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Synthesis method of fluticasone propionate impurities

A technology of fluticasone propionate and synthesis method, applied in the direction of steroids, organic chemistry, etc.

Active Publication Date: 2019-08-09
BIONNA (BEIJING) MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no synthetic method for fluticasone propionate impurity EP-ZB and impurity EP-ZG in the prior art

Method used

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  • Synthesis method of fluticasone propionate impurities
  • Synthesis method of fluticasone propionate impurities
  • Synthesis method of fluticasone propionate impurities

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Synthesis of compound I

[0037]

[0038] Take a 1.0L three-necked reaction flask, add 30.0g of flumetasone and 165mL of tetrahydrofuran, stir to dissolve, weigh 25.0g of periodic acid and add 225mL of water to dissolve, slowly add the periodic acid solution into the reaction flask, after adding the sample, control the temperature React at 0-20°C for 2 hours; after the reaction is completed, add 225mL of purified water to the reaction solution, control the temperature to 0-20°C, carry out stirring and crystallization for 40min, suction filtration, filter cake rinse with 90mL water, suction filtration, filter cake After drying at 40°C, 28.72 g of off-white solid, ie Compound I, was obtained with a yield of 99.12% and a purity of 98%. Wherein, the periodic acid concentration (mass fraction) is 10%.

[0039] (2) Synthetic impurity EP-ZB

[0040]

[0041]Take a 250mL three-necked reaction flask, add 2.01g of compound I and 25mL of acetone, control the temperatur...

Embodiment 2

[0043] (1) Synthesis of compound I

[0044]

[0045] Take a 1.0L three-necked reaction flask, add 30.0g of flumetasone and 165mL of tetrahydrofuran, stir to dissolve, weigh 25.0g of periodic acid and add 225mL of water to dissolve, slowly add the periodic acid solution into the reaction flask, after adding the sample, control the temperature React at 0-20°C for 2 hours; after the reaction is completed, add 225mL of purified water to the reaction solution, control the temperature to 0-20°C, carry out stirring and crystallization for 40min, suction filtration, filter cake rinse with 90mL water, suction filtration, filter cake After drying at 40°C, 28.72 g of off-white solid, ie Compound I, was obtained with a yield of 99.12% and a purity of 98%.

[0046] (2) Synthesis of Compound IV

[0047]

[0048] Take a 250mL three-necked reaction flask, add 8.02g compound I and 50mL dichloromethane, cool down to 0-10°C, add 0.3mL N,N-dimethylformamide and stir for 20min, then control...

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Abstract

The invention provides a synthesis method of fluticasone propionate impurities. The method specifically includes the step of preparing fluticasone propionate impurities EP-ZB and impurities EP-ZG. Flumethasone serves as the raw material, and a compound I is synthesized; the compound I reacts with a sulfur agent, and reaction products are subjected to postprocessing and silica gel column purifyingto obtain the impurities EP-ZB; the compound I serves as the raw material and reacts with an acylation agent to generate a compound II, and the compound II and the impurities EP-ZB are condensed to generate a compound IV; the compound IV and a sulfur agent react in an organic solvent and are catalyzed by a catalyst to generate a compound V; the compound V and an added acid-binding agent react to generate a compound VI; finally, the compound VI and bromofluoromethane react to generate the impurities EP-ZG. The synthesis method is simple in process route, convenient to operate, high in selectivity and high in yield.

Description

technical field [0001] The invention belongs to the field of drug impurity synthesis, in particular to a synthesis method of fluticasone propionate impurity EP-ZB and impurity EP-ZG. Background technique [0002] Fluticasone propionate is a product launched by GlaxoSmith in the United Kingdom. The main active ingredients of fluticasone propionate are: Fushuliang, Fushudone and Ketingfu, which are used to treat allergic rhinitis and asthma respectively. and dermatitis etc. Fluticasone propionate has the characteristics of high affinity, high specificity and high intrinsic activity, fast onset of action, and few adverse reactions, and is widely used in the world. At present, the high-end preparations of fluticasone propionate in China are all imported varieties, and the domestically produced varieties are mainly creams. Rely on imports. [0003] Respiratory system preparations have extremely high requirements on raw materials, so in order to obtain high-quality raw material...

Claims

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Application Information

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IPC IPC(8): C07J31/00
CPCC07J31/006
Inventor 蔡报彬孙文东杨金金李昊蔡保理
Owner BIONNA (BEIJING) MEDICAL TECH CO LTD
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