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.Info
- 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
- Authority
- 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
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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.
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 |
Family
ID=8276236
Family Applications (1)
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)
Country | Link |
---|---|
ES (1) | ES2049631B1 (en) |
Citations (5)
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. |
-
1992
- 1992-02-28 ES ES9200447A patent/ES2049631B1/en not_active Expired - Fee Related
Patent Citations (5)
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 |