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Cis-atracurium besilate for injection

A technology for injection of cis-atracurium besylate, applied in muscular system diseases, neuromuscular system diseases, organic chemistry, etc.

Inactive Publication Date: 2013-01-30
SUZHOU ERYE PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method does not use a column chromatography step, this method requires multiple recrystallizations and is costly, the yield is low, and industrialization is difficult

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of R-tetrahydropapaverine salt

[0035] The reaction formula of this step is:

[0036] .

[0037] Dissolve 17.5kg of tetrahydropapaverine hydrochloride in 200kg of water, and filter to remove impurities. Neutralize with 6mol / L NaOH solution and adjust the pH to about 10. The resulting mixture was extracted three times with 200 kg toluene, extracted, the toluene extracts were combined, and dried with anhydrous sodium sulfate. The dried toluene was filtered and concentrated to obtain 15kg of oil.

[0038] Add 250kg of methanol to dissolve the obtained oil, add 7.56kg of resolving agent N-acetyl-L-leucine, reflux for 30 minutes, cool to room temperature, add 50kg of ether, mix well, and place to crystallize.

[0039] The crystallization liquid was filtered, and the filtrate was concentrated to dryness and weighed to obtain a white solid. The resulting solid was recrystallized three times from 50 times acetone. Filter and dry the filter...

Embodiment 2

[0040] Example 2: Condensation of tetrahydropapaverine with a bridge

[0041] The reaction formula of this step is:

[0042] .

[0043] Dissolve 4.2 kg of N-acetyl-L-leucine salt of R-tetrahydropapaverine in 30 kg of water, adjust the pH to 10 with NaOH solution, add 20 kg of toluene to the obtained white turbid liquid, extract 3 times, combine the toluene layers, The toluene was evaporated under reduced pressure to obtain a yellow oil, 2.6 kg of free R-type tetrahydropapaverine.

[0044] Put the free R-tetrahydropapaverine into the reaction flask, add 720g of pentamethylene glycol acrylate, 200ml of glacial acetic acid, stir and heat up to 70°C, react for 4h, add toluene 2.5L after the reaction is complete, and stir for 30min. The reaction solution was concentrated, and the concentrate was passed through a silica gel column. The eluent: chloroform-methanol (20:1), detected by TLC, collected the eluate at the first point, and concentrated to obtain 2.73 kg of light yell...

Embodiment 3

[0045] Embodiment 3: preparation quaternary ammonium salt

[0046] This step reaction formula is as follows:

[0047] .

[0048] Collect 2.73 kg of the resulting eluate concentrate into the condensation reaction column chromatography, add 4.8 L of methyl benzenesulfonate,

[0049] Stir overnight at room temperature. Add 10 kg each of toluene and water to the reaction solution, stir for 10 minutes, and transfer the reaction solution to the separatory

[0050] In the funnel, separate the water layer, wash the toluene layer with water for 2 times, combine the water layers, and wash the water layer twice with 5kg of toluene.

[0051] The aqueous layer was extracted three times with 5 kg of dichloromethane, and most of the solvent was evaporated at 30°C. Add dropwise to anhydrous ether with stirring

[0052] In 10L, a solid was precipitated, filtered, washed with anhydrous ether, and dried in vacuo to obtain 3.6kg of white solid (94.5%,

[0053] 2.9 mol).

[0054] The resu...

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PUM

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Abstract

The invention relates to the field of pharmaceutical chemistry, and practically provides cis-atracurium besilate for injection and a preparation method thereof. The method disclosed by the invention is stable and reliable and small in pollution to environment and the product impurity content is low.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular, the invention relates to cis-atracurium for injection and a preparation method thereof. Background technique [0002] Atracurium cis-benzenesulfonate is a new type of benzylisoquinoline intermediate-effect non-depolarizing muscle relaxant, and it is one of the 10 isomers of atracurium, which has muscle activity similar to that of atracurium. Pine effect, metabolic process and advantages of vecuronium bromide. Cisatracurium besylate is a single isomer of atracurium besylate, which has similar muscle relaxant effect and metabolic mode as atracurium besylate, but its muscle relaxant strength is about It is 3 times that of the drug, does not release histamine, and has a small cardiovascular response. It is an ideal non-depolarizing muscle relaxant with a medium-term effect. [0003] The chemical name of Cisatracurium Besilate is: (1R, 1'R, 2R, 2'R)-2,2'-[1,5-pentanediylbis[oxy(3- ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/20A61K31/4725A61K9/00A61P21/02
Inventor 陆文娟隋巍峰李励谢丽华
Owner SUZHOU ERYE PHARMA CO LTD
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