3-氟-5-[3-(5-氟-2-吡啶基)-1,2,4-恶二唑-5-基]苄腈 | 327056-26-8

• 物质功能分类: 生物化工 - 抑制剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-氟-5-[3-(5-氟-2-吡啶基)-1,2,4-恶二唑-5-基]苄腈
• 中文别名: 3-氟-5-[3-(5-氟吡啶-2-基)-1,2,4-噁二唑-5-基]苯甲腈
• 英文名称: [3H]-AZD 9272
• 英文别名: AZD9272；3-fluoro-5-(3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl)benzonitrile；3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile；AZ'72；3-(5-fluoropyrid-2-yl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole
• CAS: 327056-26-8
• 化学式: C₁₄H₆F₂N₄O
• 分子量: 284.225
• InChiKey: RBSPCALDSNXWEP-UHFFFAOYSA-N

物化性质

• 沸点：
  446.3±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：50 mM

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  75.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-氟-5-[3-(5-氟-2-吡啶基)-1,2,4-恶二唑-5-基]苄腈 、 三甲基铝 在 叠氮基三甲基硅烷 作用下， 以 甲苯 为溶剂， 以59 mg (36%)的产率得到3-(5-fluoro-pyrid-2-yl)-5-[3-fluoro-5-(1H-tetraazol-5-yl)-phenyl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists

  摘要：

  本发明提供了作为代谢型谷氨酸受体拮抗剂的化合物和药物组合物，用于治疗神经系统疾病和障碍。还公开了制备这些化合物的方法。

  公开号：

  US20030055085A1
• 作为产物：
  描述：

  2-氰基-5-氟吡啶 在 草酰氯 、 盐酸羟胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 3-氟-5-[3-(5-氟-2-吡啶基)-1,2,4-恶二唑-5-基]苄腈
  参考文献：
  名称：

  Discovery and characterization of AZD9272 and AZD6538—Two novel mGluR5 negative allosteric modulators selected for clinical development

  摘要：

  AZD9272 and AZD6538 are two novel mGluR5 negative allosteric modulators selected for further clinical development. An initial high-throughput screening revealed leads with promising profiles, which were further optimized by minor, yet indispensable, structural modifications to bring forth these drug candidates. Advantageously, both compounds may be synthesized in as little as one step. Both are highly potent and selective for the human as well as the rat mGluR5 where they interact at the same binding site than MPEP. They are orally available, allow for long interval administration due to a high metabolic stability and long half-lives in rats and permeate the blood brain barrier to a high extent. AZD9272 has progressed into phase I clinical studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.100

文献信息

• [EN] USE OF MGLUR5 ANTAGONISTS FOR THE TREATMENT OF GERD<br/>[FR] EMPLOI D'ANTAGONISTES DE MGLUR5 POUR LE TRAITEMENT DU REFLUX GASTRO-OESOPHAGIEN
  申请人：ASTRAZENECA AB

  公开号：WO2004000316A1

  公开（公告）日：2003-12-31

  The present invention relates to the use of metabotropic glutamate receptor 5 antagonists for the inhibition of transient lower esophageal sphincter relaxations. A further aspects of the invention is directed to the use of metabotropic glutamate receptor 5 antagonists for the treatment of gastro, esophageal reflux disease, as well as for the treatment of regurgitation and asthma.

  本发明涉及使用代谢型谷氨酸受体5拮抗剂来抑制短暂性下食管括约肌松弛。本发明的另一个方面是使用代谢型谷氨酸受体5拮抗剂治疗胃食管反流病，以及治疗反流和哮喘。
• Negative allosteric modulators of MGLUR5 for use in the treatment of mature brain damages
  申请人：Sinntaxis AB

  公开号：US11033545B2

  公开（公告）日：2021-06-15

  The present disclosure relates to the use of negative allosteric modulators (NAMs) of the metabotropic glutamate receptor 5 (mGluR5) in the treatment of a mature brain damage, such as damage after stroke.

  本公开涉及代谢型谷氨酸受体 5（mGluR5）的负变构调节剂（NAMs）在治疗成熟脑损伤（如中风后的损伤）中的应用。
• Use of mglur5 antagonists for the treatment of gerd
  申请人：Lehmann Anders

  公开号：US20060128760A1

  公开（公告）日：2006-06-15

  The present invention relates to the use of metabotropic glutamate receptor 5 antagonists for the inhibition of transient lower esophageal sphincter relaxations. A further aspects of the invention is directed to the use of metabotropic glutamate receptor 5 antagonists for the treatment of gastro, esophageal reflux disease, as well as for the treatment of regurgitation and asthma.

  本发明涉及代谢型谷氨酸受体5拮抗剂用于抑制瞬时食管下括约肌松弛的用途。本发明的另一个方面涉及代谢型谷氨酸受体 5 拮抗剂用于治疗胃、食管反流病以及反流和哮喘。
• HETEROPOLYCYCLIC COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：NPS PHARMACEUTICALS, INC.

  公开号：EP1210344A1

  公开（公告）日：2002-06-05
• USE OF MGLUR5 ANTAGONISTS FOR THE TREATMENT OF GERD
  申请人：AstraZeneca AB

  公开号：EP1513525B1

  公开（公告）日：2008-05-14