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Synthesis method of fluocinolone acetonide intermediate

A fluocinonide acetate and synthesis method technology, applied in the field of fluocinonide acetate intermediates, new intermediates, and fluocinonide acetate intermediates, can solve the problems of no starting material selection and process route improvement, and reduce environmental risks , the reduction of production equipment, the effect of shortening the production process and cycle

Inactive Publication Date: 2017-12-01
天津太平洋化学制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, some domestic related patents are also related to the synthesis methods of some intermediates in the above two methods, and no improvement has been made in the selection of starting materials and process routes.

Method used

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  • Synthesis method of fluocinolone acetonide intermediate
  • Synthesis method of fluocinolone acetonide intermediate
  • Synthesis method of fluocinolone acetonide intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Dissolve 30 g of compound I in 100 mL of ethyl acetate, add benzoyl chloride and 1 mL of trifluoromethanesulfonic acid at 30°C, react for 1 to 5 hours, then add 5 mL of pyridine to quench, and evaporate the solvent to dryness to obtain compound II.

[0022] Dissolve compound II in 200mL dimethylformamide, add fluorine reagent at a temperature of 10°C, and react for 3 to 7 hours; wash the reaction solution into 1000mL water, extract with 100mL ethyl acetate; evaporate the ethyl acetate to dryness , to obtain compound III.

[0023] Dissolve compound III in 1000 mL of acetone, add a solution made of 20 g of potassium permanganate, 20 mL of 4M hydrochloric acid, and 400 mL of water at a temperature of 0°C, react for 1 to 3 hours, and quench with 20 g of sodium sulfite; filter, The acetone in the filtrate was evaporated to dryness, washed with water and filtered to obtain compound IV.

[0024] Put compound IV into 150mL hydrogen fluoride aqueous solution at 20°C and react f...

Embodiment 2

[0027] Dissolve 20 g of compound I in 60 mL of tetrahydrofuran, add isopropenyl acetate and 1 g of p-toluenesulfonic acid at 30°C, react for 1 to 5 hours, then add 5 mL of triethylamine to quench, and evaporate the solvent to dryness to obtain compound II.

[0028] Dissolve compound II in 140 mL of acetone, add fluorine reagent at a temperature of 10°C, and react for 3 to 7 hours; wash the reaction liquid into 1000 mL of water, extract with 50 mL of chloroform; evaporate the chloroform to dryness to obtain compound III.

[0029] Dissolve compound III in 600 mL of acetone, add a solution made of 14 g of potassium permanganate, 14 mL of 4M hydrochloric acid, and 300 mL of water at a temperature of 0°C, react for 1 to 3 hours, and quench with 14 g of sodium sulfite; filter, The acetone in the filtrate was evaporated to dryness, washed with water and filtered to obtain compound IV.

[0030] Put compound IV into 100 mL of 20°C hydrogen fluoride in dimethylformamide solution and rea...

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Abstract

The invention relates to a synthesis method of a fluocinolone acetonide intermediate. A steroid compound with a structure I is used as an initiator to synthesize a precursor V of a glucocorticoid drug fluocinolone acetonide, Alpha-fluorine is introduced at a site C6 of the compound I, and an intermediate V is finally obtained through oxidization and introduction of fluorine at a site C9. The initiator raw material is cheap and is easy to obtain, and the synthesis method is stable and economical and reasonable. The synthesis process is as shown in the specification.

Description

Technical field: [0001] The invention belongs to the field of drug synthesis, and relates to a fluocinonide acetate intermediate, in particular to a method for synthesizing the fluocinonide acetate intermediate. The present invention also relates to novel intermediates appearing in the above synthetic routes. technical background: [0002] The technique of existing synthetic fluocinolone acetate mainly contains two kinds of routes: [0003] One is to use 11α, 17α-dihydroxyprogesterone as the raw material to go through 11α hydroxylation, diester, epoxy, fluorine at C6, dehydrogenation at C1, 2, fluorine at C9, dehydration at C16, 17 and then oxidation. Acetone, decolorized and refined to obtain the bulk drug fluocinolone acetate. This process route has a long production cycle and high labor intensity, and the dehydrogenation of C1,2 positions uses highly toxic chemicals, which leads to high process risk and serious environmental pollution. [0004] The other is to use pred...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
CPCC07J5/0061
Inventor 闫晖李媛韩曼玲
Owner 天津太平洋化学制药有限公司
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