10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide
• 英文别名: BIA 2-024；5-hydroxyimino-6H-benzo[b][1]benzazepine-11-carboxamide
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: VKSIBVBEGLEBSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide 以 水 、 乙腈 为溶剂， 以16.8%的产率得到(Z)-10,11-dihydro-10-hydroxyimino-5H-dibenzo[b,f]azepine-5-carboxamide
  参考文献：
  名称：

  Synthesis, anticonvulsant properties and pharmacokinetic profile of novel 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide derivatives

  摘要：

  A series of novel derivatives of oxcarbazepine (5), 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide was synthesised and evaluated for their anticonvulsant activity and sodium channel blocking properties. The oxime 8 was found to be the most active compound from this series, displaying greater potency than its geometric isomer 9 and exhibiting also the highest protective index value. Importantly, the metabolic profile of 8 differs from the already established dibenz/b,f/azepine-5-carboxamide drugs such as 1 and 5 which undergo rapid and complete conversion in vivo to several biologically active metabolites. In contrast 8 is metabolised to only a very minor extent leading to the conclusion that the observed anti-convulsant effect is solely attributable to 8. It is concluded that 8 may be as effective as 1 and 5 at controlling seizures and that the low toxicity and consequently high protective index should provide the compound with an improved side-effect profile. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01220-x
• 作为产物：
  描述：

  奥卡西平 、 盐酸羟胺 、 吡啶 在 乙醇 、 水 、 二氯甲烷 、 盐酸 、 碳酸氢钠 、 Brine 、 Sodium sulfate-III 作用下， 以 alcohol 为溶剂， 反应 1.0h， 以to give the desired compound as a white powder of m.p. 230.4° to 231.5° C.的产率得到10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide
  参考文献：
  名称：

  Derivatives of 10, 11-Dihydro-10-OXO-5H-Dibenz/B,F/Azepine-5-carboxamide

  摘要：

  本发明描述了一般式为I的化合物：##STR1## 以及一种制备它们的方法，该方法包括将式II的化合物##STR2## 与羟胺或其衍生物式III H.sub.2 NOR.sup.2 (III) 反应。本发明中所述的化合物具有有价值的药物特性，特别是在治疗中枢和周围神经系统的某些障碍方面。

  公开号：

  US05866566A1