2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxylic acid | 1006037-08-6

• 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: 2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxylic acid
• 英文别名: 2,5-Dimethyl-4-(4-(trifluoromethyl)benzyl)thiophene-3-carboxylic acid；2,5-dimethyl-4-[[4-(trifluoromethyl)phenyl]methyl]thiophene-3-carboxylic acid
• CAS: 1006037-08-6
• 化学式: C₁₅H₁₃F₃O₂S
• 分子量: 314.328
• InChiKey: WBADBJDOSDVJBE-UHFFFAOYSA-N

物化性质

• 沸点：
  392.3±37.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxylic acid 在 N,N-二甲基甲酰胺 草酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2,5-Dimethyl-4-[[4-(trifluoromethyl)phenyl]methyl]thiophene-3-carbonyl chloride
  参考文献：
  名称：

  [EN] PROCESS FOR MAKING THIOPHENE CARBOXAMIDE DERIVATIVE
  [FR] PROCÉDÉ POUR FABRIQUER UN DÉRIVÉ DE CARBOXAMIDE DE THIOPHÈNE

  摘要：

  这项发明涵盖了一种制备噻吩羧酰胺衍生物的过程，这是一种用于治疗疼痛和炎症的EP4拮抗剂。

  公开号：

  WO2009020588A1
• 作为产物：
  描述：

  二氧化碳 在 正丁基锂 、 盐酸 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.75h， 生成 2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxylic acid
  参考文献：
  名称：

  WO2008/17164

  摘要：

  公开号：

文献信息

• THIOPHENECARBOXAMIDE DERIVATIVES AS EP4 RECEPTOR LIGANDS
  申请人：Blouin Marc

  公开号：US20090247596A1

  公开（公告）日：2009-10-01

  The invention is directed to thiophenecarboxamide derivatives of formulae I and II as EP4 receptor ligands, antagonists or agonists, useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoid arthritis, cancer and glaucoma. Pharmaceutical compositions and methods of use are also included. (Formulas I and II).

  本发明涉及公式I和II的噻吩羧酰胺衍生物，作为EP4受体配体、拮抗剂或激动剂，用于治疗EP4介导的疾病或症状，如急性和慢性疼痛、骨关节炎、类风湿性关节炎、癌症和青光眼。还包括药物组合物和使用方法。(公式I和II)
• Thiophenecarboxamide derivatives as EP4 receptor ligands
  申请人：Blouin Marc

  公开号：US08969394B2

  公开（公告）日：2015-03-03

  The invention is directed to thiophenecarboxamide derivatives of formulae I and II as EP4 receptor ligands, antagonists or agonists, useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoid arthritis, cancer and glaucoma. Pharmaceutical compositions and methods of use are also included. (Formulas I and II).

  本发明涉及公式I和II的噻吩羧酰胺衍生物作为EP4受体配体、拮抗剂或激动剂，用于治疗EP4介导的疾病或病状，如急性和慢性疼痛、骨关节炎、类风湿性关节炎、癌症和青光眼。还包括药物组合物和使用方法。（公式I和II）
• Scalable Synthesis of a Prostaglandin EP4 Receptor Antagonist
  作者：Danny Gauvreau、Sarah J. Dolman、Greg Hughes、Paul D. O’Shea、Ian W. Davies

  DOI：10.1021/jo1004197

  日期：2010.6.18

  The evolution of scalable, economically viable synthetic approaches to the potent and selective prostaglandin EP4 antagonist 1 is presented. The chromatography-free synthesis of multikilogram quantities of 1 using a seven-step sequence (six in the longest linear sequence) is described. This approach has been further modified in an effort to identify a long-term manufacturing route. Our final synthesis involves no step requiring cryogenic (< - 25 degrees C) conditions; comprises a total of four steps, only three of which are in the longest linear synthesis; and features the use of two consecutive iron-catalyzed Friedel-Crafts substitutions.
• The Discovery of 4-{1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic Acid (MK-2894), A Potent and Selective Prostaglandin E₂ Subtype 4 Receptor Antagonist
  作者：Marc Blouin、Yongxin Han、Jason Burch、Julie Farand、Christophe Mellon、Mireille Gaudreault、Mark Wrona、Jean-François Lévesque、Danielle Denis、Marie-Claude Mathieu、Rino Stocco、Erika Vigneault、Alex Therien、Patsy Clark、Steve Rowland、Daigen Xu、Gary O’Neill、Yves Ducharme、Rick Friesen

  DOI：10.1021/jm901771h

  日期：2010.3.11

  The discovery of highly potent and selective second generation EP4 antagonist MK-2894 (34d) is discussed. This compound exhibits favorable pharmacokinetic profile in a number of preclinical species and potent anti-inflammatory activity in several animal models of pain/inflammation. It also shows favorable GI tolerability profile in rats when compared to traditional NSAID indomethacin.
• PROCESS FOR MAKING THIOPHENE CARBOXAMIDE DERIVATIVES
  申请人：DAVIES Ian

  公开号：US20100204487A1

  公开（公告）日：2010-08-12

  The invention encompasses a process for making a thiophene carboxamide derivative, which is an EP4 antagonist useful for treating pain and inflammation.