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Preparation method of pinaverium bromide

A technology of pinaverium bromide and bromoethoxyethyl, which is applied in the field of preparation of drugs for the treatment of irritable bowel syndrome, can solve the problems of harsh reaction conditions, prone to side reactions, difficult to remove impurities, etc., and achieve mild reaction conditions , It is beneficial to industrial production and the effect of improving the yield

Active Publication Date: 2010-06-30
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The purpose of this invention is to provide a kind of new preparation method of pinaverium bromide, this method selects the new process synthesis route, starts with the starting raw material that is cheaper and easy to get to react, and catalytic hydrogenation is placed in the last step reaction, has overcome conventional The reaction conditions of the method are harsh, side reactions are prone to occur, and impurities are difficult to remove. The application of this process route can reduce the cost of raw materials, the reaction conditions are mild, and the product purity and yield are greatly improved.

Method used

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Examples

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Embodiment 1

[0042] Example 1 Preparation of 2-(2-bromoethanol)-6,6-dimethylbicyclo[3.1.1]-2-heptene

[0043] In the reaction flask equipped with a thermometer, add 200ml of dry toluene, add 40g (0.24mol) Nopol alcohol, stir, add dropwise 25ml (0.24mol) of phosphorus tribromide, continue stirring for 10 minutes after the dropwise addition, and slowly heat up to 80°C, reacted for 2 hours, added 50ml of water, separated the liquid, took the organic phase, dried over anhydrous magnesium sulfate, filtered, dew liquid was distilled under reduced pressure to obtain 49.5g of oil, with a yield of 90%.

Embodiment 2

[0044] Example 2 Preparation of 2-bromoethoxyethyl-6,6-dimethylbicyclo[3.1.1]-2-heptene

[0045] In a 500mL four-neck bottle equipped with a thermometer, add 200mL of bromoethanol, stir and heat up to 60°C, add 7.5g (0.33mol) of sodium metal in batches, after the reaction of sodium metal is complete, add 23g (0.1mol) Intermediate 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]-2-heptene, after the dropwise addition, continue to stir and react at 80°C-90°C for 12 hours, then stop the reaction , cooling, adjust the pH value to about 7 with 10% sodium bicarbonate solution, pour into 500mL of ice water, add 200mL of chloroform, separate the liquids, take the organic phase, dry over anhydrous magnesium sulfate, and distill under reduced pressure to obtain 25.6g of oily matter, Yield 88.6%.

Embodiment 3

[0046] Example 3 Preparation of 2-bromo-4,5-dimethoxy-benzyl bromide

[0047] In a 500ml four-necked flask, add 200ml of acetic acid, add 17g (0.1mol) of 3,4-dimethoxybenzyl alcohol, stir, add 32g (0.2mol) of bromine dropwise, the hydrogen bromide produced by the reaction is mixed with lye Absorbed, continued to stir for 6 hours after the dropwise addition, evaporated the acetic acid under reduced pressure, and recrystallized the obtained solid with petroleum ether to obtain 26.5 g of the solid, the yield was 85.2%, and mp: 86.1-86.5°C.

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Abstract

The invention relates to a preparation method of curative to intestinal irritable syndrome, in particular to a preparation method of a high selectivity calcium ion antagonist, namely, pinaverium bromide. The preparation method includes that nopol is halogenated, condensed with bromoethanol alkali metal compound, condensed with reaction product of morpholine, 2 - bromine - 4 and 5 - dimethoxy bromobenzyl, catalyzed and hydrogenated into pinaverium bromide. By the invention, reaction conditions are more temperate, operation becomes easier, yield is much improved and the product is more suitable for industrial production. The purity of the product reaches 99.8 percent (detected by HPLC) and the biggest impurity is less than 0.18 percent, in accordance with the demand of the fifth-edited <European Pharmacopoeia Standard>.

Description

technical field [0001] The invention relates to the preparation of a medicine for treating irritable bowel syndrome, in particular to a preparation method of pinaverium bromide, a highly selective calcium ion antagonist. Background technique [0002] Pinaverium bromide is a highly selective calcium ion antagonist with a chemical name of 4-[(2-bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2(6, 6-Dimethylbicyclo[3,1,1]hept-2-yl)ethoxy]ethyl]morpholine bromide, the structural formula is: [0003] [0004] Pinaverium bromide was first listed in 1975 and has been sold in more than 50 countries. It is a calcium antagonist with highly selective antispasmodic effect on the gastrointestinal tract. The mechanism of action on smooth muscle is the same as that of other calcium antagonists. However, it has a highly selective effect on colonic smooth muscle. Pinaverium bromide achieves antispasmodic effect by blocking the flow of calcium ions into intestinal wall smooth muscle cells, preve...

Claims

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Application Information

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IPC IPC(8): C07D295/096A61P1/06
Inventor 赵志全
Owner LUNAN PHARMA GROUP CORPORATION
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