ChemicalBook CAS DataBase List NVP-LDE225

NVP-LDE225 synthesis

4synthesis methods

Product Name:NVP-LDE225
CAS Number:956697-53-3
Molecular formula:C26H26F3N3O3
Molecular Weight:485.5

Sonidegib, also known as, erismodegib, LDE225, NVP-LDE225, is an orally bioavailable small-molecule Smoothened (Smo) antagonist with potential antineoplastic activity. Erismodegib selectively binds to the Hedgehog (Hh)-ligand cell surface receptor Smo, which may result in the suppression of the Hh signaling pathway and, so, the inhibition of tumor cells in which this pathway is abnormally activated. It was approved by the FDA for treating basal cell carcinoma in July 2015. Synthetic Description Reference: Wang, Deyin; Xu, Xin; Qi, Yuxin; Wang, Baolin; Zhang, Wei; Zhao, Yinlong. Preparation of Sonidegib and intermediate thereof. CN 109293649. (Xinfa Pharmaceutical Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Xu, Xuenong. A method for preparation of Sonidegib with L-lactate. WO 2017096998. (Suzhou Miracpharma Technology Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Rajan, Srinivasan Thirumalai. Process for the preparation of N-[6-(cis-2,6-dimethylmorpholin-4-yl)pyridine-3-yl]-2-methyl-4'-(trifiuoromethoxy) [1,1' -biphenyl]-3-carboxamide and its polymorphs. WO 2017163258. (MSN Laboratories Private Limited, India; Eswaraiah, Sajja; Rao, Gogulapati Venkata Panakala; Reddy, Sagyam Rajeshwa; Rajesham, Boge; Reddy, Purna Chndrasekhar Thippireddy) Synthetic Description Reference: Rajan, Srinivasan Thirumalai. Process for the preparation of N-[6-(cis-2,6-dimethylmorpholin-4-yl)pyridine-3-yl]-2-methyl-4'-(trifiuoromethoxy) [1,1' -biphenyl]-3-carboxamide and its polymorphs. WO 2017163258. (MSN Laboratories Private Limited, India; Eswaraiah, Sajja; Rao, Gogulapati Venkata Panakala; Reddy, Sagyam Rajeshwa; Rajesham, Boge; Reddy, Purna Chndrasekhar Thippireddy) Synthetic Description Reference: Xu, Xuenong. A method for preparation of Sonidegib with L-lactate. CN 105330658. (Suzhou Miracpharma Technology Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Fritze, Andreas; Corcelle, Karine; Grubesa, Melinda Enikoe. Pharmaceutical compositions. WO 2011009852. (Novartis AG, Switz.)

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

Reference: Wang, Deyin; Xu, Xin; Qi, Yuxin; Wang, Baolin; Zhang, Wei; Zhao, Yinlong. Preparation of Sonidegib and intermediate thereof. CN 109293649. (Xinfa Pharmaceutical Co., Ltd., Peop. Rep. China)

4548-45-2 Synthesis

4548-45-2
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956697-53-3
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Yield:-

Steps:

Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 50 °C
2: hydrogen; palladium on activated charcoal / methanol
3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide

References:

Salati;Stathis [Drugs of the Future,2014,vol. 39,# 10,p. 677 - 684]

139301-27-2 Synthesis