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Thiazolo[3,2-b]-1,2,4-triazine derivative and use thereof

A compound, CH2 technology, used in the field of medicine to solve problems such as drug resistance or pharmacokinetic deficiencies

Inactive Publication Date: 2009-08-12
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, stigmine, galantamine, etc., still have drug resistance or pharmacokinetic defects

Method used

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  • Thiazolo[3,2-b]-1,2,4-triazine derivative and use thereof
  • Thiazolo[3,2-b]-1,2,4-triazine derivative and use thereof
  • Thiazolo[3,2-b]-1,2,4-triazine derivative and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0125] Example 1: 6-(4-methoxybenzyl)-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one preparation of

[0126] Add 0.1 mol of p-methoxybenzaldehyde, 0.12 mol of acetylglycine, 0.12 mol of anhydrous sodium acetate and 50 grams of acetic anhydride into a 100 mL three-necked flask in sequence, heat and reflux and stir for 5 hours, and after cooling to room temperature, the solution becomes The solid was filtered with suction, the filter cake was washed with cold water, and recrystallized with acetone to obtain 21.7 g of 2-methyl-4-(4-methoxybenzylidene) oxazolone yellow crystalline powder, yield 100%, MS m / z(M)217.

[0127] Add 0.1mol of 2-methyl-4-(4-methoxybenzylidene)oxazolone, 100ml of water, and 80ml of acetone into a 100ml round-bottomed flask in turn, heat to reflux and stir for 3 hours, cool to room temperature, and precipitate A large number of yellow solids were suction filtered, the filter cake was washed with cold water and a small amount of acetone, and ...

Embodiment 2

[0130] Example 2: Preparation of 6-benzyl-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one

[0131] According to the method of Example 1, 2.01 grams of 6-benzyl-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one yellow crystals were obtained , yield 60%, MS m / z (M) 335; 1HNMR (DMSO): δ 4.00 (2H, s), 6.72 (2H, d, J=8.7Hz), 7.06-7.14 (5H, m), 7.20 (2H, d, J=8.7Hz), 7.28 (1H, s), 8.00 (1H, s).

Embodiment 3

[0132] Example 3: 6-(3-methoxybenzyl)-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one preparation of

[0133] According to the method of Example 1, 6-(3-methoxybenzyl)-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazine- 2.19 g of 7-keto yellow crystals, yield 60%, MS m / z (M) 365; 1 HNMR(DMSO): δ 3.70(3H, s), 4.00(2H, s), 6.57(1H, s), 6.65(2H, d, J=8.7Hz), 6.72-6.95(3H, m,), 7.20 (2H, d, J = 8.7 Hz), 7.28 (1H, s), 8.00 (1H, s).

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Abstract

The invention belongs to the technical field of medicine, and relates to a thiazolo(3,2-b)-1,2,4-triazine derivative and applications thereof. The thiazolo(3,2-b)-1,2,4-triazine derivative includes stereoisomers and pharmaceutically applicable salts of the compound, and has a general structural formula as shown follow. The thiazolo(3,2-b)-1,2,4-triazine derivative and the salts added by pharmaceutically applicable acids of the compound can be used by combining with the existing medicaments or separately as acetylcholinesterase inhibitors for enhancing the memory of patients suffering from dementia and alzheimer.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to thiazolo[3,2-b]-1,2,4-triazine derivatives and applications thereof, in particular to thiazolo[3,2-b]-1,2,4 - Triazine derivatives, stereoisomers and pharmaceutically applicable salts of such compounds and applications thereof. The compounds are acetylcholinesterase inhibitors and are 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 effective in increasing cholinergic activity and...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61K31/53A61P25/28
Inventor 胡春刘斯婕杨柳金辄刘晓光黄二芳徐赫男温志昌林煌权
Owner SHENYANG PHARMA UNIVERSITY