1-Ethoxycarbonyl-4-[(2-methyl-6-nitrophenyl)amino]piperidine | 356072-51-0

• 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: 1-Ethoxycarbonyl-4-[(2-methyl-6-nitrophenyl)amino]piperidine
• 英文别名: ethyl 4-(2-methyl-6-nitroanilino)piperidine-1-carboxylate
• CAS: 356072-51-0
• 化学式: C₁₅H₂₁N₃O₄
• 分子量: 307.349
• InChiKey: BHSRWWOKMYWTDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Ethoxycarbonyl-4-[(2-methyl-6-nitrophenyl)amino]piperidine 在 platinum on activated charcoal 甲酸铵 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-Ethoxycarbonyl-4-(1,3-dihydro-7-methyl-2H-benzimidazol-2-on-1-yl)piperidine
  参考文献：
  名称：

  Discovery and SAR studies of a novel series of noncovalent cathepsin S inhibitors

  摘要：

  A novel series of competitive, reversible cathepsin S (Cats) inhibitors was discovered and optimized. The 4-(2-keto-1-benzimidazolinyl)-piperidin-1-yl moiety was found to be an effective replacement for the 4-arylpiperazin-1-yl group found in our earlier series of Cats inhibitors. This replacement imparted improved PK properties as well as decreased off-target activity. Optimization of the ketobenzimidazole moiety led to the discovery of the lead compound JNJ 10329670, which represents a novel class of selective, noncovalent, reversible, and orally bioavailable inhibitors of cathepsin S. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.045
• 作为产物：
  描述：

  1-Benzyl-4-[(2-methyl-6-nitrophenyl)amino]piperidine 、 氯甲酸乙酯 在 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以90%的产率得到1-Ethoxycarbonyl-4-[(2-methyl-6-nitrophenyl)amino]piperidine
  参考文献：
  名称：

  Phenoxyalkylamine derivatives useful as opioid receptor agonists

  摘要：

  一种用于预防和/或治疗神经系统疾病的药物，其活性成分为以下通用式（I）或其药理学可接受的盐所代表的化合物： 其中，X代表以下通用式（II）、（III）、（IV）、（V）或（VI）所代表的基团，“A”代表饱和或不饱和的3-至6-成员碳环基团等，“B”代表CH2等，“n”代表0至2，R1代表氢原子、卤素原子等，R2、R3和R7至R14代表氢原子、可能被取代的较低烷基基团等，R4代表氢原子、可能被取代的较低烷基基团等，R5代表氢原子、卤素原子等，R6代表饱和或不饱和的单环或双环碳环基团等，且R5和R6、R7和R8、R9和R10，或R11和R12可以结合在一起形成环状结构。

  公开号：

  US20030171370A1

文献信息

• Phenoxyalkylamine derivatives useful as opioid delta receptor ligands
  申请人：Tsushima Masaki

  公开号：US20050148583A1

  公开（公告）日：2005-07-07

  A medicament useful for preventive and/or therapeutic treatment of nerve system diseases which comprises, as an active ingredient, a compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof: wherein, X represents a group represented by the following general formula (II), (III), (IV), (V), or (VI), “A” represents a saturated or unsaturated 3- to 6-membered carbocyclic group and the like, “B” represents CH 2 and the like, “n” represents 0 to 2, R 1 represents a hydrogen atom, a halogen atom and the like, R 2 , R 3 , and R 7 to R 14 represent a hydrogen atom, a lower alkyl group which may be substituted and the like, R 4 represents a hydrogen atom, a lower alkyl group which may be substituted and the like, R 5 represents a hydrogen atom, a halogen atom and the like, R 6 represents a saturated or unsaturated monocyclic or bicyclic carbocyclic group and the like, and R 5 and R 6 , R 7 and R 8 , R 9 and R 10 , or R 11 and R 12 may bind to each other to form a cyclic structure.

  一种用于神经系统疾病的预防和/或治疗的药物，其包括以下通式（I）所表示的化合物或其药学上可接受的盐作为活性成分： 其中，X代表以下通式（II），（III），（IV），（V）或（VI）所表示的基团，“A”代表饱和或不饱和的3-至6-成员的碳环基团等，“B”代表CH2等，“n”代表0至2，“R1”代表氢原子，卤原子等，“R2”，“R3”和“R7”至“R14”代表氢原子，可被取代的较低烷基基团等，“R4”代表氢原子，可被取代的较低烷基基团等，“R5”代表氢原子，卤原子等，“R6”代表饱和或不饱和的单环或双环碳环基团等，“R5”和“R6”，“R7”和“R8”，“R9”和“R10”，或“R11”和“R12”可以结合在一起形成环状结构。
• Phenoxyalkylamine derivatives useful as opioid δ receptor agonists
  申请人：Tsushima Masaki

  公开号：US06916822B2

  公开（公告）日：2005-07-12

  A medicament useful for preventive and/or therapeutic treatment of nerve system diseases which comprises, as an active ingredient, a compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof: wherein, X represents a group represented by the following general formula (II), (III), (IV), (V), or (VI), “A” represents a saturated or unsaturated 3- to 6-membered carbocyclic group and the like, “B” represents CH 2 and the like, “n” represents 0 to 2, R 1 represents a hydrogen atom, a halogen atom and the like, R 2 , R 3 , and R 7 to R 14 represent a hydrogen atom, a lower alkyl group which may be substituted and the like, R 4 represents a hydrogen atom, a lower alkyl group which may be substituted and the like, R 5 represents a hydrogen atom, a halogen atom and the like, R 6 represents a saturated or unsaturated monocyclic or bicyclic carbocyclic group and the like, and R 5 and R 6 , R 7 and R 8 , R 9 and R 10 , or R 11 and R 12 may bind to each other to form a cyclic structure.

  一种用于预防和/或治疗神经系统疾病的药物，其包含以下通式（I）或其药学上可接受的盐作为活性成分的化合物： 其中，X表示以下通式（II）、（III）、（IV）、（V）或（VI）表示的基团，“A”表示饱和或不饱和的3-至6-成员的碳环基团等，“B”表示CH2等，“n”表示0至2，R1表示氢原子、卤原子等，R2、R3和R7至R14表示氢原子、可被取代的较低烷基基团等，R4表示氢原子、可被取代的较低烷基基团等，R5表示氢原子、卤原子等，R6表示饱和或不饱和的单环或双环碳环基团等，并且R5和R6、R7和R8、R9和R10或R11和R12可以结合在一起形成环状结构。
• Discovery and SAR studies of a novel series of noncovalent cathepsin S inhibitors
  作者：Darin J. Gustin、Clark A. Sehon、Jianmei Wei、Hui Cai、Steven P. Meduna、Haripada Khatuya、Siquan Sun、Yin Gu、Wen Jiang、Robin L. Thurmond、Lars Karlsson、James P. Edwards

  DOI：10.1016/j.bmcl.2005.01.045

  日期：2005.3

  A novel series of competitive, reversible cathepsin S (Cats) inhibitors was discovered and optimized. The 4-(2-keto-1-benzimidazolinyl)-piperidin-1-yl moiety was found to be an effective replacement for the 4-arylpiperazin-1-yl group found in our earlier series of Cats inhibitors. This replacement imparted improved PK properties as well as decreased off-target activity. Optimization of the ketobenzimidazole moiety led to the discovery of the lead compound JNJ 10329670, which represents a novel class of selective, noncovalent, reversible, and orally bioavailable inhibitors of cathepsin S. (c) 2005 Elsevier Ltd. All rights reserved.
• PHENOXYALKYLAMINE DERIVATIVES USEFUL AS OPIOID DELTA RECEPTOR AGONISTS
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1256575B1

  公开（公告）日：2005-08-17
• US6916822B2
  申请人：——

  公开号：US6916822B2

  公开（公告）日：2005-07-12