ethyl 6-chloro-7-[isobutyl(methyl)amino]-2-(trifluoromethyl)-2H-chromene-3-carboxylate | 775331-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 6-chloro-7-[isobutyl(methyl)amino]-2-(trifluoromethyl)-2H-chromene-3-carboxylate
• 英文别名: ethyl 6-chloro-7-[methyl(2-methylpropyl)amino]-2-(trifluoromethyl)-2H-chromene-3-carboxylate
• CAS: 775331-19-6
• 化学式: C₁₈H₂₁ClF₃NO₃
• 分子量: 391.818
• InChiKey: HNBYASGFGQVSDE-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±45.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-chloro-7-[isobutyl(methyl)amino]-2-(trifluoromethyl)-2H-chromene-3-carboxylate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 6-chloro-7-[isobutyl(methyl)amino]-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid
  参考文献：
  名称：

  The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part 2: The second clinical candidate having a shorter and favorable human half-life

  摘要：

  In this Letter, we provide the structure-activity relationships, optimization of design, testing criteria, and human half-life data for a series of selective COX-2 inhibitors. During the course of our structure-based drug design efforts, we discovered two distinct binding modes within the COX-2 active site for differently substituted members of this class. The challenge of a undesirably long human half-life for the first clinical candidate 1 t(1/2) = 360 h was addressed by multiple strategies, leading to the discovery of 29b-(S) (SC-75416) with t(1/2) = 34 h. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.054
• 作为产物：
  描述：

  ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate 、 N-甲基异丁基胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以64%的产率得到ethyl 6-chloro-7-[isobutyl(methyl)amino]-2-(trifluoromethyl)-2H-chromene-3-carboxylate
  参考文献：
  名称：

  [EN] SUBSTITUTED CYCLOPROPYL CHROMENE COMPOUNDS FOR USE IN THE TREATMENT AND PREVENTION OF INFLAMMATION RELATED CONDITIONS
  [FR] COMPOSES DE CYCLOPROPYL CHROMENE SUBSTITUES DESTINES A ETRE UTILISES DANS LE TRAITEMENT ET LA PREVENTION DE PATHOLOGIES LIEES A DES INFLAMMATIONS

  摘要：

  本发明涉及在与环氧合酶-2介导的疾病相关的情况治疗中具有效用的方法和化合物。特别感兴趣的化合物是由式（1）定义的苯并吡喃和它们的类似物，其中Z、X、R1、R2、R3和R4如规范中所述。

  公开号：

  WO2006040672A1

文献信息

• [EN] CHROMENE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] DERIVES DE CHROMENE A TITRE D'AGENTS ANTI-INFLAMMATOIRES
  申请人：PHARMACIA CORP

  公开号：WO2004087687A1

  公开（公告）日：2004-10-14

  The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (I). Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.

  该发明涉及在治疗与环氧合酶-2介导的疾病相关的情况中具有效用的方法和化合物。特别感兴趣的化合物是由式(I)定义的苯并吡喃和它们的类似物。其中Z、X、R1、R2、R3和R4如规范中所述。
• [EN] SUBSTITUTED CYCLOPROPYL CHROMENE COMPOUNDS FOR USE IN THE TREATMENT AND PREVENTION OF INFLAMMATION RELATED CONDITIONS<br/>[FR] COMPOSES DE CYCLOPROPYL CHROMENE SUBSTITUES DESTINES A ETRE UTILISES DANS LE TRAITEMENT ET LA PREVENTION DE PATHOLOGIES LIEES A DES INFLAMMATIONS
  申请人：PHARMACIA & UPJOHN CO LLC

  公开号：WO2006040672A1

  公开（公告）日：2006-04-20

  The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (1) Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.

  本发明涉及在与环氧合酶-2介导的疾病相关的情况治疗中具有效用的方法和化合物。特别感兴趣的化合物是由式（1）定义的苯并吡喃和它们的类似物，其中Z、X、R1、R2、R3和R4如规范中所述。
• Benzopyran compounds useful for treating inflammatory conditions
  申请人：Carter Jeffery

  公开号：US20050148777A1

  公开（公告）日：2005-07-07

  The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula 1 Wherein Z, X, R 1 , R 2, R 3 , and R 4 are as described in the specification.

  本发明涉及与环氧合酶-2介导的疾病相关的病症治疗方法和化合物。特别感兴趣的化合物是由公式1定义的苯并吡喃和其类似物，其中Z、X、R1、R2、R3和R4如规范中所述。
• Benzopyran compounds for use in the treatment and prevention of inflammation related conditions
  申请人：Carter Jeffery

  公开号：US20050148627A1

  公开（公告）日：2005-07-07

  The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula 1 Wherein Z, X, R 1 , R 2 , R 3 , and R 4 are as described in the specification.

  本发明涉及用于治疗与环氧合酶-2介导的疾病相关的条件的方法和化合物。特别感兴趣的化合物是苯并吡喃和它们的类似物，其由公式1定义，其中Z、X、R1、R2、R3和R4如规范中所述。
• [EN] BENZOPYRAN COMPOUNDS USEFUL FOR TREATING INFLAMMATORY CONDITIONS<br/>[FR] COMPOSES BENZOPYRANIQUES UTILISABLES DANS LE TRAITEMENT DES PATHOLOGIES INFLAMMATOIRES
  申请人：PHARMACIA CORP

  公开号：WO2004087686A3

  公开（公告）日：2004-12-16