3-(2-Cyanophenyl)-5-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one | 380918-26-3

• 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: 3-(2-Cyanophenyl)-5-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one
• 英文别名: 2-[5-(2-Cyanophenyl)-2-oxo-1-phenylpyridin-3-yl]benzonitrile
• CAS: 380918-26-3
• 化学式: C₂₅H₁₅N₃O
• 分子量: 373.414
• InChiKey: BGVAZWHWNRMMCN-UHFFFAOYSA-N

物化性质

• 沸点：
  661.4±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-bromo-1-phenyl-3-iodo-1,2-dihydropyridin-2-one 、 2-氰基苯硼酸 1,3-丙二醇酯 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以30%的产率得到3-(2-Cyanophenyl)-5-(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）。
• Pharmaceutical compositions comprising dihydropyridinone compounds and an immunoregulatory or an antiinflammatory agent and their uses
  申请人：Smith Terence

  公开号：US20060100249A1

  公开（公告）日：2006-05-11

  The present invention relates to compositions comprising 1,2-dihydropiridin-2-one compounds and an immunoregulatory or anti-inflammatory agent. The compositions are useful for the prevention or the treatment of neurodegenerative diseases, for example demyelinating disorders.

  本发明涉及包含1,2-二氢吡啶-2-酮化合物和免疫调节或抗炎剂的组合物。该组合物可用于预防或治疗神经退行性疾病，例如脱髓鞘性疾病。