5-methyl-3-pyridin-3-yl-isoxazole-4-carboxylic acid ethyl ester | 954230-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-methyl-3-pyridin-3-yl-isoxazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-Methyl-3-(3-pyridyl)isoxazole-4-carboxylate；ethyl 5-methyl-3-pyridin-3-yl-1,2-oxazole-4-carboxylate
• CAS: 954230-47-8
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: FKANTPPJUCNLPG-UHFFFAOYSA-N

物化性质

• 沸点：
  394.5±42.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-3-pyridin-3-yl-isoxazole-4-carboxylic acid ethyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-甲基-3-(3-吡啶基)-1,2-恶唑-4-羧酸
  参考文献：
  名称：

  Isoxazolopyridone derivatives as allosteric metabotropic glutamate receptor 7 antagonists

  摘要：

  This Letter describes the synthesis and evaluation of mGluR7 antagonists in the isoxazolopyridone series. In the course of modi. cation in this class, novel solid support synthesis of the isoxazolopyridone scaffold was developed. Subsequent chemical modi. cation led to the identification of several potent derivatives with improved physicochemical properties compared to a hit compound 1. Among these, 2 showed good oral bioavailability and brain penetrability, suggesting that 2 may be useful for in vivo study to elucidate the role of mGluR7. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.070
• 作为产物：
  描述：

  3-(1-吡咯烷基)巴豆酸乙酯 、 3-吡啶醛肟 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 5-methyl-3-pyridin-3-yl-isoxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Isoxazolopyridone derivatives as allosteric metabotropic glutamate receptor 7 antagonists

  摘要：

  This Letter describes the synthesis and evaluation of mGluR7 antagonists in the isoxazolopyridone series. In the course of modi. cation in this class, novel solid support synthesis of the isoxazolopyridone scaffold was developed. Subsequent chemical modi. cation led to the identification of several potent derivatives with improved physicochemical properties compared to a hit compound 1. Among these, 2 showed good oral bioavailability and brain penetrability, suggesting that 2 may be useful for in vivo study to elucidate the role of mGluR7. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.070

文献信息

• ISOXAZOLE-PYRIDINE DERIVATIVES
  申请人：Buettelmann Bernd

  公开号：US20090143371A1

  公开（公告）日：2009-06-04

  The present invention is concerned with isoxazole-pyridine derivatives of formula I wherein X, R 1 to R 6 are as described herein. The compounds are active on the GABA A α5 receptor binding site and useful for the treatment of cognitive disorders, such as Alzheimer's disease.

  本发明涉及式I的异恶唑-吡啶衍生物 其中X，R1至R6如本文所述。这些化合物对GABA A α5受体结合位点具有活性，并可用于治疗认知障碍，如阿尔茨海默病。
• ISOXAZOLO-PYRIDINE DERIVATIVES
  申请人：HOFFMANN-LA ROCHE INC.

  公开号：US20130274468A1

  公开（公告）日：2013-10-17

  The present invention is concerned with isoxazole-pyridine derivatives of formula I wherein X, R 1 to R 6 are as described herein. The compounds are active on the GABA A α5 receptor binding site and useful for the treatment of cognitive disorders, such as Alzheimer's disease.

  本发明涉及公式I中的异恶唑-吡啶衍生物，其中X，R1至R6如此描述。这些化合物在GABA A α5受体结合位点上活性，并且用于治疗认知障碍，例如阿尔茨海默病。
• Isoxazolo-pyridine derivatives
  申请人：Roche Palo Alto LLC

  公开号：US08877782B2

  公开（公告）日：2014-11-04

  The present invention is concerned with isoxazole-pyridine derivatives of formula I wherein X, R1 to R6 are as described herein. The compounds are active on the GABA A α5 receptor binding site and useful for the treatment of cognitive disorders, such as Alzheimer's disease.

  本发明涉及式I的异噁唑-吡啶衍生物，其中X，R1至R6如本文所述。该化合物对GABA A α5受体结合位点具有活性，可用于治疗认知障碍，如阿尔茨海默病。
• Isoxazolyl ether derivatives as GABAA α5 PAM
  申请人：Hoffmann-La Roche Inc.

  公开号：US11091471B2

  公开（公告）日：2021-08-17

  Compounds having the formula (I) wherein R1, R2, R3, R4, R5, R6, X, Y and Z are as described herein, compositions including the compounds and methods of using the compounds.

  具有式 (I) 的化合物 其中 R1、R2、R3、R4、R5、R6、X、Y 和 Z 如本文所述。
• NEW ISOXAZOLYL ETHER DERIVATIVES AS GABA A ALPHA5 PAM
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3551627A1

  公开（公告）日：2019-10-16