1-[(2R)-2-amino-3-(1H-indol-3-yl)propionyl]-(3R)-3-benzylpiperidine-3-carboxylic acid trimethylhydrazide | 339539-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-[(2R)-2-amino-3-(1H-indol-3-yl)propionyl]-(3R)-3-benzylpiperidine-3-carboxylic acid trimethylhydrazide
• 英文别名: (3R)-1-[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]-3-benzyl-N,N',N'-trimethylpiperidine-3-carbohydrazide
• CAS: 339539-88-7
• 化学式: C₂₇H₃₅N₅O₂
• 分子量: 461.607
• InChiKey: GXXVBAWDZIJHSX-YIXXDRMTSA-N

物化性质

• 沸点：
  669.4±65.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(2R)-2-amino-3-(1H-indol-3-yl)propionyl]-(3R)-3-benzylpiperidine-3-carboxylic acid trimethylhydrazide 在 N-甲基吗啉 、 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 N,N-二甲基乙酰胺 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 阿拉莫林富马酸盐
  参考文献：
  名称：

  A Practical Synthesis of the Pseudotripeptide RC-1291

  摘要：

  The rapid process development of a scaleable synthesis of the pseudotripeptide RC-1291 for preclinical and clinical evaluation is described. By employing a nontraditional N-to-C coupling strategy, the peptide chain of RC-1291 was assembled in high yield, with minimal racemization and in an economical manner by introducing the most expensive component last. A one-pot deprotection/crystallization procedure was developed for the isolation of RC-1291 free base, which afforded the target compound in excellent yield and with a purity of > 99.5% without chromatographic purification.

  DOI：

  10.1021/op0502506
• 作为产物：
  描述：

  BOC-D-色氨酸 在 N-甲基吗啉 、 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 N,N-二甲基乙酰胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 1-[(2R)-2-amino-3-(1H-indol-3-yl)propionyl]-(3R)-3-benzylpiperidine-3-carboxylic acid trimethylhydrazide
  参考文献：
  名称：

  A Practical Synthesis of the Pseudotripeptide RC-1291

  摘要：

  The rapid process development of a scaleable synthesis of the pseudotripeptide RC-1291 for preclinical and clinical evaluation is described. By employing a nontraditional N-to-C coupling strategy, the peptide chain of RC-1291 was assembled in high yield, with minimal racemization and in an economical manner by introducing the most expensive component last. A one-pot deprotection/crystallization procedure was developed for the isolation of RC-1291 free base, which afforded the target compound in excellent yield and with a purity of > 99.5% without chromatographic purification.

  DOI：

  10.1021/op0502506

文献信息

• Compound with growth hormone releasing properties
  申请人：——

  公开号：US20010041720A1

  公开（公告）日：2001-11-15

  The present invention describes a new compound, 2-Amino-N-[(1R)-2-[(3R)-3-benzyl-3-(N,N′,N′-trimethylhydrazinocarbonyl)piperidin-1-y]-1-(1H-indol-3-ylmethyl)-2-oxoethyl]-2-methylpropionamide, having the formula: 1 and pharmaceutically acceptable salts thereof, compositions containing them, and their use for treating medical disorders resulting from a deficiency in growth hormone.

  本发明描述了一种新化合物，2-氨基-N-[(1R)-2-[(3R)-3-苄基-3-(N,N′,N′-三甲基肼甲酰)piperidin-1-yl]-1-(1H-吲哚-3-基甲基)-2-氧乙基]-2-甲基丙酰胺，其化学式为1，以及其在医药上可接受的盐、含有它们的组合物，以及它们用于治疗由生长激素缺乏引起的医学疾病。
• [EN] COMPOUND WITH GROWTH HORMONE RELEASING PROPERTIES<br/>[FR] COMPOSE PRESENTANT DES PROPRIETES DE LIBERATION D'HORMONE DE CROISSANCE
  申请人：NOVO NORDISK AS

  公开号：WO2001034593A1

  公开（公告）日：2001-05-17

  The present invention relates to a novel diastereomeric compound, pharmaceutically acceptable salts thereof, compositions containing them, and their use for treating medical disorders resulting from a deficiency in growth hormone, (Fig. 1).

  本发明涉及一种新型非对映异构化合物及其药学上可接受的盐、含有它们的组合物以及它们用于治疗由生长激素缺乏引起的医学障碍的用途。(图1)
• COMPOUND WITH GROWTH HORMONE RELEASING PROPERTIES
  申请人：NOVO NORDISK A/S

  公开号：EP1230236A1

  公开（公告）日：2002-08-14
• US6576648B2
  申请人：——

  公开号：US6576648B2

  公开（公告）日：2003-06-10
• A Practical Synthesis of the Pseudotripeptide RC-1291
  作者：Bernhard J. Paul、Benjamin J. Littler、Frederic Jos、Paul F. Vogt、Seemon H. Pines

  DOI：10.1021/op0502506

  日期：2006.3.1

  The rapid process development of a scaleable synthesis of the pseudotripeptide RC-1291 for preclinical and clinical evaluation is described. By employing a nontraditional N-to-C coupling strategy, the peptide chain of RC-1291 was assembled in high yield, with minimal racemization and in an economical manner by introducing the most expensive component last. A one-pot deprotection/crystallization procedure was developed for the isolation of RC-1291 free base, which afforded the target compound in excellent yield and with a purity of > 99.5% without chromatographic purification.