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Preparation method of triamcinolone acetonide

A compound and reaction technology, applied in the field of drug synthesis, can solve the problems of long reaction steps, high preparation cost of triamcinolone acetonide, affecting process yield and quality, etc., achieve yield and quality improvement, shorten production cycle, save pressure and cost effect

Active Publication Date: 2022-05-13
HENAN LIHUA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above method has problems such as longer reaction steps due to the presence of acetate at the 21-position during the epoxy reaction at the 9 (11) position, which will cause partial hydrolysis, which seriously affects the yield and quality of the process, and the total yield is only 70%. , resulting in higher preparation cost of triamcinolone acetonide

Method used

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  • Preparation method of triamcinolone acetonide
  • Preparation method of triamcinolone acetonide
  • Preparation method of triamcinolone acetonide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation method of the triamcinolone acetonide of the present embodiment, reaction scheme is as follows:

[0040]

[0041] S1: Preparation of compound Ⅰ

[0042]Add 50g of tetraenyl acetate and 1500ml of acetone into the reaction flask, cool down to -5°C, add 10g of formic acid, stir for 5min, add potassium permanganate solution (add 25g of potassium permanganate to 400ml of water, stir to dissolve, dissolve Add 300ml of acetone, stir and cool down to -15°C to -20°C for later use), control the temperature at -5°C for 10 minutes, add sodium sulfite solution (add 10g of sodium sulfite to 100ml of water, stir to dissolve), heat up to 40°C, filter, and The filtrate was filtered into a concentration tank, concentrated until there was no acetone, diluted with 1000ml of water, cooled below 10°C, filtered out, and dried at 60°C for 10h to obtain 51g of compound I with a chromatographic purity of 97.9% and a yield of 102%.

[0043] S2: Preparation of compound Ⅱ

[00...

Embodiment 2

[0050] The preparation method of the triamcinolone acetonide of the present embodiment, the steps are as follows:

[0051] S1: Preparation of compound Ⅰ

[0052] Add 50g of tetraenyl acetate and 1500ml of acetone into the reaction flask, cool down to 0°C, add 7.5g of formic acid, stir for 5min, add potassium permanganate solution (add 20g of potassium permanganate to 400ml of water, stir to dissolve, dissolve Add 300ml of acetone, stir and cool down to -15°C to -20°C for later use), control the temperature at 0°C for 5 minutes, add sodium sulfite solution (add 5g of sodium sulfite to 100ml of water, stir to dissolve), heat up to 40°C, filter, and the filtrate Filter into a concentration tank, concentrate to no acetone, add 1000ml of water to dilute, cool down below 10°C, filter and discharge, and dry at 60°C for 10h to obtain 50.5g of compound Ⅰ, chromatographic purity: 98.0%, yield 101%.

[0053] S2: Preparation of compound Ⅱ

[0054] Add 50g of compound I and 800ml of tetr...

Embodiment 3

[0060] The preparation method of the triamcinolone acetonide of the present embodiment, the steps are as follows:

[0061] S1: Preparation of compound Ⅰ

[0062] Add 50g of tetraene acetate and 1500ml of acetone into the reaction flask, cool down to 0°C, add 5g of formic acid, stir for 5min, add potassium permanganate solution (add 30g of potassium permanganate to 400ml of water, stir to dissolve, and dissolve Add 300ml of acetone, stir and cool down to -15°C to -20°C for later use), control the temperature at 0°C for 15 minutes, add sodium sulfite solution (add 15g of sodium sulfite to 100ml of water, stir to dissolve), heat up to 40°C, filter, and filter the filtrate Put it into a concentration tank, concentrate until there is no acetone, add 1000ml of water to dilute, lower the temperature below 10°C, filter out the material, and dry at 60°C for 10h to obtain 50.5g of compound I with a chromatographic purity of 98.2% and a yield of 101%.

[0063] S2: Preparation of compoun...

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Abstract

The invention provides a preparation method of triamcinolone acetonide. The preparation method of triamcinolone acetonide comprises the following steps: S1, enabling tetraene acetate, formic acid and an oxidizing agent to react to obtain a compound I; s2, the compound I, perchloric acid and dibromohydantoin are subjected to a reaction, and a compound II is obtained; s3, the compound II and hydrofluoric acid are subjected to a fluorinated ketal reaction, and a triamcinolone acetonide crude product is obtained. According to the preparation method, the operation steps are simplified, the production cycle is greatly shortened, the discharge of a large amount of chemical wastewater is reduced, the pressure and the cost of treating the wastewater in a factory are saved, the pollution to the environment is reduced, the reaction is green and environment-friendly, the yield and the quality of the product are greatly improved, and the preparation method has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of triamcinolone acetonide. Background technique [0002] The English name of triamcinolone acetonide (triamcinolone acetonide) is Triamcinolone acetonide, and its chemical name is: 9-fluoro-11β,21-dihydroxy-16a,17-[(1-methylethylene)bis(oxygen)] - Pregna-1,4-diene-3,20-dione is a high-efficiency fluorine-containing adrenal cortex hormone drug, which is a common drug for skin diseases and is suitable for various skin diseases (such as neurodermatitis, eczema, psoriasis, etc.), arthralgia, bronchial asthma, periarthritis of the shoulder, tenosynovitis, acute sprain, chronic low back pain and ophthalmic inflammation, etc. Triamcinolone acetonide injection can be used for local injection of small lesions such as keloids, cystic acne, discoid lupus erythematosus, and alopecia areata; it can also be used for local injection in the joint cavity. At present...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
CPCC07J71/0031Y02P20/55
Inventor 陈文霞李合兴李世玉宋张胜魏志奎金晓慧
Owner HENAN LIHUA PHARMA
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