AWD 140-190 | 135548-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: AWD 140-190
• 英文别名: 3-Morpholino-4-(4-bromophenyl)-1H-pyrrole-2-carboxylic acid methyl ester；methyl 4-(4-bromophenyl)-3-morpholin-4-yl-1H-pyrrole-2-carboxylate
• CAS: 135548-66-2
• 化学式: C₁₆H₁₇BrN₂O₃
• 分子量: 365.227
• InChiKey: VIWMXLPFMKLOCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-2-(4-Bromo-phenyl)-1,3-di-morpholin-4-yl-propenethione 在 双氧水 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.25h， 生成 AWD 140-190
  参考文献：
  名称：

  Synthesis, Anticonvulsant Activity, and Structure−Activity Relationships of Sodium Channel Blocking 3-Aminopyrroles

  摘要：

  Starting from the corresponding acetophenone and glycine derivatives, a series of new 3-aminopyrroles was synthesized in few steps. Using this procedure with hydrazine and hydroxylamine instead of the glycinates provides access to S-aminopyrazoles and 5-amino-1,2-oxazoles. The various derivatives were tested for anticonvulsant activity in a variety of test models. Several compounds exhibit considerable activity with a remarkable lack of neurotoxicity. 4-(4-Bromophenyl)-3-morpholinopyrrole-2-carboxylic acid methyl ester, 3, proved to be the most active compound. It was protective in the maximal electroshock seizure (MES) test in rats with an oral ED50 of 2.5 mg/kg with no neurotoxicity noted at doses up to 500 mg/kg. Compound 3 blocks sodium channels in a frequency-dependent manner. The essential structural features which could be responsible for an interaction with an active site of the voltage-dependent sodium channel are established within a suggested pharmacophore model.

  DOI：

  10.1021/jm970327j

文献信息

• Methods of treating gastrointestinal tract disorders using sodium channel modulators
  申请人：Dynogen Pharmaceuticals, Inc.

  公开号：US20040213842A1

  公开（公告）日：2004-10-28

  The invention relates to methods of using sodium channel modulators, particularly TTX-R sodium channel modulators and/or activity dependent sodium channel modulators to treat gastrointestinal tract disorders, particularly inflammatory bowel disorders and irritable bowel syndrome.

  本发明涉及使用钠通道调节剂，特别是 TTX-R 钠通道调节剂和/或活性依赖性钠通道调节剂治疗胃肠道疾病，特别是炎症性肠病和肠易激综合征的方法。
• Methods of treating lower urinary tract disorders using sodium channell modulators
  申请人：Dynogen Pharmaceuticals, Inc.

  公开号：US20040209960A1

  公开（公告）日：2004-10-21

  The invention relates to methods of using sodium channel modulators, particularly TTX-R sodium channel modulators and/or activity dependent sodium channel modulators to treat painful and non-painful lower urinary tract disorders, particularly painful and non-painful overactive bladder with and/or without loss of urine.

  本发明涉及使用钠通道调节剂，特别是TTX-R钠通道调节剂和/或活性依赖性钠通道调节剂治疗疼痛性和非疼痛性下尿路疾病的方法，特别是疼痛性和非疼痛性膀胱过度活动症，伴有和/或不伴有遗尿。
• Methods of treating lower urinary tract disorders using losigamone
  申请人：Burgard C. Edward

  公开号：US20050107353A1

  公开（公告）日：2005-05-19

  The invention relates to methods of using sodium channel modulators, preferably Losigamone or a pharmaceutically acceptable salt, enantiomer, analog, ester, amide, prodrug, metabolite, or derivative thereof, to treat painful and non-painful lower urinary tract disorders, particularly painful and non-painful overactive bladder with and/or without loss of urine.

  本发明涉及使用钠通道调节剂的方法，优选洛西加蒙或其药学上可接受的盐、对映体、类似物、酯、酰胺、原药、代谢物或衍生物，用于治疗疼痛性和非疼痛性下尿路疾病，特别是疼痛性和非疼痛性膀胱过度活动症，伴有和/或不伴有遗尿。
• METHODS OF TREATING LOWER URINARY TRACT DISORDERS USING SODIUM CHANNEL MODULATORS
  申请人：Dynogen Pharmaceuticals Inc.

  公开号：EP1589959A2

  公开（公告）日：2005-11-02
• US7041704B2
  申请人：——

  公开号：US7041704B2

  公开（公告）日：2006-05-09