Beta-amino ketones compound with anti-diabetic activity

An anti-diabetic, amino ketone technology, applied in the direction of organic active ingredients, active ingredients of heterocyclic compounds, organic chemistry, etc., can solve problems such as toxic and side effects

Inactive Publication Date: 2009-09-23
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing drugs have obvious toxic side effects

Method used

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  • Beta-amino ketones compound with anti-diabetic activity
  • Beta-amino ketones compound with anti-diabetic activity
  • Beta-amino ketones compound with anti-diabetic activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0473] Example 1, Ydcm230: 4-(3-(4-chlorophenyl)-3-oxo-1-m-tolylamino)benzenesulfonamide

[0474] 12.00 grams (100 mmol) of 3-methylbenzaldehyde, 17.22 grams (100 mmol) of p-aminobenzenesulfonamide, and 150 ml of absolute ethanol were added to the reaction flask, and after stirring at room temperature for 10 minutes, 15.25 grams (100 mmol) of 4-chloroacetophenone was added. ) and a catalytic amount of concentrated hydrochloric acid, and then stirred and reacted at 30° C. for 44 hours. After the reaction, the reaction solution was cooled overnight, and the precipitated solid was filtered with suction and washed with absolute ethanol. The resulting solid was suspended in 160ml of 95% ethanol, stirred at room temperature for 2 hours, and washed with 10% K 2 CO 3 Neutralize the solution to alkaline, filter with suction, wash the filter cake with a small amount of absolute ethanol, and recrystallize the crude product from a mixed solvent of ethanol / water (volume ratio 1:1) to obt...

Embodiment 2

[0475] Example 2, Ydcm 231: 4-(3-(4-chlorophenyl)-3-oxo-1-p-chlorophenylpropylamino)benzenesulfonamide

[0476] Add 14.05 grams (100 mmol) of 4-chlorobenzaldehyde, 17.22 grams (100 mmol) of p-aminobenzenesulfonamide, and 150 ml of absolute ethanol into the reaction flask, stir at room temperature for 10 minutes, then add 15.25 grams (100 mmol) of 4-chloroacetophenone and a catalytic amount of concentrated hydrochloric acid, then stirred at 30°C for 31 hours. After the reaction, the reaction solution was cooled overnight, and the precipitated solid was filtered with suction and washed with absolute ethanol. The resulting solid was suspended in 160ml of 95% ethanol, stirred at room temperature for 2 hours, and washed with 10% K2 CO 3 Neutralize the solution to alkaline, filter with suction, wash the filter cake with a small amount of absolute ethanol, and recrystallize the crude product from a mixed solvent of ethanol / water (volume ratio 1:1) to obtain 27.61 g of crystals, with...

Embodiment 3

[0477] Example 3, Ydcm 232: 4-(3-(4-chlorophenyl)-3-oxo-1-phenylpropylamino)benzenesulfonamide

[0478] Add 10.62 grams (100 mmol) of benzaldehyde, 17.22 grams (100 mmol) of p-aminobenzenesulfonamide, and 150 ml of absolute ethanol into the reaction flask. After stirring at room temperature for 10 minutes, add 15.25 grams (100 mmol) of 4-chloroacetophenone and a catalytic amount of Concentrated hydrochloric acid, and then stirred at 30°C for 72 hours. After the reaction, the reaction solution was cooled overnight, and the precipitated solid was filtered with suction and washed with absolute ethanol. The resulting solid was suspended in 160ml of 95% ethanol, stirred at room temperature for 2 hours, and washed with 10% K 2 CO 3 Neutralize the solution to alkaline, filter with suction, wash the filter cake with a small amount of absolute ethanol, and recrystallize the crude product from a mixed solvent of ethanol / water (volume ratio 1:1) to obtain 27.61 g of crystals, with a yi...

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Abstract

The invention discloses a beta-amino ketones compound with anti-diabetic activity, particularly the compound which has the general formula (I) as shown on the right or a pharmaceutically acceptable salt thereof. The invention can increase insulin sensitivity and / or decrease postprandial blood glucose level, and prevent and delay the outbreak and the development of diabetes mellitus and complications thereof, has simple preparation method, low cost and good potential application value and can be prepared to be anti-diabetic medicine for preventing and treating the diabetes mellitus.

Description

technical field [0001] The present invention relates to organic compounds, in particular to β-aminoketone compounds with antidiabetic activity, their pharmaceutical composition and application in the field of medicine. Background technique [0002] Diabetes Mellitus (DM) is an endocrine and metabolic disease caused by a variety of reasons. The main clinical sign is high blood sugar. If it is not treated in time, it can cause damage to multiple systems in the body. In recent years, with the improvement of people's living standards, the aging population and the increase in the incidence of obesity, the incidence of diabetes has been increasing year by year, and it has become the third largest non-communicable disease in developing countries after cardiovascular diseases and tumors. , bringing a heavy burden to social and economic development. [0003] Diabetes is clinically divided into two types: Type I diabetes (insulin-dependent) is caused by the absolute shortage of insul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/39C07C229/54C07D261/14C07D239/69A61K31/63A61K31/216A61K31/42A61K31/505A61P3/10
Inventor 杨大成晏菊芳范莉陈欣许荩张蔚瑜宋小礼叶飞刘红萍蒋汉文周祖文唐雪梅张映霞李同金苏小燕
Owner SOUTHWEST UNIV
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