Synthesis, Optimization, and Large-Scale Preparation of the Low-Dose Central Nervous System-Penetrant BACE1 Inhibitor LY3202626 via a [3 + 2] Nitrone Cycloaddition-Reference-Cited by-同舟云学术

Synthesis, Optimization, and Large-Scale Preparation of the Low-Dose Central Nervous System-Penetrant BACE1 Inhibitor LY3202626 via a [3 + 2] Nitrone Cycloaddition

Published:2020-01-29 Issue:2 Volume:24 Page:306-314
ISSN:1083-6160
Container-title:Organic Process Research & Development
language:en
Short-container-title:Org. Process Res. Dev.

Author:

Garcia-Losada Pablo¹,DeBaillie Amy C.²,Eugenio de Diego Jose¹,Green Steven J.³,Hansen Marvin M.²,Jaramillo Carlos¹,Johnson Matt⁴,Kaoudi Talbi¹,Li Jiuyuan⁴,Lindsay-Scott Peter J.⁵^ORCID,Mateos Carlos¹^ORCID,Mergott Dustin J.³,Rincon Juan Antonio¹,Rothhaar Roger R.²,Seibert Kevin D.²,Watson Brian M.³,Winneroski Leonard L.³,Gangula Srinivas⁴^ORCID,Jing Dajiang⁴,Sun Hao⁴,Zhang Lei⁴,Frederick Michael O.²^ORCID

Affiliation:

1. Centro de Investigación Lilly S.A., Avda. de la Industria 30, Alcobendas-Madrid 28108, Spain

2. Small Molecule Design and Development, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, United States

3. Lilly Research Laboratories, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, United States

4. Asymchem Life Science (Tianjin) Co., Ltd., 71 Seventh Avenue, TEDA, Tianjin 300457, P. R. China

5. Lilly Research Laboratories, Erl Wood Manor, Windlesham, Surrey GU20 6PH, United Kingdom

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.9b00471

Reference29 articles.

1. The Potent BACE1 Inhibitor LY2886721 Elicits Robust Central A Pharmacodynamic Responses in Mice, Dogs, and Humans

2. bAudia, J. E.; Mergott, D. J.; Sheehan, S. M.; Watson, B. M. Aminodihydrothiazine derivatives as BACE inhibitors for the treatment of Alzheimer’s disease. WO 2009134617 A1, November 5, 2009.

3. Green, S. J.; Mergott, D. J.; Watson, B. M.; Winneroski, L. L. Tetrahydropyrrolothiazine compounds. US 8987254 B2, March 24, 2015.

4. Pilot-Scale Continuous Production of LY2886721: Amide Formation and Reactive Crystallization

5. Synthesis of BACE Inhibitor LY2886721. Part I. An Asymmetric Nitrone Cycloaddition Strategy

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