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A new type of sulfonic acid derivative, its preparation method and its use as medicine

A technology of medicine and medicinal salt, which is applied in the field of preparation of medicines for treating diabetes and metabolic syndrome, and can solve problems such as hypoglycemia and weight gain, side effects of edema, side effects, etc.

Active Publication Date: 2019-02-01
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing methods for the treatment of diabetes all have certain defects.
Examples include insulin injections and sulfonylureas, which may cause hypoglycemia and weight gain; metformin, alpha-glucosidase inhibitors, and GLP-1 analogs, which may cause gastrointestinal side effects; PPAR-γ agonists, which may cause weight gain and edema side effects; DPP-IV inhibitors may cause suprapharyngitis, headache and infection side effects

Method used

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  • A new type of sulfonic acid derivative, its preparation method and its use as medicine
  • A new type of sulfonic acid derivative, its preparation method and its use as medicine
  • A new type of sulfonic acid derivative, its preparation method and its use as medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] Methyl 2((4-hydroxyphenyl)sulfonyl)acetic acid

[0128]

[0129] The first step: 4-methoxythiophenol (0.88ml, 7.13mmol) was dissolved in 15ml of acetonitrile, potassium carbonate (2.96g, 21.4mmol) was added, the resulting mixture was cooled in an ice bath, and bromine was added dropwise Ethyl acetate (1.03ml, 9.27mmol) in acetonitrile solution (5ml), during the dropwise addition, the internal temperature was controlled to be lower than 0°C. After the dropwise addition, the resulting brown reaction solution was stirred at room temperature for 3 hours. After the reaction was complete as detected by TLC, add 30ml of water to dilute , extracted with ethyl acetate (30ml×4), the combined organic phases were washed successively with 1N NaOH (20ml×1), 1N HCl (20ml×1), saturated NaCl solution (20ml×2), and the resulting organic phase was washed with anhydrous sodium sulfate After drying and suction filtration, the filtrate was evaporated to remove the solvent under reduced pr...

Embodiment 2

[0134] Methyl 1-((4-((4'-methoxy-2',6'-dimethyl-[1,1'-biphenyl]-3-yl)methoxy)phenyl)sulfonyl ) Methyl cyclopropyl-1-acetate

[0135]

[0136] The raw material (0.2g, 0.44mmol) was dissolved in 10ml of DMF, potassium carbonate (0.15g, 1.1mmol) and a catalytic amount of TEBA were added, and after stirring at room temperature for 15min, 1,2-dibromoethane (0.10g, 0.55 mmol), the resulting reaction solution was heated at 60°C for 3 h. After the reaction was complete as detected by TLC, the reaction solution was cooled to room temperature, diluted with 30 ml of water, extracted with ethyl acetate (30 ml × 4), and the combined organic phase was washed with saturated NaCl solution (20 ml × 4). 2) Washing, the resulting organic phase was dried with anhydrous sodium sulfate, suction filtered, the filtrate was evaporated to remove the solvent under reduced pressure, and the residue was purified by column chromatography (petroleum ether / ethyl acetate, 85:25, v / v) to obtain a white solid ...

Embodiment 3

[0138] 2′-Chloro-[1,1′-biphenyl]-4-carbaldehyde

[0139]

[0140] Material III-1 (0.5g, 2.6mmol) was dissolved in 42ml mixed solvent (toluene / ethanol / water, 3:1:3, v / v / v), and material III-2 (0.3g, 2.6mmol) was added, Triphenylphosphopalladium (0.15g, 0.13mmol) and anhydrous sodium carbonate (0.69g, 6.5mmol) were heated at 60°C for 24h under nitrogen protection. After the reaction, cool to room temperature, dilute with 20ml of water, use diatomaceous earth as a pad for suction filtration, wash the filter cake with ethyl acetate (15ml×3), extract the filtrate with ethyl acetate (30ml×4), combine the organic phases with saturated NaCl solution (20ml×2), the obtained organic phase was dried over anhydrous sodium sulfate, suction filtered, the filtrate was evaporated to remove the solvent under reduced pressure, and the residue was subjected to column chromatography (petroleum ether / ethyl acetate, 70:30, v / v) Purification afforded 0.47 g of off-white solid with a yield of 84%....

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Abstract

The invention relates to a novel sulphone acid derivative show in a formula (I), a preparation method thereof and application of a medicine composition containing the derivative in preparing medicines for treating diabetes and metabolic syndrome. The sulphone acid derivative has excellent in-vivo blood glucose decreasing activity, and can be used for preventing or treating diabetes. (The formula is shown in the description).

Description

technical field [0001] The invention relates to the field of pharmacology related to diabetes, in particular to a novel sulfonic acid derivative, its preparation method and the application of a pharmaceutical composition containing the derivative in the preparation of medicines for treating diabetes and metabolic syndrome. The structure of the sulfonic acid derivative involved in the present invention has uniqueness and novelty in structural modification of this type of compound, and exhibits excellent drug safety. Background technique [0002] Diabetes is a group of metabolic diseases characterized by hyperglycemia, which is divided into type 1 diabetes (insulin-dependent diabetes) and type 2 diabetes (non-insulin-dependent diabetes). At present, about 415 million people in the world suffer from diabetes, and another 318 million people are potentially at high risk of diabetes. Diabetes patients in China are 109.6 million, ranking first in the world, and type 2 diabetes pat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/44C07C315/04C07D277/24C07D261/08C07D207/325A61K31/192A61K31/277A61K31/426A61K31/42A61K31/402A61P3/10A61P3/00
CPCC07C317/44C07D207/325C07D261/08C07D277/24
Inventor 黄文龙钱海刘春霞
Owner CHINA PHARM UNIV
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