Alkoxy substituted thiazolo [3,2-b]-1,2,4-triazine derivatives and application thereof

A thiazolo, 2-b technology, applied in the field of medicine, can solve problems such as drug resistance or pharmacokinetic defects

Inactive Publication Date: 2013-04-03
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, rivast...

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1: 3-(4-methylphenyl)-6-(4-ethoxyphenyl)-7 H -Thiazolo[3,2- b Preparation of ]-1,2,4-triazin-7-one

[0063]Add 0.2 mol of 4'-ethoxystyrene, 0.4 mol of sodium hydroxide, and 80 mL of water into a 500 mL round bottom flask, heat to 70 °C, add 0.5 mol of potassium permanganate in batches within 0.5 h After reacting for 10 min, the unreacted potassium permanganate was destroyed with 50 mL of ethanol, the reaction solution was filtered with suction, the filtrate was retained, most of the water was distilled off under reduced pressure, and the concentrated filtrate was acidified with concentrated hydrochloric acid. Then extract with dichloromethane, remove the solvent, cool to obtain a light yellow solid, and recrystallize from ethanol to obtain 36.90 g of 2-(4-ethoxyphenyl)-2-oxoacetic acid white crystal powder, yield 95%, ESI -MS (m / z): 193.2 (M–H) – .

[0064] Add 0.01 mol of 2-(4-ethoxyphenyl)-2-oxoacetic acid, 0.01 mol of thiosemicarbazide, 40 mL of ethanol...

Embodiment 2

[0066] Example 2: 6-(4-ethoxyphenyl)-3-(4-bromophenyl)-7 H -Thiazolo[3,2- b Preparation of ]-1,2,4-triazin-7-ones.

[0067] According to the method of Example 1, 6-(4-ethoxyphenyl)-3-(4-bromophenyl)-7 H -Thiazolo[3,2- b ]-1,2,4-triazin-7-one 2.06 g, yield 48%, 1 H-NMR (600 MHz, DMSO- d 6 ): δ 8.11 (2H, d, J = 9.0 Hz), 7.79 (2H, d, J = 8.4 Hz), 7.75 (2H, d, J = 8.4 Hz), 7.62 (1H, s), 7.02 (2H, d, J = 9.0 Hz), 4.09 (2H, q), 1.35 (3H, t); ESI-MS (m / z): 428.2 (M+H) + , 430.2 (M+2+H) + , 450.2 (M+Na) + , 452.2 (M+2+Na) + , 466.2 (M+K) + , 468.2 (M+2+K) + .

Embodiment 3

[0068] Example 3: 3-(4-methoxyphenyl)-6-(4-ethoxyphenyl)-7 H -Thiazolo[3,2- b Preparation of ]-1,2,4-triazin-7-one

[0069] According to the method of Example 1, 3-(4-methoxyphenyl)-6-(4-ethoxyphenyl)-7 H -Thiazolo[3,2- b ]-1,2,4-triazin-7-one 1.38 g, yield 37%, 1 H-NMR (600 MHz, DMSO- d 6 ): δ 8.11 (2H, d, J = 8.4 Hz), 7.73 (2H, d, J = 9.0 Hz), 7.44 (1H, s), 7.11 (2H, d, J = 9.0 Hz), 7.02 (2H, d, J = 9.0 Hz), 4.09 (2H, q), 3.84 (3H, s), 1.35 (3H, t); ESI-MS (m / z): 380.1 (M+H) + , 402.1 (M+Na) + , 418.0 (M+K) + .

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Abstract

The invention belongs to the technical field of medicines and relates to alkoxy substituted thiazolo [3,2-b]-1,2,4-triazine derivatives and application thereof. The alkoxy substituted thiazolo [3,2-b]-1,2,4-triazine derivatives include alkoxy substituted thiazolo [3,2-b]-1,2,4-triazine derivatives, stereisomers of the derivatives, and pharmaceutically applicable salts of the derivatives, and have a structural general formula shown in the specification. The alkoxy substituted thiazolo [3,2-b]-1,2,4-triazine derivatives and salts prepared by addition of pharmaceutically applicable acid of the derivatives can be mixed with the existing medicine or are singly used as an acetylcholin esterase inhibitor, and are used for enhancing memory of a patient suffering from dementia and Alzheimer's disease. Compared with the existing Chinese patient, samples of the alkoxy substituted thiazolo [3,2-b]-1,2,4-triazine derivatives are remarkably increased in the inhibition of acetylcholin esterase.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to alkoxy-substituted thiazolo[3,2-b]-1,2,4-triazine derivatives and applications thereof, in particular to alkoxy-substituted 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 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 effective...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61K31/53A61K31/5377A61P25/28
Inventor 胡春金辄刘晓平黄二芳徐赫男温志昌
Owner SHENYANG PHARMA UNIVERSITY
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