JPS54112877A - Preparation of 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid derivatives - Google Patents
Preparation of 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid derivativesInfo
- Publication number
- JPS54112877A JPS54112877A JP1879478A JP1879478A JPS54112877A JP S54112877 A JPS54112877 A JP S54112877A JP 1879478 A JP1879478 A JP 1879478A JP 1879478 A JP1879478 A JP 1879478A JP S54112877 A JPS54112877 A JP S54112877A
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- carboxylic acid
- pyridine carboxylic
- halide
- dihydro
- 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.)
- Pending
Links
- -1 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid Chemical class 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 3
- RNHQLAFZMYJXQO-UHFFFAOYSA-N 4-oxo-3h-pyridine-3-carboxylic acid Chemical class OC(=O)C1C=NC=CC1=O RNHQLAFZMYJXQO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical group 0.000 abstract 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 abstract 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 235000003270 potassium fluoride Nutrition 0.000 abstract 1
- 239000011698 potassium fluoride Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
Abstract
PURPOSE: To prepare the title compound useful as an antibiotic, etc. in high purity and in a short time, by alkyating 4-oxo-3-pyridine carboxylic acid derivative in the presence of a specific compound such as N-methylpyridinium halide, etc., followed by hydrolyzing the product.
CONSTITUTION: A 4-oxo-3-pyridine carboxylic acid derivative I (R1 is lower alkyl, H; X, Y, Z are C, N; A, B are H, halogen, etc.; A and B may together form a condensed rign) is made to react with an alkylating agent such as methyl iodide, etc. in the presence of a quaternary amine base such as tetraalkylammonium halide, N-methylpyridinium halide, etc., or potassium fluoride. The objective compound II (R2 is hydroxy lower alkyl, etc.) is obtained by the hydrolysis of the above reaction product. The amount of the quaternary amine or potassium halide is ≥1 wt% based on the compound I.
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1879478A JPS54112877A (en) | 1978-02-20 | 1978-02-20 | Preparation of 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1879478A JPS54112877A (en) | 1978-02-20 | 1978-02-20 | Preparation of 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS54112877A true JPS54112877A (en) | 1979-09-04 |
Family
ID=11981494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1879478A Pending JPS54112877A (en) | 1978-02-20 | 1978-02-20 | Preparation of 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54112877A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3031767A1 (en) | 1979-08-22 | 1981-03-26 | Kyorin Seiyaku K.K., Tokio/Tokyo | CHINOLINE CARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| JPS5653656A (en) * | 1979-10-05 | 1981-05-13 | Tanabe Seiyaku Co Ltd | Quinoline derivative and its preparation |
| JPS58105965A (en) * | 1981-12-15 | 1983-06-24 | Nippon Shinyaku Co Ltd | Substituted quinolinecarboxylic acid derivative |
| JPH01156961A (en) * | 1987-04-30 | 1989-06-20 | Dainippon Pharmaceut Co Ltd | Novel pyridonecarboxylic acid derivative, ester and salt thereof |
| US7470706B2 (en) * | 2004-01-31 | 2008-12-30 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl-substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| US8076120B2 (en) | 2000-11-20 | 2011-12-13 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| WO2019138084A1 (en) * | 2018-01-11 | 2019-07-18 | Institut Pasteur | Phenanthrolinone derivatives for use in the treatment of bacterial infections |
-
1978
- 1978-02-20 JP JP1879478A patent/JPS54112877A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3031767A1 (en) | 1979-08-22 | 1981-03-26 | Kyorin Seiyaku K.K., Tokio/Tokyo | CHINOLINE CARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| JPS5653656A (en) * | 1979-10-05 | 1981-05-13 | Tanabe Seiyaku Co Ltd | Quinoline derivative and its preparation |
| JPS6324991B2 (en) * | 1979-10-05 | 1988-05-23 | Tanabe Seiyaku Co | |
| JPS58105965A (en) * | 1981-12-15 | 1983-06-24 | Nippon Shinyaku Co Ltd | Substituted quinolinecarboxylic acid derivative |
| JPH0312061B2 (en) * | 1981-12-15 | 1991-02-19 | Nippon Shinyaku Co Ltd | |
| JPH01156961A (en) * | 1987-04-30 | 1989-06-20 | Dainippon Pharmaceut Co Ltd | Novel pyridonecarboxylic acid derivative, ester and salt thereof |
| US8501455B2 (en) | 2000-11-20 | 2013-08-06 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US8076120B2 (en) | 2000-11-20 | 2011-12-13 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US8198066B2 (en) | 2000-11-20 | 2012-06-12 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US8759059B2 (en) | 2000-11-20 | 2014-06-24 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US8822197B2 (en) | 2000-11-20 | 2014-09-02 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US8999700B2 (en) | 2000-11-20 | 2015-04-07 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US9340803B2 (en) | 2000-11-20 | 2016-05-17 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US7470706B2 (en) * | 2004-01-31 | 2008-12-30 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl-substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| WO2019138084A1 (en) * | 2018-01-11 | 2019-07-18 | Institut Pasteur | Phenanthrolinone derivatives for use in the treatment of bacterial infections |
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