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N-[5-(1,2,4-triazole-1-yl)thiazole-2-yl]aromatic amide, and pharmaceutical applications thereof

A technology of thiazole and benzamide, applied in the field of application of N-[5-(1, preparation of influenza virus neuraminidase inhibitors

Inactive Publication Date: 2015-07-15
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies have found that some virus strains are resistant to Oseltamivir, so there is an urgent need to study new anti-influenza A virus drugs

Method used

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  • N-[5-(1,2,4-triazole-1-yl)thiazole-2-yl]aromatic amide, and pharmaceutical applications thereof
  • N-[5-(1,2,4-triazole-1-yl)thiazole-2-yl]aromatic amide, and pharmaceutical applications thereof
  • N-[5-(1,2,4-triazole-1-yl)thiazole-2-yl]aromatic amide, and pharmaceutical applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Preparation of N-[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]benzamide

[0017] 2mmol of 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine was dissolved in 20.0mL of tetrahydrofuran, 8mmol of anhydrous potassium carbonate was added, and 3mmol of benzyl was added dropwise under stirring in an ice bath Acyl chloride, stirred at room temperature, reacted for 2.0h, filtered, the filtrate was rotary evaporated, and column chromatography gave N-[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl] Benzamide, yield 70.2%, m.p.257~260℃. 1 H NMR (400MHz, CDCl 3 ) δ: 1.17 (s, 9H, 3×CH 3 ), 7.55 (t, J=7.6Hz, 2H, C 6 h 5 3,5-H), 7.65(t, J=7.6Hz, 1H, C 6 h 5 4-H), 7.97(d, J=7.6Hz, 2H, C 6 h 5 2,6-H), 8.13 (s, 1H, C 2 N 3 h 2 3-H), 8.28 (s, 1H, C 2 N 3 h 2 5-H), 9.51 (s, 1H, NH).

Embodiment 2

[0019] Preparation of N-[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]-2-methoxybenzamide

[0020] 2mmol of 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine was dissolved in 20.0mL of dichloromethane, 2.2mmol of 2-methoxybenzoic acid was added, 0.03g of 4-di Dimethylaminopyridine (DMAP), after 0.5h, add 2.2mmol N,N'-dicyclohexylcarbodiimide (DCC), stir at room temperature, react for 8.0h, the reaction solution is neutralized with aqueous sodium bicarbonate solution, stand still, and separate layer, the organic layer was dried over anhydrous sodium sulfate, filtered, rotary evaporated, and column chromatography gave N-[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl ]-2-methoxybenzamide, yield 46.7%, m.p.178~180℃. 1 H NMR (400MHz, CDCl 3 ) δ: 1.20 (s, 9H, 3×CH 3 ), 4.17 (s, 3H, OCH 3 ), 7.09 (d, J=8.0Hz, 1H, C 6 h 4 3-H), 7.16 (t, J=8.0Hz, 1H, C 6 h 4 5-H), 7.59 (td, J=8.0Hz, J=2.2Hz, 1H, C 6 h 4 4-H), 8.12(s, 1H, C 2 N 3 h 2 3-H), 8.27 (s, 1H, C 2 N 3 h 2 ...

Embodiment 3

[0022] Preparation of N-[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]-3-nitrobenzamide

[0023] According to the method of Example 2, 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine reacted with 3-nitrobenzoic acid for 5.0h to obtain N-[4 - tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]-3-nitrobenzamide, yield 84.4%, m.p.207~211℃. 1 H NMR (400MHz, CDCl 3 ) δ: 1.20 (s, 9H, 3×CH 3 ), 7.79 (t, J=8.0Hz, 1H, C 6 h 4 5-H), 8.15(s, 1H, C 2 N 3 h 23-H), 8.31 (s, 1H, C 2 N 3 h 2 5-H), 8.41 (d, J=8.0Hz, 1H, C 6 h 4 6-H), 8.50 (d, J=9.6Hz, 1H, C 6 h 4 4-H), 8.89 (s, 1H, C 6 h 4 2-H).

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Abstract

The invention relates to applications of N-[5-(1,2,4-triazole-1-yl)thiazole-2-yl]benzamide represented by chemical structural formula I in preparing influenza neuraminidase inhibitors. According to the chemical structural formula I, R is selected from C1-C2 alkyl, and C3-C4 linear or branched alkyl; R1 and R5 are selected from hydrogen, deuterium, methyl, ethyl, hydroxyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, nitryl, or trifluoromethyl; R2 and R4 are selected from hydrogen, deuterium, methyl, ethyl, hydroxyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, nitryl, trifluoromethyl, amino, or acetamido; and R3 is selected from hydrogen, deuterium, methyl, ethyl, hydroxyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, nitryl, trifluoromethyl, cyanogroup, amino, or acetamido.

Description

technical field [0001] The present invention relates to new applications of compounds, specifically the application of N-[5-(1,2,4-triazol-1-yl)thiazol-2-yl]arylamide in the preparation of influenza virus neuraminidase inhibitors . Background technique [0002] Human infection with avian influenza is a human disease caused by an avian influenza virus. Influenza viruses can generally be divided into types A, B and C, among which type A is commonly referred to as avian influenza, which is pathogenic to humans and various animals. The antigenic variability of type A influenza virus is the strongest, and it is often divided into 16 HA subtypes according to the antigenicity of HA and NA (H 1 ~H 16 ) and nine NA subtypes (N 1 ~N 9 ). The subtypes of avian influenza viruses that can directly infect humans have been found so far: H 5 N 1 、H 7 N 1 、H 7 N 2 、H 7 N 3 、H 7 N 7 、H 9 N 2 and H 7 N 9 Subtype. Among them, highly pathogenic H 5 N 1 The subtype was firs...

Claims

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Application Information

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IPC IPC(8): A61K31/427A61P31/16C07D417/04C07D417/14
Inventor 胡艾希戴明崇孙晓潇叶姣刘艾琳连雯雯
Owner HUNAN UNIV
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