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Preparation method of anti-allergic drug bepotastine

A bepotastine and anti-allergic technology, which is applied in the field of synthesis of anti-allergic drugs, can solve the problems of cumbersome operation, high cost, and difficulty in large-scale preparation, and achieve the effect of low cost and simple synthetic route

Inactive Publication Date: 2016-09-07
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the above method has the disadvantages of cumbersome operation or high cost, and it is difficult to prepare on a large scale.

Method used

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  • Preparation method of anti-allergic drug bepotastine
  • Preparation method of anti-allergic drug bepotastine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of (S)-N-tert-butoxycarbonyl-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (formula III)

[0026]

[0027] Dissolve 21.9 g (0.1 mol) of compound (S)-(4-chlorophenyl)(2-pyridyl)-methanol formula (Formula II) in 160 mL of tetrahydrofuran, and add 60% mass fraction of hydrogenation solution in batches under stirring Sodium 41g (0.1mol), stirred for 2 hours until no bubbles emerged, and the reaction liquid was added dropwise to the solution of N-tert-butoxycarbonyl-4-bromopiperidine 26.4g (0.1mol) under ice bath cooling, and added dropwise After completion, the temperature was gradually raised to room temperature under stirring for 5 hours, the reaction solution was added to 200mL saturated ammonium chloride solution, stirred for 30 minutes, the reaction solution was extracted twice with 300mL ethyl acetate, the organic phases were combined, and dried over anhydrous sodium sulfate for 2 hours , filtered, and the mother liquor was rotary evaporated to dryne...

Embodiment 2

[0029] Preparation of (S)-N-tert-butoxycarbonyl-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (formula III)

[0030] The sodium hydride in embodiment 1 is replaced with the sodium ethylate of equimolar amount, other operations are the same as embodiment 1, and product yield is 73%.

Embodiment 3

[0032] Preparation of (S)-N-tert-butoxycarbonyl-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (formula III)

[0033] The tetrahydrofuran in Example 1 was replaced with an equivalent amount of N,N-dimethylformamide, and other operations were the same as in Example 1, and the product yield was 88%.

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Abstract

The invention discloses a preparation method of an anti-allergic drug bepotastine, and relates to the technical field of anti-allergic drugs. The technical point of the invention is that a compound (S)-(4-chlorophenyl)(2-pyridyl)-methanol (formula II) is adopted as an initial raw material and is subjected to a reaction with N-tert-butoxycarbonyl-4-halopiperidine, such that a compound (S)-N-tert-butoxycarbonyl-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (formula III) is obtained; under an acidic condition, the protecting group of the compound represented by the formula (III) is removed, such that a compound (S)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine (formula IV) is obtained; the compound represented by the formula (IV) is subjected to a nucleophilic substitution reaction with 4-chlorobutanamide, such that a compound (S)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]-piperidinyl]-butyramide (formula V) is obtained; the amide group of the compound represented by the formula (V) is hydrolyzed, such that the target product which is the anti-allergic drug bepotastine is obtained. The method provided by the invention has the advantages of simple synthesis route and low cost, and is suitable for large-scale production of the optically pure anti-allergic drug bepotastine.

Description

technical field [0001] The invention belongs to the technical field of synthesis of antiallergic drugs, and in particular relates to a preparation method of the antiallergic drug bepotastine. Background technique [0002] Bepotastine is an antiallergic drug developed by Ube Industries in Japan. It was first launched in Japan in 2000 under the trade name Talion. Bepotastine is a histamine H1 receptor antagonist, which can be used to treat allergic diseases such as allergic rhinitis. It acts quickly and has high selectivity. It has no adverse reaction of sedation caused by previous antiallergic drugs, and has a good curative effect. It can also inhibit the infiltration of eosinophils caused by antigens and reduce allergic inflammation. The patent application number CN97181039.7 discloses an acid addition salt of an optically active piperidine compound and a preparation method thereof. The method first obtains (S)-4-[(4-chlorophenyl)( 2-pyridyl)methoxy]piperidine, and then th...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCY02P20/55C07D401/12
Inventor 杨守宁杨嬅嬿李伟杨林余绍宁
Owner HENAN NORMAL UNIV
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