5-fluoro-2,3-dihydrofuro[2,3-b]pyridine | 1356542-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-fluoro-2,3-dihydrofuro[2,3-b]pyridine
• CAS: 1356542-41-0
• 化学式: C₇H₆FNO
• 分子量: 139.129
• InChiKey: OMJWYWHQUXAICD-UHFFFAOYSA-N

物化性质

• 沸点：
  208.5±40.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-fluoro-2,3-dihydrofuro[2,3-b]pyridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以72%的产率得到5-Fluoro-7-oxido-2,3-dihydrofuro[2,3-b]pyridin-7-ium
  参考文献：
  名称：

  [EN] OGA INHIBITOR COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS D'OGA

  摘要：

  本发明涉及O-GlcNAc水解酶（OGA）抑制剂。该发明还涉及包含这类化合物的药物组合物，制备这类化合物和组合物的方法，以及利用这类化合物和组合物预防和治疗抑制OGA有益的疾病的用途，例如tau病变，特别是阿尔茨海默病或进行性核上性麻痹症；以及伴有tau病理的神经退行性疾病，特别是由C90RF72突变引起的肌萎缩侧索硬化或额颞叶痴呆症。

  公开号：

  WO2019243527A1
• 作为产物：
  描述：

  2-(but-3-ynyloxy)-5-fluoropyrimidine 在 sodium hydroxide 作用下， 以 3-戊酮 、 甲苯 为溶剂， 以65%的产率得到5-fluoro-2,3-dihydrofuro[2,3-b]pyridine
  参考文献：
  名称：

  过热连续流动条件下分子内逆电子需求杂-狄尔斯-阿尔德反应合成环状吡啶

  摘要：

  嘧啶炔烃可以在流动中有效地转化为相应的环状吡啶。有机溶剂的过热远远超过其沸点，使得通常用于这些反应的硝基苯或氯苯等有毒且难以处理的溶剂被毒性较小的溶剂（如甲苯）取代。研究了一系列结构接近的起始材料的相对反应速率，并开发了一种可扩展的流动工艺，为获得一系列新型环状吡啶结构单元提供了便利。发现在过热条件下溶剂的热体积膨胀的影响是显着的并且显着地影响了停留时间。为了获得有意义和准确的停留时间，需要针对体积膨胀校正流速。

  DOI：

  10.1002/ejoc.201101538

文献信息

• [EN] PYRROLIDINE AND BICYCLOHETEROARYL CONTAINING OGA INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS D'OGA CONTENANT DE LA PYRROLIDINE ET DE LA BICYCLOHÉTÉROARYLE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021094312A1

  公开（公告）日：2021-05-20

  The present invention relates to O-GIcNAc hydrolase (OGA) inhibitors. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which inhibition of OGA is beneficial, such as tauopathies, in particular Alzheimer's disease or progressive supranuclear palsy; and neurodegenerative diseases accompanied by a tau pathology, in particular amyotrophic lateral sclerosis or frontotemporal lobe dementia caused by C90RF72 mutations; or alpha synucleinopathies, in particular Parkinson's disease, dementia due to Parkinson's (or neurocognitive disorder due to Parkinson's disease), dementia with Lewy bodies, multiple system atrophy, or alpha synucleinopathy caused by Gaucher's disease.

  本发明涉及O-GIcNAc水解酶（OGA）抑制剂。该发明还涉及包含这类化合物的药物组合物，制备这类化合物和组合物的方法，以及利用这类化合物和组合物预防和治疗抑制OGA有益的疾病，如tau病变，特别是阿尔茨海默病或进行性上行性麻痹；以及伴有tau病理的神经退行性疾病，特别是由C90RF72突变引起的肌萎缩侧索硬化或额颞叶痴呆；或α-突触核蛋白病，特别是帕金森病，由帕金森病引起的痴呆（或由帕金森病引起的神经认知障碍），具有Lewy小体的痴呆，多系统萎缩，或由高雪氏病引起的α-突触核蛋白病。
• OGA INHIBITOR COMPOUNDS
  申请人：Janssen Pharmaceutica NV

  公开号：EP3810593A1

  公开（公告）日：2021-04-28
• [EN] OGA INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE L'OGA
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2019243526A1

  公开（公告）日：2019-12-26

  The present invention relates to O-GlcNAc hydrolase (OGA) inhibitors. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which inhibition of OGA is beneficial, such as tauopathies, in particular Alzheimer's disease or progressive supranuclear palsy; and neurodegenerative diseases accompanied by a tau pathology, in particular amyotrophic lateral sclerosis or frontotemporal lobe dementia caused by C90RF72 mutations.
• [EN] OGA INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS D'OGA
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021123291A1

  公开（公告）日：2021-06-24

  The present invention relates to O-GlcNAc hydrolase (OGA) inhibitors. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which inhibition of OGA is beneficial, such as tauopathies, in particular Alzheimer's disease or progressive supranuclear palsy; and neurodegenerative diseases accompanied by a tau pathology, in particular amyotrophic lateral sclerosis or frontotemporal lobe dementia caused by C9ORF72 mutations; or alpha synucleinopathies, in particular Parkinson's disease, dementia due to Parkinson's (or neurocognitive disorder due to Parkinson's disease), dementia with Lewy bodies, multiple system atrophy, or alpha synucleinopathy caused by Gaucher's disease.

  本发明涉及O-GlcNAc水解酶（OGA）抑制剂。该发明还涉及包含这类化合物的药物组合物，制备这类化合物和组合物的方法，以及利用这类化合物和组合物预防和治疗抑制OGA有益的疾病的用途，例如tau病变，特别是阿尔茨海默病或进行性上行性核瘫痪；以及伴有tau病理的神经退行性疾病，特别是由C9ORF72突变引起的肌萎缩侧索硬化或额颞叶痴呆；或α-突触核蛋白病，特别是帕金森病、帕金森病引起的痴呆（或由帕金森病引起的神经认知障碍）、带有Lewy小体的痴呆、多系统萎缩，或由高雪氏病引起的α-突触核蛋白病。
• Synthesis of Annulated Pyridines by Intramolecular Inverse-Electron-Demand Hetero-Diels-Alder Reaction under Superheated Continuous Flow Conditions
  作者：Rainer E. Martin、Falk Morawitz、Christoph Kuratli、André M. Alker、Alexander I. Alanine

  DOI：10.1002/ejoc.201101538

  日期：2012.1

  materials was investigated and a scalable flow process was developed, providing facile access to a series of novel annulated pyridine building blocks. The effect of thermal volume expansion of solvents under superheated conditions was found to be significant and influenced the residence times considerably. To obtain meaningful and accurate residence times, flow rates need to be corrected for volume expansion

  嘧啶炔烃可以在流动中有效地转化为相应的环状吡啶。有机溶剂的过热远远超过其沸点，使得通常用于这些反应的硝基苯或氯苯等有毒且难以处理的溶剂被毒性较小的溶剂（如甲苯）取代。研究了一系列结构接近的起始材料的相对反应速率，并开发了一种可扩展的流动工艺，为获得一系列新型环状吡啶结构单元提供了便利。发现在过热条件下溶剂的热体积膨胀的影响是显着的并且显着地影响了停留时间。为了获得有意义和准确的停留时间，需要针对体积膨胀校正流速。