Method for preparing dexamethasone intermediate

A technology for dexamethasone and intermediates, which is applied in the field of preparation of steroid compounds, can solve the problems of low overall yield and high cost, and achieve the effects of improving balanced yield, benefiting environmental protection, and reducing costs

Inactive Publication Date: 2018-06-08
江西赣亮医药原料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] For these two synthetic routes, the yield of cyanation reaction is only 82%. The main reason is that the impurity compound III is inevitably produced during the cyanation reaction process, accounting for more than 12%, resulting in low overall yield and high cost.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of 16α-methyl-4,9(11)-diene-3,17-dione

[0027] Hydrolysis reaction

[0028] At room temperature, add 400ml ethanol to a clean and dry 1000ml three-necked round bottom flask equipped with a thermometer and mechanical stirring, add 25g potassium hydroxide under stirring, stir to clear, add 50g 16α-methyl-5-cyano-9( 11)-ene-3,17-dione, the system immediately dissolves and turns into a brownish-red color. The temperature is raised to 40°C and kept for 1.5h. TLC control reaction is complete (developing solvent: acetone / petroleum ether=1:2), down to 10~15℃, start to add 15% hydrochloric acid dropwise to the system PH=4~5. At this time, a small amount of solid precipitates out of the reaction system. Concentrate under reduced pressure at 45~50℃ until there is no solvent. Add 500ml of water to stir and increase to 45℃. The salt was boiled for 1 h, filtered with suction, the filter cake was rinsed with water to neutrality, and the solid was dried at 50°C to o...

Embodiment 2

[0031] Example 2: Preparation of 16α-methyl-4,9(11)-diene-3,17-dione

[0032] Hydrolysis reaction

[0033] At room temperature, add 400ml methanol to a clean and dry 1000ml three-necked round bottom flask equipped with a thermometer and mechanical stirring. Add 25g sodium hydroxide while stirring. Stir to dissolve and add 50g 16α-methyl-5-cyano-9( 11)-En-3,17-dione, the system immediately dissolves and turns to brownish red. Raise it to 60℃ and keep it for 1h. TLC control reaction is complete (developing solvent: acetone / petroleum ether=1:2), down to 10 ~15℃, start to add 15% hydrochloric acid dropwise to the system PH=4~5. At this time, a small amount of solids are precipitated in the reaction system. Concentrate under reduced pressure at 45~50℃ until there is no solvent. Add 500ml of water to stir to disperse and boil at 45℃. Desalting for 1 h, suction filtration, rinse the filter cake with water to neutrality, and dry the solid at 50°C to obtain 48.5 g of hydrolysate, yield: 97...

Embodiment 3

[0036] Example 3: Preparation of 16α-methyl-4,9(11)-diene-3,17-dione

[0037] Hydrolysis reaction

[0038] At room temperature, add 400ml of acetone to a clean and dry 1000ml three-necked round bottom flask equipped with a thermometer and mechanical stirring, add 25g potassium hydroxide under stirring, stir to dissolve, add 50g 16α-methyl-5-cyano-9( 11)-En-3,17-dione, the system immediately dissolves and turns into a brownish-red color. The temperature is raised to 30°C for 3 hours, and the reaction is completed under TLC control (developing solvent: acetone / petroleum ether = 1:2), down to 10 ~15℃, start to add 15% hydrochloric acid dropwise to the system PH=4~5. At this time, a small amount of solids are precipitated in the reaction system. Concentrate under reduced pressure at 45~50℃ until there is no solvent. Add 500ml of water to stir to disperse and boil at 45℃. Desalting for 1 h, suction filtration, rinse the filter cake with water to neutrality, and dry the solid at 50°C to...

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Abstract

The invention discloses a method for preparing a dexamethasone intermediate. The dexamethasone intermediate is prepared through a hydrolysis reaction and an elimination reaction with a dexamethasone production impurity used as a substrate. The above initial raw material is the impurity generated in the production of the dexamethasone intermediate, does not need to be purchased, and becomes valuables from wastes, and the method also has the advantages of short reaction route, easiness in operation, avoiding of resource wastes, facilitation of environmental protection, improvement of the balancing yield of dexamethasone production, and cost reduction.

Description

Technical field [0001] The invention relates to a method for preparing a steroid compound, in particular to a method for preparing a dexamethasone intermediate by using dexamethasone production impurities as a substrate. Background technique [0002] Dexamethasone, also known as dexamethasone and flumethone, like other glucocorticoids, has anti-inflammatory, anti-endotoxin, immune suppression, anti-shock and enhanced stress response and other pharmacological effects, so it is widely used Each department treats many diseases, such as autoimmune diseases, allergies, inflammations, asthma and dermatology and ophthalmology diseases. So far, my country has become the largest market for dexamethasone. [0003] At present, when dexamethasone is synthesized industrially at home and abroad, most of the key 17 side chains are synthesized through the following reaction routes: [0004] [0005] Or the following reaction route: [0006] [0007] For the two synthetic routes, the yield of the cy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0059
Inventor 杨坤于传云李晓波
Owner 江西赣亮医药原料有限公司
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