2-(4-trifluoromethylphenyl)-6H-thieno[2,3-d]pyridazin-7-one | 868662-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-trifluoromethylphenyl)-6H-thieno[2,3-d]pyridazin-7-one
• 英文别名: 2-(4-trifluoromethyl-phenyl)-thieno[2,3-d]pyridazin-7(6H)-one；2-[4-(trifluoromethyl)phenyl]-6H-thieno[2,3-d]pyridazin-7-one
• CAS: 868662-16-2
• 化学式: C₁₃H₇F₃N₂OS
• 分子量: 296.273
• InChiKey: OQZWYQBHIREUKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(S)-1-(5-bromopyridin-2-yl)pyrrolidin-3-yl]methylamine 、 2-(4-trifluoromethylphenyl)-6H-thieno[2,3-d]pyridazin-7-one 在 copper(l) iodide 、 (1S,2S)-(+)-1,2-环己二胺 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 (S)-6-(6-(3-(methylamino)pyrrolidin-1-yl)pyridin-3-yl)-2-(4-(trifluoromethyl)phenyl)thieno[2,3-d]pyridazin-7(6H)-one
  参考文献：
  名称：

  A Thienopyridazinone-Based Melanin-Concentrating Hormone Receptor 1 Antagonist with Potent in Vivo Anorectic Properties

  摘要：

  Melanin-concentrating hormone receptor antagonists containing thieno- and a benzopyridazinone cores were designed and tested as potential anorectic agents. These ligands showed high affinity for the receptor, potent functional activity in vitro, and good oral bioavailabilty in rats. The thiophene analogue exhibited low iv clearance, long half-life, and high brain penetration. In obese rats, the thienopyridazinone demonstrated a dose-dependent reduction in feeding and body weight with doses between 1 and 10 mg kg(-1).

  DOI：

  10.1021/jm051263c
• 作为产物：
  描述：

  4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one 在 盐酸 、 sodium sulfide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-(4-trifluoromethylphenyl)-6H-thieno[2,3-d]pyridazin-7-one
  参考文献：
  名称：

  A Thienopyridazinone-Based Melanin-Concentrating Hormone Receptor 1 Antagonist with Potent in Vivo Anorectic Properties

  摘要：

  Melanin-concentrating hormone receptor antagonists containing thieno- and a benzopyridazinone cores were designed and tested as potential anorectic agents. These ligands showed high affinity for the receptor, potent functional activity in vitro, and good oral bioavailabilty in rats. The thiophene analogue exhibited low iv clearance, long half-life, and high brain penetration. In obese rats, the thienopyridazinone demonstrated a dose-dependent reduction in feeding and body weight with doses between 1 and 10 mg kg(-1).

  DOI：

  10.1021/jm051263c

文献信息

• [EN] 2- (3-AMINOPYRROLIDIN-1-YL) PYRIDINES AS MELANIN-CONCENTRATING HORMONE RECEPTOR AN TAGONISTS<br/>[FR] 2- (3-AMINOPYRROLIDIN-1-YL) PYRIDINES UTILISEES COMME ANTAGONISTES DU RECEPTEUR DE L'HORMONE CONCENTRANT LA MELANINE, ET COMPOSITIONS ET PROCEDES ASSOCIES
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2005103039A1

  公开（公告）日：2005-11-03

  Melanin-concentrating hormone (MCH) receptor antagonists are disclosed having utility for the treatment of MCH receptor-based disorders such as obesity. The compounds of this invention have the following structure: including stereoisomers, prodrugs, and pharmaceutically acceptable salts thereof, wherein R1, R2, R5, Het, X and Cyc are as defined herein. Also disclosed are compositions containing a compound of this invention, as well as methods relating to the use thereof.

  黑色素浓缩激素（MCH）受体拮抗剂被披露具有治疗基于MCH受体的疾病如肥胖的效用。本发明的化合物具有以下结构：包括立体异构体、前药和其药用盐，其中R1、R2、R5、Het、X和Cyc如本文所定义。还披露了含有本发明化合物的组合物，以及与其使用相关的方法。
• Therapeutic Agents
  申请人：Giordanetto Fabrizio

  公开号：US20080051405A1

  公开（公告）日：2008-02-28

  The present invention provides compounds of formula I, processes for preparing such compounds, their use in the treatment of obesity, psychiatric disorders, cognitive disorders, memory disorders, schizophrenia, epilepsy, and related conditions, type II diabetes, Metabolic syndrome and neurological disorders such as dementia, multiple sclerosis, Parkinson's disease, Huntington's chorea, Alzheimer's disease, and pain related disorders, and to pharmaceutical compositions containing them.

  本发明提供了公式I的化合物，制备这些化合物的方法，它们在治疗肥胖、精神障碍、认知障碍、记忆障碍、精神分裂症、癫痫以及相关疾病、2型糖尿病、代谢综合征和神经系统疾病如痴呆症、多发性硬化症、帕金森病、亨廷顿舞蹈症、阿尔茨海默病和与疼痛相关的疾病中的用途，以及含有它们的药物组合物。
• Melanin-concentrating hormone receptor antagonists and compositions and methods related thereto
  申请人：Goodfellow Val

  公开号：US20050256124A1

  公开（公告）日：2005-11-17

  Melanin-concentrating hormone (MCH) receptor antagonists are disclosed having utility for the treatment of MCH receptor-based disorders such as obesity. The compounds of this invention have the following structure: including stereoisomers, prodrugs, and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 5 , Het, X and Cyc are as defined herein. Also disclosed are compositions containing a compound of this invention, as well as methods relating to the use thereof.

  本发明揭示了具有治疗MCH受体基础疾病如肥胖症的功效的MCH受体拮抗剂。本发明的化合物具有以下结构：包括立体异构体、前药和其药学上可接受的盐，其中R1、R2、R5、Het、X和Cyc如本文所定义。本发明还揭示了含有本发明化合物的组合物，以及与其使用相关的方法。
• US7723331B2
  申请人：——

  公开号：US7723331B2

  公开（公告）日：2010-05-25
• A Thienopyridazinone-Based Melanin-Concentrating Hormone Receptor 1 Antagonist with Potent in Vivo Anorectic Properties
  作者：Brian Dyck、Stacy Markison、Liren Zhao、Junko Tamiya、Jonathan Grey、Martin W. Rowbottom、Mingzhu Zhang、Troy Vickers、Katie Sorensen、Christi Norton、Jenny Wen、Christopher E. Heise、John Saunders、Paul Conlon、Ajay Madan、David Schwarz、Val S. Goodfellow

  DOI：10.1021/jm051263c

  日期：2006.6.1

  Melanin-concentrating hormone receptor antagonists containing thieno- and a benzopyridazinone cores were designed and tested as potential anorectic agents. These ligands showed high affinity for the receptor, potent functional activity in vitro, and good oral bioavailabilty in rats. The thiophene analogue exhibited low iv clearance, long half-life, and high brain penetration. In obese rats, the thienopyridazinone demonstrated a dose-dependent reduction in feeding and body weight with doses between 1 and 10 mg kg(-1).