(R)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide | 1073617-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide
• 英文别名: 4-[3-chloro-5-[(1R)-1,2-dihydroxyethyl]pyridin-2-yl]-N-[4-(trifluoromethyl)phenyl]-3,6-dihydro-2H-pyridine-1-carboxamide
• CAS: 1073617-14-7
• 化学式: C₂₀H₁₉ClF₃N₃O₃
• 分子量: 441.837
• InChiKey: UQXMGVCFIOZTBP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.7
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-1-(5,6-dichloropyridin-3-yl)ethane-1,2-diol 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (R)-3-chloro-5-(1,2-dihydroxyethyl)-N-[4-(trifluoromethyl)phenyl]-3',6'-dihydro-(2,4'-bipyridine)-1'(2'H)-carboxamide
  参考文献：
  名称：

  Structure–Activity Relationship Studies and Discovery of a Potent Transient Receptor Potential Vanilloid (TRPV1) Antagonist 4-[3-Chloro-5-[(1S)-1,2-dihydroxyethyl]-2-pyridyl]-N-[5-(trifluoromethyl)-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxamide (V116517) as a Clinical Candidate for Pain Management

  摘要：

  A series of novel tetrahydropyridinecarboxamide TRPV1 antagonists were prepared and evaluated in an effort to optimize properties of previously described lead compounds from piperazinecarboxamide series. The compounds were evaluated for their ability to block capsaicin and acid-induced calcium influx in CHO cells expressing human TRPV1. The most potent of these TRPV1 antagonists were further characterized in pharmacokinetic, efficacy, and body temperature studies. On the basis of its pharmacokinetic, in vivo efficacy, safety, and toxicological properties, compound 37 was selected for further evaluation in human clinical trials.

  DOI：

  10.1021/jm500818a

文献信息

• TRPV1 antagonists and uses thereof
  申请人：Purdue Pharma L.P.

  公开号：EP2604598A1

  公开（公告）日：2013-06-19

  The invention relates to compounds of formula I and pharmaceutically acceptable derivatives thereof, compositions comprising an effective amount of a compound of formula I or a pharmaceutically acceptable derivative thereof, and methods for treating or preventing a condition such as pain, UI, an ulcer, IBD and IBS, comprising administering to an animal in need thereof an effective amount of a compound of formula I or a pharmaceutically acceptable derivative thereof.

  本发明涉及式 I 的化合物 及其药学上可接受的衍生物，包含有效量的式 I 化合物或其药学上可接受的衍生物的组合物，以及治疗或预防疼痛、UI、溃疡、IBD 和肠易激综合征等病症的方法，包括向有需要的动物施用有效量的式 I 化合物或其药学上可接受的衍生物。
• TRPV1 ANTAGONISTS INCLUDING DIHYDROXY SUBSTITUENT AND USES THEREOF
  申请人：Tafesse Laykea

  公开号：US20090170868A1

  公开（公告）日：2009-07-02

  The invention relates to compounds of formula IA and pharmaceutically acceptable derivatives thereof, compositions comprising an effective amount of a compound of formula IA or a pharmaceutically acceptable derivative thereof, and methods for treating or preventing a condition such as pain, UI, an ulcer, IBD and IBS, comprising administering to an animal in need thereof an effective amount of a compound of formula IA or a pharmaceutically acceptable derivative thereof.
• TRPV1 ANTAGONISTS INCLUDING SULFONAMIDE SUBSTITUENT AND USES THEREOF
  申请人：Kurose Noriyuki

  公开号：US20090170867A1

  公开（公告）日：2009-07-02

  The invention relates to compounds of formula IA′ and pharmaceutically acceptable derivatives thereof, compositions comprising an effective amount of a compound of formula IA′ or a pharmaceutically acceptable derivative thereof, and methods for treating or preventing a condition such as pain, UI, an ulcer, IBD and IBS, comprising administering to an animal in need thereof an effective amount of a compound of formula IA′ or a pharmaceutically acceptable derivative thereof.
• TRPV1 ANTAGONISTS INCLUDING AMIDE SUBSTITUENT AND USES THEREOF
  申请人：Tafesse Laykea

  公开号：US20090176796A1

  公开（公告）日：2009-07-09

  The invention relates to compounds of formula IA″ and pharmaceutically acceptable derivatives thereof, compositions comprising an effective amount of a compound of formula IA″ or a pharmaceutically acceptable derivative thereof, and methods for treating or preventing a condition such as pain, UI, an ulcer, IBD and IBS, comprising administering to an animal in need thereof an effective amount of a compound of formula IA″ or a pharmaceutically acceptable derivative thereof.
• US8476277B2
  申请人：——

  公开号：US8476277B2

  公开（公告）日：2013-07-02