JPS57144264A - 6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid derivative - Google Patents
6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid derivativeInfo
- Publication number
- JPS57144264A JPS57144264A JP3084081A JP3084081A JPS57144264A JP S57144264 A JPS57144264 A JP S57144264A JP 3084081 A JP3084081 A JP 3084081A JP 3084081 A JP3084081 A JP 3084081A JP S57144264 A JPS57144264 A JP S57144264A
- Authority
- JP
- Japan
- Prior art keywords
- oxocinnoline
- dihydro
- fluoro
- carboxylic acid
- formula
- 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
- WGHGCTAGCWPEKM-UHFFFAOYSA-N 6-fluoro-4-oxo-1h-cinnoline-3-carboxylic acid Chemical class C1=C(F)C=C2C(=O)C(C(=O)O)=NNC2=C1 WGHGCTAGCWPEKM-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 241000894006 Bacteria Species 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical class NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 abstract 1
- -1 7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid Chemical compound 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
NEW MATERIAL:The 6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid derivative of formulaI(R1 is lower alkyl; R2 is halogen atom or group of formula II; R is H or lower alkyl) and its salt.
EXAMPLE: 7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid.
USE: It has strong antitiotic activity against bacteria, especially Gram-negative bacteria, and is useful as a remedy for bacterial infectious diseases, or its intermediate.
PROCESS: The compound of formulaIis prepared by (1) converting the 4-fluoroaniline derivative of formula III used as the starting material to the diazonium salt, (2) reacting the salt with diethyl malonate, (3) carrying out the N-alkylation of the reaction product to obtain the compound of formula IV, (4) reacting the product in polyphosphoric acid ethyl ester, and (5) hydrolyzing the resultant compound of formula V.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3084081A JPS57144264A (en) | 1981-03-03 | 1981-03-03 | 6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3084081A JPS57144264A (en) | 1981-03-03 | 1981-03-03 | 6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS57144264A true JPS57144264A (en) | 1982-09-06 |
Family
ID=12314888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3084081A Pending JPS57144264A (en) | 1981-03-03 | 1981-03-03 | 6-fluoro-1,4-dihydro-4-oxocinnoline-3-carboxylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57144264A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4756740A (en) * | 1983-09-14 | 1988-07-12 | Lafarge Coppee | Pollen suppressant comprising a fused pyridazine |
| US7056917B2 (en) | 2001-04-26 | 2006-06-06 | Daiichi Pharmaceutical Co., Ltd. | Drug efflux pump inhibitor |
-
1981
- 1981-03-03 JP JP3084081A patent/JPS57144264A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4756740A (en) * | 1983-09-14 | 1988-07-12 | Lafarge Coppee | Pollen suppressant comprising a fused pyridazine |
| US7056917B2 (en) | 2001-04-26 | 2006-06-06 | Daiichi Pharmaceutical Co., Ltd. | Drug efflux pump inhibitor |
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