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Sulfonamide compound and preparation method as well as application thereof

A compound, sulfonamide technology, applied in the field of medicine, can solve the problems of inability to maintain long-term efficacy, weight gain, hypoglycemia, etc.

Inactive Publication Date: 2013-04-03
TIANJIN UNIV OF COMMERCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have a good curative effect, but there are still disadvantages that the long-term use of the drug can not maintain the long-term curative effect, and it is easy to cause many adverse reactions such as hypoglycemia, weight gain, and liver toxicity.

Method used

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  • Sulfonamide compound and preparation method as well as application thereof
  • Sulfonamide compound and preparation method as well as application thereof
  • Sulfonamide compound and preparation method as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the preparation of intermediate III

[0047] Take intermediate Ⅲ-1 as an example

[0048]

[0049]Add 2-(piperazin-1-yl)benzothiazole (2.19g, 0.01mol), 3-chloropropylamine (1.2g, 0.015mol) and sodium hydroxide into a reaction flask equipped with stirring, condenser and thermometer (7.2g, 0.18mol), dissolved in DMF (30ml), and reacted at 50°C for 4h. Naturally cool to room temperature, filter, add potassium acetate (0.24g) to the filtrate, vacuum distill about 25mL of DMF, add 50mL of water to the residue for dilution, adjust the pH value to 4.6 with acetic acid, dichloromethane extraction, the water layer with 12 % ammonia solution to adjust the pH value to 9.5, then extracted twice with dichloromethane, 50mL each time, dried over anhydrous sodium sulfate, and evaporated the solvent to obtain a yellow oily product as intermediate Ⅲ-1, HPLC: 92%, HRMS (m / z): 263.1325.

[0050] The compound can be conveniently prepared by referring to the method of Exa...

Embodiment 2

[0054] Preparation of N-(2-(4-(benzothiazol-2-yl)piperazin-1-yl)ethyl)-3,5-dimethylbenzenesulfonamide (compound Ⅰ-1):

[0055]

[0056] Add 2.46g (0.01mol) of the intermediate III-1 prepared in Example 1 into a reaction flask equipped with stirring, condenser and thermometer, dissolve it with 10mL of dichloromethane, stir, and add 2.2g of anhydrous potassium carbonate , add 2.1g (0.01mol) of 3,5-dimethylphenyl-1-sulfonyl chloride dropwise under ice-bath conditions, after dropping, stir at room temperature for about 3h, TLC detects that the reaction is complete, filter the solid, and wash the filtrate three times with water , water 15mL each time, the organic layer was fully dried with anhydrous sodium sulfate, filtered, and the organic solvent was evaporated under reduced pressure to obtain a light yellow oil. The white solid product obtained by silica gel column chromatography was compound Ⅰ-1 (HPLC: 99.5%) . Melting point 161°C-162.1°C, HRMS (m / z): 431.1570.

[0057] Co...

Embodiment 3

[0066] Formation of compound I-10 into hydrochloride: take 2.0 g of the white solid product of compound I-10 and dissolve it in 10 mL of anhydrous ether. Cool in an ice-water bath to 0°C, add dropwise 25% diethyl ether solution of hydrochloric acid until the pH value is 2, and continue to stir for about 1 h in an ice-water bath. After filtration, a white solid was obtained, which was the hydrochloride of compound Ⅰ-10.

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Abstract

The invention discloses a sulfonamide compound and a preparation method as well as application thereof, and provides the sulfonamide compound with hypoglycemic activity and the preparation method thereof. The sulfonamide compound has a structure of a general formula I, wherein X is S or O atoms, n is 1, 2, 3 or 4, R1 and R2 are simultaneously or respectively hydrogen or C1-C4 alkyl groups, and R3, R4 and R5 are simultaneously or respectively one out of hydrogen, C1-C6 alkyl groups, C1-C4 alkoxyl groups, halogens, single or multi-halogen replaced C1-C4 alkyl groups, cyan, phenyl groups, single halogenated phenyl groups, C1-C4 alkoxyl phenyl group, C1-C4 alkyl sulfonyl groups and bromomethyl carbonyl groups. The sulfonamide compound with the structure of the formula I and pharmaceutically acceptable salts thereof have obvious effect in terms of resisting hyperglycemia.

Description

technical field [0001] The invention belongs to the technical field of medicine, and more specifically, relates to a class of compounds with hypoglycemic effect, their preparation method and application. Background technique [0002] According to the data and estimates of diabetes and impaired glucose tolerance (IGT) released by the International Diabetes Federation (IDF), the number of diabetic patients in 2003 was 194 million, and it will reach 333 million in 2025; It will be as high as 472 million. In recent years, with the continuous improvement of people's living standards and changes in dietary structure, the number of diabetic patients in my country has also experienced a large-scale increase. [0003] The anti-diabetic drugs currently in clinical use mainly include insulin, sulfonylurea, metformin, and recently listed α-glucosidase inhibitors and insulin sensitizers such as thiazolidinedione drugs. These drugs have a good curative effect, but there are still disadv...

Claims

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Application Information

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IPC IPC(8): C07D277/82C07D263/58C07D417/04C07D413/04A61K31/496A61P3/10
Inventor 梁艳书朱英杰郭桂梅路亮龙丽
Owner TIANJIN UNIV OF COMMERCE
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