1332524-01-2

Usage

Uses

Used in Pharmaceutical Industry:
N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester is used as a key intermediate in the synthesis of MDV3100 (M199800) for its androgen-receptor antagonist properties. N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester helps in blocking androgens from binding to the androgen receptor, preventing nuclear translocation and co-activator recruitment of the ligand-receptor complex, which is essential in treating androgen receptor-related diseases.

Upstream product

• 67-56-1 methanol 
• 1289942-66-0 2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid 
• 749927-69-3 4-bromo-2-fluoro-N-methylbenzanamide 
• 151982-51-3 4-bromo-2-fluorobenzoyl chloride 
• 112704-79-7 2-fluoro-4-bromobenzoic acid 
• 74-88-4 methyl iodide 

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 intermediate

The invention provides a preparation method of an enzalutamide intermediate (formula A). The R group is selected from C1-C4 alkyl, benzyl and phenyl groups, an intermediate (formula A) is synthesizedthrough the method and used for preparing enzalutamide, the reagents such as halogenated hydrocarbon with high toxicity are prevented for producing enzalutamide, meanwhile, by-product impurities generated due to use of inorganic base are avoided, and the yield and purity are high.

A new series of bicalutamide, enzalutamide and enobosarm derivatives carrying pentafluorosulfanyl (SF5) and pentafluoroethyl (C2F5) substituents: Improved antiproliferative agents against prostate cancer

SAR studies on bicalutamide, enobosarm and enzalutamide analogues, functionalised with polyfluorinated groups, is presented. Among the novel bicalutamide and enobosarm derivatives synthesised, several displayed significantly improved in vitro anticancer activity, with IC50 values in the low micromolar range against four different prostate cancer cell lines (LNCaP, VCaP, DU-145 and 22Rv1), showing up to 48-fold increase in comparison with the parent structures. In particular, SF5 enobosarm analogues were found to be most potent compounds, full AR antagonists and with favourable ADME properties. The most promising compound (48a) was evaluated for its in vivo efficacy in PC xenograft mouse model (22Rv1) with results comparable to the standard-of-care docetaxel.

A "one-pot synthesis" method of synthesizing graciousness mixed Lu An

The invention provides a one-pot method for synthetizing enzalutamide and belongs to the field of medicinal chemical synthesis. The method comprises the following steps: firstly, carrying out copper-catalyzed Buchwald reaction on N-methyl-4-bromo-2-fluoro-benzamide and 2-methyl alanine, adding halogenated hydrocarbon, reacting to generate ester, finally adding a key intermediate 4-isothiocyano-2-(trifluoromethyl) cyanophenyl and carrying out bucherer-Bergs reaction to generate the enzalutamide. The method is simple in operation and high in product yield and has the advantages that the intermediate products are not needed to be separated and directly reacted, so that the process flow cycle is shortened; the final product is easy to separate and purify.

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.

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.