3-(benzyloxy)-5-{[(1S)-1-(methoxymethyl)propyl]oxy}benzoic acid | 883748-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(benzyloxy)-5-{[(1S)-1-(methoxymethyl)propyl]oxy}benzoic acid
• 英文别名: 3-({(1S)-1-[(methyloxy)methyl]propyl}oxy)-5-[(phenylmethyl)oxy]benzoic acid；3-(Benzyloxy)-5-{[(2S)-1-methoxybutan-2-yl]oxy}benzoic acid；3-[(2S)-1-methoxybutan-2-yl]oxy-5-phenylmethoxybenzoic acid
• CAS: 883748-50-3
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: ODRROWDZBTZLKC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)-5-{[(1S)-1-(methoxymethyl)propyl]oxy}benzoic acid 在 palladium 10% on activated carbon 氢气 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 3-hydroxy-5-({(1S)-1-[(methyloxy)methyl]propyl}oxy)-N-(1-methyl-1H-pyrazol-3-yl)benzamide
  参考文献：
  名称：

  WO2006/125972

  摘要：

  公开号：
• 作为产物：
  描述：

  3-(苄氧基)-5-羟基苯甲酸甲酯 在 lithium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 18.5h， 生成 3-(benzyloxy)-5-{[(1S)-1-(methoxymethyl)propyl]oxy}benzoic acid
  参考文献：
  名称：

  WO2006/125972

  摘要：

  公开号：

文献信息

• [EN] PHENOXY BENZAMIDE COMPOUNDS WITH UTILITY IN THE TREATMENT OF TYPE 2 DIABETES AND OBESITY<br/>[FR] COMPOSES DE PHENOXY BENZAMIDE AYANT UNE UTILITE DANS LE TRAITEMENT DU DIABETE DE TYPE 2 ET DE L'OBESITE
  申请人：ASTRAZENECA AB

  公开号：WO2006040528A1

  公开（公告）日：2006-04-20

  Compounds of Formula: (I); wherein: R1 is methoxymethyl; R2 is selected from -C(O)NR4R5, SO2NR4R5, S(O)pR4 and HET-2; HET-1 is a 5- or 6-membered, optionally substituted C-linked heteroaryl ring; HET-2 is a 4-, 5- or 6-membered, C- or N-linked optionally substituted heterocyclyl ring; R3 is selected from halo, fluoromethyl, difluoromethyl, trifluoromethyl, methyl, methoxy and cyano; R4 is selected from for example hydrogen, optionally substituted (1-4C)alkyl and HET-2; R5 is hydrogen or (1-4C)alkyl; or R4 and R5 together with the nitrogen atom to which they are attached may form a heterocyclyl ring system as defined by HET-3; HET-3 is for example an optionally substituted N-linked, 4, 5 or 6 membered, saturated or partially unsaturated heterocyclyl ring; p is (independently at each occurrence) 0, 1 or 2; m is 0 or 1; n is 0, 1 or 2; provided that when m is 0, then n is 1 or 2; or a salt, pro drug or solvate thereof, are described. Their use as GLK activators, pharmaceutical compositions containing them, and processes for their preparation are also described.

  化合物的分子式为：(I)；其中：R1为甲氧甲基；R2选择自-C(O)NR4R5、SO2NR4R5、S(O)pR4和HET-2；HET-1为5-或6-成员的、可选择性取代的C-连接杂芳基环；HET-2为4-、5-或6-成员的、C-或N-连接的可选择性取代的杂环烷基环；R3选择自卤素、氟甲基、二氟甲基、三氟甲基、甲基、甲氧基和氰基；R4选择自氢、可选择性取代的(1-4C)烷基和HET-2；R5为氢或(1-4C)烷基；或者R4和R5连同它们连接的氮原子可以形成由HET-3定义的杂环烷基环系统；HET-3例如为可选择性取代的N-连接、4、5或6成员的、饱和或部分不饱和的杂环烷基环；p为（每次独立）0、1或2；m为0或1；n为0、1或2；条件是当m为0时，n为1或2；或其盐、前药或溶剂化合物。描述了它们作为GLK激活剂的用途、含有它们的药物组合物以及它们的制备方法。
• [EN] BENZAMIDE DERIVATIVES THAT ACT UPON THE GLUCOKINASE ENZYME<br/>[FR] DERIVES DE BENZAMIDE AGISSANT SUR L'ENZYME GLUCOKINASE
  申请人：ASTRAZENECA AB

  公开号：WO2006040529A1

  公开（公告）日：2006-04-20

  Compounds of Formula: (I); wherein: R1 is hydroxymethyl; R2 is selected from -C(O)NR4R5, SO2NR4R5, S(O)pR4 and HET-2; HET-1 is a 5- or 6-membered, optionally substituted C-linked heteroaryl ring; HET-2 is a 4-, 5- or 6-membered, C- or N-linked optionally substituted heterocyclyl ring; R3 is selected from halo, fluoromethyl, difluoromethyl, trifluoromethyl, methyl, methoxy and cyano; R4 is selected from for example hydrogen, optionally substituted (1-4C)alkyl and HET-2; R5 is hydrogen or (1-4C)alkyl; or R4 and R5 together with the nitrogen atom to which they are attached may form a heterocyclyl ring system as defined by HET-3; HET-3 is for example an optionally substituted N-linked, 4, 5 or 6 membered, saturated or partially unsaturated heterocyclyl ring; p is (independently at each occurrence) 0, 1 or 2; m is 0 or 1; n is 0, 1 or 2; provided that when m is 0, then n is 1 or 2; or a salt, pro drug or solvate thereof, are described. Their use as GLK activators, pharmaceutical compositions containing them, and processes for their preparation are also described.

  化合物的化学式：（I）；其中：R1为羟甲基；R2选自-C（O）NR4R5，SO2NR4R5，S（O）pR4和HET-2；HET-1为一个5-或6-成员的、可选择地取代的C-连接的杂芳基环；HET-2为一个4-、5-或6-成员的、C-或N-连接的可选择地取代的杂环基环；R3选自卤素、氟甲基、二氟甲基、三氟甲基、甲基、甲氧基和氰基；R4选自例如氢、可选择地取代的（1-4C）烷基和HET-2；R5为氢或（1-4C）烷基；或R4和R5与它们连接的氮原子一起可以形成由HET-3定义的杂环基环系统；HET-3为例如一个可选择地取代的N-连接的、4、5或6成员的、饱和或部分不饱和的杂环基环；p为（每次独立）0、1或2；m为0或1；n为0、1或2；但是当m为0时，n为1或2；或其盐、前药或溶剂化合物。描述了它们作为GLK激活剂的用途，含有它们的药物组合物，以及它们的制备方法。
• HETEROARYL BENZAMIDE DERIVATIVES FOR USE AS GLK ACTIVATORS IN THE TREATMENT OF DIABETES
  申请人：MCKERRECHER Darren

  公开号：US20090029905A1

  公开（公告）日：2009-01-29

  Compounds of formula (I) wherein R 1 , HET-1 and HET-2 are as described in the specification, and their salts and prodrugs, are activators of glucokinase (GLK) and are thereby useful in the treatment of, for example, type 2 diabetes. Processes for preparing compounds of formula (I) are also described.

  式(I)中，R1、HET-1和HET-2的化合物，以及它们的盐和前药，是葡萄糖激酶（GLK）的激活剂，因此在治疗例如2型糖尿病方面非常有用。本文还描述了制备式(I)化合物的过程。
• Benzamide Derivatives That Act Upon The Glucokinase Enzyme
  申请人：Johnstone Craig

  公开号：US20070287693A1

  公开（公告）日：2007-12-13

  Compounds of Formula (I): wherein R 1 is hydroxymethyl; R 2 is selected from —C(O)NR 4 R 5 , SO 2 NR 4 R 5 , S(O) p R 4 and HET-2; HET-1 is a 5- or 6-membered, optionally substituted C-linked heteroaryl ring; HET-2 is a 4-, 5- or 6-membered, C- or N-linked optionally substituted hererocyclyl ring; R 3 is selected from halo, fluoromethyl, difluoromethyl, trifluoromethyl, methyl, methoxy and cyano; R 4 is selected from, for example, hydrogen, optionally substituted (1-4C)alkyl and HET-2; R 5 is hydrogen or (1-4C)alkyl; or R 4 and R 5 together with the nitrogen atom to which they are attached may form a heterocyclyl ring system as defined by HET-3; HET-3 is, for example, an optionally substituted N-linked, 4, 5 or 6 membered, saturated or partially unsaturated heterocyclyl ring; p is (independently at each occurrence) 0, 1 or 2; m is 0 or 1; n is 0, 1 or 2; provided that when m is 0, then n is 1 or 2; or a salt, pro drug or solvate thereof, are described. Their use as GLK activators, pharmaceutical compositions containing them, and processes for their preparation are also described.

  化合物的公式（I）：其中R1是羟甲基；R2选自—C（O）NR4R5，SO2NR4R5，S（O）pR4和HET-2；HET-1是5-或6-成员的，可选择取代的C-连接杂芳基环；HET-2是4-，5-或6-成员的，C-或N-连接的可选择取代的杂环基环；R3选自卤素，氟甲基，二氟甲基，三氟甲基，甲基，甲氧基和氰基；R4选自例如氢，可选择取代的（1-4C）烷基和HET-2；R5是氢或（1-4C）烷基；或者R4和R5与它们所连接的氮原子一起可以形成由HET-3定义的杂环基环系统；HET-3是例如可选择取代的N-连接的，4、5或6成员的，饱和或部分不饱和的杂环基环；p（独立于每次出现）为0、1或2；m为0或1；n为0、1或2；但是当m为0时，则n为1或2；还描述了它们的盐，前药或溶剂。还描述了它们作为GLK激活剂的用途，含有它们的制药组合物以及它们的制备方法。
• Phenoxy Benzamide Compounds with Utility in the Treatment of Type 2 Diabetes and Obesity
  申请人：Johnstone Craig

  公开号：US20080280874A1

  公开（公告）日：2008-11-13

  Compounds of Formula (I): wherein: R 1 is methoxymethyl; R 2 is selected from —C(O)NR 4 R 5 , —SO 2 NR 4 R 5 , —S(O) p R 4 and HET-2; HET-1 is a 5- or 6-membered, optionally substituted C-linked heteroaryl ring; HET-2 is a 4-, 5- or 6-membered, C- or N-linked optionally substituted heterocyclyl ring; R 3 is selected from halo, fluoromethyl, difluoromethyl, trifluoromethyl, methyl, methoxy and cyano; R 4 is selected from for example hydrogen, optionally substituted (1-4C)alkyl and HET-2; R 5 is hydrogen or (1-4C)alkyl; or R 4 and R 5 together with the nitrogen atom to which they are attached may form a heterocyclyl ring system as defined by HET-3; HET-3 is for example an optionally substituted N-linked, 4, 5 or 6 membered, saturated or partially unsaturated heterocyclyl ring; p is (independently at each occurrence) 0, 1 or 2; m is 0 or 1; n is 0, 1 or 2; provided that when m is 0, then n is 1 or 2; or a salt, pro-drug or solvate thereof, are described. Their use as GLK activators, pharmaceutical compositions containing them, and processes for their preparation are also described.

  化合物的式子为（I）： 其中：R1为甲氧甲基；R2选自—C（O）NR4R5，—SO2NR4R5，—S（O）pR4和HET-2；HET-1是一个5-或6-成员的，可选择性取代的C-连接杂环芳基环；HET-2是一个4-，5-或6-成员的，C-或N-连接可选择性取代的杂环烷基环；R3选自卤素，氟甲基，二氟甲基，三氟甲基，甲基，甲氧基和氰基；R4选自例如氢，可选择性取代的（1-4C）烷基和HET-2；R5为氢或（1-4C）烷基；或R4和R5与它们连接的氮原子一起可以形成由HET-3定义的杂环烷基环系统；HET-3例如为可选择性取代的N-连接的，4,5或6成员的，饱和或部分不饱和的杂环烷基环；p是（每次独立地）0，1或2；m为0或1；n为0，1或2；前提是当m为0时，n为1或2；或其盐，前药或溶剂。还描述了它们作为GLK激活剂的用途，含有它们的制药组合物以及它们的制备方法。