262295-87-4

Upstream product

• 262295-90-9 (2S,5R)-4-(4-benzyl-2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile 
• 50893-53-3 carbonochloridic acid 1-chloro-ethyl ester 
• 2815-34-1 2,5-dimethyl-piperazine 
• 194853-86-6 4-fluoro-2-(trifluoromethyl)benzonitrile 
• 216532-43-3 (-)-(2R,5S)-1-benzyl-2,5-dimethylpiperazine 
• 262295-89-6 (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione 

Downstream Products

• 648423-78-3 (2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethylpiperazine-1-carbonyl chloride 

Relevant academic research and scientific papers

(+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6- (trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist

A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)4-[4-cyano-3-(trifluoromethyl)phenyl]-2, 5-dimethyl-N-[6(triflouromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.

N-PHENYL-(2R,5S)DIMETHYLPIPERADINE DERIVATIVE

The present invention relates to a novel N-phenyl-(2R,5S)dimethylpiperazine derivatives useful as antiandrogenic agent which exhibits a sufficient prostate gland reducing effect as compared with conventional compounds and are excellent in oral activity. The compound of the present application is useful in preventing or treating prostate cancer, benign prostatic hyperplasia, and the like. The present invention also provides a novel intermediate useful in producing the compound of the present invention.

Cyanophenyl derivative

This application relates to a piperazino-substituted novel cyanophenyl derivative in which a substituted carbamoyl or substituted sulfamoyl group having an aryl, heterocyclic or the like group that may have a substituent group is bonded to one nitrogen atom on the piperazine ring. The compound of this application has an anti-androgen action and is useful in preventing or treating prostatic cancer, benign prostatic hyperplasia and the like diseases.