407577-53-1

Usage

Uses

Used in Pharmaceutical Industry:
7β-Fulvestrant is used as an impurity in the production of Fulvestrant, a drug used for the treatment of hormone receptor-positive metastatic breast cancer. Its presence in the manufacturing process is crucial for the development and efficacy of the final drug product.
Used in Research and Development:
7β-Fulvestrant serves as a valuable compound for research purposes, particularly in the study of the effects and mechanisms of Fulvestrant. It aids in understanding the differences between the Rand S-isomers of Fulvestrant and their respective roles in cancer treatment.
Used in Quality Control:
7β-Fulvestrant is utilized in the quality control process of Fulvestrant production. By monitoring the levels of this impurity, manufacturers can ensure the safety, efficacy, and consistency of the final drug product.
Used in Drug Synthesis:
As the S-isomer of Fulvestrant, 7β-Fulvestrant plays a role in the synthesis of the drug. It may be used as a starting material or intermediate in the production of Fulvestrant, contributing to the overall manufacturing process.

Upstream product

• 862700-63-8 1-iodo-9-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-nonane 
• 55362-80-6 9-bromononan-1-ol 
• 76334-30-0 9-iodononan-1-ol 
• 862700-62-7 methanesulfonic acid 9-(4,4,5,5,5-pentafluoro-pentyl-sulfanyl)-nonyl ester 
• 875573-63-0 (+)-3-oxo-(7α)-[9-bromononyl]estr-4-en-17β-ylacetate 
• 2590-41-2 6-dehydro-19-nortestosterone acetate 
• 89359-54-6 9-bromo-1-nonene 
• 160598-75-4 1-(acetylsulfanyl)-4,4,5,5,5-pentafluoropentane 
• 875573-66-3 (+)-(7α)-[9-bromononyl]estra-1,3,5(10)-triene-3-ol-17β-yl acetate 
• 148757-88-4 4,4,5,5,5-pentafluoropentane-1-thiol 
• 1221256-46-7 (7R,13S)-3-methoxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol 
• 261506-24-5 fulvestrant 17β-acetate 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 
• 875573-60-7 7α-[9-(tert-butyldimethylsiloxy)nonyl]estr-4-ene-17β-acetate-3-one 

Downstream Products

• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 

Relevant academic research and scientific papers

Impurity control method of fulvestrant

The invention belongs to the field of pharmaceutical chemicals, and relates to a fulvestrant impurity control method, which is characterized in that from the introduction of chiral carbon to the synthesis of a fulvestrant intermediate compound represented by a formula VII-1, multi-step and step-by-step control is performed on 7beta isomer impurities, so that the 7beta isomer content of the VII-1 compound is between 0.1% and 0.3%, and finally the qualified fulvestrant bulk drug with stable quality is prepared. The impurity control method is simple to operate, low in production cost and high intotal yield, and can be applied to large-scale industrial production.

Method for preparing fulvestrant and intermediates

The invention relates to a method for preparing fulvestrant and intermediates, particularly to a method for preparing a fulvestrant intermediate. According to the method, estradiol is used as a starting raw material, and is linked to a protecting group to obtain an intermediate 1; the benzyl site of the intermediate 1 is hydroxylated to obtain an intermediate 2; the intermediate 2 is oxidized to obtain an intermediate 3; the intermediate 3 and an intermediate 4 (1,9-dibromo nonane is subjected to iodination to obtain an intermediate 4, ie., 1,9-diiodononane) are subjected to a condensation reaction to obtain an intermediate 5 (a compound represented by a formula I); the intermediate 5 and an intermediate 7 (4,4,5,5,5-pentafluoropentanol and p-toluenesulfonyl chloride are condensed, and thecondensed product reacts with thiourea to obtain p-toluenesulfonic acid pentafluorothiourea salt) are subjected to a reaction to obtain an intermediate 8; the intermediate 8 is subjected to deprotection-reduction to obtain an intermediate 9; and the intermediate 9 is oxidized to obtain a target product. The method has the advantages of simple operation process, high yield of fulvestrant and highpurity of fulvestrant, and is suitable for industrial mass production.

Processes and intermediates for preparing fulvestrant

The present invention provides a method and an intermediate for preparing fulvestrant, and relates to a method for preparing fulvestrant, and an intermediate (5) of fulvestrant, and a synthetic methodthereof. The method provided by the invention can be used for obtaining high-purity fulvestrant, and is suitable for industrial mass production.

Fulvestrant intermediate

The present invention provides a new fulvestrant intermediate compound represented by a formula III, wherein the mass spectrum of the intermediate III is [M+H]237.2082. According to the present invention, with the application of the intermediate to prepare fulvestrant, the route is simple, the yield and the purity of each reaction intermediate are high, the high-purity fulvestrant can be obtained through re-crystallization without column chromatography, and the method is suitable for industrial production.

Fulvestrant preparation method

The invention provides a new fulvestrant synthesis method, which has characteristics of mild reaction condition, simple route and high yield and high purity of each reaction intermediate, can obtain high-purity fulvestrant through re-crystallization without column chromatography, and is suitable for industrial production. The specific technical scheme of the present invention comprises that a compound represented by a formula I and a reagent are subjected to a halogenation reaction in a solvent to generate a compound represented by a formula II; the compound represented by the formula II and thiourea are subjected to a reflux reaction in a solvent to generate a compound represented by a formula III; the compound represented by the formula III and a compound represented by a formula IV aresubjected to a nucleophilic substitution reaction and a hydrolysis reaction in an alkali solution and an organic solvent to generate a compound represented by a formula V; and the compound representedby the formula V is oxidized with an acetic acid hydrogen peroxide oxidation system in a solvent to obtain fulvestrant.

Sulfoxide and sulfone compounds, as well as selective synthesis method and application thereof

The invention discloses a method for selectively synthesizing a sulfoxide compound shown as a formula (II) and a sulfone compound shown as a formula (III). In a reaction solvent, thioether (I) is usedas a reaction raw material and oxygen as an oxidation reagent, under the catalytic action of visible light and a photosensitive reagent; under the assistance of an additive, when a large-polarity proton-containing additive such as an acid and an alcohol or a solvent or an additive with excellent electron donating ability is used, a sulfoxide compound (II) is selectively generated; and when a small-polarity aprotic additive or a solvent is used, a sulfone compound (III) is selectively generated. The synthesis method has the advantages of easily available and cheap raw materials, simple reaction operation, mild reaction conditions, high yield and excellent functional group tolerance. According to the invention, synthesis and modification of some medicines are realized, and an efficient method for selectively constructing sulfoxide and sulfone compounds is provided for medicinal chemistry research.

Improved method for recovering fulvestrant with unqualified isomer ratio

The invention relates to an improved method for recovering fulvestrant with an unqualified isomer ratio. A halide is adopted as a reduction catalyst for replacing reductants with potential safety hazard and environmental pollution in the prior art, so that the discharge of three wastes (waste gas, waste water and industrial residue) is reduced, the recovery rate of the fulvestrant is greatly improved, the recovery rate of the unqualified fulvestrant can reach about 70%, and thus the improved method is beneficial for industrial popularization.

Preparing method of fulvestrant

The invention relates to a preparing method of a steroid compound, in particular to preparing of fulvestrant. The compound 1 serves as the initial raw material, or the compound 1 is used for synthesizing the fulvestrant. The method is high in selectivity, the selectivity and yield of a 7-site side chain can be improved, the construction of an aromatic ring is avoided, after-reaction treatment is simple, and operation is easy. Conventional reagents are used, reactions except the catalysis reaction where precious metal is used are more environmentally friendly compared with the prior art, and therefore the certain energy consumption reduction potential is realized.

Preparation of fulvestrant

The invention relates to a preparation method of fulvestrant, in particular to preparation of the fulvestrant realized under the condition of beta-cyclodextrin/NBS through oxidizing a compound shown as a formula I. By using the method, the generation of fulvestrant peroxidating impurities can be completely avoided.