ChemicalBook > CAS DataBase List > Vaniprevir

Vaniprevir

Product Name
Vaniprevir
CAS No.
923590-37-8
Chemical Name
Vaniprevir
Synonyms
MK 7009;Vaniprevir;MK 7009/Vaniprevir;Vaniprevir(MK-7009);MK-7009;MK7009;MK 7009;(1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone;Cyclopropanecarboxamide, N-[[[6-(2-carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethyl-, (1→2)-lactone, (1R,2R)-
CBNumber
CB82509978
Molecular Formula
C38H55N5O9S
Formula Weight
757.94
MOL File
923590-37-8.mol
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Vaniprevir Property

Melting point:
175-177 °C
Density 
1.33
storage temp. 
Store at -20°C
solubility 
Soluble in DMSO
form 
Powder
pka
4.58±0.40(Predicted)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P314Get medical advice/attention if you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0006862
Product name
MK-7009
Purity
95.00%
Packaging
5MG
Price
$496.28
Updated
2021/12/16
ApexBio Technology
Product number
A3908
Product name
Vaniprevir
Packaging
5mg
Price
$537
Updated
2021/12/16
Biorbyt Ltd
Product number
orb611703
Product name
Vaniprevir
Packaging
10mg
Price
$615.4
Updated
2021/12/16
ApexBio Technology
Product number
A3908
Product name
Vaniprevir
Packaging
10mg
Price
$750
Updated
2021/12/16
DC Chemicals
Product number
DC23925
Product name
Vaniprevir
Purity
>98%
Packaging
10mg
Price
$400
Updated
2021/12/16
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Vaniprevir Chemical Properties,Usage,Production

Description

Vaniprevir, which was approved in Japan in 2014 and sold under the trade name Vanihep®, is one of several structurallyrelated macrocycles developed for the treatment of patients afflicted with the hepatitis C virus. Specifically, the drug is indicated for patients with untreated, interferon-unresponsive, or relapsed genotype 1 chronic hepatitis C. Similar to asunaprevir (IV), vaniprevir is a NS3/4A protease inhibitor, and thus has a comparable mechanism of action.

Uses

Vaniprevir is an antiviral therapy against hepatitis C.

Synthesis

Beginning with commercial bis-benzylbromide 311, subjection to benzylamine under basic conditions followed by acidification afford the isoindoline as the toluene sulfonic acid salt 312. This salt was then freebased and acylative removal of the benzyl protecting group took place through the use of acetyl chloride. Hydrochloric acid in refluxing methanol removed the acetamide to liberate indoline 313, which was isolated as the HCl salt. Next, exposure of 313 to alcohol 314 in the presence of CDI and warm DMF gave rise to carbamate 315. This was followed by Heck installation of n-hexenyl fragment 316 and subsequent hydrogenation of the olefin with concomitant removal of the benzoyl carbamate protecting group delivered macrocycle precursor 317. Next, an intramolecular lactamization reaction furnished the macrocyclic system and this was followed by saponification of the prolinate ester to give 318. This acid was then coupled with cyclopropylamine 319 under standard coupling conditions to furnish vaniprevir in 87% yield.
The preparation of hexenyl fragment 316 started with the lithiation of commercially available ethyl isobutyrate (320) and alkylative quench with 1-bromo-4-butene to provide hexenyl ester 321. Next, DIBAL reduction followed by CDI-mediated carbamate formation with L-t-leucine and subsequent treatment with dicyclohexylamine (DCHA) furnished the key hexenyl fragment 316.

The assembly of cyclopropylamine 319 stems from cyclopropyl fragment 34, whose synthesis was described in Scheme 5. Hydrogenation of this system to saturate the double bond was followed by treatment with toluenesulfonic acid to remove the Boc group, furnishing the tosylate salt in good yield for the two step sequence.

Vaniprevir Preparation Products And Raw materials

Raw materials

Preparation Products

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Vaniprevir Suppliers

Chembest Research Laboratories Limited
Tel
021-20908456
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021-58180499
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sales@BioChemBest.com
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China
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Haoyuan Chemexpress Co., Ltd.
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021-58950125
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(86) 21-58955996
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China
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61
Shanghaizehan biopharma technology co., Ltd.
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021-61350662
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sales@zehanbiopharma.com
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SPIRO PHARMA
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Guangzhou QiYun Biotechnology Co., Ltd.
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Chengdu Dianchun Technology Co., Ltd
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400-1166-196 18502815961
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QQ:800101999
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China
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ShangHai Biochempartner Co.,Ltd
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17754423994 17754423994
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Amadis Chemical Company Limited
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Lynnchem
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Hubei Hongxin Ruiyu Fine Chemical Co., Ltd.
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Shanghai Biopharmaleader Co., Ltd.
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Shaanxi Jiandu Pharmaceutical Chemical Co. Ltd.
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Fan De(Beijing) Biotechnology Co., Ltd.
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Hangzhou Synstar pharmaceutical Technology CO.,Ltd
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Xi'an MC Biotech, Co., Ltd.
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Baoji Guokang Bio-Technology Co., Ltd.
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DC Chemicals
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Chongqing Chemdad Co., Ltd
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CONIER CHEM AND PHARMA LIMITED
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Absin Bioscience Inc.
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MedBioPharmaceutical Technology Inc
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View Lastest Price from Vaniprevir manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Vaniprevir 923590-37-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Vaniprevir 923590-37-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09
Career Henan Chemical Co
Product
MK 7009 923590-37-8
Price
US $1.00/KG
Min. Order
1G
Purity
98%
Supply Ability
100KG
Release date
2018-08-21

923590-37-8, VaniprevirRelated Search:


  • MK 7009/Vaniprevir
  • Vaniprevir(MK-7009)
  • MK 7009
  • Vaniprevir
  • (1R,2R)-N-[[[6-(2-Carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethylcyclopropanecarboxamide (1-2)-lactone
  • MK-7009;MK7009;MK 7009
  • Cyclopropanecarboxamide, N-[[[6-(2-carboxy-2,3-dihydro-1H-isoindol-4-yl)-2,2-dimethylhexyl]oxy]carbonyl]-3-methyl-L-valyl-(4R)-4-hydroxy-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethyl-, (1→2)-lactone, (1R,2R)-
  • 923590-37-8
  • C38H55N5O9S
  • API