Ethyl 4-(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate | 183283-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Ethyl 4-(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate
• 英文别名: methyl 4-(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate；Ethyl 4-(2-methylimidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate
• CAS: 183283-23-0
• 化学式: C₁₅H₂₀N₄O₂
• 分子量: 288.349
• InChiKey: JVFHVQQJTVUGAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 70.0h， 生成 2-Methyl-1-piperidin-4-yl-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  CHEMICAL COMPOUNDS

  摘要：

  本发明提供式(I)化合物，其中R1、R2、R3、R4、Het和m如说明书中所定义。本发明的化合物是趋化因子CCR5受体活性的调节剂，特别是拮抗剂。

  公开号：

  US20090209578A1
• 作为产物：
  描述：

  4-乙氧基-3-硝基吡啶 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 110.0h， 生成 Ethyl 4-(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  Discovery and Evaluation of a Series of 3-Acylindole Imidazopyridine Platelet-Activating Factor Antagonists

  摘要：

  Studies conducted with the goal of discovering a second-generation platelet-activating factor (PAF) antagonist have identified a novel class of potent and orally active antagonists which have high aqueous solubility and long duration of action in animal models. The compounds arose from the combination of the lipophilic indole portion of Abbott's first-generation PAF antagonist ABT-299 (2) with the methylimidazopyridine heterocycle moiety of British Biotechnology's BB-882 (1) and possess the positive attributes of both of these clinical candidates. Structure-activity relationship (SAR) studies indicated that modification of the indole and benzoyl spacer of lead compound 7b gave analogues that were more potent, longer-lived, and bioavailable and resulted in the identification of 1-(N,N-dimethylcarbamoyl)-4-ethynyl-3-(3-fluoro-4-[(1H-2-methylimidazo[4,5-c]pyrid-1-yl)methyl] benzoyl}indole hydrochloride (ABT-491, 22m.HCl) which has been evaluated extensively and is currently in clinical development.

  DOI：

  10.1021/jm970389+

文献信息

• CHEMICAL COMPOUNDS
  申请人：Barber Christopher Gordon

  公开号：US20090209578A1

  公开（公告）日：2009-08-20

  The present invention provides compounds of formula (I) wherein R 1 , R 2 , R 3 , R 4 , Het and m are as defined in the description. The compounds of the present invention are modulators, especially antagonists, of the activity of chemokine CCR5 receptors.

  本发明提供式(I)化合物，其中R1、R2、R3、R4、Het和m如说明书中所定义。本发明的化合物是趋化因子CCR5受体活性的调节剂，特别是拮抗剂。
• Discovery and Evaluation of a Series of 3-Acylindole Imidazopyridine Platelet-Activating Factor Antagonists
  作者：Michael L. Curtin、Steven K. Davidsen、H. Robin Heyman、Robert B. Garland、George S. Sheppard、Alan S. Florjancic、Lianhong Xu、George M. Carrera、Douglas H. Steinman、Jeff A. Trautmann、Daniel H. Albert、Terrance J. Magoc、Paul Tapang、David A. Rhein、Richard G. Conway、Gongjin Luo、Jon F. Denissen、Kennan C. Marsh、Douglas W. Morgan、James B. Summers

  DOI：10.1021/jm970389+

  日期：1998.1.1

  Studies conducted with the goal of discovering a second-generation platelet-activating factor (PAF) antagonist have identified a novel class of potent and orally active antagonists which have high aqueous solubility and long duration of action in animal models. The compounds arose from the combination of the lipophilic indole portion of Abbott's first-generation PAF antagonist ABT-299 (2) with the methylimidazopyridine heterocycle moiety of British Biotechnology's BB-882 (1) and possess the positive attributes of both of these clinical candidates. Structure-activity relationship (SAR) studies indicated that modification of the indole and benzoyl spacer of lead compound 7b gave analogues that were more potent, longer-lived, and bioavailable and resulted in the identification of 1-(N,N-dimethylcarbamoyl)-4-ethynyl-3-(3-fluoro-4-[(1H-2-methylimidazo[4,5-c]pyrid-1-yl)methyl] benzoyl}indole hydrochloride (ABT-491, 22m.HCl) which has been evaluated extensively and is currently in clinical development.