[2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-[4-(pyridin-3yl)butyl]carbamic acid benzyl ester | 192643-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-[4-(pyridin-3yl)butyl]carbamic acid benzyl ester
• 英文别名: benzyl N-[2-[5-[1-(7-azabicyclo[2.2.1]heptan-7-yl)-2-methyl-1-oxopropan-2-yl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-N-(4-pyridin-3-ylbutyl)carbamate
• CAS: 192643-89-3
• 化学式: C₄₅H₅₂N₄O₃
• 分子量: 696.933
• InChiKey: VYBIAQZFZYMGHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-[4-(pyridin-3yl)butyl]carbamic acid benzyl ester 在 钯 氢气 作用下， 以 CH₂Cl₂-MeOH-concentrated NH₄OH 、 乙醇 、 乙酸乙酯 为溶剂， 生成 1-(7-azabicyclo [2.2.1]hept-7-yl)-2-[2-(3,5-dimethylphenyl)-3-[2-[4-(pyridin-3-yl)butylamino]ethyl]-1H-indol-5-yl]-2-methylpropan-1-one
  参考文献：
  名称：

  Antagonists of gonadotropin releasing hormone

  摘要：

  公开了式（I）的化合物及其药用盐，这些化合物可作为GnRH拮抗剂，因此可能对男性和女性的各种性激素相关和其他疾病的治疗有用。

  公开号：

  US06200957B1
• 作为产物：
  描述：

  2-[3-[2-[benzyloxycarbonyl-[4-(pyridin-3-yl)butyl]amino]ethyl]-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester 在 氢氧化钾 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-[4-(pyridin-3yl)butyl]carbamic acid benzyl ester
  参考文献：
  名称：

  Potent nonpeptide GnRH receptor antagonists derived from substituted indole-5-carboxamides and -acetamides bearing a pyridine side-chain terminus

  摘要：

  A pyridine side-chain terminus has been incorporated into the indole-5-carboxamide and indole-5-acetamide series of GnRH antagonists. Potent activity was observed in binding and functional assays. Certain branched or cyclic tertiary amides were identified as preferred in each series. Alkylation of the side-chain secondary amine had generally unfavorable effects. Variations of the gem-dialkyl substituents in the indole-5-acetamide series were also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00275-x

文献信息

• Antagonists of gonadotropin releasing hormone
  申请人：Merck & Co., Inc.

  公开号：US06200957B1

  公开（公告）日：2001-03-13

  There are disclosed compounds of formula (I) and pharmaceutically acceptable salts thereof which are useful as antagonists of GnRH and as such may be useful for the treatment of a variety of sex-hormone related and other conditions in both men and women.

  公开了式（I）的化合物及其药用盐，这些化合物可作为GnRH拮抗剂，因此可能对男性和女性的各种性激素相关和其他疾病的治疗有用。
• [EN] ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE<br/>[FR] ANTAGONISTES DE LA GONADOLIBERINE
  申请人：MERCK & CO INC

  公开号：WO2000004013A1

  公开（公告）日：2000-01-27

  The present invention relates to compounds of formula (I) which are non-peptide antagonists of GnRH which can be used to treat a variety of sex-hormone related conditions in men and women, to methods for their preparation, and to methods and pharmaceutical compositions containing said compounds for use in mammals.

  本发明涉及式(I)的化合物，它们是GnRH的非肽拮抗剂，可用于治疗男性和女性的各种与性激素相关的疾病，以及它们的制备方法和包含所述化合物的方法和制药组合物，用于哺乳动物。
• ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE
  申请人：Merck & Co., Inc. (a New Jersey corp.)

  公开号：EP0873336B1

  公开（公告）日：2002-03-27
• US6200957B1
  申请人：——

  公开号：US6200957B1

  公开（公告）日：2001-03-13
• Potent nonpeptide GnRH receptor antagonists derived from substituted indole-5-carboxamides and -acetamides bearing a pyridine side-chain terminus
  作者：Wallace T. Ashton、Rosemary M. Sisco、Yi Tien Yang、Jane-Ling Lo、Joel B. Yudkovitz、Patrice H. Gibbons、George R. Mount、Rena Ning Ren、Bridget S. Butler、Kang Cheng、Mark T. Goulet

  DOI：10.1016/s0960-894x(01)00275-x

  日期：2001.7

  A pyridine side-chain terminus has been incorporated into the indole-5-carboxamide and indole-5-acetamide series of GnRH antagonists. Potent activity was observed in binding and functional assays. Certain branched or cyclic tertiary amides were identified as preferred in each series. Alkylation of the side-chain secondary amine had generally unfavorable effects. Variations of the gem-dialkyl substituents in the indole-5-acetamide series were also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.