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Preparation method of atracurium besilate intermediates

A technology for atracurium besylate and intermediates, which is applied in the field of preparation of atracurium besylate intermediates, can solve the problems of high equipment requirements, high raw material costs, harsh operating conditions, and high labor intensity. Achieve the effect of being convenient for industrialized production, low cost and high product purity

Inactive Publication Date: 2010-09-29
TIANJIN WEIJIE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As can be seen from the above formula, the above synthetic method involves the compound 4,10-dioxo-3,11-dioxo-1,12-tridecene as an intermediate, because the synthesis of this intermediate is difficult , so the synthesis route is long, the operating conditions are harsh, the labor intensity is high, the post-reaction treatment is difficult, and the equipment requirements and raw material costs are high

Method used

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  • Preparation method of atracurium besilate intermediates
  • Preparation method of atracurium besilate intermediates
  • Preparation method of atracurium besilate intermediates

Examples

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Embodiment 1

[0015] Dissolve 11.5g of R-tetrahydropapaverine-N-acetyl-L-glutamic acid in an appropriate amount of water, then adjust the pH value to 11 with ammonia water, extract with toluene, and then add 5.8g of methyl acrylate and 70ml of methanol , heated to reflux under stirring conditions for 1.5 hours, then cooled to room temperature, desolvated, filtered, and the filtrate was washed with ether to obtain white solid R-3-[1-(3,4-dimethoxybenzyl) -6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline]-methyl acrylate 8.9g;

[0016] In the above 3.5g R-3-[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline]-acrylic acid methyl Add 0.43g of pentanediol to the ester, then add 0.05g of potassium tert-butoxide and 100ml of toluene, heat to reflux for 3 hours under stirring conditions, and distill off the azeotrope of methanol and toluene at the same time, then cool to room temperature, wash with water, and the organic phase Drying, desolventization, a yellow viscous substance was...

Embodiment 2

[0018] Dissolve 12.0g of S-tetrahydropapaverine-N-acetyl-L-glutamic acid with an appropriate amount of water, then adjust the pH value to 11 with ammonia water, extract with toluene, and then add 6.2g of ethyl acrylate and 70ml of methanol , heated to reflux under stirring conditions for 1.5 hours, then cooled to room temperature, desolvated, filtered, and the filtrate was washed with ether to obtain white solid S-3-[1-(3,4-dimethoxybenzyl) - 9.2 g of ethyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline]-acrylate.

[0019] In the above 7.2g S-3-[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline]-acrylic acid ethyl Add 0.88g of pentylene glycol to the ester, then add 0.10g of potassium tert-butoxide and 200ml of toluene, heat and reflux for 3 hours under stirring conditions, and distill off the azeotrope of ethanol and toluene at the same time, then cool to room temperature, wash with water, and the organic phase Drying, desolventization, a yellow viscous subs...

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Abstract

The invention discloses a preparation method of atracurium besilate intermediates, comprising the following steps of: reacting tetrahydropapaverine with methyl acrylate or ethyl acrylate in an organic solvent, then reacting the tetrahydropapaverine with pentanediol under alkali catalysis, and finally reacting with oxalic acid addition salts to prepare (1R, 1'R), (1S, 1'S) and (1R, 1'S)-4,10-dioxy-3,11-dioxo tridecylene-1,13-bi-[1-(3,4-dimethoxy benzyl) -6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline] dioxalate. Because an intermediate 4,10-dioxy-3,11-dioxo-1,12-tridecylene with large synthesis difficulty is avoided in the method, the preparation method has the advantages of simple process, mild condition, high purity of products, high yield, lower cost and convenient industrial production.

Description

technical field [0001] The present invention relates to a kind of preparation method of atracurium besylate intermediates, in particular to a kind of (1R, 1`R), (1S, 1`S) and (1R, 1`S)-4, 10-Dioxy-3,11-dioxotridecene-1,13-bis-[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2 , The preparation method of 3,4-tetrahydroisoquinoline] dioxalate. Background technique [0002] Cis-atracurium besylate is a highly selective, non-depolarizing neuromuscular blocking agent developed after atracurium besylate. Fenman elimination) degrades naturally and decomposes at plasma pH and body temperature to produce active substances. The termination of the neuromuscular blocking effect of the blocker does not depend on the metabolism and excretion of the liver and kidney, so the action time will not be affected by the damage of the kidney, liver and circulatory respiratory system, and is mainly used for anesthesia in various surgical operations When the skeletal muscle is relaxed, it is convenient t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/20
Inventor 宋洪海叶志海孙致远赵连营陈继德施欢乐胡春艳
Owner TIANJIN WEIJIE TECH
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