CA1077939A - Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its esters - Google Patents
Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its estersInfo
- Publication number
- CA1077939A CA1077939A CA272,396A CA272396A CA1077939A CA 1077939 A CA1077939 A CA 1077939A CA 272396 A CA272396 A CA 272396A CA 1077939 A CA1077939 A CA 1077939A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- acid
- oxo
- formula
- 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.)
- Expired
Links
- JYJKFMPCGBLLHN-UHFFFAOYSA-N 5-(difluoromethyl)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Chemical compound C1=C2C(=O)C(C(=O)O)=CN(C(F)F)C2=CC2=C1OCO2 JYJKFMPCGBLLHN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title description 8
- 230000000844 anti-bacterial effect Effects 0.000 title description 5
- 229940088710 antibiotic agent Drugs 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract description 4
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
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- 241000588724 Escherichia coli Species 0.000 description 15
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- 241000894006 Bacteria Species 0.000 description 4
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- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
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- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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- 231100000645 Reed–Muench method Toxicity 0.000 description 1
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- HTYIXCKSEQQCJO-UHFFFAOYSA-N phenaglycodol Chemical compound CC(C)(O)C(C)(O)C1=CC=C(Cl)C=C1 HTYIXCKSEQQCJO-UHFFFAOYSA-N 0.000 description 1
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- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66085276A | 1976-02-23 | 1976-02-23 | |
| US05/758,331 US4147788A (en) | 1976-02-23 | 1977-01-14 | Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077939A true CA1077939A (en) | 1980-05-20 |
Family
ID=27098199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,396A Expired CA1077939A (en) | 1976-02-23 | 1977-02-21 | Antibacterials: 1-difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its esters |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS52118496A (cs) |
| AR (1) | AR212613A1 (cs) |
| AU (1) | AU510359B2 (cs) |
| CA (1) | CA1077939A (cs) |
| CH (1) | CH631986A5 (cs) |
| DD (1) | DD129450A5 (cs) |
| DE (1) | DE2706781A1 (cs) |
| DK (1) | DK76077A (cs) |
| ES (2) | ES456162A1 (cs) |
| FI (1) | FI66175C (cs) |
| FR (2) | FR2341580A1 (cs) |
| GB (1) | GB1517674A (cs) |
| GR (1) | GR62469B (cs) |
| IE (1) | IE44701B1 (cs) |
| IL (1) | IL51518A (cs) |
| LU (1) | LU76818A1 (cs) |
| MX (1) | MX4877E (cs) |
| NL (1) | NL7701884A (cs) |
| NO (2) | NO147069C (cs) |
| PH (1) | PH13084A (cs) |
| PT (1) | PT66219B (cs) |
| SE (1) | SE434400B (cs) |
| SU (1) | SU626700A3 (cs) |
| YU (2) | YU49277A (cs) |
-
1977
- 1977-01-27 SE SE7700871A patent/SE434400B/xx unknown
- 1977-02-17 DE DE19772706781 patent/DE2706781A1/de not_active Withdrawn
- 1977-02-21 AU AU22488/77A patent/AU510359B2/en not_active Expired
- 1977-02-21 PT PT66219A patent/PT66219B/pt unknown
- 1977-02-21 CA CA272,396A patent/CA1077939A/en not_active Expired
- 1977-02-21 AR AR266624A patent/AR212613A1/es active
- 1977-02-22 SU SU772455503A patent/SU626700A3/ru active
- 1977-02-22 LU LU76818A patent/LU76818A1/xx unknown
- 1977-02-22 MX MX775452U patent/MX4877E/es unknown
- 1977-02-22 IL IL51518A patent/IL51518A/xx unknown
- 1977-02-22 FR FR7705060A patent/FR2341580A1/fr active Granted
- 1977-02-22 GR GR52825A patent/GR62469B/el unknown
- 1977-02-22 FI FI770567A patent/FI66175C/fi not_active IP Right Cessation
- 1977-02-22 GB GB7417/77A patent/GB1517674A/en not_active Expired
- 1977-02-22 DD DD7700197500A patent/DD129450A5/xx unknown
- 1977-02-22 YU YU00492/77A patent/YU49277A/xx unknown
- 1977-02-22 PH PH19479A patent/PH13084A/en unknown
- 1977-02-22 NL NL7701884A patent/NL7701884A/xx not_active Application Discontinuation
- 1977-02-22 DK DK76077A patent/DK76077A/da not_active Application Discontinuation
- 1977-02-22 ES ES456162A patent/ES456162A1/es not_active Expired
- 1977-02-22 NO NO770580A patent/NO147069C/no unknown
- 1977-02-23 IE IE380/77A patent/IE44701B1/en unknown
- 1977-02-23 JP JP1974977A patent/JPS52118496A/ja active Pending
- 1977-02-23 CH CH226677A patent/CH631986A5/de not_active IP Right Cessation
-
1978
- 1978-02-27 ES ES467360A patent/ES467360A1/es not_active Expired
- 1978-05-03 FR FR7813145A patent/FR2378034A1/fr active Granted
-
1982
- 1982-05-06 NO NO821500A patent/NO149138C/no unknown
- 1982-06-30 YU YU01419/82A patent/YU141982A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |