tert-butyl 4-(6-(diethylcarbamoyl)pyridin-3-yl)spiro[chromene-2,4'-piperidine]-1'-carboxylate | 911227-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: tert-butyl 4-(6-(diethylcarbamoyl)pyridin-3-yl)spiro[chromene-2,4'-piperidine]-1'-carboxylate
• 英文别名: Tert-butyl 4-[6-(diethylcarbamoyl)pyridin-3-yl]spiro[chromene-2,4'-piperidine]-1'-carboxylate
• CAS: 911227-47-9
• 化学式: C₂₈H₃₅N₃O₄
• 分子量: 477.604
• InChiKey: CCWNIBZLFLFFQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(6-(diethylcarbamoyl)pyridin-3-yl)spiro[chromene-2,4'-piperidine]-1'-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 10.0h， 以95%的产率得到
  参考文献：
  名称：

  WO2006/105442

  摘要：

  公开号：
• 作为产物：
  描述：

  5-溴吡啶-2-甲酰氯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 palladium 10% on activated carbon potassium acetate 、 sodium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 tert-butyl 4-(6-(diethylcarbamoyl)pyridin-3-yl)spiro[chromene-2,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  WO2006/105442

  摘要：

  公开号：

文献信息

• [EN] SPIROCYCLIC HETEROCYCLIC DERIVATIVES AND METHODS OF THEIR USE<br/>[FR] DERIVES HETEROCYCLIQUES SPIROCYCLIQUES ET LEURS METHODES D'UTILISATION
  申请人：ADOLOR CORP

  公开号：WO2005033073A3

  公开（公告）日：2005-07-28
• Spirocyclic Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of <i>N</i>,<i>N</i>-Diethyl-3-hydroxy-4-(spiro[chromene-2,4′-piperidine]-4-yl) Benzamide (ADL5747)
  作者：Bertrand Le Bourdonnec、Rolf T. Windh、Lara K. Leister、Q. Jean Zhou、Christopher W. Ajello、Minghua Gu、Guo-Hua Chu、Paul A. Tuthill、William M. Barker、Michael Koblish、Daniel D. Wiant、Thomas M. Graczyk、Serge Belanger、Joel A. Cassel、Marina S. Feschenko、Bernice L. Brogdon、Steven A. Smith、Michael J. Derelanko、Steve Kutz、Patrick J. Little、Robert N. DeHaven、Diane L. DeHaven-Hudkins、Roland E. Dolle

  DOI：10.1021/jm900773n

  日期：2009.9.24

  Selective, nonpeptidic delta opioid receptor agonists have been the subject of great interest as potential novel analgesic agents. The discoveries of BW373U86 (1) and SNC80 (2) contributed to the rapid expansion of research in this field. However, poor drug-like properties and low therapeutic indices have prevented clinical evaluation of these agents. Doses of I and 2 similar to those required for analgesic activity produce convulsions in rodents and nonhuman primates. Recently, we described a novel series of potent, selective. and orally bioavailable delta opioid receptor agonists. The lead derivative, ADL5859 (4), is currently in phase It proof-of-concept studies for the management of pain. Further structure activity relationship exploration has led to the discovery of ADL5747 (36), which is approximately 50-fold more potent than 4 in an animal model of inflammatory pain. On the basis of its favorable efficacy, safety, and pharmacokinetic profile, 36 was selected as a clinical candidate for the treatment of pain.
• WO2006/105442
  申请人：——

  公开号：——

  公开（公告）日：——