5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one | 381233-77-8

• 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-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one
• 英文别名: 3-(2-Cyanophenyl)-1-phenyl-5-bromo-1,2-dihydropyridin-2-one；2-(5-bromo-2-oxo-1-phenylpyridin-3-yl)benzonitrile
• CAS: 381233-77-8
• 化学式: C₁₈H₁₁BrN₂O
• 分子量: 351.202
• InChiKey: MECNIGGKZPCOJT-UHFFFAOYSA-N

物化性质

• 沸点：
  506.5±50.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one 、 2-硝基苯基硼酸 在 三苯基膦钯 caesium carbonate 作用下， 以 N-甲基乙酰胺 为溶剂， 生成 3-(2-Cyanophenyl)-5-(2-nitrophenyl)-1-phenyl-1,2-dihydropyridin-2-one
  参考文献：
  名称：

  1,2-DIHYDROPYRIDINE COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF

  摘要：

  公开号：

  EP1300396B1
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 在 四(三苯基膦)钯 、 硫酸 、 碘 、 copper diacetate 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 202.0h， 生成 5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one
  参考文献：
  名称：

  Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (Perampanel): A Novel, Noncompetitive α-Amino-3-hydroxy-5-methyl-4-isoxazolepropanoic Acid (AMPA) Receptor Antagonist

  摘要：

  Dysfunction of glutamatergic neurotransmission has been implicated in the pathogenesis of epilepsy and numerous other neurological diseases. Here we describe the discovery of a series of 1,3,5-triaryl-1H-pyridin-2-one derivatives as noncompetitive antagonists of AMPA-type ionotropic glutamate receptors. The structure-activity relationships for this series of compounds were investigated by manipulating individual aromatic rings located at positions 1, 3, and 5 of the pyridone ring. This culminated in the discovery of 2-(2-oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile (perampanel, 6), a novel, noncompetitive AMPA receptor antagonist that showed potent activity in an in vitro AMPA-induced Ca2+ influx assay (IC50 = 60 nM) and in an in vivo AMPA-induced seizure model (minimum effective dose of 2 mg/kg po). Perampanel is currently in regulatory submission for partial-onset seizures associated with epilepsy.

  DOI：

  10.1021/jm301268u

文献信息

• 1,3,5-Trisubstituted 2(1H)-pyridones as AMPA receptor inhibitors useful for the treatment of eg Parkinson's disease
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2053041A2

  公开（公告）日：2009-04-29

  The present invention provides a novel compound having an excellent AMPA receptor inhibitory action and/or kainate inhibitory action. A compound represented by the following formula, a salt thereof or hydrates thereof. In the formula, Q indicates NH, O or S; and R1, R2, R3, R4 and R5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C1-6alkyl group or a group represented by the formula -X-A (wherein X indicates a single bond, an optionally sbutituted C1-6 alkylene group etc.; and A indicates an optionally substituted C6-14 aromatic hydrocarbocyclic group or 5- to 14-membered aromatic heterocyclic group etc.).

  本发明提供了一种新的化合物，具有出色的AMPA受体抑制作用和/或kainate抑制作用。该化合物由以下公式所表示，其盐或水合物。在公式中，Q表示NH，O或S; R1、R2、R3、R4和R5相同或不同，每个表示氢原子、卤原子、C1-6烷基或由公式-X-A表示的基团（其中X表示单键、可选择的取代C1-6烷基等; A表示可选择的取代C6-14芳香族烃环基或5-至14环芳香族杂环基等）。
• 1, 2-Dihydropyridine compounds, manufacturing method thereof and use thereof
  申请人：Nagato Satoshi

  公开号：US20050245581A1

  公开（公告）日：2005-11-03

  The present invention provides a novel compound having an excellent AMPA receptor inhibitory action and/or kainate inhibitory action. A compound represented by the following formula, a salt thereof or hydrates thereof. In the formula, Q indicates NH, O or S; and R 1 , R 2 , R 3 , R 4 and R 5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C 1-6 alkyl group or a group represented by the formula —X-A (wherein X indicates a single bond, an optionally sbutituted C 1-6 alkylene group etc.; and A indicates an optionally substituted C 6-14 aromatic hydrocarbocyclic group or 5- to 14-membered aromatic heterocyclic group etc.).

  本发明提供了一种新型化合物，具有出色的AMPA受体抑制作用和/或卡因酸受体抑制作用。该化合物由以下公式表示，其盐或水合物。在该公式中，Q表示NH，O或S；R1，R2，R3，R4和R5彼此相同或不同，每个表示氢原子，卤素原子，C1-6烷基或由公式—X-A表示的基团（其中X表示单键，可选取代的C1-6烷基等；A表示可选取代的C6-14芳香烃环基或5-至14元芳香杂环基等）。
• 1,5-Di(aryl or heteroaryl)-3-halo-2(1H)-pyridones as intermediates for the preparation of AMPA receptor inhibitors
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2177520A1

  公开（公告）日：2010-04-21

  The present invention provides compounds represented by the formula: or a salt thereof, wherein, each A1a and A3a are the same as or different from each other and each indicates an optionally substituted C6-14 aromatic hydrocarbocyclic group or 5 to 14-membered aromatic heterocyclic group; and W represents a halogen atom. The compounds are intermediates for the preparation of inhibitors of the AMPA receptor.

  本发明提供了以下式子或其盐的化合物，其中A1a和A3a分别相同或不同，每个表示一个选择性取代的C6-14芳香族烃环基或5至14元芳香族杂环基；W表示卤素原子。这些化合物是AMPA受体抑制剂的中间体。
• 1,2-Dihydropyridine compounds, process for preparation of the same and use thereof
  申请人：——

  公开号：US20040023973A1

  公开（公告）日：2004-02-05

  The present invention provides a novel compound having an excellent AMPA receptor inhibitory action and/or kainate inhibitory action. A compound represented by the following formula, a salt thereof or hydrates thereof. 1 In the formula, Q indicates NH, O or S; and R 1 , R 2 , R 3 , R 4 and R 5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C 1-6 alkyl group or a group represented by the formula —X-A (wherein X indicates a single bond, an optionally sbutituted C 1-6 alkylene group etc.; and A indicates an optionally substituted C 6-14 aromatic hydrocarbocyclic group or 5- to 14-membered aromatic heterocyclic group etc.).

  本发明提供了一种新型化合物，具有出色的AMPA受体抑制作用和/或kainate抑制作用。该化合物由以下公式表示，其盐或水合物。 1在公式中，Q表示NH，O或S；R1，R2，R3，R4和R5相同或不同，每个表示氢原子，卤素原子，C1-6烷基或由公式表示的基团-X-A（其中X表示单键，可选地取代的C1-6烷基等；A表示可选取代的C6-14芳香烃环基或5-至14元芳香杂环基等）。
• PROCESS FOR THE PREPARATION OF PERAMPANEL
  申请人：TEVA PHARMACEUTICALS INTERNATIONAL GMBH

  公开号：US20160176842A1

  公开（公告）日：2016-06-23

  The present invention provides intermediates useful for the synthesis of Perampanel and processes employing said intermediates for preparing Perampanel. The invention also provides processes for making the intermediates, crystalline forms of the intermediates and the use of the crystalline forms for preparing Perampanel.

  本发明提供了用于合成Perampanel的中间体和采用该中间体制备Perampanel的过程。该发明还提供制备中间体的过程，中间体的晶体形态以及使用晶体形态制备Perampanel的方法。