4-[3-[4-(3-Fluoroanilino)piperidin-1-yl]-3-oxopropyl]benzaldehyde | 1127440-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[3-[4-(3-Fluoroanilino)piperidin-1-yl]-3-oxopropyl]benzaldehyde
• CAS: 1127440-68-9
• 化学式: C₂₁H₂₃FN₂O₂
• 分子量: 354.424
• InChiKey: HFXPWYAMTBEZCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[3-[4-(3-Fluoroanilino)piperidin-1-yl]-3-oxopropyl]benzaldehyde 、 (S)-1-N-Cbz-2-甲基哌嗪 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 benzyl (2S)-4-[[4-[3-[4-(3-fluoroanilino)piperidin-1-yl]-3-oxopropyl]phenyl]methyl]-2-methylpiperazine-1-carboxylate
  参考文献：
  名称：

  Discovery of N-(3-Fluorophenyl)-1-[(4-([(3S)-3-methyl-1-piperazinyl]methyl)phenyl)acetyl]-4-piperidinamine (GSK962040), the First Small Molecule Motilin Receptor Agonist Clinical Candidate

  摘要：

  N-(3-Fluorophenyl)-1-[(4-([(3S)-3-methyl-1-piperazinyl]methyl)phenyl)acetyl]-4-piperidinamine 12 (GSK962040) is a novel small molecule motilin receptor agonist. It possesses excellent activity at the recombinant human motilin receptor and also at the native rabbit motilin receptor where its agonist activity results in potentiation of the amplitude of neuronal-mediated contractions of isolated gastric antrum, tissue. Compound 12 also possesses highly promising pharmacokinetic profiles in both rat and dog, and these results, in combination with further profiling in human native tissue and an in vivo model of gastrointestinal transit in the rabbit, have led to its selection as a candidate for further development.

  DOI：

  10.1021/jm801332q
• 作为产物：
  描述：

  N-(3-氟苯基)哌啶-4-胺 、 3-(4-甲酰基苯基)丙-2-烯酸 在 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 manganese(IV) oxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 4-[3-[4-(3-Fluoroanilino)piperidin-1-yl]-3-oxopropyl]benzaldehyde
  参考文献：
  名称：

  Discovery of N-(3-Fluorophenyl)-1-[(4-([(3S)-3-methyl-1-piperazinyl]methyl)phenyl)acetyl]-4-piperidinamine (GSK962040), the First Small Molecule Motilin Receptor Agonist Clinical Candidate

  摘要：

  N-(3-Fluorophenyl)-1-[(4-([(3S)-3-methyl-1-piperazinyl]methyl)phenyl)acetyl]-4-piperidinamine 12 (GSK962040) is a novel small molecule motilin receptor agonist. It possesses excellent activity at the recombinant human motilin receptor and also at the native rabbit motilin receptor where its agonist activity results in potentiation of the amplitude of neuronal-mediated contractions of isolated gastric antrum, tissue. Compound 12 also possesses highly promising pharmacokinetic profiles in both rat and dog, and these results, in combination with further profiling in human native tissue and an in vivo model of gastrointestinal transit in the rabbit, have led to its selection as a candidate for further development.

  DOI：

  10.1021/jm801332q

文献信息

• BENZYLPIPERAZINE DERIVATIVES AND THEIR MEDICAL USE
  申请人：Johnson Christopher Norbert

  公开号：US20090054456A1

  公开（公告）日：2009-02-26

  The present invention relates to novel benzylpiperazine derivatives such as compounds of formula (I), which have activity as agonists of the GPR38 receptor and the use of such compounds or pharmaceutical compositions thereof in the treatment of gastrointestinal disorders.

  本发明涉及新型苄基哌嗪衍生物，如公式(I)化合物，其具有作为GPR38受体激动剂的活性，以及在治疗胃肠道疾病中使用这些化合物或其制剂的药物组合物。
• COMPOUNDS
  申请人：Glaxo Group Limited

  公开号：US20130317041A1

  公开（公告）日：2013-11-28

  The present invention relates to benzylpiperazine derivatives such as compounds of formula (I), which have activity as agonists of the GPR38 receptor and the use of such compounds or pharmaceutical compositions thereof in the preparation of medicaments suitable for the treatment of gastrointestinal disorders.

  本发明涉及苄基哌嗪衍生物，例如公式（I）的化合物，它们具有作为GPR38受体激动剂的活性，以及使用这些化合物或其制剂在制备适用于治疗胃肠道疾病的药物中的用途。
• Benzylpiperazine derivatives useful for the treatment of gastrointestinal disorders
  申请人：GLAXO GROUP LIMITED

  公开号：EP1907374B1

  公开（公告）日：2012-08-22
• US8536182B2
  申请人：——

  公开号：US8536182B2

  公开（公告）日：2013-09-17
• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：GLAXO GROUP LTD

  公开号：WO2007012479A2

  公开（公告）日：2007-02-01

  [EN] The present invention relates to novel benzylpiperazine derivatives such as compounds of formula (I), which have activity as agonists of the GPR38 receptor and the use of such compounds or pharmaceutical compositions thereof in the treatment of gastrointestinal disorders.
  [FR] La présente invention concerne de nouveaux dérivés de benzylpipérazine tels que les composés représentés par la formule (I), qui présentent une activité en tant qu'agonistes du récepteur GPR38, ainsi que l'utilisation desdits composés ou de compositions pharmaceutiques associées dans le traitement de troubles gastro-intestinaux.