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Bifendate derivative containing halogen substituent, preparation method and application

A bifendate, halogen-containing technology, applied in the field of chemical medicine, can solve the problems of inability to achieve healing effect, rebound, etc.

Inactive Publication Date: 2013-04-24
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clinical studies have shown that bifendate has a strong inhibitory effect on the alanine aminotransferase in the liver, so the alanine aminotransferase in the serum can drop to normal in a short time after the drug, but the normality of the alanine aminotransferase in the serum does not mean the recovery of liver lesions Or normal, the patient should be treated as a cure for hepatitis, so the patient will often appear "rebound" phenomenon after stopping the drug, which cannot achieve a good healing effect

Method used

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  • Bifendate derivative containing halogen substituent, preparation method and application
  • Bifendate derivative containing halogen substituent, preparation method and application
  • Bifendate derivative containing halogen substituent, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0293] Example 1: 4,4'-dimethoxy-5,6,5',6'-two methylenedioxy-2,2'-biphenyl dicarboxylic acid (compound 2)

[0294] 10g of 4,4'-dimethoxy-5,6,5',6'-dimethoxy-2,2'-biphenyl dicarboxylate (compound 1) 10g, add 15g KOH and 300ml water, Heat to reflux for 6 hours, TLC detects that the reaction is complete, cool to room temperature and filter to remove insoluble matter, adjust the pH to 2 with concentrated hydrochloric acid, at this time a large amount of white solid powder precipitates, filter and wash with water until neutral, and vacuum dry to obtain 8.34g of white solid powder , yield 89.5%. 1 H-NMR (d 6 -DMSO, 400MHz) δ: 3.88(s, 6H), 5.96(s, 2H), 5.99(s, 2H), 7.26(s, 2H), 12.36(s, 2H).MS(ESI, m / z) : 389.19[M-H] - .

Embodiment 2

[0295] Example 2: Preparation of 4,4'-dimethoxy-5,6,5',6'-dimethoxy-2,2'-biphenyl dicarboxylic anhydride (compound 3)

[0296] Add 50ml of acetic anhydride to 8.3g of compound 2, heat and reflux for 12h, cool to room temperature after the reaction is complete, spin off the solvent to obtain a light yellow solid powder, add the obtained solid powder to 50ml of anhydrous toluene, mix well, filter with suction, and wash with anhydrous toluene Three times, 6.1 g of white solid powder was obtained, with a yield of 73.6%. The obtained product was directly used in the next reaction without further purification.

Embodiment 3

[0297] Example 3: Preparation of 4,4'-dimethoxy-5,6,5',6'-dimethoxy-2-methoxycarbonyl-2'-carboxylic acid biphenyl (compound 4)

[0298] Weigh 6.1g of compound 3, add 200ml of methanol, add reflux for 10h, TLC detects that the reaction is complete, cool to room temperature, spin off most of the methanol, filter with suction, wash the filter cake twice with ethanol, and dry to obtain 5.9g of white solid powder , yield 96.7%. 1 H-NMR (d 6 -DMSO, 400MHz) δ: 3.58(s, 3H), 3.89(s, 6H), 5.97-6.01(m, 4H), 7.24(s, 1H), 7.27(s, 1H), 12.34(s, 1H) .MS (ESI, m / z): 427.16 [M+Na] + .

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Abstract

The invention belongs to the chemical medicine technical field, and particularly relates to a bifendate derivative containing halogen substituent, a preparation method and an application of the bifendate derivative for treating autoimmune disease. AA structure of the bifendate derivative containing halogen substituent is shown as a formula I, the experiments prove that the bifendate derivative containing halogen substituent shown in the formula I has good effect for treating autoimmune disease, and the bifendate derivative containing halogen substituent has the effect for inhibiting autoimmune diseases such as acute hepatitis, chronic hepatic fibrosis or pulmonary fibrosis, and provides a new selection for medicament exploitation for treating diseases.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and in particular relates to a halogen-substituted bifendate derivative, a preparation method and an application thereof. Background technique [0002] Biphenyl diester (4,4'-dimethoxy-5,6,5',6'-dimethyldioxy-2,2'-biphenyl dicarboxylate) is a synthetic The analogue of ketone has the effect of reducing the high serum glutamate aminotransferase in mice caused by carbon tetrachloride and thioacetamide, and it has been used clinically for the treatment of acute and chronic hepatitis. Through the research on the metabolism of bifendate, it is found that bifendate is not destroyed in the gastrointestinal tract, and the absorption is very little, only about 20%. Experiments have shown that after oral administration of bifendate starch suspension or tablet in rats, mice, and normal people, the bioavailability is only 25-30%. Clinical studies have shown that bifendate has a strong inhibit...

Claims

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Application Information

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IPC IPC(8): C07D317/60C07D417/14A61K31/36A61K31/427A61P29/00
Inventor 陈俐娟魏于全
Owner SICHUAN UNIV
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