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Preparation method for drug for treating aids

A technology for AIDS and drugs, which is applied in the field of preparation of drugs for the treatment of AIDS, and can solve problems such as unsatisfactory inhibitory activity of cancer cells

Inactive Publication Date: 2018-07-27
曹艳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The compound formula (I) involved in the present invention was originally used in the research and development of cancer, but its inhibitory activity on cancer cells was not ideal. After further activity tests, it was surprisingly found to have HIV integrase inhibitory activity

Method used

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  • Preparation method for drug for treating aids
  • Preparation method for drug for treating aids
  • Preparation method for drug for treating aids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Synthesis of intermediate N-(thiazole-2-methylene)-8-chloroquinazolin-2-amine

[0025]

[0026] Dissolve 8-chloroquinazolin-2-amine (10 mmol) and 2-thiazole formaldehyde (11 mmol) in 30 ml of methanol / tetrahydrofuran (2:1) mixed solvent, reflux for 1 hour, then cool down to room temperature, and add to the system Add water (50 ml), extract with 50 ml of dichloromethane, dry the organic phase over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, recrystallize with acetone and ethanol (1:4), filter, and dry under vacuum at 50°C. 2.6 g of dark yellow N-(thiazole-2-methylene)-8-chloroquinazolin-2-amine solid was obtained, with a yield of 95%. 1 H-NMR (400 MHz, CDCl 3 ) δ: 7.41-7.48(m,2H), 7.80-7.84(m,2H), 8.12(d,1H), 8.66(s,1H), 9.74(s,1H).

Embodiment 2

[0027] Example 2: Synthesis of intermediate N-(thiazole-2-methyl)-8-chloroquinazoline-2-secondary amine

[0028]

[0029] Dissolve N-(thiazole-2-methylene)-8-chloroquinazolin-2-amine (10 mmol) in 40 ml of methanol, then add 5 ml of glacial acetic acid, cool to 0-5°C, and then add 1.2 gram of sodium borohydride, stirred at low temperature for 2 hours, raised to room temperature and continued to stir for half an hour, then added 100 ml of water to the system, stirred for 1 hour, filtered, and vacuum-dried at 50°C to obtain 2.54 g of brown-yellow N-(thiazole-2 -methyl)-8-chloroquinazoline-2-secondary amine solid powder, yield 92%. 1 H-NMR (400 MHz, CDCl 3 ) δ: 3.29(s,1H), 4.65(s,2H), 7.20(d,1H), 7.48(t,1H), 7.65(d,1H), 7.79(m,1H), 8.12(m,1H ), 9.43(s,1H).

Embodiment 3

[0030] Example 3: Synthesis of N-(thiazole-2-methyl)-8-phenylquinazoline-2-secondary amine

[0031]

[0032] Dissolve N-(thiazole-2-methyl)-8-chloroquinazoline-2-secondary amine (10 mmol) in 30 ml of nitrogen dimethylformamide, blow the system with argon for 20 minutes, and evacuate the system Then add tetrakis triphenylphosphine palladium (1 mmol), heat up to 60 ° C, continue to stir for half an hour, add phenylboronic acid (12 mmol) to it, then add 10 ml of sodium carbonate (1 g) aqueous solution, heat up Stir at 90°C for 5 hours, keep argon flowing during the whole process, then lower the temperature, evaporate the solvent under reduced pressure, and the solid passes through the chromatographic column quickly to obtain 2.9 g of off-white solid, which is N-(thiazole-2-methyl) -8-phenylquinazoline-2-secondary amine, yield 91%. 1 H-NMR (400 MHz, CDCl 3 ) δ: 3.18(s,1H), 4.65(s,2H), 7.18-7.21(m,5H), 7.41(m,1H),7.65-7.73(m,2H), 7.99-8.04(m,2H) , 9.43(s,1H). 13 C-NMR (75 MH...

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Abstract

The invention discloses a preparation method for a drug for treating aids. A chemical structure of the drug is shown in formula (I); when concentration is 5 mu g / ml, an inhibition ratio of a compoundHIV-1 integrase as shown in formula (I) is 45%-95%, and an inhibition ratio of Ib is as high as 94.8%, which exceed the inhibition ratio of the drug elvitegravir in the market. The inhibition ratio ofIa is low which is lower than 50%. The compound as shown in the formula (I) can be used as HIV-1 integrase inhibitor for treating aids.

Description

[0001] This application is a divisional application of a patent with an application date of July 9, 2017, an application number of 2017105540438, and an invention titled "a drug for treating AIDS and its preparation method". technical field [0002] The invention relates to a preparation method of a medicine for treating AIDS. Background technique [0003] AIDS is a very harmful infectious disease. The drugs that have been marketed mainly include reverse transcriptase inhibitors (reverse transcriptase inhibitors), protease inhibitors (protease inhibitors), fusion inhibitors (fusion inhibitors), HIV integrase inhibitors ( integrase inhibitors), etc. [0004] HIV integrase inhibitors are anti-HIV / AIDS drugs with a new mechanism of action. They can be used in combination with other antiretroviral drugs to effectively treat HIV infection, and clinical drug resistance is not easy to develop. [0005] HIV-1 integrase is an essential enzyme for retroviral replication and has no an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12
CPCC07D417/12
Inventor 曹艳
Owner 曹艳
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