ES2049631A1 - Substd. piperazinyl quinolone carboxylic acid deriv. prepn. - involves conversion of 3-chloro-4-fluoro:aniline to acetanilide, redn. conversion to formanilide, ring closure with ethoxy-malonyl chloride, etc. - Google Patents

Substd. piperazinyl quinolone carboxylic acid deriv. prepn. - involves conversion of 3-chloro-4-fluoro:aniline to acetanilide, redn. conversion to formanilide, ring closure with ethoxy-malonyl chloride, etc.

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Publication number
ES2049631A1
ES2049631A1 ES9200447A ES9200447A ES2049631A1 ES 2049631 A1 ES2049631 A1 ES 2049631A1 ES 9200447 A ES9200447 A ES 9200447A ES 9200447 A ES9200447 A ES 9200447A ES 2049631 A1 ES2049631 A1 ES 2049631A1
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ES
Spain
Prior art keywords
fluoro
chloro
ethyl
carboxylic acid
aniline
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
ES9200447A
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Spanish (es)
Other versions
ES2049631B1 (en
Inventor
Gonzalez Ramos
Lopez Vaquero
Robisco Novella
Gomez Alvarez-Builla
Navio Garcia
Arinero Calatayud
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BYK LEO LABORATORIO FARMACEUTICO, S.L.
Original Assignee
ELMUQUIMICA FARM SL
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Priority to ES9200447A priority Critical patent/ES2049631B1/en
Publication of ES2049631A1 publication Critical patent/ES2049631A1/en
Application granted granted Critical
Publication of ES2049631B1 publication Critical patent/ES2049631B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Abstract

New procedure for obtaining 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1- piperazinyl)-3-quinoline carboxylic acid, verified in 5 steps:Step 1: Acetic anhydride reacts with 3-chloro-4-fluoro aniline to obtain 3-chloro-4-fluoro acetanilide.Step 2: The compound obtained is reduced with diborane to produce N-ethyl-3-chloro-4-fluoro aniline.Step 3: The aniline obtained reacts with formic acid to obtain N-ethyl-3-chloro-4-fluoro formanilide.Step 4: The substance obtained above reacts with phosphorus oxychloride and ethoxy malonyl chloride, producing, once the blend is basified, 1-ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid.Step 5: The acid obtained reacts with 1-methylpiperazine to obtain 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-quinoline carboxylic acid, the subject of this invention.Applications: Our process is designed to ensure a minimal amount of toxic reagents and residues. It uses reagents which present few problems in large-scale use, with appreciable advantages in industrial production.1-ethyl 6-fluoro 1,4-dihydro 4-oxo 7-(4-methyl 1-piperazinyl) quinoline 3-carboxylic acid is made by (1) reacting acetic anhydride with 3-chloro-4-fluoro aniline (2) reducing the acetanilide with diborane to give N-ethyl 3-chloro 4-fluoro aniline (3 reacting with formic acid to give the formanilide (4) reacting with POCl3 and ethoxy-malonyl chloride and basifying to give 1-ethyl 7-chloro 6-fluoro 1,4-dihydro 4-oxo quinoline 3-carboxylic acid and (5) reacting with 1-methyl piperazine to give the required prod.
ES9200447A 1992-02-28 1992-02-28 NEW PROCEDURE FOR OBTAINING THE ACID 1-ETIL-6-FLUORO-1,4-DIHIDRO-4-OXO-7- (4-METHYL-1-PIPERACINIL) -3-QUINOLIN CARBOXILICO. Expired - Fee Related ES2049631B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES9200447A ES2049631B1 (en) 1992-02-28 1992-02-28 NEW PROCEDURE FOR OBTAINING THE ACID 1-ETIL-6-FLUORO-1,4-DIHIDRO-4-OXO-7- (4-METHYL-1-PIPERACINIL) -3-QUINOLIN CARBOXILICO.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9200447A ES2049631B1 (en) 1992-02-28 1992-02-28 NEW PROCEDURE FOR OBTAINING THE ACID 1-ETIL-6-FLUORO-1,4-DIHIDRO-4-OXO-7- (4-METHYL-1-PIPERACINIL) -3-QUINOLIN CARBOXILICO.

Publications (2)

Publication Number Publication Date
ES2049631A1 true ES2049631A1 (en) 1994-04-16
ES2049631B1 ES2049631B1 (en) 1994-12-16

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Application Number Title Priority Date Filing Date
ES9200447A Expired - Fee Related ES2049631B1 (en) 1992-02-28 1992-02-28 NEW PROCEDURE FOR OBTAINING THE ACID 1-ETIL-6-FLUORO-1,4-DIHIDRO-4-OXO-7- (4-METHYL-1-PIPERACINIL) -3-QUINOLIN CARBOXILICO.

Country Status (1)

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ES (1) ES2049631B1 (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2843066A1 (en) * 1978-04-19 1979-11-08 Kyorin Seiyaku Kk Substd. 7-piperazinyl-4-oxo-1,4-di:hydro:quinoline-3-carboxylic acid - used as antibacterial against Gram positive and negative bacteria esp. Pseudomonas aeruginosa
US4292317A (en) * 1977-09-20 1981-09-29 Laboratorie Roger Bellon 1,4-Dihydro-quinoline-3-carboxylic acid derivatives, process for their preparation and compositions containing them
ES8600747A1 (en) * 1985-01-31 1985-11-01 Andreu Sa Dr Piperazinyl quinoline carboxylic acid derivs.
EP0220523A2 (en) * 1985-10-01 1987-05-06 Kanebo, Ltd. Novel quinolinecarboxylic acid compounds, processes for preparing them, pharmaceutical composition and use
ES2010135A6 (en) * 1989-02-10 1989-10-16 Union Quimico Farma Norfloxacin bactericide prepn.

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4292317A (en) * 1977-09-20 1981-09-29 Laboratorie Roger Bellon 1,4-Dihydro-quinoline-3-carboxylic acid derivatives, process for their preparation and compositions containing them
DE2843066A1 (en) * 1978-04-19 1979-11-08 Kyorin Seiyaku Kk Substd. 7-piperazinyl-4-oxo-1,4-di:hydro:quinoline-3-carboxylic acid - used as antibacterial against Gram positive and negative bacteria esp. Pseudomonas aeruginosa
ES8600747A1 (en) * 1985-01-31 1985-11-01 Andreu Sa Dr Piperazinyl quinoline carboxylic acid derivs.
EP0220523A2 (en) * 1985-10-01 1987-05-06 Kanebo, Ltd. Novel quinolinecarboxylic acid compounds, processes for preparing them, pharmaceutical composition and use
ES2010135A6 (en) * 1989-02-10 1989-10-16 Union Quimico Farma Norfloxacin bactericide prepn.

Also Published As

Publication number Publication date
ES2049631B1 (en) 1994-12-16

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Legal Events

Date Code Title Description
PC2A Transfer of patent

Owner name: BYK LEO LABORATORIO FARMACEUTICO, S.L.

FD1A Patent lapsed

Effective date: 20040916