2-(6-fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol | 1054629-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-(6-fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol
• 英文别名: 2-[6-fluoro-5-(methylamino)pyridin-2-yl]-1-benzofuran-5-ol
• CAS: 1054629-47-8
• 化学式: C₁₄H₁₁FN₂O₂
• 分子量: 258.252
• InChiKey: FXERARHKNULYEN-UHFFFAOYSA-N

物化性质

• 沸点：
  458.6±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-溴-2-氟吡啶-3-胺 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hexamethyldisilazane 、 三溴化硼 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2-(6-fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol
  参考文献：
  名称：

  Synthesis and evaluation of pyridylbenzofuran, pyridylbenzothiazole and pyridylbenzoxazole derivatives as 18F-PET imaging agents for β-amyloid plaques

  摘要：

  The synthesis and SAR of new beta-amyloid binding agents are reported. Evaluation of important properties for achieving good signal-to-background ratio is described. Compounds 27, 33, and 36 displayed desirable lipophilic and pharmacokinetic properties. Compound 27 was further evaluated with autoradiographic studies in vitro on human brain tissue and in vivo in Tg2576 mice. Compound 27 showed an increased signal-to-background ratio compared to flutemetamol 4, indicating its suitability as PET ligand for b-amyloid deposits in AD patients. The preparation of the corresponding F-18-labeled PET radioligand of compound 27 is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.011
• 作为试剂：
  描述：

  [2-fluoro-6-(5-methoxy-benzofuran-2-yl)-pyridin-3-yl]-methyl-amine 、 三溴化硼 、 碳酸氢钠 在 氮气 、 二氯甲烷 、 Brine 、 Sodium sulfate-III 、 crude product 、 2-(6-fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以afforded the title compound 2-(6-fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol (22 mg) as an off-white solid的产率得到2-(6-fluoro-5-methylamino-pyridin-2-yl)-benzofuran-5-ol
  参考文献：
  名称：

  2-heteroaryl substituted benzothiophenes and benzofuranes 709

  摘要：

  本发明涉及新型的2-杂环芳基取代苯并噻吩和苯并呋喃衍生物、其前体以及这些化合物的治疗用途，其结构式（Ia）如下： 并且本发明涉及适用于成像活体患者中淀粉样沉积物的新型2-杂环芳基取代苯并噻吩和苯并呋喃衍生物、其组成、使用方法以及制备这些化合物的过程。更具体地，本发明涉及一种在体内成像脑中淀粉样沉积物的方法，以允许抗死前诊断阿尔茨海默病以及测量阿尔茨海默病治疗剂的临床疗效。此外，本发明还涉及这些化合物的药学可接受的盐、组成物和使用方法。

  公开号：

  US07772256B2

文献信息

• Novel 2-Heteroaryl Substituted Benzothiophenes and Benzofuranes 709
  申请人：Arzel Erwan

  公开号：US20080221149A1

  公开（公告）日：2008-09-11

  The present invention relates to novel 2-heteroaryl substituted benzothiophene and benzofuran derivatives, precursors thereof, and therapeutic uses of such compounds, having the structural formula (Ia) below: and to their pharmaceutically acceptable salt, compositions and methods of use. Furthermore, the invention relates to novel 2-heteroaryl substituted benzothiophene and benzofuran derivatives that are suitable for imaging amyloid deposits in living patients, their compositions, methods of use and processes to make such compounds. More specifically, the present invention relates to a method of imaging amyloid deposits in brain in vivo to allow antemortem diagnosis of Alzheimer's disease as well as measureing clinical efficacy of Alzheimer's disease therapeutic agents.

  本发明涉及新型2-杂环芳基取代苯并噻吩和苯并呋喃衍生物，其前体以及这些化合物的治疗用途，具有如下结构式(Ia)： 以及它们的药用盐、组合物和使用方法。此外，本发明涉及适用于在活体患者中成像淀粉样沉积物的新型2-杂环芳基取代苯并噻吩和苯并呋喃衍生物，它们的组合物、使用方法以及制备这类化合物的过程。更具体地，本发明涉及一种在体内成像脑部淀粉样沉积物的方法，以允许在死前诊断阿尔茨海默病，并测量阿尔茨海默病治疗药物的临床疗效。
• [EN] NEW BENZOFURANS SUITABLE AS PRECURSORS TO COMPOUNDS THAT ARE USEFUL FOR IMAGING AMYLOID DEPOSITS<br/>[FR] NOUVEAUX BENZOFURANES APPROPRIÉS EN TANT QUE PRÉCURSEURS DE COMPOSÉS QUI SONT UTILES POUR L'IMAGERIE DE DÉPÔTS AMYLOÏDES
  申请人：ASTRAZENECA AB

  公开号：WO2010024769A1

  公开（公告）日：2010-03-04

  The present invention relates to novel derivatives that are suitable as precursors to compounds that are useful for imaging amyloid deposits in living patients, their compositions, methods of use and processes to make such compounds. The compounds deriving from these precursors are useful in methods of imaging amyloid deposits in brain in vivo to allow antemortem diagnosis of Alzheimer's disease by positron emission tomography (PET) as well as measuring clinical efficacy of Alzheimer's disease therapeutic agents. Furthermore, the present invention also discloses the precursor compounds in crystalline form.

  本发明涉及适用作为在活体患者中成像淀粉样沉积物有用的化合物的前体的新颖衍生物，以及这些化合物的组合物、使用方法和制备这种化合物的过程。从这些前体衍生的化合物在体内成像脑中的淀粉样沉积物的方法中有用，以允许通过正电子发射断层扫描（PET）进行阿尔茨海默病的临床前诊断，以及测量阿尔茨海默病治疗药物的临床疗效。此外，本发明还披露了结晶形式的前体化合物。
• Compounds Suitable As Precursors to Compounds that are Useful for Imaging Amyloid Deposits
  申请人：Bjõrk Seth

  公开号：US20100056796A1

  公开（公告）日：2010-03-04

  The present invention relates to novel derivatives that are suitable as precursors to compounds that are useful for imaging amyloid deposits in living patients, their compositions, methods of use and processes to make such compounds. The compounds deriving from these precursors are useful in methods of imaging amyloid deposits in brain in vivo to allow antemortem diagnosis of Alzheimer's disease by positron emission tomography (PET) as well as measuring clinical efficacy of Alzheimer's disease therapeutic agents. Furthermore, the present invention also discloses the precursor compounds in crystalline form.

  本发明涉及新型衍生物，适用于成为有用于在活体患者中成像淀粉样沉积的化合物的前体，以及它们的组成、使用方法和制造这些化合物的过程。从这些前体衍生的化合物在体内成像淀粉样沉积的方法中非常有用，以允许通过正电子发射断层扫描（PET）进行临床前诊断阿尔茨海默病，并测量阿尔茨海默病治疗药物的临床疗效。此外，本发明还披露了晶体形式的前体化合物。
• COMPOUNDS SUITABLE AS PRECURSORS TO COMPOUNDS THAT ARE USEFUL FOR IMAGING AMYLOID DEPOSITS
  申请人：AstraZeneca AB

  公开号：US20140296534A1

  公开（公告）日：2014-10-02

  The present invention relates to novel derivatives that are suitable as precursors to compounds that are useful for imaging amyloid deposits in living patients, their compositions, methods of use and processes to make such compounds. The compounds deriving from these precursors are useful in methods of imaging amyloid deposits in brain in vivo to allow antemortem diagnosis of Alzheimer's disease by positron emission tomography (PET) as well as measuring clinical efficacy of Alzheimer's disease therapeutic agents. Furthermore, the present invention also discloses the precursor compounds in crystalline form.

  本发明涉及新型衍生物，适用于成为有用于成像活体患者中淀粉样沉积物的化合物的前体，以及它们的组成、使用方法和制备这种化合物的过程。从这些前体衍生的化合物在体内成像淀粉样沉积物的方法中非常有用，可以通过正电子发射断层扫描（PET）进行抗死前诊断阿尔茨海默病，以及测量阿尔茨海默病治疗剂的临床疗效。此外，本发明还揭示了晶体形式的前体化合物。
• NOVEL 2-HETEROARYL SUBSTITUTED BENZOTHIOPHENES AND BENZOFURANES 709
  申请人：AstraZeneca AB

  公开号：EP2132201A1

  公开（公告）日：2009-12-16