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Benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative and application thereof

A triazine derivative, benzoyl technology, applied in the field of medicine, can solve problems such as drug resistance or pharmacokinetic defects

Inactive Publication Date: 2015-03-11
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Existing acetylcholinesterase inhibitors, such as tacrine, rivastigmine, galantamine, etc., all have drug resistance or pharmacokinetic defects

Method used

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  • Benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative and application thereof
  • Benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative and application thereof
  • Benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1: 3-(4-hydroxyphenyl)-6-[2-oxo-2-phenylethyl]-7 H -Thiazolo[3,2- bPreparation of ]-1,2,4-triazin-7-one

[0059] Add 50 mL toluene, 0.1 mol sodium ethoxide and 0.05 mol diethyl oxalate into a 500 mL round bottom flask, heat to reflux for 5 min, add 0.02 mol acetophenone, and react at room temperature for 10 h. After the reaction was completed, pour 100 mL of water into the reaction solution, separate the layers, take the water layer, wash the water layer with 20 mL of ether, acidify with 1 mol / L hydrochloric acid, and a solid precipitated out. Cool, filter, wash and dry. A light yellow solid was obtained, which was recrystallized from ethanol to obtain 9.2 g of white crystals, with a yield of 90%.

[0060] Add 1.0 g (0.004 mol) of ethyl 2,4-dioxo-4-phenylbutyrate, 0.37 g (0.004 mol) of thiosemicarbazide, 20 mL of ethanol, and 20 mL of water into a 250 mL round bottom flask in sequence 40% aqueous sodium hydroxide solution was used to adjust the pH value of t...

Embodiment 2

[0062] Example 2: 3-(4-bromophenyl)-6-[2-oxo-2-(4-methoxyphenyl)ethyl]-7 H -Thiazolo[3,2- b Preparation of ]-1,2,4-triazin-7-ones.

[0063] According to the method of Example 1, 3-(4-bromophenyl)-6-[2-oxo-2-(4-methoxyphenyl)ethyl]-7 H -Thiazolo[3,2- b ]-1,2,4-triazin-7-one 1.08 g. 1 H-NMR (300 MHz, DMSO- d 6 ): δ 7.96 (2H, d, J = 9.0 Hz), 7.72 (2H, d, J = 8.4 Hz), 7.48 (2H, d, J = 8.4 Hz), 7.34 (1H, s), 7.04 (2H, d, J = 9.0 Hz), 3.85 (3H, s), 2.72 (2H, s); ESI-MS (m / z): 455.9 (M+H) + , 457.9 (M+2+H) + .

Embodiment 3

[0064] Example 3: 3-(4-methoxyphenyl)-6-[2-oxo-2-(4-chlorophenyl)ethyl]-7 H -Thiazolo[3,2- b Preparation of ]-1,2,4-triazin-7-one

[0065] According to the method of Example 1, 3-(4-methoxyphenyl)-6-[2-oxo-2-(4-chlorophenyl)ethyl]-7 H -Thiazolo[3,2- b ]-1,2,4-triazin-7-one 1.24 g. 1 H-NMR (300 MHz, DMSO- d 6 ): δ 8.08 (2H, d, J = 8.4 Hz), 7.76 (2H, d, J = 9.0 Hz), 7.64 (2H, d, J = 9.0 Hz), 7.56 (2H, d, J = 8.4 Hz), 7.32 (1H, s), 3.82 (3H, s), 2.67 (2H, s); ESI-MS (m / z): 412.0 (M+H) + , 414.1 (M+2+H) + , 434.0 (M+Na) + .

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Abstract

The invention belongs to the field of medical technology, and relates to a benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative and an application thereof. The benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative comprises a stereoisomer and pharmaceutically acceptable salt of the benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative, wherein the structural general formula is shown in the specification; and the benzoyl substituted thiazolo[3,2-b]-1,2,4-triazine derivative and the pharmaceutically acceptable acid-added salt of the compound can be combined with the existing medicine or independently used as an acetylcholin esterase inhibitor and used for improving the memory of the patients suffering from dementia and Alzheimer disease. Compared with the existing Chinese patent, the 6-site side chain of thiazolo[3,2-b]-1,2,4-triazine is obviously changed, and the inhibition ratio of a sample against acetylcholin esterase is obviously improved.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to benzoyl-substituted thiazolo[3,2- b ]-1,2,4-triazine derivatives and applications thereof, in particular to benzoyl-substituted thiazolo[3,2- b ]-1,2,4-triazine derivatives, stereoisomers and pharmaceutically applicable salts of the compounds and applications thereof. The compounds are acetylcholinesterase inhibitors that can be used to improve memory in patients with dementia and Alzheimer's disease. Background technique [0002] Alzheimer's disease is associated with the degeneration of cholinergic neurons in the basal forebrain, which play an important role in recognition functions, including memory. As a result of said degeneration, patients suffering from this disease exhibit marked attenuations in acetylcholine synthesis, choline acetyltransferase activity, acetylcholinesterase activity, and choline absorption. [0003] Acetylcholinesterase inhibitors are known to be effec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04A61K31/53A61K31/5377A61P25/28
Inventor 胡春刘晓光金辄徐赫男刘晓平黄二芳温志昌
Owner SHENYANG PHARMA UNIVERSITY
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