4-(4-(Methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amine | 354807-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-(Methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amine
• 英文别名: 4-(4-methylsulfonylphenyl)-6-(trifluoromethyl)pyrimidin-2-amine
• CAS: 354807-01-5
• 化学式: C₁₂H₁₀F₃N₃O₂S
• 分子量: 317.292
• InChiKey: YSWMQMATRUHISF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-(4-(Methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amine 以 甲酸 为溶剂， 反应 19.0h， 生成 4-[4-(Methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidin-2-ylformamide
  参考文献：
  名称：

  Pyrimidine derivatives as selective inhibitors of COX-2

  摘要：

  本发明提供了公式（I）的化合物及其药学上可接受的衍生物，其中：R1和R2分别选自H或C1-6烷基；R3是C1-6烷基或NH2；R4是H或C1-6烷基；A是5-或6-成员芳基，或5-或6-成员芳基取代一个或多个R5；R5是卤素，C1-6烷基，C1-6烷基取代一个或多个F，C1-6烷氧基，C1-6烷氧基取代一个或多个F，SO2NH2或SO2C1-6烷基；n为1至4。

  公开号：

  US06780870B2
• 作为产物：
  描述：

  2-(methylsulfonyl)-4-(4-(methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidine 在 氨 作用下， 以 乙腈 为溶剂， 生成 4-(4-(Methylsulfonyl)phenyl)-6-(trifluoromethyl)pyrimidin-2-amine
  参考文献：
  名称：

  Identification of [4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-pyrimidinyl] amines and ethers as potent and selective cyclooxygenase-2 inhibitors

  摘要：

  A novel series of [4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-pyrimidine-based cyclooxygenase-2 (COX-2) inhibitors, which have a different arrangement of substituents compared to the more common 1,2-diarylheterocycle based molecules, have been discovered. For example, 2-(butyloxy)-4-[4(methylsulfonyl) phenyl]-6-(trifluoromethyl) pyrimidine (47), a member of the 2- pyrimidinyl ether series, has been shown to be a potent and selective inhibitor with a favourable pharmacokinetic pro. le, high brain penetration and good efficacy in rat models of hypersensitivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.085

文献信息

• Pyrmidine derivatives as selective inhibitors of cox-2
  申请人：——

  公开号：US20030109538A1

  公开（公告）日：2003-06-12

  The invention provides the compounds of formula (I) and pharmaceutically acceptable derivatives thereof, in which: R 1 and R 2 are independently selected from H, or C 1-6 alkyl, R 3 is C 1-6 alkyl or NH 2 : R 4 is H or C 1-6 alkyl: A is and 5- or 6-membered aryl, or a 5- or 6-membered aryl substituted by one or more R 5 ; R 5 is halogen, C 1-6 alkyl, C 1-6 alkyl substituted by one ore more F, C 1-6 alkoxy, C 1-6 alkoxy substituted by one or more F, SO 2 NH 2 or SO 2 C 1-6 alkyl; and n is 1 to 4. Compounds of formula (I) are potent and selective inhibitors of COX-2 and are of use in the treatment of the pain, fever, inflammation of a variety of conditions and diseases.

  该发明提供了公式（I）的化合物及其在药学上可接受的衍生物，其中：R1和R2分别选自H或C1-6烷基，R3为C1-6烷基或NH2；R4为H或C1-6烷基；A为5-或6-成员芳基，或由一个或多个R5取代的5-或6-成员芳基；R5为卤素、C1-6烷基、由一个或多个F取代的C1-6烷基、C1-6烷氧基、由一个或多个F取代的C1-6烷氧基、SO2NH2或SO2C1-6烷基；n为1至4。公式（I）的化合物是COX-2的有效选择性抑制剂，并可用于治疗各种疾病和情况的疼痛、发热和炎症。
• PYRIMIDINE DERIVATIVES AS SELECTIVE INHIBITORS OF COX-2
  申请人：GLAXO GROUP LIMITED

  公开号：EP1254119A1

  公开（公告）日：2002-11-06
• US6780870B2
  申请人：——

  公开号：US6780870B2

  公开（公告）日：2004-08-24
• [EN] PYRIMIDINE DERIVATIVES AS SELECTIVE INHIBITORS OF COX-2<br/>[FR] DERIVES DE PYRIMIDINE UTILISES COMME INHIBITEURS DE LA COX-2
  申请人：GLAXO GROUP LTD

  公开号：WO2001058881A1

  公开（公告）日：2001-08-16

  The invention provides the compounds of formula (I) and pharmaceutically acceptable derivatives thereof, in which: R?1 and R2¿ are independently selected from H, or C¿1-6?alkyl; R?3¿ is C¿1-6?alkyl or NH2; R?4¿ is H or C¿1-6?alkyl; A is a 5- or 6-membered aryl, or a 5- or 6-membered aryl substituted by one or more R?5; R5¿ is halogen, C¿1-6?alkyl, C1-6alkyl substituted by one or more F, C1-6alkoxy, C1-6alkoxy substituted by one or more F, SO2NH2 or SO2C1-6alkyl; and n is 1 to 4. Compounds of formula (I) are potent and selective inhibitors of COX-2 and are of use in the treatment of the pain, fever, inflammation of a variety of conditions and diseases.
• Identification of [4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-pyrimidinyl] amines and ethers as potent and selective cyclooxygenase-2 inhibitors
  作者：Martin E. Swarbrick、Paul J. Beswick、Robert J. Gleave、Richard H. Green、Sharon Bingham、Chas Bountra、Malcolm C. Carter、Laura J. Chambers、Iain P. Chessell、Nick M. Clayton、Sue D. Collins、John A. Corfield、C. David Hartley、Savvas Kleanthous、Paul F. Lambeth、Fiona S. Lucas、Neil Mathews、Alan Naylor、Lee W. Page、Jeremy J. Payne、Neil A. Pegg、Helen S. Price、John Skidmore、Alexander J. Stevens、Richard Stocker、Sharon C. Stratton、Alastair J. Stuart、Joanne O. Wiseman

  DOI：10.1016/j.bmcl.2009.02.085

  日期：2009.8

  A novel series of [4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-pyrimidine-based cyclooxygenase-2 (COX-2) inhibitors, which have a different arrangement of substituents compared to the more common 1,2-diarylheterocycle based molecules, have been discovered. For example, 2-(butyloxy)-4-[4(methylsulfonyl) phenyl]-6-(trifluoromethyl) pyrimidine (47), a member of the 2- pyrimidinyl ether series, has been shown to be a potent and selective inhibitor with a favourable pharmacokinetic pro. le, high brain penetration and good efficacy in rat models of hypersensitivity. (C) 2009 Elsevier Ltd. All rights reserved.