2-ethyl-6-fluoro-3-piperidin-4-yl-1H-indole | 852867-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-ethyl-6-fluoro-3-piperidin-4-yl-1H-indole
• CAS: 852867-61-9
• 化学式: C₁₅H₁₉FN₂
• 分子量: 246.328
• InChiKey: UBDFRZKWMQOFLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-6-fluoro-3-piperidin-4-yl-1H-indole 在 potassium phosphate 、 copper(l) iodide 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl 6-[3-[1-[(3R)-4-(3,4-dichlorophenyl)-3-(ethylcarbamoylamino)butyl]piperidin-4-yl]-2-ethyl-6-fluoroindol-1-yl]pyridine-3-carboxylate
  参考文献：
  名称：

  Rodent selectivity of piperidine-4-yl-1H-indoles, a series of CC chemokine receptor-3 (CCR3) antagonists: Insights from a receptor model

  摘要：

  Rodent selectivity data of piperidine-4-yl-1H-indoles, a series of CC chemokine receptor-3 (CCR3) antagonists, are presented and discussed as part of an overall optimization effort within this lead compound class. Although attachment of an acidic moiety to the 1-position of the indole led to an overall balanced in vitro profile, in particular reducing inhibition of the hERG channel, potency on the rat and mouse receptor worsened. These findings could be rationalized in the context of a CCR3 homology model. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.063
• 作为产物：
  描述：

  3-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-ethyl-6-fluoro-1H-indole 在 钯 乙醚 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、13.51 MPa 条件下， 反应 1.0h， 以1.2 g (85%) of pure product is obtained的产率得到2-ethyl-6-fluoro-3-piperidin-4-yl-1H-indole
  参考文献：
  名称：

  Piperidine-substituted indoles

  摘要：

  本发明涉及一种新型的哌啶取代的吲哚或其杂环衍生物，其化学式为1：其中R1、R5、R6、R7、A、B、D-E、Y、i、j、n和m的定义如下。化合物1的作用是作为CCR-3的激动剂或拮抗剂。本发明还涉及其药学上可接受的盐，更具体地提供了含有药学上可接受的载体和本发明中化合物之一或其药学上可接受的盐的治疗有效剂量的药物组合物。

  公开号：

  US07759365B2

文献信息

• Novel Piperidine-Substituted Indoles
  申请人：Martyres Domnic

  公开号：US20060247230A1

  公开（公告）日：2006-11-02

  Disclosed are novel piperidine-substituted indoles- or heteroderivatives thereof of the formula 1: wherein R 1 , R 5 , R 6 , R 7 , A, B, D-E, Y, i, j, n and m are defined as below. The compounds of formula 1 are useful as agonists or antagonists of CCR-3. The present invention is also directed to pharmaceutically acceptable salts thereof, more particularly to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt thereof.

  本发明涉及一种新型的吡啶取代的吲哚或其杂环衍生物，其化学式为1：其中R1、R5、R6、R7、A、B、D-E、Y、i、j、n和m如下所定义。化合物1可用作CCR-3的激动剂或拮抗剂。本发明还涉及其药学上可接受的盐，更具体地提供了包含药学上可接受的载体和本发明化合物或其药学上可接受的盐的至少一种的治疗有效量的制药组合物。
• Novel piperidine-substituted indoles-or heteroderivatives thereof
  申请人：Anderskewitz Ralf

  公开号：US20050153979A1

  公开（公告）日：2005-07-14

  Accordingly, one object of the present invention are novel piperidine-substituted indoles- or heteroderivatives thereof of the formula 1: wherein R 1 , R 5 , R 6 , A, B, D-E, X—W—V, Y, i, j, n and m are defined as below. Another object of the present invention is to provide agonists or antagonists of CCR-3, or pharmaceutically acceptable salts thereof, more particularly to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt thereof.

  因此，本发明的一个目标是提供一种新型的哌啶取代的吲哚或其杂环衍生物，其化学式为1：其中R1，R5，R6，A，B，D-E，X—W—V，Y，i，j，n和m如下所定义。本发明的另一个目标是提供CCR-3的激动剂或拮抗剂，或其药学上可接受的盐，更具体地提供包含药学上可接受的载体和本发明化合物或其药学上可接受的盐的治疗有效量的制剂。
• Piperidine-substituted indoles-or heteroderivatives thereof
  申请人：Boehringer Ingelheim International GmbH

  公开号：US07544806B2

  公开（公告）日：2009-06-09

  Accordingly, one object of the present invention are novel piperidine-substituted indoles- or heteroderivatives thereof of the formula 1: wherein R1, R5, R6, A, B, D-E, X-W-V, Y, i, j, n and m are defined as below. Another object of the present invention is to provide agonists or antagonists of CCR-3, or pharmaceutically acceptable salts thereof, more particularly to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt thereof.

  因此，本发明的一个目的是提供式1中的新型哌啶取代吲哚或其杂环衍生物，其中R1、R5、R6、A、B、D-E、X-W-V、Y、i、j、n和m的定义如下。本发明的另一个目的是提供CCR-3的激动剂或拮抗剂，或其药学上可接受的盐，更具体地提供包含药学上可接受的载体和本发明化合物或其药学上可接受的盐的至少一种的治疗有效量的制剂。
• [EN] NOVEL PIPERIDINE-SUBSTITUTED INDOLES- OR HETERO-DERIVATIVES THEREOF AND THEIR USE AS MODULATORS OF CHEMOKINE RECEPTOR (CCR-3)<br/>[FR] NOUVEAUX INDOLES SUBSTITUES PAR PIPERIDINES OU HETERODERIVES ASSOCIES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2005049559A3

  公开（公告）日：2006-04-13
• WO2006/117314
  申请人：——

  公开号：——

  公开（公告）日：——