497854-88-3

Upstream product

• 5315-25-3 2-bromo-6-methylpyridine 
• 931-19-1 2-methylpyridine N-oxide 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 497854-87-2 (4-fluorophenyl)(6-methylpyridin-2-yl)acetonitrile 

Downstream Products

• 497849-93-1 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(6-methyl-1-oxidopyridin-2-yl)methyl]phenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497849-92-0 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(6-methylpyridin-2-yl)methyl]phenyl}-1-(trifluoroacetyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497849-94-2 7-[4-(2-butoxyethoxy)phenyl]-N-{4-[hydroxy(6-methyl-1-oxidopyridin-2-yl)methyl]phenyl}-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 497851-73-7 (4-aminophenyl)(6-methylpyridin-2-yl)methanol 

Relevant academic research and scientific papers

Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies

Herein, we report an original one-step, simple, room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The 18O-labeling experiment suggested that water is a source of oxygen in the acylated product, and head space GC-MS experiment shows the C-C cleavage occurs via release as CO2.

Orally active CCR5 antagonists as anti-HIV-1 agents 2: Synthesis and biological activities of anilide derivatives containing a pyridine N-oxide moiety

In order to develop orally active CCR5 antagonists, we investigated 1-benzoxepine derivatives containing new polar substituents, such as phosphonate, phosphine oxide or pyridine N-oxide moieties, as replacements for the previoiusly reported quaternary ammonium moiety. Among these compounds, the 2-(α-hydroxybenzyl)pyridine N-oxide 5e exhibited moderate CCR5 antagonistic activity and had an acceptable pharmacokinetic profile in rats. Subsequent chemical modification was performed and compound (S)-5f possessing the (S)-configuration hydroxy group was found to be more active than the (R)-isomer. Replacement of the 1-benzoxepine ring with a 4-methylphenyl group by a 1-benzazepine ring with a 4-[2-(butoxy)ethoxy]phenyl group enhanced the activity in the binding assay. In addition, introduction of a 3-trifluoromethyl group on the phenyl group of the anilide moiety led to greatly increased activity in the HIV-1 envelope-mediated membrane fusion assay. In particular, compound (S)-5s showed the most potent CCR5 antagonistic activity (IC 50=7.2 nM) and inhibitory effect (IC50=5.4 nM) in the fusion assay, together with good pharmacokinetic properties in rats.

BENZAZEPINE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE

The present invention provides a novel benzazepine derivative represented by formula : wherein, R1 is a 5- or 6-membered aromatic ring, R2 is lower alkyl group, etc., Y is an optionally substituted imino group, ring A and ring B are independently an optionally substituted aromatic ring, W is formula -W1-X2-W2- (W1 and W2 are independently S(O)m1 (m1 is 0, 1 or 2), etc., and X2 is an optionally substituted alkylene groupetc. ), a preparation method and use thereof.