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Triamcinolone acetonide acetate preparation method

A technology of triamcinolone acetonide acetate and a synthetic method, which is applied in the field of preparation of triamcinolone acetonide acetate, can solve the problems of expensive raw materials, high production costs, and many by-products, and achieve product yield improvement, production cost saving, and by-product Reduced effect

Inactive Publication Date: 2018-03-09
TIANJIN PACIFIC PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is aimed at the disadvantages of high production cost, low yield, many by-products, expensive raw materials and unavailable raw materials in the industrial process production process in the prior art

Method used

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preparation example Construction

[0040] The invention discloses a preparation method of triamcinolone acetonide acetate, and those skilled in the art can learn from the content of this article and appropriately improve the process parameters to realize it. It needs to be pointed out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention, and relevant personnel can obviously make changes without departing from the content, spirit and scope of the present invention. Changes or appropriate changes and combinations are made to the content described herein to realize and apply the technology of the present invention.

[0041] In the present invention, unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art.

Embodiment 1

[0043] Embodiment 1: the preparation of formula II compound

[0044]

[0045] At a temperature of -5 to 5°C, 100mL of methanol is used as a solvent, and the reaction bottle is placed in an ice-water bath to control the low temperature. 5.4 grams (17.5 mmol) of compound I and 4.2 grams (105 mmol) of sodium hydroxide are added to the reaction bottle, and stirred for 10- 30min, under dark conditions, add 8.5g (26.3mmol) iodobenzene diacetate at one time, naturally rise to room temperature and react for 6-8 hours, TLC monitors the reaction process, add 20g (141mmol) methyl iodide dropwise, continue the reaction, wait After the reaction was completed, the solvent was removed under reduced pressure, extracted with 100 mL of ethyl acetate and 20 mL of water, the organic phase was washed with water, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 6.3 grams (16.3 mmol) of the compound of formula II with a yield of 93 %.

Embodiment 2

[0046] Embodiment 2: the preparation of formula III compound

[0047]

[0048] 150mL of acetone was used as a solvent, 7.1g (18.4mmol) of the compound of formula II was added, the temperature was lowered to -5~5°C, 2.8mL of about 3.4g (73.4mmol) of formic acid was added as a catalyst, and 5.2g (33.1mmol) of potassium permanganate was added Oxidation reaction, TLC monitors the reaction process. After the reaction is completed, excess potassium permanganate is treated with saturated sodium sulfite solution, insoluble solids are removed by filtration, washed with acetone, decolorized by activated carbon, solids are removed by filtration, the solvent is removed under reduced pressure, and recrystallization with pure water yields formula III Compound 6.8 g (16.2 mmol), yield 88%.

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Abstract

The invention provides a full-novel synthesizing route for preparing triamcinolone acetonide acetate. According to the full-novel synthetic route, utilized raw materials have lower cost and more easiness in obtaining. The synthetic route comprises the steps of hydroxylating reaction raw materials and protecting, then selectively oxidizing five-membered ring double bonds, removing a protecting group, then protecting oxidized di-hydroxyl, then epoxidizing six-membered ring double bonds, performing open-ring fluorination and esterfying hydroxyl to obtain a triamcinolone acetonide product. A reaction process has easiness in operation, yields of all the steps are higher, obtained products have higher purities, byproduct generation is effectively avoided, production cost is reduced, and industrial production is facilitated.

Description

technical field [0001] The application relates to a preparation method of triamcinolone acetonide acetate, an adrenocortical hormone asthma treatment medicine. Background technique [0002] Triamcinolone acetonide Acetate, chemical name: 9-fluoro-11b, 21-dihydroxy-16a, 17-[(1-methylethylene)bis(oxygen)]-pregna-1,4 -Diene-3,20-dione-21-acetate (16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione-21- Acetate), CSA registration number: 3870-07-3, is a medium-effect glucocorticoid, the effect is similar to hydrocortisone, it has anti-inflammatory, anti-itching and vasoconstrictive effects, and the effect of water and sodium retention is weak. The inflammatory effect is strong and long-lasting, and its effectiveness is 5-20 times greater than that of hydrocortisone. Triamcinolone acetate is used for eczema and dermatitis. It is a long-acting glucocorticoid drug widely used in dermatology in my country. It is a derivative of triamcinolone (triamcinolone), ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
CPCY02P20/55C07J71/0031
Inventor 宋德成
Owner TIANJIN PACIFIC PHARMA
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