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A kind of preparation method of epinastine related substance

A technology for epilastine and related substances, applied in the direction of organic chemistry and the like, can solve the problems of long reaction time, complicated process, low purity epilastine solution and the like, and achieves a simple preparation process, low cost and high yield. Effect

Active Publication Date: 2021-03-16
HEFEI HUAFANG PHARMA SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] Chinese application publication number CN106749281A discloses a 3-amino-9H-diphenyl[c,f]imidazo[1,5-a]azepine (Epinastine impurity A) preparation method: first oxidize with 10-30% hydrogen peroxide, heat and react for 8-28h, repeatedly extract to obtain a lower purity epinastine solution, and then obtain epinastine impurity through chromatographic column purification ; but there is a long reaction time, using column separation, different ratios of elution machine elution and purification to obtain a product with a purity of more than 95%, the process is complicated, and it is difficult to quantify the preparation

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  • A kind of preparation method of epinastine related substance
  • A kind of preparation method of epinastine related substance
  • A kind of preparation method of epinastine related substance

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Experimental program
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Effect test

Embodiment 1

[0023] A preparation method of related substances of epinastine, comprising the steps of:

[0024] Step 1, take 0.01mol epinastine, 12ml N,N-dimethylformamide solution, 0.03mol DBU and 0.011mol CuCl2.2H2O and mix at room temperature for 3 hours;

[0025] Step 2, TLC detects the degree of reaction. After the reaction, add 30ml of water and 60ml of ethyl acetate successively, separate the ethyl acetate layer, extract the water layer with ethyl acetate twice, combine the organic layers and wash with saturated saline three times;

[0026] Step 3, drying with anhydrous sodium sulfate, suction filtration, and recovery of ethyl acetate under reduced pressure;

[0027] Step 4, using n-hexane-ethyl acetate for recrystallization and purification.

[0028] The above-mentioned recrystallization from n-hexane-ethyl acetate obtained 2.1 g of the epinastine impurity A, the recovery rate was 85%, and the purity of the epinastine impurity A was 97.2%.

[0029] refer to figure 1 Shown, Chemi...

Embodiment 2

[0031] A preparation method of related substances of epinastine, comprising the steps of:

[0032] Step 1, take 0.01mol epinastine, 10ml dimethyl sulfoxide, 1ml hydrochloric acid aqueous solution and 0.011mol ferric chloride and stir at room temperature for 2 hours;

[0033] Step 2, TLC detects the degree of reaction. After the reaction, add 30ml of water and 60ml of ethyl acetate successively, separate the ethyl acetate layer, extract the water layer with ethyl acetate twice, combine the organic layers and wash with saturated saline three times;

[0034] Step 3, drying with anhydrous sodium sulfate, suction filtration, and recovery of ethyl acetate under reduced pressure;

[0035] Step 4, using n-hexane-ethyl acetate for recrystallization and purification.

[0036] Wherein, the hydrochloric acid aqueous solution selects the hydrochloric acid solution that concentration is 10%.

[0037] The above-mentioned recrystallization from n-hexane-ethyl acetate obtained 2.05 g of epin...

Embodiment 3

[0039] Step 1, take 0.01mol epinastine, 20ml N,N-dimethylformamide solution, 0.05mol DBU and 0.02mol CuCl 2 .2H 2 O mixed and stirred at room temperature for 3 hours;

[0040] Step 2, TLC detects the degree of reaction. After the reaction, add 40ml of water and 80ml of ethyl acetate successively, separate the ethyl acetate layer, extract the water layer with ethyl acetate 4 times, combine the organic layers and wash with saturated saline three times;

[0041] Step 3, drying with anhydrous sodium sulfate, suction filtration, and recovery of ethyl acetate under reduced pressure;

[0042] Step 4, using n-hexane-ethyl acetate for recrystallization and purification.

[0043] The above recrystallization through n-hexane-ethyl acetate obtained 1.9 g of epinastine impurity A, the recovery rate was 76.9%, and the purity of epinastine impurity A was 97.3%.

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Abstract

The invention discloses a preparation method of an epinastine related substance and relates to the technical field of medicines. The preparation method comprises steps as follows: epinastine is takenas a raw material, an oxidizing agent, a catalyst and a reaction system solvent are added, the mixture is stirred uniformly, an organic solvent is added after the reaction ends, extraction, washing, drying and suction filtration under reduced pressure are sequentially performed, and the organic solvent is recovered. An epinastine impurity A with the purity up to 97% is obtained through oxidation preparation, separation and purification steps, and the method is simple in preparation process, low in cost and high in yield.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a 3-amino-9H-diphenyl[c,f]imidazo[1,5-a]azepine (Epinastine impurity A) preparation method. Background technique [0002] Epinastine hydrochloride (3-amino-9,13b-dihydro-1H-dibenzo[c,f]imidazo[1,5-a]azepine Hydrochloride, formula 1) is a histamine H1 receptor antagonist, which has inhibitory effects on histamine, leukotriene C4, PAF, and serotonin, and can also inhibit histamine, slow-reacting substance A (SRS-A) The release of chemical mediators can be clinically used for the prevention and treatment of allergic rhinitis, urticaria, eczema, dermatitis, skin pruritus, prurigo, psoriasis vulgaris accompanied by itching, and allergic bronchial asthma. Common adverse reactions are allergies, drowsiness, digestive system symptoms and abnormal liver function. [0003] The standard of epinastine hydrochloride included in European Pharmacopoeia version 8.7 contains two known impur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 黄学桂何勇方宗华于艳英吴宗好
Owner HEFEI HUAFANG PHARMA SCI & TECH
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