N-{2-[3-(5-fluoropyridin-2-yl)-1,2-oxazol-5-yl]ethyl}-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide | 1410040-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-{2-[3-(5-fluoropyridin-2-yl)-1,2-oxazol-5-yl]ethyl}-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide
• 英文别名: N-{2-[3-(5-Fluoropyridin-2-yl)-1,2-oxazol-5-yl]ethyl}-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide；N-[2-[3-(5-fluoropyridin-2-yl)-1,2-oxazol-5-yl]ethyl]-5-methyl-2-(triazol-2-yl)benzamide
• CAS: 1410040-99-1
• 化学式: C₂₀H₁₇FN₆O₂
• 分子量: 392.392
• InChiKey: LEAAEADQCNYIDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  98.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-{2-[3-(5-fluoropyridin-2-yl)-1,2-oxazol-5-yl]ethyl}-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide 、 碘乙烷 在 raw materials 作用下， 生成 N-ethyl-N-{2-[3-(5-fluoropyridin-2-yl)-1,2-oxazol-5-yl]ethyl}-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide
  参考文献：
  名称：

  HETEROAROMATIC RING DERIVATIVE

  摘要：

  化合物的化学式为（IA）或其药学上可接受的盐，具有基于促进睡眠荷尔蒙（OX）受体拮抗剂活性，可用于治疗和预防多种疾病，包括睡眠障碍、抑郁症、焦虑症、恐慌症、精神分裂症、药物依赖、阿尔茨海默病、帕金森病、亨廷顿舞蹈症、进食障碍、疼痛、胃肠疾病、癫痫、炎症、免疫疾病、内分泌相关疾病和高血压等。

  公开号：

  US20140081025A1
• 作为产物：
  描述：

  5-氟吡啶-2-醛 在 N-氯代丁二酰亚胺 、 N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide 、 盐酸羟胺 、 sodium acetate 、 一水合肼 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 N-{2-[3-(5-fluoropyridin-2-yl)-1,2-oxazol-5-yl]ethyl}-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide
  参考文献：
  名称：

  Discovery and in vitro and in vivo profiles of N-ethyl-N-[2-[3-(5-fluoro-2-pyridinyl)-1H-pyrazol-1-yl]ethyl]-2-(2H-1,2,3-triazol-2-yl)-benzamide as a novel class of dual orexin receptor antagonist

  摘要：

  Orexins play an important role in sleep/wake regulation, and orexin receptor antagonists are a focus of novel therapy for the treatment of insomnia. We identified 27e (TASP0428980) as a potent dual orexin receptor antagonist through the systematic modification of our original designed lead A. We demonstrated the potent sleep-promoting effects of 27e at ip dose of 3 mg/kg in a rat polysomnogram study. 27e exhibited relatively short half-life profiles in rats and dogs. Furthermore, accumulating evidence regarding ADME profiles indicates that the predicted human half-life of 27e should be 1.2-1.4 h. These data indicated that 27e has a short-acting hypnotic property, suggesting that 27e might be useful for treating primary insomnia while exhibiting a low risk of next-day residual somnolence. Thus, 27e and its related compounds should be further evaluated to enable advancement to clinical trials. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.044

文献信息

• HETEROAROMATIC RING DERIVATIVE
  申请人：Suzuki Ryo

  公开号：US20140081025A1

  公开（公告）日：2014-03-20

  The compound represented by formula (IA) or a pharmaceutically acceptable salt thereof is based on orexin (OX) receptor antagonist activity, is useful in the treatment and prevention of illnesses including sleep disorder, depression, anxiety disorder, panic disorder, schizophrenia, drug dependency, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorders, pain, gastrointestinal disease, epilepsy, inflammation, immunological disease, endocrinological related disease, and hypertension.

  由化学式（IA）表示的化合物或其药用可接受的盐基于促进睡眠激素（OX）受体拮抗活性，在治疗和预防疾病方面具有用途，包括睡眠障碍、抑郁症、焦虑症、恐慌症、精神分裂症、药物依赖、阿尔茨海默病、帕金森病、亨廷顿舞蹈症、进食障碍、疼痛、胃肠疾病、癫痫、炎症、免疫疾病、内分泌相关疾病和高血压。
• [EN] HETEROAROMATIC RING DERIVATIVE<br/>[FR] DÉRIVÉ À CYCLE HÉTÉROAROMATIQUE
  申请人：TAISHO PHARMA CO LTD

  公开号：WO2012153729A1

  公开（公告）日：2012-11-15

  　式（ＩＡ）で示される化合物又はその医薬上許容される塩は、オレキシン（ＯＸ）受容体拮抗作用に基づいた、睡眠障害、うつ病、不安障害、パニック障害、統合失調症、薬物依存症、アルツハイマー病、パーキンソン病、ハンチントン舞踏病、摂食障害、疼痛、消化器疾患、てんかん、炎症、免疫関連疾患、内分泌関連疾患、高血圧等の疾患の治療又は予防に有用である。
• Discovery and in vitro and in vivo profiles of N-ethyl-N-[2-[3-(5-fluoro-2-pyridinyl)-1H-pyrazol-1-yl]ethyl]-2-(2H-1,2,3-triazol-2-yl)-benzamide as a novel class of dual orexin receptor antagonist
  作者：Ryo Suzuki、Dai Nozawa、Aya Futamura、Rie Nishikawa-Shimono、Masahito Abe、Nobutaka Hattori、Hiroshi Ohta、Yuko Araki、Daiji Kambe、Mari Ohmichi、Seiken Tokura、Takeshi Aoki、Norikazu Ohtake、Hiroshi Kawamoto

  DOI：10.1016/j.bmc.2015.01.044

  日期：2015.3

  Orexins play an important role in sleep/wake regulation, and orexin receptor antagonists are a focus of novel therapy for the treatment of insomnia. We identified 27e (TASP0428980) as a potent dual orexin receptor antagonist through the systematic modification of our original designed lead A. We demonstrated the potent sleep-promoting effects of 27e at ip dose of 3 mg/kg in a rat polysomnogram study. 27e exhibited relatively short half-life profiles in rats and dogs. Furthermore, accumulating evidence regarding ADME profiles indicates that the predicted human half-life of 27e should be 1.2-1.4 h. These data indicated that 27e has a short-acting hypnotic property, suggesting that 27e might be useful for treating primary insomnia while exhibiting a low risk of next-day residual somnolence. Thus, 27e and its related compounds should be further evaluated to enable advancement to clinical trials. (C) 2015 Elsevier Ltd. All rights reserved.