Synthetic method of fluocinonide

A technology of fluocinolone acetate and a synthesis method, applied in the directions of steroids, organic chemistry, etc., can solve the problems of high environmental harm, complicated operation, many by-products, etc., and achieves less environmental pollution, optimized reaction conditions, and less risk. Effect

Active Publication Date: 2022-01-07
SHANDONG GUYUCHUN BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of the above problems, the present invention proposes a synthetic method of fluocinonide acetate, which solves the problems of cu

Method used

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  • Synthetic method of fluocinonide
  • Synthetic method of fluocinonide
  • Synthetic method of fluocinonide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A kind of synthetic method of fluocinolone acetate, its reaction scheme is:

[0021]

[0022] The specific steps are:

[0023] Add 1 mol of compound A to dichloromethane, add 1.3 mol of N-fluorobisbenzenesulfonamide to it at 20°C, stir well, then add 0.008 mol of free radical initiator, stir for 3 hours, use 10% mass fraction The pH of the system is adjusted to be neutral with an aqueous solution of sodium hydroxide, concentrated under reduced pressure, and crystallized from ethanol to obtain fluocinolone acetate with a yield of 92.8% and a purity of 99.2%; the free radical initiator is selected from azobisisobutyronitrile.

Embodiment 2

[0025] A kind of synthetic method of fluocinolone acetate, its reaction scheme is:

[0026]

[0027] The specific steps are:

[0028] Add 1 mol of compound A into dichloromethane, add 1.5 mol of N-fluorobisbenzenesulfonamide to it at 25°C, stir well, then add 0.012 mol of free radical initiator, stir for 2 hours, use 10% mass fraction Sodium hydroxide aqueous solution adjusts the pH of the system to be neutral, concentrates under reduced pressure, and ethanol crystallizes to obtain fluocinonide acetate with a yield of 95.3% and a purity of 99.5%; the free radical initiator is selected from azobisisoheptanonitrile.

Embodiment 3

[0030] A kind of synthetic method of fluocinolone acetate, its reaction scheme is:

[0031]

[0032] The specific steps are:

[0033] Add 1 mol of compound A to dichloromethane, add 1.4 mol of N-fluorobisbenzenesulfonamide to it at 22°C, stir well, then add 0.010 mol of free radical initiator, stir for 2.5 h, and use a mass fraction of 10% The aqueous solution of sodium hydroxide was used to adjust the pH of the system to be neutral, concentrated under reduced pressure, and crystallized from ethanol to obtain fluocinolone acetate with a yield of 94.7% and a purity of 99.1%; the free radical initiator was selected from benzoyl peroxide.

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthesis method of fluocinonide. According to the preparation method, triamcinolone acetonide acetate is taken as a raw material, N-fluorobenzenesulfonamide and a free radical initiator are added into the triamcinolone acetonide acetate for reaction, and fluocinonide acetate is obtained. According to the method, the problems of complicated operation, more byproducts, dangerous reagents and great environmental harm in the process of easily adding fluorine into fluorine acetate are solved, the yield is increased, and large-scale production is easier.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and in particular relates to a method for synthesizing fluocinolone acetate. Background technique [0002] Fluocinonide, also known as fluocinonide acetate, Chinese name: 11β-hydroxyl-16α,17-[(1-methylethylene)-bis(oxygen)]-21-(acetyloxy)-6α ,9-difluoropregna-1,4-diene-3,20-dione, is a potent glucocorticoid steroid that is used topically as an anti-inflammatory agent in the treatment of skin conditions such as eczema. Its chemical structure is: [0003] . [0004] In the 04th issue of "China Pharmaceutical Industry Journal" in 1982, the fluorination process in the fluorinated industry improvement in the synthesis of fluocinolone was dissolved in acetone as a substrate, and perchloryl fluoride was introduced at 40-45 ° C, and the reaction was about 15-16 hours. After the crude product is obtained, the 6-position fluorine is obtained through acetic acid-hydrochloric acid trans...

Claims

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Application Information

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IPC IPC(8): C07J71/00
CPCC07J71/0031
Inventor 杨凯袁文博赵春华王文静靳安琪
Owner SHANDONG GUYUCHUN BIOTECHNOLOGY CO LTD
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