3-benzyloxy-4(1H)-pyridone | 1138-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyloxy-4(1H)-pyridone
• 英文别名: 3-benzyloxy-1H-pyridin-4-one；3-Benzyloxy-4(1H)-pyridon；3-benzyloxy-1H-pyridin-4-one；3-phenylmethoxy-1H-pyridin-4-one
• CAS: 1138-45-0
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: NZWMMUSDSPVNRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-4(1H)-pyridone 在 环己烯 作用下， 以 乙醇 、 水 为溶剂， 反应 192.0h， 生成 3-hydroxy-5-methyl-4(1H)-pyridone hydrochloride
  参考文献：
  名称：

  Systematic comparison of the mono-, dimethyl- and trimethyl 3-hydroxy-4(1H)-pyridones – Attempted optimization of the orally active iron chelator, deferiprone

  摘要：

  A range of close analogues of deferiprone have been synthesised. The group includes mono-, di- and trimethyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe(3+) values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NH-containing hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues.As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.014
• 作为产物：
  描述：

  5-（苄氧基-2-（羟甲基)-4H-吡喃-4-酮 在 Jones reagent 、 氨 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 水 、 丙酮 为溶剂， 反应 31.0h， 生成 3-benzyloxy-4(1H)-pyridone
  参考文献：
  名称：

  Systematic comparison of the mono-, dimethyl- and trimethyl 3-hydroxy-4(1H)-pyridones – Attempted optimization of the orally active iron chelator, deferiprone

  摘要：

  A range of close analogues of deferiprone have been synthesised. The group includes mono-, di- and trimethyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe(3+) values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NH-containing hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues.As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.014

文献信息

• [EN] CYCLOALKYL DERIVATIVES OF 3-HYDROXY-4-PYRIDINONES<br/>[FR] DERIVES CYCLOALKYLE DE 3-HYDROXY-4-PYRIDINONES
  申请人：APOTEX INC

  公开号：WO2005049609A1

  公开（公告）日：2005-06-02

  The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula (I); wherein R1 is X with the proviso that R2 is Y; or R1 is T with the proviso that R2 is W; or R1 is X with the proviso that R 2 R 5 N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C1 to C6 alkyl groups. X is C3-C6 cycloalkyl; Y is selected from the group consisting of C1 to C6 cycloalkyl; C1 to C6 alkyl, and C1 to C6 alkyl monosubstituted with a C3-C6 cycloalkyl; T is C1 to C6 alkyl; W is C3-C6 cycloalkyl; R3 is selected from the group consisting of hydrogen and C1 to C6 alkyl; R4 is selected from the group consisting of hydrogen and C1 to C6 alkyl; R5 is selected from the group consisting of hydrogen and C1 to C6 alkyl; and its pharmaceutically acceptable salt thereof. Pharmaceutical compositions of such compounds are useful in the removal of excess body iron from patients with iron overload diseases.

  本发明提供了一种3-羟基-4-吡啶酮的环烷基衍生物，可用于螯合金属离子，如铁。描述了其制备和用途。特别是，本发明涉及化学和生物系统中铁的去除，包括具有式（I）的螯合剂；其中R1是X，但R2是Y；或R1是T，但R2是W；或R1是X，但R2R5N在一起形成从哌啶基，吗啉基，吡咯烷基或哌嗪基中选择的杂环环，其中哌啶基，吗啉基，吡咯烷基或哌嗪基的基团是未取代或用1至3个C1至C6烷基取代。X是C3-C6环烷基；Y选自由C1至C6环烷基；C1至C6烷基和C1至C6烷基单取代的C3-C6环烷基；T是C1至C6烷基；W是C3-C6环烷基；R3选自氢和C1至C6烷基的群；R4选自氢和C1至C6烷基的群；R5选自氢和C1至C6烷基的群；以及其药学上可接受的盐。这些化合物的制药组合物可用于从铁过载病患者中去除体内过量的铁。
• Cycloalkyl derivatives of 3-hydroxy-4-pyridinones field of the invention
  申请人：Tam Fat Tim

  公开号：US20070082904A1

  公开（公告）日：2007-04-12

  The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula (I); wherein R 1 is X with the proviso that R 2 is y; or R 1 is T with the proviso that R 2 is W; or R 1 is X with the proviso that R 2 R 5 N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morphoninyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C 1 to C 6 alkyl groups. X is C 3 -C 6 cycloalkyl; Y is selected from the group consisting of C, to C 6 cycloalkyl; C 1 to C 6 alkyl, and C 1 to C 6 alkyl monosubstituted with a C 3 -C 6 cycloalkyl; T is C 1 to C 6 alkyl; W is C 3 -C 6 cycloalkyl; R 3 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; R 4 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; R 5 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; and its pharmaceutically acceptable salt thereof. Pharmaceutical compositions of such compounds are useful in the removal of excess body iron from patients with iron overload diseases.

  本发明提供了3-羟基-4-吡啶酮的环烷基衍生物，可用于螯合金属离子，如铁离子。描述了其制备和用途。特别是，本发明涉及化学和生物系统中铁的去除，包括具有式（I）的螯合剂，其中R1为X，但R2为y；或R1为T，但R2为W；或R1为X，但R2R5N在一起形成从哌啶基，吗啉基，吡咯烷基或哌嗪基中选择的杂环环，其中哌啶基，吗啉基，吡咯烷基或哌嗪基的基团是未取代的或用1至3个C1至C6烷基基团取代的。X为C3-C6环烷基；Y选自由C到C6环烷基；C1到C6烷基和C1到C6烷基单取代的C3-C6环烷基；T为C1到C6烷基；W为C3-C6环烷基；R3选自氢和C1到C6烷基的群；R4选自氢和C1到C6烷基的群；R5选自氢和C1到C6烷基的群；以及其药学上可接受的盐。这些化合物的制药组合物可用于治疗铁过载病患者的体内多余铁的去除。
• Cycloalkyl derivatives of 3-hydroxy-4-pyridinones
  申请人：Tam Tim Fat

  公开号：US20090170850A1

  公开（公告）日：2009-07-02

  The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula I wherein R 1 is X with the proviso that R 2 is Y; or R 1 is T with the proviso that R 2 is W; or R 1 is X with the proviso that R 2 R 5 N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C 1 to C 6 alkyl groups. X is C 3 -C 6 cycloalkyl; Y is selected from the group consisting of C 1 to C 6 cycloalkyl; C 1 to C 6 alkyl, and C 1 to C 6 alkyl monosubstituted with a C 3 -C 6 cycloalkyl; T is C 1 to C 6 alkyl; W is C 3 -C 6 cycloalkyl; R 3 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; R 4 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; R 5 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; and its pharmaceutically acceptable salt thereof. Pharmaceutical compositions of such compounds are useful in the removal of excess body iron from patients with iron overload diseases.

  本发明提供了3-羟基-4-吡啶酮的环烷基衍生物，可用于螯合金属离子，如铁离子。描述了其制备和使用。具体而言，本发明涉及在化学和生物系统中除铁，包括具有式I的螯合剂，其中R1是X，但R2是Y；或R1是T，但R2是W；或R1是X，但R2和R5N在一起形成从哌啶基，吗啡啉基，吡咯烷基或哌嗪基中选择的杂环环，其中哌啶基，吗啡啉基，吡咯烷基或哌嗪基的基团是未取代或用一到三个C1到C6烷基基团取代。X是C3-C6环烷基；Y选自由C1到C6环烷基；C1到C6烷基；和用C3-C6环烷基单取代的C1到C6烷基。T是C1到C6烷基；W是C3-C6环烷基；R3选自氢和C1到C6烷基的群；R4选自氢和C1到C6烷基的群；R5选自氢和C1到C6烷基的群；以及其药学上可接受的盐。这些化合物的制药组合物对于从铁过载病患者中去除过量体内铁非常有用。
• 2-Oxo-1-(substituted phosphorous)azetidines
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0243924A2

  公开（公告）日：1987-11-04

  Antibacterial activity is exhibited by 2-azetidinones having an acylamino substituent in the 3-position and having an activating group in the 1-position of the formula wherein R4 is -CH2-Z, or and Z is

  在 3 位上具有酰氨基取代基并在 1 位上具有活化基团的 2-氮杂环丁酮具有抗菌活性，其式为 其中 R4 为 -CH2-Z、 或 而 Z 是
• CHIRAL 3-HYDROXYPYRID-4-ONE DERIVATIVE, AND SYNTHESIS AND USE THEREOF
  申请人：Zhejiang University

  公开号：EP2692724A1

  公开（公告）日：2014-02-05

  Disclosed are a chiral 3-hydroxypyrid-4-one derivative and a salt thereof. The compound is acquired by reacting methyl maltol or ethyl maltol with benzyl chloride to acquire a 3-benzyl protected maltol, then by reacting compound VII with different chiral amino alcohols to acquire 3-benzyloxypyrid-4-one, and finally by performing a palladium on carbon-catalyzed hydride reduction deprotection on compound IX. The compound of the present invention is capable of having iron ion chelating bioactivity, and is applicable in preparing an anti-iron overload medicament. The structure of the compound of the present invention is represented as formula (I).

  本发明公开了一种手性 3-羟基吡啶-4-酮衍生物及其盐。该化合物是通过甲基麦芽酚或乙基麦芽酚与氯化苄反应获得 3-苄基保护麦芽酚，然后通过化合物 VII 与不同的手性氨基醇反应获得 3-苄氧基吡啶-4-酮，最后通过对化合物 IX 进行碳上钯催化的氢化物还原脱保护而获得。本发明化合物具有铁离子螯合生物活性，适用于制备抗铁超载药物。本发明化合物的结构如式（I）所示。