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Xanthiphenyl ketamine or its salt and its preparing process

A technology of piperphentonamine salt and piperphentonamine salt, which is applied in the field of piperphentonamine, piperphentonamine salt and its preparation, can solve the problems of long-term effects that are yet to be seen, enhancement of myocardial contractility, intracellular Calcium overload and other problems, to achieve the effect of resisting reperfusion injury, treating heart failure, and having low toxic and side effects

Inactive Publication Date: 2003-02-12
WUXI JIMIN KEXIN SHANHE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, cardiac glycosides, catecholamines, phosphodiesterase inhibitors (PDEIs) and other types of cardiotonic drugs have relatively large toxic reactions, because they mainly increase the concentration of intracellular calcium ions to achieve the effect of enhancing myocardial contractility. Arrhythmogenic risk, prone to intracellular calcium overload
Diuretics are often used as the first choice for heart failure, but they are prone to side effects such as electrolyte disturbances
Recent studies have shown that angiotensin-converting enzyme inhibitors (ACEI) can treat congestive heart failure and resist myocardial ischemia and reperfusion injury, and its long-term effect remains to be seen

Method used

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  • Xanthiphenyl ketamine or its salt and its preparing process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Adopt the following method to synthesize N-methyl piperonyl ethylamine hydrochloride:

[0046]Put 1.09mol of piperonylethylamine (intermediate of Northeast Pharmaceutical Factory) and 1.96mol of benzaldehyde in a 1000ml round-bottomed flask, mix well, release a lot of heat, add 300ml of absolute ethanol and mix well, add zeolite, and heat with an electric heating cap , reflux reaction for 18 hours, concentrated under reduced pressure to remove ethanol, and then concentrated under reduced pressure with an oil pump to remove unreacted benzaldehyde to obtain a reddish-brown oily substance. After cooling to room temperature, add 200ml toluene and 1.09mol dimethyl sulfate. Keep the reaction at about 120°C for 30 minutes, let stand at room temperature to cool, pour off the upper toluene layer after layering, then add 300ml of 75% ethanol, and then reflux for 30 minutes to obtain a dark brown-red opaque liquid. Add 10ml of distilled water, shake well, and under stirring, use a...

Embodiment 2

[0053] Put 17.2g (0.08mol) of N-methylpiperethylamine hydrochloride and 24g (0.8mol) of paraformaldehyde in a 500ml round bottom bottle, add 200ml of absolute ethanol and 1.5ml of concentrated hydrochloric acid to make the pH about 3 -4, the temperature of the oil bath is 100°C, heat and stir until the solid is completely dissolved, then heat and stir for about 20 minutes, cool slightly, add 16.2g ((0.1mol) of p-hydroxybenzylideneacetone, reflux and stir for about 6.0 hours, the reaction Slowly separate out solid in the process, until all solidify in the reaction bottle.Detect R with TLC f =0.38 (developing agent: CH 2 Cl 2 :CH 3 OH:HCOOH=10:0.8:0.08), the reaction is basically complete. Filtered, the solid was repeatedly washed with absolute ethanol, and dried. A pale yellow solid was obtained. The solid was recrystallized with 95% ethanol to obtain a light yellow powdery solid, which was then cooled, filtered, and washed with absolute ethanol to obtain a near-white powd...

Embodiment 3

[0055] Put 25.8g (0.12mol) of N-methylpiperethylamine hydrochloride and 36g (1.2mol) of paraformaldehyde in a 500ml round bottom bottle, add 320ml of absolute ethanol and 2.0mol of concentrated hydrochloric acid to make the pH about 4 , the oil bath temperature is 90°C, heat and stir until all the solids are dissolved, then heat and stir for 10 minutes, cool slightly, add 16.2g (0.1mol) of p-hydroxybenzylidene acetone, reflux and stir for about 9.5 hours, and slowly Solids were precipitated until all solidified in the reaction bottle. Detection of R by TLC f =0.38 (developing agent: CH 2 Cl 2 :CH 3 OH:HCOOH=10:0.8:0.08), the reaction is basically complete. After filtration, the solid was repeatedly washed with absolute ethanol and dried to obtain a pale yellow solid. The solid was recrystallized with ethanol to obtain a light yellow powdery solid of piperphentonamine hydrochloride, which was then cooled, filtered, and washed with absolute ethanol to obtain a nearly white ...

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Abstract

A process for preparing xanthiphenyl ketoamine or its salt includes such steps as reflux reaction of p-hydroxy benzylidenacetone, N-methyl piperethanamine hydrochloride and polyformaldehyde in absolute alcohol for 6-9.5 hr until fully solidifying, filtering, washing, recrystallizing 1-2 times, then drying to obtain xanthiphenyl ketoamine hydrochloride, neutralizing to obtain xanthiphenyl ketoamine, and reaction on acid to obtain the corresponding salt. Its advantages are simple process, high output rate and high purity.

Description

field of invention [0001] The present invention relates to a class of novel compounds with cardiotonic and vasodilation effects and a preparation method thereof. Specifically, the present invention relates to piperphentonamine, piperphentonamine salt and a preparation method thereof. Background technique [0002] Heart failure is the terminal stage of cardiovascular disease with high mortality. Myocardial infarction and myocardial reperfusion injury are important causes of heart failure. Experimental studies at home and abroad have shown that calcium antagonists and free radical scavengers can treat myocardial infarction and resist reperfusion injury. However, most calcium antagonists inhibit myocardial contractility and reduce cardiac function, so their clinical application is limited. Free radical scavengers have no direct effect on cardiac function, and their clinical effects have not been confirmed. [0003] The treatment principle of heart failure is to strengthen th...

Claims

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Application Information

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IPC IPC(8): C07D317/48
Inventor 周力践衷小惠刘铁球
Owner WUXI JIMIN KEXIN SHANHE PHARMA
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