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レジパスビル

レジパスビル 化学構造式
1256388-51-8
CAS番号.
1256388-51-8
化学名:
レジパスビル
别名:
レジパスビル
英語化学名:
Ledipasvir
英語别名:
GS 588;GS5885;CS-948;GS 5885;GS-5885;Ledipasvir;Leidipawei;gs-5885/gs5885;Ledipasvir API;HY-15602 (GS-5885
CBNumber:
CB52666650
化学式:
C49H54F2N8O6
分子量:
889
MOL File:
1256388-51-8.mol

レジパスビル 物理性質

比重(密度) :
1.42±0.1 g/cm3(Predicted)
酸解離定数(Pka):
11.20±0.10(Predicted)

安全性情報

Sフレーズ  24/25
RIDADR  3077
HSコード  29333990

レジパスビル 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

レジパスビル 化学特性,用途語,生産方法

用途

レジパスビル(Ledipasvir)はC型肝炎ウイルス)(HCV)のNS5A(英語版)阻害効果を持つ化合物である。レジパスビルとソホスブビルを組み合わせて投与すると、HCV複製の直接的阻害効果を示し、インターフェロンまたはリバビリンを併用することなく、ジェノタイプ1aまたは1bのC型肝炎を治療することができる。

効能

抗ウイルス薬, NS5A阻害薬

説明

Ledipasvir is a potent NS5A inhibitor that is approved for use in combination with sofosbuvir, a nucleotide inhibitor of viral polymerase, for the treatment of chronic hepatitis C virus genotype 1 infection. This combination was discovered and developed at Gilead Sciences and is marketed as the fixed combination with brand name of Harvoni.

定義

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

Chemical Synthesis

The synthesis of the spirocyclopropane proline intermediate 136 is described in Scheme above. Bis-iodination of cyclopropane-1,1-diyldimethanol (131) in the presence of triphenylphosphine gave diiodide 132 in 70% yield. N-Boc-glycine ethyl ester (133) was then treated with sodium hydride followed by diiodide 132 to give the protected proline analog 134 in 61% yield. Saponification of the ester followed by a classical resolution with (1S,2R)-amino-indanol gave enantomerically pure salt 135. Liberation of the free acid with 1 M HCl followed by treatment with potassium tert-butoxide provided enantiopure potassium salt 136 in high yield.

Iodination of 2-bromofluorene (137) produced aryl iodide 138 in 95% yield, which was then treated with lithium hexamethyldisilazide and N-fluorobenzenesulfonimide (NFSI) to give the difluoro intermediate 139 in 82% yield. Formation of the Grignard reagent of 139 through reaction with isopropylmagnesium chloride followed by condensation with Weinreb amide 140 gave chloroketone 141 in 71% yield. The potassium salt of the cyclopropyl proline intermediate 136 was coupled with 141 to give keto ester 142 in high yield. Heating 142 with ammonium acetate resulted in formation of the imidazole ring in intermediate 143 in 77% yield.
QQ截图20210204152749.jpg
Commercially available (1R,3S,4S)-N-Boc-2-azabicyclo [2.2.1]heptane-3-carboxylic acid (144) was coupled to 4-bromo- 1,2-benzenediamine (145) using EDC/HOBt to give a mixture of amides 146a/146b in 72% yield. Heating mixture 146a/146b with acetic acid affected cyclization to benzimidazole 147 in 94% yield. Palladium mediated coupling of bromide 147 to bis(pinacolato)diboron gave intermediate 148 which was then coupled in the same reaction vessel to bromide 143. This was followed by formation of the oxalate salt to give the protected central core of ledipasvir (149) in good overall yield. Removal of the amine protecting groups gave diamine 150 which was coupled to two equivalents of Moc-valine (151) via EDC/HOBt to give ledipasvir XVII in 73% yield.
QQ截图20210204152830.jpg

レジパスビル 上流と下流の製品情報

原材料

準備製品


レジパスビル 生産企業

Global( 207)Suppliers
名前 電話番号 ファックス番号 電子メール 国籍 製品カタログ 優位度
Casorganics US Corp
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Beijing Cooperate Pharmaceutical Co.,Ltd
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Hangzhou FandaChem Co.,Ltd.
008615858145714
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PI & PI BIOTECH INC.
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ATK CHEMICAL COMPANY LIMITED
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Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 968 58

1256388-51-8(レジパスビル)キーワード:


  • 1256388-51-8
  • GS 5885
  • GS5885
  • GS-5885
  • Ledipasvir
  • GS-5885/Ledipasvir
  • gs-5885/gs5885
  • Ledipasvir / GS 5885
  • GS 588
  • HY-15602 (GS-5885
  • Solid dispersion of ledipasvir
  • Ledipasvir (API, Amorphous)
  • Ledipasvir: copovidone solid dispersion 1:1
  • N-[(1S)-1-[[(6S)-6-[5-[9,9-difluoro-7-[2-[(1R,3S,4S)-2-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-2-azabicyclo[2.2.1]hept-3-yl]-1H-benzimidazol-6-yl]-9H-fluoren-2-yl]-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl]carbonyl]-2-methylpropyl]-carbamic acid methyl ester
  • Leidipawei
  • N-[(1S)-1-[[(6S)-6-[5-[9,9-difluoro-7-[2-[(1R,3S,4S)-2-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxoButyl]-2-azabicyclo[2.2.1]hept-3-yl]-1H-benzimidazol-6-yl]-9H-fluoren-2-yl]-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl]carbonyl]-2-methylpropyl]-carbamic
  • Ledipasvir API
  • N-[(1S)-1-[[(6S)-6-[5-[9,9-Difluoro-7-[2-[(1R,3S,4S)-2-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-2-azabicyclo[2.2.1]hept-3-yl]-1H-benzimidazol-6-yl]-9H-fluoren-2-yl]-1H-imidazol-2-yl]-5-azaspi
  • Ledipasvir, 98%, HCV NS5A polymerase inhibitor
  • GS 5885;GS-5885;GS5885
  • CS-948
  • Carbamic acid, N-[(1S)-1-[[(6S)-6-[5-[9,9-difluoro-7-[2-[(1R,3S,4S)-2-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-2-azabicyclo[2.2.1]hept-3-yl]-1H-benzimidazol-6-yl]-9H-fluoren-2-yl]-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl]carbonyl]-2-methylpropyl]-, methyl ester
  • Ledipasvir Intermediate fandachem
  • Ledipasvir fandachem
  • Ledipasvir (10mM in DMSO)
  • レジパスビル
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