(-)-3-(4-Methylsulfonyl)phenyl-2-(3-hydroxymethyl)piperidin-1-yl-5-trifluoromethylpyridine

• 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: (-)-3-(4-Methylsulfonyl)phenyl-2-(3-hydroxymethyl)piperidin-1-yl-5-trifluoromethylpyridine
• 英文别名: [1-[3-(4-Methylsulfonylphenyl)-5-(trifluoromethyl)pyridin-2-yl]piperidin-3-yl]methanol
• 化学式: C₁₉H₂₁F₃N₂O₃S
• 分子量: 414.449
• InChiKey: KVUASUDFPOEMLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氨基-3-溴-5-三氟甲基吡啶 在 盐酸 、 四氧化锇 、 四(三苯基膦)钯 、 N-甲基吲哚酮 、 碳酸氢钠 、 sodium nitrite 、 三氯氧磷 作用下， 以 乙醇 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 生成 (-)-3-(4-Methylsulfonyl)phenyl-2-(3-hydroxymethyl)piperidin-1-yl-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 & CO.

  公开号：EP1015431B1

  公开（公告）日：2005-04-20
• US6004950A
  申请人：——

  公开号：US6004950A

  公开（公告）日：1999-12-21
• [EN] 2-AMINOPYRIDINES AS INHIBITORS OF CYCLOOXYGENASE-2<br/>[FR] 2-AMINOPYRIDINES UTILISEES COMME INHIBITEURS DE LA CYCLO-OXYGENASE 2
  申请人：MERCK FROSST CANADA & CO.

  公开号：WO1999014195A1

  公开（公告）日：1999-03-25

  (EN) 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). The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula (I).(FR) L'invention concerne un nouveau composé de formule (I), ainsi qu'une méthode permettant de traiter les maladies ayant pour médiateur la cyclo-oxygénase 2, qui consiste à administrer à un patient ayant besoin dudit traitement une quantité, efficace sur le plan thérapeutique et non toxique, d'un composé de formule (I). L'invention concerne également certaines compositions pharmaceutiques destinées au traitement des maladies ayant pour médiateur la cyclo-oxygénase 2 et renfermant des composés de formule (I).
• 2-Heterosubstituted-3-(4-methylsulfonyl)phenyl-5-trifluoromethyl pyridines as selective and orally active cyclooxygenase-2 inhibitors
  作者：Daniel Dubé、Christine Brideau、Denis Deschênes、Réjean Fortin、Richard W. Friesen、Robert Gordon、Yves Girard、Denis Riendeau、Chantal Savoie、Chi-Chung Chan

  DOI：10.1016/s0960-894x(99)00264-4

  日期：1999.6

  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.