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Phenoxy alkyl piperazine compounds, preparation method thereof and medicinal use thereof

A technology of phenoxyalkylpiperazine and compound, which is applied in the field of medicinal chemistry, can solve problems such as neglect, and achieve the effects of easy-to-obtain raw materials, simple operation and post-processing, and abundant raw materials

Active Publication Date: 2013-04-10
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the other hand, traditional arrhythmia drugs are mostly aimed at the ventricular arrhythmia that has begun to deteriorate, ignoring the control of atrial arrhythmia symptoms in the early stage of arrhythmia disease and the prevention of the deterioration from atrial arrhythmia to ventricular arrhythmia. prevention

Method used

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  • Phenoxy alkyl piperazine compounds, preparation method thereof and medicinal use thereof
  • Phenoxy alkyl piperazine compounds, preparation method thereof and medicinal use thereof
  • Phenoxy alkyl piperazine compounds, preparation method thereof and medicinal use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Thiophene-2-(4-(2-(4-methylphenoxy)ethyl)piperazine)methanone

[0094]

[0095] (1) Preparation of 1-piperazine-(2-thiophene)methanone hydrochloride

[0096] Thiophene-2-carboxylic acid (0.06 mol) was dissolved in dichloromethane, thionyl chloride (0.15 mol) was added, stirred at 5°C for 2h, then heated to 40°C and stirred for 4h. The solvent was evaporated to dryness, absolute ethanol (100 mL) was added, a solution of piperazine (0.12 mol) in absolute ethanol (40 mL) was added dropwise, and the mixture was refluxed for 5 h. Evaporate the solvent to dryness, add water, adjust the pH to 8-9 with 10% sodium hydroxide solution, extract with chloroform (50 mL x 3 times), and dry the organic layer with anhydrous magnesium sulfate. Filtrate, pass through hydrochloric acid gas, a white solid precipitates out, filter, and dry under infrared light to obtain 2.19g of product, yield: 16%, melting point: 239-241°C.

[0097] (2) Preparation of 1-(2-bromoethoxy)-4-methylbenzene ...

Embodiment 2

[0102] Thiophene-2-(4-(2-(2-methylphenoxy)ethyl)piperazine)methanone hydrochloride

[0103]

[0104] (1) Preparation of 1-(2-bromoethoxy)-4-methylbenzene

[0105] Prepared according to step (2) in Example 1, substituting o-cresol for p-cresol, and distilled under reduced pressure to obtain a colorless oil, yield: 56.4%.

[0106] (2) Preparation of title compound

[0107] Prepared according to the method of step (3) in Example 1, 1-(2-bromoethoxy)-4-methylbenzene is substituted for 1-(2-bromoethoxy)-4-methylbenzene, purified by column chromatography , evaporate the eluate to dryness, add 20mL ethanol, pass into hydrochloric acid gas, yield: 45.5%, melting point: 207-209 ℃, EI-MS m / z 330 ([M] + ), 1 H-NMR (D 2 O)δ2.26(d,3H,-PhC H 3 ), 3, 47(s, 4H, -N(C H 2 CH 2 ) 2 NCO-), 3.6(t, 2H, J=4.5Hz, -NC H 2 CH 2 O-), 4.05(s, 4H, -N(CH 2 C H 2 ) 2 NCO-), 4.37(t, 2H, J=4.5Hz, -NCH 2 C H 2 O-), 6.86-6.92(m, 3H, Ar-H), 7.12-7.24(m, 2H, Ar-H), 7.28(d, 1H, J=3.3 Hz, Ar-...

Embodiment 3

[0109] Thiophene-2-(4-(2-(4-methoxyphenoxy)ethyl)piperazine)methanone

[0110]

[0111] (1) Preparation of 1-(2-bromoethoxy)-4-methoxybenzene

[0112] Prepared according to step (2) in Example 1, substituting p-methoxyphenol for p-cresol, yield: 39%, melting point: 51-53°C.

[0113] (2) Preparation of title compound

[0114] Prepared by the method of step (3) in Example 1, replacing 1-(2-bromoethoxy)-4-methylbenzene with 1-(2-bromoethoxy)-4-methoxybenzene, the yield : 59.7%, melting point: 82-84°C, EI-MS m / z 346 ([M] + ), 1 H-NMR (CDCl 3 )δ2.63(t, 4H, J=4.8Hz, -N(C H 2 CH 2 )2 NCO-), 2.83(t, 2H, J=5.4Hz, -NC H 2 CH 2 O-), 3.79(t, 7H, -N(CH 2 C H 2 ) 2 NCO-,-PhOC H 3 ), 4.08(t, 2H, J=5.4Hz, -NCH 2 C H 2 O-), 6.84(m, 4H, Ar-H), 7.02-7.06(m, 1H, Ar-H), 7.26-7.29(m, 1H,, Ar-H), 7.45(d, 1H, J= 5.1Hz, Ar-H).

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Abstract

The invention relates to the field of medical chemistry and particularly relates to phenoxy alkyl piperazine compounds (I) or (II), a preparation method thereof, a medicinal preparation containing the same and medicinal use thereof. Ar, L and R are defined in the description. Pharmacological tests prove that the compounds have certain blocking activity for voltage-gated potassium channels. Therefore, the compounds and the pharmaceutical preparations of the compounds can be used for treating series of diseases caused by dysfunction of potassium channels, such as arrhythmia and hypoxicischemic brain damage.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of phenoxyalkylpiperazine compounds, a preparation method thereof, a pharmaceutical preparation thereof and a medical application thereof. Background technique [0002] Arrhythmia is a major disease that seriously threatens people's health and quality of life. The sales of antiarrhythmic drugs are increasing year by year, and the patients are getting younger. Therefore, research on antiarrhythmic drugs has huge social and economic benefits. benefit. [0003] Antiarrhythmic drugs can be divided into four categories according to different mechanisms of action. Currently, Class III antiarrhythmic drugs—potassium ion channel blockers are mainly used in clinical applications, including amiodarone, dofetilide, and sotalol etc., its electrophysiological effect is to prolong the duration of myocardial action potential and the effective refractory period. However, currently cl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/38C07D277/46C07D295/192C07D307/68C07D295/15C07D233/88C07D213/75A61K31/496A61K31/495A61P9/06A61P9/10
Inventor 尤启冬杨倩郭小可狄斌汤依群
Owner CHINA PHARM UNIV
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