Preparation method of ciclesonide

A fluocinolone and synthetic method technology, which is applied in the production of steroids, bulk chemicals, organic chemistry, etc., can solve the problems of expensive raw materials, high production cost, and many by-products, etc., and achieves improved product yield and production cost. The effect of saving and reducing by-products

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

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Problems solved by technology

[0007] 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 method of ciclesonide
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  • Preparation method of ciclesonide

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preparation example Construction

[0034] The invention discloses a preparation method of fluocinolone, 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.

[0035] 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

[0037] Embodiment 1: the preparation of formula II compound

[0038]

[0039] At a temperature of -5 to 5°C, 100mL of methanol was used as a solvent, and the reaction bottle was placed in an ice-water bath to control the low temperature. 5.72 grams (17.5 mmol) of compound I and 4.2 grams (105 mmol) of sodium hydroxide were 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 6.66 grams (16.5 mmol) of the compound of formula II, with a yield of 94.1 %.

Embodiment 2

[0040] Embodiment 2: the preparation of formula III compound

[0041]

[0042] 150mL of acetone was used as a solvent, 7.5g (18.5mmol) 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 6.9 g (15.74 mmol), yield 85.1%.

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Abstract

The invention provides a novel synthesis route for preparing ciclesonide. Adopted raw materials are cheaper and easier to obtain. After the reaction raw materials are hydroxylated, the double bond ofthe five-membered ring is then selectively oxidated, the oxidated dihydroxyl groups are then protected, the double bond of the six-membered ring is then selectively epoxidated, and after fluorinationand ring opening, the protecting groups for the carbonyl groups are removed, so that the ciclesonide product is obtained. The reaction process is easy to operate, yield in each step is higher, the purity of the obtained product is higher as well, the production of byproducts is effectively prevented, and the production cost is reduced, which is favorable for industrial production.

Description

technical field [0001] The application relates to a preparation method of fluocinolone, an adrenocortical hormone asthma treatment drug. Background technique [0002] Fluocinolone (ciclesonide), chemical name: 11β, 21-dihydroxy-16α, 17-[(1-methylethylene)-bis(oxygen)]-6α, 9-difluoropregna-1,4- Diene-3,20-dione, CSA Registry No.: 67-73-2. [0003] [0004] fluocinolone [0005] At present, the production process of fluocinolone has the disadvantages of low yield and many by-products. In short, the production cost of fluocinolone in the prior art remains high, and there is a need to further reduce the production cost and be suitable for industrialization. [0006] In order to solve the above-mentioned technical problems, the application provides a new method for preparing fluocinolone, which adopts cheaper and easier-to-obtain reaction raw materials, and obtains a method for preparing fluocinolone with a relatively higher total yield through multiple synthesis steps . ...

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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