Methyl 4-(dimethylamino)-5-(dimethylaminomethylideneamino)thieno[2,3-d]pyrimidine-6-carboxylate | 872890-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: Methyl 4-(dimethylamino)-5-(dimethylaminomethylideneamino)thieno[2,3-d]pyrimidine-6-carboxylate
• CAS: 872890-20-5
• 化学式: C₁₃H₁₇N₅O₂S
• 分子量: 307.376
• InChiKey: JLKNBZIILXQXEY-UHFFFAOYSA-N

物化性质

• 沸点：
  479.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 4-(dimethylamino)-5-(dimethylaminomethylideneamino)thieno[2,3-d]pyrimidine-6-carboxylate 、 2-甲基-4-甲氧基苯胺 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 13-(Dimethylamino)-5-(4-methoxy-2-methylphenyl)-8-thia-3,5,10,12-tetrazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,9,11-pentaen-6-one
  参考文献：
  名称：

  Synthesis and SAR development of novel mGluR1 antagonists for the treatment of chronic pain

  摘要：

  High throughput screening identified the pyridothienopyrimidinone 1 as a ligand for the metabotropic glutamate receptor 1 (mGluR1 = 10 nM). Compound 1 has an excellent in vivo profile; however, it displays unfavorable pharmacokinetic issues and metabolic stability. Therefore, using 1 as a template, novel analogues (10i) were prepared. These analogues displayed improved oral exposure and activity in the Spinal Nerve Ligation (SNL) pain model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.048
• 作为产物：
  描述：

  5-amino-4-carboxymethylthiothieno<2,3-d>pyrimidine-6-carboxylic acid, 4,6-dimethyl ester 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 Methyl 4-(dimethylamino)-5-(dimethylaminomethylideneamino)thieno[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis and SAR development of novel mGluR1 antagonists for the treatment of chronic pain

  摘要：

  High throughput screening identified the pyridothienopyrimidinone 1 as a ligand for the metabotropic glutamate receptor 1 (mGluR1 = 10 nM). Compound 1 has an excellent in vivo profile; however, it displays unfavorable pharmacokinetic issues and metabolic stability. Therefore, using 1 as a template, novel analogues (10i) were prepared. These analogues displayed improved oral exposure and activity in the Spinal Nerve Ligation (SNL) pain model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.048

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。
• 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。
• mGluR1 ANTAGONISTS AS THERAPEUTIC AGENTS
  申请人：Matasi Julius J.

  公开号：US20090192178A1

  公开（公告）日：2009-07-30

  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.
• US7485648B2
  申请人：——

  公开号：US7485648B2

  公开（公告）日：2009-02-03
• US7598259B2
  申请人：——

  公开号：US7598259B2

  公开（公告）日：2009-10-06