4-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester | 524734-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester
• 英文别名: ethyl 4-[8-(3-methylsulfanylphenyl)-1,7-naphthyridin-6-yl]cyclohexane-1-carboxylate
• CAS: 524734-51-8
• 化学式: C₂₄H₂₆N₂O₂S
• 分子量: 406.549
• InChiKey: LQKKLCBNEOFVQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-(8-(3-(methylthio)phenyl)-1,7-naphthyridin-6-yl)cyclohexanecarboxylic acid
  参考文献：
  名称：

  Solubility-Driven Optimization of Phosphodiesterase-4 Inhibitors Leading to a Clinical Candidate

  摘要：

  The solubility-driven optimization of a series of 1,7-napthyridine phosphodiesterase-4 inhibitors is described. Directed structural changes resulted in increased aqueous solubility, enabling superior pharmacokinetic properties with retention of PDE4 inhibition. A range of potent and orally bioavailable compounds with good in vivo efficacy in animal models of inflammation and reduced emetic potential compared to previously described drugs were synthesized. Compound 2d was taken forward as a clinical candidate for the treatment of COPD.

  DOI：

  10.1021/jm300459a
• 作为产物：
  描述：

  3-吡啶乙腈 在 三甲基氯硅烷 、 氢溴酸 、 双氧水 、 溶剂黄146 、 1,2-二溴乙烷 、 二甲氨基甲酰氯 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 4-[8-(3-Methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Solubility-Driven Optimization of Phosphodiesterase-4 Inhibitors Leading to a Clinical Candidate

  摘要：

  The solubility-driven optimization of a series of 1,7-napthyridine phosphodiesterase-4 inhibitors is described. Directed structural changes resulted in increased aqueous solubility, enabling superior pharmacokinetic properties with retention of PDE4 inhibition. A range of potent and orally bioavailable compounds with good in vivo efficacy in animal models of inflammation and reduced emetic potential compared to previously described drugs were synthesized. Compound 2d was taken forward as a clinical candidate for the treatment of COPD.

  DOI：

  10.1021/jm300459a

文献信息

• Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (pde4) inhibitors
  申请人：——

  公开号：US20040254212A1

  公开（公告）日：2004-12-16

  The invention relates to compounds of formula I 1 in free or salt form, where R 1 is a monovalent aromatic group having up to 10 carbon atoms, and R 2 is a cycloaliphatic group having up to 8 ring carbon atoms. Compositions containing them, methods for their preparation and their use as pharmaceuticals are also described.

  该发明涉及公式I1的化合物，以自由或盐形式存在，其中R1是具有最多10个碳原子的单价芳香基团，而R2是具有最多8个环碳原子的环烷基团。还描述了包含它们的组合物，它们的制备方法以及它们作为药物的用途。
• Polyaminopyridines and method for producing same
  申请人：Kanbara Takaki

  公开号：US20060293503A1

  公开（公告）日：2006-12-28

  The present invention provides novel polyaminopyridines which are excellent in solubility in various solvents, and are preferably used in a polymer-type organic electroluminescent material, and a process for preparing the same. More particularly, the present invention provides polyaminopyridines having a repetition structural unit represented by the following general formula (1); and having a number average molecular weight in a range of 500 to 1000000.

  本发明提供了新型的聚氨基吡啶，其在各种溶剂中具有优异的溶解性，并且最好用于聚合物型有机电致发光材料，并提供了制备它们的过程。更具体地，本发明提供了具有以下一般式（1）所表示的重复结构单元的聚氨基吡啶，其具有500至1000000之间的数均分子量。
• Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (PDE4) inhibitors
  申请人：Novartis AG

  公开号：US07273875B2

  公开（公告）日：2007-09-25

  The invention relates to compounds of formula I in free or salt form, where R1 is a monovalent aromatic group having up to 10 carbon atoms, and R2 is a cycloaliphatic group having up to 8 ring carbon atoms. Compositions containing them, methods for their preparation and their use as pharmaceuticals are also described.

  本发明涉及公式I的化合物，其以自由或盐形式存在，其中R1是具有最多10个碳原子的一价芳香基团，而R2是具有最多8个环状碳原子的环状脂肪族基团。还描述了含有它们的组合物，它们的制备方法以及它们作为药物的用途。
• POLYAMINOPYRIDINES AND METHOD FOR PRODUCING SAME
  申请人：SUMITOMO SEIKA CHEMICALS CO., LTD.

  公开号：EP1669390A1

  公开（公告）日：2006-06-14

  The present invention provides novel polyaminopyridines which are excellent in solubility in various solvents, and are preferably used in a polymer-type organic electroluminescent material, and a process for preparing the same. More particularly, the present invention provides polyaminopyridines having a repetition structural unit represented by the following general formula (1); and having a number average molecular weight in a range of 500 to 1000000.

  本发明提供了在各种溶剂中溶解性极佳的新型聚氨基吡啶，优选用于聚合物型有机电致发光材料，并提供了制备该材料的工艺。更具体地说，本发明提供了具有以下通式（1）所代表的重复结构单元的聚氨基吡啶； 且平均分子量在 500 至 1000000 之间。
• NAPHTHYRIDINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS PHOSPHODIESTERASE ISOENZYME 4 (PDE4) INHIBITORS
  申请人：Novartis AG

  公开号：EP1443925B1

  公开（公告）日：2006-12-27