5-氟-4-氧代-1H-喹啉-3-羧酸乙酯 | 655236-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 5-氟-4-氧代-1H-喹啉-3-羧酸乙酯
• 英文名称: ethyl 5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: ethyl 5-fluoro-4-oxo-1H-quinoline-3-carboxylate
• CAS: 655236-29-6
• 化学式: C₁₂H₁₀FNO₃
• 分子量: 235.215
• InChiKey: YKMHZVBKYDKXQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氟-4-氧代-1H-喹啉-3-羧酸乙酯 在 potassium carbonate 、 potassium iodide 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-fluoro-1-[(1-methyl-1H-indazol-5-yl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Fused heterocyclic M1 positive allosteric modulators

  摘要：

  Fused aromatics such as naphthalene were identified as highly potent and CNS penetrant M-1 positive allosteric modulators during an SAR study to replace the phenyl B-ring linkage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.028
• 作为产物：
  描述：

  8-溴-5-氟-4-氧代-1H-喹啉-3-羧酸乙酯 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 水 为溶剂， 20.0 ℃ 、689.49 kPa 条件下， 以36%的产率得到5-氟-4-氧代-1H-喹啉-3-羧酸乙酯
  参考文献：
  名称：

  WO2008/2621

  摘要：

  公开号：

文献信息

• [EN] FUSED HETEROCYCLIC M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS<br/>[FR] MODULATEURS DE RÉCEPTEUR M1 ALLOSTÉRIQUES POSITIFS HÉTÉROCYCLIQUES CONDENSÉS
  申请人：MERCK SHARP & DOHME

  公开号：WO2010047990A1

  公开（公告）日：2010-04-29

  The present invention is directed to fused heterocyclic compounds of formula (I): which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.

  本发明涉及式（I）的融合杂环化合物，它们是M1受体正向变构调节剂，并且在治疗M1受体参与的疾病，如阿尔茨海默病、精神分裂症、疼痛或睡眠障碍方面有用。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物和组合物治疗M1受体介导的疾病。
• FUSED HETEROCYCLIC M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS
  申请人：Kuduk Scott D.

  公开号：US20110201607A1

  公开（公告）日：2011-08-18

  The present invention is directed to fused heterocyclic compounds of formula (I): which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.

  本发明涉及公式(I)的融合杂环化合物，其为M1受体正向变构调节剂，可用于治疗M1受体参与的疾病，如阿尔茨海默病、精神分裂症、疼痛或睡眠障碍。本发明还涉及包含该化合物的药物组合物，以及该化合物和组合物在治疗M1受体介导的疾病中的使用。
• QUINOLINONE-PYRAZOLONE M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS
  申请人：Beshore Douglas C.

  公开号：US20120196845A1

  公开（公告）日：2012-08-02

  The present invention is directed to quinolinone-pyrazolone compounds of formula (I) which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.

  本发明涉及公式（I）的喹啉酮-吡唑酮化合物，它们是M1受体正向变构调节剂，可用于治疗M1受体参与的疾病，如阿尔茨海默病、精神分裂症、疼痛或睡眠障碍。本发明还涉及包括上述化合物的制药组合物，以及在治疗M1受体介导的疾病中使用上述化合物和组合物的方法。
• Fused heterocyclic M1 receptor positive allosteric modulators
  申请人：Kuduk Scott D.

  公开号：US08436016B2

  公开（公告）日：2013-05-07

  The present invention is directed to fused heterocyclic compounds of formula (I): which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.

  本发明涉及以下式（I）的融合杂环化合物，其是M1受体正向变构调节剂，可用于治疗与M1受体有关的疾病，如阿尔茨海默病、精神分裂症、疼痛或睡眠障碍。本发明还涉及包含该化合物的制药组合物，以及使用该化合物和组合物治疗由M1受体介导的疾病。
• An NMR Study of Halogenated 1,4-Dihydro-1-ethyl-4-oxoquinoline-3-carboxylates
  作者：B. Podányi、G. Keresztúri、L. Vasvári-Debreczy、I. Hermecz、G. Tóth

  DOI：10.1002/(sici)1097-458x(199611)34:11<972::aid-omr994>3.0.co;2-9

  日期：1996.11

  Ethyl 1,4-dihydro-1-ethyl-4-oxoquinoline-3-carboxylate and 29 of its mono-, di- and tri-fluoro and/or -chloro derivatives were synthesized and their H-1, C-13 and F-19 NMR spectra were recorded. H-1,C-13 and F-19 chemical shifts, J(HH), J(FH), J(CF) and J(FF) coupling constants are reported. The C-13 substituent chemical shift values of the chloro and fluoro substituents were calculated by linear multiple regression.