6-chloro-N-cyclopentylnicotinamide | 585544-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-chloro-N-cyclopentylnicotinamide
• 英文别名: 6-chloro-N-cyclopentlypyridine-3-carboxamide；6-chloro-N-cyclopentylpyridine-3-carboxamide
• CAS: 585544-26-9
• 化学式: C₁₁H₁₃ClN₂O
• mdl: MFCD09804913
• 分子量: 224.69
• InChiKey: INCYPOVYPIHCSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-N-cyclopentylnicotinamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-cyclopentyl-6-(pyridin-2-ylethynyl)nicotinamide
  参考文献：
  名称：

  Efficacy switching SAR of mGluR5 allosteric modulators: Highly potent positive and negative modulators from one chemotype

  摘要：

  A series of metabotropic glutamate 5 receptor (mGluR5) allosteric ligands with positive, negative or no modulatory efficacy is described. The ability of this series to yield both mGluR5 PAMs and NAMs with single-digit nanomolar potency is unusual, and the underlying SAR is detailed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.103
• 作为产物：
  描述：

  6-氯吡啶-3-羰酰氯 、 环戊胺 以 乙腈 为溶剂， 反应 2.0h， 以4.39 g的产率得到6-chloro-N-cyclopentylnicotinamide
  参考文献：
  名称：

  Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator

  摘要：

  This Letter describes the discovery of a novel series of mGluR5 positive allosteric modulators (PAMs). The lead compound, 11c, exhibits excellent potency (EC50 = 30 nM) in vitro, and reaches high brain levels in both rats and mice after oral administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.095

文献信息

• [EN] COMBINATION OF CB2 MODULATORS AND PDE4 INHIBITORS FOR USE IN MEDICINE<br/>[FR] COMBINAISON DE MODULATEURS DU CB2 ET D'INHIBITEURS DE LA PDE4 UTILISEE EN MEDECINE
  申请人：GLAXO GROUP LTD

  公开号：WO2005074939A1

  公开（公告）日：2005-08-18

  Combination of one or more CB2 modulators such as a compound of formula (I), (II) and (III); and one more PDE4 inhibitors are useful of treating conditions which are mediated by the activity of CB2 receptors or conditions which are mediated by PDE4, such as an immune disorder, an inflamatory disorder, pain, rheumatoid.

  一种或多种CB2调节剂的组合，例如式(I)、(II)和(III)的化合物；以及一种或多种PDE4抑制剂对于治疗由CB2受体活性介导的疾病或由PDE4介导的疾病，如免疫紊乱、炎症性疾病、疼痛、类风湿等症状是有用的。
• [EN] PYRIDINE DERIVATIVES AS CB2 RECEPTOR MODULATORS<br/>[FR] DERIVES DE PYRIDINE MODULATEURS DU RECEPTEUR CB2
  申请人：GLAXO GROUP LTD

  公开号：WO2004029026A1

  公开（公告）日：2004-04-08

  The present invention relates to novel pyridine derivatives, pharmaceutical compositions containing these compounds and their use in the treatment of diseases, particularly pain, which diseases are caused directly or indirectly by an increase or decrease in activity of the cannabinoid receptor.

  本发明涉及新型吡啶衍生物，含有这些化合物的药物组合物以及它们在治疗疾病，特别是由大麻素受体活性增加或减少直接或间接引起的疾病中的应用。
• Nicotinamide derivatives useful as p38 inhibitors
  申请人：Aston Mary Nicola

  公开号：US20050176964A1

  公开（公告）日：2005-08-11

  Compounds of formula (I): are inhibitors of p38 kinase and are useful in the treatment of conditions or disease states mediated by p38 kinase activity or mediated by cytokines produced by the activity of p38.

  式(I)的化合物是p38激酶的抑制剂，并且在治疗由p38激酶活性介导或由p38活性产生的细胞因子介导的疾病状态或条件中有用。
• Pyridine derivatives as cb2 receptor modulators
  申请人：Eatherton John Andrew

  公开号：US20060240048A1

  公开（公告）日：2006-10-26

  The present invention relates to novel pyridine derivatives, pharmaceutical compositions containing these compounds and their use in the treatment of diseases, particularly pain, which diseases are caused directly or indirectly by an increase or decrease in activity of the cannabinoid receptor.

  本发明涉及新型的吡啶衍生物、含有这些化合物的药物组合物以及它们在治疗疾病，特别是由于大麻素受体活性增加或减少而直接或间接引起的疼痛等疾病中的应用。
• Nicotinamide Derivatives Useful as p38 Inhibitors
  申请人：Aston Nicola

  公开号：US20060264479A1

  公开（公告）日：2006-11-23

  Compounds of formula (I): are inhibitors of p38 kinase and are useful in the treatment of conditions or disease states mediated by p38 kinase activity or mediated by cytokines produced by the activity of p38.

  式（I）的化合物是p38激酶的抑制剂，并且在治疗由p38激酶活性介导或由p38活性产生的细胞因子介导的疾病状态或条件中有用。