(R)-1-(5,6-dichloropyridin-3-yl)ethane-1,2-diol | 1073617-84-1

• 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: (R)-1-(5,6-dichloropyridin-3-yl)ethane-1,2-diol
• 英文别名: (1R)-1-(5,6-dichloropyridin-3-yl)ethane-1,2-diol
• CAS: 1073617-84-1
• 化学式: C₇H₇Cl₂NO₂
• 分子量: 208.044
• InChiKey: NGIAOOMOOSRHSK-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  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)-4-[3-chloro-5-(1,2-dihydroxyethyl)pyridin-2-yl]-N-[5-(trifluoromethyl)pyridin-2-yl]-3,6-dihydropyridine-1(2H)-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
• 作为产物：
  描述：

  1-(5,6-dichloropyridin-3-yl)ethan-1-ol 在 AD-mix-β 、 potassium osmate 、 potassium carbonate 、 对甲苯磺酸 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 氯苯 、 叔丁醇 为溶剂， 反应 24.5h， 生成 (R)-1-(5,6-dichloropyridin-3-yl)ethane-1,2-diol
  参考文献：
  名称：

  WO2008/132600

  摘要：

  公开号：

文献信息

• MONOCYCLIC COMPOUNDS AND THEIR USE AS TRPV1 LIGANDS
  申请人：Tafesse Laykea

  公开号：US20100120862A1

  公开（公告）日：2010-05-13

  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.

  本发明涉及公式I的化合物及其药学上可接受的衍生物，包括含有公式I化合物或其药学上可接受的衍生物的有效量的组合物，以及治疗或预防疼痛、尿失禁、溃疡、炎症性肠病（IBD）和肠易激综合征（IBS）等疾病的方法，包括向需要的动物施用公式I化合物或其药学上可接受的衍生物的有效量。
• HETEROCYCLIC TRPV1 RECEPTOR LIGANDS
  申请人：Tafesse Laykea

  公开号：US20100137306A1

  公开（公告）日：2010-06-03

  The invention relates to compounds of formulae I(a)-I(d): and pharmaceutically acceptable derivatives thereof, compositions comprising an effective amount of a compound of formulae I(a)-I(d) 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 formulae I(a)-I(d) or a pharmaceutically acceptable derivative thereof.

  该发明涉及以下化合物的化学式：I(a)-I(d)，及其药学上可接受的衍生物，包括含有化合物I(a)-I(d)或其药学上可接受的衍生物的有效量的组合物，以及用于治疗或预防疼痛、尿失禁、溃疡、炎症性肠病和肠易激综合征等疾病的方法，包括向需要的动物施用化合物I(a)-I(d)或其药学上可接受的衍生物的有效量。
• BICYCLOHETEROARYL COMPOUNDS AND THEIR USE AS TRPV1 LIGANDS
  申请人：TAFESSE LAYKEA

  公开号：US20100130499A1

  公开（公告）日：2010-05-27

  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.

  该发明涉及公式I的化合物及其药用可接受的衍生物，包含有效量的公式I化合物或其药用可接受的衍生物的组合物，以及治疗或预防疼痛、尿失禁、溃疡、炎症性肠病和肠易激综合征等疾病的方法，包括向需要治疗的动物施用公式I化合物或其药用可接受的衍生物的有效量。
• 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：Purdue Pharma L.P.

  公开号：US10584110B2

  公开（公告）日：2020-03-10

  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.

  本发明涉及式 IA 的化合物 及其药学上可接受的衍生物，包含有效量的式 IA 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 IBS 等病症的方法，包括向需要的动物施用有效量的式 IA 化合物或其药学上可接受的衍生物。