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Cimetidine synthesis process

A synthesis process and cimetidine technology, which is applied in the field of cimetidine synthesis technology, can solve problems such as adverse environmental impact, high synthesis cost, human body harm, etc., achieve less waste, strong reactivity and selectivity, reduce Effects of damage to the human body and the environment

Pending Publication Date: 2019-10-25
HEBEI KANGTAI PHARMA
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  • Abstract
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Problems solved by technology

[0002] Cimetidine, listed in 1975, is the first selective H2-receptor antagonist, used for the treatment of peptic ulcer, can significantly inhibit food, histamine, pentagastrin, caffeine and insulin stimulation It can cause gastric acid secretion and reduce its acidity, which can prevent and protect corrosive gastritis caused by chemical stimulation, and has obvious curative effect on stress gastric ulcer and upper gastrointestinal bleeding. It has been clinically used for the treatment of peptic ulcer. Familiar with it, but the existing production process at home and abroad is accompanied by foul smell in the production process of cimetidine, which is harmful to the human body and prone to adverse effects on the environment, and its synthesis cost is relatively high

Method used

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specific Embodiment approach

[0039] Below in conjunction with the examples, the specific implementation of the present invention will be further described in detail. The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention.

[0040] Cimetidine synthesis technique of the present invention, its operational route is as follows

[0041]

[0042] And, its synthesis process comprises the following steps:

[0043] (1) The first intermediate and the photocatalyst are mixed and dissolved in the reaction solvent;

[0044] (2) and adding the second intermediate to the reaction solution in step (1), after mixing uniformly, a clear solution is obtained;

[0045] (3) Use a light source to irradiate the clear solution obtained in step (2), and cooperate with stirring until the HPLC shows that the first intermediate reacts completely;

[0046] (4) After the reaction finishes, carry out concentration treatment to remove solvent, and use wat...

Embodiment 1

[0048] The first intermediate (0.54g, 2.0mmol) and EosinY (65mg, 0.1mmol) were dissolved in tert-butanol (20mL) and added to thiol (0.47g, 3.0mmol) to obtain a clear solution, which was then illuminated with visible light. Under irradiation, heat to 70°C and stir for 24h. HPLC shows that the first intermediate is completely reacted. After the reaction, wash with saturated sodium bicarbonate (50ml), extract with ethyl acetate (3╳50mL), and combine the organic phases. Dry over anhydrous sodium sulfate, concentrate, and use silica gel column chromatography (dichloromethane / methanol) to obtain cimetidine as a white powder (0.43g, 85%) with a melting point of 139°C to 141°C.

Embodiment 2

[0050] The first intermediate (2.7g, 20mmol) and Ir(ppy) 3 (150mg) was dissolved in ethyl acetate (150mL) and added to disulfide (3.3g, 21mmol) to obtain a clear solution, then, under the irradiation of blue LED light (~390nm), stirring at room temperature for 15h, HPLC It shows that the reaction of the first intermediate is complete. After the reaction, the solvent is concentrated and removed, and cimetidine is recrystallized from isopropanol and water to obtain cimetidine as a white powder (4.9 g, 91%).

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Abstract

The invention relates to the technical field of biomedicine, in particular to a cimetidine synthesis process. The cimetidine synthesis process has high efficiency, damage to the human body and the environment can be reduced, and meanwhile the synthesis cost can be reduced. The synthesis process comprises the following steps: (1) mixing a first intermediate with a photocatalyst, and dissolving theobtained mixture in a reaction solvent; (2) adding a second intermediate to the reaction solution obtained in the step (1), and performing uniform mixing so as to obtain a clear solution; (3) using alight source to irradiate the clear solution obtained in the step (2), and performing coordinated stirring until it is shown through HPLC that the first intermediate reacts completely; and (4) performing concentration treatment so as to remove the solvent after completion of the reaction, and performing recrystallization by using water and isopropanol or ethanol so as to obtain cimetidine white powder.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a synthesis process of cimetidine. Background technique [0002] Cimetidine, listed in 1975, is the first selective H2-receptor antagonist, used for the treatment of peptic ulcer, can significantly inhibit food, histamine, pentagastrin, caffeine and insulin stimulation It can cause gastric acid secretion and reduce its acidity, which can prevent and protect corrosive gastritis caused by chemical stimulation, and has obvious curative effect on stress gastric ulcer and upper gastrointestinal bleeding. It has been clinically used for the treatment of peptic ulcer. Familiar with, but existing domestic and international production technology is all accompanied by the foul smell in the production process to cimetidine, is harmful to human body, and easily produces bad influence to environment, and its synthesis cost is higher simultaneously. Contents of the invention [0003] In...

Claims

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Application Information

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IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 李金岭孙双林叶家峰
Owner HEBEI KANGTAI PHARMA
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