1-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid | 850040-14-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid
• 英文别名: 1-(1,3-thiazol-2-yl)-3,6-dihydro-2H-pyridine-4-carboxylic acid
• CAS: 850040-14-1
• 化学式: C₉H₁₀N₂O₂S
• 分子量: 210.257
• InChiKey: KNAOITOPNYRRSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid 、 4-三氟甲基磺酰苯胺 在 草酰氯 、 N,N-二甲基甲酰胺 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid (4-trifluoromethanesulfonyl-phenyl)-amide
  参考文献：
  名称：

  Tetrahydropyridine-4-carboxamides as novel, potent transient receptor potential vanilloid 1 (TRPV1) antagonists

  摘要：

  A series of 1,2,3,6-tetrahydropyridyl-4-carboxamides, exemplified by 6, have been synthesized and evaluated for in vitro TRPV1 antagonist activity, and in vivo analgesic activity in animal pain models. The tetrahydropyridine 6 is a novel TRPV1 receptor antagonist that potently inhibits receptor-mediated Ca2+ influx in vitro induced by several agonists, including capsaicin, N-arachidonoyldopamine (NADA), and low pH. This compound penetrates the CNS and shows potent anti-nociceptive effects in a broad range of animal pain models upon oral dosing due in part to its ability to antagonize both central and peripheral TRPV1 receptors. The SAR leading to the discovery of 6 is presented in this report. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.005
• 作为产物：
  描述：

  methyl 1-(thiazol-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 1-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid
  参考文献：
  名称：

  Tetrahydropyridine-4-carboxamides as novel, potent transient receptor potential vanilloid 1 (TRPV1) antagonists

  摘要：

  A series of 1,2,3,6-tetrahydropyridyl-4-carboxamides, exemplified by 6, have been synthesized and evaluated for in vitro TRPV1 antagonist activity, and in vivo analgesic activity in animal pain models. The tetrahydropyridine 6 is a novel TRPV1 receptor antagonist that potently inhibits receptor-mediated Ca2+ influx in vitro induced by several agonists, including capsaicin, N-arachidonoyldopamine (NADA), and low pH. This compound penetrates the CNS and shows potent anti-nociceptive effects in a broad range of animal pain models upon oral dosing due in part to its ability to antagonize both central and peripheral TRPV1 receptors. The SAR leading to the discovery of 6 is presented in this report. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.005

文献信息

• Novel amides useful for treating pain
  申请人：Zheng Zhu Guo

  公开号：US20050080095A1

  公开（公告）日：2005-04-14

  The present invention relates to compounds of formula (I-VII) or a pharmaceutically acceptable salt or prodrug thereof, in which A, L, R 6 , R 7 and R 8 are defined herein. The present invention also relates to methods of trating pain using these compounds and pharmaceutical compositions including these compounds.

  本发明涉及式(I-VII)的化合物或其药用可接受的盐或前药，其中A、L、R6、R7和R8在此有所定义。本发明还涉及使用这些化合物治疗疼痛的方法以及包含这些化合物的药物组合物。
• [EN] P38 KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA KINASE P38
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005073232A1

  公开（公告）日：2005-08-11

  Compounds of Formula: (I) are inhibitors of p38 kinase and are useful in the treatment of conditions or disease states mediated by p38 kinase activity or mediated by cytokines produced by the activity of p38.

  公式为（I）的化合物是p38激酶的抑制剂，可用于治疗由p38激酶活性介导或由p38活性产生的细胞因子介导的疾病或疾病状态。
• Amides useful for treating pain
  申请人：Abbott Laboratories

  公开号：US07129235B2

  公开（公告）日：2006-10-31

  The present invention relates to compounds of formula (I-VII) or a pharmaceutically acceptable salt or prodrug thereof, in which A, L, R6, R7 and R8 are defined herein. The present invention also relates to methods of trating pain using these compounds and pharmaceutical compositions including these compounds.

  本发明涉及式(I-VII)化合物或其药学上可接受的盐或前药，其中A、L、R6、R7和R8在此定义。本发明还涉及使用这些化合物治疗疼痛的方法和包括这些化合物的制药组合物。
• NOVEL AMIDES USEFUL FOR TREATING PAIN
  申请人：LEE CHIH-HUNG

  公开号：US20080153809A1

  公开（公告）日：2008-06-26

  The present invention relates to compounds of formula (I-VII) or a pharmaceutically acceptable salt or prodrug thereof, in which A, L, R 6 , R 7 and R 8 are defined herein. The present invention also relates to methods of treating pain using these compounds and pharmaceutical compositions including these compounds.

  本发明涉及公式（I-VII）化合物或其药学上可接受的盐或前药，其中A、L、R6、R7和R8在此被定义。本发明还涉及使用这些化合物治疗疼痛的方法和包括这些化合物的制药组合物。
• 疼痛治療に有用な新規なアザ複素環アミド類
  申请人：アボット・ラボラトリーズ

  公开号：JP2007523865A

  公开（公告）日：2007-08-23

  本発明は、式（Ｉ〜ＶＩＩ）（Ｉ）の化合物またはその化合物の製薬上許容される塩もしくはプロドラッグに関するものであり、式中においてＡ、Ｌ、Ｒ６、Ｒ７およびＲ８は本明細書で定義の通りである。本発明はまた、それら化合物およびそれら化合物を含む医薬組成物を用いる疼痛の治療方法に関するものでもある。

  本发明涉及式（I-VII）(I)化合物或这些化合物的药学上可接受的盐或原药，其中A、L、R6、R7和R8如本文所定义。本发明还涉及使用这些化合物和含有这些化合物的药物组合物治疗疼痛的方法。