3-(4-fluorophenyl)-1-methyl-5-(1-piperazinyl)-4-(4-pyridinyl)-1H-pyrrole-2-carboxylic acid methyl ester | 678161-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-fluorophenyl)-1-methyl-5-(1-piperazinyl)-4-(4-pyridinyl)-1H-pyrrole-2-carboxylic acid methyl ester
• 英文别名: methyl 3-(4-fluorophenyl)-1-methyl-5-piperazin-1-yl-4-pyridin-4-ylpyrrole-2-carboxylate
• CAS: 678161-35-8
• 化学式: C₂₂H₂₃FN₄O₂
• 分子量: 394.449
• InChiKey: BJPAAUARTYANJL-UHFFFAOYSA-N

物化性质

• 沸点：
  598.8±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-1-methyl-5-(1-piperazinyl)-4-(4-pyridinyl)-1H-pyrrole-2-carboxylic acid methyl ester 、 异氰酸乙酯 在 sodium;hydride 、 hexanes 、 水 、 乙酸乙酯 、 Sodium sulfate-III 作用下， 反应 4.5h， 以to give Compound 13 (83 mg) as an oil的产率得到5-[4-[(ethylamino)carbonyl]-1-piperazinyl]-3-(4-fluorophenyl)-1-methyl-4-(4-pyridinyl)-1H-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Substituted 3-(2,5-disubstituted)pyridyl-4-aryl pyrroles for treating inflammatory diseases

  摘要：

  本发明提供了新型取代的3-(2,5-二取代)吡啶基-4-芳基吡咯，以及包含它们的药物组合物，用于治疗通过在适当的细胞中减少TNF-α产生和/或p38活性而改善的疾病。 本发明还提供了使用这种药物组合物的治疗和预防方法。

  公开号：

  US20050043331A1
• 作为产物：
  描述：

  3-(4-氟苯基)-4-(4-吡啶基)-1H-吡咯-2-甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydride 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 生成 3-(4-fluorophenyl)-1-methyl-5-(1-piperazinyl)-4-(4-pyridinyl)-1H-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Inhibitors of unactivated p38 MAP kinase

  摘要：

  Inhibition of the p38 map kinase pathway has been shown to be beneficial in the treatment of inflammatory diseases. The first class of potent p38 kinase inhibitors was the pyridinylimidazole compounds from SKB. Since then several pyridinylimidazole-based compounds have been shown to inhibit activated p38 kinase in vitro and in vivo. We have developed a novel series of pyridinylimidazole-based compounds, which potently inhibit the p38 pathway by binding to unactivated p38 kinase and only weakly inhibiting activated p38 kinase activity in vitro.

  DOI：

  10.1016/j.bmcl.2006.08.101

文献信息

• [EN] 3,4-DISUBSTITUTED PYRROLES AND THEIR FOR USE IN TREATING INFLAMMATORY DISEASES<br/>[FR] PYRROLES 3,4-DISUBSTITUES ET UTILISATION DE CEUX-CI POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004029040A1

  公开（公告）日：2004-04-08

  This invention provides novel substituted 3-(2,5-disubstituted)pyridyl-4-aryl pyrroles, and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by reducing TNF-α production and/or p38 activity in appropriate cells. This invention also provides therapeutic and prophylactic methods using the instant pharmaceutical compositions.

  这项发明提供了新型的取代3-(2,5-二取代)吡啶基-4-芳基吡咯烷，并包括相同的药物组合物，用于治疗通过在适当细胞中减少TNF-α产生和/或p38活性而改善的疾病。该发明还提供了使用即时药物组合物的治疗和预防方法。
• 3,4-DISUBSTITUTED PYRROLES AND THEIR FOR USE IN TREATING INFLAMMATORY DISEASES
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1549635A1

  公开（公告）日：2005-07-06
• Inhibitors of unactivated p38 MAP kinase
  作者：James Bullington、Dennis Argentieri、Kristin Averill、Demetrius Carter、Druie Cavender、Bohumila Fahmy、Xiaodong Fan、Daniel Hall、Geoffrey Heintzelman、Paul Jackson、Wai-Ping Leung、Xun Li、Ping Ling、Gilbert Olini、Thomas Razler、Michael Reuman、Kenneth Rupert、Ronald Russell、John Siekierka、Scott Wadsworth、Russell Wolff、Bangping Xiang、Yue-Mei Zhang

  DOI：10.1016/j.bmcl.2006.08.101

  日期：2006.12

  Inhibition of the p38 map kinase pathway has been shown to be beneficial in the treatment of inflammatory diseases. The first class of potent p38 kinase inhibitors was the pyridinylimidazole compounds from SKB. Since then several pyridinylimidazole-based compounds have been shown to inhibit activated p38 kinase in vitro and in vivo. We have developed a novel series of pyridinylimidazole-based compounds, which potently inhibit the p38 pathway by binding to unactivated p38 kinase and only weakly inhibiting activated p38 kinase activity in vitro.
• Substituted 3-(2,5-disubstituted)pyridyl-4-aryl pyrroles for treating inflammatory diseases
  申请人：Bullington L. James

  公开号：US20050043331A1

  公开（公告）日：2005-02-24

  This invention provides novel substituted 3-(2,5-disubstituted)pyridyl-4-aryl pyrroles, and pharmaceutical compositions comprising same, useful for treating disorders ameliorated by reducing TNF-α production and/or p38 activity in appropriate cells. This invention also provides therapeutic and prophylactic methods using the instant pharmaceutical compositions.

  本发明提供了新型取代的3-(2,5-二取代)吡啶基-4-芳基吡咯，以及包含它们的药物组合物，用于治疗通过在适当的细胞中减少TNF-α产生和/或p38活性而改善的疾病。 本发明还提供了使用这种药物组合物的治疗和预防方法。