BIA 2-256 | 78880-64-5

• 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: BIA 2-256
• 英文别名: 5-carbamoyl-10-nitro-5H-dibenz[b,f]azepine；10-Nitro-dibenz[b,f]azepin-5-carboxamide；5-nitrobenzo[b][1]benzazepine-11-carboxamide
• CAS: 78880-64-5
• 化学式: C₁₅H₁₁N₃O₃
• 分子量: 281.271
• InChiKey: ZJVRKDNTMMYIKR-UHFFFAOYSA-N

物化性质

• 沸点：
  472.4±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  BIA 2-256 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.67h， 以72%的产率得到BIA 2-254
  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：

  10-硝基-5H-二苯并[b,f]氮杂卓-5-甲腈 在 三氟化硼 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 BIA 2-256
  参考文献：
  名称：

  Process for the manufacture of

  摘要：

  该发明涉及一种制备已知的式III的5-氨基甲酰基-10-氧基-10,11-二氢-5H-二苯并[b,f]氮杂环的方法，其特征在于，例如，将式I的5-氰基-5H-二苯并[b,f]氮杂环硝化以形成式II的5-氰基-10-硝基-5H-二苯并[b,f]氮杂环，然后进行水解，然后还原，然后将反应混合物中含有的还原产物进行水解，并将式III的终产物以纯形式分离出来。该过程由以下反应方案说明：##STR1## 该发明还涉及在这些反应中产生的新中间体。

  公开号：

  US04452738A1

文献信息

• 5-Cyano- and 5-carbamoyl-10-nitro-5H-dibenz[b,f]azepine
  申请人：Ciba-Geigy Corporation

  公开号：US04540514A1

  公开（公告）日：1985-09-10

  The invention relates to a process for the manufacture of the known 5-carbamoyl-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine of the formula III which is characterized in that, for example, 5-cyano-5H-dibenz[b,f]azepine of the formula I is nitrated to form 5-cyano-10-nitro-5H-dibenz[b,f]azepine of the formula II, this is subjected to hydrolysis, then reduction, then the reduction product contained in the reaction mixture is subjected to hydrolysis and the end product of the formula III is isolated in pure form. The process is illustrated by the following reaction scheme: ##STR1## The invention relates also to new intermediates produced in these reactions.

  本发明涉及一种制造已知的式III的5-氨基甲酰基-10-氧代-10,11-二氢-5H-二苯并[b,f]氮杂烷的过程，其特征在于，例如，将式I的5-氰基-5H-二苯并[b,f]氮杂烷硝化以形成式II的5-氰基-10-硝基-5H-二苯并[b,f]氮杂烷，然后进行水解、还原，然后将反应混合物中含有的还原产物进行水解，从而分离出纯的式III的终产物。该过程由以下反应方程式说明：##STR1## 本发明还涉及在这些反应中产生的新中间体。
• 5-Cyano-10-isonitroso-10,11-dihydro-5H-dibenz[b,f]azepine
  申请人：Ciba-Geigy Corporation

  公开号：US04579683A1

  公开（公告）日：1986-04-01

  The invention relates to a process for the manufacture of the known 5-carbamoyl-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine of the formula III which is characterized in that, for example, 5-cyano-5H-dibenz[b,f]azepine of the formula I is nitrated to form 5-cyano-10-nitro-5H-dibenz[b,f]azepine of the formula II, this is subjected to hydrolysis, then reduction, then the reduction product contained in the reaction mixture is subjected to hydrolysis and the end product of the formula III is isolated in pure form. The process is illustrated by the following reaction scheme: ##STR1## The invention relates also to new intermediates produced in these reactions.

  本发明涉及一种制造已知的5-氨基甲酰基-10-氧代-10,11-二氢-5H-二苯并[b,f]氮杂葡萄糖III的方法，其特征在于，例如，将式I的5-氰基-5H-二苯并[b,f]氮杂葡萄糖硝化形成式II的5-氰基-10-硝基-5H-二苯并[b,f]氮杂葡萄糖，然后进行水解、还原，然后将反应混合物中所含的还原产物进行水解，分离出纯的式III的终产物。该过程的反应方程式如下: ##STR1## 本发明还涉及在这些反应中产生的新中间体。
• Verfahren zur Herstellung einer Oxo-Verbindung und dazu benötigte neue Zwischenprodukte
  申请人：CIBA-GEIGY AG

  公开号：EP0028028B1

  公开（公告）日：1985-05-22
• US4452738A
  申请人：——

  公开号：US4452738A

  公开（公告）日：1984-06-05
• US4540514A
  申请人：——

  公开号：US4540514A

  公开（公告）日：1985-09-10