3-aryl-7H-thiazol[3,2-b]-1,2,4-triazinyl-7-one derivatives and application thereof

A CH2, drug technology, applied in the field of medicine, can solve problems such as drug resistance or pharmacokinetic deficiencies

Inactive Publication Date: 2012-11-28
SHIJIAZHUANG 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, stigmi...

Method used

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  • 3-aryl-7H-thiazol[3,2-b]-1,2,4-triazinyl-7-one derivatives and application thereof
  • 3-aryl-7H-thiazol[3,2-b]-1,2,4-triazinyl-7-one derivatives and application thereof
  • 3-aryl-7H-thiazol[3,2-b]-1,2,4-triazinyl-7-one derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of 2-methyl-4-methylenethienoxazolone

[0033] Add 0.1 mol of 2-thiophene carboxaldehyde, 0.12 mol of acetylglycine, 0.12 mol of anhydrous sodium acetate and 50 grams of acetic anhydride into a 100-degree three-necked flask in sequence, heat and reflux and stir for 5 hours to react. After cooling to room temperature, the solution becomes solid. Suction filtration, the filter cake was washed with cold water, and recrystallized with acetone to obtain 19.3 g of the desired product as a yellow crystalline powder with a yield of 100% and MS m / z (M) 193.

Embodiment 2

[0035] Preparation of α-Acetamido-β-thiophene Acrylic Acid

[0036] Add 0.1mol of 2-methyl-4-methylenethienoxazolone compound, 100mL of water, and 80mL of acetone into a 100mL round-bottomed flask in sequence, heat to reflux and stir for 3 hours, cool to room temperature, and a large number of yellow solids are precipitated. After suction filtration, the filter cake was rinsed with cold water and a small amount of acetone, and recrystallized with acetone to obtain 20.3 g of the desired product as yellow crystals, with a yield of 96.2 and MS m / z (M) 211.

Embodiment 3

[0038] Preparation of β-thienylpyruvate

[0039]Add 0.1mol of α-acetylamino-β-thiophene acrylic acid, 60mL of 1mol / L HCl solution into a 100mL round-bottomed flask, heat and reflux for 1 hour, stop the reaction, filter while it is hot, and solids precipitate out of the filtrate. Cooling, suction filtration, recrystallization from absolute ethanol to obtain 15.5 g of the desired product red crystals, yield 91.2%, MS m / z (M) 170.

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Abstract

The invention discloses 3-aryl-7H-thiazol[3,2-b]-1,2,4-triazinyl-7-one derivatives and application thereof, particularly 3-aryl-7H-thiazol[3,2-b]-1,2,4-triazinyl-7-one derivatives disclosed as general formula I or pharmaceutically acceptable hydrates and salts thereof, and application in enhancing memory of patients with dementia and Alzheimer's disease. In the general formula I, R1 and R2 are respectively and randomly one or two or three of H, halogens, hydroxy group, methoxy group, methyl group, nitro-group, -O(CH2)n1NR3R4 and -O(CH2)n2CONR5R6; R3, R4, R5 and R6 are respectively selected from methyl group, ethyl group, pyrrolidinyl group formed by the methyl or ethyl group and nitrogen atom connected with the methyl or ethyl, methylpyrrolidinyl group, dimethylpyrrolidinyl group, piperidyl group, morpholinyl group or hexamethylene imino group ring; n1 is a whole number ranging from 2 to 6; n2 is a whole number ranging from 1 to 6; and X is O or S.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to 3-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives and a preparation method thereof and as an inhibitor of acetylcholinesterase medicament for improving 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 thus may be used to improve memory in Alzheimer's disease patients. By inhibiting acetylcholinesterase, the compound increases levels of the ne...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61K31/53A61P25/28
Inventor 刘斯婕何敬宇史兰香张宝华
Owner SHIJIAZHUANG UNIVERSITY
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