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Glucoside derivate

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

Active Publication Date: 2015-01-14
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 increasing renal glucose excretion induces a net energy deficit, promotes weight loss and indirectly improves obesity symptoms

Method used

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  • Glucoside derivate
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Examples

Experimental program
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preparation example Construction

[0129] The preparation method of the compound of the general formula (I) of the present invention includes making the compound represented by the general formula (IV), its pharmaceutically acceptable salt, its easily hydrolyzable ester or its isomer, and the compound represented by the general formula (V) , Its pharmaceutically acceptable salt, its easily hydrolyzable ester or its isomer undergoes a nucleophilic reaction,

[0130]

[0131] Where 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 route is:

[0134]

[0135]

[0136] Reaction steps:

[0137] Step 1 Preparation of compound a

[0138] Dissolve raw material 1 and N-methylmorpholine in THF, cool...

Embodiment 2

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

[0210]

[0211] Referring to Example 1, 4.35 g of compound β-1'-deoxy-1'-(4-sulfonamido-3-(p-ethoxybenzyl)benzene)-glucose acetal was obtained, and the yield was 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 (10g, 42.64mmol) was dissolved in 20mL of dichloroethane, oxalyl chloride (5g, 40mmol) 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 trichloride (6.24g, 51.17mmol) was added, cooled in an ice-water bath, and ethoxybenzene (6.83g, 51.17mmol) was slowly added dropwise. After the completion of stirring at room temperature overnight, the reaction solution was poured into 20 mL of ice-water mixture for liquid separation, the aqueous phase was extracted once with dichloromethane, the combined organic phase was washed with water and saturated sodium ch...

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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 methods for preparing these compounds and their intermediates. Specifically, it relates to glycoside derivatives as inhibitors of sodium-glucose cotransporter (SGLT), 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), as well as 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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