4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide | 220032-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide
• 英文别名: 4-amino-5-chloro-2-methoxy-N-[1-(piperidin-4-ylmethyl)piperidin-4-yl]benzamide
• CAS: 220032-14-4
• 化学式: C₁₉H₂₉ClN₄O₂
• 分子量: 380.918
• InChiKey: ZFUJFWCMGFVGAD-UHFFFAOYSA-N

物化性质

• 沸点：
  528.270±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.249±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  79.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide 在 一水合肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 15.5h， 生成 4-Amino-N-{1-[1-(3-amino-2-hydroxy-propyl)-piperidin-4-ylmethyl]-piperidin-4-yl}-5-chloro-2-methoxy-benzamide
  参考文献：
  名称：

  Novel N -[1-(1-substituted 4-piperidinylmethyl)-4-piperidinyl]benzamides as potent colonic prokinetic agents

  摘要：

  A series of novel N-[1-(1-substituted 4-piperidinylmethyl)-4-piperidinyl]benzamides was prepared and its compounds were evaluated for their binding to 5-HT4 receptors and effects on gastrointestinal motility in conscious dogs. 4-Amino-N-[1-[l-(4aminobutyl)-4-piperidinylmethyi]-4-piperidinyl]-5-chloro-2-methoxybenzamide (15) was found to have a potent binding affinity for 5-HT4 receptors (IC50: 6.47 nM) and showed excellent colonic prokinetic activity. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00060-4
• 作为产物：
  描述：

  Benzyl 4-[[4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]piperidin-1-yl]methyl]piperidine-1-carboxylate 在 甲烷磺酸 、 苯甲醚 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide
  参考文献：
  名称：

  Novel N -[1-(1-substituted 4-piperidinylmethyl)-4-piperidinyl]benzamides as potent colonic prokinetic agents

  摘要：

  A series of novel N-[1-(1-substituted 4-piperidinylmethyl)-4-piperidinyl]benzamides was prepared and its compounds were evaluated for their binding to 5-HT4 receptors and effects on gastrointestinal motility in conscious dogs. 4-Amino-N-[1-[l-(4aminobutyl)-4-piperidinylmethyi]-4-piperidinyl]-5-chloro-2-methoxybenzamide (15) was found to have a potent binding affinity for 5-HT4 receptors (IC50: 6.47 nM) and showed excellent colonic prokinetic activity. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00060-4

文献信息

• 1-[(1-Substituted-4-piperidinyl)methyl]-4-piperidine derivative, process for producing the same, medicinal compositions containing the same and intermediates of these compounds
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US06294555B1

  公开（公告）日：2001-09-25

  Compound of the formula (I): wherein Ar is a group of the following formula (Ar-1) or (Ar-2): A is a group of the formula: —Z—N(Q1)(Q2), —CO—R7 or —(CH2)p—CH(R8)—COR9, or a pharmaceutically acceptable acid addition salt thereof, a process for preparing the same, a pharmaceutical composition containing the same, and intermediates therefor. The compounds of the present invention show a potent affinity for 5-HT4 receptors, and they are useful as a gastrointestinal motility enhancer or a gastrointestinal prokinetic agent.

  化合物的公式（I）：其中Ar是以下公式（Ar-1）或（Ar-2）的基团：A是以下公式的基团：—Z—N（Q1）（Q2）、—CO—R7或—（CH2）p—CH（R8）—COR9，或其药学上可接受的酸盐，制备该化合物的方法、含有该化合物的药物组合物，以及其中间体。本发明的化合物显示出对5-HT4受体的强大亲和力，它们可用作胃肠蠕动增强剂或胃肠促动剂。
• 1- (1-SUBSTITUTED-4-PIPERIDINYL)METHYL]-4-PIPERIDINE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, MEDICINAL COMPOSITIONS CONTAINING THE SAME AND INTERMEDIATES OF THESE COMPOUNDS
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP1076055B1

  公开（公告）日：2004-11-24
• US6294555B1
  申请人：——

  公开号：US6294555B1

  公开（公告）日：2001-09-25
• Novel N -[1-(1-substituted 4-piperidinylmethyl)-4-piperidinyl]benzamides as potent colonic prokinetic agents
  作者：Hiroshi Harada、Hiroshi Yamazaki、Yoshihito Toyotomi、Hirotaka Tateishi、Yukiko Mine、Naoyuki Yoshida、Shiro Kato

  DOI：10.1016/s0960-894x(02)00060-4

  日期：2002.3

  A series of novel N-[1-(1-substituted 4-piperidinylmethyl)-4-piperidinyl]benzamides was prepared and its compounds were evaluated for their binding to 5-HT4 receptors and effects on gastrointestinal motility in conscious dogs. 4-Amino-N-[1-[l-(4aminobutyl)-4-piperidinylmethyi]-4-piperidinyl]-5-chloro-2-methoxybenzamide (15) was found to have a potent binding affinity for 5-HT4 receptors (IC50: 6.47 nM) and showed excellent colonic prokinetic activity. (C) 2002 Published by Elsevier Science Ltd.