Azobenzene derivatives and their preparation method, pharmaceutical composition and use

A technology of azobenzene derivatives and azobenzene, which is applied in drug combinations, antipyretics, antitumor drugs, etc., to achieve high bioavailability

Active Publication Date: 2016-05-11
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although many inventions have made great contributions to this field, in orde

Method used

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  • Azobenzene derivatives and their preparation method, pharmaceutical composition and use
  • Azobenzene derivatives and their preparation method, pharmaceutical composition and use
  • Azobenzene derivatives and their preparation method, pharmaceutical composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1. (E)-4,4'-bis(2-methoxy n-propionic acid methyl ester-3-yl)azobenzene

[0059]

[0060] Methyl 3-p-aminophenyl-2-methoxy n-propionate (1.4g, 6.3mmol) was dissolved in 40mlTHF, the air was removed, sodium iodide (2.0g, 13mmol), t-BuOCl (1.4g, 13mmol), reacted under nitrogen protection for 3h, quenched with 1N sodium thiosulfate solution, extracted with ethyl acetate, washed the organic phase once with water, washed with saturated sodium chloride

[0061] Once, dried over anhydrous sodium sulfate, filtered and chromatographed to obtain 660 mg of an orange solid. 1HNMR (400MHz, DMSO-d 6 )δ:7.83~7.81(d,4H,ArH),7.43-7.41(d,4H,ArH),4.17~4.14(m,2H,-OCH-),3.66(s,6H,2-COOCH 3 -),3.29(s,6H,2-OCH 3 -),3.11~3.06(m,2H,-CH 2 -),3.04~2.85(m,2H,-CH 2 -).MS(FAB):m / z415[M+H] + .

Embodiment 2

[0062] Example 2. (E)-4,4'-bis(2-methoxyethyl n-propionate-3-yl)azobenzene

[0063]

[0064] With reference to Example 1, replace the compound 3-p-aminophenyl-2-methoxy n-propionate methyl ester with 3-p-aminophenyl-2-methoxy n-propionate ethyl ester (6.3mmol), the same operation process (E)-4,4'-bis(2-methoxyethyl-3-yl-n-propionate)azobenzene was obtained as an orange solid. 1 HNMR (400MHz, DMSO-d 6 )δ: 7.83~7.81(d,4H,-ArH),7.46~7.44(d,4H,-ArH),4.14~4.08(m,6H,-2OCH-,-2COOCH 2 -),3.22(s,6H,-2OCH 3 -),3.09~2.99(m,4H,-2CH 2 -),1.16~1.13(t,6H,2CH 3 -).MS(FAB):m / z443[M+H] + .

Embodiment 3

[0065] Example 3. (E)-4,4'-bis(2-methoxy n-propionic acid-3-yl)azobenzene

[0066]

[0067] Dissolve (E)-4,4'-bis(2-methoxyethyl n-propionate-3-yl)azobenzene (0.26g, 0.6mmol) in methanol and water (10ml, 10:1) , add sodium hydroxide (0.12g, 3.0mmol), react at room temperature for 5h, remove the solvent, add 2N HCl to adjust the pH = 2, a solid precipitates, and suction filter to obtain 200mg of (E)-4,4'-bis(2-methanol) Oxy-n-propanoate-3-yl)azobenzene, orange solid. 1 HNMR (400MHz, DMSO-d 6 )δ: 12.87(s, 2H, 2COOH), 7.81~7.79(d, 4H, ArH), 7.46-7.44(d, 4H, ArH), 4.03~4.00(m, 2H, 2OCH-), 3.26(s, 6H,2-OCH 3 ),3.11~3.06(m,2H,-CH 2 -),3.00~2.95(m,2H,-CH 2 -).MS(FAB):m / z387[M+H] + .

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Abstract

The invention discloses azobenzene derivatives and their preparation method, pharmaceutical composition and use and relates to azobenzene derivatives shown in the formula I and their medicinal salts and preparation method, a composition containing one or more of the azobenzene derivatives and a use of the azobenzene derivatives in inflammation disease, immunization imbalance and tumor disease treatment.

Description

field of invention [0001] The present invention relates to an azobenzene derivative represented by formula I, its pharmaceutically acceptable salt, its hydrate and solvate, its polycrystal and cocrystal, its precursor or derivative with the same biological function, and its preparation method, Compositions containing one or more of these compounds, and uses of such compounds in the treatment of inflammatory diseases, immune disorders and tumor diseases. Background of the invention [0002] Inflammatory bowel disease (IBD) is a chronic non-specific intestinal inflammatory disease whose etiology is not yet clear. In recent years, the incidence of IBD has been on the rise both at home and abroad. The pathogenesis of IBD is relatively complex. Factors such as environment, genetics, infection, and immunity may all be involved in the pathogenesis of the disease. Various cytokines are involved in the excessive immune response and pathogenic process of the intestinal tract. [0003...

Claims

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Application Information

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IPC IPC(8): C07C245/08A61K31/655A61P35/00A61P37/02A61P29/00A61P1/00A61P37/08
Inventor 冯志强王景静李莉
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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