1377049-84-7

Basic information

• Product Name: Velpatasvir
• Synonyms: Velpatasvir;velpatasvir(GS-5816);methyl ((2s)-1-((2s,5s)-2-(9-(2-((2s,4s)-1-((2r)-2-((methoxycarbonyl)amino)-2-phenylacetyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1h-imidazol-5-yl)-1,11-dihydroisochromeno(4',3':6,7)naphtho(1,2-d)imidazol-2-yl)-5-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate;Velpatasvir API;Unifiram (DM-232);Methyl [(2S)-1-[(2S,5S)-2-[9-[2-[(2S,4S)-1-[(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl]-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-y;MFCD28411371;Product:Velpatasvir
• CAS NO: 1377049-84-7
• Molecular Formula: C₄₉H₅₄N₈O₈
• Molecular Weight: 883.00186
• EINECS: 1592732-453-0
• Mol File: 1377049-84-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.314±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (>25 mg/ml)
• PKA: 10.75±0.46(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: Velpatasvir(CAS DataBase Reference)
• NIST Chemistry Reference: Velpatasvir(1377049-84-7)
• EPA Substance Registry System: Velpatasvir(1377049-84-7)

Safety Data

• Hazardous Substances Data: 1377049-84-7(Hazardous Substances Data)

Usage

Description

Velpatasvir (1377049-84-7) is an extremely potent pan-genotypic hepatitis C virus (HCV) NS5A inhibitor.1 It is a component of Epclusa? and Vosevi?, two clinically useful medications with 98% and 97%, respectively, cure rates for HCV.? It displayed EC50’s for GTs 1-4, 6a ranging from 6-16 pM, GT5a at 75 pM, and GT6e at 130 pM. Velpatasvir also displayed an excellent barrier to viral resistance. It has been shown in silico, that velpatasvir binds to the SARS-CoV-2 spike protein and may be a potential therapeutic.2

Uses

Velpatasvir is a NS5A inhibitor in patients with hepatitis C (HCV) infection.

Definition

ChEBI: A complex organic heteropentacyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with sofosbuvir (under the brand name Epclusa) for treatment of patients with chronic hepatitis C of all six major genotypes.

References

Link et al. (2019), Discovery of velpatasvir (GS-5816): A potent pan-genotypic HCV NS5A inhibitor in the single-tablet regimens Vosevi? and Epclusa?; Bioorg. Med. Chem. Lett., 29 2415 Kadioglu et al. (2020), Identification of novel compounds against three targets of SARS CoV-2 coronavirus by combined virtual screening and supervised machine learning; Comput. Biol. Med. 133 104359

Upstream product

• 1377604-63-1 methyl {(1R)-2-[(2S,4S)-2-(5-{2-[(2S,5S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-5-methylpyrrolidin-2-yl]-1,4,5,11-tetrahydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate 
• 334769-80-1 (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 676560-83-1 (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 676560-84-2 (2S,5S)-5-methylpyrrolidine-2-carboxylic acid ethyl ester 
• 896733-29-2 (S)-5-methyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester 
• 913251-58-8 (S)-2-(tert-butoxycarbonylamino)-5-oxohexanoic acid ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 1378392-91-6 (2S,5S)-1-tert-butyl 2-(3-chloro-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-9-yl)-5-methylpyrrolidine-1,2-dicarboxylate 
• 1844064-96-5 (2S,4S)-2-[5-(2-{(2S,4S)-1-{N-(methoxycarbonyl)-L-valyl}-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromene[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine 
• 50890-96-5 (2R)-2-[(methoxycarbonyl)amino]-2-phenylacetic acid 
• 1378392-97-2 methyl [(2S)-3-methyl-1-{(2S,5S)-2-methyl-5-[9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl]pyrrolidin-1-yl}-1-oxobutan-2-yl]carbamate 
• 1378392-94-9 (2S,5S)-tert-butyl 2-(9-chloro-5H-naphtho[c,g]chromeno[8,9-d]imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate 
• 1378392-93-8 (2S,5S)-tert-butyl 2-(9-chloro-4,5-dihydro-5H-naphtho[c,g]chromeno[8,9-d]imidazol-2-yl)-5-(methyl)pyrrolidine-1-carboxylate 
• 1378392-96-1 methyl {(2S)-1-[(2S,5S)-2-(9-chloro-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate 

Relevant articles and documents

Method for preparing NS5A inhibitor-Velpatasvir

The invention discloses a method for preparing an NS5A inhibitor-Velpatasvir, wherein the method mainly comprises the five steps: 1) carrying out docking reaction on reaction initial raw materials VPM1, VPM2 and VPM3 under the catalytic action of alkali to prepare an intermediate VP1; 2) removing amino protecting groups from the intermediate VP1 by using a protecting group removing reagent to prepare an intermediate VP2; 3) carrying out cyclization on the intermediate VP2 and an amine compound to prepare an intermediate VP3; 4) carrying out a reaction on the intermediate VP3 with VPM4 under the action of a condensing agent to prepare an amide compound intermediate VP4; and 5) carrying out oxidation reaction on the intermediate VP4 under the action of an oxidizing agent to prepare Velpatasvir. The preparation process of Velpatasvir has the characteristics of simplified route, simple reaction conditions, enhanced operability and higher product yield, and is more suitable for large-scaleindustrial production.

Compound used for inhibiting hepatitis C virus, and pharmaceutical applications thereof

The invention relates to a compound which is represented by formula I, is used for inhibiting hepatitis C virus, and possesses excellent bioavailability, and a nontoxic pharmaceutically acceptable salt thereof. The compound possesses extremely high inhibition effect on HCV of all genotypes. In the formula I, R is used for representing hydrogen atom, glycyl, L-alanyl, L-leucyl, L-valyl, or L-isoleucyl.

Preparation of velpatasvir and derivatives thereof

The invention relates to a preparation method of velpatasvir and derivatives thereof. Concretely, the preparation method provided by the invention comprises the step of preparing the velpatasvir and derivatives thereof (definitions of all the groups are described in the specification) by virtue of an intermediate compound shown in a formula. The preparation method provided by the invention has the advantages that byproducts are fewer, cost is low, and the preparation method is applicable to industrial production of velpatasvir. (The formula is described in the specification.).