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Improved method for synthesizing ranolazine

A synthesis method and technology of ranolazine, applied in the field of medicinal chemistry, can solve the problems of low total yield, unsuitable for industrial production, many steps, etc., and achieve the effects of reducing production cost and reducing reaction time.

Active Publication Date: 2012-07-11
FUREN PHARMA GROUP +1
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Problems solved by technology

The advantage of synthetic route 3 is to avoid using a large amount of piperazine, and the disadvantage is that there are many steps, the total yield is low, and it is not suitable for industrial production
In a word, the application value of route 2 is greater, but the total yield is lower; in addition, the purification of ranolazine is mostly separated by silica gel column, which is not conducive to industrial production, and the yield of the method of recrystallization using a single solvent or a mixed solvent is not too high

Method used

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  • Improved method for synthesizing ranolazine
  • Improved method for synthesizing ranolazine
  • Improved method for synthesizing ranolazine

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Embodiment Construction

[0025] In order to better implement the present invention, the present invention is further described by giving examples, but the examples are not limitations of the present invention.

[0026] (1) Preparation of 2-(2-methylphenoxymethyl)oxirane

[0027] Add 49.6g (0.4mol) of o-methoxyphenol, 185g (2.0mol) of epichlorohydrin, 110.6g (0.4mol) of potassium carbonate, and 0.5g of benzyltriethylammonium chloride (TEBA) into a 500ml reaction bottle . Heat up to 70°C with stirring, react for 2 hours, cool to room temperature, filter, wash the filter cake with 60ml×2 epichlorohydrin, combine the filtrate, recover epichlorohydrin at 60-120°C / 50mmHg, collect 136.0-138.0°C / 30mmHg Distillation, the product 61.9g was obtained, the yield was 86.0%.

[0028] (2) Preparation of 2-chloro-N-(2,6 benzhydryl)acetamide

[0029] Put 36.4g (0.30mol) of 2,6-dimethylaniline, 600ml of dichloromethane, 31.8g (0.3mol) of sodium carbonate and 300ml of water into a 2000ml reaction bottle. Control t...

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Abstract

The invention discloses an improved method for synthesizing an antianginal medicine ranolazine and belongs to the field of pharmaceutical chemistry. The method comprises the following steps of: amidating 2,6-dimethylaniline which is taken as a raw material, and alkylating to obtain N-(2,6-dimethylphenyl)-2-(1-piperazino)-acetamide; and reacting the N-(2,6-dimethylphenyl)-2-(1-piperazino)-acetamide and 2-(2-methylphenoxymethyl)ethylene oxide which is obtained by reaction of 2-methoxyphenol and epichlorohydrin to obtain crude ranolazine, and recrystallizing to obtain refined ranolazine. A reaction solvent, the molar ratio of raw materials, a phase transfer catalyst, a recrystallization solvent and the like are optimized; and the improved method is convenient to operate and is suitable for industrialized production, the production cost is reduced, and the yield is improved.

Description

technical field [0001] The invention relates to a synthesis method of an antiangina drug, in particular to a synthesis method of ranolazine, and belongs to the field of medicinal chemistry. Background technique [0002] Ranolazine is a new type of anti-anginal drug developed by Syntex Corporation of the United States. Its chemical name is: (±) N-(2,6-dimethylphenyl)-4-[2-hydroxyl-3-(2 -methoxyphenoxy)-propyl]-1-piperazineacetamide. Ranolazine was approved by the U.S. Food and Drug Administration (FDA) in 2006 for the treatment of chronic angina pectoris. It can provide myocardial protection at the cellular level by improving myocardial energy metabolism. It has an effect; its mechanism of action is to inhibit the oxidation of some fatty acids, so that the oxidative metabolism of fatty acids in the heart is changed to the oxidative metabolism of glucose, thereby reducing the oxygen consumption of the heart without causing changes in heart rate and blood pressure. Clinically...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/15
Inventor 陈水库张方杰李烂孟强丁红强马杰崔浩陈永强程东杰刘志军陈军
Owner FUREN PHARMA GROUP
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