Sulpho-glucosan derivative and preparation method and application thereof

A glucopyranoside and thiol technology, which can be used in sugar derivatives, metabolic diseases, drug combinations, etc., and can solve problems such as hepatotoxicity and body weight

Inactive Publication Date: 2009-06-03
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have good therapeutic effects, but there are safety problems in long-term treatment, such as: liver toxicity and weight gain, etc.

Method used

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  • Sulpho-glucosan derivative and preparation method and application thereof
  • Sulpho-glucosan derivative and preparation method and application thereof
  • Sulpho-glucosan derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Phenoxyacetylhydrazide (V-1)

[0039]

[0040] 18.0 g (0.1 mol) of compound IV-1 and 250 mL of absolute ethanol were added to a 500 mL round bottom flask, and 30 g (0.51 mol) of 85% hydrazine hydrate was added with stirring at room temperature. The reaction mixture was then warmed to reflux for 1 hour. After cooling to room temperature, the reaction system was concentrated to half of its original volume on a rotary evaporator, then stirred at room temperature for 1 hour, the crystals were collected by suction filtration, and compound V-1 was obtained after drying. Colorless crystals, 14.8g, yield 89%.

[0041] Compounds IV-1 and V-1 are one of the compounds having general formula IV and one having general formula IV, respectively.

Embodiment 2-10

[0043] With the operation of Example 1, replace Compound IV-1 in Example 1 with Compound IV-2 to IV-10 in the following table, and all the other operations are the same as Example 1 to obtain Compounds V-2 to V listed in the following table -5.

[0044] Compounds IV-2 to IV-10 and compounds V-2 to V-10 belong to two classes of compounds having general formula IV and having general formula V, respectively.

[0045] Example

Embodiment 11

[0047] 2-Mercapto-5-(phenoxymethyl)-1,3,4-thiadiazole (II-a-1)

[0048]

[0049] Add 4.98g (30mmol) compound V-1 and 100mL absolute ethanol to a 250mL round bottom flask, add 2.24g (40mmol) solid KOH under stirring at room temperature, stir at room temperature for 10 minutes, then dropwise add 3.80g (50mmol) to dissolve in 10 mL of absolute ethanol for dry CS 2After completion, the reaction system was stirred overnight at room temperature. A yellow solid was obtained by suction filtration, and dried to obtain compound VI-1 as a yellow solid. The obtained compound VI-1 was dissolved in 20 mL of concentrated sulfuric acid at room temperature, followed by stirring overnight at room temperature. The reaction system was poured into 200 mL of ice water, stirred for 10 minutes, suction filtered, and the filter cake was washed with water and dried to obtain 5.44 g of compound II-a-1, with a yield of 81%. IR(KBr), 3030, 1498, 1588, 1200cm -1 .

[0050] Compound VI-1 and compoun...

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PUM

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Abstract

The invention relates to the field of diabetes related medicine, in particular to a depressor for a Na-glucose transporter II containing a structure of sulpho-glucose (SGLT2) and a preparation method thereof, and a pharmaceutical composition containing SGLT2 and an application thereof in the preparation of diabetes drugs, wherein, a radical group is defined in the specification.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a sodium glucose transporter type 2 (SGLT2) inhibitor containing a glucosinolate structure, which has a therapeutic effect on diabetes, a preparation method thereof, and a pharmaceutical composition containing them. Background technique [0002] There are currently about 170 million diabetics in the world, and the vast majority of them are type II (ie, non-insulin-dependent) diabetics. The antidiabetic drugs currently in clinical use mainly include metformin, sulfonylureas and insulin drugs. In recent years, thiazolidinedione drugs, α-glucosidase inhibitors and dipeptidyl peptidase-IV have also been listed on the market. Inhibitors etc. These drugs have good therapeutic effects, but there are safety problems in long-term treatment, such as liver toxicity and weight gain. [0003] Sodium glucose transporter type 2 (SGLT2) is a new target...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00A61K31/7056A61P3/10
Inventor 赵桂龙徐为人王玉丽汤立达王致峰邹美香刘巍张士俊谭初兵刘冰妮
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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