103995-33-1

Usage

Uses

Used in Pharmaceutical Industry:
Levofloxacin Tetrafluoro Impurity 2 is used as a quality control parameter for ensuring the safety and effectiveness of levofloxacin. Monitoring and controlling the presence of this impurity in the final product is crucial for maintaining product quality and regulatory compliance.
Used in Research and Development:
Levofloxacin Tetrafluoro Impurity 2 is used as a subject of study in research to understand its potential effects on the efficacy and safety of levofloxacin. This knowledge can help in the development of improved manufacturing processes and quality control measures to minimize the presence of impurities in the final product.

Upstream product

• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 
• 109-94-4 formic acid ethyl ester 
• 1020966-22-6 ethyl 2,3,4,5-tetrafluorobenzoyl acetate 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 448210-34-2 3-[N'-(3-nitro-benzoyl)-hydrazino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester 
• 476005-99-9 6,7,8-trifluoro-1-[(4-methoxy-benzimidoyl)-amino]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 352213-95-7 1-[(1-ethyl-6-fluoro-4-oxo-7-thiomorpholin-4-yl-1,4-dihydro-quinoline-3-carbonyl)-amino]-6,7,8-trifluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 516479-95-1 1-[(1-ethyl-6-fluoro-7-morpholin-4-yl-4-oxo-1,4-dihydro-quinoline-3-carbonyl)-amino]-6,7,8-trifluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 103994-84-9 ethyl 6,7,8-trifluoro-1-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 1041438-68-9 ethyl 1-(4-cyano-2,3,5,6-tetrafluorophenyl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 

Relevant academic research and scientific papers

Novel ofloxacin derivatives: Synthesis, antimycobacterial and toxicological evaluation

Thirty novel 9-fluoro-2,3-dihydro-8,10-(mono/di-sub)-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acids were synthesized from 2,3,4,5-tetrafluoro benzoic acid and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from mycobacteria. Among the synthesized compounds, 10-[2-carboxy-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid was found to be the most active compound in vitro with MIC99 of 0.19 μM and 0.09 μM against MTB and MTR-TB, respectively. In the in vivo animal model also the same compound decreased the bacterial load in lung and spleen tissues with 1.91 and 2.91 - log 10 protections, respectively, at the dose of 50 mg/kg body weight. Compound 10-[(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid was found to be the most active in the inhibition of the supercoiling activity of DNA gyrase with an IC50 of 10.0 μg/mL. The results demonstrate the potential and importance of developing new oxazino quinolone derivatives against mycobacterial infections.

Inhibition of the signal transducer and activator of transcription-3 (STAT3) signaling pathway by 4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid esters

The JAK-STAT3 pathway regulates genes that are important in cell proliferation and thus is a promising target for cancer therapy. A high-throughput screening (HTS) campaign using an Apo-ONE Homogenous Caspase 3/7 assay in U266 cells identified 4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 4 as a potential STAT3 pathway inhibitor. Optimization of this HTS hit led to the identification of the 7-cyano analogue 8, which inhibited STAT3-Y705 phosphorylation with an EC50 of 170 nM. Compound 8 also inhibited cytokine induced JAK activation but did not inhibit BCR-ABL activated STAT5 phosphorylation in K562 cells.

AN IMPROVED PROCESS FOR THE PREPARATION OF LEVOFLOXACIN HEMIHYDRATE

The present invention relates to an improved process for preparation of Levofloxacin hemihydrate having single individual impurity not more than 0.1% and free from particulate matter and from the other enantiomer (R-form) which comprises dissolving levofloxacin technical grade in aqueous alkaline solution, treating the resulting solution with activated carbon at room temperature, removing the undissolved particulate matter filtration, bringing the pH of the aqueous alkaline levofloxacin solution to neutral using dilute mineral acid, removing the precipitated particulate matter by filtration, acidifying the resulting solution, treating the acidified solution with activated carbon at room temperature, filtering the undissolved particulate matter by filtration, neutralizing the acidic solution, filtering again to remove any particulate matter present and, extracting the resulting product with chlorinated solvent and concentrating under vacuum using aqueous tetrahydrofuran or in admixture with other organic solvents to get highly pure levofloxacin hemihydrate having single individual impurity is less than 0.1% and fee from particulate matter and from the other enantiomer (R-form).

Novel benzothiazole compounds and methods of use thereof

The present invention relates to methods of preparing compounds having formula (1), (2), (5), and ((6A)-(6D)) comprising contacting the corresponding ester, an amine with formula NHR1R2, and a Lewis acid having formula MLn, wherein L is a halogen atom or an organic radical, n is 3-5, and M is a group III elemental atom, a group IV elemental atom, As, Sb, V or Fe, wherein A, B, V, X, Z, W, R1, R2, R5, Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are substituents. Z4, Z5, Z6, Z7, and Z8 are substituents.

Antibacterial 1,7-diamino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

Antibacterially effective 1,7-diamino-1,4-dihydro-4-oxo-3-(aza)quinolinecarboxylic acids of the formula STR1 in which A is nitrogen or C--R1, R1 is nitro or halogen, R2 and R3 each independently is C1

Chiral DNA gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-py ido[1,2,3,-de]-1,4-benzoxazine-6-carboxylic acid (ofloxacin)

A short and efficient synthesis, starting with (R)- and (S)-alaninol, of the two optical antipodes of the quinolone antimicrobial agent ofloxacin has been devised. Testing in vitro of the products against a range of bacteria and in an assay system incorporating purified DNA gyrase from different bacterial species demonstrates that the S-(-) enantiomer is substantially the more active.

Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds and compositions thereof

Novel 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds of the formula: STR1 wherein R is hydrogen atom or fluorine atom, R° is hydroxy, fluorine atom or an alkanoyloxy having 1 to 6 carbon atoms, and X1 is hydrogen atom or fluorine atom, and a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.

7-(3-aryl-1-piperazinyl)- and 7-(3-cyclohexyl-1-piperazinyl)-3-quinolonecarboxylic acid antibacterials

Novel 1-cyclopropyl-4-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid antibacterials of the formula STR1 in which R1 is hydrogen, alkyl with 1 to 4 carbon atoms and optionally substituted by hydroxyl, methoxy, amino, dimethylamino, halogen, cyano or alkoxycarbonyl having 1 or 2 carbon atoms in the alkyl moiety, or is oxoalkyl having up to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms, R2 is phenyl or cyclohexyl optionally substituted up to three times by halogen, methyl, phenyl, cyano, hydroxyl, methoxy, benzyloxy, amino, methylamino, dimethylamino, piperidino or nitro, or is methylenedioxyphenyl, methylenedioxycyclohexyl, furyl, tetrahydrofuryl or thienyl, and X1 is hydrogen or fluorine, or pharmaceutically ultizable hydrates, acid addition salts, alkali metal salts or alkaline earth metal salts thereof.

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-quinolinecarboxylic acid antibacterial agents

Novel antibacterially active 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-quinolinecarboxylic acids of the formula STR1 in which R1 is hydrogen, methyl or ethyl, and R2 is hydrogen or fluorine, and pharmaceutically tolerable hydrates and salts thereof.