2-异丁基-6-甲基异烟酸盐酸盐 | 1011263-94-7

• 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
• 中文名称: 2-异丁基-6-甲基异烟酸盐酸盐
• 英文名称: 2-isobutyl-6-methylisonicotinic acid hydrochloride
• 英文别名: 2-methyl-6-(2-methyl-propyl)-isonicotinic acid hydrochloride；2-methyl-6-(2-methylpropyl)isonicotinic acid hydrochloride；2-isobutyl-6-methyl-isonicotinic acid hydrochloride；2-methyl-6-(2-methylpropyl)pyridine-4-carboxylic acid;hydrochloride
• CAS: 1011263-94-7
• 化学式: C₁₁H₁₅NO₂*ClH
• 分子量: 229.707
• InChiKey: JPSUSJHSLFUWJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  50.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-异丁基-6-甲基异烟酸盐酸盐 在 氨 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 生成 (2S)-1-amino-3-[2-ethyl-6-methyl-4-[5-[2-methyl-6-(2-methylpropyl)pyridin-4-yl]-1,2,4-oxadiazol-3-yl]phenoxy]propan-2-ol
  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
• 作为产物：
  描述：

  ethyl 2-cyclobutyl-6-methylisonicotinate 在 盐酸 作用下， 以 水 为溶剂， 反应 20.0h， 以93%的产率得到2-异丁基-6-甲基异烟酸盐酸盐
  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 DERIVATIVES AS S1P1/EDG1 RECEPTOR MODULATORS
  申请人：Bolli Martin

  公开号：US20110212998A1

  公开（公告）日：2011-09-01

  The invention relates to novel pyridine derivatives of formula (D, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. Formula (I) wherein A represents and the other substituents are as defined in the claims.

  本发明涉及式（D）的新吡啶衍生物、它们的制备方法以及它们作为药物活性化合物的用途。所述化合物特别是作为免疫调节剂发挥作用。式（I）中，A代表，其他取代基如权利要求中所定义。
• [EN] PYRIDINE DERIVATIVES AS S1P1/EDG1 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE PYRIDINE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2009024905A1

  公开（公告）日：2009-02-26

  The invention relates to novel pyridine derivatives of formula (I), their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. Formula (I) wherein A represents and the other substituants are as defined in the claims.

  该发明涉及公式（I）的新型吡啶衍生物，其制备以及作为药用活性化合物的用途。所述化合物特别作为免疫调节剂。公式（I）中A代表，其他取代基如索引中定义。
• Pyridin-4-yl derivatives as immunomodulating agents
  申请人：Bolli Martin

  公开号：US20100063108A1

  公开（公告）日：2010-03-11

  The invention relates to pyridine derivatives of Formula (I) wherein A, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.

  该发明涉及公式（I）中的吡啶衍生物，其中A、R1、R2、R3、R4、R5和R6如描述中所述，它们的制备以及它们作为药用活性化合物的用途。所述化合物特别作为免疫调节剂。
• Pyridine derivatives as S1P1/EDG1 receptor modulators
  申请人：Bolli Martin

  公开号：US08598208B2

  公开（公告）日：2013-12-03

  The invention relates to novel pyridine derivatives of formula (D, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. Formula (I) wherein A represents and the other substituents are as defined in the claims.

  本发明涉及公式（D）的新型吡啶衍生物，其制备方法以及其作为药物活性化合物的用途。所述化合物特别作为免疫调节剂。公式（I）其中A代表，其他取代基如权利要求所定义。
• WO2008/29371
  申请人：——

  公开号：——

  公开（公告）日：——