N-Cyclopropyl-1-{3-[6-(1-Hydroxy-1-Methylethyl)Pyridin-3-yl]Phenyl}-1,4-Dihydro[1,8]Naphthyridin-4-One-3-Carboxamide | 477252-30-5

• 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: N-Cyclopropyl-1-{3-[6-(1-Hydroxy-1-Methylethyl)Pyridin-3-yl]Phenyl}-1,4-Dihydro[1,8]Naphthyridin-4-One-3-Carboxamide
• 英文别名: N-cyclopropyl-1-(3-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)phenyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide；N-cyclopropyl-1-[3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]phenyl]-4-oxo-1,8-naphthyridine-3-carboxamide
• CAS: 477252-30-5
• 化学式: C₂₆H₂₄N₄O₃
• 分子量: 440.502
• InChiKey: VKEGWFZBNIKAFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-Cyclopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide 、 6-(2-羟基丙烷-2-基)吡啶-3-硼酸 在 反式双(三苯基膦)二氯溴钯(II) 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 N-Cyclopropyl-1-{3-[6-(1-Hydroxy-1-Methylethyl)Pyridin-3-yl]Phenyl}-1,4-Dihydro[1,8]Naphthyridin-4-One-3-Carboxamide
  参考文献：
  名称：

  Optimization and structure–activity relationship of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides: Identification of MK-0873, a potent and effective PDE4 inhibitor

  摘要：

  A SAR study of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides is described. Optimization of the series was based on in vitro potency against PDE4, inhibition of the LPS-induced production of TNF-alpha in human whole blood and minimizing affinity for the hERG potassium channel. From these studies, compounds 18 and 20 (MK-0873) were identified as optimized PDE4 inhibitors with good overall in vitro and in vivo profiles and selected as development candidates. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.009

文献信息

• 1-biaryl-1,8-naphthyridin-4-one phosphodiesterase-4 inhibitors
  申请人：——

  公开号：US20030096829A1

  公开（公告）日：2003-05-22

  Compounds represented by Formula (I): 1 or a pharmaceutically acceptable salt thereof, are phosphodiesterrase 4 inhibitors useful in the treatment of asthma and inflammation.

  由化学式（I）表示的化合物： 1 或其药用可接受的盐，是磷酸二酯酶4抑制剂，用于治疗哮喘和炎症。
• Method of preparing inhibitors of phosphodiesterase-4
  申请人：——

  公开号：US20040102472A1

  公开（公告）日：2004-05-27

  In one aspect, the present invention is directed to a one pot method of preparing intermediates of Formula V, which are useful in making inhibitors of phosphodiesterase-4: 1 The present invention is also directed to a method of preparing phosphodiesterase inhibitors comprising the Formula 2

  在一个方面，本发明涉及一种制备Formula V中间体的一锅法，该中间体在制备磷酸二酯酶-4抑制剂时非常有用： 另外，本发明还涉及一种制备磷酸二酯酶抑制剂的方法，包括Formula 2。
• Use of phosphodiesterase-4 inhibitors as enhancers of cognition
  申请人：Dube Daniel

  公开号：US20060040981A1

  公开（公告）日：2006-02-23

  The present invention is directed to a method of enhancing cognition in a healthy subject comprising administering a safe cognition enhancing amount of a phosphodiesterase-4 inhibitor. In particular, this invention is directed to a method of enhancing memory, learning, retention, recall, awareness and judgement in health subjects comprising administering a safe and effective amount of a phosphodiesterase-4 inhibitor.

  本发明涉及一种增强健康受试者认知能力的方法，包括给予安全的磷酸二酯酶-4抑制剂增强认知能力的剂量。特别地，本发明涉及一种增强健康受试者记忆、学习、保留、回忆、意识和判断力的方法，包括给予安全有效的磷酸二酯酶-4抑制剂的剂量。
• Method of preparing inhibitors phosphodiesterase-4
  申请人：Albaneze-Walker Jennifer

  公开号：US20060019981A1

  公开（公告）日：2006-01-26

  In one aspect, the present invention is directed to a one pot method of preparing intermediates of Formula (V), which are useful in making inhibitors of phosphodiesterase-4: The present invention is also directed to a method of preparing phosphodiesterase inhibitors comprising the Formula (IX, IXa)

  在某个方面，本发明涉及一种制备公式（V）中间体的一锅法，该中间体在制备磷酸二酯酶-4抑制剂时非常有用：本发明还涉及一种制备公式（IX，IXa）的磷酸二酯酶抑制剂的方法。
• 1-BIARYL-1,8-NAPTHYRIDIN-4-ONE PHOSPHODIESTERASE-4 INHIBITORS
  申请人：Merck Frosst Canada & Co.

  公开号：EP1397359B1

  公开（公告）日：2005-08-31