cas 402958-98-9, Des[N-[(1S)-1-[2-(cyclopropylaMino)-2-oxoacetyl]butyl]carboxaMido] 1-Carboxy Telaprevir | Articles data ｜lookchem

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402958-98-9

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PROCESS FOR THE SYNTHESIS OF TELAPREVIR, OR PHARMACEUTICALLY ACCEPTABLE SALTS OR SOLVATES AS WELL AS INTERMEDIATE PRODUCTS THEREOF
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.
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Page/Page column 26

(2013/09/26)

Processes and intermediates
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.
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Page/Page column 21; 48

(2010/11/26)

P4 and P1′ optimization of bicycloproline P2 bearing tetrapeptidyl α-ketoamides as HCV protease inhibitors
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.
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)

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Chemical Properties

Boiling Point: 817.7±65.0 °C at 760 mmHg
Flash Point:448.3±34.3 °C
Density: 1.2±0.1 g/cm³
Solubility:DMSO (Slightly), Methanol (Slightly)
Storage Temp.:Refrigerator
PKA: 3.34±0.20(Predicted)
PSA: 148.57000
LogP: 3.75090

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