902148-54-3Relevant academic research and scientific papers
The First Kilogram Synthesis of Beclabuvir, an HCV NS5B Polymerase Inhibitor
Bien, Jeffrey,Davulcu, Akin,Delmonte, Albert J.,Fraunhoffer, Kenneth J.,Gao, Zhinong,Hang, Chao,Hsiao, Yi,Hu, Wenhao,Katipally, Kishta,Littke, Adam,Pedro, Aghogho,Qiu, Yuping,Sandoval, Maria,Schild, Richard,Soltani, Michelle,Tedesco, Anthony,Vanyo, Dale,Vemishetti, Purushotham,Waltermire, Robert E.
, p. 1393 - 1408 (2018/09/06)
The process development and kilogram-scale synthesis of beclabuvir (BMS-791325, 1) is described. The convergent synthesis features the use of asymmetric catalysis to generate a chiral cyclopropane fragment and coupling with an indole fragment via an alkyl
A practical and efficient synthesis of 6-carboalkoxy-13-cycloalkyl-5H- indolo[2,1-a][2]benzazepine-10-carboxylic acid derivatives
Hewawasam, Piyasena,Tu, Yong,Hudyma, Thomas W.,Zhang, Xiaofan,Gentles, Robert G.,Kadow, John F.,Meanwell, Nicholas A.
, p. 1148 - 1153 (2014/02/14)
A convenient and practical synthesis of 6-carboalkoxy-13-cycloalkyl-5H- indolo[2,1-a][2]benzazepine-10-carboxylic acid derivatives (6) has been developed. The key step in the synthesis utilizes an intramolecular tandem reaction sequence of a Michael addition followed by a Horner-Wadsworth-Emmons (HWE) olefination reaction between hemi-aminal 11 and methyl 2-(dimethoxyphosphoryl)acrylate 12. The ring construction occurred efficiently and purification of the products 6 was straightforward. The C-10 methyl ester of 6a was hydrolyzed selectively to the carboxylic acid 13 while the olefin of 6d was converted to the cyclopropane 14 using trimethylsulfoxonium iodide in DMSO in the presence of NaH.
Discovery and preclinical characterization of the cyclopropylindolobenzazepine BMS-791325, a potent allosteric inhibitor of the hepatitis C virus NS5B polymerase
Gentles, Robert G.,Ding, Min,Bender, John A.,Bergstrom, Carl P.,Grant-Young, Katharine,Hewawasam, Piyasena,Hudyma, Thomas,Martin, Scott,Nickel, Andrew,Regueiro-Ren, Alicia,Tu, Yong,Yang, Zhong,Yeung, Kap-Sun,Zheng, Xiaofan,Chao, Sam,Sun, Jung-Hui,Beno, Brett R.,Camac, Daniel M.,Chang, Chong-Hwan,Gao, Mian,Morin, Paul E.,Sheriff, Steven,Tredup, Jeff,Wan, John,Witmer, Mark R.,Xie, Dianlin,Hanumegowda, Umesh,Knipe, Jay,Mosure, Kathy,Santone, Kenneth S.,Parker, Dawn D.,Zhuo, Xiaoliang,Lemm, Julie,Liu, Mengping,Pelosi, Lenore,Rigat, Karen,Voss, Stacey,Wang, Yi,Wang, Ying-Kai,Colonno, Richard J.,Gao, Min,Roberts, Susan B.,Gao, Qi,Ng, Alicia,Meanwell, Nicholas A,Kadow, John F.
, p. 1855 - 1879 (2014/04/03)
Described herein are structure-activity relationship studies that resulted in the optimization of the activity of members of a class of cyclopropyl-fused indolobenzazepine HCV NS5B polymerase inhibitors. Subsequent iterations of analogue design and synthe
Cyclopropyl Fused Indolobenzazepine HCV NS5B Inhibitors
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Page/Page column 50, (2010/09/05)
The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV.
CYCLOPROPYL FUSED INDOLOBENZAZEPINE HCV NS5B INHIBITORS
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Page/Page column 46-47, (2009/06/27)
The invention encompasses compounds of formula (I) as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV
Compounds for the Treatment of Hepatitis C
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Page/Page column 28, (2009/05/28)
The invention encompasses compounds of formula I as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV.
Compounds for the Treatment of Hepatitis C
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Page/Page column 25-26, (2009/05/28)
The invention encompasses compounds of formula I as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV.
Compounds for the Treatment of Hepatitis C
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Page/Page column 30, (2008/12/07)
The invention encompasses compounds of formula I as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV.
Compounds for the Treatment of Hepatitis C
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Page/Page column 20, (2008/12/06)
The invention encompasses compounds of formula I as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV.
Compounds for the Treatment of Hepatitis C
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Page/Page column 39, (2008/12/07)
The invention encompasses compounds of Formula I, pharmaceutically acceptable salts thereof, compositions, and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV.
