Glucoside derivate

A compound and alkyl technology, applied in the field of medicine, can solve problems such as insufficient net energy

Active Publication Date: 2012-12-19
SHANDONG XUANZHU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this pathway does not directly contribute to the pathophysiology of type 2 diabetes, lowering blood glucose by inc

Method used

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Examples

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preparation example Construction

[0129] The preparation method of the compound of the general formula (I) of the present invention comprises making the compound shown in the general formula (IV), its pharmaceutically acceptable salt, its easily hydrolyzed ester or its isomer, and the compound shown in the general formula (V) , its pharmaceutically acceptable salt, its easily hydrolyzed ester or its isomer undergoes a nucleophilic reaction,

[0130]

[0131] Among them, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 7a , R 7b , R 7c , X, n and A are as defined above.

[0132] The above-mentioned compounds of the present invention can be synthesized by the methods described in the following schemes and / or other techniques known to those of ordinary skill in the art, but are not limited to the following methods.

[0133] When X is methylene, the reaction scheme is:

[0134]

[0135]

[0136] Reaction steps:

[0137] The preparation of step 1 compound a

[0138] Dissolve raw material 1 and N-me...

Embodiment 2

[0209] Example 2 Preparation of β-1'-deoxy-1'-(4-sulfonamido-3-(p-ethoxybenzyl)benzene)-glucose acetal (compound 2) prepare

[0210]

[0211] Reference Example 1 obtained 4.35 g of the compound β-1'-deoxy-1'-(4-sulfonamido-3-(p-ethoxybenzyl)benzene)-glucose acetal with a yield of 93%.

[0212] Molecular formula: C 21 h 27 NO 8 S molecular weight: 453.15LC-MS(M+H) + :454

Embodiment 3

[0213] Example 3 β-1'-deoxy-1'-(4-sulfonylmethylamino-3-(p-ethoxybenzyl)benzene)-glucose acetal (compound 3) preparation

[0214]

[0215] Step 1 Preparation of (5-bromo-2-chlorophenyl) (4-ethoxyphenyl) ketone

[0216]

[0217] 5-Bromo-2-chlorobenzoic acid (10 g, 42.64 mmol) was dissolved in 20 mL of dichloroethane, and oxalyl chloride (5 g, 40 mmol) was added dropwise within 30 minutes, and stirring was continued for 30 minutes after completion. Then the solvent was removed by rotary evaporation as much as possible, the residue was dissolved in 30mL of dichloromethane, aluminum chloride (6.24g, 51.17mmol) was added, cooled in an ice-water bath, and ethoxybenzene (6.83g, 51.17mmol) was slowly added dropwise, After completion, stir overnight at room temperature, then pour the reaction solution into 20 mL of ice-water mixture, separate the layers, extract the aqueous phase once with dichloromethane, wash the combined organic phase with water and saturated sodium chlori...

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Abstract

The invention belongs to the field of medical technology, and particularly relates to a glucoside derivate shown as a formula (I), and a medically acceptable salt, an ester easily hydrolyzed, a stereoisomer and an itnemrediate of the glucoside derivate, and a preparation method of the compounds and the intermediate, in particular to a glucoside derivate which is served as a sodium-glucose co-transporter (SGLT) inhibitor, a medically acceptable salt, an ester easily hydrolyzed, a stereoisomer and an itnemrediate of the glucoside derivate, and a preparation method of the compounds and the intermediate. The glucoside derivate provided by the invention can be used for treating diabetes mellitus such as insulin dependent diabetes mellitus (I type diabetes mellitus) and non-insulin dependent diabetes mellitus (II type diabetes mellitus), and also can be applied to treating insulin resistance diseases and various diseases relevant to diabetes mellitus of fat, and preventing such diseases, wherein R1, R2, R3, R4, R5, R6, R7, R7a, R7b, R7c, X, n and A are defined as shown in the specification.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and relates to glycoside derivatives, their pharmaceutically acceptable salts, their easily hydrolyzed esters, their isomers and intermediates, and the preparation methods of these compounds and their intermediates. Specifically relates to glycoside derivatives as sodium-glucose cotransporter (SGLT) inhibitors, their pharmaceutically acceptable salts, their easily hydrolyzed esters, their isomers and intermediates, and the preparation of these compounds and their intermediates method. The glycoside derivatives of the present invention can be used for diabetes such as insulin-dependent diabetes (type I diabetes) and non-insulin-dependent diabetes (type II diabetes), and various diabetes including insulin resistance diseases and obesity Treatment of related diseases, and prevention of these diseases. 2. Background technology [0002] Approximately 100 million people worldwide suffer from type...

Claims

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Application Information

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IPC IPC(8): C07D309/10C07D407/12C07D409/10A61K31/351A61K31/381A61P3/10
Inventor 吴永谦松山皓治
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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