389571-69-1

Upstream product

• 54962-75-3 [3-bromo-5-(trifluoromethyl)phenyl]amine 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 41253-01-4 1-iodo-3-nitro-5-(trifluoromethyl)benzene 

Downstream Products

• 641571-11-1 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline 
• 641571-16-6 3-(5-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline 
• 259667-88-4 3-(2-chlorophenyl)-1-(2-diethylaminoethyl)-3(R)-hydroxy-6-iodo-4-trifluoromethyloxindole 
• 259667-87-3 3-(2-chlorophenyl)-1-(2-diethylaminoethyl)-3(S)-hydroxy-6-iodo-4-trifluoromethyloxindole 
• 259667-84-0 3-(2-chlorophenyl)-1-(2-diethylaminoethyl)-3-hydroxy-6-iodo-4-trifluoromethyloxindole 
• 389571-74-8 (-)-3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-(3R)-hydroxy-4-trifluoromethyloxindole 
• 259667-89-5 (3S)-3-(2-chlorophenyl)-1-(2-(diethylamino)ethyl)-3-hydroxy-2-oxo-4-(trifluoromethyl)indoline-6-carbonitrile 
• 259667-93-1 3-(2-chlorophenyl)-6-cyano-1-(2-diethylaminoethyl)-3-hydroxy-4-trifluoromethyloxindole 

Relevant academic research and scientific papers

METHOD FOR PRODUCING ANILINE COMPOUND

PROBLEM TO BE SOLVED: To provide a method for highly selectively producing 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline from 3-bromo-5-trifluoromethylaniline. SOLUTION: There is provided a method for producing 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, which comprises (1) a step of obtaining 3-iodo-5-trifluoromethylaniline by reacting 3-bromo-5-trifluoromethylaniline and an iodizing agent in a solvent in the presence of a transition metal catalyst and a compound represented by the formula [6] (wherein, R1 and R2 are the same or different and represents an alkyl group, W represents a divalent hydrocarbon group) and (2) a step of obtaining 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline by reacting the 3-iodo-5-trifluoromethylaniline obtained in the step (1) and 4-methyl-1H-imidazole in the presence of a base. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Oxindole derivatives as orally active potent growth hormone secretagogues

A series of substituted oxindole derivatives was synthesized and evaluated for growth hormone (GH) releasing activity using cultured rat pituitary cells. (+)-6-Carbamoyl-3-(2-chlorophenyl)-(2-diethylaminoethyl)- 4-trifluoromethyloxindole (SM-130686, 37S) was found to have potent activity (EC50 = 3.0 nM), while the other enantiomer 37R had reduced activity. The absolute configuration of 37S was confirmed by X-ray crystallographic analysis. Compound 37S showed a good pharmacokinetic profile in rats with 28% oral bioavailability at 10 mg/kg and excellent in vivo activity as evidenced by a significant weight gain after 4 days of oral administration at 10 mg/kg twice a day. Compound 37S displaced the binding of 35S-MK-677 to human GHS-R with an IC50 value of 1.2 ± 0.2 nM.