(S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one | 250237-01-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one
• 英文别名: (2S)-2-amino-4-methyl-1-[4-[N-(3-methylbut-2-enyl)-4-phenylmethoxyanilino]piperidin-1-yl]pentan-1-one
• CAS: 250237-01-5
• 化学式: C₂₉H₄₁N₃O₂
• 分子量: 463.663
• InChiKey: SQIXRXHMHVGSSD-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one 在 NaBH(OAc)3 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 以176 mg (81%)的产率得到(S)-1-{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-2-isopropylamino-4-methyl-pentan-1-one
  参考文献：
  名称：

  Aniline derivatives as calcium channel blockers

  摘要：

  本发明提供了一种阻断钙通道的化合物，其化学式为(I)。本发明还提供了使用化合物(I)治疗中风、脑缺血、头部创伤或癫痫的方法，以及含有化合物(I)的药物组合物。

  公开号：

  US06251918B1
• 作为产物：
  描述：

  (S)-(1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidine-1-carbonyl}-3-methyl-butyl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以0.87 g (99%)的产率得到(S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one
  参考文献：
  名称：

  Aniline derivatives as calcium channel blockers

  摘要：

  本发明提供了一种阻断钙通道的化合物，其化学式为(I)。本发明还提供了使用化合物(I)治疗中风、脑缺血、头部创伤或癫痫的方法，以及含有化合物(I)的药物组合物。

  公开号：

  US06251918B1

文献信息

• [EN] ANILINE DERIVATIVES AS CALCIUM CHANNEL BLOCKERS<br/>[FR] DERIVES D'ANILINE UTILISES EN TANT QU'INHIBITEURS CALCIQUES
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1999007689A1

  公开（公告）日：1999-02-18

  (EN) The present invention provides compounds that block calcium channels having formula (I). The present invention also privides methods of using the compounds of formula (I) to treat stroke, cerebral ischemia, head trauma, or epilepsy and to pharmaceutical compositions that contain the compounds of formula (I).(FR) L'invention concerne des composés inhibiteurs calciques, de formule (I). Elle se rapporte également à des procédés d'utilisation desdits composés de formule (I) pour le traitement de l'attaque, de l'ischémie cérébrale, du traumatisme crânien ou de l'épilepsie, et à des compositions pharmaceutiques contenant les composés de formule (I).

  本发明提供了具有式（I）的阻断钙通道的化合物。本发明还提供了使用式（I）的化合物治疗中风、脑缺血、头部创伤或癫痫的方法，以及含有式（I）的药物组合物。
• Calcium channel blockers
  申请人：——

  公开号：US20010023249A1

  公开（公告）日：2001-09-20

  The present invention provides compounds that block calcium channels having the Formula I shown below. 1 The present invention also provides methods of using the compounds of Formula I to treat stroke, cerebral ischemia, head trauma, or epilepsy and to pharmaceutical compositions that contain the compounds of Formula I.

  本发明提供了具有下面式子I的阻断钙通道的化合物。同时，本发明还提供了使用式子I的化合物治疗中风、脑缺血、头部创伤或癫痫的方法，以及含有式子I的制药组合物。
• Pharmaceutical composition containing gabapentin or pregabalin and N-type calcium channel antagonist
  申请人：Iwayama Satoshi

  公开号：US20050009814A1

  公开（公告）日：2005-01-13

  The present invention relates to a pharmaceutical composition useful for preventing/treating pain, which comprises combination of gabapentin or pregabalin, or pharmaceutically acceptable salts thereof and N-type calcium channel antagonists or pharmaceutically acceptable salts thereof such as a compound having the following structure.

  本发明涉及一种用于预防/治疗疼痛的药物组合物，包括加巴喷丁或普瑞巴林或其药学上可接受的盐和N型钙通道拮抗剂或其药学上可接受的盐，例如具有以下结构的化合物。
• MEDICINAL COMPOSITIONS CONTAINING GABAPENTIN OR PREGABALIN AND N-TYPE CALCIUM CHANNEL ANTAGONIST
  申请人：Ajinomoto Co., Inc.

  公开号：EP1481673A1

  公开（公告）日：2004-12-01

  The present invention relates to a pharmaceutical composition useful for preventing/treating pain, which comprises combination of gabapentin or pregabalin, or pharmaceutically acceptable salts thereof and N-type calcium channel antagonists or pharmaceutically acceptable salts thereof such as a compound having the following structure.

  本发明涉及一种用于预防/治疗疼痛的药物组合物，它包括加巴喷丁或普瑞巴林或其药学上可接受的盐类与 N 型钙通道拮抗剂或其药学上可接受的盐类的组合，例如具有以下结构的化合物。
• Synthesis of a Series of 4-Benzyloxyaniline Analogues as Neuronal N-Type Calcium Channel Blockers with Improved Anticonvulsant and Analgesic Properties
  作者：Lain-Yen Hu、Todd R. Ryder、Michael F. Rafferty、M. Rose Feng、Susan M. Lotarski、David M. Rock、Michael Sinz、Sally J. Stoehr、Charles P. Taylor、Mark L. Weber、S. Scott Bowersox、George P. Miljanich、Elizabeth Millerman、Yong-Xiang Wang、Balazs G. Szoke

  DOI：10.1021/jm9902739

  日期：1999.10.1

  In this article, the rationale for the design, synthesis, and biological evaluation of a series of N-type voltage-sensitive calcium channel (VSCC) blockers is described. N-Type VSCC blockers, such as ziconotide, have shown utility in several models of stroke and pain. Modification of the previously reported lead, 1a, led to several 4-(4-benzyloxylphenyl)piperidine structures with potent in vitro and in vivo activities. In this series, the most interesting compound, (S)-2-amino- 1-4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one (11), blocked N-type calcium channels (IC50 = 0.67 mu M in the IMR32 assay) and was efficacious in the audiogenic DBA/2 seizure mouse model (ED50 = 6 mg/kg, iv) as well as the antiwrithing model (ED50 = 6 mg/kg, iv). Whole-cell voltage-clamp electrophysiology experiments demonstrated that compound 11 blocked N-type Ca2+ channels and Na+ channels in superior cervical ganglion neurons at similar concentrations. Compound 11, which showed superior in vivo efficacy, stands out as an interesting lead for further development of neurotherapeutic agents in this series.