SE441597B - Substituerade kinolinkarboxylsyraderivat - Google Patents
Substituerade kinolinkarboxylsyraderivatInfo
- Publication number
- SE441597B SE441597B SE7908065A SE7908065A SE441597B SE 441597 B SE441597 B SE 441597B SE 7908065 A SE7908065 A SE 7908065A SE 7908065 A SE7908065 A SE 7908065A SE 441597 B SE441597 B SE 441597B
- Authority
- SE
- Sweden
- Prior art keywords
- carboxylic acid
- fluoro
- oxo
- piperazinyl
- dihydroquinoline
- Prior art date
Links
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title 1
- -1 p-aminobenzyl Chemical group 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- FIDDSNJKWVGIBL-UHFFFAOYSA-N 6-fluoro-4-oxo-7-piperazin-1-yl-1-propylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C2N(CCC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 FIDDSNJKWVGIBL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- SRVXWYYRMVVKDR-UHFFFAOYSA-N 1-ethyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2CC SRVXWYYRMVVKDR-UHFFFAOYSA-N 0.000 claims description 2
- RPXDRZBUEUOUCV-UHFFFAOYSA-N 6-fluoro-1-(2-fluoroethyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound FC=1C=C2C(=O)C(C(=O)O)=CN(CCF)C2=CC=1N1CCNCC1 RPXDRZBUEUOUCV-UHFFFAOYSA-N 0.000 claims description 2
- QKWMLWIDWFIZHY-UHFFFAOYSA-N 6-fluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2CCF QKWMLWIDWFIZHY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- WKZAVCCKKJQNCJ-UHFFFAOYSA-N ethyl 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylate Chemical compound FC=1C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=CC=1N1CCNCC1 WKZAVCCKKJQNCJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- CGXLVFZJJOXEDF-UHFFFAOYSA-N 1,8-naphthyridine-3-carboxylic acid Chemical class N1=CC=CC2=CC(C(=O)O)=CN=C21 CGXLVFZJJOXEDF-UHFFFAOYSA-N 0.000 claims 1
- VFZWFCNFKARVIJ-UHFFFAOYSA-N 1-ethenyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C=C VFZWFCNFKARVIJ-UHFFFAOYSA-N 0.000 claims 1
- ZMKSHLFZGOROAV-UHFFFAOYSA-N 7-[4-[(4-aminophenyl)methyl]piperazin-1-yl]-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N(CC1)CCN1CC1=CC=C(N)C=C1 ZMKSHLFZGOROAV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
- 241000607715 Serratia marcescens Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- WSMUGWVCMJVSTQ-UHFFFAOYSA-N 7-chloro-6-fluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylic acid Chemical compound ClC1=C(F)C=C2C(=O)C(C(=O)O)=CN(CCF)C2=C1 WSMUGWVCMJVSTQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- QYFJJCLOZHDZHF-UHFFFAOYSA-N 1-ethenyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.FC=1C=C2C(=O)C(C(=O)O)=CN(C=C)C2=CC=1N1CCNCC1 QYFJJCLOZHDZHF-UHFFFAOYSA-N 0.000 description 1
- MQFBDWULSSYFJO-UHFFFAOYSA-N 1-ethenyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C=C MQFBDWULSSYFJO-UHFFFAOYSA-N 0.000 description 1
- OXZPPLXRBFVIGA-UHFFFAOYSA-N 1-ethyl-6-fluoro-7-[4-[(4-nitrophenyl)methyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N(CC1)CCN1CC1=CC=C([N+]([O-])=O)C=C1 OXZPPLXRBFVIGA-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- CUYOWBPVADVNIZ-UHFFFAOYSA-N 6-fluoro-1-(2-fluoroethyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.FC=1C=C2C(=O)C(C(=O)O)=CN(CCF)C2=CC=1N1CCNCC1 CUYOWBPVADVNIZ-UHFFFAOYSA-N 0.000 description 1
- RTYHFPXNYXKYPQ-UHFFFAOYSA-N 7-chloro-1-ethenyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound ClC1=C(F)C=C2C(=O)C(C(=O)O)=CN(C=C)C2=C1 RTYHFPXNYXKYPQ-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241000186064 Trueperella pyogenes Species 0.000 description 1
- 241000607447 Yersinia enterocolitica Species 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- KCOXGCQZFDAHFC-UHFFFAOYSA-N ethyl 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylate Chemical compound FC=1C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=NC=1N1CCNCC1 KCOXGCQZFDAHFC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940098232 yersinia enterocolitica Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- 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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP53120216A JPS5845426B2 (ja) | 1978-09-29 | 1978-09-29 | 置換キノリンカルボン酸誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
SE7908065L SE7908065L (sv) | 1980-03-30 |
SE441597B true SE441597B (sv) | 1985-10-21 |
Family
ID=14780757
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7908065A SE441597B (sv) | 1978-09-29 | 1979-09-28 | Substituerade kinolinkarboxylsyraderivat |
Country Status (12)
Country | Link |
---|---|
US (1) | US4448962A (fr) |
JP (1) | JPS5845426B2 (fr) |
AU (1) | AU534089B2 (fr) |
BE (1) | BE879106A (fr) |
CA (1) | CA1214465A (fr) |
DE (1) | DE2939786C2 (fr) |
ES (1) | ES484578A1 (fr) |
FR (1) | FR2437406A1 (fr) |
GB (1) | GB2034698B (fr) |
HU (1) | HU179214B (fr) |
IT (1) | IT1166909B (fr) |
SE (1) | SE441597B (fr) |
Families Citing this family (84)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR223983A1 (es) | 1978-08-25 | 1981-10-15 | Dainippon Pharmaceutical Co | Un procedimiento para-preparar derivados de acido 6-halogeno-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-carboxilico |
JPS604820B2 (ja) * | 1979-02-26 | 1985-02-06 | 大塚製薬株式会社 | キノリンカルボン酸誘導体 |
JPS5644066U (fr) * | 1979-09-14 | 1981-04-21 | ||
JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
US4670444B1 (en) * | 1980-09-03 | 1999-02-09 | Bayer Ag | and-naphthyridine-3-carboxylic acids and antibacte7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-rial agents containing these compounds |
DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
US4620007A (en) * | 1980-09-03 | 1986-10-28 | Bayer Aktiengesellschaft | 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid |
JPS5762259A (en) * | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
JPS57106681A (en) * | 1980-12-24 | 1982-07-02 | Dainippon Pharmaceut Co Ltd | 1,8-naphthyridine derivative and its salt |
JPS57134482A (en) * | 1981-02-13 | 1982-08-19 | Dainippon Pharmaceut Co Ltd | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation |
SE440354B (sv) * | 1981-02-19 | 1985-07-29 | Kyorin Seiyaku Kk | Kinolinkarboxylsyraderivat |
JPS57145862A (en) * | 1981-03-06 | 1982-09-09 | Kyorin Pharmaceut Co Ltd | Quinolinecarboxylic acid derivative |
JPS57203067A (en) * | 1981-06-10 | 1982-12-13 | Kanebo Ltd | Novel quinolinecarboxylic acid derivatives, their preparations, and antibacterial agent comprising them as active ingredient |
US4530928A (en) * | 1982-01-13 | 1985-07-23 | Merck & Co., Inc. | Quinoline carboxylic acid complexes with guanidinium carbonate |
US4665079A (en) * | 1984-02-17 | 1987-05-12 | Warner-Lambert Company | Antibacterial agents |
US5281612A (en) * | 1982-09-09 | 1994-01-25 | Warner-Lambert Company | Naphthyridine antibacterial agents |
JPS59122470A (ja) * | 1982-12-27 | 1984-07-14 | Dai Ichi Seiyaku Co Ltd | キノリン−3−カルボン酸誘導体の製造法 |
DE3248505A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(4- (oxoalkyl)-1-piperazinyl/-3-chinolincarbonsaeuren und ihre derivate, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3318145A1 (de) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
US4730000A (en) * | 1984-04-09 | 1988-03-08 | Abbott Laboratories | Quinoline antibacterial compounds |
AU553415B2 (en) * | 1983-09-19 | 1986-07-17 | Abbott Japan Co., Ltd. | 6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids |
US4616019A (en) * | 1984-01-26 | 1986-10-07 | Abbott Laboratories | Naphthyridine antibacterial compounds |
US4774246A (en) * | 1984-01-26 | 1988-09-27 | Abbott Laboratories | Quinoline antibacterial compounds |
IT1196051B (it) * | 1984-03-16 | 1988-11-10 | Schiena Ricerche | Composti ad attivita' antibatterica |
US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
DE3420743A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3420770A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
GB8414559D0 (en) * | 1984-06-07 | 1984-07-11 | Scras | Pyridine derivatives |
EP0181521A1 (fr) * | 1984-10-19 | 1986-05-21 | Otsuka Pharmaceutical Co., Ltd. | Composés d'acide 1-phényl substitué-4-oxo-3-quinoléine carboxylique |
DE3443183A1 (de) * | 1984-11-27 | 1986-05-28 | Robert Bosch Gmbh, 7000 Stuttgart | Verfahren und vorrichtung zum steuern der daempferhaerte eines stossdaempfers fuer fahrzeuge |
EP0191185B1 (fr) * | 1984-12-14 | 1990-03-07 | Daiichi Seiyaku Co., Ltd. | Dérivés de l'acide quinoléine-carboxylique |
DE3508816A1 (de) * | 1985-01-10 | 1986-07-10 | Bayer Ag, 5090 Leverkusen | 6,7-disubstituierte 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphtyridin-3-carbonsaeuren |
US4851535A (en) * | 1985-01-23 | 1989-07-25 | Toyama Chemical Co., Ltd. | Nicotinic acid derivatives |
US4755513A (en) * | 1985-01-30 | 1988-07-05 | Otsuka Pharmaceutical Company, Limited | Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds |
DE3509546A1 (de) * | 1985-03-16 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | 7-amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
US4657913A (en) * | 1985-04-18 | 1987-04-14 | Warner-Lambert Company | Trifluoro- quinoline -3- carboxylic acids and their use as anti-bacterial agents |
US4684648A (en) * | 1985-05-10 | 1987-08-04 | Otsuka Pharmaceutical Company Limited | Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds and compositions thereof |
DE3608745A1 (de) * | 1985-07-24 | 1987-01-29 | Bayer Ag | Bakterizide zubereitungen zur anwendung auf dem gebiet der veterinaermedizin |
IN166416B (fr) * | 1985-09-18 | 1990-05-05 | Pfizer | |
JPH0717642B2 (ja) * | 1985-10-09 | 1995-03-01 | 富山化学工業株式会社 | 1,4―ジヒドロ―4―オキソナフチリジン誘導体またはその塩 |
DE3542002A1 (de) * | 1985-11-28 | 1987-06-04 | Bayer Ag | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
CA1306750C (fr) | 1985-12-09 | 1992-08-25 | Istvan Hermecz | Procede pour la preparation d'acides quinoline carboxyliques |
HU196218B (en) | 1985-12-09 | 1988-10-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing quinoline carboxylic acid boric acid anhydrides |
US4687770A (en) * | 1985-12-23 | 1987-08-18 | Abbott Laboratories | Isoxazolo-pyrido-benzoxazine and isothiazolo-pyrido-benzoxazine derivatives |
US4689325A (en) * | 1985-12-23 | 1987-08-25 | Abbott Laboratories | Isoxazolo-pyrido-phenoxazine and isothiazolo-pyrido-phenoxazine derivatives |
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-
1978
- 1978-09-29 JP JP53120216A patent/JPS5845426B2/ja not_active Expired
-
1979
- 1979-09-28 HU HU79KI783A patent/HU179214B/hu unknown
- 1979-09-28 SE SE7908065A patent/SE441597B/sv not_active IP Right Cessation
- 1979-09-28 ES ES484578A patent/ES484578A1/es not_active Expired
- 1979-09-28 IT IT26120/79A patent/IT1166909B/it active
- 1979-10-01 CA CA000336710A patent/CA1214465A/fr not_active Expired
- 1979-10-01 BE BE2/58109A patent/BE879106A/fr not_active IP Right Cessation
- 1979-10-01 FR FR7924447A patent/FR2437406A1/fr active Granted
- 1979-10-01 DE DE2939786A patent/DE2939786C2/de not_active Expired
- 1979-10-01 GB GB7934033A patent/GB2034698B/en not_active Expired
- 1979-10-02 AU AU51421/79A patent/AU534089B2/en not_active Expired
-
1981
- 1981-10-14 US US06/311,343 patent/US4448962A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
DE2939786C2 (de) | 1986-10-09 |
FR2437406B1 (fr) | 1983-06-03 |
IT7926120A0 (it) | 1979-09-28 |
DE2939786A1 (de) | 1980-04-10 |
ES484578A1 (es) | 1980-05-16 |
CA1214465A (fr) | 1986-11-25 |
AU534089B2 (en) | 1984-01-05 |
JPS5547658A (en) | 1980-04-04 |
US4448962A (en) | 1984-05-15 |
BE879106A (fr) | 1980-02-01 |
SE7908065L (sv) | 1980-03-30 |
GB2034698B (en) | 1982-11-17 |
IT1166909B (it) | 1987-05-06 |
FR2437406A1 (fr) | 1980-04-25 |
HU179214B (en) | 1982-09-28 |
GB2034698A (en) | 1980-06-11 |
AU5142179A (en) | 1981-04-16 |
JPS5845426B2 (ja) | 1983-10-08 |
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