埃格列净杂质6 | 1298086-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 埃格列净杂质6
• 英文名称: (1S,2S,3S,4R,5S)-5-{4-chloro-3-[(4-ethoxy-phenyl)-hydroxy-methyl]-phenyl}-1-hydroxymethyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3,4-triol
• 英文别名: (1S,2S,3S,4R,5S)-5-{4-Chloro-3-[(4-ethoxy-phenyl)-hydroxy-methyl]-phenyl}-1-hydroxymethyl-6,8-dioxa-bicyclo[3.2.1]octan-2,3,4-triol；Ertugliflozin Impurity 9；(1S,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)-hydroxymethyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
• CAS: 1298086-28-8
• 化学式: C₂₂H₂₅ClO₈
• 分子量: 452.889
• InChiKey: XLJINMDXOSTAIJ-BHPIROGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3S,4S)-2,3,4-tris(benzyloxy)-1-(3-((benzyloxy)(4-ethoxyphenyl)methyl)-4-chlorophenyl)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-butan-1-one 在 盐酸 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 埃格列净杂质6
  参考文献：
  名称：

  Commercial Route Research and Development for SGLT2 Inhibitor Candidate Ertugliflozin

  摘要：

  A practical synthesis of SGLT2 inhibitor candidate ertugliflozin (1) has been developed for potential commercial application. The highly telescoped process involves only three intermediate isolations over a 12-step sequence. The dioxabicyclo[3.2.1]octane motif is prepared from commercially available 2,3,4,6-tetra-O-benzyl-D-glucose, with nucleophilic hydroxymethylation of a 5-ketogluconamide intermediate as a key step. The aglycone moiety is introduced via aryl anion, addition to a methylpiperazine amide. High chemical purity of the API is assured through isolation of the crystalline penultimate intermediate, tetraacetate 39. A cocrystalline complex of the amorphous solid 1 with L-pyroglutamic acid has been prepared in order to improve the physical properties for manufacture and to ensure robust API quality.

  DOI：

  10.1021/op4002802

文献信息

• [EN] DIOXA-BICYCLO[3.2.1]OCTANE-2,3,4-TRIOL DERIVATIVES<br/>[FR] DÉRIVÉS DIOXA-BICYCLO[3.2.1]OCTANE-2,3,4-TRIOL
  申请人：PFIZER

  公开号：WO2011051864A1

  公开（公告）日：2011-05-05

  Compounds of Formula (A) and (B) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by sodium-glucose transporter inhibitors (in particular, SGLT2 inhibitors).

  本文描述了化合物(A)和(B)的化学式及其用途，用于治疗由钠葡萄糖转运体抑制剂（特别是SGLT2抑制剂）介导的疾病、症状和/或紊乱。
• DIOXA-BICYCLO[3.2.1]OCTANE-2,3,4-TRIOL DERIVATIVES
  申请人：Mascitti Vincent

  公开号：US20120184486A1

  公开（公告）日：2012-07-19

  Compounds of Formula (A) and (B) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by sodium-glucose transporter inhibitors (in particular, SGLT2 inhibitors).

  本文描述了化合物(A)和(B)的公式以及它们在治疗由钠-葡萄糖转运抑制剂（特别是SGLT2抑制剂）介导的疾病、状况和/或障碍方面的用途。
• Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
  申请人：Mascitti Vincent

  公开号：US08669380B2

  公开（公告）日：2014-03-11

  Compounds of Formula (A) and (B) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by sodium-glucose transporter inhibitors (in particular, SGLT2 inhibitors).

  本文描述了化学式(A)和(B)的化合物及其用途，用于治疗由钠葡萄糖转运抑制剂（特别是SGLT2抑制剂）介导的疾病、病况和/或障碍。
• 艾托格列净杂质的合成方法
  申请人：江苏海悦康医药科技有限公司

  公开号：CN117624265A

  公开（公告）日：2024-03-01

  本发明属于化学合成技术领域，具体涉及艾托格列净杂质的合成方法，艾托格列净杂质包括式I化合物，式II化合物，式III化合物中的至少一种。本发明能够高效简便地合成艾托格列净杂质，便于对艾托格列净原料药及其制剂的杂质进行分析和研究，同时提高了艾托格列净的生产和用药的安全性。
• US8669380B2
  申请人：——

  公开号：US8669380B2

  公开（公告）日：2014-03-11