CA2005015A1 - Derive d'acide quinolone carboxylique, preparation dudit derive et compose pharmaceutique le contenant - Google Patents

Derive d'acide quinolone carboxylique, preparation dudit derive et compose pharmaceutique le contenant

Info

Publication number: CA2005015A1
Authority: CA; Canada
Prior art keywords: compound; acid; methoxy; methyl; oxoquinoline
Prior art date: 1988-12-09
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.): Abandoned

Application number

CA 2005015

Other languages

English (en)

Inventor

Jun-Ichi Matsumoto

Akira Minamida

Tohru Hirose

Junji Nakano

Shinichi Nakamura

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sumitomo Pharma Co Ltd

Original Assignee

Dainippon Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1988-12-09

Filing date

1989-12-08

Publication date

1990-06-09

1989-12-08 Application filed by Dainippon Pharmaceutical Co Ltd filed Critical Dainippon Pharmaceutical Co Ltd

1990-06-09 Publication of CA2005015A1 publication Critical patent/CA2005015A1/fr

Status Abandoned legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title description 5
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 94
150000003839 salts Chemical class 0.000 claims abstract description 19
KQDBKGTYINCAHF-UHFFFAOYSA-N 1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6-fluoro-8-methoxy-5-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(C)C(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CC(C)NC(C)C1 KQDBKGTYINCAHF-UHFFFAOYSA-N 0.000 claims abstract description 5
-1 1-cyclopropyl-6-fluoro-8-methoxy-5-methyl-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid Chemical compound 0.000 claims description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
239000004480 active ingredient Substances 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
150000004885 piperazines Chemical class 0.000 claims 1
238000000034 method Methods 0.000 abstract description 15
239000003242 anti bacterial agent Substances 0.000 abstract description 9
230000008569 process Effects 0.000 abstract description 5
229940072132 quinolone antibacterials Drugs 0.000 abstract description 5
241001465754 Metazoa Species 0.000 abstract description 4
238000011282 treatment Methods 0.000 abstract description 3
208000035143 Bacterial infection Diseases 0.000 abstract description 2
208000022362 bacterial infectious disease Diseases 0.000 abstract description 2
238000011321 prophylaxis Methods 0.000 abstract description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
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238000006243 chemical reaction Methods 0.000 description 19
229940125904 compound 1 Drugs 0.000 description 14
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125000006239 protecting group Chemical group 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000007858 starting material Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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238000002474 experimental method Methods 0.000 description 9
238000001727 in vivo Methods 0.000 description 9
QBHWFWYRQXTGFP-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-8-methoxy-5-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(F)C(F)=C(C)C(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 QBHWFWYRQXTGFP-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
230000000844 anti-bacterial effect Effects 0.000 description 8
239000002585 base Substances 0.000 description 8
229940126062 Compound A Drugs 0.000 description 7
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
125000005907 alkyl ester group Chemical group 0.000 description 7
239000000725 suspension Substances 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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239000007924 injection Substances 0.000 description 5
210000002966 serum Anatomy 0.000 description 5
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
241000588724 Escherichia coli Species 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000009102 absorption Effects 0.000 description 4
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WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
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230000000694 effects Effects 0.000 description 4
ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 4
229960001395 fenbufen Drugs 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
229960000443 hydrochloric acid Drugs 0.000 description 4
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238000000338 in vitro Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
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239000011734 sodium Substances 0.000 description 4
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ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
IFNWESYYDINUHV-OLQVQODUSA-N (2s,6r)-2,6-dimethylpiperazine Chemical compound C[C@H]1CNC[C@@H](C)N1 IFNWESYYDINUHV-OLQVQODUSA-N 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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229910000147 aluminium phosphate Inorganic materials 0.000 description 3
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150000004649 carbonic acid derivatives Chemical class 0.000 description 3
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DYPBKZJQVSIPJY-AOOOYVTPSA-N 1-cyclopropyl-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-5-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(C)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DYPBKZJQVSIPJY-AOOOYVTPSA-N 0.000 description 2
IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 description 2
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CQTYNTUPZMNLDM-UHFFFAOYSA-N 2,4,5-trifluoro-3-methoxy-6-methylbenzoic acid Chemical compound COC1=C(F)C(F)=C(C)C(C(O)=O)=C1F CQTYNTUPZMNLDM-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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231100000111 LD50 Toxicity 0.000 description 1
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239000002841 Lewis acid Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000204031 Mycoplasma Species 0.000 description 1
241001138504 Mycoplasma bovis Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010034972 Photosensitivity reaction Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
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UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
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241000194017 Streptococcus Species 0.000 description 1
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229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
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238000004458 analytical method Methods 0.000 description 1
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229910001863 barium hydroxide Inorganic materials 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
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230000003197 catalytic effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
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238000002512 chemotherapy Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229960003405 ciprofloxacin Drugs 0.000 description 1
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238000004440 column chromatography Methods 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
230000002920 convulsive effect Effects 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
HAHNKKIPLAKGOT-UHFFFAOYSA-N dimethyl 3,4,6-trifluoro-5-methoxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=C(F)C(F)=C(OC)C(F)=C1C(=O)OC HAHNKKIPLAKGOT-UHFFFAOYSA-N 0.000 description 1
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150000002148 esters Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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238000001914 filtration Methods 0.000 description 1
235000019249 food preservative Nutrition 0.000 description 1
239000005452 food preservative Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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150000002337 glycosamines Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
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150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
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239000011259 mixed solution Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
208000007578 phototoxic dermatitis Diseases 0.000 description 1
231100000018 phototoxicity Toxicity 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000036325 urinary excretion Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229960001763 zinc sulfate Drugs 0.000 description 1
229910000368 zinc sulfate Inorganic materials 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 2005015 1988-12-09 1989-12-08 Derive d'acide quinolone carboxylique, preparation dudit derive et compose pharmaceutique le contenant Abandoned CA2005015A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP31265388		1988-12-09
JP312653/88		1988-12-09
JP15640089		1989-06-19
JP156400/89		1989-06-19

Publications (1)

Publication Number	Publication Date
CA2005015A1 true CA2005015A1 (fr)	1990-06-09

Family

ID=26484166

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2005015 Abandoned CA2005015A1 (fr)	1988-12-09	1989-12-08	Derive d'acide quinolone carboxylique, preparation dudit derive et compose pharmaceutique le contenant

Country Status (3)

Country	Link
AU (1)	AU4638889A (fr)
CA (1)	CA2005015A1 (fr)
WO (1)	WO1990006305A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6897315B2 (en)	1997-11-24	2005-05-24	Bayer Healthcare Aktiengesellschaft	Method for producing 8-methoxy-quinolinecarboxylic acids

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62228063A (ja) *	1985-12-27	1987-10-06	Sankyo Co Ltd	キノリンカルボン酸誘導体
JPS63198664A (ja) *	1986-03-31	1988-08-17	Sankyo Co Ltd	キノロンカルボン酸誘導体

1989
- 1989-12-05 AU AU46388/89A patent/AU4638889A/en not_active Abandoned
- 1989-12-05 WO PCT/JP1989/001217 patent/WO1990006305A1/fr not_active Ceased
- 1989-12-08 CA CA 2005015 patent/CA2005015A1/fr not_active Abandoned

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6897315B2 (en)	1997-11-24	2005-05-24	Bayer Healthcare Aktiengesellschaft	Method for producing 8-methoxy-quinolinecarboxylic acids
US7115744B2 (en)	1997-11-24	2006-10-03	Bayer Healthcare Aktiengesellschaft	Method for producing 8-methoxy-quinolinecarboxylic acids

Also Published As

Publication number	Publication date
AU4638889A (en)	1990-06-26
WO1990006305A1 (fr)	1990-06-14

Legal Events

Date	Code	Title	Description
1992-06-08	FZDE	Dead

Publication	Publication Date	Title
EP0221463B1 (fr)	1991-08-14	Dérivés de la quinoléine etleurs procédés de préparation
US4886810A (en)	1989-12-12	Quinoline derivatives, pharmaceutical composition and method of use
DK171330B1 (da)	1996-09-09	Pyridoncarboxylsyre-derivater, fremgangsmåde til fremstilling deraf samt antibakterielt farmaceutisk præparat
EP0132845A2 (fr)	1985-02-13	Dérivés de la 1,8-naphtyridine et procédé pour leur préparation
HU219488B (hu)	2001-04-28	Kinolon-karbonsavszármazék, ezt tartalmazó gyógyszerkészítmény és eljárás előállításukra
HU199821B (en)	1990-03-28	Process for production of derivatives of in 8 position substituated quinoline carbonic acid and medical compositions containing them
US4429127A (en)	1984-01-31	Quinoline carboxylic acid derivative
Remuzon et al.	1991	Fluoronaphthyridines and-quinolones as antibacterial agents. 3. Synthesis and structure-activity relationships of new 1-(1, 1-dimethyl-2-fluoroethyl), 1-[1-methyl-1-(fluoromethyl)-2-fluoroethyl], and 1-[1, 1-(difluoromethyl)-2-fluoroethyl] substituted derivatives
US4738968A (en)	1988-04-19	1,8-naphthyridine derivatives useful as anti-bacterial agents
US5013841A (en)	1991-05-07	Oxo quinoline derivatives
JPH0819120B2 (ja)	1996-02-28	キノリン誘導体
US4496566A (en)	1985-01-29	Naphthyridine derivatives
EP0319906A2 (fr)	1989-06-14	Dérivés de la quinoléine, procédé de leur préparation et agent antibactérien les contenant
CA2005015A1 (fr)	1990-06-09	Derive d'acide quinolone carboxylique, preparation dudit derive et compose pharmaceutique le contenant
US5164392A (en)	1992-11-17	Quinoline derivatives and antibacterial agent containing them
KR970001159B1 (ko)	1997-01-29	신규 1,8-나프티리딘 유도체 및 그의 제조방법
JPS6270370A (ja)	1987-03-31	キノロンカルボン酸誘導体およびその製造方法
KR0167486B1 (ko)	1999-01-15	6-메틸-5-아미노 퀴놀린 카복실산 유도체 및 그의 제조방법
CS277409B6 (cs)	1993-03-17	Nové deriváty chinolinu, jejich estery a soli
KR970011154B1 (ko)	1997-07-07	신규 6-메틸퀴놀론계 화합물 및 그의 제조방법
JPWO1990006305A1 (ja)	1990-11-01	キノロンカルボン酸誘導体、その製造法およびそれを含有する医薬組成物
CS277016B6 (en)	1992-11-18	Novel derivatives of quinoline, process of their preparation and a pharmaceutical based thereon
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