2-bromo-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine | 202409-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-bromo-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine
• 英文别名: 2-Bromo-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)pyridine
• CAS: 202409-76-5
• 化学式: C₁₃H₉BrF₃NO₂S
• 分子量: 380.185
• InChiKey: CEZSIHHOYZNVQO-UHFFFAOYSA-N

物化性质

• 沸点：
  478.3±45.0 °C(Predicted)
• 密度：
  1.587±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-mercapto-2-methyl-2-hydroxy-propane 、 2-bromo-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-hydroxy-2-methyl-1-thiopropyloxy)-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine
  参考文献：
  名称：

  2-Heterosubstituted-3-(4-methylsulfonyl)phenyl-5-trifluoromethyl pyridines as selective and orally active cyclooxygenase-2 inhibitors

  摘要：

  A series of novel 2-alkoxy, 2-thioalkoxy and 2-amino-3-(4-methylsulfonyl)phenylpyridines has been synthesized and shown to be highly potent and selective cyclooxygenase-2 (COX-2) inhibitors. Structure-activity relationship studies have demonstrated that central pyridine ring substituents play an important role in the COX-2 potency, selectivity vs the COX-1 enzyme, and oral activity. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00264-4
• 作为产物：
  描述：

  2-氨基-3-溴-5-三氟甲基吡啶 在 四氧化锇 、 四(三苯基膦)钯 、 N-甲基吲哚酮 、 氢溴酸 、 溴 、 碳酸氢钠 、 sodium nitrite 作用下， 以 乙醇 、 水 、 丙酮 、 苯 为溶剂， 生成 2-bromo-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine
  参考文献：
  名称：

  2-Heterosubstituted-3-(4-methylsulfonyl)phenyl-5-trifluoromethyl pyridines as selective and orally active cyclooxygenase-2 inhibitors

  摘要：

  A series of novel 2-alkoxy, 2-thioalkoxy and 2-amino-3-(4-methylsulfonyl)phenylpyridines has been synthesized and shown to be highly potent and selective cyclooxygenase-2 (COX-2) inhibitors. Structure-activity relationship studies have demonstrated that central pyridine ring substituents play an important role in the COX-2 potency, selectivity vs the COX-1 enzyme, and oral activity. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00264-4

文献信息

• 2-aminopyridines as inhibitors of cyclooxygenase-2
  申请人：Merck Frosst Canada, Inc.

  公开号：US06004950A1

  公开（公告）日：1999-12-21

  The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  本发明包括式I的新化合物以及一种治疗环氧合酶-2介导疾病的方法，包括向需要此类治疗的病人施用非毒性且具有治疗有效量的式I化合物。##STR1## 本发明还涵盖了用于治疗环氧合酶-2介导疾病的某些药物组合物，包括式I的化合物。
• Substituted pyridines as selective cyclooxygenase-2 inhibitors
  申请人：Merck Frosst Canad, Inc.

  公开号：US05861419A1

  公开（公告）日：1999-01-19

  The invention encompasses the novel compound of Formula I as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of Formula I.

  该发明涵盖了式I的新化合物，以及一种治疗COX-2介导疾病的方法，包括向需要此类治疗的患者施用式I化合物的非毒性治疗有效量。该发明还涵盖了用于治疗COX-2介导疾病的某些药物组合，其中包括式I的化合物。
• [EN] SUBSTITUTED PYRIDINES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] PYRIDINES SUBSTITUEES EN TANT QU'INHIBITEURS SELECTIFS DE LA CYCLO-OXYGENASE-2
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1998003484A1

  公开（公告）日：1998-01-29

  (EN) The invention encompasses the novel compound of formula (I) as well as a method of treating COX-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of formula (I). The invention also encompasses certain pharmaceutical compositions for treatment of COX-2 mediated diseases comprising compounds of formula (I).(FR) L'invention concerne le nouveau composé de la formule (I) de même qu'un procédé de traitement des maladies induites par COX-2, lequel consiste à administrer à un patient nécessitant un tel traitement une dose non toxique et efficace sur le plan thérapeutique d'un composé de la formule (I). L'invention concerne également certaines compositions pharmaceutiques destinées au traitement de maladies induites par COX-2, et comprenant les composés de la formule (I).

  该发明涉及公式（I）的新型化合物，以及治疗COX-2介导的疾病的方法，包括向需要此类治疗的患者施用公式（I）化合物的非毒性治疗有效剂量。该发明还涵盖了用于治疗COX-2介导疾病的某些药物组合物，其中包括公式（I）的化合物。
• 2-Pyridinyl-3-(4-methylsulfonyl)phenylpyridines: Selective and orally active cyclooxygenase-2 inhibitors
  作者：Richard W Friesen、Christine Brideau、Chi Chung Chan、Stella Charleson、Denis Deschênes、Daniel Dubé、Diane Ethier、Réjean Fortin、Jacques Yves Gauthier、Yves Girard、Robert Gordon、Gillian M Greig、Denis Riendeau、Chantal Savoie、Zhaoyin Wang、Elizabeth Wong、Denise Visco、Li Jing Xu、Robert N Young

  DOI：10.1016/s0960-894x(98)00499-5

  日期：1998.10

  A series of novel 2-pyridinyl-3-(4-methylsulfonyl)phenylpyridines has been synthesized and evaluated with respect to their ability to inhibit the isozymes of cyclooxygenase, COX-I, and COX-2. Optimum COX-2 activity is observed by introduction of a substituent at C5 of the central pyridine. 5-Chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine 33 was identified as the optimum compound in this series. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• 2-AMINOPYRIDINES AS INHIBITORS OF CYCLOOXYGENASE-2
  申请人：MERCK FROSST CANADA & CO.

  公开号：EP1015431B1

  公开（公告）日：2005-04-20