402959-36-8Relevant articles and documents
Asymmetric synthesis of 3,4-disubstituted proline derivatives: Application in synthesis of hepatitis C virus protease inhibitor telaprevir
Zhang, Fan,Wen, Xiaoan,Xu, Qing-Long,Sun, Hongbin
, p. 8101 - 8109 (2015/02/02)
A practical asymmetric synthesis of 3,4-disubstituted proline derivatives has been realized with high stereoselectivity and moderate yield. The key steps involved are desymmetric ring-opening reaction of commercially available anhydrides, intramolecular Strecker reaction and thermodynamically controlled cyanide hydrolysis. Based on this methodology, the synthesis of HCV protease inhibitor Telaprevir was achieved.
PROCESS FOR THE PREPARATION OF TELAPREVIR AND ITS INTERMEDIATES
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, (2015/01/07)
The present invention provides a process for the preparation of telaprevir and its intermediates.
PROCESS FOR THE PREPARATION OF TELAPREVIR AND INTERMEDIATES THEREOF
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, (2015/01/07)
The present invention provides a process for the preparation of telaprevir and intermediates thereof.
PROCESS FOR THE SYNTHESIS OF TELAPREVIR, OR PHARMACEUTICALLY ACCEPTABLE SALTS OR SOLVATES AS WELL AS INTERMEDIATE PRODUCTS THEREOF
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, (2013/09/26)
The invention relates to a process for the preparation of telaprevir, or a pharmaceutically acceptable salt or solvate thereof, wherein the process requires a smaller number of process steps and/or does not require the use of toxic and instable compounds compared to the known processes. Another embodiment refers to telaprevir, or a pharmaceutically acceptable salt or solvate thereof as well as to intermediate products for preparation of the same, wherein the afore-mentioned products are obtained by the process described herein.
A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions
Znabet, Anass,Polak, Marloes M.,Janssen, Elwin,De Kanter, Frans J. J.,Turner, Nicholas J.,Orru, Romano V. A.,Ruijter, Eelco
supporting information; experimental part, p. 7918 - 7920 (2010/12/19)
A very short and efficient synthesis of the important drug candidate telaprevir, featuring a biocatalytic desymmetrization and two multicomponent reactions as the key steps, is presented. The classical issue of lack of stereoselectivity in Ugi- and Passerini-type reactions is circumvented. The atom economic and convergent nature of the synthetic strategy require only very limited use of protective groups.
Processes and intermediates
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Page/Page column 21; 49, (2010/11/26)
The invention relates to compounds and processes useful for the preparation of protease inhibitors, particularly serine protease inhibitors. The protease inhibitors are useful for treatment of HCV infections.
P4 and P1′ optimization of bicycloproline P2 bearing tetrapeptidyl α-ketoamides as HCV protease inhibitors
Yip, Yvonne,Victor, Frantz,Lamar, Jason,Johnson, Robert,Wang, Q. May,Glass, John I.,Yumibe, Nathan,Wakulchik, Mark,Munroe, John,Chen, Shu-Hui
, p. 5007 - 5011 (2007/10/03)
We describe herein the design, synthesis, and antiviral activity of a series of P4 modified tetrapeptidyl α-ketoamides as HCV protease inhibitors. The most promising analog identified through this SAR, 5a, 5c, and 5e demonstrated excellent enzyme inhibitory potency, enzyme selectivity, cellular activity, and acceptable therapeutic indexes. With the aim of improving HCV protease inhibitors reported in our previous manuscripts, we synthesized and evaluated a series of 1a-based tetrapeptidyl α-ketoamides with additional P4 modification. The promising analog discovered through this SAR, 5a, was further derivatized at P1′ or P1 position. As a result of these efforts, we found that replacement of the P4 valine as seen in 1a with cyclohexylglycine (Chg) resulted in the discovery of 5a, 5c, and 5e endowed with improved cellular activity in comparison to 1a.
