4-[2-(6-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[2-(6-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide
• 英文别名: 4-(2-(6-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl)benzenesulfonamide；4-[2-(6-Methyl-pyridin-3-yl)-4-trifluoromethyl-imidazol-1-yl]-benzenesulfonamide；4-[2-(6-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide
• 化学式: C₁₆H₁₃F₃N₄O₂S
• 分子量: 382.366
• InChiKey: FVYLDRLDRJJWDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-methyl-5-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 4-[2-(6-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Selective Cyclooxygenase-2 Inhibitors:  Heteroaryl Modified 1,2-Diarylimidazoles Are Potent, Orally Active Antiinflammatory Agents

  摘要：

  A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no CI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.

  DOI：

  10.1021/jm0000719

文献信息

• Compositions of a cyclooxygenase-2 selective inhibitor and a sodium ion channel blocker for the treatment of pain, inflammation or inflammation mediated disorders
  申请人：Pharmacia Corporation

  公开号：US20040220187A1

  公开（公告）日：2004-11-04

  The present invention provides compositions and methods for the treatment of pain, inflammation or inflammation-mediated disorders in a subject. More particularly, the invention provides a combination therapy for the treatment of pain, inflammation or inflammation mediated disorders comprising the administration to a subject of a sodium ion channel blocker in combination with a cyclooxygenase-2 selective inhibitor.

  本发明提供了用于治疗疼痛、炎症或炎症介导性疾病的组合物和方法。更具体地，本发明提供了一种联合疗法，用于治疗疼痛、炎症或炎症介导性疾病，包括向受试者施用钠离子通道阻滞剂与环氧合酶-2选择性抑制剂的组合。
• Combination of a Cox-2 inhibitor and a DNA topoisomerase I inhibitor for treatment of neoplasia
  申请人：Masferrer L. Jaime

  公开号：US20050187172A1

  公开（公告）日：2005-08-25

  The present invention provides combinations of a Cox-2 inhibitor and a DNA topoisomerase inhibitor and methods of use thereof for preventing and/or treating neoplasia or or a neoplasia-related disorder in a subject.

  本发明提供了一种COX-2抑制剂和DNA拓扑异构酶抑制剂的组合物，以及它们的使用方法，用于预防和/或治疗受试者中的肿瘤或与肿瘤相关的疾病。
• Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith
  申请人：Pulaski P. Steven

  公开号：US20050014729A1

  公开（公告）日：2005-01-20

  A method for preventing or treating dermatological disorders and dermatological disorder-related complications in a subject involves a monotherapy with a Cox-2 inhibitor or a combination therapy with a Cox-2 inhibitor and a dermatological treatment agent. Also described are therapeutic compositions comprising a Cox-2 inhibitor and a dermatological treatment agent. Pharmaceutical compositions and kits for implementing the present method are also described.

  一种预防或治疗受试者的皮肤病和与皮肤病相关并发症的方法涉及使用Cox-2抑制剂进行单独治疗或与Cox-2抑制剂和皮肤治疗剂的联合治疗。还描述了包含Cox-2抑制剂和皮肤治疗剂的治疗组合物。还描述了用于实施本方法的药物组合物和工具包。
• Method for the treatment and prevention of pain and inflammation with glucosamine and a cyclooxygenase-2 selective inhibitor and compositions therefor
  申请人：Pharmacia Corporation

  公开号：US20030114418A1

  公开（公告）日：2003-06-19

  A method of treating, preventing, or inhibiting pain, inflammation or inflammation-associated disorder in a subject in need of such treatment or prevention provides for treating the subject with glucosamine and a cyclooxygenase-2 selective inhibitor or prodrug thereof, wherein the amount of glucosamine and the amount of a cyclooxygenase-2 selective inhibitor or prodrug thereof together constitute a pain or inflammation suppressing treatment or prevention effective amount of the composition. Compositions and pharmaceutical compositions that contain glucosamine and a cyclooxygenase-2 selective inhibitor are also disclosed.

  一种治疗、预防或抑制需要此类治疗或预防的受试者的疼痛、炎症或与炎症相关疾病的方法包括使用氨基葡萄糖和环氧合酶-2选择性抑制剂或其前药来治疗受试者，其中氨基葡萄糖的量和环氧合酶-2选择性抑制剂或其前药的量共同构成组合物的疼痛或炎症抑制治疗或预防的有效量。还公开了含有氨基葡萄糖和环氧合酶-2选择性抑制剂的组合物和药物组合物。
• Method and compositions for the treatment and prevention of pain and inflammation with a cyclooxygenase-2 selective inhibitor and chondroitin sulfate
  申请人：Pharmacia Corporation

  公开号：US20030114416A1

  公开（公告）日：2003-06-19

  A method of treating, preventing, or inhibiting pain, inflammation or inflammation-associated disorder in a subject in need of such treatment or prevention provides for treating the subject with chondroitin sulfate and a cyclooxygenase-2 selective inhibitor, or a prodrug thereof, wherein the amount of chondroitin sulfate and the amount of a cyclooxygenase-2 selective inhibitor or a pharmaceutically acceptable salt or prodrug thereof together constitute a pain or inflammation suppressing treatment or prevention effective amount. Glucosamine can optionally be present. Compositions that contain the combination of chondroitin sulfate and cyclooxygenase-2 selective inhibitor and, optionally, the glucosamine, are disclosed, as are pharmaceutical compositions.

  一种治疗、预防或抑制疼痛、炎症或与炎症相关疾病的方法，适用于需要此类治疗或预防的受试者，包括使用软骨素硫酸和环氧合酶-2选择性抑制剂或其前药来治疗受试者，其中软骨素硫酸的数量和环氧合酶-2选择性抑制剂或其药用可接受的盐或前药的数量共同构成有效的疼痛或炎症抑制治疗或预防量。可选择添加氨基葡萄糖。公开了含有软骨素硫酸和环氧合酶-2选择性抑制剂以及可选地氨基葡萄糖的组合的组合物，以及药物组合物。