N-[1-(1-methylcyclooctyl)-4-piperidinyl]-1,2-benzenediamine | 1108147-58-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[1-(1-methylcyclooctyl)-4-piperidinyl]-1,2-benzenediamine
• 英文别名: N1-[1-(1-methylcyclooctyl)-4-piperidinyl]-1,2-benzenediamine；2-N-[1-(1-methylcyclooctyl)piperidin-4-yl]benzene-1,2-diamine
• CAS: 1108147-58-5
• 化学式: C₂₀H₃₃N₃
• 分子量: 315.502
• InChiKey: HVXGRALUUCWZRB-UHFFFAOYSA-N

物化性质

• 沸点：
  463.3±40.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  41.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[1-(1-methylcyclooctyl)-4-piperidinyl]-1,2-benzenediamine 、 3-(三氟甲基)苯甲酰氯 在 吡啶 、 phosphoryl trichloride 作用下， 反应 4.5h， 以21%的产率得到1-[1-(1-methylcyclooctyl)piperidin-4-yl]-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazole
  参考文献：
  名称：

  Novel Non-Peptide Nociceptin/Orphanin FQ Receptor Agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: Design, Synthesis, and Structure−Activity Relationship of Oral Receptor Occupancy in the Brain for Orally Potent Antianxiety Drug

  摘要：

  An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus, the N/OFQ and NOP receptor are located in the central nervous systems in humans, primates, and rodents, and are involved in the integration of the emotional components in the brain; e.g., N/OFQ displays anxiolytic activity in the brain. For identifying orally potent anxiolytic, drug-design studies were performed with a series of 1,2-disubstituted benzimidazole derivatives, which resulted in the identification of various chemotypes of highly potent NOP selective full agonists in vitro with high or moderate NOP receptor occupancy in the mice brain per os such as 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1-H-benzimidazole 1 (MCOPPB), the most potent novel non-peptide NOP full agonist in vitro and an orally potent anxiolytic in the mice.

  DOI：

  10.1021/jm7012979
• 作为产物：
  描述：

  1-(1-methylcyclooctyl)-N-(2-nitrophenyl)piperidin-4-amine 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.25h， 以100%的产率得到N-[1-(1-methylcyclooctyl)-4-piperidinyl]-1,2-benzenediamine
  参考文献：
  名称：

  Novel Non-Peptide Nociceptin/Orphanin FQ Receptor Agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: Design, Synthesis, and Structure−Activity Relationship of Oral Receptor Occupancy in the Brain for Orally Potent Antianxiety Drug

  摘要：

  An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus, the N/OFQ and NOP receptor are located in the central nervous systems in humans, primates, and rodents, and are involved in the integration of the emotional components in the brain; e.g., N/OFQ displays anxiolytic activity in the brain. For identifying orally potent anxiolytic, drug-design studies were performed with a series of 1,2-disubstituted benzimidazole derivatives, which resulted in the identification of various chemotypes of highly potent NOP selective full agonists in vitro with high or moderate NOP receptor occupancy in the mice brain per os such as 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1-H-benzimidazole 1 (MCOPPB), the most potent novel non-peptide NOP full agonist in vitro and an orally potent anxiolytic in the mice.

  DOI：

  10.1021/jm7012979

文献信息

• Substituted-Quinoxaline-Type Piperidine Compounds and the Uses Thereof
  申请人：FUCHINO Kouki

  公开号：US20100216726A1

  公开（公告）日：2010-08-26

  The invention relates to Substituted-Quinoxaline-Type Piperidine Compounds, compositions comprising an effective amount of a Substituted-Quinoxaline-Type Piperidine Compound and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Substituted-Quinoxaline-Type Piperidine Compound.

  本发明涉及取代喹喔啉型哌啶化合物、包含有效量取代喹喔啉型哌啶化合物的组合物以及治疗或预防某种疾病（如疼痛）的方法，包括向需要治疗的动物施用有效量取代喹喔啉型哌啶化合物。
• SUBSTITUTED-QUINOXALINE-TYPE PIPERIDINE COMPOUNDS AND THE USES THEREOF
  申请人：Purdue Pharma L.P.

  公开号：US20150141643A1

  公开（公告）日：2015-05-21

  The invention relates to Substituted-Quinoxaline-Type Piperidine Compounds, compositions comprising an effective amount of a Substituted-Quinoxaline-Type Piperidine Compound and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Substituted-Quinoxaline-Type Piperidine Compound.

  该发明涉及取代喹喔啉型哌啶化合物，包括一种有效量的取代喹喔啉型哌啶化合物的组合物以及治疗或预防疾病的方法，例如疼痛，通过向需要治疗的动物施用一种有效量的取代喹喔啉型哌啶化合物。
• Substituted-quinoxaline-type-piperidine compounds and the uses thereof
  申请人：Purdue Pharma LP

  公开号：EP2433935A1

  公开（公告）日：2012-03-28

  The invention relates to Substituted-Quinoxaline-Type Piperidine Compounds of Formula (I) and Formula (II), compositions comprising an effective amount of a Substituted-Quinoxaline-Type Piperidine Compound and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Substituted-Quinoxaline-Type Piperidine Compound.

  本发明涉及式（I）和式（II）的取代喹喔啉型哌啶化合物、包含有效量的取代喹喔啉型哌啶化合物的组合物，以及治疗或预防疼痛等疾病的方法，包括向有需要的动物施用有效量的取代喹喔啉型哌啶化合物。
• PIPERIDINE INTERMEDIATES
  申请人：Purdue Pharma L.P.

  公开号：EP3564240A1

  公开（公告）日：2019-11-06

  The invention relates to intermediates A3 and A4 for making Substituted-Quinoxaline-Type Piperidine Compounds.

  本发明涉及用于制造取代喹喔啉型哌啶化合物的中间体 A3 和 A4。
• SUBSTITUTED-QUINOXALINE-TYPE-PIPERIDINE COMPOUNDS AND THE USES THEREOF
  申请人：Purdue Pharma LP

  公开号：EP2086958B1

  公开（公告）日：2015-01-14