4-amino-6-(2,4-dichloro-phenyl)-2-(3-methoxy-phenyl)-pyrimidine-5-carbonitrile | 582306-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-amino-6-(2,4-dichloro-phenyl)-2-(3-methoxy-phenyl)-pyrimidine-5-carbonitrile
• 英文别名: 4-Amino-6-(2,4-dichlorophenyl)-2-(3-methoxyphenyl)pyrimidine-5-carbonitrile
• CAS: 582306-99-8
• 化学式: C₁₈H₁₂Cl₂N₄O
• 分子量: 371.225
• InChiKey: DDCJBKUJBMHBFT-UHFFFAOYSA-N

物化性质

• 沸点：
  499.9±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-6-(2,4-dichloro-phenyl)-2-(3-methoxy-phenyl)-pyrimidine-5-carbonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 5-Aminomethyl-6-(2,4-dichloro-phenyl)-2-(3-methoxy-phenyl)-pyrimidin-4-ylamine
  参考文献：
  名称：

  Aminomethylpyrimidines as novel DPP-IV inhibitors: A 105-fold activity increase by optimization of aromatic substituents

  摘要：

  The influence of aromatic substitution on a newly discovered class of inhibitors of dipeptidyl peptidase IV was investigated. A 10(5)-fold increase in potency was achieved by the optimization of aromatic substituents in a parallel chemistry program. The observed SAR could be explained by an X-ray structure of the protein-ligand complex.

  DOI：

  10.1016/j.bmcl.2004.01.019
• 作为产物：
  描述：

  2-[(2,4-二氯苯基)亚甲基]丙二腈 、 3-甲氧基苯甲酰胺 在 potassium carbonate 、 potassium permanganate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 6.0h， 生成 4-amino-6-(2,4-dichloro-phenyl)-2-(3-methoxy-phenyl)-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Aminomethylpyrimidines as novel DPP-IV inhibitors: A 105-fold activity increase by optimization of aromatic substituents

  摘要：

  The influence of aromatic substitution on a newly discovered class of inhibitors of dipeptidyl peptidase IV was investigated. A 10(5)-fold increase in potency was achieved by the optimization of aromatic substituents in a parallel chemistry program. The observed SAR could be explained by an X-ray structure of the protein-ligand complex.

  DOI：

  10.1016/j.bmcl.2004.01.019

文献信息

• Pyridine and pyrimidine derivatives
  申请人：——

  公开号：US20030216382A1

  公开（公告）日：2003-11-20

  The present invention provides compounds of formula (I) 1 wherein R 1 , R 2 , R 3 , R 4 and X are as defined in the specification, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with DPP IV, such as diabetes, particularly non-insulin dependent diabetes mellitus, and impaired glucose tolerance.

  本发明提供了化合物的公式（I）1，其中R1、R2、R3、R4和X如规范中所定义，以及其药用盐。这些化合物可用于治疗和/或预防与DPP IV相关的疾病，如糖尿病，特别是非胰岛素依赖型糖尿病和糖耐量受损。
• NOVEL PYRIDIN- AND PYRIMIDIN-DERIVATIVES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1476435A1

  公开（公告）日：2004-11-17
• US6867205B2
  申请人：——

  公开号：US6867205B2

  公开（公告）日：2005-03-15
• US7022718B2
  申请人：——

  公开号：US7022718B2

  公开（公告）日：2006-04-04
• [EN] NOVEL PYRIDIN- AND PYRIMIDIN-DERIVATIVES<br/>[FR] NOUVEAUX DERIVES DE PYRIDINE ET DE PYRIMIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003068757A1

  公开（公告）日：2003-08-21

  The present invention relates to compounds of formula (I), wherein R1, R2, R3, R4 and X are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with DPP IV, such as diabetes, particularly non-insulin dependent diabetes mellitus, and impaired glucose tolerance.