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Drug for treating acquired immunodeficiency syndrome (AIDS) and preparation method thereof

A technology for AIDS and medicine, applied in the field of medicine for the treatment of AIDS and its preparation, can solve the problems of unsatisfactory cancer cell inhibitory activity and the like

Active Publication Date: 2017-08-25
梁山县疾病预防控制中心梁山县卫生检测检验中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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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  • Drug for treating acquired immunodeficiency syndrome (AIDS) and preparation method thereof
  • Drug for treating acquired immunodeficiency syndrome (AIDS) and preparation method thereof
  • Drug for treating acquired immunodeficiency syndrome (AIDS) and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Synthesis of intermediate N-(thiazole-2-methylene)-8-chloroquinazolin-2-amine

[0022]

[0023] 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

[0024] Example 2: Synthesis of intermediate N-(thiazole-2-methyl)-8-chloroquinazoline-2-secondary amine

[0025]

[0026] 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

[0027] Example 3: Synthesis of N-(thiazole-2-methyl)-8-phenylquinazoline-2-secondary amine

[0028]

[0029] 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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PUM

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Abstract

The invention discloses a drug for treating acquired immunodeficiency syndrome (AIDS) and a preparation method thereof. The chemical structure of the drug is a formula (I), when the concentration is 5 micrograms per milliliter, the inhibition rate of a compound HIV-integrase shown in the formula (I) is from 45% to 95%, and the inhibition rate of Ib is up to 94.8% and exceeds that of a listed drug Elvitegravir. The inhibition rate of Ia is relatively low and less than 50%. The compound shown in the formula (I) can be taken as a HIV-integrase inhibitor and used for treating the acquired immunodeficiency syndrome (AIDS).

Description

technical field [0001] The invention relates to a medicine for treating AIDS and a preparation method thereof. Background technique [0002] 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. [0003] 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. [0004] HIV-1 integrase is an essential enzyme for retroviral replication and has no analog in human cells, making it an attractive and plausible target for the treatment of AIDS. Integrase inhibitors refer to drugs that inhibit integrase, that is, inhibit the replication process of retroviruses, and bl...

Claims

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Application Information

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IPC IPC(8): C07D417/12A61K31/517A61P31/18
CPCC07D417/12
Inventor 曹艳
Owner 梁山县疾病预防控制中心梁山县卫生检测检验中心
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