perphenazine N-Boc-4-aminobutyrate | 503537-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: perphenazine N-Boc-4-aminobutyrate
• 英文别名: 2-[4-[3-(2-Chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 503537-30-2
• 化学式: C₃₀H₄₁ClN₄O₄S
• 分子量: 589.199
• InChiKey: FRMWLKOZSLBKLP-UHFFFAOYSA-N

物化性质

• 沸点：
  707.1±60.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  perphenazine N-Boc-4-aminobutyrate 在 甲烷磺酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 4-amino-butyric acid 2-{4-[3-(2-chloro-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethyl ester
  参考文献：
  名称：

  WO2006/131923

  摘要：

  公开号：
• 作为产物：
  描述：

  奋乃静 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以63%的产率得到perphenazine N-Boc-4-aminobutyrate
  参考文献：
  名称：

  WO2006/131923

  摘要：

  公开号：

文献信息

• Crystalline Forms of the Tri-Mesylate Salt of Perphenazine-Gaba and Process of Producing the Same
  申请人：Nudelman Abraham

  公开号：US20110312948A1

  公开（公告）日：2011-12-22

  Novel crystalline form of perphenazine 4-aminobutyrate trimesylate and a process of producing the same are disclosed. The novel crystalline form is characterized by a unique XRPD pattern and a DSC that exhibits an endothermic peak at a relatively high temperature (e.g., higher than 209° C.). Also disclosed are a process of preparing perphenazine 4-aminobutyrate trimesylate by in situ deprotection and salification, in a single-step synthesis, and a highly pure perphenazine 4-aminobutyrate trimesylate obtained thereby. Uses of any of the described perphenazine 4-aminobutyrate trimesylate are also disclosed.

  揭示了新型晶体形式的perphenazine 4-aminobutyrate trimesylate及其生产方法。该新型晶体形式的特征是具有独特的XRPD图案和DSC，在相对较高温度（例如高于209°C）显示出一个吸热峰。还揭示了一种通过原位去保护和盐化的单步合成方法制备perphenazine 4-aminobutyrate trimesylate，以及由此获得的高纯度perphenazine 4-aminobutyrate trimesylate。还揭示了任何所述perphenazine 4-aminobutyrate trimesylate的用途。
• A Mutual Prodrug Ester of GABA and Perphenazine Exhibits Antischizophrenic Efficacy with Diminished Extrapyramidal Effects
  作者：Abraham Nudelman、Irit Gil-Ad、Nava Shpaisman、Igor Terasenko、Hanna Ron、Kinneret Savitsky、Yona Geffen、Abraham Weizman、Ada Rephaeli

  DOI：10.1021/jm7012453

  日期：2008.5.1

  The perphenazine and fluphenazine GABA esters 3 and 4 evaluated in rat models for antipsychotic activity displayed a significant decrease of catalepsy associated with increased prolactin blood levels. Efficacy was evaluated in the D-amphetamine-induced hyperactivity model, where perphenazine abolished hyperactivity and induced sedation and catalepsy, whereas 3 reduced hyperactivity without sedation or catalepsy. Thus, 3 (BL-1020) constitutes a prototype of novel antipsychotics possessing GABAergic activity. A phase II study is in progress.
• NOVEL SALTS OF CONJUGATED PSYCHOTROPIC DRUGS AND PROCESSES OF PREPARING SAME
  申请人：Ramot at Tel Aviv University Ltd.

  公开号：EP1888120B1

  公开（公告）日：2012-12-05
• Novel salts of conjugated psychotropic drugs and processes of preparing same
  申请人：Nudelman Abraham

  公开号：US20090298814A1

  公开（公告）日：2009-12-03

  Novel chemical conjugates of a psychotropic drug residue and an amino-containing organic acid residue selected to reduce side effects induced by the psychotropic drug when administered per se, to enhance the therapeutic activity of the psychotropic drug and/or to exert anti-proliferative activity, in which the amino group is in the form of an acid addition salt thereof and which are characterized by high stability are disclosed. Further disclosed are processes for preparing the chemical conjugates and addition salts thereof, pharmaceutical compositions containing the chemical conjugates and methods utilizing the chemical conjugates for treating various medical conditions.
• CRYSTALLINE FORMS OF THE TRI-MESYLATE SALT OF PERPHENAZINE-GABA AND PROCESS OF PRODUCING THE SAME
  申请人：Ramot at Tel-Aviv University Ltd.

  公开号：US20130150352A1

  公开（公告）日：2013-06-13

  Novel crystalline form of perphenazine 4-aminobutyrate trimesylate and a process of producing the same are disclosed. The novel crystalline form is characterized by a unique XRPD pattern and a DSC that exhibits an endothermic peak at a relatively high temperature (e.g., higher than 209° C.). Also disclosed are a process of preparing perphenazine 4-aminobutyrate trimesylate by in situ deprotection and salification, in a single-step synthesis, and a highly pure perphenazine 4-aminobutyrate trimesylate obtained thereby. Uses of any of the described perphenazine 4-aminobutyrate trimesylate are also disclosed.