Halcinonide preparation method

A synthesis method and compound technology, which is applied in the production of steroids, bulk chemicals, organic chemistry, etc., can solve the problems of expensive raw materials, high production costs, and many by-products, so as to improve product yield and save production costs , The effect of reducing by-products

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

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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

[0036] The invention discloses a preparation method of halcinonide, 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.

[0037] 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

[0039] Embodiment 1: the preparation of formula II compound

[0040]

[0041] 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. 5.1 grams (16.4 mmol) of compound I and 4.3 grams (105 mmol) of sodium hydroxide are added to the reaction bottle, and stirred for 10- 30min, under the condition of avoiding light, add 8.0g (25.0mmol) iodobenzene diacetate at one time, naturally rise to room temperature and react for 6-8 hours. The resulting solid was added to 150 mL of tetrahydrofuran, and 3.1 g (26.1 mmol) of thionyl chloride was added at room temperature. After the reaction was completed, quenched with saturated sodium bicarbonate solution, separated, washed with water, dried the organic phase, and removed the solvent under reduced pressure to obtain the formula Compound II was 5.7 g (14.6 mmol), and the yield was 89%.

Embodiment 2

[0042] Embodiment 2: the preparation of formula III compound

[0043]

[0044]150mL of acetone was used as a solvent, 4.7g (12.0mmol) of the compound of formula II was added, the temperature was lowered to -5~5°C, 1.8mL of about 2.2g (48.4mmol) of formic acid was added as a catalyst, and 3.3g (21.1mmol) 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 4.3 g (10.4 mmol), yield 87%.

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Abstract

The invention provides a brand-new synthesis route for preparing halcinonide. Used raw materials are cheaper and available. The method comprises the steps that: the reacted raw materials are hydroxylated and then chlorinated, selective oxidation of a five-membered ring double bond is conducted, a carbonyl protecting group is removed, an oxidized dihydroxyl group is protected, then a six-membered ring double bond is epoxidized, an open ring is fluoridized so as to obtain a halcinonide product. The reaction process is easy to operate, yield is higher in each step, purity of the obtained productis also higher, formation of byproducts is effectively avoided, production cost is reduced, and the method is advantageous to industrial production.

Description

technical field [0001] The application relates to a preparation method of halcinonide, an adrenocortical hormone asthma treatment drug. Background technique [0002] Halcinonide, chemical name: 9-fluoro-11b, 21-dihydroxy-16a, 17-[(1-methylethylene)bis(oxy)]-pregna-1,4-diene -3,20-dione (21-chloro-9-α-fluoro-11-β-hydroxy-16-α,17-α-isopropylidenedioxypregn-4-ene-3,20-dione), CAS registration number: 3093 -35-4, is a synthetic potent glucocorticoid with strong local anti-inflammatory effect and less likely to cause systemic side effects. It is mainly used for psoriasis and eczematous dermatitis with remarkable curative effect. [0003] [0004] At present, the production process of halcinonide mainly uses chlorotetraene compounds as raw materials, but the chlorotetraene compounds are expensive, and using them as raw materials increases the production cost. [0005] In order to solve the above technical problems, the present application provides a new method for preparing h...

Claims

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Application Information

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IPC IPC(8): C07J71/00
CPCY02P20/55C07J71/0031
Inventor 宋德成
Owner TIANJIN PACIFIC PHARMA
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