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A kind of technique of synthesizing cetirizine hydrochloride

A cetirizine hydrochloride, process technology, applied in the field of pharmaceutical chemical synthesis, can solve the problems of compound IX source difficulty, difficult control of reaction conditions, complicated operation, etc., and achieve the effect of low cost, good product quality and simple operation

Active Publication Date: 2016-04-13
CHONGQING WERLCHEM FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0031] However, the source of compound IX is difficult and expensive
[0032] The subsequent use of hydrogen peroxide will bring great harm to safety. In production, the pH value of the reaction solution must be strictly controlled. The reaction conditions are difficult to control and the operation is very complicated.

Method used

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  • A kind of technique of synthesizing cetirizine hydrochloride
  • A kind of technique of synthesizing cetirizine hydrochloride
  • A kind of technique of synthesizing cetirizine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0062]Dissolve 37.4 grams of hydroxyzine in 350 milliliters of dichloromethane, add 1.2 grams of TEMPO, and stir to dissolve; then add 5.95 grams of potassium bromide, 2.78 grams of tetrabutylammonium chloride and 85 grams of deionized water; stir and cool to -5 Slowly add sodium hypochlorite aqueous solution dropwise, during which the reaction temperature is controlled at about -5 degrees; HPLC monitors the oxidation to the end, stop adding sodium hypochlorite dropwise, and quickly add 80 grams of 15% sodium thiosulfate aqueous solution, stir for 30 minutes and then separate layers ; The organic layer was washed successively with saturated aqueous sodium chloride solution and deionized water, and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure; finally, 36.2 g of crude aldehyde intermediate was obtained.

Embodiment 2

[0064] Dissolve 37.4 grams of hydroxyzine in 448 milliliters of ethyl acetate, add 1.6 grams of TEMPO, and stir to dissolve; then add 5.95 grams of potassium bromide, 2.78 grams of tetrabutylammonium chloride and 120 grams of deionized water; stir and cool to -5 Slowly add sodium hypochlorite aqueous solution dropwise, during which the reaction temperature is controlled at about -3 degrees; HPLC monitors the oxidation to the end, stop adding sodium hypochlorite dropwise, and quickly add 80 grams of 15% sodium thiosulfate aqueous solution, stir for 30 minutes and then separate layers ; The organic layer was successively washed with saturated aqueous sodium chloride solution and deionized water, and then dried over anhydrous sodium sulfate; filtered, and the solvent was evaporated under reduced pressure. Finally, 37.1 g of crude aldehyde intermediate were obtained.

Embodiment 3

[0066] Dissolve 3.2 grams of pyridine sulfur trioxide complex in 25 milliliters of DMSO, and cool down to -10 degrees after nitrogen replacement; dissolve 3.75 grams of hydroxyzine in 4.5 grams of triethylamine and 10 milliliters of DMSO, and slowly drop the solution into the reaction solution of pyridine sulfur trioxide complex; during the period, the reaction temperature was controlled between -5°C and 10°C; after the dropwise addition was completed, it was returned to 25°C for 5 hours; after the reaction was monitored by HPLC, 150 ml of dichloro methane, and then the reaction solution was washed three times with deionized water; the obtained organic phase was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 4.3 g of crude aldehyde intermediate.

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Abstract

A new technology for synthesizing cetirizine hydrochloride. The technology includes following steps: oxidizing hydroxyzine, which is used as a raw material, into a substance containing an aldehyde group; further oxidizing the substance containing the aldehyde group into cetirizine; and finally performing a salification and purification process to obtain the cetirizine hydrochloride. A total yield of the synthetic method is higher than 80%. Meanwhile, the method is simple in operation, is short in production period, is low in energy consumption and cost, is little in waste water, waste gas and residues and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical synthesis, and relates to a preparation method of a crude drug, more specifically a synthesis method of cetirizine hydrochloride. Background technique [0002] Cetirizine hydrochloride (Compound I) was developed by Belgian UCB Company and launched in 1987. [0003] As a second-generation H1 receptor antagonist, cetirizine hydrochloride has the characteristics of high selectivity for H1 receptors, long half-life, no obvious sedative effect, and few adverse reactions in the central nervous system. [0004] At present, it is widely used in the treatment of allergic diseases such as respiratory system and skin, and the most typical ones are the treatment of urticaria, atopic dermatitis, allergic rhinitis, non-seasonal allergic rhinitis, hay fever, allergic asthma, Diseases such as pharyngitis with increased airway reactivity and conjunctivitis with itchy eyes. [0005] The drug has been record...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/088
CPCC07D295/088
Inventor 杨冰
Owner CHONGQING WERLCHEM FINE CHEM
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