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Method for preparing pinaverium bromide and application thereof

A kind of pinaverium bromide, reaction technology, applied in the field of preparation technology of pinaverium bromide, can solve the problem of low content of pinaverium bromide cis isomer etc.

Active Publication Date: 2012-11-14
SHANGHAI CHENPON PHARM TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But the cis-isomer content of the obtained intermediate is 95%, and the trans-isomer content is 5%, the cis-isomer content of the pinaverium bromide (formula I) synthesized by this intermediate is not high, and exists above defects

Method used

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  • Method for preparing pinaverium bromide and application thereof
  • Method for preparing pinaverium bromide and application thereof
  • Method for preparing pinaverium bromide and application thereof

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preparation example Construction

[0056] The preparation method of the intermediate compound shown in formula II provided by the present invention comprises steps:

[0057] (a) Nopol alcohol, palladium carbon and methanol with chemical structure such as formula IV are mixed and reacted to obtain a compound with chemical structure such as formula V;

[0058]

[0059] (b) mixing the compound of formula V obtained in step (a), toluene and sodium hydroxide, and heating for reaction;

[0060] (c) Add the mixed solution of the compound of chemical structure such as formula VI and toluene, reflux, cool to room temperature;

[0061] (d) adding water for extraction, taking the organic layer, and distilling under reduced pressure to obtain the compound intermediate of formula II.

[0062] A preferred solution is:

[0063] (a) Nopol alcohol, palladium carbon and methanol with chemical structure such as formula IV were mixed and reacted for 2-8 hours, filtered, and methanol was removed to obtain a compound with chemica...

Embodiment 1

[0098] Preparation of 2-[2-(2-morpholinyl-2-ethoxyl-ethyl)]-6,6-dimethylnoprene (formula II)

[0099] 1. At room temperature, put into the autoclave 600L of methanol, 100Kg of Nopol alcohol (formula IV), 10Kg of palladium carbon, react under 6-7 kg of hydrogen pressure for 4-6 hours, filter the catalyst, wash with methanol, and evaporate under reduced pressure Methanol to obtain 90Kg of the compound of formula V, with a yield of 88.7%;

[0100] 2. Then add 300L of toluene and 50Kg of the compound of formula V into the 1000L reactor, put in 13kg of sodium hydroxide at room temperature, raise the temperature to reflux, and react for 2 hours;

[0101] 3. Then add the mixed solution of 45kg 2-chloroethylmorpholine (formula VI) and 100L toluene, reflux reaction for 1 hour after adding, cool, add 300L water for extraction, and separate the organic layer;

[0102] 4. The aqueous layer was extracted twice with toluene, 200 L each time, the organic layers were combined, washed with 20...

Embodiment 2

[0106] Preparation of 2-[2-(2-morpholinyl-2-ethoxyl-ethyl)]-6,6-dimethylnoprene (formula II)

[0107] 1. Under room temperature, drop into methanol 600L in the autoclave, Nopol alcohol 100Kg (formula IV), palladium carbon 10Kg, react 2 hours under 9-10 kilograms of hydrogen pressure, filter catalyst, wash with methanol, decompress and evaporate methyl alcohol, 91.3Kg of the compound of formula V was obtained, with a yield of 90.4%;

[0108] 2. Then add 300L of toluene and 50Kg of the compound of formula V into the 1000L reactor, put in 13kg of sodium hydroxide at room temperature, raise the temperature to reflux, and react for 2 hours;

[0109] 3. Then add the mixed solution of 45kg 2-chloroethylmorpholine (formula VI) and 100L toluene, reflux reaction for 1 hour after adding, cool, add 300L water for extraction, and separate the organic layer;

[0110] 4. The aqueous layer was extracted twice with toluene, 200 L each time, the organic layers were combined, washed with 200 L ...

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Abstract

The invention provides a method for preparing pinaverium bromide and an intermediate thereof, which relate to the pharmaceutical process. The cis isomer content of the intermediate 2-[2-(2-morpholino-2-ethoxy-ethyl)]-6, 6-dimethyl nopyl alkyl is high and the cis-isomer content of the obtained pinaverium bromide is more than or equal to 99 percent. The intermediate 2-[2-(2-morpholino-2-ethoxy-ethyl)]-6, 6-dimethyl nopyl alkyl is prepared by collecting cut fraction of 133-134 DEG C under 270 Pa.

Description

technical field [0001] The invention relates to a pharmaceutical technology, in particular to a preparation technology of pinaverium bromide. Background technique [0002] Pinaverium bromide is a calcium antagonist clinically used to treat pain related to intestinal dysfunction, abnormal defecation and gastrointestinal discomfort, and pain related to biliary dysfunction. The synthetic routes reported abroad are 2-[2-(2-morpholinyl-2-ethoxyl-ethyl)]-6,6-dimethylnoprene (formula II) and 2-bromo-4, The reaction of 5-dimethoxybenzyl bromide (formula III) gives pinaverium bromide (formula I). [0003] [0004] Pinaverium bromide is optically active, and it is its cis-isomer that has clinical therapeutic effects. In the obtained pinaverium bromide of prior art, often require the content of its trans-isomer to be no more than 9%, lower then be difficult to reach, the result makes the pinaverium bromide cis-isomer content partial low, affecting the therapeutic effect. [0005...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/088C07D295/096A61K31/5375A61P1/06A61P1/16
Inventor 杜狄峥吴瑜亮胡克斌吴波峰卢鑫
Owner SHANGHAI CHENPON PHARM TECH CO LTD
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