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

文献信息

• Synthesis, anticonvulsant properties and pharmacokinetic profile of novel 10,11-dihydro-10-oxo-5H-dibenz/b,f/azepine-5-carboxamide derivatives
  作者：David A Learmonth、Jan Benes、António Parada、Dominik Hainzl、Alexander Beliaev、Maria João Bonifácio、Pedro M Matias、Maria A Carrondo、José Garrett、Patrı́cio Soares-da-Silva

  DOI：10.1016/s0223-5234(01)01220-x

  日期：2001.3

  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.
• Derivatives of 10, 11-Dihydro-10-OXO-5H-Dibenz/B,F/Azepine-5-carboxamide
  申请人：Portela & Ca., S.A.

  公开号：US05866566A1

  公开（公告）日：1999-02-02

  Compounds of general formula I are described ##STR1## as is a process for their preparation which consists of reacting a compound of formula II ##STR2## with hydroxylamine or its derivatives of formula III H.sub.2 NOR.sup.2 (III) The compounds cited in the present invention have valuable pharmaceutical properties namely in the treatment of some disturbances in the central and peripheral nervous system.

  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。