- Synthesis of 4-halogenated 3-fluoro-6-methoxyquinolines: Key building blocks for the synthesis of antibiotics
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A practical and scalable 4-step route is presented for the synthesis of 4-bromo-3-fluoro-6-methoxyoquinoline and 3-fluoro-4-iodo-6-methoxyoquinoline from readily available 2,4-dichloro-3-fluoroquinoline with an overall yield of 81-85%. Halogenated quinoline building blocks have found much use in antimicrobial drug discovery, and the method reported here would be useful for the synthesis of these compounds.
- Flagstad, Thomas,Petersen, Mette T.,Hinnerfeldt, Daniel M.,Givskov, Michael,Nielsen, Thomas E.
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Read Online
- Novel 3-fluoro-6-methoxyquinoline derivatives as inhibitors of bacterial DNA gyrase and topoisomerase IV
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Novel (non-fluoroquinolone) inhibitors of bacterial type II topoisomerases (NBTIs) are an emerging class of antibacterial agents. We report an optimized series of cyclobutylaryl-substituted NBTIs. Compound 14 demonstrated excellent activity both in vitro (S. aureus MIC90?=?0.125?μg/mL) and in vivo (systemic and tissue infections). Enhanced inhibition of Topoisomerase IV correlated with improved activity in S. aureus strains with mutations conferring resistance to NBTIs. Compound 14 also displayed an improved hERG IC50 of 85.9?μM and a favorable profile in the anesthetized guinea pig model.
- Mitton-Fry, Mark J.,Brickner, Steven J.,Hamel, Judith C.,Barham, Rose,Brennan, Lori,Casavant, Jeffrey M.,Ding, Xiaoyuan,Finegan, Steven,Hardink, Joel,Hoang, Thuy,Huband, Michael D.,Maloney, Meghan,Marfat, Anthony,McCurdy, Sandra P.,McLeod, Dale,Subramanyam, Chakrapani,Plotkin, Michael,Reilly, Usa,Schafer, John,Stone, Gregory G.,Uccello, Daniel P.,Wisialowski, Todd,Yoon, Kwansik,Zaniewski, Richard,Zook, Christopher
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Read Online
- Initial Route Scouting and Final Process Development for the Multi-Kg Production of 3-Fluoro-6-methoxyquinoline from p-Anisidine and 2-Fluoromalonic Acid
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A scalable route to 3-fluoro-6-methoxyquinoline needed to be developed as multi-kg amounts of this heterocycle were required. Initial route development focused on the formation of the key C-F bond via a Balz-Schiemann reaction or electrophilic fluorinatio
- Sch?fer, Gabriel,Fleischer, Tony,Blumer, Nicole,Udry, Megan,Reber, Stefan,Stansfield, Ian,Liu, Yuanhua,Li, Yan,Li, Pixu
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p. 347 - 357
(2022/02/01)
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- Hepatitis C virus inhibitors
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Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 599; 600
(2017/01/23)
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- Hepatitis C Virus Inhibitors
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Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column
(2013/05/21)
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- 4-(1-AMINO-ETHYL)-CYCLOHEXYLAMINE DERIVATIVES
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The invention relates to compounds of formula (I) wherein R0 represents H or OH; R1 represents alkoxy; U and W represent N, V represents CH and R2 represents H or F, or U and V represent CH, W represents N and R2 /su
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Page/Page column 33
(2010/03/02)
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- A facile two-step synthesis of 3-fluoro-6-methoxyquinoline
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A facile two-step synthesis of 3-fluoro-6-methoxyquinoline is described. p-Anisidine was heated at reflux with 2-fluoromalonic acid in the presence of phosphorus oxychloride to produce 2,4-dichloro-3-fluoro-6-methoxyquinoline. This was followed by hydrogenolysis to produce 3-fluoro-6-methoxyquinoline.
- Li, Bryan,Zhang, Zhijun,Mangano, Michael
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p. 1273 - 1275
(2013/01/03)
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- SUBSTITUTED HETEROCYCLIC DERIVATIVES AND THEIR PHARMACEUTICAL USE AND COMPOSITIONS
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Compounds of the general Formula I, wherein X1, X2, X3, X4, X5, X6, X7, R1, R2, R4, R5, R6, R7, R8, R9, R10, Y1, n, m, p and q are defined as above, their preparation and their use as antimicrobial agents.
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Page/Page column 24
(2008/12/08)
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- Method For Preparation Of A Fluoroaromatic Compound From An Aminoaromatic Compound
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The invention relates to a method for preparation of fluorinated aromatic compounds from the corresponding amines by replacement of the amino group with a fluorine atom. The method of preparation of a fluoroaromatic compound from an aromatic compound with at least one amino group on the aromatic ring is characterized by the reaction of said aromatic amine compound with a nitrosating agent in the presence of a source of boron trifluoride in an organic medium, and carrying out a thermal treatment of the reaction medium comprising the diazonium salt thus obtained to give the fluoroaromatic compound directly by decomposition of the diazonium salt without intermediate isolation thereof.
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Page/Page column 9
(2008/06/13)
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- ACETAMIDE COMPOUNDS AS FUNGICIDES
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Compounds of the general formula (I); wherein the substituents are as defined in claim 1, are useful as fungicides.
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Page/Page column 90
(2010/11/08)
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- Novel process for preparing 3-fluoroquinolines
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The invention relates to a novel preparation of 3-fluoroquinolines of formula (I) in which R1, R2, R3 and R4 represent: a) a fluorine; b) an alkyl optionally substituted with one to three fluorines, with OR
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Page/Page column 4
(2008/06/13)
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- Heterocyclylalkylpiperidine derivatives, their preparation and compositions containing them
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Heterocyclylalkylpiperidine derivatives of general formula (I) in their enantiomeric or diastereoisomeric forms or mixtures of these forms, and/or, where appropriate, in their syn or anti form or a mixture thereof, as well as any salt thereof.
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