- Stereoselective synthesis of β-amino acids by aldol-type addition
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A synthesis of α-oxygenated β-amino acid derivatives using an aldol-type addition is described. Depending on the enol equivalent different oxidation states of the oxygen substituent are accessible, while choosing a chiral imine allows to generate the aldol product in a stereoselective manner. This methodology has been applied to the synthesis of the biologically active compound Telaprevir, used in the traetment of hepatitis C.
- Benito-Garagorri, David,Felzmann, Wolfgang,Nerdinger, Sven,Hoferl-Prantz, Kathrin
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p. 299 - 311
(2020/01/31)
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- Ugi and Passerini reactions of biocatalytically derived chiral aldehydes: Application to the synthesis of bicyclic pyrrolidines and of antiviral agent telaprevir
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Lipase mediated desymmetrization of a meso-diol (1,2-cyclopentanedimethanol) allows the synthesis of both enantiomers of some chiral aldehydes, whose behavior in Passerini and Ugi reactions has been explored. Exploiting these two complementary multicomponent reactions and coupling them with a subsequent cyclization process, we observed that 6 out of all 8 possible stereoisomers of peptidomimetic pyrrolidines can be obtained in good yields. The potential of these protocols has been proved by the development of a new efficient synthesis of antiviral drug telaprevir.
- Moni, Lisa,Banfi, Luca,Basso, Andrea,Carcone, Luca,Rasparini, Marcello,Riva, Renata
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p. 3411 - 3428
(2015/04/22)
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- PROCESS FOR THE PREPARATION OF TELAPREVIR AND ITS INTERMEDIATES
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The present invention provides a process for the preparation of telaprevir and its intermediates.
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Page/Page column 15
(2015/01/07)
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- PROCESS FOR THE PREPARATION OF TELAPREVIR AND INTERMEDIATES THEREOF
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The present invention provides a process for the preparation of telaprevir and intermediates thereof.
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Page/Page column 20
(2015/01/07)
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- Asymmetric synthesis of 3,4-disubstituted proline derivatives: Application in synthesis of hepatitis C virus protease inhibitor telaprevir
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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.
- Zhang, Fan,Wen, Xiaoan,Xu, Qing-Long,Sun, Hongbin
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p. 8101 - 8109
(2015/02/02)
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- SYNTHESIS OF A VIRAL PROTEASE INHIBITOR
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Disclosed is a process for the preparation of telaprevir of formula (I) or a salt thereof, comprising the oxidation reaction of a compound of formula (II) or a salt thereof, (II) wherein said oxidation is conducted in a solvent in the presence of a supported oxidising agent.
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Page/Page column 10; 11
(2014/01/08)
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- PROCESS FOR THE SYNTHESIS OF TELAPREVIR, OR PHARMACEUTICALLY ACCEPTABLE SALTS OR SOLVATES AS WELL AS INTERMEDIATE PRODUCTS THEREOF
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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 27-28
(2013/09/26)
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- SYNTHESIS OF TELAPREVIR AND BOCEPREVIR, OR PHARMACEUTICALLY ACCEPTABLE SALTS OR SOLVATES AS WELL AS INTERMEDIATE PRODUCTS THEREOF INCLUDING ?-AMINO ACIDS PREPARED VIA MUKAIYAMA ALDOL ADDITION
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The invention relates to synthetic routes for preparing telaprevir and boceprevir, and its intermediates as well as peptides other than telaprevir. The synthetic routes are based on a Mukaiyama aldol addition reaction of a silyl enol ether or an enolate with an imine. The invention also refers to novel intermediates for preparing telaprevir/boceprevir or other peptides.
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Page/Page column 48
(2014/01/09)
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- A PROCESS FOR THE PREPARATION OF SUBSTITUTED PROLYL PEPTIDES AND SIMILAR PEPTIDOMIMETICS
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The present invention relates to a process for the stereoselective preparation of a compound having the general formula (I) or its respective diastereomers: comprising reacting a compound having the general formula (II) or its diastereomers: with a compound of the general formula III: R3-COOH and a compound of the general formula IV: R4-NC wherein R1 represents each independently, or jointly a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R2 represents a hydrogen atom, a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R3 represents a substituted or unsubstituted alkyl, alkenyl, or alkynyl, or an aromatic or non-aromatic aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure.
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Page/Page column 50; 51
(2011/09/21)
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- A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions
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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.
- Znabet, Anass,Polak, Marloes M.,Janssen, Elwin,De Kanter, Frans J. J.,Turner, Nicholas J.,Orru, Romano V. A.,Ruijter, Eelco
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supporting information; experimental part
p. 7918 - 7920
(2010/12/19)
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- Deuterated hepatitis C protease inhibitors
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A deuterated α-ketoamido steric specific compound of the formula wherein D denotes a deuterium atom on a steric specific carbon atom.
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Page/Page column 21
(2010/11/28)
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- Processes and intermediates
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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; 49-50
(2010/11/26)
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