volume 74, Issue 39, 2018, Pages 5700-5708, ISSN 0040-4020, https://doi.org/10.1016/j.tet.2018.08.005.

Ertugliflozin - Synthetic Route 11

Ertugliflozin - Synthetic Route 11

Synthetic reference

Virginia V.; Andreou, Thanos; Koftis, Theoharis V.; Gallos, John K. Synthesis of ertugliflozin from D-glucose. Tetrahedron Letters. 2019, 60(14): 994-996.

Ertugliflozin - Synthetic Route 12

Ertugliflozin - Synthetic Route 12

Synthetic reference

Mascitti V, Maurer TS, Robinson RP, Bian J, Boustany-Kari CM, Brandt T, Collman BM, Kalgutkar AS, Klenotic MK, Leininger MT, Lowe A, Maguire RJ, Masterson VM, Miao Z, Mukaiyama E, Patel JD, Pettersen JC, Préville C, Samas B, She L, Sobol Z, Steppan CM, Stevens BD, Thuma BA, Tugnait M, Zeng D, Zhu T. Discovery of a clinical candidate from the structurally unique dioxa-bicyclo[3.2.1]octane class of sodium-dependent glucose cotransporter 2 inhibitors. J Med Chem. 2011, 54(8):2952-60