169749-89-7Relevant academic research and scientific papers
Preparation and antibacterial activity of pyridopyridone analogs: C-1 modifications
Klein, Larry L.,DeGoey, David A.,Thomas, Sheela A.,Yeung, Clinton M.,Leone, Christina L.,Grampovnik, David J.,Chu, Daniel T.,Lartey, Paul A.
, p. 1167 - 1170 (1997)
Variation of the C-1 position of the pyridopyridone antibacterials shows a sensitivity to both size and electronic character of the substituent.
8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4-hydroxy-quinolizine-3-carboxylate and synthetic method thereof
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, (2017/08/28)
The invention provides 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4-hydroxy-quinolizine-3-carboxylate and a synthetic method thereof. The synthetic method comprises the following steps: a compound 6 and tert-butyldimethylsilyl chloride react in a firs
8-chloro-1-cyclopropyl-7-fluorine-9-methyl-4-oxygen-4-hydrogen-quinolizine-3-carboxylic ester and preparation method thereof
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, (2017/04/28)
The invention provides a preparation method of 8-chloro-1-cyclopropyl-7-fluorine-9-methyl-4-oxygen-4-hydrogen-quinolizine-3-carboxylic ester. The preparation method comprises the following steps: step one, enabling 2, 5-difluoropyridine and chlorine supply compound to react in a non-protonic solvent, and obtaining 4-chloro-2, 5-difluoropyridine; step two, enabling 4-chloro-2, 5-difluoropyridine and methyl donor to react in a non-protonic solvent, and obtaining 4-chloro-2, 5-difluoro-3-methylpyridine; step three, enabling 4-chloro-2, 5-difluoro-3-methylpyridine and cyclopropyl acetonitrile to react under the effect of strong base, and obtaining 2-(4-chloro-5-fluorine-3-methylpyridine-2-base)-2-cyclopropylacetonitrile; step four, preparing 2-(4-chloro-5-fluorine-3-methylpyridine-2-base)-2-cyclopropyl acetaldehyde; step five, enabling 2-(4-chloro-5-fluorine-3-methylpyridine-2-base)-2-cyclopropyl acetaldehyde and malonic ester to react, and obtaining 8-chloro-1-cyclopropyl-7-fluorine-9-methyl-4-oxygen-4-hydrogen-quinolizine-3-carboxylic ester. The method can reduce the synthesis steps of final products, and reduce the preparation cost.
ANTIMICROBIAL QUINOLONES, THEIR COMPOSITIONS AND USES
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Page 87; 90, (2010/02/06)
Compounds of the following formula (I) are effective antimicrobial agents.
Pyridone antibiotic with improved safety profile
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, (2008/06/13)
Antibacterial compounds having the formula STR1 and the pharmaceutically acceptable salts, esters and amides thereof, as well as pharmaceutical compositions containing such compounds and the use of the same in the treatment of bacterial infections.
Practical synthesis of 2-pyridone core: Ethyl 8-chloro-1-cyclopropyl-7- fluoro-9-methyl-4-oxo-4H-quinolizinone-3-carboxylate
Li, Qun,Sowin, Thomas,Claiborne, Akiyo,Lijewski, Linda,Zhang, Xiaolin,Raye, Kathleen,Mazdiyasni, Hormoz,Arnold, William,Melcher, Laura M.,Wang, Weibo,Hasvold, Lisa,Fung, Anthony,Chu, Daniel T. W.,Plattner
, p. 1345 - 1353 (2007/10/03)
A practical synthesis of the fluoropyridone core (2), an important intermediate to ABT-719 and other 2-pyridones, from the commercially available 3-chlorotetrafluoropyridine in 10 to 11 linear transformations with 10-26% overall yield is described.
Process for preparation of 4H-4-oxo-quinolizine-3-carboxylic acid
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, (2008/06/13)
A process for the preparation of a compound having the formula: STR1 wherein R1, R2, R3, R4, and R5 are defined, from an enamine by chain expansion and ring closure followed by additional derivatization, treatment with a 3-alkoxyl-acryloyl compound, another ring closure, and converting a hydroxyl group to a leaving group.
Synthesis and structure-activity relationships of 2-pyridones: A novel series of potent DNA gyrase inhibitors as antibacterial agents
Li, Qun,Chu, Daniel T. W.,Claiborne, Akiyo,Cooper, Curt S.,Lee, Cheuk M.,Raye, Kathleen,Berst, Kristine B.,Donner, Pamela,Wang, Weibo,Hasvold, Lisa,Fung, Anthony,Ma, Zhenkun,Tufano, Michael,Flamm, Robert,Shen, Linus L.,Baranowski, John,Nilius, Angela,Alder, Jeff,Meulbroek, Jonathan,Marsh, Kennan,Crowell, DeAnne,Hui, Yuhua,Seif, Louis,Melcher, Laura M.,Henry, Rodger,Spanton, Steven,Faghih, Ramin,Klein, Larry L.,Tanaka, S. Ken,Plattner, Jacob J.
, p. 3070 - 3088 (2007/10/03)
Two novel series of 2-pyridones were synthesized by transposition of the nitrogen of 4-quinolones to the bridgehead position. This subtle interchange of the nitrogen atom with a carbon atom yielded two novel heterocyclic nuclei, pyrido[1,2-a]pyrimidine and quinolizine, which had not previously been evaluated as antibacterial agents and were found to be potent inhibitors of DNA gyrase. Quinolizines with a methyl group at the 9-position such as (S)-45a (ABT-719) demonstrate exceptional broad spectrum antibacterial activity. Most notably, they are active against resistant bacteria such as methicillin-resistant Staphylococcus aureus, vancomycin-resistant strains of enterococci, and ciprofloxacin-resistant organisms. In addition, 2-pyridones also possess favorable physiochemical and pharmacokinetic properties. These 2-pyridones were synthesized from the commercially available starting materials by 10-17 linear transformations. The structure of an adduct yielded by this sequence, (S)-45a (ABT-719), was determined by X-ray crystallographic analysis.
Quinolizinone type compounds
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, (2008/06/13)
Antibacterial compounds having the formula STR1 and the pharmaceutically acceptable salts, esters and amides thereof, preferred examples of which include those compounds wherein A is =CR6 --; R1 is cycloalkyl of from three to eight carbon atoms or substituted phenyl; R2 is selected from the group consisting of STR2 R3 is halogen; R4 is hydrogen, loweralkyl, a pharmaceutically acceptable cation, or a prodrug ester group; R5 is hydrogen, loweralkyl, halo(loweralkyl), or --NR13 R14 ; and R6 is halogen, loweralkyl, halo(loweralkyl), hydroxy-substituted loweralkyl, loweralkoxy(loweralkyl), loweralkoxy, or amino(loweralkyl), as well as pharmaceutical compositions containing such compounds and the use of the same in the treatment of bacterial infections.
