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ソホスブビル

 ソホスブビル 化学構造式
1190307-88-0
CAS番号.
1190307-88-0
化学名:
ソホスブビル
别名:
ソホスブビル;ソホスブビル;ソフォスブビル;ソホスブビル (JAN)
英語化学名:
Sofosbuvir
英語别名:
GS-7977;PSI 7977;Sofesbuvir;Sofosbubir;sofosbuvir;Suofeibuwei;Sophy Bouvet;Sofosbuvir (W.S);Sofosbuvir, >=98%;Sofosbuvir,GS-7977
CBNumber:
CB02604350
化学式:
C22H29FN3O9P
分子量:
529.45
MOL File:
1190307-88-0.mol

ソホスブビル 物理性質

比重(密度) :
1.41
酸解離定数(Pka):
9.39±0.10(Predicted)
CAS データベース:
1190307-88-0

安全性情報

HSコード  29339900
有毒物質データの 1190307-88-0(Hazardous Substances Data)

ソホスブビル 価格

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入

ソホスブビル 化学特性,用途語,生産方法

用途

ソホスブビル(Sofosbuvir)はC型肝炎ウイルス(HCV)感染症の治療薬として使用されるヌクレオチドアナログの一つである。ウイルスのNS5Bポリメラーゼを阻害する。商品名ソバルディ。 単剤(ソバルディ):セログループ2(ジェノタイプ2)のC型慢性肝炎またはC型代償性肝硬変におけるウイルス血症の改善。

効能

抗ウイルス薬, NS5Bポリメラーゼ阻害薬

商品名

ソバルディ (ギリアド・サイエンシズ)

説明

Sofosbuvir is a drug used for the treatment of hepatitis C. It is recommended to be used in combination with other drugs (such as velpatasvir) for the first-line treatment for HCV genotypes 1, 2, 3, 4, 5, and 6. It takes effect through acting as a nucleotide analog inhibitor, being capable of specially inhibiting the HCV NS5B (non-structural protein 5B) RNA-dependent RNA polymerase.

Originator

Pharmasset (United States)

使用

PSI-7977 is a prodrug that is metabolized to the active antiviral agent 2''-deoxy-2''-α-fluoro-β-C-methyluridine-5''-monophosphate and is currently being investigated in phase 3 clinical trials for the treatment of hepatitis C. Studies have profiled PSI-7977 as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase.

使用

PSI-7977 is a phosphoramidate prodrug of PSI-7851, a nucleoside analog that, when phosphorylated, inhibits the RNA-dependent RNA polymerase of hepatitis C virus (EC50 = 92 nM). PSI-7977 is effective in vitro and in vivo.[Cayman Chemical]

使用

PSI-7977 is a prodrug that is metabolized to the active antiviral agent 2'-deoxy-2'-α-fluoro-β-C-methyluridine-5'-monophosphate and is currently being investigated in phase 3 clinical trials for the t reatment of hepatitis C. Studies have profiled PSI-7977 as a nucleotide inhibitor of hepatitis C virus, exerting selective inhibitory effects towards HCV NS5B polymerase.

定義

ChEBI: A nucleotide conjugate that is used in combination with ledipasvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.

brand name

Sovaldi

臨床応用

In December 2013, sofosbuvir (also known as GS-7977 and PSI-7977) was approved in the United States for the treatment of hepatitis C virus (HCV) infection as a component of a combination antiviral treatment regimen. Sofosbuvir was discovered from an effort to enhance the activity of the parent nucleoside by bypassing rate-limiting monophosphorylation with a prodrug that would liberate the intactmonophosphate in the liver, where it would then be converted by cellular kinases to the active triphosphate species. In addition, the prodrug was designed to be amenable to oral delivery. In the initial synthesis of sofosbuvir, the iso-propyl ester of (L)-alanine was coupled with phenyl dichlorophosphate to provide a diastereomeric intermediate that was coupled with the uridine nucleoside. The diastereomeric mixture (GS-9851) was shown to produce high levels of triphosphate in vitro in primary hepatocytes and in the livers of rats, dogs, and monkeys after oral dosing. The individual diastereomers were obtained by chromatography or by crystallization. The diastereomer with the Sp configuration at the phosphorous center (sofosbuvir) was found to be >10-fold more potent in an HCV replicon assay than the corresponding Rp diastereomer (EC90s of 0.42 and 7.5 μM, respectively).

Chemical Synthesis

The enantiopure unsaturated ester 166, which readily arises from olefination of the commercially-available aldehyde 165, was subjected to ethylene glycol-promoted permanganate dihydroxylation conditions to afford diol 167 in 60% yield over the two steps. A three-step sequence was then employed to generate lactone 169. Diol 167 was converted to the cyclic sulfite and then oxidized with bleach to give the corresponding cyclic sulfate. Treatment with nucleophilic fluorine gave intermediate ammonium sulfonate 168, which, upon acidic hydrolysis of both the acetonide and sulfonate, underwent cyclization to give lactone 169. Next, bis-protection of diol 169 furnished 170 in 71% yield for the four-step sequence. Reduction and chlorination through the use of Red-Al ® and sulfuryl chloride, respectively, constructed chlorotetrahydrofuran 171, which was subsequently reacted with commercial N-(2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 172 in the presence of base and Lewis acid to afford 173 in 57% yield over the two steps. Treatment of 173 with AcOH and then ammonia in MeOH removed all benzoyl protection to give rise to diol 174 in 78% yield. Finally, treatment of 174 with pentafluorophenolic phosphonate ester 175 and tert-butylmagnesium chloride generated sofosbuvir (XXII) in 68% yield. The final step proceeds with excellent chirality transfer from 175 (99.7% ee). Notably, the preparation of the key phosphonate fragment was achieved in a simple two-step sequence beginning with alanine isopropyl ester 176. Phosphorylation in the presence of base at cryogenic temperatures, followed by treatment with pentafluorophenol, delivered scale quantities of 176 in 34% isolated yield and high enantiopurity (>98% ee) after recrystallization.

ソホスブビル 上流と下流の製品情報

原材料

準備製品


ソホスブビル 生産企業

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1190307-88-0( ソホスブビル)キーワード:


  • 1190307-88-0
  • (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-Methyltetrahydrofuran-2-yl)Methoxy)(phenoxy)phosphoryl)aMino)propanoate
  • PSI-7977 Discontinued
  • L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-uridylyl]-, 1-Methylethyl ester
  • Sophy Bouvet
  • Sofosbuvir and intermediates
  • Sofosbuvir1190307-88-0
  • Isopropyl (2S)-2-{[(S)-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-4-fluoro-3-hydroxy-4-methyltetrahydro-2-furanyl]methoxy}(phenoxy)phosphoryl]amino}propanoate
  • PSI-7977;GS-7977;PSI 7977;GS 7977;SOFOSBUVIR
  • PSI-7977;GS-7977;PSI 7977;GS 7977
  • 1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  • propan-2-yl (2S)-2-[[[(2R,3R,4R,5S)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
  • Sofosbuvir (W.S)
  • Sofesbuvir
  • Sofosbuvir (PSI-7977, GS-7977)
  • Sofosbuvir N-[[P(S),2'R]-2'-Deoxy-2'-fluoro-2'-methyl-P-phenyl-5'-uridylyl]-L-alanine 1-methylethyl ester
  • propan-2-yl (2S)-2-[[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
  • Suofeibuwei
  • Sofosbuvir, >=98%
  • Sofosbubir
  • Sofosbuvir,GS-7977
  • (S)-Isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-h
  • sofosbuvir, PSI7977
  • GS-7977
  • N-[[P(S),2'R]-2'-Deoxy-2'-fluoro-2'-methyl-P-phenyl-5'-uridylyl]-L-alanine 1-methylethyl ester
  • PSI 7977
  • sofosbuvir
  • GS-7977/sofosbuvir
  • Sofosbuvir fandachem
  • PSI-7977 fandachem
  • isopropyl ((((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
  • ソホスブビル
  • ソホスブビル
  • ソフォスブビル
  • ソホスブビル (JAN)
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