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Method for preparing hydrocortisone acetate

A technology of fludrocortisone and acetate, applied in the field of medicinal chemistry, can solve the problems of high equipment requirements, high corrosion, inconvenient operation, etc., and achieve the effect of reducing high corrosion, less dosage, and safe and convenient operation

Inactive Publication Date: 2018-04-17
江苏福锌雨医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the literature, commonly used fluorinating reagents include anhydrous hydrogen fluoride [Fried, J.; Sabo, E.F., J.Am.Chem.Soc.1957,79,1130.] and 52-55% hydrogen fluoride aqueous solution [US2894007]. The former uses Anhydrous hydrogen fluoride gas is inconvenient to operate, highly corrosive and toxic, and has high requirements for equipment; the latter uses hydrogen fluoride aqueous solution, and needs to use strong acids such as perchloric acid in the reaction, and the reaction by-products are many and difficult to control, so Using the above process for industrial production faces many problems

Method used

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  • Method for preparing hydrocortisone acetate

Examples

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Effect test

Embodiment 111

[0023] Example 1 Preparation of 11β, 17α, 21-trihydroxy-9α-fluoropregna-4-ene-3,20-dione-21-acetate

[0024] Compound 1 (1g, 2.49mmol) was dissolved in 20ml of dichloromethane, cooled to 0-10°C, and 5ml of 40% hydrofluoric acid aqueous solution and 5ml of 60% perchloric acid aqueous solution were added. At 0-10°C, react for 2 hours. After the reaction, add 50ml of water, extract the water phase twice with 50ml of dichloromethane × 2, combine the dichloromethane phases, wash with water until neutral, dry over anhydrous sodium sulfate, concentrate under reduced pressure to obtain a foamy solid, pass through the column Chromatographic purification of fludrocortisone acetate.

Embodiment 211

[0025] Example 2 Preparation of 11β, 17α, 21-trihydroxy-9α-fluoropregna-4-ene-3,20-dione-21-acetate

[0026] Compound 1 (1g, 2.49mmol) was dissolved in 20ml of dichloromethane, cooled to 0-10°C, and 5ml of 50% hydrofluoric acid aqueous solution and 5ml of 60% perchloric acid aqueous solution were added. At 0-10°C, react for 2 hours. After the reaction, add 50ml of water, extract the water phase twice with 50ml of dichloromethane × 2, combine the dichloromethane phases, wash with water until neutral, dry over anhydrous sodium sulfate, concentrate under reduced pressure to obtain a foamy solid, pass through the column Chromatographic purification of fludrocortisone acetate.

Embodiment 311

[0027] Example 3 Preparation of 11β, 17α, 21-trihydroxy-9α-fluoropregna-4-ene-3,20-dione-21-acetate

[0028] Compound 1 (1g, 2.49mmol) was dissolved in 20ml of dichloromethane, cooled to 0-10°C, and triethylamine hydrogen trifluoride (1ml, about 8.6mmol) was added. At 0-10°C, react for 2 hours. After the reaction, add 5ml of water, extract the water phase twice with 5ml of dichloromethane × 2, combine the dichloromethane phases, wash with water until neutral, dry over anhydrous sodium sulfate, concentrate under reduced pressure to obtain a foamy solid, pass through the column Chromatographic purification of fludrocortisone acetate.

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Abstract

The invention relates to a method for preparing hydrocortisone acetate. The method comprises the following steps: 9beta, 11beta-epoxy-17alpha-dihydroxypregn-4-ene-3,20-dione-21-acetate is subjected toa ring-opening reaction with a fluorinating reagent, wherein the fluorinating reagent is an organic amine salt or solution of hydrogen fluoride. The reagent and conditions for ring-opening fluorination of epoxy compounds in key process steps are mainly improved, organic amine salt of hydrogen fluoride substitutes for high-toxicity and high-corrosiveness hydrogen fluoride gas, a small quantity ofthe fluorinating reagent is used, and the method is safe and convenient to operate and suitable for industrial production.

Description

field of invention [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of fludrocortisone acetate. Background technique [0002] Fludrocortisone acetate, also known as fludrocortisone acetate, 9α-fluorocortisone acetate, 9α-fluorocortisone acetate, etc., its chemical name is: 11β, 17α, 21-trihydroxy-9α - Flupregna-4-ene-3,20-dione-21-acetate, the commercially available dosage form is divided into tablets and ointment. This product is an adrenal corticosteroid drug, a medium-effect corticosteroid, has anti-inflammatory and anti-allergic effects, can inhibit the proliferation of connective tissue, reduce the permeability of capillaries and cell membranes, reduce inflammatory exudation, inhibit histamine and Formation and release of other inflammatory mediators. It is mainly used for the replacement treatment of adrenal insufficiency, and can be used externally for allergic dermatitis, contact dermatitis, seborrh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
CPCC07J5/0053
Inventor 陈鹏李健华孙政崔一民
Owner 江苏福锌雨医药科技有限公司
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