N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1H-pyrrolo[2,3-c]pyridine-5-carboxamide
• 英文别名: N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-1H-pyrrolo[2,3-c]pyridine-5-carboxamide
• 化学式: C₁₅H₁₈N₄O
• 分子量: 270.334
• InChiKey: PDGSKMBKOMNHDR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-二甲基吡啶 在 甲酸 、 硫酸 、 双氧水 、 对甲苯磺酸 、 potassium nitrate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 41.0h， 生成 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1H-pyrrolo[2,3-c]pyridine-5-carboxamide
  参考文献：
  名称：

  Discovery of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide, an Agonist of the α7 Nicotinic Acetylcholine Receptor, for the Potential Treatment of Cognitive Deficits in Schizophrenia:  Synthesis and Structure−Activity Relationship

  摘要：

  N-[(3R)-1-Azabicyclo[2.2.2] oct-3-yl] furo[2,3-c]pyridine-5-carboxamide (14, PHA-543,613), a novel agonist of the alpha 7 neuronal nicotinic acetylcholine receptor (alpha 7 nAChR), has been identified as a potential treatment of cognitive deficits in schizophrenia. Compound 14 is a potent and selective alpha 7 nAChR agonist with an excellent in vitro profile. The compound is characterized by rapid brain penetration and high oral bioavailability in rat and demonstrates in vivo efficacy in auditory sensory gating and, in an in vivo model to assess cognitive performance, novel object recognition.

  DOI：

  10.1021/jm0602413

文献信息

• Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease
  申请人：——

  公开号：US20030045540A1

  公开（公告）日：2003-03-06

  The invention provides compounds of Formula I: 1 where in W is 2 These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula I are useful to treat diseases or conditions in which &agr;7 is known to be involved.

  这项发明提供了Formula I的化合物： 其中W为 这些化合物可以是药用盐或组合物的形式，也可以是消旋混合物或其纯对映体。Formula I的化合物可用于治疗已知涉及α7的疾病或症状。
• [EN] QUINUCLIDINES-SUBSTITUTED-MULTI-CYCLIC-HETEROARYLS FOR THE TREATMENT OF DISEASE<br/>[FR] MULTI-HETEROARYLES CYCLIQUES SUBSTITUES PAR QUINUCLIDINES POUR LE TRAITEMENT DE MALADIES
  申请人：UPJOHN CO

  公开号：WO2002100857A1

  公开（公告）日：2002-12-19

  The invention provides compounds of Formula (I), where in W is. These compounds may be in the form of pharmaceutical salts or compositions, racemic mixtures, or pure enantiomers thereof. The compounds of Formula (I) are useful in pharmaceuticals to treat diseases or conditions in which α7 is known to be involved.

  该发明提供了公式（I）的化合物，其中W是。这些化合物可以是药物盐或组合物，外消旋混合物或其纯对映体。公式（I）的化合物在制药学中用于治疗已知涉及α7的疾病或病症。
• QUINUCLIDINES-SUBSTITUTED-MULTI-CYCLIC-HETEROARYLS FOR THE TREATMENT OF DISEASE
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1406901A1

  公开（公告）日：2004-04-14
• US7067515B2
  申请人：——

  公开号：US7067515B2

  公开（公告）日：2006-06-27
• Discovery of <i>N</i>-[(3<i>R</i>)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-<i>c</i>]pyridine-5-carboxamide, an Agonist of the α7 Nicotinic Acetylcholine Receptor, for the Potential Treatment of Cognitive Deficits in Schizophrenia:  Synthesis and Structure−Activity Relationship
  作者：Donn G. Wishka、Daniel P. Walker、Karen M. Yates、Steven C. Reitz、Shaojuan Jia、Jason K. Myers、Kirk L. Olson、E. Jon Jacobsen、Mark L. Wolfe、Vincent E. Groppi、Alexander J. Hanchar、Bruce A. Thornburgh、Luz A. Cortes-Burgos、Erik H. F. Wong、Brian A. Staton、Thomas J. Raub、Nicole R. Higdon、Theron M. Wall、Raymond S. Hurst、Rodney R. Walters、William E. Hoffmann、Mihaly Hajos、Stanley Franklin、Galen Carey、Lisa H. Gold、Karen K. Cook、Steven B. Sands、Sabrina X. Zhao、John R. Soglia、Amit S. Kalgutkar、Stephen P. Arneric、Bruce N. Rogers

  DOI：10.1021/jm0602413

  日期：2006.7.1

  N-[(3R)-1-Azabicyclo[2.2.2] oct-3-yl] furo[2,3-c]pyridine-5-carboxamide (14, PHA-543,613), a novel agonist of the alpha 7 neuronal nicotinic acetylcholine receptor (alpha 7 nAChR), has been identified as a potential treatment of cognitive deficits in schizophrenia. Compound 14 is a potent and selective alpha 7 nAChR agonist with an excellent in vitro profile. The compound is characterized by rapid brain penetration and high oral bioavailability in rat and demonstrates in vivo efficacy in auditory sensory gating and, in an in vivo model to assess cognitive performance, novel object recognition.