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Use of bis-gallate derivatives in the preparation of medicines for treating hyperuricemia

A technology of digallate and hyperuricemia, applied in the field of chemical medicine, can solve the problems of no further animal experimental data, provoking acute gout attack, large toxic and side effects of drugs, etc., achieving no toxic and side effects, reducing serum uric acid level, The effect of high safety

Active Publication Date: 2017-05-03
CATCH BIO SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Both of the above methods can reduce uric acid in the blood, and then produce curative effects on diseases such as gout, arthritis, subcutaneous gout stones, kidney stones or gouty nephropathy caused by hyperuricemia, but the side effects of the above drugs are usually relatively high. Large, for example, allopurinol can cause severe toxic side effects such as allergic reaction (morbidity rate 10-15%), hypersensitivity syndrome, myelosuppression; Probenecid, benzbromarone can stimulate gastrointestinal tract, cause kidney Side effects such as colic and acute gout attacks limit the clinical application of these drugs to a certain extent
[0005] Gallic acid is a compound that widely exists in plants. According to literature reports [Chemical World, 2009 (5), 273-276], gallic acid has a certain inhibitory activity of xanthine oxidase, but only reports that it inhibits xanthine in vitro Oxidase activity, no further animal data available

Method used

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  • Use of bis-gallate derivatives in the preparation of medicines for treating hyperuricemia
  • Use of bis-gallate derivatives in the preparation of medicines for treating hyperuricemia
  • Use of bis-gallate derivatives in the preparation of medicines for treating hyperuricemia

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Example 1: Extraction and characterization of compound 1 of the present invention

[0085] Take 5 kg of emblica medicinal material, pulverize it, and extract it with 5 L of water for 40 min while keeping it slightly boiling. The extract was concentrated to 1 L in vacuo, and the concentrated solution was separated by column chromatography using Diaion HP-20 macroporous adsorption resin, and eluted with water, 30% ethanol, 60% ethanol, and 95% ethanol respectively. Take 20 g of the eluent eluted with water and use reverse phase C18 silica gel for column chromatography separation, and use 5%-10% ethanol as the eluent for elution to obtain compound 1 of the present invention; detect and characterize it Data are as follows:

[0086] Compound 1: C 20 h 20 o 14 , molecular weight 485[M+H] +

[0087] 1 H-NMR (MeOH-d 4 ,400MHz)δ:7.12(2H,s),7.06(2H,s),5.68(1H,d),4.54(1H,dd)4.39(1H),4.01(1H,m),3.70(1H,m) ,3.53(1H,m),.3.24(1H,m); 13 C-NMR (MeOH-d 4 ,100MHz) δ:168.0,166.6...

Embodiment 2

[0088] Embodiment 2: Preparation and characterization of compound 2 of the present invention

[0089]Compound 2-8 of the present invention can be prepared by the following synthetic route:

[0090]

[0091] In this example, compound 2 of the present invention was prepared according to the following synthetic route:

[0092]

[0093] The specific operation is as follows:

[0094] (1) Synthesis of 3,4,5-tribenzylbenzoic acid

[0095] Dissolve 17.0 g of gallic acid in 800 ml of dimethylformamide (abbreviated as DMF, the same below), and use nitrogen protection, add 113 g of anhydrous potassium carbonate in batches at 25 ° C, stir for 1 hour, heat up to 40 ° C, and then Add 143ml of benzyl bromide dropwise to the reaction system within 30min; after the dropwise addition, stir the reaction mixture at 40°C for 12h; use TLC to confirm that the reaction is complete, stop heating, and lower the reaction temperature to Room temperature 25°C; add 400ml of water and 1L of ethyl a...

Embodiment 3

[0105] Embodiment 3: Preparation and characterization of compound 3 of the present invention

[0106] In this example, Compound 3 of the present invention was prepared using the same synthetic route and method as Compound 2, the only difference being that the ethylene glycol in step 3) was replaced with piperazine to obtain Compound 3 of the present invention. The detection and characterization data are as follows:

[0107] Compound 3:C 18 h 18 o 8 N 2 , molecular weight 391[M+H] +

[0108] 1 H NMR (400MHz, CD 3 OD)δ6.91(s,4H),3.45(t,4H); 13 C NMR (100MHz, CD 3 OD)δ168.1(C×2), 146.4(C×4), 137.1(C×2), 130.4(C×2), 108.7(C×4), 48.9(C×4) shows that its structure is correct.

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Abstract

The invention discloses application of a digallate derivative which has a formula (I) and a pharmaceutically acceptable salt thereof to preparation of a medicine for treating hyperuricemia. The digallate derivative has a strong effect of inhibiting xanthine oxidase in vitro, can be used for reducing the level of serum uric acid of a mouse with hyperuricemia significantly, is dose dependent and can be used for treating hyperuricemia and gout or gout complications caused by hyperuricemia as a potential xanthine oxidase inhibitor and a potential uric acid lowering medicine.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and specifically relates to the application of a bis-gallate derivative and a pharmaceutically acceptable salt thereof in the preparation of a medicine for treating hyperuricemia, and a medicine for treating hyperuricemia and gout combination. Background technique [0002] In the field of chemical medicine, uric acid is the terminal metabolite of human purine compounds. Disorders of purine metabolism lead to hyperuricemia. Under a normal purine diet, if the blood uric acid level on an empty stomach is higher than 420 μmol / L for men and 360 μmol / L for women on two different days, it is called hyperuricemia. The prevalence of this disease is affected by many factors, related to heredity, sex, age, lifestyle, eating habits, drug treatment and economic development. According to reports on the prevalence of hyperuricemia in various places in recent years, there are currently about 120 million hyper...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/7024A61K31/235A61K31/495A61P19/06A61P19/02A61P13/12A61P13/04A61P9/00C07H13/08C07H1/08C07C69/732C07C67/31C07D295/192
Inventor 温尧林夏增华
Owner CATCH BIO SCI & TECH
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