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Discovery of Narlaprevir (SCH 900518): A Potent, Second Generation HCV NS3 Serine Protease InhibitorArasappan, Ashok; Bennett, Frank; Bogen, Stephane L; Venkatraman, Srikanth; Blackman, Melissa; Chen, Kevin X; Hendrata, Siska; Huang, Yuhua; Huelgas, Regina M; Nair, Latha; Padilla, Angela I; Pan, Weidong; Pike, Russell; Pinto, Patrick; Ruan, Sumei; Sannigrahi, Mousumi; Velazquez, Francisco; Vibulbhan, Bancha; Wu, Wanli; Yang, Weiying; Saksena, Anil K; Girijavallabhan, Viyyoor; Shih, Neng-Yang; Kong, Jianshe; Meng, Tao; Jin, Yan; Wong, Jesse; McNamara, Paul; Prongay, Andrew; Madison, Vincent; Piwinski, John J; Cheng, Kuo-Chi; Morrison, Richard; Malcolm, Bruce; Tong, Xiao; Ralston, Robert; Njoroge, F. George
ACS medicinal chemistry letters, 05/2010, Volume: 1, Issue: 2Journal Article
Boceprevir (SCH 503034), 1, a novel HCV NS3 serine protease inhibitor discovered in our laboratories, is currently undergoing phase III clinical trials. Detailed investigations toward a second generation protease inhibitor culminated in the discovery of narlaprevir (SCH 900518), 37, with improved potency (∼10-fold over 1), pharmacokinetic profile and physicochemical characteristics, currently in phase II human trials. Exploration of synthetic sequence for preparation of 37 resulted in a route that required no silica gel purification for the entire synthesis.
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