856867-59-9

Upstream product

• 380380-60-9 2-(1,2,3,4-tetrazol-5-yl)-5-bromopyridine 
• 380380-64-3 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine 
• 97483-77-7 2-Cyano-5-bromopyridine 
• 624-28-2 2,5-dibromopyridine 
• 856866-72-3 (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 700370-32-7 (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one 
• 1293990-05-2 (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(azidomethyl)oxazolidin-2-one 
• 1293990-06-3 (S)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(aminomethyl)oxazolidin-2-one 
• 1293990-07-4 (S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)-2-methoxyacetamide 
• 1293990-08-5 (S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)furan-2-carboxamide 
• 1293990-09-6 (S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)thiopene-2-carboxamide 
• 1293990-10-9 (S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 
• 1293990-11-0 (S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)-2-hydroxyacetamide 

Relevant academic research and scientific papers

Discovery of torezolid as a novel 5-hydroxymethyl-oxazolidinone antibacterial agent

A series of novel substituted pyridyl phenyl oxazolidinone analogues were synthesized and their structure-activity relationship (SAR) was investigated based on in vitro and in vivo antibacterial activities. The minimum inhibitory concentrations (MICs) of the synthesized compounds against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) ranged from 0.12 to 2.0 μg/mL, and against Haemophilus influenzae (Hi) from 2.0 to 8.0 μg/mL. Compared to linezolid, only four compounds (11, 12, 21 and 29) showed higher in vitro antibacterial activities and better in vivo protective effects in mice. To improve the aqueous solubility, various prodrugs of compound 11 (DA-7157), which exerted a potency that was enhanced by 2-8-fold compared to that of linezolid, were synthesized. Among the prodrugs, the phosphate compound 42 exhibited excellent aqueous solubility (>50 mg/mL in DW) and good pharmacokinetic profiles, along with better in vivo efficacy than linezolid. This compound 42 is currently undergoing clinical trials with the brand name Torezolid.

NOVEL OXAZOLIDINONE DERIVATIVES

The present invention relates to novel derivatives of oxazolidinone, a method thereof and pharmaceutical compositions comprising the derivatives for use in an antibiotic. The oxazolidinone derivatives of the present invention show inhibitory activity against a broad spectrum of bacteria and lower toxicity. The prodrugs, prepared by reacting the compound having hydroxyl group with amino acid or phosphate, have an excellent efficiency on solubility thereof against water. Further, the derivatives of the present invention may exert potent antibacterial activity versus various human and animal pathogens, including Gram-positive bacteria such as Staphylococi, Enterococci and Streptococi, anaerobic microorganisms such as Bacteroides and Clostridia, and acid-resistant microorganisms such as Mycobacterium tuberculosis and Mycobacterium avium. Accordingly, the compositions comprising the oxazolidinone are used in an antibiotic.