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Compound with glucose-reducing and lipid-regulating effects as well as preparation and application thereof

A compound and lipid-regulating technology, applied in the field of medicine and drugs for metabolic diseases of glucose and lipids, can solve problems such as single action, and achieve the effects of improving insulin resistance, excellent in vivo hypoglycemic and lipid-regulating activity, and broad development prospects.

Active Publication Date: 2021-03-12
YUNNAN SECOND PEOPLES HOSPITAL +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of drug treatment of metabolic syndrome, the hypoglycemic drugs or lipid-lowering drugs currently used in clinical practice have a single effect, and none of them have an ideal effect on improving various pathological indicators of metabolic syndrome. Metabolic syndrome drug research is underway to bring new, safer and more effective drugs to patients with metabolic syndrome

Method used

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  • Compound with glucose-reducing and lipid-regulating effects as well as preparation and application thereof
  • Compound with glucose-reducing and lipid-regulating effects as well as preparation and application thereof
  • Compound with glucose-reducing and lipid-regulating effects as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (6-Hydroxy-1-benzofuran-3-yl)methyl acetate

[0022]

[0023] Ethyl 4-chloroacetoacetate (4.25 ml, 31.43 mmol) was dissolved in 20 ml of concentrated sulfuric acid at 0 °C, and the resulting pale yellow viscous solution was cooled to about -5 °C in an ice bath, and m-benzene was added in batches Diphenol (3.15 g, 28.57mmol), control the internal temperature below 0 °C, after the addition is complete, stir at room temperature for 2 h, the reaction solution is poured into 50ml of ice water, a white solid is precipitated, suction filtered, washed with water (5 ml × 2) The filter cake was dried to obtain 5.6 g of off-white solid, and the crude product yield was 82.3%.

[0024] Take the above crude product (2 g, 9.50 mmol) in a 200 ml single-necked bottle, add 1N NaOH solution (100 ml), the solution immediately turns into a thick yellow, and the above solution is placed in an oil bath and heated to reflux for 2 h. After the reaction is complete, cool to At room temperatu...

Embodiment 2

[0027] (6-Hydroxy-2,3-dihydro-1-benzofuran-3-yl)methyl acetate

[0028]

[0029] Dissolve the raw material ester (2 g, 9.7 mmol) in methanol, add a catalytic amount of palladium carbon 0.2 g, replace it with hydrogen three times, pass in hydrogen and stir at room temperature for 24 h. Cake, and the filtrate was evaporated to remove the solvent under reduced pressure to obtain 1.93 g of off-white powdery solid, with a yield of 95.5%.

[0030] 1 H NMR (300 MHz, CDCl 3 ) δ : 6.97 (d, J = 8.71 Hz, 1H, ArH), 6.31–6.34(m, 2H, ArH), 4.82 (brs, 1H, ArOH), 4.75 (t, J = 9.10 Hz, 1H, -OCH 2 ), 4.26,4.24 (dd, J =5.72, 9.10 Hz, 1H, -OCH 2 ), 3.74–3.84 (m, 1H, ArCH), 3.72 (s, 3H,-OCH 3 ), 2.74, 2.69 (dd, J = 5.72, 16.41 Hz, 1H, -COCH 2 ), 2.55, 2.50 (dd, J =9.11, 16.41 Hz, 1H, -COCH 2 ).

Embodiment 3

[0032] (E)-2-(6-(((3,7-Dimethyloctyl-2,6-dien-1-yl)oxy)-2,3-dihydrobenzofuran-3-yl ) acetic acid (I)

[0033]

[0034] Geraniol (1 g, 6.5 mmol) was added in batches to a pre-cooled 5 ml thionyl chloride solution in dichloromethane under an ice bath, stirred evenly and heated to reflux for 1 h, and the reaction solution was evaporated under reduced pressure to remove excess Thionyl chloride, the resulting brown oil was dissolved in 20 ml THF, added raw material ester (1 equivalent), anhydrous potassium carbonate (3 equivalents), catalytic amount KI, heated to 60 ° C for 8 h, filtered, and reduced pressure The solvent was evaporated, the residue was dissolved in 30 ml of water, extracted with ethyl acetate (20 ml × 3), the organic phases were combined, washed with saturated brine (15 ml × 2), dried over anhydrous sodium sulfate, filtered, and the filtrate was decompressed The solvent was evaporated, and the residue was purified by column chromatography (petroleum ether / ethyl a...

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Abstract

The invention discloses a compound with glucose-reducing and lipid-regulating effects as well as a preparation and application thereof. The compound with glucose-reducing and lipid-regulating effectsis a compound with structures as shown in a formula I and a formula II and a pharmaceutically acceptable salt, wherein the structures as shown in the formula I and the formula II are specifically shown in the specification. The preparation is a tablet, a capsule, powder, a pill or an injection prepared by adding pharmaceutically acceptable auxiliary materials into the compound with the glucose-reducing and lipid-regulating effects. The application is the application of the compound with the glucose-reducing and lipid-regulating effects in preparing an FFA1 / PPARdelta dual agonist. The application is the application of the compound with the glucose-reducing and lipid-regulating effects in preparation of drugs for preventing and / or treating glucose metabolic disorder and / or lipid metabolic disorder diseases. The compound and the medicinal salt thereof can be potentially used for treating or preventing diabetes, hyperlipidemia, fatty liver and other related metabolic syndromes, and have wide development prospects.

Description

technical field [0001] The present invention belongs to the technical field of medicine, and further belongs to the technical field of drugs for glucose and lipid metabolism diseases, and specifically relates to a compound with hypoglycemic and lipid-lowering effects and its preparation and application. Background technique [0002] Metabolic syndrome is a common disease characterized by abnormal glucose and lipid metabolism, accompanied by elevated low-density lipoprotein and low high-density lipoprotein cholesterol. The common symptoms are obesity, diabetes, hyperlipidemia, atherosclerosis Cirrhosis and fatty liver, etc. Among them, diabetic patients often have hyperlipidemia, cardiovascular disease, diabetic nephropathy, diabetic neuropathy and other diseases. According to the World Health Organization, more than 220 million people worldwide suffer from diabetes. Among them, China has become the country with the largest number of diabetics in the world, with more than 92 ...

Claims

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Application Information

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IPC IPC(8): C07D307/79A61K31/343A61P3/10A61P3/06A61P3/08A61P3/04A61P13/12A61P9/10A61P1/16
CPCC07D307/79A61P3/10A61P3/06A61P3/08A61P3/04A61P13/12A61P9/10A61P1/16
Inventor 杨莹李政耿新倩杨克李奕平周太成
Owner YUNNAN SECOND PEOPLES HOSPITAL
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