6-diethylamino-5-methylnicotinic acid hydrochloride | 1186617-35-5

• 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: 6-diethylamino-5-methylnicotinic acid hydrochloride
• 英文别名: 6-Diethylamino-5-methyl-nicotinic acid hydrochloride；6-(diethylamino)-5-methylpyridine-3-carboxylic acid;hydrochloride
• CAS: 1186617-35-5
• 化学式: C₁₁H₁₆N₂O₂*ClH
• 分子量: 244.721
• InChiKey: LTNBITHBSCYLBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  53.43
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide 、 6-diethylamino-5-methylnicotinic acid hydrochloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.08h， 生成
  参考文献：
  名称：

  [EN] PYRIDINE COMPOUNDS
  [FR] COMPOSÉS DE PYRIDINE

  摘要：

  这项发明涉及吡啶化合物，它们的制备以及它们作为药用活性化合物的用途。这些化合物特别作为免疫调节剂。

  公开号：

  WO2009109906A1
• 作为产物：
  描述：

  2-甲基-2-丁烯腈 在 盐酸 、 甲酸 、 硫酸 、 双氧水 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 600.0h， 生成 6-diethylamino-5-methylnicotinic acid hydrochloride
  参考文献：
  名称：

  Novel S1P₁ Receptor Agonists − Part 3: From Thiophenes to Pyridines

  摘要：

  In preceding communications we summarized our medicinal chemistry efforts leading to the identification of potent, selective, and orally active S1P(1) agonists such as the thiophene derivative 1. As a continuation of these efforts, we replaced the thiophene in 1 by a 2-, 3-, or 4-pyridine and obtained less lipophilic, potent, and selective S1P(1) agonists (e.g., 2) efficiently reducing blood lymphocyte count in the rat. Structural features influencing the compounds' receptor affinity profile and pharmacokinetics are discussed. In addition, the ability to penetrate brain tissue has been studied for several compounds. As a typical example for these pyridine based S1P(1) agonists, compound 53 showed EC50 values of 0.6 and 352 nM for the S1P(1), and S1P(3) receptor, respectively, displayed favorable PK properties, and penetrated well into brain tissue. In the rat, compound 53 maximally reduced the blood lymphocyte count for at least 24 h after oral dosing of 3 mg/kg.

  DOI：

  10.1021/jm4014696

文献信息

• PYRIDINE COMPOUNDS
  申请人：Bolli Martin

  公开号：US20110028448A1

  公开（公告）日：2011-02-03

  The invention relates to pyridine compounds, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.

  该发明涉及吡啶化合物，其制备和用作药物活性化合物。这些化合物特别作为免疫调节剂。
• [EN] PYRIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE PYRIDINE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2009109906A1

  公开（公告）日：2009-09-11

  The invention relates to pyridine compounds, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.

  这项发明涉及吡啶化合物，它们的制备以及它们作为药用活性化合物的用途。这些化合物特别作为免疫调节剂。
• Novel S1P₁ Receptor Agonists − Part 3: From Thiophenes to Pyridines
  作者：Martin H. Bolli、Stefan Abele、Magdalena Birker、Roberto Bravo、Daniel Bur、Ruben de Kanter、Christopher Kohl、Julien Grimont、Patrick Hess、Cyrille Lescop、Boris Mathys、Claus Müller、Oliver Nayler、Markus Rey、Michael Scherz、Gunther Schmidt、Jürgen Seifert、Beat Steiner、Jörg Velker、Thomas Weller

  DOI：10.1021/jm4014696

  日期：2014.1.9

  In preceding communications we summarized our medicinal chemistry efforts leading to the identification of potent, selective, and orally active S1P(1) agonists such as the thiophene derivative 1. As a continuation of these efforts, we replaced the thiophene in 1 by a 2-, 3-, or 4-pyridine and obtained less lipophilic, potent, and selective S1P(1) agonists (e.g., 2) efficiently reducing blood lymphocyte count in the rat. Structural features influencing the compounds' receptor affinity profile and pharmacokinetics are discussed. In addition, the ability to penetrate brain tissue has been studied for several compounds. As a typical example for these pyridine based S1P(1) agonists, compound 53 showed EC50 values of 0.6 and 352 nM for the S1P(1), and S1P(3) receptor, respectively, displayed favorable PK properties, and penetrated well into brain tissue. In the rat, compound 53 maximally reduced the blood lymphocyte count for at least 24 h after oral dosing of 3 mg/kg.