(1R,9R,10S)-17-benzyl-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one | 1256921-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (1R,9R,10S)-17-benzyl-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
• CAS: 1256921-79-5
• 化学式: C₂₄H₂₇NO₃
• 分子量: 377.483
• InChiKey: JMWVNTBRKDDIFW-WXFUMESZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,9R,10S)-17-benzyl-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one 在 dirhodium tetraacetate 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 156.0h， 生成
  参考文献：
  名称：

  [EN] RING-CONTRACTED MORPHINANS AND THE USE THEREOF
  [FR] MORPHINANES À CYCLE CONTRACTÉ ET LEUR UTILISATION

  摘要：

  该申请涉及公式（I）或（IA）的化合物及其药用盐和溶剂化合物，其中R1、R2、R3和G的定义如规范中所述。本发明还涉及使用公式（I）或（IA）的化合物，以及其药用盐和溶剂化合物，用于治疗对调节一个或多个阿片受体敏感的疾病，或作为合成中间体。本发明的某些化合物特别适用于治疗疼痛。

  公开号：

  WO2015100174A1
• 作为产物：
  描述：

  (4b'R,8a'S,9'R)-11'-benzyl-3'-methoxy-7',8',9',10'-tetrahydro-5'H,8a'H-spiro[[1,3]dioxolane-2,6'-[9,4b](epiminoethano)phenanthren]-8a'-ol 在 盐酸 、 水 作用下， 以92%的产率得到(1R,9R,10S)-17-benzyl-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
  参考文献：
  名称：

  Design and synthesis of KNT-127, a δ-opioid receptor agonist effective by systemic administration

  摘要：

  We have reported previously the novel delta-opioid agonist, SN-28, which was more potent in in vitro assays than the prototype delta-agonists, TAN-67 and SNC-80. However, when administered by subcutaneous injection, this compound showed no analgesic effect at dosages greater than 30 mg/kg in the acetic acid writhing test. We speculated that SN-28 was not effective in the test because the presence of the charged ammonium groups prevented its penetration through the blood-brain barrier. On the basis of our proposal, we designed the novel delta-agonist, KNT-127, which was effective with systemic administration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.083

文献信息

• SPIROCYCLIC MORPHINANS AND THEIR USE
  申请人：Purdue Pharma LP

  公开号：EP2931726B1

  公开（公告）日：2017-01-25
• PYRIDONEMORPHINAN ANALOGS AND BIOLOGICAL ACTIVITY ON OPIOID RECEPTORS
  申请人：Purdue Pharma LP

  公开号：EP2931724B1

  公开（公告）日：2017-01-25
• Spirocyclic Morphinans and Their Use
  申请人：Purdue Pharma L.P.

  公开号：US20140179724A1

  公开（公告）日：2014-06-26

  The application is directed to compounds of Formula I′-A especially to compounds of Formula I-A and pharmaceutically acceptable salts and solvates thereof, wherein R 1a -R 5a , Y, Z are defined as set forth in the specification. The invention is also directed to use of compounds of Formula I′-A, and especially compounds of Formula I-A, to treat disorders responsive to the modulation of one or more opioid receptors, or as synthetic intermediates. Certain compounds of the present invention are especially useful for treating pain.
• RING-CONTRACTED MORPHINANS AND THE USE THEREOF
  申请人：PURDUE PHARMA L.P.

  公开号：US20160340316A1

  公开（公告）日：2016-11-24

  The application is directed to compounds of Formula (I) or (IA) and pharmaceutically acceptable salts and solvates thereof, wherein R 1 R 2 , R3 and G are defined as set forth in the specification. The invention is also directed to use of compounds of Formula (I) or(IA), and the pharmaceutically acceptable salts and solvates thereof, to treat disorders responsive to the modulation of one or more opioid receptors, or as synthetic intermediates. Certain compounds of the present invention are especially useful for treating pain.
• US8987287B2
  申请人：——

  公开号：US8987287B2

  公开（公告）日：2015-03-24