2-(2-carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfonyl}phenoxy)acetamide | 519183-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(2-carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfonyl}phenoxy)acetamide
• 英文别名: 2-(2-carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl)-benzimidazole-1-sulfonyl}-phenoxy)-acetamide；2-(2-Carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetamide；2-[2-(2-amino-2-oxoethoxy)-4-[2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]benzimidazol-1-yl]sulfonylphenoxy]acetamide
• CAS: 519183-12-1
• 化学式: C₂₆H₂₄F₃N₅O₈S₂
• 分子量: 655.632
• InChiKey: FMPLYTKSJCFWNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  223
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2-Carbamoylmethoxy-4-chlorosulfonylphenoxyacetamide 、 兰索拉唑 以78%的产率得到2-(2-carbamoylmethoxy-4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfonyl}phenoxy)acetamide
  参考文献：
  名称：

  1-Arylsulfonyl-2-(Pyridylmethylsulfinyl) Benzimidazoles as New Proton Pump Inhibitor Prodrugs

  摘要：

  我们合成了新的芳基磺酰基质子泵抑制剂（PPI）原药。这些原药能延长 PPI 有效血浆浓度的停留时间，从而提高胃酸抑制效果。

  DOI：

  10.3390/molecules14125247

文献信息

• Prodrugs of proton pump inhibitors
  申请人：Regents of the University of California

  公开号：US06559167B1

  公开（公告）日：2003-05-06

  Prodrugs of the pyridyl methyl sulfinyl benzimidazole type proton pump inhibitor drugs have a hydrolyzable arylsulfonyl or heteroarylsulfonyl group attached to the benzimidazole nitrogen. The prodrugs of the invention hydrolyze under physiological conditions to provide the proton pump inhibitors with a half life measurable in hours, and are capable of providing sustained plasma concentrations of the proton pump inhibitor drugs for longer time than presently used drugs. The generation of the proton pump inhibitor drugs from the prodrugs of the invention under physiological conditions allows for more effective treatment of several diseases and conditions caused by gastric acid secretion.

  该类型的吡啶甲基亚砜基苯并咪唑类质子泵抑制剂药物的前药，其将可水解的芳基磺酰基或杂环芳基磺酰基连接到咪唑类氮原子上。本发明的前药在生理条件下水解，提供半衰期可在小时内测量的质子泵抑制剂，并能够提供比目前使用的药物更长时间的持续血浆浓度。在生理条件下从本发明的前药生成质子泵抑制剂药物，可更有效地治疗由胃酸分泌引起的多种疾病和症状。
• Prodrugs of proton pump inhibitors including the (1h-pyrrol-1-yl)-1h-benzimidazole moiety
  申请人：Garst Michael E.

  公开号：US20100113524A1

  公开（公告）日：2010-05-06

  The compounds of the formulas (I), (II), (III) and (IV), where the symbols are as defined in the specification are prodrugs of proton pump inhibitors. The R 4 group includes at least one acidic group or its pharmaceutically acceptable salt, and the compound having the R 4 group have improved aqueous solubility, stability in plasma and improved bioavailability.

  公式(I)、(II)、(III)和(IV)的化合物，其中符号如规范中定义的那样，是质子泵抑制剂的前药。R4基团包括至少一个酸性基团或其药学上可接受的盐，具有R4基团的化合物具有改善的水溶性、血浆稳定性和改善的生物利用度。
• Prodrugs of proton pump inhibitors including the 1h-imidazo[4,5-b] pyridine moiety
  申请人：Garst Michael E.

  公开号：US20100317689A1

  公开（公告）日：2010-12-16

  The compounds of formulas (I), (II), (III) and (IV), where the symbols are as defined in the specification are prodrugs of proton pump inhibitors. The R 4 group includes at least one acidic group or its pharmaceutically acceptable salt, and the compound having the R 4 group have improved aqueous solubility, stability in plasma and improved bioavailability.

  式(I)、(II)、(III)和(IV)的化合物，其中符号如规范中所定义，是质子泵抑制剂的前药。R4基团包括至少一个酸性基团或其药学上可接受的盐，并且具有R4基团的化合物具有改善的水溶性、血浆稳定性和改善的生物利用度。
• US6559167B1
  申请人：——

  公开号：US6559167B1

  公开（公告）日：2003-05-06
• 1-Arylsulfonyl-2-(Pyridylmethylsulfinyl) Benzimidazoles as New Proton Pump Inhibitor Prodrugs
  作者：Jai Moo Shin、George Sachs、Young-moon Cho、Michael Garst

  DOI：10.3390/molecules14125247

  日期：——

  New arylsulfonyl proton pump inhibitor (PPI) prodrug forms were synthesized. These prodrugs provided longer residence time of an effective PPI plasma concentration, resulting in better gastric acid inhibition.

  我们合成了新的芳基磺酰基质子泵抑制剂（PPI）原药。这些原药能延长 PPI 有效血浆浓度的停留时间，从而提高胃酸抑制效果。