3-甲酰基h-咪唑并[1,5-a]吡啶-1-羧酸甲酯 | 1039356-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 3-甲酰基h-咪唑并[1,5-a]吡啶-1-羧酸甲酯
• 英文名称: Methyl 3-formylimidazo[1,5-a]pyridine-1-carboxylate
• CAS: 1039356-95-0
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: JAECLEINWMZAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲酰基h-咪唑并[1,5-a]吡啶-1-羧酸甲酯 在 水 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-((4,4-difluoropiperidin-1-yl)methyl)-N-((1-(hydroxymethyl)cyclopentyl)methyl)imidazo[1,5-a]pyridine-1-carboxamide
  参考文献：
  名称：

  Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy

  摘要：

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.082
• 作为产物：
  描述：

  2-氨基-2-(吡啶-2-基)乙酸甲酯 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 3-甲酰基h-咪唑并[1,5-a]吡啶-1-羧酸甲酯
  参考文献：
  名称：

  Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy

  摘要：

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.082

文献信息

• IMIDAZOPYRIDINE ANALOGS AS CB2 RECEPTOR MODULATORS, USEFUL IN THE TREATMENT OF PAIN, RESPIRATORY AND NON-RESPIRATORY DISEASES
  申请人：Bilodeau Mark T.

  公开号：US20090325936A1

  公开（公告）日：2009-12-31

  The present invention relates to compounds represented by Formula (I) and Formula (II): (I) (II) or pharmaceutically acceptable salts thereof. The present invention also provides pharmaceutical compositions comprising the instant compounds. This invention further provides methods to treat and prevent pain, respiratory and non-respiratory diseases.

  本发明涉及由公式(I)和公式(II)表示的化合物：(I) (II)或其药学上可接受的盐。本发明还提供包含即时化合物的药物组合物。本发明还提供治疗和预防疼痛、呼吸和非呼吸疾病的方法。
• [EN] IMIDAZOPYRIDINE ANALOGS AS CB2 RECEPTOR MODULATORS, USEFUL IN THE TREATMENT OF PAIN, RESPIRATORY AND NON-RESPIRATORY DISEASES<br/>[FR] ANALOGUES DE L'IMIDAZOPYRIDINE EN TANT QUE MODULATEURS DU RÉCEPTEUR DE CB2, UTILISABLES POUR LE TRAITEMENT DE LA DOULEUR ET DES MALADIES RESPIRATOIRES ET NON RESPIRATOIRES
  申请人：MERCK & CO INC

  公开号：WO2008085302A1

  公开（公告）日：2008-07-17

  [EN] The present invention relates to compounds represented by Formula (I) and Formula (II): (I) (II) or pharmaceutically acceptable salts thereof. The present invention also provides pharmaceutical compositions comprising the instant compounds. This invention further provides methods to treat and prevent pain, respiratory and non-respiratory diseases.
  [FR] La présente invention concerne des composés représentés par la formule (I) et la formule (II) : (I) (II) ou leurs sels pharmaceutiquement acceptables. L'invention concerne également des compositions pharmaceutiques comprenant les présents composés. L'invention concerne en outre des procédés et des méthodes de traitement et de prévention de la douleur et des maladies respiratoires et non respiratoires.
• Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy
  作者：B. Wesley Trotter、Kausik K. Nanda、Christopher S. Burgey、Craig M. Potteiger、James Z. Deng、Ahren I. Green、John C. Hartnett、Nathan R. Kett、Zhicai Wu、Darrell A. Henze、Kimberly Della Penna、Reshma Desai、Michael D. Leitl、Wei Lemaire、Rebecca B. White、Suzie Yeh、Mark O. Urban、Stefanie A. Kane、George D. Hartman、Mark T. Bilodeau

  DOI：10.1016/j.bmcl.2011.02.082

  日期：2011.4

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.