1289942-55-7

Usage

Uses

Used in Pharmaceutical Industry:
4-[1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-1-methyl-ethylamino]-2-fluoro-N-methyl-benzamide is used as an impurity in Enzalutamide, an androgen-receptor antagonist. Enzalutamide blocks androgens from binding to the androgen receptor, preventing nuclear translocation and co-activator recruitment of the ligand-receptor complex. This makes it a potential candidate for the treatment of prostate cancer and other androgen-dependent conditions.
As an impurity, it is important to monitor and control the levels of 4-[1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-1-methyl-ethylamino]-2-fluoro-N-methyl-benzamide in Enzalutamide to ensure the safety and efficacy of the drug. This can be achieved through quality control measures and analytical techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry.

Upstream product

• 749927-69-3 4-bromo-2-fluoro-N-methylbenzanamide 
• 208122-09-2 2-amino-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylpropanamide 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 1289942-66-0 2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid 
• 151982-51-3 4-bromo-2-fluorobenzoyl chloride 
• 112704-79-7 2-fluoro-4-bromobenzoic acid 

Downstream Products

• 915087-33-1 enzalutamide 
• 1242137-15-0 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-imidazolidinethione-1-yl)-2-fluorobenzoic acid 

Relevant academic research and scientific papers

Preparation method of enzalutamide of formula (VIII)

The invention discloses a preparation method of enzalutamide of formula (VIII). The method comprises the following steps: carrying out a condensation reaction on a compound of formula (I) and an aminoprotecting group PG-containing compound of formula (II) to produce a compound of formula (III); carrying out a protecting group PG removal reaction on the compound of formula (III) to form a compoundof formula (IV); carrying out a coupling reaction on the compound of formula (IV) and a compound of formula (V) at 25-160 DEG C to form a compound of formula (VI); and converting the compound of formula(VI-a) into a compound of formula (VII) when W is a C1-8 alkoxy group, and converting the compound of formula (VI-b) into into the compound of the formula (VIII) when the W is a methylamino group.The method has the advantages of high yield, omitting of the production of an intermediate isothiocyanate with poor stability, mild reaction conditions, simplicity in operation, and cheap and easily available reagents, is suitable for small-scale preparation in the laboratory, and is also suitable for large-scale industrial production.

Method for preparing enzalutamide synthesis intermediate compound represented by formula (III)

The invention discloses a method for preparing an enzalutamide synthesis intermediate compound represented by a formula (III), wherein the compound represented by the formula III is an important intermediate for preparing an anti-prostate cancer drug enzalutamide. The method comprises: carrying out a reaction by using a compound represented by a formula (I) and a compound represented by a formula(II) as raw materials to produce the compound represented by the formula (III).

Preparation method of enzalutamide

The invention provides a preparation method of enzalutamide. The method comprises the following steps: condensing an initial raw material 2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methylpropioric acid and enol to obtain an intermediate I, and reacting the intermediate I with The method has the advantages of simple operation, suitableness for industrial production, high yield and high purity.

Substituted Phenylcarbamoyl Alkylamino Arene Compounds and N,N'-BIS-Arylurea Compounds

Substituted phenylcarbamoyl alkylamino arenes; substituted phenylthiocarbamyl alkylamino arenes; substituted phenylcarbamoyl alkylamino heteroarenes; substituted phenylthiocarbamyl alkylamino heteroarenes; N-substituted aryl, N′-substituted aryl urea compounds; N-substituted aryl, N′-substituted heteroaryl urea compounds; N-substituted aryl, N′-substituted aryl thiourea compounds and N-substituted aryl, N′-substituted heteroaryl thiourea compounds are provided and may find use as androgen receptor modulators. The compounds may find particular use in treating prostate cancer, including castration-resistant prostate cancer and/or hormone-sensitive prostate cancer.

PROCESSES FOR THE SYNTHESIS OF DIARYLTHIOHYDANTOIN AND DIARYLHYDANTOIN COMPOUNDS

Processes are provided for the synthesis of diarylthiohydantoin and diarylhydantoin compounds, such as compounds of the formula: wherein X, Y1, Y2, R1, and R2 are as defined herein. Medicinal products containing the same find particular use in treating prostate cancer, including castration-resistant prostate cancer and/or hormone-sensitive prostate cancer.