Convenient total synthesis of taranabant (MK-0364), a novel cannabinoid-1 receptor inverse agonist as an anti-obesity agent

Being obese has various health problems that are related to type 2 diabetes mellitus, cardiovascular disease, hypertension, hyperlipidemia, and fibrinolytic abnormalities. Merck's taranabant (MK-0364), a CB1R inverse agonist, is currently in Phase 3 clinical trials, and is being actively pursue...

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Bibliographic Details
Published in:Tetrahedron 2007-12, Vol.63 (52), p.12845-12852
Main Authors: Kim, Min-ah, Kim, Jong Yup, Song, Kwang-Seop, Kim, Jeongmin, Lee, Jinhwa
Format: Article
Language:English
Subjects:
Anti-obesity
Evans asymmetric reaction
Hydride reduction
Taranabant
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Summary:Being obese has various health problems that are related to type 2 diabetes mellitus, cardiovascular disease, hypertension, hyperlipidemia, and fibrinolytic abnormalities. Merck's taranabant (MK-0364), a CB1R inverse agonist, is currently in Phase 3 clinical trials, and is being actively pursued by Merck toward obesity market. Merck intends to file for FDA approval of taranabant in 2008. In order to overcome practical difficulty involved in lab-scale preparation of taranabant with a dynamic kinetic resolution procedure developed by Merck's process group, we developed a ‘user-friendly’ method to install stereogenic centers by adopting Evans asymmetry chemistry. This method allowed us to prepare readily sub-gram scale of the target compound in a convenient way. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.10.056