4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide | 177660-95-6

• 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-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide
• 英文别名: 4-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamide；4-[2-pyridin-3-yl-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide
• CAS: 177660-95-6
• 化学式: C₁₅H₁₁F₃N₄O₂S
• 分子量: 368.339
• InChiKey: LWPSCKOHFHYVBN-UHFFFAOYSA-N

物化性质

• 熔点：
  219-221 °C
• 沸点：
  574.2±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-二甲氨基吡啶 、 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide 在 乙酸酐 、 三乙胺 作用下， 以 水 为溶剂， 以0.5 g (90%)的产率得到N-[[4-[2-(3-pyridinyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]phenyl]sulfonyl]acetamide
  参考文献：
  名称：

  Prodrugs of benzenesulfonamide-containing COX-2 inhibitors

  摘要：

  COX-2抑制剂的前药被描述为在治疗炎症和与炎症相关的疾病方面很有用。

  公开号：

  US05932598A1
• 作为产物：
  描述：

  3-氰基吡啶 在 Oxone 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 异丙醇 为溶剂， 反应 19.5h， 生成 4-[2-(pyridin-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

• Combination therapy for the treatment of cancer
  申请人：Pharmacia Corporation

  公开号：US20030216410A1

  公开（公告）日：2003-11-20

  The present invention relates to methods for treatment or prevention of neoplasia disorders using protein tyrosine kinase inhibitors in combination with cyclooxygenase inhibitors, in particular cyclooxygenase-2 selective inhibitors.

  本发明涉及使用蛋白酪氨酸激酶抑制剂与环氧合酶抑制剂，特别是环氧合酶-2选择性抑制剂，联合治疗或预防肿瘤性疾病的方法。
• Antiangiogenic combination therapy for the treatment of cancer
  申请人：——

  公开号：US20020103141A1

  公开（公告）日：2002-08-01

  The present invention provides combinations of a DNA topoisomerase I inhibiting agent and a selective COX-2 inhibiting agent for preventing, treating, and/or reducing the risk of developing a neoplasia disorder in a mammal.

  本发明提供了一种DNA拓扑异构酶I抑制剂和选择性COX-2抑制剂的组合物，用于预防、治疗和/或减少哺乳动物发生肿瘤性疾病的风险。
• [EN] CANNABINOID ACID ESTER COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSITIONS D'ESTER D'ACIDE CANNABINOÏDE ET LEURS UTILISATIONS
  申请人：EPM GROUP INC

  公开号：WO2020186010A1

  公开（公告）日：2020-09-17

  The present disclosure provides pharmaceutical compositions including a cannabinoid acid ester compound alone or in combination with one or more additional cannabinoid compounds. In some embodiments, the cannabinoid acid ester compound is a cannabidiolic acid ester. A variety of therapeutic applications in which the cannabinoid acid ester compounds and pharmaceutical compositions find use are also provided, including combination therapies using cannabinoid acid ester compounds and one or more additional therapeutic agents.

  本公开提供了包括大麻酸酯化合物在内或与一个或多个额外的大麻化合物结合的药物组合物。在一些实施例中，大麻酸酯化合物是大麻二酚酸酯。还提供了大麻酸酯化合物和药物组合物在多种治疗应用中的使用，包括使用大麻酸酯化合物和一个或多个额外治疗剂的联合疗法。
• Method for the treatment and prevention of cachexia
  申请人：Washington University

  公开号：US20030087942A1

  公开（公告）日：2003-05-08

  Cachexia, including anorexia and other forms of weight loss, is a frequent complication of acute and chronic infections, and result from induction of cytokines, prostaglandins, and other inflammatory mediators that are critical for pathogen elimination. The present invention includes methods for the treatment or prevention of cachexic conditions while maintaining the production of factors essential for infection control through the administration of an effective amount of a cyclooxygenase-2 selective inhibiting compound.

  消瘦症，包括厌食和其他形式的体重减轻，是急性和慢性感染的常见并发症，由细胞因子、前列腺素和其他炎症介质的诱导引起，这些介质对病原体清除至关重要。本发明包括通过给予有效量的环氧合酶-2选择性抑制化合物来治疗或预防消瘦症状，同时保持对感染控制至关重要的因子的产生的方法。
• Heterocyclo-substituted imidazoles for the treatment of inflammation
  申请人：Khanna K. Ish

  公开号：US20050096368A1

  公开（公告）日：2005-05-05

  A class of imidazolyl compounds is described for use in treating inflammation. Compounds of particular interest are defined by formula (V), wherein R 3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy. aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R 4 is a radical selected from hydrido, alkyl and halo; and wherein R 13 and R 14 are independently selected from aryl and heterocyclo, wherein R 13 and R 14 are optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro; provided at least one of R 13 and R 14 is aryl substituted with alkylsulfonyl or aminosulfonyl; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑基化合物用于治疗炎症。特别感兴趣的化合物由公式（V）定义，其中R3是从氢基，烷基，卤代烷基，芳基烷基，杂环烷基，杂环芳基烷基，酰基，氰基，烷氧基，烷硫基，烷硫基烷基，烷基磺酰基，环烷硫基，环烷硫基烷基，环烷磺酰基，环烷磺酰基烷基，卤代烷基磺酰基，芳基磺酰基，卤代基，羟基烷基，烷氧基烷基，烷基羧酰基，芳基羧酰基，芳基烷基羧酰基，杂环羧酰基，氰基烷基，氨基烷基，烷基氨基烷基，N-芳基氨基烷基，N-烷基-N-芳基氨基烷基，羧基烷基，烷氧基羧酰基烷基，烷氧基羧酰基，卤代烷基羧酰基，羧基，氨基羧酰基，烷基氨基羧酰基，杂环芳基烷氧基烷基，杂环芳基氧基烷基，杂环芳基硫基烷基，芳基硫醇基烷基，芳基氧基烷基，芳基硫醇基，芳基氧基。芳基烷硫基烷基，芳基烷氧基烷基，芳基和杂环芳基;其中R4是从氢基，烷基和卤代基中选择的基团;并且R13和R14分别从芳基和杂环芳基中选择，其中R13和R14在可取代位置上可以选择一个或多个基团独立地选择，包括烷基磺酰基，氨基磺酰基，卤代基，烷硫基，烷基，氰基，羧基，烷氧基羧酰基，卤代烷基，羟基，烷氧基，羟基烷基，烷氧基烷基，卤代烷氧基，氨基，烷基氨基，芳基氨基和硝基; 提供至少一个R13和R14被烷基磺酰基或氨基磺酰基取代的芳基，或其药学上可接受的盐。