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达格列净杂质23 | 1079083-63-8

物质功能分类

分析化学 - 标准品 - 药典标准品和杂质标准品

分子结构分类

有机化合物 - 有机氧化合物

中文名称

达格列净杂质23

中文别名

——

英文名称

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

英文别名

Des(tetrahydrofuran) Empagliflozin Tetraacetate；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]oxan-2-yl]methyl acetate

CAS

1079083-63-8

化学式

C₂₇H₂₉ClO₁₀

mdl

——

分子量

548.974

InChiKey

IPPDHWALLUPDNH-MMKSVXGCSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

149-151°C
溶解度：

DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

辛醇/水分配系数(LogP)：

3.4
重原子数：

38
可旋转键数：

12
环数：

3.0
sp3杂化的碳原子比例：

0.41
拓扑面积：

135
氢给体数：

1
氢受体数：

10

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
达格列净杂质24	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	872980-38-6	C₂₈H₃₁ClO₁₀	563.001
(2R,3R,4R,5S,6S)-2-(乙酰氧基甲基)-6-(4-氯-3-(4-乙氧基苄基)苯基)四氢-2H-吡喃-3,4,5-三yl 三乙酸酯	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	461432-25-7	C₂₉H₃₃ClO₁₀	577.028
(2S,3S,4R,5R,6R)-2-(3-(4-乙酰氧基苄基)-4-氯苯基)-6-(乙酰氧基甲基)四氢-2H-吡喃-3,4,5-三乙酸三乙酯	1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(4-acetoxy-benzyl)benzene	912917-85-2	C₂₉H₃₁ClO₁₁	591.012
依帕列净杂质	(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol	864070-37-1	C₁₉H₂₁ClO₆	380.825
(2S,3R,4R,5S,6R)-2-(4-氯-3-(4-甲氧基苄基)苯基)-6-(羟甲基)四氢-2	(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-methoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol	333359-90-3	C₂₀H₂₃ClO₆	394.852
——	dapagliflozin	1118566-45-2	C₂₁H₂₅ClO₆	408.879
——	(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate	1309963-64-1	C₃₄H₄₅ClO₁₁Si	693.263
——	(3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol	912917-83-0	C₂₀H₂₃ClO₇	410.851
——	1-chloro-4-(1-methoxy-D-glucopyranosyl)-2-(4-hydroxybenzyl)-benzene	1204220-63-2	C₂₀H₂₃ClO₇	410.851
——	(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-methoxybenzyl)phenyl)-6-(hydroxymethyl)-2-hydroxytetrahydro-2H-pyran-3,4,5-triol	——	C₂₀H₂₃ClO₇	410.851
——	(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-methoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol	1210040-47-3	C₂₁H₂₅ClO₇	424.878
甲基 1-C-[4-氯-3-[(4-乙氧基苯基)甲基]苯基]-D-吡喃葡萄糖苷	(3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol	461432-24-6	C₂₂H₂₇ClO₇	438.905
——	(2S,3R,4S,5S,6R)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol	1309963-63-0	C₂₆H₃₇ClO₇Si	525.114
(3R,4S,5R,6R)-2-(4-氯-3-(4-乙氧基苄基)苯基)-3,4,5-三((三甲基甲硅烷基)氧基)-6-(((三甲基甲硅烷基)氧基)甲基)四氢-2H-吡喃-2-醇	(3R,4S,5R,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-ol	960494-15-9	C₃₃H₅₇ClO₇Si₄	713.606

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-hydroxyethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1309964-03-1	C₂₉H₃₃ClO₁₁	593.027
——	(2R,3R,4R,5S,65)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-oxoethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1426924-85-7	C₂₉H₃₁ClO₁₁	591.012
——	1-chloro-2-(4-cyano-benzyl)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzene	946525-42-4	C₂₈H₂₈ClNO₉	557.985
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1426924-86-8	C₃₀H₃₄ClNO₁₁	620.053
——	acetic acid (2R,3R,4R,SS,6S)-3,4,5-triacetoxy-6-[4-chloro-3-{3-amino-4-hydroxy-benzyl}-phenyl]-tetrahydro-pyran-2-ylmethyl ester	1291094-53-5	C₂₇H₃₀ClNO₁₀	563.989
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-acetylbenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1118566-90-7	C₂₉H₃₁ClO₁₀	575.012
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	915095-99-7	C₃₁H₃₅ClO₁₁	619.065
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butoxycarbonyl)amino)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1079083-65-0	C₃₄H₄₂ClNO₁₂	692.16
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(3-((tert-butoxycarbonyl)amino)propoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1079084-05-1	C₃₅H₄₄ClNO₁₂	706.187
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1309964-02-0	C₃₅H₄₇ClO₁₁Si	707.29
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(4-((tert-butoxycarbonyl)amino)butoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1079084-07-3	C₃₆H₄₆ClNO₁₂	720.214
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-((6-((tert-butoxycarbonyl)amino)hexyl)oxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1079084-08-4	C₃₈H₅₀ClNO₁₂	748.267
——	1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(trifluoromethylsulfonyloxy)-benzyl]-benzene	892487-00-2	C₂₈H₂₈ClF₃O₁₂S	681.037
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(1-(ethoxyimino)ethyl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1416165-35-9	C₃₁H₃₆ClNO₁₀	618.081
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-((4-(((tert-butoxycarbonyl)amino)methyl)benzyl)oxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1079083-82-1	C₄₀H₄₆ClNO₁₂	768.258
——	acetic acid (2R,3R,4R,SS,6S)-3,4,5-triacetoxy-6-[4-chloro-3-{4-hydroxy-3-nitro-benzyl}-phenyl]-tetrahydro-pyran-2-ylmethyl ester	1291094-41-1	C₂₇H₂₈ClNO₁₂	593.972
依帕列净杂质	(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol	864070-37-1	C₁₉H₂₁ClO₆	380.825
——	acetic acid (2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-(2-cyano-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2-ylmethyl ester	1291094-54-6	C₃₀H₃₁ClN₂O₁₀	615.037
达格列嗪	dapagliflozin	461432-26-8	C₂₁H₂₅ClO₆	408.879
——	1-{3-(4-[2-(4-methylphenoxy)ethoxy]benzyl)-4-chlorophenyl}-1-deoxy-β-D-glucopyranose	——	C₂₈H₃₁ClO₇	515.003
——	2-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime	1426924-84-6	C₂₂H₂₆ClNO₇	451.904
——	1-{3-(4-[2-(2-methylphenoxy)ethoxy]benzyl)-4-chlorophenyl}-1-deoxy-β-D-glucopyranose	——	C₂₈H₃₁ClO₇	515.003
——	4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile	946525-40-2	C₂₀H₂₀ClNO₅	389.835
——	1-{3-(4-[2-(2-chlorophenoxy)ethoxy]benzyl)-4-chlorophenyl}-1-deoxy-β-D-glucopyranose	——	C₂₇H₂₈Cl₂O₇	535.421
依帕列净	empagliflozin	864070-44-0	C₂₃H₂₇ClO₇	450.916
——	empagliflozin	1417573-74-0	C₂₃H₂₇ClO₇	450.916
——	2-{4-[2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2-nitro-phenoxy}-2-methyl-propionic acid ethyl ester	1291094-42-2	C₃₃H₃₈ClNO₁₄	708.116
——	[(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate	1291094-43-3	C₃₁H₃₄ClNO₁₁	632.064
——	(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((8-(1,3-dioxoisoindolin-2-yl)octyl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1079084-11-9	C₄₃H₄₈ClNO₁₂	806.307
——	1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone	1204220-56-3	C₂₁H₂₃ClO₆	406.863
——	1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-methyl oxime	1416164-43-6	C₂₂H₂₆ClNO₆	435.905
——	1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime	1416164-51-6	C₂₃H₂₈ClNO₆	449.931
——	6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carbonitrile	1291094-55-7	C₂₂H₂₃ClN₂O₆	446.887
——	6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid	1291094-57-9	C₂₂H₂₄ClNO₈	465.887
——	6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester	1291094-56-8	C₂₃H₂₆ClNO₈	479.914
——	6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one	1291094-44-4	C₂₃H₂₆ClNO₇	463.915

反应信息

作为反应物：

描述：

达格列净杂质23 在 1,1'-双(二苯基膦)二茂铁、四(三苯基膦)钯 lithium hydroxide monohydrate 、水、三乙胺作用下，以四氢呋喃、甲醇、二氯甲烷、 N,N-二甲基甲酰胺为溶剂，反应 6.0h，生成 4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

参考文献：

名称：

[EN] NOVEL SGLT INHIBITORS
[FR] NOUVEAUX INHIBITEURS SGLT

摘要：

公开号：

WO2012172566A3
作为产物：

描述：

葡萄糖酸内酯在 N-甲基吗啉、吡啶、三乙基硅烷、 4-二甲氨基吡啶、正丁基锂、甲烷磺酸、三氟化硼乙醚、三溴化硼作用下，以四氢呋喃、正己烷、二氯甲烷、甲苯、乙腈为溶剂，反应 10.5h，生成达格列净杂质23

参考文献：

名称：

达格列净释放一氧化氮的潜在抗糖尿病和抗血栓形成剂的设计，合成和生物学评价

摘要：

心血管并发症在2型糖尿病（T2DM）中非常普遍，甚至在T2DM的早期阶段或强化血糖控制状态下也是如此。因此，迫切需要在T2DM中干预心血管并发症。本文中，设计了NO供体和SGLT2抑制剂的新杂种以获得抗高血糖和抗血栓形成的双重作用。如所预期的，优选的杂种2表现出中等的SGLT2抑制作用和抗血小板聚集活性，并且在NO清除剂的存在下也证实了其由NO介导的抗血小板作用。此外，化合物2在小鼠的口服葡萄糖耐量试验中发现了显着的降血糖作用和尿葡萄糖排泄。潜在的多功能复合物（例如化合物2）有望作为干预T2DM中心血管并发症的潜在候选药物。

DOI：

10.1016/j.bmc.2018.06.017

点击查看最新优质反应信息

文献信息

ARYL GLYCOSIDE COMPOUND, PREPARATION METHOD AND USE THEREOF

申请人：Xu Zusheng

公开号：US20130324464A1

公开（公告）日：2013-12-05

Disclosed are an aryl glycoside compound as represented by formula I or formular I′, a pharmaceutically acceptable salt thereof, optical isomer thereof or a prodrug thereof. The present invention relates to a method of preparing said aryl glycoside compound and the use thereof The aryl glycoside compound of the present invention has an excellent ability on inhibit SGLT activity, especially SGLT2 activity, and is diabetes-fighting medicine with great potential.

公开了一种由化学式I或化学式I'表示的芳基糖苷化合物，其药学上可接受的盐，其光学异构体或其前药。本发明涉及一种制备所述芳基糖苷化合物的方法及其用途。本发明的芳基糖苷化合物具有出色的抑制SGLT活性，特别是SGLT2活性的能力，是具有巨大潜力的抗糖尿病药物。
[EN] GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS<br/>[FR] DÉRIVÉS DE GLUCOPYRANOSE UTILES EN TANT QU'INHIBITEURS DE SGLT2

申请人：JANSSEN PHARMACEUTICA NV

公开号：WO2020084559A1

公开（公告）日：2020-04-30

The present invention is directed to glucopyranose derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

本发明涉及式(I)的葡萄糖吡喃糖衍生物，含有它们的药物组合物以及它们在治疗由SGLT2活性调节的疾病和症状中的应用。更具体地，本发明的化合物在治疗例如II型糖尿病、X综合征以及与这些疾病相关的并发症和症状方面是有用的。
D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture

申请人：Eckhardt Matthias

公开号：US20060009400A1

公开（公告）日：2006-01-12

A D-Xylopyranosyl-substituted phenyl compound of general formula I wherein the groups R 1 to R 5 , X, Z and R 7a , R 7b , R 7c are defined as in claim 1, have an inhibiting effect on the sodium-dependent glucose cotransporter SGLT. The present invention also relates to pharmaceutical compositions for the treatment of metabolic disorders.

一般公式I中的A D-吡喃木糖基取代的苯基化合物其中，R1至R5、X、Z以及R7a、R7b、R7c的定义如权利要求1所述，对钠依赖性葡萄糖共转运体SGLT具有抑制作用。本发明还涉及用于治疗代谢性疾病的药物组合物。
[EN] THE PRESENT INVENTION RELATES TO PROCESS FOR THE PREPARATION OF D-GLUCITOL, 1,5- ANHYDRO-1-C-[4-CHLORO-3-[[4-[[(3S)-TETRAHYDRO-3-FURANYL] OXY]PHENYL] METHYL]PHENYL]-, (1S) AND ITS CRYSTALLINE FORMS THEREOF.<br/>[FR] PROCÉDÉ DE PRÉPARATION DE D-GLUCITOL, 1,5- ANHYDRO-1-C-[4-CHLORO-3-[[4-[[(3S)-TÉTRAHYDRO-3-FURANYL] OXY]PHÉNYL] MÉTHYL]PHÉNYL]-, (1S) ET SES FORMES CRISTALLINES

申请人：MSN LABORATORIES PRIVATE LTD

公开号：WO2017130217A1

公开（公告）日：2017-08-03

The present invention relates to process for the preparation of D-glucitol, 1,5- anhydro-l-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl] methyl]phenyl]-, (1S) formula- 1 and its crystalline forms thereof.

本发明涉及一种制备D-葡萄糖醇、1,5-脱水-L-C-[4-氯-3-[[4-[(3S)-四氢-3-呋喃基氧基]苯基]甲基]苯基]-（1S）式-1及其晶体形式的方法。
Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof

申请人：Emmennar Pharma Private Limited

公开号：US20180346502A1

公开（公告）日：2018-12-06

The present invention relates to novel, improved processes for the preparation of sodium glucose co-transporter 2 (SGLT-2) inhibitors and novel intermediates thereof. More particularly, the present invention relates to a novel, improved process for the preparation of gliflozin compounds such as empagliflozin and dapagliflozin, intermediates thereof. The product obtained from the processes of present invention may be amorphous or crystalline, or in the form of amorphous/crystalline solid dispersions/solutions with pharmaceutically acceptable polymers and preparation process thereof. Also, the products obtained from the present invention may be used for the preparation of medicaments for the prevention and/or treatment of diseases and conditions associated with SGLT-2 inhibition.

本发明涉及一种新颖的、改进的制备葡萄糖钠共转运蛋白2（SGLT-2）抑制剂及其新颖中间体的方法。更具体地说，本发明涉及一种新颖的、改进的用于制备格列列醇类化合物如恩帕格列醇和达帕格列醇及其中间体的方法。本发明的方法得到的产品可能是非晶态或结晶态，或者以非晶态/结晶态固体分散体/溶液的形式与药用可接受聚合物一起制备。此外，本发明得到的产品可用于制备用于预防和/或治疗与SGLT-2抑制相关的疾病和症状的药物。

达格列净杂质23 | 1079083-63-8

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