2-chloro-5-trifluoromethylsulfonyl-1H-benzimidazole | 438190-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-chloro-5-trifluoromethylsulfonyl-1H-benzimidazole
• 英文别名: 1H-Benzimidazole, 2-chloro-6-[(trifluoromethyl)sulfonyl]-；2-chloro-6-(trifluoromethylsulfonyl)-1H-benzimidazole
• CAS: 438190-80-8
• 化学式: C₈H₄ClF₃N₂O₂S
• 分子量: 284.646
• InChiKey: XPEOYEUBJPBQQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-5-trifluoromethylsulfonyl-1H-benzimidazole 、 螺[异苯并呋喃-1(3H),4’-哌啶]-3-酮 在 乙酸乙酯 、 碳酸氢钠 、 水 、 hexanes EtOAc 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以to obtain 1′-(5-trifluoromethylsulfonyl-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one的产率得到1'-(5-trifluoromethylsulfonyl-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4'-piperidin]-3-one
  参考文献：
  名称：

  Spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines

  摘要：

  提供了能够调节NPY5受体活性的代替的spiro [异苯并呋喃-1,4'-哌啶] -3-酮和3H-spiroisobenzofuran-1,4'-哌啶。这些化合物可以用于体内或体外调节配体结合到NPY5受体，并在人类、家养伴侣动物和家畜动物的多种疾病治疗中特别有用（例如，饮食失调，如肥胖或贪食症，精神障碍、糖尿病和心血管疾病，如高血压）。提供了用于治疗这些疾病的药物组合物和方法，以及用于检测NPY5受体的这些化合物的方法。

  公开号：

  US06943199B2
• 作为产物：
  描述：

  2-氨基-4-[(三氟甲基)磺酰基]苯胺 在 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 2-chloro-5-trifluoromethylsulfonyl-1H-benzimidazole
  参考文献：
  名称：

  Identification of a novel and orally available benzimidazole derivative as an NPY Y5 receptor antagonist with in vivo efficacy

  摘要：

  Optimization of lead compound 2 is described, mainly focusing on modification at the C-2 position of the benzimidazole core. Replacement of the phenyl linker of 2 with saturated rings resulted in identification of compound 8b which combines high Y5 receptor binding affinity with a good ADME profile leading to in vivo efficacy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.025

文献信息

• Spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3h-spiroisobenzofuran-1,4'-piperidines
  申请人：Bakthavatchalam Rajagopal

  公开号：US20050033048A1

  公开（公告）日：2005-02-10

  Substituted spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines capable of modulating NPY5 receptor activity are provided. Such compounds may be used to modulate ligand binding to NPY5 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders (e.g., eating disorders such as obesity or bulimia, psychiatric disorders, diabetes and cardiovascular disorders such as hypertension) in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and method for treating such disorders are provided, as are methods for using such compounds for detecting NPY5 receptors.

  本文提供了能够调节NPY5受体活性的取代的spiro[异苯并呋喃-1,4'-哌啶]-3-酮和3H-spiro异苯并呋喃-1,4'-哌啶。这些化合物可以用于体内或体外调节NPY5受体的配体结合，并且在人类、宠物和家畜动物的多种疾病治疗中特别有用（例如，饮食失调如肥胖症或贪食症、精神障碍、糖尿病和心血管疾病如高血压）。提供了制药组合物和治疗这些疾病的方法，以及使用这些化合物检测NPY5受体的方法。
• Spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines
  申请人：Pfizer Inc.

  公开号：US06566367B2

  公开（公告）日：2003-05-20

  Substituted spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines capable of modulating NPY5 receptor activity are provided. Such compounds may be used to modulate ligand binding to NPY5 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders (e.g., eating disorders such as obesity or bulimia, psychiatric disorders, diabetes and cardiovascular disorders such as hypertension) in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such compounds for detecting NPY5 receptors.

  本发明提供了能够调节NPY5受体活性的取代的螺[异苯并呋喃-1,4'-哌啶]-3-酮和3H-螺异苯并呋喃-1,4'-哌啶类化合物。这些化合物可用于体内或体外调节配体与NPY5受体的结合，并在治疗多种疾病（例如，饮食失调，如肥胖症或贪食症，精神障碍，糖尿病和心血管疾病，如高血压）的人类、家养伴侣动物和家畜动物中特别有用。还提供了用于治疗这些疾病的制药组合物和方法，以及用于检测NPY5受体的方法。
• Spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines
  申请人：De Lombaert Stéphane

  公开号：US06943199B2

  公开（公告）日：2005-09-13

  Substituted spiro[isobenzofuran-1,4′-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4′-piperidines capable of modulating NPY5 receptor activity are provided. Such compounds may be used to modulate ligand binding to NPY5 receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of disorders (e.g., eating disorders such as obesity or bulimia, psychiatric disorders, diabetes and cardiovascular disorders such as hypertension) in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such compounds for detecting NPY5 receptors.

  提供了能够调节NPY5受体活性的代替的spiro [异苯并呋喃-1,4'-哌啶] -3-酮和3H-spiroisobenzofuran-1,4'-哌啶。这些化合物可以用于体内或体外调节配体结合到NPY5受体，并在人类、家养伴侣动物和家畜动物的多种疾病治疗中特别有用（例如，饮食失调，如肥胖或贪食症，精神障碍、糖尿病和心血管疾病，如高血压）。提供了用于治疗这些疾病的药物组合物和方法，以及用于检测NPY5受体的这些化合物的方法。
• Spiro [isobenzofuran-1,4'piperidin]-3-ones and 3H-spiroisobenzofuran-1, 4'-piperidines
  申请人：NEUROGEN CORPORATION

  公开号：EP1695977A2

  公开（公告）日：2006-08-30

  This invention relates generally to substituted spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3H-spiroisobenzofuran-1,4'-piperidines that are modulators of mammalian neuropeptide Y5 (NPY5) receptors, and to the use of such compounds for treating a variety of physiological disorders associated with NPY5 receptor activation, such as feeding disorders, psychiatric disorders and cardiovascular diseases. The invention further relates to the use such compounds as probes for the detection and localization of NPY5 receptors.

  本发明一般涉及取代的螺[异苯并呋喃-1,4'-哌啶]-3-酮和3H-螺异苯并呋喃-1,4'-哌啶，它们是哺乳动物神经肽Y5（NPY5）受体的调节剂，本发明还涉及使用此类化合物治疗与NPY5受体激活有关的各种生理紊乱，如进食紊乱、精神紊乱和心血管疾病。本发明进一步涉及将此类化合物用作检测和定位 NPY5 受体的探针。
• SPIRO ISOBENZOFURAN-1,4'-PIPERIDIN]-3-ONES AND 3H-SPIROISOBENZOFURAN-1,4'-PIPERIDINES
  申请人：Neurogen Corporation

  公开号：EP1347982A2

  公开（公告）日：2003-10-01