Lecozotan hydrochloride | 433282-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: Lecozotan hydrochloride
• 英文别名: (R)-4-cyano-N-{2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)]-1-piperazinyl-propyl}-N-(2-pyridinyl)-benzamide hydrochloride；4-cyano-N-{(2R)-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-propyl}-N-pyridin-2-yl-benzamide hydrochloride；(R)-4-Cyano-N-{2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-propyl}-N-pyridin-2-yl-benzamide hydrochloride；4-cyano-N-[(2R)-2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propyl]-N-pyridin-2-ylbenzamide;hydrochloride
• CAS: 433282-68-9
• 化学式: C₂₈H₂₉N₅O₃*ClH
• 分子量: 520.031
• InChiKey: GXYZREDEYDFJPT-ZMBIFBSDSA-N

物化性质

• 熔点：
  239-240 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2,3-二氢-1,4-苯并二烷-5-基)哌嗪盐酸盐 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 94.0h， 生成 Lecozotan hydrochloride
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Benzodioxanylpiperazine Derivatives as Potent Serotonin 5-HT_1A Antagonists:  The Discovery of Lecozotan

  摘要：

  A series of benzodioxanylpiperazine derivatives possessing a 4-aryl amide substituent was prepared and evaluated for 5-HT1A affinity and functional antagonist activity in vitro and in vivo. All of the compounds in this series possessed high affinity for the human 5-HT1A receptor and many displayed potent antagonist activity in vitro and varying degrees of intrinsic activity in vivo. Compound 11c (Lecozotan) was selected for further development and is currently in clinical trials.

  DOI：

  10.1021/jm049493z

文献信息

• Process for preparing N-aryl-piperazine derivatives
  申请人：Chan Wai-Yin Anita

  公开号：US20050209245A1

  公开（公告）日：2005-09-22

  Processes for preparing N-aryl-piperazine derivatives of formula I particularly (R)-4-cyano-N-[2-[4-(2,3-dihydro-1,4-benzodioxan-5-yl)-1-piperazinyl-propyl]-N-(2-pyridinyl)-benzamide, are disclosed. Compositions comprising N-aryl-piperazine derivatives and low levels of common impurities are also disclosed. In addition, products produced by the process are disclosed.

  本发明揭示了制备公式I中的N-芳基哌嗪衍生物的方法，特别是(R)-4-氰基-N-[2-[4-(2,3-二氢-1,4-苯并二氧杂环[5.4]己-5-基)-1-哌嗪基丙基]-N-(2-吡啶基)苯甲酰胺。此外，还揭示了含有N-芳基哌嗪衍生物和低水平常见杂质的组合物。此外，还揭示了通过该方法生产的产品。
• Serotonergic agents
  申请人：American Home Products Corporation

  公开号：US20020107254A1

  公开（公告）日：2002-08-08

  Novel piperazine derivatives are provided having the formula 1 wherein R 1 is cyano, nitro, trifluoromethyl or halogen, or pharmaceutically acceptable acid addition salts thereof, which are useful as 5-HT 1A receptor antagonists.

  提供了具有以下公式1的新型哌嗪衍生物，其中R1是氰基，硝基，三氟甲基或卤素，或其药学上可接受的酸加合物盐，它们可用作5-HT1A受体拮抗剂。
• Process for synthesizing N-aryl piperazines with chiral N′-1-[benzoyl(2-pyridyl)amino]-2-propane substitution
  申请人：Wyeth

  公开号：US06713626B2

  公开（公告）日：2004-03-30

  A process for formation of N-aryl piperazines with chiral N′-1-[benzoyl(2-pyridyl)amino]-2-propane side-chains having the structure shown in formula below, and for making intermediate compounds therefor. In this process, chirality is introduced at the piperazine ring formation step and 2-aminopyridyl substitution is incorporated via displacement. The resulting N,N′ disubstituted piperazines act on the central nervous system at 5HT receptors.

  一种制备具有手性N′-1-[苯甲酰(2-吡啶基)氨基]-2-丙烷侧链的N-芳基哌嗪的方法，其结构如下式所示，并制备其中间体化合物。在该过程中，通过哌嗪环形成步骤引入手性，并通过取代引入2-氨基吡啶基。所得的N,N′-二取代哌嗪在5HT受体上对中枢神经系统产生作用。
• J. Med. Chem. 2005, 48, 3467-3470
  作者：

  DOI：——

  日期：——
• PIPERAZINE DERIVATIVES, THEIR PREPARATION AND THEIR USE FOR TREATING CENTRAL NERVOUS SYSTEM (CNS) DISORDERS
  申请人：Wyeth

  公开号：EP1339406A2

  公开（公告）日：2003-09-03