Chemical synthesis method for epinastine

A chemical synthesis, epinastine technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, drug combination, etc., can solve the problems that are not suitable for industrial production, and achieve high reaction yield, less by-products, and simple preparation Effect

Inactive Publication Date: 2008-02-27
HANGZHOU LONGSHAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This line uses cyanide and precious lithium tetrahydrogen for reduction, which is not suitable for industrial production

Method used

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  • Chemical synthesis method for epinastine
  • Chemical synthesis method for epinastine
  • Chemical synthesis method for epinastine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Amination reaction

[0022] In a 500ML reactor, put 20 grams of starting material 6-chloromethyl-11-dihydro-dibenzo[b, e]azepine, 300 milliliters of absolute ethanol, feed saturated ammonia gas,- React at 20°C for 24 hours, take the reaction solution for liquid phase detection, when the product content is greater than 95%, stop the reaction, add water and dichloromethane for extraction, and recover the solvent to obtain the product 6-aminomethyl-11-dihydro-diphenyl And [b, e] azepine 17.5 g (HPLC.99%, yield 95%).

[0023] (2) Reduction reaction

[0024] In a 500ML reactor, put 20 grams of raw materials 6-aminomethyl-11-dihydro-dibenzo[b, e]azepine, 300 milliliters of methanol, 6 grams of potassium borohydride, and react at 0°C for 36 hour, take the reaction liquid liquid phase detection, when the raw material is less than 1%, the reaction ends. Extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, and recovered the solvent to obt...

Embodiment 2

[0029] (1) Amination reaction

[0030] In a 500ML reactor, put 30 grams of starting materials 6-chloromethyl-11-dihydro-dibenzo[b, e]azepine, 400 milliliters of methanol, and feed 20 ml of concentrated ammonia water, at 40°C After reacting for 10 hours, take the liquid phase of the reaction solution for detection. When the product content is greater than 95%, stop the reaction, add water and dichloromethane for extraction, and recover the solvent to obtain the product 6-aminomethyl-11-dihydro-dibenzo[b, e] 26 grams of azepines (HPLC.99%, yield 94.5%).

[0031] (2) Reduction reaction

[0032] In a 500ML reactor, put 30 grams of raw materials 6-aminomethyl-11-dihydro-dibenzo[b, e]azepine, 300 milliliters of DMF, 5 grams of 5% palladium carbon, and feed hydrogen at a pressure of 0 MPa , reacted at 80° C. for 24 hours, took the liquid phase of the reaction solution for detection, and when the raw material was less than 1%, the reaction ended. Extract with dichloromethane, wash ...

Embodiment 3

[0037] (1) Amination reaction

[0038] In the 500ML reactor, drop into starting material 6-chloromethyl-11-dihydro-dibenzo[b, e] 30 grams of azepines, 400 milliliters of ethylene glycol monomethyl ether, pass into liquid ammonia, React at 80°C for 2 hours, take the reaction liquid for liquid phase detection, when the product content is greater than 95%, stop the reaction, add water and dichloromethane for extraction, and recover the solvent to obtain the product 6-aminomethyl-11-dihydro-diphenyl And [b, e] azepine 27 g (HPLC.99%, yield 95%).

[0039] (2) Reduction reaction

[0040] In a 500ML reactor, put 20 grams of raw materials 6-aminomethyl-11-dihydro-dibenzo[b, e]azepine, 300 milliliters of absolute ethanol, and 4.5 grams of sodium borohydride at 60°C After reacting for 4 hours, take the liquid phase of the reaction solution for detection, and when the raw material is less than 1%, the reaction is over. Extracted with dichloromethane, washed with water, dried over anhy...

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Abstract

The invention discloses a new chemical synthesizing method of yipisidin, which comprises the following steps: ammonifying 6-chloromethyl-11-dihyrogen-dibenz [b,e] aza to generate 6-aminomethyl-11-dihydrogen-dibenz [b,e] aza; reducing the 6-aminomethyl-11-dihydrogen-dibenz [b,e] aza into 6-aminomethyl-6,11-dihydrogen-5H-dibenz [b,e] aza; generating the product through cyanogen bromide to loop. The invention simplifies the making method with little by-product, which improves the receiving rate by 69% with high purity (HPLC. 99. 0%) for industrial manufacturing.

Description

technical field [0001] The invention relates to a novel chemical synthesis method of epinastine. It specifically relates to a method for synthesizing epinastine by using 6-chloromethyl-11-dihydro-dibenzo[b,e]azepine as a starting material through ammoniation reaction, reduction reaction and ring closure reaction . Starting material 6-chloromethyl-11-dihydro-dibenzo [b, e] azepine can be according to J.Am.Chem.Soc. Magazine 1970, Vol.13, P35 published literature method prepared. Background technique [0002] Epinastine is suitable for skin allergic reactions and has good curative effect on allergic rhinitis and allergic bronchial asthma. Wide range of clinical application departments. It has high selectivity and affinity for H1 receptors, and its anti-allergic effect is stronger than that of traditional drugs. With multiple anti-allergic mechanisms, it can eliminate allergic symptoms more thoroughly. The onset of effect is more rapid, and the pain of patients can be rel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/55A61P37/08
Inventor 王彬峰谭忠宇
Owner HANGZHOU LONGSHAN CHEM CO LTD
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