1-[1-(1-甲基环辛基)-4-哌啶基]-2-[(3R)-3-哌啶基]-1H-苯并咪唑 | 1028969-49-4

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-[1-(1-甲基环辛基)-4-哌啶基]-2-[(3R)-3-哌啶基]-1H-苯并咪唑
• 中文别名: 1-(1-(1-甲基环辛基)哌啶-4-基)-2-(哌啶-3-基)-1H-苯并[d]咪唑三盐酸盐
• 英文名称: 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole
• 英文别名: MCOPPB；1-[1-(1-methylcyclooctyl)piperidin-4-yl]-2-[(3R)-piperidin-3-yl]benzimidazole
• CAS: 1028969-49-4
• 化学式: C₂₆H₄₀N₄
• 分子量: 408.63
• InChiKey: CYYNMPPFEJPBJD-OAQYLSRUSA-N

物化性质

• 熔点：
  >249°C (dec.)
• 沸点：
  576.5±50.0 °C(Predicted)
• 密度：
  1.18
• 溶解度：
  在水中的溶解度≥13mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1-[1-(1-甲基环辛基)-4-哌啶基]-2-[(3R)-3-哌啶基]-1H-苯并咪唑 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以769.3 mg的产率得到MCOPPB
  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：

  tert-butyl (3R)-3-{1-[1-(1-methylcyclooctyl)-4-piperidinyl]-1H-benzimidazol-2-yl}-1-piperidinecarboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以92%的产率得到1-[1-(1-甲基环辛基)-4-哌啶基]-2-[(3R)-3-哌啶基]-1H-苯并咪唑
  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 BENZIMIDAZOLE-TYPE PIPERIDINE COMPOUNDS AND USES THEREOF
  申请人：Shionogi & Co., Ltd.

  公开号：US20140187535A1

  公开（公告）日：2014-07-03

  The disclosure relates to Substituted Benzimidazole-Type Piperidine Compounds of Formula (I): and pharmaceutically acceptable salts or solvates thereof, e.g., a pharmaceutically acceptable salt or solvate, wherein R 1 , R 2 , R 3 , Q a , W, U, A, B, Z, a, and the dashed lines are as defined herein, compositions comprising an effective amount of a Substituted Benzimidazole-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 Benzimidazole-Type Piperidine Compound.

  该披露涉及式(I)的取代苯并咪唑基哌啶化合物及其药学上可接受的盐或溶剂，例如药学上可接受的盐或溶剂，其中R1、R2、R3、Qa、W、U、A、B、Z、a和虚线如本文所定义，包括有效量的取代苯并咪唑基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，包括向需要的动物施用有效量的取代苯并咪唑基哌啶化合物。
• MCOPPB FOR USE AS MEDICAMENT
  申请人：Univerzita Palackého V Olomouchi

  公开号：EP3552605A1

  公开（公告）日：2019-10-16

  The present invention provides 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole of formula for use in a method of treatment of a condition involving accumulation of senescent cells. The conditions involving accumulation of senescent cells are in particular cancer, cardiovascular, neurology and immune related diseases.

  本发明提供了 1-[1-(1-甲基环辛基)-4-哌啶基]-2-[(3R)-3-哌啶基]-1H-苯并咪唑，其式为 用于涉及衰老细胞积累的病症的治疗方法。涉及衰老细胞积聚的疾病尤其包括癌症、心血管疾病、神经疾病和免疫相关疾病。
• Compositions and methods for intrathecal administration of MCOPPB for pain relief
  申请人：Centrexion Therapeutics Corporation

  公开号：US11045459B1

  公开（公告）日：2021-06-29

  The invention provides compositions and methods for intrathecal administration of the compound MCOPPB or a pharmaceutically acceptable salt thereof for treating pain, such as neuropathic pain suffered by an adult human.

  本发明提供了鞘内给药化合物 MCOPPB 或其药学上可接受的盐的组合物和方法，用于治疗疼痛，如成人的神经性疼痛。
• PHARMACEUTICAL COMPOSITIONS
  申请人：Charleston Laboratories, Inc.

  公开号：EP3129028A1

  公开（公告）日：2017-02-15
• PAIN MANAGEMENT IN SICKLE CELL ANEMIA
  申请人：Regents of the University of Minnesota

  公开号：US20140171466A1

  公开（公告）日：2014-06-19

  The present invention relates to a method for the management of pain associated with sickle cell disease. In particular, the method comprises administering to a patient in need of such pain management a therapeutically effective amount of a nociceptin (NOP) receptor agonist or an NOP receptor agonist/mu opioid receptor (MOR) partial agonist.