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Method for resolving barnidipine mother nucleus by using glucosamine as resolving agent

A technology of barnidipine mother and glucosamine, which is applied in the field of separation of barnidipine mother nucleus, can solve the problems of high price of the resolving agent, rising cost, high cost, etc., and achieves easy control, mild reaction conditions, solvent low toxicity

Inactive Publication Date: 2014-02-19
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the resolving agent used in this method is relatively expensive, and most of the solvents used in the resolution are N,N-dimethylformamide (belonging to the second class of solvents), which is slightly higher than the cost of conventional solvents, and the solvent residue in the later stage The processing link will lead to an increase in cost. If it is used to enlarge production, even if the method of recycling the splitting agent is used, the cost is quite expensive

Method used

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  • Method for resolving barnidipine mother nucleus by using glucosamine as resolving agent
  • Method for resolving barnidipine mother nucleus by using glucosamine as resolving agent
  • Method for resolving barnidipine mother nucleus by using glucosamine as resolving agent

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1 Using glucosamine as a resolving agent to resolve the barnidipine core

[0027] Add glucosamine (37.6g, 0.21mol) to the 1L ethanol solution of the parent nucleus racemate of barnidipine (70g, 0.21mol) and reflux at 90°C until completely dissolved, continue stirring for 3 hours and then add 0.4L of water After stirring for half an hour, slowly lower the temperature to normal temperature, cool and crystallize for 2 hours, then filter with suction, and finally wash with new cold ethanol to remove the solution on the crystal surface to obtain the glucosamine salt of the dipine nucleus. Transfer the salt to a 5L round bottom flask, add 1L of a mixed solvent of ethanol and water (volume ratio 5:2), slowly rise to 90°C and maintain for 30 minutes, and finally drop to 0°C within 1 hour, The crystals were grown at 0°C for 3 hours, and finally collected by filtration and washed with new cold ethanol to remove the solution on the surface of the crystals. After drying, t...

Embodiment 2

[0029] Example 2 Using glucosamine as a resolving agent to resolve the barnidipine core

[0030] Add glucosamine (188.0g, 1.05mol) to the 5L ethanol solution of the parent nucleus racemate of barnidipine (350g, 1.05mol) and reflux at 90°C until completely dissolved, continue stirring for 4 hours and then add 2.0L of water After stirring for half an hour, slowly lower the temperature, cool and crystallize for 3 hours, then suction filter, and finally wash with new cold ethanol to remove the solution on the crystal surface to obtain the glucosamine salt of the dipine nucleus. Move the salt into a 30L reaction kettle, add 5L of mixed solvent of ethanol and water (volume ratio 5:2), slowly rise to 90°C and maintain for 30 minutes, and finally drop to 0°C within 1.5 hours, and The crystals were grown at 0°C for 3.5 hours, and finally collected by filtration and washed with fresh cold ethanol to remove the solution on the surface of the crystals. After drying, the glucosamine salt ...

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Abstract

The invention discloses a method for resolving a barnidipine mother nucleus by using glucosamine as a resolving agent. The method comprises the following process routes shown in the description: resolving the barnidipine mother nucleus by using the glucosamine as the resolving agent, wherein the easily available low-cost barnidipine is used as a chiral resolving agent for resolving the racemized barnidipine mother nucleus and solvents used in the middle are easily available and low-cost alcohol and water; and obtaining a single isomer of the barnidipine mother nucleus with high yield and high optical purity (ee value is 99.0-99.6%) with. The method has the beneficial effects that the resolving agent is low-cost and easily available, the using of expensive resolving agents is avoided, the used solvents are harmfulless, the resolution recovery rate is high, and the product has high optical purity and strong atom economy; the experiment operation is simple, reaction conditions are mild and easy to control, and the technology repeatability is high; and the implementation of the industrial production is easy.

Description

technical field [0001] The invention relates to a method for splitting barnidipine core by using glucosamine as a splitting agent. Background technique [0002] Barnidipine is a dihydropyridine calcium antagonist, which can relax blood vessels, increase coronary flow, and lower blood pressure. The effect is strong and long-lasting, and can last for 24 hours. It is well absorbed after oral administration, and the peak plasma concentration is reached after 1 to 6 hours. t 1 / 2 About 10 hours. This product is a potent, long-acting dihydropyridine calcium antagonist antihypertensive drug. It has a strong ability to inhibit calcium ion influx, reduce calcium ion in cells, relax and expand blood vessels, reduce peripheral vascular resistance and play a significant antihypertensive effect, and its action strength is 5 times that of nicardipine. [0003] At present, for the synthesis of the drug molecule, a major difficulty comes from the construction of the chiral center of the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/90
CPCC07D211/90
Inventor 周广连魏茂杰马毅
Owner QILU UNIV OF TECH
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