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Thiazole compound capable of restraining human immunodeficiency virus (HIV) replication and effective against drug-resistant HIV virus strains and preparation method and purpose thereof

A compound and medicinal salt technology, applied in the field of thiazole compounds, which can inhibit HIV replication and are effective against drug-resistant HIV strains, and its preparation and application, can solve problems such as treatment failure and mutation

Active Publication Date: 2013-06-19
CAPITAL NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With long-term and widespread use of highly active antiretroviral therapy, HIV develops stable drug-resistant mutations and spreads, leading to treatment failure

Method used

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  • Thiazole compound capable of restraining human immunodeficiency virus (HIV) replication and effective against drug-resistant HIV virus strains and preparation method and purpose thereof
  • Thiazole compound capable of restraining human immunodeficiency virus (HIV) replication and effective against drug-resistant HIV virus strains and preparation method and purpose thereof
  • Thiazole compound capable of restraining human immunodeficiency virus (HIV) replication and effective against drug-resistant HIV virus strains and preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0225] The preparation of embodiment 1N-benzyl-5-benzyl-4-(4-methoxyphenyl)-thiazol-2-amine

[0226]

[0227] Step 1 Preparation of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one

[0228] Put 0.57g (3.8mmol) of p-methoxyacetophenone in a 25mL three-necked flask, add 6mL of absolute ethanol, add 5.7mL of sodium hydroxide solution, stir for 5min, and add 0.51g of (3.8mmol) benzaldehyde, kept in ice-water bath for 4h, TLC monitored the completion of the reaction, filtered, washed with water, and recrystallized from ethanol to obtain 0.81g of light yellow solid with a yield of 90.0%.

[0229] Step 21- Preparation of (4-methoxyphenyl)-3-phenylpropan-1-one

[0230] Dissolve 3.66g (15.39mmol) of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one prepared in step 1 in 80mL of ethyl acetate, add catalyst Measure Pd / C, after catalytic hydrogenation for 2 hours, filter, and rotary steam under reduced pressure to obtain 3.68g of transparent oily substance, yield 99.6%, m.p.96.5-97.2°C....

Embodiment 2

[0239] The preparation of embodiment 2N-(4-methoxybenzyl)-5-benzyl-4-(4-methoxyphenyl)-thiazol-2-amine

[0240]

[0241] Adopt the preparation method of embodiment 1 step 5 and step 6, 5-benzyl-4-(4-methoxyphenyl)-thiazol-2-ylamine and p-methoxybenzene prepared by embodiment 1 step 4 Formaldehyde was used as a raw material to obtain a white solid with a yield of 85.0% and m.p.151.2.7-152.4°C. 1 H NMR (CDCl 3 ,300MHz)δ:3.80(s,3H,OCH 3 ),3.81(s,3H,OCH 3 ),4.00(d,2H,J=6.0Hz,ArCH 2 ),4.35(s,2H,ArCH 2 ),5.35(br,1H,NH),6.85~6.91(m,4H,ArH),7.21~7.33(m,7H,ArH),7.49~7.52(m,2H,ArH); ESI-MS m / z :417([M+H] + ).

Embodiment 3

[0242] The preparation of embodiment 3N-(3-methoxy-4-hydroxybenzyl)-5-benzyl-4-(4-methoxyphenyl)-thiazol-2-amine

[0243]

[0244] Adopt the preparation method of embodiment 1 step 5 and step 6, 5-benzyl-4-(4-methoxyphenyl)-thiazol-2-ylamine and 4-hydroxyl-3 prepared by embodiment 1 step 4 -Methoxybenzaldehyde was used as a raw material to obtain a white solid with a yield of 73.0%, m.p.137-138°C. 1 H NMR (CDCl 3 ,600MHz)δ:3.81(s,3H,OCH 3 ),4.10(s,2H,ArCH 2 ),4.39(s,2H,ArCH 2 ),5.80(br,1H,NH),6.90(d,J=8.4Hz,2H,ArH),7.02(d,J=8.4Hz,2H,ArH),7.23~7.33(m,7H,ArH), 7.50(d,J=7.5Hz,2H,ArH);ESI-MS m / z:433([M+H] + ).

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PUM

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Abstract

The invention provides a 2,4,5-tri-substituted thiazole compound which is in a general formula I and can serve as a human immunodeficiency virus (HIV) replication inhibitor, and all possible isomers or prodrug or medicinal salt or solvate or aquo-complex of the 2,4,5-tri-substituted thiazole compound, and further provides a preparation method for the compound in the general formula I as well as a medical composition of the compound in the general formula I, and the purpose of the compound in the medicine preparation process. The medicine is used for treating and / or preventing diseases caused by HIV infection.

Description

technical field [0001] The present invention relates to 2,4,5-trisubstituted thiazole compounds capable of inhibiting HIV replication, their preparation methods, combined medicines containing them, and the use of them to prepare anti-HIV medicines, including their application in the medical field . Background technique [0002] Human immunodeficiency virus (human immunodeficiency virus, HIV) is an RNA virus that infects the T lymphocytes of the human immune system and causes severe damage to the function of the human immune system, leading to death. The disease caused by the virus is called acquired immunodeficiency syndrome (acquiredimmuneficiency syndrome, AIDS), also known as AIDS. [0003] According to statistics from the United Nations Program on AIDS (UNAIDS), since the first case of AIDS was discovered in the United States in 1981, more than 60 million people have been infected with HIV and caused about 25 million deaths. The 2011 Global AIDS Epidemic Report release...

Claims

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Application Information

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IPC IPC(8): C07D277/42C07D417/12C07D417/04A61K31/425A61K31/427A61K31/4439A61K31/454A61P31/18
Inventor 郭长彬郭颖李振中霸明宇徐仲亮曹颖莉何日才杨颖周化李乐涛唐朝军陈勍张梦迪吴迪朱利红
Owner CAPITAL NORMAL UNIVERSITY
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