Immunity excitant containing selenium

An agonist, selenium technology, applied in antiviral, digestive system, organic chemistry, etc., can solve the problem of not including the 8-position selenol group, etc., to achieve the effect of enhancing immunity, improving activity and good curative effect

Inactive Publication Date: 2008-07-30
靳广毅
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But not including the 8-selenol compound and its salt, and their medical use

Method used

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  • Immunity excitant containing selenium
  • Immunity excitant containing selenium
  • Immunity excitant containing selenium

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0036] synthetic route:

[0037]

[0038] 3.78 grams of compound 7 and 12.3 grams of selenourea were mixed and dissolved in 150 milliliters of absolute ethanol. Heated to reflux for 24 hours, cooled to 10° C. for 4 hours, filtered, and dried at room temperature to obtain compound 1 (3.2 grams. Yield 85%) ).The melting point of the product is 283--285℃. 1 H NMR (DMSO-d 6 )δ10.38(1H, s), 7.34-7.24(5H, m), 6.44(2H, s), 4.85(2H, s), 4.24(2H, t, J=4.6Hz), 3.57(2H, t , J=4.6Hz), 3.20 (3H, s); MS (ESI) m / z 379 (MH + ); HRMS calcd for C 15 h 17 N 5 o 2 Se 378.2910, found 378.2911.

Synthetic example 2

[0040] synthetic route:

[0041]

[0042] Cool 5 ml of a 2M lithium aluminum hydride solution in tetrahydrofuran to -78°C. Slowly add 10 ml of a 1M solution of N,N'-dimethylethylenediamine in anhydrous tetrahydrofuran under cooling. The resulting solution for the following reactions.

[0043] Dissolve 1.34 g of compound 8 in 20 ml of anhydrous tetrahydrofuran solution and slowly add to the above mixture at 0°C. After stirring for 1 hour, the reaction mixture was poured into 100 ml of ice water and extracted with ethyl acetate (3X50mL) , combined the extracts, distilled under reduced pressure, and the residue was separated by silica gel column chromatography (eluent: chloroform:methanol=10:1) to obtain compound 2. (1.01 g, yield 75%). 1 H NMR (DMSO-d 6 )δ11.12(1H, s), 10.38(1H, s), 7.03-7.45(5H, m), 6.43(2H, s), 4.87(2H, s), 4.26(2H, t, J=4.6Hz ), 3.55 (2H, t, J=4.6Hz), 3.24 (3H, s); MS (ESI) m / z 407 (MH + ); HRMScalcd for C 16 h 17 N 5 o 3 Se 406.3011, found 406.301...

Synthetic example 3

[0045] synthetic route:

[0046]

[0047] Compound 8 (2 g) was dissolved in 100 ml of anhydrous methanol, 0.5 g of active nickel (R-nickel) was added, and hydrogenated at room temperature and pressure for 12 hours. Filtered, the filtrate was evaporated to dryness to obtain a solid product, and a small amount of methanol Washed and dried to obtain compound 3 (1.86 g, yield 92%). 1 H NMR (DMSO-d 6 )δ10.40(1H, s), 7.63-7.47(5H, m), 6.34(2H, s), 5.56(2H, m), 4.96(2H, s), 4.28(2H, t, J=4.6Hz ), 3.65 (2H, t, J=4.6Hz), 3.44 (2H.s), 3.25 (3H, s); MS (ESI) m / z 408 (MH + ); HRMS calcd for C 16 h 20 N 6 o 2 Se 407.3310, found 407.3011.

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PUM

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Abstract

The invention relates to an immune agonist containing element selenium for improving the immune function, in particular to a purine compound 8-substituted derivative. The immune agonist containing selenium element of the invention is a compound showed in formula (1). Owing to the immune-competence of the selenium element, the immune agonist containing selenium element of the invention leads to stronger immune improving activity of the compound than the corresponding compound analog (the representative compound 9) of the invention, which is applied in resisting viral diseases such as Hepatitis B Virus and Hepatitis C Virus, AIDS, SARS, human influenza and bird flu, and the treatment and assistance of various cancers, with good efficacy.

Description

(1) Technical field [0001] The invention relates to a selenium-containing immune stimulant for improving immune function, which can be used for antiviral drugs, including anti-viral diseases such as hepatitis B and C, AIDS, SARS, human influenza and bird flu, and can also be used for various The treatment and adjuvant treatment of cancer; in particular, it relates to a derivative substituted at the 8-position of a purine compound. (2) Background technology [0002] Yoshiakt Isobe et al disclosed 6-amino-9-methylenearyl-2-(2-methoxy-ethoxy)-9H-purine compounds in patents (JP 2004137157) and (WO 2005092893) respectively The 8-position substituted derivatives (6-Amino-9-benzyl-2-(2-methoxy-ethoxy)-9H-purin-8-substituents), including 8-position hydroxyl, 8-position mercapto, 8- Substituents such as acyloxy and 8-alkoxyacyloxy. However, there are no compounds and their salts including the 8-selenol group, and their medical uses. The representative compound 9 of the above-menti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/52A61P31/12A61P1/16A61P35/00C07D473/18
Inventor 靳广毅
Owner 靳广毅
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