{(S)-1-[((S)-1-Cyclohexyl-ethylcarbamoyl)-hydroxy-methyl]-butyl}-carbamic acid benzyl ester | 402959-81-3

• 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: {(S)-1-[((S)-1-Cyclohexyl-ethylcarbamoyl)-hydroxy-methyl]-butyl}-carbamic acid benzyl ester
• 英文别名: benzyl N-[(3S)-1-[[(1S)-1-cyclohexylethyl]amino]-2-hydroxy-1-oxohexan-3-yl]carbamate
• CAS: 402959-81-3
• 化学式: C₂₂H₃₄N₂O₄
• 分子量: 390.523
• InChiKey: GSCYINLUIDJRLH-QICOWLOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {(S)-1-[((S)-1-Cyclohexyl-ethylcarbamoyl)-hydroxy-methyl]-butyl}-carbamic acid benzyl ester 在 palladium dihydroxide benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 作用下， 生成 ((S)-1-{(S)-1-[(S)-1-((S)-1-Cyclohexyl-ethylaminooxalyl)-butylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-methyl-propyl)-carbamic acid isopropyl ester
  参考文献：
  名称：

  Synthesis and evaluation of tripeptidyl α-Ketoamides as human rhinovirus 3C protease inhibitors

  摘要：

  We describe herein the synthesis and biological evaluation of a series of tripeptidyl alpha-ketoamides as human rhinovirus (HRV) 3C protease inhibitors. The most potent inhibitor discussed in this manuscript, 41, exhibited impressive enzyme inhibitory activity as well as antiviral activity against HRV-14. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00753-4
• 作为产物：
  描述：

  [(1S)-1-cyclohexylethyl]amine 、 (S)-3-(benzyloxycarbonyl)amino-2-hydroxyhexanoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 生成 {(S)-1-[((S)-1-Cyclohexyl-ethylcarbamoyl)-hydroxy-methyl]-butyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and evaluation of tripeptidyl α-Ketoamides as human rhinovirus 3C protease inhibitors

  摘要：

  We describe herein the synthesis and biological evaluation of a series of tripeptidyl alpha-ketoamides as human rhinovirus (HRV) 3C protease inhibitors. The most potent inhibitor discussed in this manuscript, 41, exhibited impressive enzyme inhibitory activity as well as antiviral activity against HRV-14. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00753-4

文献信息

• Peptidomimetic protease inhibitors
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP2368878A1

  公开（公告）日：2011-09-28

  The present invention relates to peptidomimetic compounds useful as protease inhibitors (1), particularly as serine protease inhibitors and more particularly as hepatitis C NS3 protease inhibitors; intermediates thereto; their preparation including novel steroselective processes to intermediates. The invention is also directed to pharmaceutical compositions and to methods for using the compounds for inhibiting HCV protease or treating a patient suffering from an HCV infection or physiological condition related to the infection. Also provided are pharmaceutical combinations comprising, in addition to one or more HCV serine protease inhibitors, one or more interferons exhibiting anti-HCV activity and/or one or more compounds having anti HCV activity and a pharmaceutically acceptable carrier, and methods for treating or preventing a HCV infection in a patient using the compositions. The present invention is also directed to a kit or pharmaceutical pack for treating or preventing HCV infection in a patient.

  本发明涉及肽类似物化合物，用作蛋白酶抑制剂（1），特别是丝氨酸蛋白酶抑制剂，更特别是丙型肝炎NS3蛋白酶抑制剂；中间体；它们的制备，包括到中间体的新型立体选择性过程。本发明还涉及制药组合物和使用这些化合物抑制HCV蛋白酶或治疗患有HCV感染或与感染相关的生理状况的患者的方法。还提供了药物组合物，其中除了一个或多个HCV丝氨酸蛋白酶抑制剂外，还包括一个或多个表现出抗HCV活性的干扰素和/或一个或多个具有抗HCV活性的化合物和一种药学上可接受的载体，并使用这些组合物治疗或预防患者的HCV感染的方法。本发明还涉及用于治疗或预防患者的HCV感染的套件或药物包。
• Chiral intermediates for the preparation of peptidomimetic protease inhibitors
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1876173A1

  公开（公告）日：2008-01-09

  The present application relates to intermediate compounds according to formula (24,25,26 and 27) for the preparation of peptidomimetic compounds which are useful as protease inhibitors: wherein is optionally substituted fused arylcycloalkyl; R11 is -CO2R13; R12 is iminic glycinimide derivative adduct; and R13 is acid protecting group or optionally substituted aliphatic group. wherein: R15 is optionally substituted aliphatic group; and R16 is acid protecting group, optionally substituted aryl, or optionally substituted aliphatic group. wherein: p° is amide protecting group;

  本申请涉及中间化合物，其化学式为（24、25、26和27），用于制备肽类模拟化合物，这些化合物可用作蛋白酶抑制剂： 其中，X是可选取代的融合芳基环烷基；R11是-CO2R13；R12是亚胺基甘氨酰亚胺衍生物加合物；R13是酸保护基或可选取代的脂肪基。 其中，R15是可选取代的脂肪基；R16是酸保护基、可选取代的芳基或可选取代的脂肪基。 其中，p°是酰胺保护基。
• PEPTIDOMIMETIC PROTEASE INHIBITORS
  申请人：BABINE ROBERT EDWARD

  公开号：US20120282219A1

  公开（公告）日：2012-11-08

  The present invention relates to peptidomimetic compounds useful as protease inhibitors, particularly as serine protease inhibitors and more particularly as hepatitis C NS3 protease inhibitors; intermediates thereto; their preparation including novel stereoselective processes to intermediates. The invention is also directed to pharmaceutical compositions and to methods for using the compounds for inhibiting HCV protease or treating a patient suffering from an HCV infection or physiological condition related to the infection. Also provided are pharmaceutical combinations comprising, in addition to one or more HCV serine protease inhibitors, one or more interferons exhibiting anti-HCV activity and/or one or more compounds having anti HCV activity and a pharmaceutically acceptable carrier, and methods for treating or preventing a HCV infection in a patient using the compositions. The present invention is also directed to a kit or pharmaceutical pack for treating or preventing HCV infection in a patient.

  本发明涉及肽类似物化合物，作为蛋白酶抑制剂，特别是作为丝氨酸蛋白酶抑制剂，更特别是作为丙型肝炎NS3蛋白酶抑制剂；以及其中间体；它们的制备，包括新的对中间体的立体选择性过程。本发明还涉及制药组合物，以及使用这些化合物抑制HCV蛋白酶或治疗患有HCV感染或与感染相关的生理状况的患者的方法。还提供了药物组合物，其中除了一个或多个HCV丝氨酸蛋白酶抑制剂外，还包括一个或多个表现出抗HCV活性的干扰素和/或一个或多个具有抗HCV活性的化合物和一种药学上可接受的载体，并使用这些组合物来治疗或预防患者的HCV感染。本发明还涉及用于治疗或预防患者HCV感染的工具包或药物包。
• Process for preparing chiral bicycloprolinates as intermediates for the preparation of peptidomimetic protease inhibitors
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1878720B1

  公开（公告）日：2010-10-06
• Peptidomimetic protease inhibitors and intermediates for their preparation As treatment for HCV infection
  申请人：Vertex Pharmaceuticals Inc.

  公开号：EP2368877B1

  公开（公告）日：2014-05-07