(R,S)-2-[4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-benzensulfonylamino-oxy]-propionic acid | 921617-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R,S)-2-[4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-benzensulfonylamino-oxy]-propionic acid
• 英文别名: 2-[[4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylamino]oxypropanoic Acid
• CAS: 921617-79-0；921617-91-6；921617-92-7
• 化学式: C₂₀H₁₈F₃N₃O₅S
• 分子量: 469.441
• InChiKey: WIENENPMVANVOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (R,S)-2-[4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-benzensulfonylamino-oxy]-propionic acid 在 麻黄素 作用下， 以 异丙醇 为溶剂， 以0.62 g的产率得到(+)-2-[4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonaminooxy]-propionic acid
  参考文献：
  名称：

  New Celecoxib Derivatives as Anti-Inflammatory Agents

  摘要：

  A series of 1,5-diarylpyrazoles with a substituted benzenesulfonamide moiety was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Some compounds, for example, (+/-)-2-[4-(5-p-tolyl-3-trifluoromethyl-pyrazole-1-yl)-benzenesulfonylaminooxy]-propionic acid 16 and its disodium salt 21, had a higher in vivo anti-inflammatory activity compared to celecoxib, despite having no in vitro COX-1 or COX-2 inhibitory activity. Their gastrointestinal side effect profile is essentially more favorable than that of celecoxib.

  DOI：

  10.1021/jm070821f
• 作为产物：
  描述：

  2-氨基氧基丙酸 、 4-[5-(4-甲基苯基)-3-三氟甲基-1H-吡唑-1-基]苯磺酰氯 在 sodium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 以85%的产率得到(R,S)-2-[4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-benzensulfonylamino-oxy]-propionic acid
  参考文献：
  名称：

  New Celecoxib Derivatives as Anti-Inflammatory Agents

  摘要：

  A series of 1,5-diarylpyrazoles with a substituted benzenesulfonamide moiety was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Some compounds, for example, (+/-)-2-[4-(5-p-tolyl-3-trifluoromethyl-pyrazole-1-yl)-benzenesulfonylaminooxy]-propionic acid 16 and its disodium salt 21, had a higher in vivo anti-inflammatory activity compared to celecoxib, despite having no in vitro COX-1 or COX-2 inhibitory activity. Their gastrointestinal side effect profile is essentially more favorable than that of celecoxib.

  DOI：

  10.1021/jm070821f

文献信息

• 1, 2-DIARYL PYRAZOLES USEFUL AS ANALGETIC AND ANTIINFLAMMATORY AGENTS
  申请人：Fischer Janos

  公开号：US20090036510A1

  公开（公告）日：2009-02-05

  The present invention relates to new compounds of formula (I), (I) wherein the meaning of R 1 is hydrogen atom, C 1 -C 5 acyl group, benzoyl group or R 2 —COOR 3 group, Y is hydrogen atom or alkali ion, R 2 is C 1 -C 4 straight or branched alkylidene group and R 3 is hydrogen atom, C 1 -C 4 alkyl group or alkali ion, and/or stereoisomers and/or diastereomers and/or pharmaceutically acceptable salts and/or hydrates and/or solvates thereof, which are suitable for the treatment of pain of acute and chronic inflammation origin as well as postoperative pain and dysmenorrhea. The invention also relates to the process of the synthesis of compounds of formula (I) as well as the pharmaceutical composition containing the same and the use for treatment of pain, inflammation and disorders associated with inflammation.

  本发明涉及公式（I）的新化合物，其中R1的含义是氢原子、C1-C5酰基、苯甲酰基或R2-COOR3基团，Y是氢原子或碱离子，R2是C1-C4直链或支链烷基亚甲基基团，R3是氢原子、C1-C4烷基或碱离子，以及/或其立体异构体和/或顺反异构体和/或药学上可接受的盐和/或水合物和/或溶剂物，适用于治疗急性和慢性炎症源性疼痛以及术后疼痛和痛经。本发明还涉及公式（I）化合物的合成过程，以及包含它们的制药组合物和用于治疗疼痛、炎症和与炎症有关的疾病的用途。
• WO2007/12906
  申请人：——

  公开号：——

  公开（公告）日：——
• NEW 1 , 2 -DIARYL PYRAZOLES USEFUL AS ANALGETIC AND ANTI-INFLAMMATORY AGENTS
  申请人：Richter Gedeon Nyrt.

  公开号：EP1915347B1

  公开（公告）日：2009-01-28
• US7723370B2
  申请人：——

  公开号：US7723370B2

  公开（公告）日：2010-05-25
• [EN] NEW 1 , 2 -DIARYL PYRAZOLES USEFUL AS ANALGETIC AND ANTI-INFLAMMATORY AGENTS<br/>[FR] NOUVEAUX 1, 2-DIARYL PYRAZOLES UTILES EN TANT QU'AGENTS ANALGÉSIQUES ET ANTI-INFLAMMATOIRES
  申请人：RICHTER GEDEON VEGYESZET

  公开号：WO2007012906A1

  公开（公告）日：2007-02-01

  [EN] The present invention relates to new compounds of formula (I), (I) wherein the meaning of R₁ is hydrogen atom, C₁-C₅ acyl group, benzoyl group or R₂- COOR₃ group, Y is hydrogen atom or alkali ion, R₂ is C₁-C₄ straight or branched alkylidene group and R₃ is hydrogen atom, C₁-C₄ alkyl group or alkali ion, and/or stereoisomers and/or diastereomers and/or pharmaceutically acceptable salts and/or hydrates and/or solvates thereof, which are suitable for the treatment of pain of acute and chronic inflammation origin as well as postoperative pain and dysmenorrhea. The invention also relates to the process of the synthesis of compounds of formula (I) as well as the pharmaceutical composition containing the same and the use for treatment of pain, inflammation and disorders associated with inflammation.
  [FR] La présente invention concerne de nouveaux composés de formule (I), (I) où la R₁ correspond à un atome d'hydrogène, un groupe acyle en C₁-C₅, un groupe benzoyle ou un groupe R₂- COOR₃, Y est un atome d'hydrogène ou un ion alcalin, R₂ est un groupe alkylidène linéaire ou ramifié en C₁-C₄ et R₃ est un atome d'hydrogène, un groupe alkyle en C₁-C₄ ou un ion alcalin, et/ou des stéréoisomères et/ou diastéréomères et/ou sels pharmaceutiquement acceptables et/ou hydrates et/ou solvates de ceux-ci, qui conviennent pour le traitement de la douleur résultant d'une inflammation aiguë et chronique ainsi que de la douleur postopératoire et de la dysménorrhée. L'invention concerne également le procédé de synthèse des composés de formule (I) ainsi que la composition pharmaceutique contenant ces derniers, ainsi que l'utilisation pour le traitement de la douleur, de l'inflammation et des troubles associés à l'inflammation.