2-[[[3-甲基-1-氧代-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]-1H-苯并咪唑 | 213476-12-1

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-[[[3-甲基-1-氧代-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]-1H-苯并咪唑
• 中文别名: 2-[[[3-甲基-1-氧代-4-(2,2,2-三氟乙氧基)-2-吡啶]甲基]亚硫酰基]苯并咪唑；右旋兰索拉唑杂质A；右旋兰索拉唑
• 英文名称: lansoprazole N-oxide
• 英文别名: 2-[[3-methyl-1-oxido-4-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]methylsulfinyl]-1H-benzimidazole
• CAS: 213476-12-1
• 化学式: C₁₆H₁₄F₃N₃O₃S
• 分子量: 385.367
• InChiKey: OBGHBYDDJGHGNS-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165°C (dec.)
• 沸点：
  657.4±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  兰索拉唑硫醚N-氧化物 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以67%的产率得到2-[[[3-甲基-1-氧代-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]-1H-苯并咪唑
  参考文献：
  名称：

  Synthesis and Characterization of Metabolites and Potential Impurities of Lansoprazole, an Antiulcerative Drug

  摘要：

  Lansoprazole (Prevacid) is an antiulcerative drug used for the treatment of duodenal and gastric ulcers, reflux oesophagitis, and Zollinger-Ellison syndrome. During the bulk synthesis of lansoprazole, we have observed five impurities: lansoprazole N-oxide, lansoprazole sulfone N-oxide, lansoprazole sulfide, lansoprazole sulfone and N-aralkyl lansoprazole. The present work describes the synthesis and characterization of these impurities.

  DOI：

  10.1080/00397910802162934

文献信息

• Method for preparing 2- (2-pyridinylmethylsulfinyl) benzimidazoles
  申请人：Fan Chin-Tsai

  公开号：US20090005570A1

  公开（公告）日：2009-01-01

  The present invention provides a method for preparing an antiulcer agent, 2-(2-pyridinylmethylsulfinyl)benzimidazoles, such as Omeprazole, Lansoprazole, Pantoprazole and Rabeprazole, which includes oxidizing an intermediate having a linkage of methylthio group (—CH 2 S—) to methylsulfinyl (—CH 2 S(O)—) in the presence of an oxidation catalyst of an alkali metal salt of tungstate at a temperature of 10-50° C.

  本发明提供了一种制备抗溃疡剂2-(2-吡啶甲基磺酰基)苯并咪唑类化合物，例如奥美拉唑、兰索拉唑、泮托拉唑和雷贝拉唑的方法，其中包括在碱金属钨酸盐氧化催化剂的存在下，在10-50°C的温度下将具有甲硫基链（-CH2S-）的中间体氧化为甲基磺酰基链（-CH2S（O）-）。
• ORAL SOLID PREPARATION COMPOSITION COMPRISING PROTON PUMP INHIBITOR, ORAL SOLID PREPARATION COMPRISING SAME, AND PREPARATION METHOD THEREFOR
  申请人：LOTTE Fine Chemical Co., Ltd.

  公开号：EP3646855A2

  公开（公告）日：2020-05-06

  Provided are an oral solid preparation composition, including a proton pump inhibitor or a pharmaceutically acceptable salt thereof; and a binding liquid including a basic additive, wherein a content of the basic additive is 2 to 13 parts by weight based on 100 parts by weight of the proton pump inhibitor or a pharmaceutically acceptable salt thereof; an oral solid preparation including the same; and a method of preparing the same. According to the present disclosure, an oral solid preparation exhibiting a significant reduction in the production of related substances and excellent stability against moisture and low pH is provided.

  本发明提供了一种口服固体制剂组合物，包括质子泵抑制剂或其药学上可接受的盐；以及一种包括碱性添加剂的结合液，其中碱性添加剂的含量以100份重量的质子泵抑制剂或其药学上可接受的盐为基准，为2至13份重量；包括该组合物的口服固体制剂；以及制备该组合物的方法。根据本公开，提供了一种口服固体制剂，该制剂显著减少了相关物质的产生，并具有优异的防潮稳定性和低 pH 值稳定性。
• Efficient Synthesis of <i>N</i>‐Oxide Derivatives: Substituted 2‐(2‐(Pyridyl‐<i>N</i>‐oxide)methylsulphinyl)benzimidazoles
  作者：Purna C. Ray、Vasantha Mittapelli、Amit Rohatgi、Om Dutt Tyagi

  DOI：10.1080/00397910701470693

  日期：2007.8.1
• US7531666B2
  申请人：——

  公开号：US7531666B2

  公开（公告）日：2009-05-12
• [EN] ORAL SOLID PREPARATION COMPOSITION COMPRISING PROTON PUMP INHIBITOR, ORAL SOLID PREPARATION COMPRISING SAME, AND PREPARATION METHOD THEREFOR<br/>[FR] COMPOSITION POUR PRÉPARATION SOLIDE À USAGE ORAL COMPRENANT UN INHIBITEUR DE POMPE À PROTONS, PRÉPARATION SOLIDE À USAGE ORAL LA COMPRENANT, ET SON PROCÉDÉ DE PRÉPARATION<br/>[KO] 프로톤 펌프 저해제를 포함하는 경구용 고형제제 조성물, 이를 포함하는 경구용 고형제제 및 그 제조방법
  申请人：LOTTE FINE CHEMICAL CO LTD

  公开号：WO2019004770A2

  公开（公告）日：2019-01-03

  본 발명은 프로톤 펌프 저해제 또는 이의 약학적으로 허용 가능한 염; 및 염기성 첨가제를 포함하는 결합액;을 포함하되, 상기 염기성 첨가제의 함량은 상기 프로톤 펌프 저해제 또는 이의 약학적으로 허용 가능한 염 100중량부를 기준으로 2 ~ 13중량부인 것을 특징으로 하는 경구용 고형제제 조성물 및 이를 경구용 고형제제 및 그 제조방법에 관한 것이다. 본 발명에 따르면, 유연물질 생성이 현저히 감소되면서 수분 및 낮은 pH에 대한 안정성이 우수한 경구용 고형제제를 제공할 수 있다.