7-chloro-4-oxo-2-(pyrrolidinylcarbonyl)hydroquinoline-3-carboxylic acid | 179543-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-chloro-4-oxo-2-(pyrrolidinylcarbonyl)hydroquinoline-3-carboxylic acid
• 英文别名: 7-Chloro-4-oxo-2-(pyrrolidine-1-carbonyl)-1,4-dihydro-quinoline-3-carboxylic acid；7-chloro-4-oxo-2-(pyrrolidine-1-carbonyl)-1H-quinoline-3-carboxylic acid
• CAS: 179543-91-0；182887-52-1
• 化学式: C₁₅H₁₃ClN₂O₄
• 分子量: 320.732
• InChiKey: YQBLDAFNZGSMIH-UHFFFAOYSA-N

物化性质

• 沸点：
  575.1±50.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-chloro-4-oxo-2-(pyrrolidinylcarbonyl)hydroquinoline-3-carboxylic acid 在 1,1'-dioctadecyl-4,4'-bipyridinium dibromide sodium dithionate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 22.08h， 生成 tert-butyl N-[[7-chloro-4-oxo-2-(pyrrolidine-1-carbonyl)-1H-quinoline-3-carbonyl]-[[3-(dimethylcarbamoylamino)phenyl]methyl]amino]carbamate
  参考文献：
  名称：

  Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain

  摘要：

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.

  DOI：

  10.1021/jm060212s
• 作为产物：
  描述：

  7-氯-4-羟基喹啉-2,3-二羧酸二甲酯 在 氢氧化钾 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 19.0h， 生成 7-chloro-4-oxo-2-(pyrrolidinylcarbonyl)hydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain

  摘要：

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.

  DOI：

  10.1021/jm060212s

文献信息

• Compound and method for the treatment of pain
  申请人：——

  公开号：US20030149042A1

  公开（公告）日：2003-08-07

  A compound, 7-chloro-4-hydroxy-2-(2-chloro-4-methylphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione, pharmaceutically-acceptable salts thereof, a method for treating pain comprising administration of a pain-ameliorating effective amount of the compound and pharmaceutical compositions containing the compound are disclosed.

  本文披露了一种化合物，即7-氯-4-羟基-2-(2-氯-4-甲基苯基)-1,2,5,10-四氢吡啶并[4,5-b]喹啉-1,10-二酮，其药用可接受的盐，一种治疗疼痛的方法，包括给予该化合物的疼痛缓解有效量，并含有该化合物的药物组合物。
• 1, 2, 5, 10-tetrahydropyridazino[4,5-b]quinoline-1,10-diones and their use for the treatment of pain
  申请人：——

  公开号：US20040053929A1

  公开（公告）日：2004-03-18

  Compounds according to structural diagram (I) are disclosed, wherein R 1 , A, E and D are as defined in the specification. Also disclosed are pharmaceutical compositions comprising a pain-ameliorating effective amount of a compound in accord with structural diagram (I).

  本发明揭示了根据结构图(I)的化合物，其中R1、A、E和D如规范中所定义。还揭示了包含符合结构图(I)的化合物的缓解疼痛有效量的药物组合物。
• 7-Chloro-4-hydroxy-2-(2-pyridylethyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione and the use thereof for the treatment of pain
  申请人：——

  公开号：US20040053930A1

  公开（公告）日：2004-03-18

  A compound, 7-chloro-4-hydroxy-2-(2-pyridylethyl)-1,2,5,10-tetrahydropyridazino[4,5-b] quinoline-1,10-dione, its (−) enantiomer, its (+) enantiomer, pharmaceutically-acceptable salts thereof, a method for treating pain comprising administering a pain-ameliorating effective amount of the (−) enantiomer to an individual suffering from pain and pharmaceutical compositions containing the (−) enantiomer are disclosed.

  本发明涉及一种化合物，即7-氯-4-羟基-2-(2-吡啶基乙基)-1,2,5,10-四氢吡啶并[4,5-b]喹啉-1,10-二酮，其(−)对映体，其(+)对映体，其药学上可接受的盐，一种治疗疼痛的方法，包括向遭受疼痛的个体投与(−)对映体的止痛有效量，以及含有(−)对映体的制药组合物。
• [EN] 7-CHLORO-4-HYDROXY-2-(2-PYRIDYLETHYL)-1,2,5,10-TETRAHYDROPYRIDAZINO[4,5-B]QUINOLINE-1,10-DIONE AND THE USE THEREOF FOR THE TREATMENT OF PAIN<br/>[FR] 7-CHLORO-4-HYDROXY-2-(2-PYRIDYLETHYL)-1,2,5,10-TETRAHYDROPYRIDAZINO[4,5-B]QUINOLINE-1,10-DIONE ET SON UTILISATION POUR LE TRAITEMENT DE LA DOULEUR
  申请人：ASTRAZENECA AB

  公开号：WO2002026740A1

  公开（公告）日：2002-04-04

  A compound, 7-chloro-4-hydroxy-2-(2-pyridylethyl)-1,2,5,10-tetrahydropyridazino[4,5-b] quinoline-1,10-dione, its (-) enantiomer, its (+) enantiomer, pharmaceutically-acceptable salts thereof, a method for treating pain comprising administering a pain-ameliorating effective amount of the (-) enantiomer to an individual suffering from pain and pharmaceutical compositions containing the (-) enantiomer are disclosed.

  本发明公开了一种化合物，即7-氯-4-羟基-2-(2-吡啶乙基)-1,2,5,10-四氢吡啶并[4,5-b]喹啉-1,10-二酮，其(-)对映体，其(+)对映体，其药学上可接受的盐，以及一种治疗疼痛的方法，包括向正在经历疼痛的个体投与有效减轻疼痛的量的(-)对映体，以及含有(-)对映体的制药组合物。
• Methods and compositions for the treatment of pain
  申请人：——

  公开号：US20030181449A1

  公开（公告）日：2003-09-25

  A method for the treatment of pain is disclosed comprising administration of a pain-ameliorating effective amount of any compound according to structural diagram I; 1 wherein A, D and R 1 are as defined in the specification. Also disclosed are pharmaceutical compositions comprising a pain-ameliorating effective amount of a compound in accord with structural diagram I.

  本发明揭示了一种治疗疼痛的方法，包括给予结构图I中的任何化合物的疼痛减轻有效量，其中A、D和R1如规范所定义。此外，本发明还揭示了包括符合结构图I的化合物的疼痛减轻有效量的药物组合物。