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Synthetic method of desonide

A synthetic method, the technology of desonide, applied in the direction of steroids, organic chemistry, etc., can solve the problems of high energy consumption, large pollution, long route, etc., and achieve the effect of low energy consumption and mild process

Active Publication Date: 2014-07-23
ZHEJIANG XIANJU JUNYE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent application number 201010221376.7 discloses a synthetic method of desonide, using 16-hydroxyprednisolone as the starting material, desonide reacted with acetone under acid catalysis, and 16-hydroxyprednisolone is synthesized It is relatively complicated. It is the final product of reactions such as bromination, debromination, dehydration, esterification, epoxy, bromination, debromination, elimination, oxidation, and hydrolysis using mold dehydrogenation products as raw materials. The yield of the product is low and the route is relatively complicated. Long and polluted, so choosing 16 hydroxyprednisolone is not a good intermediate
And the yield is only 30%
The synthesis steps of desonide disclosed in this patent document are as long as 10 steps, and highly polluted hydrobromic acid and metal chromium are used in the reaction process, which causes great pollution to the environment. Since the yield is 30%, it can The cost is high, and the corresponding energy consumption is high; in terms of technical feasibility, the two bromination and debromination reactions of this synthetic route are difficult to control, and deviations in operation can lead to large deviations in quality, resulting in a large increase in cost

Method used

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  • Synthetic method of desonide

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Effect test

Embodiment 1

[0025] A kind of synthetic method of desonide provided by the present embodiment comprises the following steps:

[0026] 1) Add 50kg of pyridine and 10kg of prednisone acetate as raw materials into the reaction vessel for stirring and cool down to 15°C; add 15kg of N-chlorosuccinimide into the cooled reaction vessel, and introduce 5kg of sulfur dioxide to stir and keep it warm for 1h 35wt% hydrochloric acid of 0 ℃ is added in the reaction vessel after heat preservation, after stirring for 1h, stand still for 4h; The solution in the reaction vessel after standing is subjected to spin filtration, and the filter cake obtained after spin filtration is washed to no pyridine Carry out drying at 65 ℃ after taste, obtain compound II, the content is 96%, the yield is 83.5%, and the waste water is sent to the pyridine recovery place;

[0027] 2) Add 5kg of compound II and 100kg of acetone synthesized in step 1) to the reaction vessel and cool to 3°C; add 0.6kg of formic acid to the cool...

Embodiment 2

[0033] A kind of synthetic method of desonide provided by the present embodiment comprises the following steps:

[0034] 1) Add 40kg of dimethylformamide and 5kg of prednisone acetate as raw materials into the reaction vessel to stir and cool down to 20°C; add 8kg of N-chlorosuccinimide to the cooled reaction vessel, and introduce 1kg of sulfur dioxide Stir and keep warm for 0.5h; add 35wt% hydrochloric acid at 5°C to the reaction vessel after heat preservation, stir for 0.5h and then let it stand for 3h; filter the solution in the reaction vessel after standing, and filter the obtained The filter cake was washed with water until there was no pyridine smell, and then dried at 60°C to obtain Compound II with a content of 96.5% and a yield of 83%, and the waste water was sent to the pyridine recovery place;

[0035]2) Add 3kg of compound II and 80kg of acetone synthesized in step 1) into the reaction vessel and cool down to 1°C; add 0.6kg of benzoic acid into the cooled reaction...

Embodiment 3

[0041] A kind of synthetic method of desonide provided by the present embodiment comprises the following steps:

[0042] 1) Add raw materials 60kg of pyridine and 15kg of prednisone acetate into the reaction vessel to stir and cool down to 20°C; add 30kg of N-chlorosuccinimide to the cooled reaction vessel, and feed 12kg of sulfur dioxide into it to keep stirring for 2 hours Add 35wt% hydrochloric acid at 3°C ​​to the reaction vessel after heat preservation, stir for 2 hours and let it stand for 5 hours; filter the solution in the reaction vessel after standing, and wash the filter cake obtained after the reaction to no pyridine Dry at 70° C. to obtain compound II, the content is 96.2%, and the yield is 83.4%, and the waste water is sent to the pyridine recovery place;

[0043] 2) Add 8kg of compound II and 120kg of acetone synthesized in step 1) into the reaction vessel and cool to 5°C; add 2.56kg of chloroformic acid into the cooled reaction vessel and stir, and add 9wt% pot...

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Abstract

The invention discloses a synthetic method of desonide. The synthetic method is characterized by carrying out elimination reaction on prednisone acetate by using sulfur dioxide in the presence of a first catalyst and an inert gas, then carrying out oxidation reaction on a product after elimination by using an oxidant in the presence of a second catalyst, then carrying out condensation treatment on a product after oxidation by using acetone in the presence of a third catalyst, carrying out selective reduction on a product after condensation in the presence of a fourth catalyst and finally carrying out hydrolysis reaction on a product after reduction in the presence of a fifth catalyst, thus preparing desonide. The synthetic method has the beneficial effects that desonide can be obtained by using prednisone acetate as the raw material and carrying out elimination, oxidation, condensation, reduction and hydrolysis; all the solvents in the synthetic process are recycled and reused, heavy metals do not participate in reaction in the reaction process, the technical process is mild and the energy consumption is low, so that the synthetic method is environment-friendly and clean.

Description

technical field [0001] The invention relates to the field of medicine synthesis, in particular to a synthesis method of desonide. Background technique [0002] Desonide is a synthetic non-halogenated intermediate corticosteroid hormone with anti-inflammatory, anti-pruritic and vasoconstrictive properties. It is clinically used in hyperproliferative or inflammatory skin diseases such as psoriasis and eczema. [0003] Chinese patent application number 201010221376.7 discloses a synthetic method of desonide, using 16-hydroxyprednisolone as the starting material, desonide reacted with acetone under acid catalysis, and 16-hydroxyprednisolone is synthesized It is relatively complicated. It is the final product of reactions such as bromination, debromination, dehydration, esterification, epoxy, bromination, debromination, elimination, oxidation, and hydrolysis using mold dehydrogenation products as raw materials. The yield of the product is low and the route is relatively complicat...

Claims

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Application Information

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IPC IPC(8): C07J71/00
Inventor 赵万红
Owner ZHEJIANG XIANJU JUNYE PHARM CO LTD
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