328955-57-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Amino-4-trifluoromethylquinolin-2(1H)-one is used as an intermediate in the synthesis of LGD-2226 (L397615), an orally active potent and selective androgen receptor modulator. This modulator is utilized in the treatment of muscle wasting and osteoporosis, as it has been shown to have an anabolic effect on muscle and bone tissue. 6-Amino-4-trifluoromethylquinolin-2(1H)-one's unique structure allows for the development of targeted therapies that can help improve the quality of life for patients suffering from these conditions.

Synthesis

6-Amino-4-trifluoromethylquinolin-2(1H)-one is obtained by reacting Nitro-compound with hydrogen in the presence of 5% Pd/C.Experimental Procedure：A suspension of the 17.0 g 6-Nitro-4-trifluoromethylquinolin-2(1H)-one in 400 ml ethanol in a 1 L round flask was flushed with argon and 2.0 g 5% Pd/C was added. The mixture was stirred under a hydrogen atmosphere for 2 days. Then filtered through silica and washed with 1500 mL ethanol. The filtrate was evaporated under vacuum to yield 14.0 g of a bright yellow solid 6-Amino-4-trifluoromethylquinolin-2(1H)-one (92%).

Upstream product

• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 836-31-7 4,4,4-trifluoro-3-oxo-N-phenylbutyramide 
• 62-53-3 aniline 
• 25199-84-2 4-(trifluoromethyl)quinolin-2(1H)-one 
• 328956-38-3 6-nitro-4-trifluoromethylquinolin-2(1H)-one 

Downstream Products

• 328947-81-5 6-Dimethylamino-4-trifluoromethyl-2(1H)-quinolinone 

Relevant academic research and scientific papers

Novel selective androgen receptor modulators: SAR studies on 6-bisalkylamino-2-quinolinones

A series of selective androgen receptor modulators (SARMs) with a wide spectrum of receptor modulating activities was developed based on optimization of the 4-substituted 6-bisalkylamino-2-quinolinones (3). Significance of the trifluoromethyl group on the side chains and its interactions with amino acid residues within the androgen receptor (AR) ligand binding domain are discussed. A representative analog (9) was tested orally in a rodent model of hypogonadism and demonstrated desirable tissue selectivity.

Discovery of 6-N,N-Bis(2,2,2-trifluoroethyl)amino-4- trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator

The androgen receptor is a member of the extended family of nuclear receptors and is widely distributed throughout the body. Androgen therapy is used to compensate for low levels of the natural hormones testosterone (T) and dihydrotestosterone and consist

Bicyclic androgen and progesterone receptor modulator compounds and methods

The present invention is directed to compounds, pharmaceutical compositions, and methods for modulating processes mediated by AR and PR. More particularly, the invention relates to nonsteroidal compounds and compositions that are high affinity, high specificity agonists, partial agonists (i.e., partial activators and/or tissue-specific activators) and antagonists for AR and PR. Also provided are methods of making such compounds and pharmaceutical compositions, as well as critical intermediates used in their synthesis.