6-ethoxy-4-oxo-1,4-dihydro[1,5]naphthyridine-3-carboxylic acid benzylamide | 807326-59-6

• 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: 6-ethoxy-4-oxo-1,4-dihydro[1,5]naphthyridine-3-carboxylic acid benzylamide
• 英文别名: CP-457920；N-benzyl-6-ethoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxyamide；N-benzyl-6-ethoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxamide；1,5-Naphthyridine-3-carboxamide, 6-ethoxy-1,4-dihydro-4-oxo-N-(phenylmethyl)-；N-benzyl-6-ethoxy-4-oxo-1H-1,5-naphthyridine-3-carboxamide
• CAS: 807326-59-6；220860-50-4
• 化学式: C₁₈H₁₇N₃O₃
• 分子量: 323.351
• InChiKey: DGFVZQGXKQCQGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-ethoxy-4-oxo-1,4-dihydro[1,5]naphthyridine-3-carboxylic acid benzylamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-benzyl-6-ethoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxyamide potassium salt
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION AND PURIFICATION OF 1,5-NAPHTHYRIDINE-3-CARBOXYAMIDES
  [FR] PROCEDE DE PREPARATION ET DE PURIFICATION DE 1,5-NAPHTYRIDINE-3-CARBOXYAMIDES

  摘要：

  提供了一种新的制备和纯化取代的1,5-萘啶-3-羧酰胺的方法，这些化合物在焦虑、唐氏综合症、睡眠、认知和癫痫障碍以及苯二氮平类药物过量和警觉性增强方面有用。这些化合物可以通过用一级胺和1,1-羰基二咪唑处理相应的1,5-萘啶-3-羧酸制备而成。通过将取代的1,5-萘啶-3-羧酰胺转化为强碱盐（如叔丁基钾），再通过重结晶和酸化来得到纯的羧酰胺。

  公开号：

  WO2004106336A1
• 作为产物：
  描述：

  N-benzyl-6-ethoxy-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxyamide potassium salt 在 盐酸 、 水 作用下， 反应 4.0h， 以42%的产率得到6-ethoxy-4-oxo-1,4-dihydro[1,5]naphthyridine-3-carboxylic acid benzylamide
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION AND PURIFICATION OF 1,5-NAPHTHYRIDINE-3-CARBOXYAMIDES
  [FR] PROCEDE DE PREPARATION ET DE PURIFICATION DE 1,5-NAPHTYRIDINE-3-CARBOXYAMIDES

  摘要：

  提供了一种新的制备和纯化取代的1,5-萘啶-3-羧酰胺的方法，这些化合物在焦虑、唐氏综合症、睡眠、认知和癫痫障碍以及苯二氮平类药物过量和警觉性增强方面有用。这些化合物可以通过用一级胺和1,1-羰基二咪唑处理相应的1,5-萘啶-3-羧酸制备而成。通过将取代的1,5-萘啶-3-羧酰胺转化为强碱盐（如叔丁基钾），再通过重结晶和酸化来得到纯的羧酰胺。

  公开号：

  WO2004106336A1

文献信息

• Process for the preparation and purification of 1,5-naphthyridine-3-carboxyamides and purification of 1,5-naphthyridine-3-carboxyamides
  申请人：Castaldi J. Michael

  公开号：US20050004364A1

  公开（公告）日：2005-01-06

  A new route for the preparation and purification of substituted 1,5-naphthyridine-3-carboxyamides, useful in the diagnosis and treatment of anxiety, Downs Syndrome, sleep, cognitive and seizure disorders, and overdose with benzodiazepine drugs and for enhancement of alertness, is provided. These compounds may be readily prepared by treating the corresponding 1,5-naphthyridine-3-carboxylic acids with a primary amine and a 1,1-carbonyldiimidazole. Purification is achieved by converting the substituted 1,5-naphthyridine-3-carboxyamides to a salt with a strong base such as potassium t-butoxide, recrystallizing and acidifying to regenerate the pure carboxyamide.

  提供了一种新的制备和纯化取代的1,5-萘啉-3-羧酰胺的途径，这些化合物在焦虑、唐氏综合症、睡眠、认知和癫痫障碍以及苯二氮平药物过量和警觉性增强方面有用。这些化合物可以通过用一级胺和1,1-羰基二咪唑处理相应的1,5-萘啉-3-羧酸来轻松制备。通过将取代的1,5-萘啉-3-羧酰胺转化为强碱性盐（如叔丁基钾），重结晶和酸化来实现纯化，再生纯的羧酰胺。
• Process for the preparation of 1,5-naphthyridine-3-carboxyamides by direct ester amidation
  申请人：Karrick L. Gregory

  公开号：US20050038065A1

  公开（公告）日：2005-02-17

  A new route for the preparation of substituted 1,5-naphthyridine-3-carboxyamides, useful in the diagnosis and treatment of anxiety, Downs Syndrome, sleep, cognitive and seizure disorders, and overdose with benzodiazepine drugs and for enhancement of alertness, is provided. These compounds may be readily prepared by heating the corresponding 1,5-naphthyridine-3-carboxylic acid ester with a primary amine in a polar solvent such as dimethylformamide or dimethylsulfoxide.

  提供了一种制备取代的1,5-萘啶-3-羧酰胺的新途径，该化合物在焦虑、唐氏综合症、睡眠、认知和癫痫障碍、苯二氮平类药物过量和提高警觉性方面有用。这些化合物可以通过在极性溶剂如二甲基甲酰胺或二甲基亚砜中加热相应的1,5-萘啶-3-羧酸酯和一级胺来轻松制备。
• Use of negative modulators of GABA receptors containing alpha5 subunits as fast acting antidepressants
  申请人：University of Maryland, Baltimore

  公开号：US11083732B2

  公开（公告）日：2021-08-10

  Embodiments of the disclosure include methods and compositions related to treatment of one or more medical conditions with one or more negative modulators of GABAA receptors. In specific embodiments, depression and/or suicidability is treated or ameliorated or prevented with one or more negative modulators of GABAA receptors, such as a partial inverse agonist of a GABAA receptor comprising an alpha5 subunit.

  本公开的实施方案包括与用一种或多种 GABAA 受体负调节剂治疗一种或多种病症有关的方法和组合物。在具体的实施方案中，用一种或多种 GABAA 受体的负性调节剂，如包含α5 亚基的 GABAA 受体的部分反向激动剂，来治疗或改善或预防抑郁症和/或自杀倾向。
• Synthesis and Purification of 6-Ethoxy-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic Acid Benzylamide
  作者：Justin Beaudin、Dennis E. Bourassa、Paul Bowles、Michael J. Castaldi、Ronald Clay、Michel A. Couturier、Gregory Karrick、Teresa W. Makowski、Ruth E. McDermott、Clifford N. Meltz、Morgan Meltz、James E. Phillips、John A. Ragan、David H. Brown Ripin、Robert A. Singer、John L. Tucker、Lulin Wei

  DOI：10.1021/op0341061

  日期：2003.11.1

  The synthesis of 6-ethoxy-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid benzylamide (1) on multikilogram scale is described. The major challenge for the synthesis of this quinolone GABA partial agonist was in the isolation of product of acceptable purity for clinical studies due to the insolubility of this compound. Also described are efforts to circumvent a high-temperature cyclization required for the synthesis of the quinolone ring system.
• [EN] NOVEL GAMMA AMINOBUTYRIC ACID TYPE A RECEPTOR MODULATORS FOR MOOD DISORDERS<br/>[FR] NOUVEAUX MODULATEURS DU RÉCEPTEUR DE L'ACIDE GAMMA-AMINOBUTYRIQUE DE TYPE A DESTINÉS AUX TROUBLES DE L'HUMEUR
  申请人：UNIV MARYLAND

  公开号：WO2019046300A9

  公开（公告）日：2020-10-15