5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfonyl)-1H-imidazo[4,5-b]pyridine | 223713-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfonyl)-1H-imidazo[4,5-b]pyridine
• 英文别名: tenatoprazole sulfone；TU-502；5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfonyl]-1H-imidazo[4,5-b]pyridine
• CAS: 223713-77-7
• 化学式: C₁₆H₁₈N₄O₄S
• 分子量: 362.409
• InChiKey: AXUUZARNKUYLQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-甲氧基-2-(4-甲氧基-3,5-二甲基吡啶-2-基)甲硫基)-3H-咪唑并[4,5-b]吡啶	5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine	113713-24-9	C16H18N4O2S	330.411

反应信息

• 作为产物：
  描述：

  5-甲氧基-2-(4-甲氧基-3,5-二甲基吡啶-2-基)甲硫基)-3H-咪唑并[4,5-b]吡啶 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以71%的产率得到5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfonyl)-1H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis and Characterization of Metabolites and Potential Impurities of the Antiulcerative Drug Tenatoprazole

  摘要：

  Tenatoprazole (Ulsacare (R)) is a recently developed antiulcerative drug used for the treatment of both erosive and nonerosive gastroesophageal reflux disease. During the bulk synthesis of tenatoprazole, we have observed four impurities (tenatoprazole N-oxide, tenatoprazole sulfone N-oxide, N-methyl tenatoprazole, and desmethoxy tenatoprazole) and two metabolites (tenatoprazole sulfide and tenatoprazole sulfone). The present work describes the synthesis and characterization of these impurities.

  DOI：

  10.1080/00397910801986192

文献信息

• Method For Enantioselective Preparation Of Sulphoxide Derivatives
  申请人：Cohen Avraham

  公开号：US20070299261A1

  公开（公告）日：2007-12-27

  The present invention concerns enantioselective preparation of sulphoxide derivatives or their salts. The method consist in performing an enantioselective oxidation of a sulphur of general formula (I) A-CH 2 —SB, wherein: A is a diversely substituted pyridinyl ring and B is a heterocyclic radical comprising an imidazo-pyridinyl ring, using an oxidizing agent in the presence of a titanium (IV) -based catalyst and a chiral ligand consisting of a cyclic beta or gamma-amino-alcohol, in an organic solvent, followed, if required, by salt formation with a base. The invention is useful for preparing sulphoxides useful in therapeutics.

  本发明涉及对亚砜衍生物或其盐的对映选择性制备。该方法包括在一般式（I）A-CH2-SB的硫上进行对映选择性氧化，其中：A是多样取代的吡啶环，B是含有咪唑吡啶环的杂环基，使用一种氧化剂，在钛（IV）基催化剂和由环状β或γ-氨基醇组成的手性配体的存在下，在有机溶剂中进行，随后，如有必要，通过碱形成盐。该发明对于制备在治疗中有用的亚砜具有用处。
• Enantiomer (-) of tenatoprazole and the therapeutic use thereof
  申请人：Cohen Avraham

  公开号：US20050119298A1

  公开（公告）日：2005-06-02

  The invention relates to enantiomer (−) of tentoprazole. The inventive enantiomer (−) of tenatoprazole, or (−)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfonyl]imidazol[4,5-b]pyridine exhibits improved pharmacokinetic properties which make it possible to use a once a day posology of a drug for relevant indications. Said invention can be used for curing digestive pathologies.

  本发明涉及左旋异构体（−）质子泵抑制剂泰妥珂酮。本发明的左旋异构体（−）泰妥珂酮或（−）-5-甲氧基-2-[[(4-甲氧基-3,5-二甲基-2-吡啶基)甲基]磺酰基]咪唑[4,5-b]吡啶具有改善的药代动力学特性，使其可以用于相关适应症的一次日剂量药物治疗。该发明可用于治疗消化道病理学。
• [EN] CONTINUOUS FLOW PROCESS FOR THE PREPARATION OF SULPHOXIDE COMPOUNDS<br/>[FR] PROCESSUS D'ÉCOULEMENT CONTINU POUR LA PRÉPARATION DE COMPOSÉS SULFOXYDE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012004802A8

  公开（公告）日：2012-07-12
• A new titanate/(+)-(1R,2S)-cis-1-amino-2-indanol system for the asymmetric synthesis of (S)-tenatoprazole
  作者：Madeleine Delamare、Sébastien Belot、Jean-Claude Caille、Frédéric Martinet、Henri B. Kagan、Vivien Henryon

  DOI：10.1016/j.tetlet.2009.01.111

  日期：2009.4

  Tenatoprazole, a substituted imidazopyridinyl derivative, is an irreversible proton pump inhibitor (PPI), which is used for the prevention and treatment of gastric acid-related diseases. A new highly efficient asymmetric oxidation using cumene hydroperoxide (CHP) as the oxidant in the presence of titanium tetraisopropoxide (Ti(OiPr)(4)) and (+)-(1R,2S)-cis-1-amino-2-indanol, in a polar aprotic solvent at 0-20 degrees C, has been developed to prepare tenatoprazole with an enantiomeric excess of >99%, a chemoselectivity of >90% and a chemical yield of >90% from the corresponding sulfide. This procedure was successfully implemented on scales ranging from 100 mg to multiple kilograms. Detailed studies of the parameters controlling purity and yield for this reaction are presented. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and Characterization of Metabolites and Potential Impurities of the Antiulcerative Drug Tenatoprazole
  作者：Ganta Madhusudhan Reddy、V. V. N. K. V. Prasada Raju、J. Moses Babu、Ch. Praveen、Mayur Khunt、K. Mukkanti、Padi Pratap Reddy

  DOI：10.1080/00397910801986192

  日期：2008.5

  Tenatoprazole (Ulsacare (R)) is a recently developed antiulcerative drug used for the treatment of both erosive and nonerosive gastroesophageal reflux disease. During the bulk synthesis of tenatoprazole, we have observed four impurities (tenatoprazole N-oxide, tenatoprazole sulfone N-oxide, N-methyl tenatoprazole, and desmethoxy tenatoprazole) and two metabolites (tenatoprazole sulfide and tenatoprazole sulfone). The present work describes the synthesis and characterization of these impurities.