(3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate hydrochloride | 923590-83-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate hydrochloride
• 英文别名: (2R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl-4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate hydrochloride；(3S,5R)-5-(methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate hydrochloride；(2S,4R)-2-(methoxycarbonyl)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidinium chloride；(3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindo!e-2-carboxylate hydrochloride；[(3R,5S)-5-methoxycarbonylpyrrolidin-1-ium-3-yl] 4-ethenyl-1,3-dihydroisoindole-2-carboxylate;chloride
• CAS: 923590-83-4
• 化学式: C₁₇H₂₀N₂O₄*ClH
• 分子量: 352.818
• InChiKey: WQDLDNXJJKMMGF-PBCQUBLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  67.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate hydrochloride 、 N-[(hept-6-en-1-yloxy)carbonyl]-3-methyl-L-valine 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到methyl N-[(hept-6-en-1-yloxy)carbonyl]-3-methyl-L-valyl-(4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}-L-prolinate
  参考文献：
  名称：

  Discovery of Vaniprevir (MK-7009), a Macrocyclic Hepatitis C Virus NS3/4a Protease Inhibitor

  摘要：

  A new class of H CV NS3/4a protease inhibitors which contain a P2 to P4 macrocyclic constraint was designed using a molecular-modeling derived strategy. Exploration of the P2 heterocyclic region, the P2 to P4 linker, and the PI side chain of this class of compounds via a modular synthetic strategy allowed for the optimization of enzyme potency, cellular activity, and rat liver exposure following oral closing. These studies led to the identification of clinical candidate 35b (vaniprevir, MK-7009), which is active against both the genotype 1 and genotype 2 NS3/4a protease enzymes and has good plasma exposure and excellent liver exposure in multiple species.

  DOI：

  10.1021/jm9015526
• 作为产物：
  描述：

  (2S,4R)-1-tert-butyl 2-methyl 4-(4-vinylisoindoline-2-carbonyloxy)pyrrolidine-1,2-dicarboxylate 以98.4的产率得到(3R,5S)-5-(methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate hydrochloride
  参考文献：
  名称：

  HCV NS3 protease inhibitors

  摘要：

  本发明涉及公式(I)的大环化合物，它们可用作丙型肝炎病毒（HCV）NS3蛋白酶的抑制剂，其合成以及用于治疗或预防HCV感染的用途。

  公开号：

  US07470664B2

文献信息

• HCV NS3 PROTEASE INHIBITORS
  申请人：Link John O.

  公开号：US20100160403A1

  公开（公告）日：2010-06-24

  The present invention relates to macrocyclic compounds of formula (Ia) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

  本发明涉及式(Ia)的大环化合物，其作为丙型肝炎病毒(HCV)NS3蛋白酶抑制剂具有用途，包括其合成方法以及用于治疗或预防HCV感染的应用。
• HCV NS3 protease inhibitors
  申请人：Holloway Katharine M.

  公开号：US20070027071A1

  公开（公告）日：2007-02-01

  The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

  本发明涉及一种公式（I）的大环化合物，该化合物可用作乙型肝炎病毒（HCV）NS3蛋白酶的抑制剂，其合成以及用于治疗或预防HCV感染的用途。
• Macrocyclic Compounds as Antiviral Agents
  申请人：Crescenzi Benedetta

  公开号：US20090312241A1

  公开（公告）日：2009-12-17

  The present invention relates to macrocyclic compounds of formula (I): wherein W, n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R a , M, Z and ring B are defined herein, and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising them, and their use for the treatment or prevention of infection by hepatitis C virus.

  本发明涉及式（I）的大环化合物：其中W、n、m、R1、R2、R3、R4、R5、Ra、M、Z和环B在此处定义，并其药用盐，包含它们的药物组合物，以及它们用于治疗或预防丙型肝炎病毒感染的用途。
• Hepatitis C virus inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US08163921B2

  公开（公告）日：2012-04-24

  Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  公开了具有一般式的丙型肝炎病毒抑制剂。还公开了包含该化合物的组合物和使用该化合物抑制丙型肝炎病毒的方法。
• Macrocyclic Compounds As Antiviral Agents
  申请人：Di Francesco Maria Emilia

  公开号：US20090258891A1

  公开（公告）日：2009-10-15

  The present invention relates to macrocyclic compounds of formula (I): wherein W, n, R 1 , R a , R b , R 3 , R 4 , M, Z, ring A and ring B are defined herein, and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising them, and their use for the treatment or prevention of infection by hepatitis C virus.

  本发明涉及式(I)的大环化合物： 其中W，n，R1，Ra，Rb，R3，R4，M，Z，环A和环B在此被定义，并且其药学上可接受的盐，包括它们的制药组合物，以及它们用于治疗或预防丙型肝炎病毒感染的用途。