3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide

• 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: 3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide
• 英文别名: 3,6-dichloro-N-(4-methyl-1,3-thiazol-2-yl)pyridine-2-carboxamide
• 化学式: C₁₀H₇Cl₂N₃OS
• mdl: MFCD11147655
• 分子量: 288.157
• InChiKey: LIORGNQJERBBGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide 、 对氟苯硫酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以77%的产率得到6-chloro-3-((4-fluorophenyl)thio)-N-(4-methylthiazol-2-yl)picolinamide
  参考文献：
  名称：

  Discovery of novel 3,6-disubstituted 2-pyridinecarboxamide derivatives as GK activators

  摘要：

  A novel class of 3,6-disubstituted 2-pyridinecarboxamide derivatives was designed based on X-ray analysis of the 2-aminobenzamide lead class. Subsequent chemical modi. cation led to the discovery of potent GK activators which eliminate potential toxicity concerns associated with an aniline group of the lead structure. Compound 7 demonstrated glucose lowering effect in a rat OGTT model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.137
• 作为产物：
  描述：

  2-氨基-4-甲基噻唑 、 二氯吡啶酸 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 氯仿 为溶剂， 反应 24.0h， 以64%的产率得到3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide
  参考文献：
  名称：

  Discovery of novel 3,6-disubstituted 2-pyridinecarboxamide derivatives as GK activators

  摘要：

  A novel class of 3,6-disubstituted 2-pyridinecarboxamide derivatives was designed based on X-ray analysis of the 2-aminobenzamide lead class. Subsequent chemical modi. cation led to the discovery of potent GK activators which eliminate potential toxicity concerns associated with an aniline group of the lead structure. Compound 7 demonstrated glucose lowering effect in a rat OGTT model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.137

文献信息

• Novel 2-pyridinecarboxamide derivatives
  申请人：Mitsuya Morihiro

  公开号：US20060258701A1

  公开（公告）日：2006-11-16

  The present invention relates to a compound which has a glucokinase-activating effect and is useful as a therapeutic agent for diabetes mellitus, being represented by a formula (I): [wherein X 1 represents a nitrogen atom, sulfur atom, oxygen atom or the like; R 1 represents a 6- to 10-membered aryl group, 5- to 7-membered heteroaryl group or the like; D represents an oxygen atom or sulfur atom; R and R 3 are the same or different, each representing a hydrogen atom, lower alkyl group or the like; a formula (II) represents an optionally substituted 5- to 7-membered heteroaryl group or the like; a formula (III) represents a monocyclic or bicyclic heteroaryl group] or a pharmaceutically acceptable salt thereof.

  本发明涉及一种化合物，具有激活葡萄糖激酶的效果，并可用作糖尿病治疗剂，其化学式表示为（I）：[其中X1表示氮原子、硫原子、氧原子或类似物；R1表示6-至10-成员芳基基团、5-至7-成员杂芳基基团或类似物；D表示氧原子或硫原子；R和R3相同或不同，分别表示氢原子、低碳基或类似物；式（II）表示可选取代的5-至7-成员杂芳基团或类似物；式（III）表示单环或双环杂芳基团]或其药学上可接受的盐。
• 2-pyridinecarboxamide derivatives
  申请人：MSD K. K.

  公开号：US08344003B2

  公开（公告）日：2013-01-01

  The present invention relates to a compound which has a glucokinase-activating effect and is useful as a therapeutic agent for diabetes mellitus, being represented by a formula (I): [wherein X1 represents a nitrogen atom, sulfur atom, oxygen atom or the like; R1 represents a 6- to 10-membered aryl group, 5- to 7-membered heteroaryl group or the like; D represents an oxygen atom or sulfur atom; R2 and R3 are the same or different, each representing a hydrogen atom, lower alkyl group or the like; a formula (II) represents an optionally substituted 5- to 7-membered heteroaryl group or the like; a formula (III) represents a monocyclic or bicyclic heteroaryl group] or a pharmaceutically acceptable salt thereof.

  本发明涉及一种具有葡萄糖激酶激活作用的化合物，可用作糖尿病治疗剂，其化学式表示为（I）：[其中X1表示氮原子、硫原子、氧原子或类似物；R1表示6-至10-成员芳基基团、5-至7-成员杂芳基团或类似物；D表示氧原子或硫原子；R2和R3相同或不同，分别表示氢原子、较低的烷基基团或类似物；式（II）表示可选地取代的5-至7-成员杂芳基团或类似物；式（III）表示单环或双环杂芳基团]或其药学上可接受的盐。
• 2-pyridine carboxamide derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US07629362B2

  公开（公告）日：2009-12-08

  The present invention relates to a compound which has a glucokinase-activating effect and is useful as a therapeutic agent for diabetes mellitus, being represented by a formula (I): [wherein X1 represents a nitrogen atom, sulfur atom, oxygen atom or the like; R1 represents a 6- to 10-membered aryl group, 5- to 7-membered heteroaryl group or the like; D represents an oxygen atom or sulfur atom; R2 and R3 are the same or different, each representing a hydrogen atom, lower alkyl group or the like; a formula (II) represents an optionally substituted 5- to 7-membered heteroaryl group or the like; a formula (III) represents a monocyclic or bicyclic heteroaryl group] or a pharmaceutically acceptable salt thereof.

  本发明涉及一种具有葡萄糖激酶激活作用的化合物，可用作糖尿病治疗剂，其化学式为（I）：[其中X1表示氮原子、硫原子、氧原子或类似物；R1表示6-至10-成员的芳基基团、5-至7-成员的杂环芳基基团或类似物；D表示氧原子或硫原子；R2和R3相同或不同，分别表示氢原子、低碳基基团或类似物；化学式（II）表示可选取代的5-至7-成员的杂环芳基基团或类似物；化学式（III）表示单环或双环杂环芳基基团] 或其药学上可接受的盐。
• NOVEL 2-PYRIDINECARBOXAMIDE DERIVATIVES
  申请人：MSD K.K.

  公开号：EP1598349B1

  公开（公告）日：2011-07-27
• US7629362B2
  申请人：——

  公开号：US7629362B2

  公开（公告）日：2009-12-08