Preparation method of prednisolone acetate

A technology of prednisolone acetate and sodium hypochlorite, which is applied in the fields of steroids and organic chemistry, can solve the problems of difficult separation in the post-treatment process, low concentration of substrate feeding, complicated production process, etc., and achieve good application prospects and unique system Odor reduction and high yield effect

Inactive Publication Date: 2021-02-19
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the biotransformation is to use hydrocortisone acetate as the transformation substrate, and Arthrobacter ferment to prepare prednisolone acetate. This preparation method has the disadvantages of high substrate cost, low substrate feeding concentration, long production cycle and difficult separation in the post-treatment process. and low purity
Chemical synthesis of 17α-hydroxy-1,4,9-triene-pregna-3,20-dione as raw material, through bromin...

Method used

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  • Preparation method of prednisolone acetate
  • Preparation method of prednisolone acetate
  • Preparation method of prednisolone acetate

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preparation example Construction

[0034] One embodiment of the present invention provides a synthesis method of prednisolone acetate, comprising the following steps S10-S20.

[0035] Step S10: carry out bromination reaction on the compound of formula (I) to obtain the compound of formula (II); wherein, the structures of the compound of formula (I) and the compound of formula (II) are as follows:

[0036]

[0037] Step S20: subjecting the compound of formula (II) to a debromination reaction, and after post-treatment to obtain the compound of formula (III) prednisolone acetate; wherein, the post-treatment includes adding a sodium salt selected from sodium thiosulfate, sodium sulfite and sodium hypochlorite At least one, the structure of the compound of formula (III) is as follows:

[0038]

[0039] Sodium salt is added in the post-treatment to destroy solvents such as thioglycolic acid to achieve better impurity removal effect, and the special odor of the system is greatly reduced, not pungent, the process...

Embodiment 1

[0142] 1) Preparation of formula (IV) compound

[0143] 1.1 Incline cultivation

[0144] Nocardia was used as the strain, the medium composition and mass fraction were 1.3% glucose, 1.3% yeast extract and 2% agar, pH=7.0, cultured at 30°C for 3 days, and stored at 3-5°C for later use.

[0145] 1.2 Primary seed culture

[0146] The medium components are 0.3% beef extract and 0.5% peptone, pH=6.8, half of the slant medium is put into 100 ml primary seed medium, the shaker speed is controlled at 180rpm, and cultured at 30°C for 24h.

[0147] 1.3 Secondary seed culture

[0148] The composition of the culture medium is 1% glucose, 1% corn steep liquor, 1% peptone and 0.01% potassium dihydrogen phosphate, pH=7.0, the shaker speed is controlled at 180 rpm, and cultured at 30° C. for 16 hours.

[0149] 1.4 Feeding

[0150] Grind anecorta acetate (compound of formula V) to 200 mesh, weigh 120g, add water 360mL, Tween 80 3g, methanol 60mL, mix well and then feed into the secondary s...

Embodiment 2

[0176] Embodiment 2 is substantially the same as embodiment 1, and difference is that sodium thiosulfate is changed into sodium hypochlorite in the step 4) of embodiment 2, and other steps are identical with embodiment 1 with process parameter.

[0177] After calculation, the total yield of prednisolone acetate obtained in step 3) and step 4) is 91%, and the purity is 99.3%.

[0178] Prednisolone acetate yield=the molar weight of prednisolone acetate / the molar weight of formula (I) compound×100%

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Abstract

The invention relates to prednisolone acetate and a preparation method of prednisolone acetate, which are characterized in that the prednisolone acetate is prepared by sequentially carrying out a biological fermentation, an esterification reaction, a bromination reaction and a debromination reaction on the raw material, the prednisolone acetate is subjected to a hydrolysis reaction to obtain prednisolone, the overall yield is up to 81.75%, and the HPLC area normalization content of prednisolone is up to 99.5%. The preparation method is short in synthetic route and low in cost, is suitable forindustrial production, and has a very high industrial value.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of prednisolone acetate. Background technique [0002] The chemical name of prednisolone acetate is 11β, 17α, 21-trihydroxypregna-1,4-diene-3,20-dione-21-acetate, which is a glucocorticoid drug used externally to treat Allergic, non-infectious skin diseases and some proliferative skin diseases, such as dermatitis, eczema, neurodermatitis, seborrheic dermatitis and pruritus, etc. Prednisolone acetate can also be used in allergic, autoimmune inflammatory diseases and collagen diseases such as rheumatism, rheumatoid arthritis, lupus erythematosus, severe bronchial asthma, nephrotic syndrome, thrombocytopenic purpura, neutropenia syndrome, acute lymphoblastic leukemia, various adrenal insufficiency, exfoliative dermatitis, non-herpetic neurodermatitis and eczema. [0003] The preparation method of traditional prednisolone acetate is divided into biotrans...

Claims

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Application Information

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IPC IPC(8): C07J5/00
CPCC07J5/0053
Inventor 吴亚克曾春玲靳志忠文智彬刘喜荣
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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