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Novel oxime ether derivative and preparation method thereof and application of derivative by serving as drug

A compound, alkoxy technology, applied in the field of preparation of drugs for the treatment of diabetes and metabolic syndrome, can solve problems such as side effects, weight gain, edema side effects, etc.

Inactive Publication Date: 2016-05-11
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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  • Novel oxime ether derivative and preparation method thereof and application of derivative by serving as drug
  • Novel oxime ether derivative and preparation method thereof and application of derivative by serving as drug
  • Novel oxime ether derivative and preparation method thereof and application of derivative by serving as drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] (6-Hydroxy-1-benzofuran-3-yl)methyl acetate

[0094]

[0095] Ethyl 4-chloroacetoacetate (4.25ml, 31.43mmol) was dissolved in 20ml of concentrated sulfuric acid at 0°C, and the formed pale yellow viscous solution was cooled to about -5°C in an ice bath, and resorcinol ( 3.15g, 28.57mmol), the internal temperature was controlled below 0°C, the addition was completed, stirred at room temperature for 2h, the reaction solution was poured into 50ml of ice water, a white solid precipitated, suction filtered, washed with water (5ml×2) filter cake, and dried to obtain rice White solid 5.6g, crude product yield 82%.

[0096] Take the above crude product (2g, 9.50mmol) in a 200ml single-necked bottle, add 1N NaOH solution (100ml), the solution immediately becomes thick yellow, the above solution is placed in an oil bath and heated to reflux for 2h, after the reaction is complete, cool to room temperature, and Adjust the pH to 2-3 with sulfuric acid, extract the resulting solu...

Embodiment 2

[0099] (6-Hydroxy-2,3-dihydro-1-benzofuran-3-yl)methyl acetate (IV)

[0100]

[0101] The raw material ester (2g, 9.71mmol) was dissolved in methanol, and a catalytic amount of palladium-carbon 0.2g was added, replaced with hydrogen three times, and stirred at room temperature for 24 hours by introducing hydrogen gas. The solvent was evaporated from the filtrate under reduced pressure to obtain 1.93 g of off-white powdery solid, with a yield of 95%.

[0102] 1 HNMR (300MHz, CDCl 3 )δ: 6.97 (d, J = 8.71Hz, 1H, ArH), 6.31-6.34 (m, 2H, ArH), 4.82 (brs, 1H, ArOH), 4.75 (t, J = 9.10Hz, 1H, -OCH 2 ), 4.26, 4.24 (dd, J=5.72, 9.10Hz, 1H, -OCH 2 ), 3.74-3.84 (m, 1H, ArCH), 3.72 (s, 3H, -OCH 3 ), 2.74, 2.69 (dd, J=5.72, 16.41Hz, 1H, -COCH 2 ), 2.55, 2.50 (dd, J=9.11, 16.41Hz, 1H, -COCH 2 ).

Embodiment 3

[0104] 2-(6-(4-(2-methoxyimino-2-phenethoxy)benzyloxy)-2,3-dihydro-1-benzofuran-3-yl)acetic acid (I- 1)

[0105]

[0106] Step 1: Dissolve 2-bromoacetophenone (0.7g, 3.52mmol) in 15ml of DMSO, add methoxylamine hydrochloride (0.4g, 5.28mmol), after the addition is complete, stir at room temperature for 5h, add 150ml of water to dilute, Extracted with ethyl acetate (30ml×3), combined the organic phases, washed with saturated brine (15ml×2), dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled off the solvent under reduced pressure to obtain 0.8g of a yellow-brown oil, which was used directly react in the next step.

[0107] Second step: get above-mentioned oily product (0.8g, 3.52mmol) and dissolve in 25ml acetonitrile, add potassium carbonate (1.46g, 10.56mmol) successively, 4-hydroxybenzyl alcohol (0.44g, 3.52mmol), the above-mentioned mixture is heated for 65 Reaction at ℃ for 8 hours, suction filtration, the filtrate was evaporated to remove th...

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Abstract

The invention relates to a novel oxime ether derivative shown as a general formula (I) (please see the formula in the description) and a preparation method thereof and application of a pharmaceutical composition containing the derivative in preparation of a drug for treating diabetes and a metabolic syndrome. The oxime ether derivative has the excellent in-vivo hypoglycemic activity and can be used for preventing or treating the diabetes.

Description

technical field [0001] The invention relates to the field of pharmacology related to diabetes, in particular to a novel oxime ether 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 structures of the oxime ether derivatives involved in the present invention are unique and novel in structural modification of this type of compounds. Background technique [0002] Diabetes is a disease of energy metabolism and is divided into type 1 diabetes (insulin-dependent diabetes) and type 2 diabetes (non-insulin-dependent diabetes). At present, there are about 366 million diabetic patients in the world, accounting for 6.4% of the world's population, and type 2 diabetic patients account for about 90-95% of the total number of diabetic patients. [0003] Diabetes can be treated with diet and exercise. When these do not relieve symptoms, medical t...

Claims

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Application Information

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IPC IPC(8): C07D307/83A61K31/343A61P3/10A61P3/00
CPCC07D307/83
Inventor 黄文龙钱海李政杨建勇苏欣潘渺博
Owner CHINA PHARM UNIV
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