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Novel preparation method for nicergoline

A technology of nicergoline and a new method, applied in the field of preparation of nicergoline, can solve problems such as improvement, cumbersome operation steps, cumbersome operation, etc.

Inactive Publication Date: 2013-06-19
SHANDONG FANGMING PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This preparation method is cumbersome to deal with the functional groups on the reaction, especially when removing the chloro group, the reaction conditions are harsh, and adding too many reaction steps is not conducive to the improvement of the yield.
[0007] In the two preparation methods, either methylation first, or photocatalysis first, and finally carboxylate formation, the yield of this synthesis sequence is low, and some groups are modified at the same time, and the increased positioning group is used in subsequent reactions. need to be removed, making the operation steps cumbersome

Method used

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  • Novel preparation method for nicergoline

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Experimental program
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Effect test

Embodiment Construction

[0013] 1. Preparation of Ergool-5-bromo-3-pyridinecarboxylate (Intermediate 1)

[0014] Add 380 ml of dichloromethane, 50 grams of ergot alcohol and 25 grams of triethylamine into the reaction bottle, slowly add 60 grams of 5-bromonicotinoyl chloride after stirring, and control the temperature at about 30°C. The end point of the reaction was detected by thin-layer method, and the developing solvent was ethyl acetate:heptane=1:1. After the reaction was complete, water was added, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The organic layer was diluted with ammonia, washed with water, and anhydrous Na 2 SO 4 Dry and concentrate to dryness under reduced pressure to obtain crude Nicergoline. Acetone was added to the crude product, stirred and heated until completely dissolved, cooled to room temperature, crystallized by freezing, filtered, and dried under reduced pressure to obtain 102 g of the product. The yield is about 85%.

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Abstract

The invention discloses a novel synthesis method for the raw material medicine of nicergoline (shown in formula I). The novel synthesis method disclosed by the invention comprises the following steps of: reacting ergosterol with 5-bromonicotinate derivatives to generate carboxylic ester; then performing a photocatalytic reaction with methanol in an acidic condition; and then performing a methylation reaction with a methylation reagent to generate nicergoline. With the adoption of the novel synthesis method disclosed by the invention, the cumbersome operation of the methods disclosed by the existing patents is avoided, the used solvent is low in toxicity, and the yield is high. The novel synthesis method is beneficial to industrialized popularization and application.

Description

technical field [0001] The invention relates to a new method for preparing nicergoline, which belongs to the technical field of chemical medicine synthesis. Background technique [0002] Nicergoline has a good therapeutic effect on vascular dementia by expanding cerebral blood vessels and improving brain metabolism, especially for Alzheimer's disease (Alzheimer's disease, ie AD disease). With the intensification of urbanization and aging, the number of elderly people in China has exceeded 140 million, and the incidence of geriatric diseases is also increasing year by year. With the increase of residents' income, the requirements for the quality of life of the elderly have also increased. Under this trend, the demand for therapeutic drugs for mental diseases such as senile dementia has also increased significantly. [0003] Nicergoline is a semi-synthetic ergot alkaloid derivative developed by Italy Aibao Pharmaceutical Factory. In its synthetic process patent declared in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D457/02
Inventor 刘存领范兴山王飞龙沈红宾解利民
Owner SHANDONG FANGMING PHARMACEUTICAL CO LTD
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