5-(4-(2-(5-(1-(甲氧基甲氧基)乙基)吡啶-2-基)乙氧基)苄基)噻唑烷-2,4-二酮 | 184766-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(4-(2-(5-(1-(甲氧基甲氧基)乙基)吡啶-2-基)乙氧基)苄基)噻唑烷-2,4-二酮
• 英文名称: 5-(4-(2-(5-(1-(methoxymethoxy)ethyl)pyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione
• 英文别名: 5-[[4-[2-[5-[1-(methoxymethoxy)ethyl]pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 184766-39-0
• 化学式: C₂₁H₂₄N₂O₅S
• 分子量: 416.498
• InChiKey: UDDCGCGNWXOFEI-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  601.7±55.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(4-(2-(5-(1-(甲氧基甲氧基)乙基)吡啶-2-基)乙氧基)苄基)噻唑烷-2,4-二酮 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以250 mg的产率得到Hydroxypioglitazone
  参考文献：
  名称：

  [EN] 2,4-THIAZOLIDINEDIONE DERIVATIVES IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
  [FR] DÉRIVÉS DE 2,4-THIAZOLIDINEDIONE DANS LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL

  摘要：

  本发明提供了5-(4-(2-(5-(1-羟乙基)吡啶-2-基)乙氧基)苄基)噻唑二酮-2,4-二酮及其新的立体异构体，用于治疗中枢神经系统（NS）疾病。

  公开号：

  WO2015150476A1
• 作为产物：
  描述：

  5-乙酰基-2-甲基吡啶 在 哌啶 、 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 乙醇 、 水 、 sodium hydride 、 sodium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基乙二醛肟 、 甲苯 为溶剂， 反应 42.0h， 生成 5-(4-(2-(5-(1-(甲氧基甲氧基)乙基)吡啶-2-基)乙氧基)苄基)噻唑烷-2,4-二酮
  参考文献：
  名称：

  [EN] 2,4-THIAZOLIDINEDIONE DERIVATIVES IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
  [FR] DÉRIVÉS DE 2,4-THIAZOLIDINEDIONE DANS LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL

  摘要：

  本发明提供了5-(4-(2-(5-(1-羟乙基)吡啶-2-基)乙氧基)苄基)噻唑二酮-2,4-二酮及其新的立体异构体，用于治疗中枢神经系统（NS）疾病。

  公开号：

  WO2015150476A1

文献信息

• [EN] PROCESS FOR PREPARING 5-[[4-[2-[5-(1-HYDROXYETHYL)-2-PYRIDINYL]ETHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE AND SALTS THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 5-[[4-[2-[5-(1-HYDROXYÉTHYL)-2-PYRIDINYL]ÉTHOXY]PHÉNYL]MÉTHYL]-2,4-THIAZOLIDINEDIONE ET DE SES SELS
  申请人：MINORYX THERAPEUTICS S L

  公开号：WO2018116281A1

  公开（公告）日：2018-06-28

  The disclosure provides a process of making the compound of Formula I, and pharmaceutically acceptable salts thereof: and the process of making the intermediate of Formula III: wherein PG is as defined as set forth in the specification.

  该公开提供了制备化合物I及其药用可接受盐的过程：以及制备中间体III的过程：其中PG如规范中所定义。
• 2,4-THIAZOLIDINEDIONE DERIVATIVES IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：MINORYX THERAPEUTICS S.L.

  公开号：US20160235729A1

  公开（公告）日：2016-08-18

  The present invention provides 5-(4-(2-(5-(1-hydroxyethyl)pyridine-2-yl)ethoxy) benzyl)thiazolidine-2,4-dione and novel stereoisomers of said compound for use in the treatment of central nervous system (NS) disorders.

  本发明提供了5-(4-(2-(5-(1-羟乙基)吡啶-2-基)乙氧基)苄基)噻唑烷-2,4-二酮及其新的立体异构体，用于治疗中枢神经系统（NS）疾病。
• 2,4-thiazolidinedione derivatives in the treatment of central nervous system disorders
  申请人：MINORYX THERAPEUTICS S.L.

  公开号：US10179126B2

  公开（公告）日：2019-01-15

  The present invention provides 5-(4-(2-(5-(1-hydroxyethyl)pyridine-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione and novel stereoisomers of said compound for use in the treatment of central nervous system (NS) disorders.

  本发明提供了用于治疗中枢神经系统（NS）疾病的 5-(4-(2-(5-(1-羟乙基)吡啶-2-基)乙氧基)苄基)噻唑烷-2,4-二酮和所述化合物的新型立体异构体。
• Process for preparing 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione and salts thereof
  申请人：Minoryx Therapeutics S.L.

  公开号：US11124505B2

  公开（公告）日：2021-09-21

  The disclosure provides a process of making the compound of Formula I, and pharmaceutically acceptable salts thereof: and the process of making the intermediate of Formula III: wherein PG is as defined as set forth in the specification.

  本公开提供了一种式 I 化合物及其药学上可接受的盐的制造工艺：以及式 III 中间体的制造工艺：其中 PG 的定义如说明书所述。
• Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone
  作者：Steven P. Tanis、Timothy T. Parker、Jerry R. Colca、Roberta M. Fisher、Rolf F. Kletzein

  DOI：10.1021/jm9605694

  日期：1996.1.1

  Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible; clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in, vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).