5-amino-4-dimethylaminothieno[8,9-b]benzo-6-carboxylic acid methyl ester | 869802-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-amino-4-dimethylaminothieno[8,9-b]benzo-6-carboxylic acid methyl ester
• 英文别名: Methyl 3-amino-4-(dimethylamino)-1-benzothiophene-2-carboxylate
• CAS: 869802-23-3
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: XEUMARTZNCYBHW-UHFFFAOYSA-N

物化性质

• 沸点：
  413.1±40.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-4-dimethylaminothieno[8,9-b]benzo-6-carboxylic acid methyl ester 在 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 32.0h， 生成 9-(dimethylamino)-3-(4-ethylphenyl)[1]benzothieno[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Structure−Activity Relationship of Triazafluorenone Derivatives as Potent and Selective mGluR1 Antagonists

  摘要：

  SAR (structure -activity relationship) studies of triazafluorenone derivatives as potent mGIuR1 antagonists are described. The triazafluorenone derivatives are non-amino acid derivatives and noncompetitive mGluR1 antagonists that bind at a putative allosteric recognition site located within the seven-transmembrane domain of the receptor. These triazafluorenone derivatives are potent, selective, and systemically active mGluR1 antagonists. Compound 1n, for example, was a very potent mGIuR1 antagonist IC50 = 3 nM) and demonstrated full efficacy in various in vivo animal pain models.

  DOI：

  10.1021/jm0504407
• 作为产物：
  描述：

  2,6-二硝基氯苯 在 sodium methylate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 生成 5-amino-4-dimethylaminothieno[8,9-b]benzo-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure−Activity Relationship of Triazafluorenone Derivatives as Potent and Selective mGluR1 Antagonists

  摘要：

  SAR (structure -activity relationship) studies of triazafluorenone derivatives as potent mGIuR1 antagonists are described. The triazafluorenone derivatives are non-amino acid derivatives and noncompetitive mGluR1 antagonists that bind at a putative allosteric recognition site located within the seven-transmembrane domain of the receptor. These triazafluorenone derivatives are potent, selective, and systemically active mGluR1 antagonists. Compound 1n, for example, was a very potent mGIuR1 antagonist IC50 = 3 nM) and demonstrated full efficacy in various in vivo animal pain models.

  DOI：

  10.1021/jm0504407

文献信息

• mGluR1 antagonists as therapeutic agents
  申请人：Matasi J. Julius

  公开号：US20060009477A1

  公开（公告）日：2006-01-12

  In its many embodiments, the present invention provides tricyclic compounds of formula I (wherein J 1 -J 4 , X, and R 1 —R 5 are as defined herein) useful as metabotropic glutamate receptor (mGluR) antagonists, particularly as selective metabotropic glutamate receptor 1 antagonists, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds and compositions to treat diseases associated with metabotropic glutamate receptor (e.g., mGluR1) such as, for example, pain, migraine, anxiety, urinary incontinence and neurodegenerative diseases such Alzheimer's disease.

  在其多种实施方式中，本发明提供了式I的三环化合物（其中J1-J4、X和R1—R5如本文所定义）作为代谢型谷氨酸受体（mGluR）拮抗剂，特别是作为选择性代谢型谷氨酸受体1拮抗剂，含有该化合物的药物组合物，以及使用该化合物和组合物治疗与代谢型谷氨酸受体（例如mGluR1）相关的疾病的方法，例如疼痛、偏头痛、焦虑、尿失禁和阿尔茨海默病等神经退行性疾病。
• [EN] TRICYCLIC COMPOUNDS AND THEIR USE AS MGLUR1 ANTAGONISTS<br/>[FR] COMPOSES TRICYCLIQUES ET LEUR UTILISATION COMME ANTAGONISTES DU MGLUR1
  申请人：SCHERING CORP

  公开号：WO2006002051A1

  公开（公告）日：2006-01-05

  In its many embodiments, the present invention provides tricyclic compounds of Formula (I) (wherein J1-J4, X, and R1-R5 are as defined herein) useful as metabotropic glutamate receptor (mGluR) antagonists, particularly as selective metabotropic glutamate receptor 1 antagonists, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds and compositions to treat diseases associated with metabotropic glutamate receptor (e.g., mGluR1) such as, for example, pain, migraine, anxiety, urinary incontinence and neurodegenerative diseases such Alzheimer's disease.

  在其多种实施方式中，本发明提供了式(I)的三环化合物（其中J1-J4，X和R1-R5如本文所定义），作为代谢型谷氨酸受体（mGluR）拮抗剂，特别是选择性代谢型谷氨酸受体1拮抗剂，含有该化合物的制药组合物，以及使用该化合物和组合物治疗与代谢型谷氨酸受体（例如mGluR1）相关的疾病的治疗方法，如疼痛，偏头痛，焦虑，尿失禁和神经退行性疾病，例如阿尔茨海默病。
• mGluR1 Antagonists as therapeutic agents
  申请人：Matasi J. Julius

  公开号：US20060167029A1

  公开（公告）日：2006-07-27

  In its many embodiments, the present invention provides tricyclic compounds of formula I (wherein J 1 -J 4 , X, and R 1 -R 5 are as defined herein) useful as metabotropic glutamate receptor (mGluR) antagonists, particularly as selective metabotropic glutamate receptor 1 antagonists, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds and compositions to treat diseases associated with metabotropic glutamate receptor (e.g., mGluR1) such as, for example, pain, migraine, anxiety, urinary incontinence and neurodegenerative diseases such Alzheimer's disease.

  在许多实施方案中，本发明提供了式 I 的三环化合物（其中 J 1 -J 4 、X 和 R 1 -R 5 如本文所定义）作为代谢型谷氨酸受体（mGluR）拮抗剂，特别是作为选择性代谢型谷氨酸受体 1 拮抗剂，含有这些化合物的药物组合物，以及使用这些化合物和组合物治疗与代谢型谷氨酸受体（如 mGluR1）相关疾病（如疼痛、偏头痛、焦虑、尿失禁和神经退行性疾病，如阿尔茨海默病）的方法。
• TRICYCLIC COMPOUNDS AND THEIR USE AS MGLUR1 ANTAGONISTS
  申请人：Schering Corporation

  公开号：EP1765829B1

  公开（公告）日：2010-07-07
• MGLUR1 ANATGONISTS AS THERAPEUTIC AGENTS
  申请人：Schering Corporation

  公开号：EP1966220B1

  公开（公告）日：2011-01-26