![17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene](/Databaselist/images/loading.webp)
80474-45-9Relevant academic research and scientific papers
Fluticasone propionate synthesis method
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Page/Page column 7-15, (2020/02/10)
The embodiments of the invention provide a fluticasone propionate synthesis method, which comprises: a thioesterification reaction: adding a first intermediate, an first organic alkali, dimethylaminothioformyl chloride, sodium iodide and a first organic solvent into a reaction kettle, carrying out a reaction, adding a polar aprotic solvent and water after the reaction, carrying out cooling crystallizing, filtering, washing, and drying to obtain a second intermediate; an alcoholysis reaction: adding the second intermediate, a first inorganic alkali and a second organic solvent into a reaction kettle, carrying out a reaction, adding water or water and an extracting agent after the reaction, extracting, taking the water phase, adding hydrochloric acid in a dropwise manner, crystallizing, filtering, washing, and drying to obtain a third intermediate; and a substitution esterification reaction: adding the third intermediate, a second inorganic alkali and a third organic solvent into a reaction kettle, adding fluorobromomethane, adding hydrochloric acid in a dropwise manner, crystallizing, filtering, washing, and drying to obtain fluticasone propionate. According to the embodiments of the invention, the low-cost production can be realized, and the reaction yield and the purity are high.
Preparation method of fluticasone propionate
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Paragraph 0037-0039, (2019/10/29)
The invention provides a preparation method of fluticasone propionate. The preparation method comprises the following steps that (1) a compound 5 is hydrolyzed in the presence of a base and an alcoholsolvent to obtain a compound 6; and (2) the compound 6 reacts with fluorohalomethane to obtain fluticasone propionate (compound 1) under the condition that a reducing salt is used as a catalyst. According to the preparation method of fluticasone propionate, the reducing inorganic salt is used as the catalyst to greatly reduce the formation of impurities, such as disulfide impurities, sulfhydryl oxide impurities and haloalkylate impurities introduced by sulfhydryl oxides.
METHODS OF PREPARING INTERMEDIATE OF FLUTICASONE PROPIONATE
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Paragraph 0044; 0056, (2016/04/26)
A method of preparing a thioic acid intermediate of fluticasone propionate includes: treating a 17β-[(N,N-dimethyl carbamoyl)thio]carbonyl compound in a solution including an alcohol and an alkali metal hydroxide, an alkaline-earth metal hydroxide, or a mixture thereof to cleave an amide from the 17β-[(N,N-dimethyl carbamoyl)thio]carbonyl compound; treating the solution to separate an aqueous portion; and adding an acid to the aqueous portion to obtain the thioic acid intermediate of fluticasone propionate. A method of preparing fluticasone propionate includes preparing the thioic acid intermediate of fluticasone propionate, and alkylating the thioic acid intermediate of fluticasone propionate to prepare the fluticasone propionate.
Improved synthesis of fluticasone propionate
Zhou, Jiadi,Jin, Can,Su, Weike
, p. 928 - 933 (2014/10/16)
A novel process for the preparation of fluticasone propionate (1), a corticosteroid, is reported. In this paper, compound 2 was used as starting material to prepare 6 by using NaClO or NaBrO which was much cheaper than H 5IO6 as an oxidizing agent. Furthermore, toxic, expensive, and pollutive BrCH2F was replaced by AgNO3 and Selectfluor in decarboxylative fluorination.
PROCESS FOR PREPARING FLUTICASONE PROPIONATE/FUROATE
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, (2014/06/11)
The present invention relates to an improved process for the preparation of substituted Fluticasone derivatives. The invention also reveals the processes for the purification of Fluticasones and related intermediates to provide the highly pure product.
PROCESS FOR SYNTHESIS OF ANDROSTANE 17-BETA CARBOTHIOIC ACID AND RELATIVE COMPOUNDS THEREOF
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Page/Page column 3, (2009/12/02)
A process for synthesis of androstane 17-β carbothioic acid is provided. The process includes mixing an androstane 17-β carboxylic acid and a coupling reagent, and adding an alkanethioic acid to form an androstane 17-β carbothioic acid, wherein the androstane 17-β carbothioic acid has the formula (I): wherein R1 represents hydrogen or haloalkyl groups, R2 represents C1-8 linear alkyl groups, C1-8 branched alkyl groups, C1-6 unsaturated acyclic groups or aromatic groups, R3 represents hydrogen or hydroxyl, R4 represents hydrogen, bromine, chlorine or fluorine and R5 represents hydrogen, bromine, chlorine or fluorine. The process is a one-pot reaction.
METHOD FOR PREPARATION OF FLUTICASONE PROPIONATE
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Page/Page column 2, (2008/12/05)
Taught is a method for preparing S-fluoromethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate (fluticasone propionate). The present method is simple, convenient, and mild, yields highly pure product, and is suitable for use commercially on a large scale.
METHOD FOR THE PREPARATION OF FLUTICASONE PROPIONATE
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Page/Page column 6, (2010/11/30)
Taught is a method for preparing S-fluoromethyl-6α,9α- difluroro-11β-hydroxy-16α-methyl-17α- propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate (fluticasone propionate). The present method is simple, convenient, and mild, yields highly pure product, and is suitable for use commercially on a large scale.
NOVEL 11 BETA - HYDROXYANDROSTA-4-ENE-3-ONES
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Page/Page column 36-37, (2008/06/13)
11 β-hydroxyandrosta-4-ene-3-one, compound of formula (I), and physiologically acceptable salt thereof; wherein R4 represents moiety selected from a group consisting of (A), (B) and (C), with a proviso that when R4 represents moiety (C), Z is S.
