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A method for recovering hydrocortisone from hydrocortisone butyrate mother liquor

A technology for hydrocortisone butyrate and hydrocortisone, which is applied in the directions of organic chemistry, steroids, etc., can solve the difficulty of recovering hydrocortisone butyrate, the inability to recover hydrocortisone, and the inability to obtain quality products, etc. problems, to achieve the effect of simple and feasible process operation, high production safety and material stability, and low production cost

Active Publication Date: 2017-02-08
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (3) It is extremely difficult to recover hydrocortisone butyrate by recrystallization from the mother liquor, and it is impossible to obtain a product that meets the quality requirements after repeated recrystallization
Carry out hydrolysis reaction in the traditional way, 11 esters, 17 esters and 21 esters in the mother liquor, especially 17 esters wherein can rapidly take place the destructive reaction of steroidal structure D ring breakage, thus can't reclaim hydrocortisone at all; If Discharging the mother liquor into the environment after simple treatment will not only cause waste of resources and pollution of the environment, but also cause great harm to the ecological environment due to the hormones contained in the mother liquor
At present, there are no public reports at home and abroad on the recovery and treatment process for hydrocortisone butyrate mother liquor

Method used

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  • A method for recovering hydrocortisone from hydrocortisone butyrate mother liquor
  • A method for recovering hydrocortisone from hydrocortisone butyrate mother liquor

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Take 100ml of hydrocortisone butyrate mother liquor, add methanol and continue to concentrate under reduced pressure until viscous. Then add 300ml of methanol and 300ml of dichloromethane and stir to dissolve, lower the temperature to below 0°C, pass through argon protection, control the temperature -5°C to 0°C, add dropwise a solution of 4g potassium hydroxide dissolved in 100ml of methanol, at -5°C ~0°C heat preservation reaction for 1.5 hours. Control the temperature from -5°C to 0°C and add dropwise methanol solution of glacial acetic acid to neutralize to pH6~7. Concentrate under reduced pressure until viscous, add isopropyl ether, freeze, filter, and dry to obtain 60.3 g of hydrocortisone, with an HPLC purity of 97.3%.

Embodiment 2

[0030] Take 100ml of hydrocortisone butyrate mother liquor, add methanol and continue to concentrate under reduced pressure until viscous. Then add 250ml of methanol and 320ml of dichloromethane and stir to dissolve, lower the temperature to below -5°C, pass through nitrogen protection, control the temperature -10°C to -5°C, add dropwise a solution of 4g of sodium hydroxide dissolved in 200ml of methanol, at -10 ℃ ~ -5 ℃ heat preservation reaction for 2 hours. Control the temperature at -10°C to -5°C and add dropwise methanol solution of glacial acetic acid to neutralize to pH6~7. Concentrate under reduced pressure until viscous, add petroleum ether, freeze, filter, and dry to obtain 59.8 g of hydrocortisone, with an HPLC purity of 97.1%.

Embodiment 3

[0032] Take 100ml of hydrocortisone butyrate mother liquor, add methanol and continue to concentrate under reduced pressure until viscous. Then add 200ml of methanol and 360ml of dichloromethane and stir to dissolve, cool down to below 5°C, pass through nitrogen protection, control the temperature at 0°C to 5°C, add dropwise a solution of 4g of sodium hydroxide dissolved in 200ml of methanol, at 0°C to 5°C Incubate the reaction for 75 minutes. Control the temperature at 0°C-5°C and add dropwise methanol solution of glacial acetic acid to neutralize to pH6-7. Concentrate under reduced pressure until viscous, add petroleum ether, freeze, filter, and dry to obtain 58.6 g of hydrocortisone, with an HPLC purity of 97.0%.

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Abstract

The invention discloses a method for recycling hydrocortisone in hydrocortisone butyrate mother liquor. The method comprises the steps of adding refined hydrocortisone butyrate mother liquor into methyl alcohol to obtain a mixture, concentrating the mixture until the mixture is sticky, adding a mixed solvent for stirring and dissolving, and performing cooling; under the protection of inert gas, dropping alkaline liquid, performing heat preservation reaction after the alkaline liquid is added; performing neutralization, concentration, freezing filtration and drying to obtain hydrocortisone. By a reaction mode combining inert gas protection and the mixed solvent, the phenomenon that materials cannot be recycled because of decomposition of compounds due to breakage of the D-ring structure of steroid nucleus is effectively avoided. The method disclosed by the invention is easy to operate, short in treatment time, low in production cost and high in production safety and material stability, and the environment cannot be polluted; the recycling rate is high, so that the purity of recycled hydrocortisone is high; after being dried, hydrocortisone can be directly used as a raw material for producing hydrocortisone butyrate.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a method for recovering hydrocortisone from hydrocortisone butyrate mother liquor. Background technique [0002] The structural formula of hydrocortisone butyrate (11β, 17α, 21-trihydroxy-pregna-4ene-3,20-dione-17α-butyrate) is: [0003] [0004] Hydrocortisone butyrate belongs to the adrenal cortex hormone drug, which has various pharmacological effects such as anti-inflammation, anti-allergy and immune suppression, and is suitable for treating eczema, dermatitis, allergic skin diseases, etc. [0005] The existing preparation method of hydrocortisone butyrate is to generate 17α and 21-cyclic esters from hydrocortisone and corresponding orthobutyrate, and then hydrolyze under acidic conditions to restore the original hydroxyl group at the 21 position, thereby obtaining the product . The hydrolyzate obtained in the hydrolysis ring-opening reaction step not only co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J5/00
CPCC07J5/0053
Inventor 刘玉亭廖俊付林曾建华李桂莲冯旋
Owner HUAZHONG PHARMA
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