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US 2025/0333385 A1Published application
Diarylhydantoin compounds
AssigneeThe Regents of the University of California
InventorsCharles L. SAWYERS, Michael JUNG, Charlie D. CHEN, Samedy OUK, Derek WELSBIE, Chris TRAN, John WONGVIPAT, Dongwon YOO
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Abstract
The present invention relates to diarylhydantoin compounds, including diarylthiohydantoins, and methods for synthesizing them and using them in the treatment of hormone refractory prostate cancer.
Claims3
-51. (canceled)
A compound of formula
A method of synthesizing a compound of formula
- comprising
- mixing 4-iodoaniline and piperazine-1-carboxylic acid tert-butyl ester in an alcohol to form a first mixture;
- allowing the first mixture to react;
- chromatographing the first mixture to obtain 4-(4-aminophenyl)-piperazine-1-carboxylic acid tert-butyl ester;
- mixing 4-(4-aminophenyl)-piperazine-1-carboxylic acid tert-butyl ester, cyclobutanone, and trimethylsilyl cyanide in dichloromethane to form a second mixture;
- allowing the second mixture to react;
- chromatographing the second mixture to obtain 4-[4-(1-cyanocyclobutylamino)phenyl]-piperazine-1-carboxylic acid tert-butyl ester;
- mixing 4-[4-(1-cyanocyclobutylamino)phenyl]-piperazine-1-carboxylic acid tert-butyl ester and 4-isothiocyanato-2-trifluoromethylbenzonitrile in dimethylformamide (DMF) to form a third mixture;
- allowing the third mixture to react;
- and
- chromatographing the third mixture to obtain the compound 4-{4-[7-(4-cyano-3-trifluoromethylphenyl)-8-(4-cyano-3-trifluoromethyl-phenylthiocarbamoylimino)-6-thioxo-5,7-diazaspiro[3,4]oct-5-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester.
8 more elements
Dependencies are inferred from the claim text.