JPS611683A - ７‐（３‐アリール‐１‐ピペラジニル）‐及び７‐（３‐シクロヘキシル‐１‐ピペラジニル）‐３‐キノロンカルボン酸類 - Google Patents
７‐（３‐アリール‐１‐ピペラジニル）‐及び７‐（３‐シクロヘキシル‐１‐ピペラジニル）‐３‐キノロンカルボン酸類Info
- Publication number
- JPS611683A JPS611683A JP60116836A JP11683685A JPS611683A JP S611683 A JPS611683 A JP S611683A JP 60116836 A JP60116836 A JP 60116836A JP 11683685 A JP11683685 A JP 11683685A JP S611683 A JPS611683 A JP S611683A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- formula
- fluorine
- hydroxyl
- piperazinyl
- 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
- WWCQSPVNNWXXPK-UHFFFAOYSA-N 7-(3-cyclohexylpiperazin-1-yl)-3-oxo-2h-quinoline-2-carboxylic acid Chemical class C1=CC2=CC(=O)C(C(=O)O)N=C2C=C1N(C1)CCNC1C1CCCCC1 WWCQSPVNNWXXPK-UHFFFAOYSA-N 0.000 title 1
- -1 methoxy, amino, dimethylamino Chemical group 0.000 claims abstract description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 229910052731 fluorine Chemical group 0.000 claims abstract description 26
- 239000011737 fluorine Chemical group 0.000 claims abstract description 26
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical group 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000005188 oxoalkyl group Chemical group 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000004677 hydrates Chemical class 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000002541 furyl group Chemical group 0.000 claims abstract description 7
- 125000001544 thienyl group Chemical group 0.000 claims abstract 8
- 125000002252 acyl group Chemical group 0.000 claims abstract 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims description 58
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 7
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- MYSWGUAQZAJSOK-UHFFFAOYSA-N Ciprofloxacin Natural products C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims 6
- DIOIOSKKIYDRIQ-UHFFFAOYSA-N ciprofloxacin hydrochloride Chemical compound Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DIOIOSKKIYDRIQ-UHFFFAOYSA-N 0.000 claims 4
- KNEXGVPHPGXAGF-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 KNEXGVPHPGXAGF-UHFFFAOYSA-N 0.000 claims 1
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 claims 1
- MHDVXFFSJDAWHB-UHFFFAOYSA-N 2-oxo-7-piperazin-1-yl-1h-quinoline-3-carboxylic acid Chemical compound C1=C2NC(=O)C(C(=O)O)=CC2=CC=C1N1CCNCC1 MHDVXFFSJDAWHB-UHFFFAOYSA-N 0.000 claims 1
- XISDPHXOJCIPHX-UHFFFAOYSA-N 2-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N=C1N1CCNCC1 XISDPHXOJCIPHX-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000186359 Mycobacterium Species 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000012216 bentonite Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 2
- WWYFHDNQGVTJJJ-UHFFFAOYSA-N 2-cyclohexylpiperazine Chemical class C1CCCCC1C1NCCNC1 WWYFHDNQGVTJJJ-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 241000606125 Bacteroides Species 0.000 description 2
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- 125000004193 piperazinyl group Chemical group 0.000 description 2
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
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- 150000003856 quaternary ammonium compounds Chemical class 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
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940098362 serratia marcescens Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843420798 DE3420798A1 (de) | 1984-06-04 | 1984-06-04 | 7-(3-aryl-l-piperazinyl)- sowie 7-(3-cyclohexyl-l-piperazinyl)-3-chinoloncarbonsaeuren |
| DE3420798.8 | 1984-06-04 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5342256A Division JPH06279411A (ja) | 1984-06-04 | 1993-12-15 | キノリンカルボン酸誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS611683A true JPS611683A (ja) | 1986-01-07 |
Family
ID=6237597
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60116836A Pending JPS611683A (ja) | 1984-06-04 | 1985-05-31 | ７‐（３‐アリール‐１‐ピペラジニル）‐及び７‐（３‐シクロヘキシル‐１‐ピペラジニル）‐３‐キノロンカルボン酸類 |
| JP5342256A Pending JPH06279411A (ja) | 1984-06-04 | 1993-12-15 | キノリンカルボン酸誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5342256A Pending JPH06279411A (ja) | 1984-06-04 | 1993-12-15 | キノリンカルボン酸誘導体 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4599334A (enExample) |
| EP (1) | EP0169993B1 (enExample) |
| JP (2) | JPS611683A (enExample) |
| KR (1) | KR920000759B1 (enExample) |
| AT (1) | ATE39488T1 (enExample) |
| AU (1) | AU571333B2 (enExample) |
| CA (1) | CA1248954A (enExample) |
| DD (1) | DD240016A5 (enExample) |
| DE (2) | DE3420798A1 (enExample) |
| DK (1) | DK162527C (enExample) |
| ES (3) | ES8607294A1 (enExample) |
| FI (1) | FI82041C (enExample) |
| GR (1) | GR851314B (enExample) |
| HU (1) | HU194866B (enExample) |
| IE (1) | IE57814B1 (enExample) |
| IL (1) | IL75370A (enExample) |
| NO (1) | NO165105C (enExample) |
| NZ (1) | NZ212271A (enExample) |
| PH (1) | PH22492A (enExample) |
| PT (1) | PT80580B (enExample) |
| ZA (1) | ZA854168B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021521238A (ja) * | 2018-04-25 | 2021-08-26 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ａｎｉｍａｌ Ｈｅａｌｔｈ Ｇｍｂｈ | キノロンカルボン酸エステルの加水分解プロセス |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5468861A (en) * | 1984-06-04 | 1995-11-21 | Bayer Aktiengesellschaft | 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and alkyl esters thereof |
| JPS6259263A (ja) * | 1985-09-10 | 1987-03-14 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
| JPH0637489B2 (ja) * | 1985-09-21 | 1994-05-18 | 杏林製薬株式会社 | キノロンカルボン酸誘導体およびその製造方法 |
| DE3683922D1 (de) * | 1985-09-24 | 1992-03-26 | Hoffmann La Roche | Chinolinderivate. |
| AU594983B2 (en) * | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
| 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 |
| EP0230053A3 (en) * | 1986-01-17 | 1988-03-30 | American Cyanamid Company | 7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
| HU204512B (en) * | 1986-01-20 | 1992-01-28 | Kyorin Seiyaku Kk | New process for producing quinoline-carboxylic acid derivatives |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| US4689423A (en) * | 1986-04-01 | 1987-08-25 | Warner-Lambert Company | Process for the preparation of 2,3,4,5-tetrafluorobenzoyl acetates |
| HU196987B (en) * | 1986-10-15 | 1989-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| DE3639465A1 (de) * | 1986-11-18 | 1988-05-19 | Hoechst Ag | Optisch aktive gyrasehemmer, ihre herstellung und verwendung als antibiotika |
| NZ229605A (en) * | 1988-07-15 | 1990-07-26 | Abbott Lab | Preparation of 1,4-dihydro-6-fluoro-7-(piperazin-1-yl)-4-oxo-3-quinoline (or naphthyridine) carboxylic acid derivatives |
| FR2664595B1 (fr) * | 1990-07-10 | 1992-09-18 | Bellon Labor Sa Roger | Nouveaux derives de benzonaphtyridine-1,8, leur preparation et les compositions qui les contiennent. |
| FR2653663A1 (en) * | 1989-10-30 | 1991-05-03 | Bellon Labor Sa Roger | Novel benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them |
| RO108347B1 (ro) * | 1989-10-30 | 1994-04-28 | Bellon Labor Sa Roger | DERIVATI DE BENZO-(b)-NAFTIRIDIN-1,8 SI PROCEDEU DE PREPARARE A ACESTORA |
| EP0449445A3 (en) * | 1990-03-27 | 1993-08-25 | Pfizer Inc. | Preparation of beta-ketoesters useful in preparing quinolone antibiotics |
| JPH05506033A (ja) | 1990-04-18 | 1993-09-02 | ノーウィッチ、イートン、ファーマスーティカルズ、インコーポレーテッド | 抗微生物性キノロニルラクタム類 |
| DE10108750A1 (de) * | 2001-02-23 | 2002-09-05 | Bayer Ag | Verbessertes Verfahren zur Herstellung von Fluorchinoloncarbonsäuren |
| KR100519158B1 (ko) * | 2002-12-21 | 2005-10-06 | 주식회사유한양행 | 퀴놀론 카르복실레이트 유도체의 제조방법 |
| DK2001862T3 (da) * | 2006-03-28 | 2011-08-08 | Warner Chilcott Co Llc | Malatsalte og polymorfe af (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyklopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolincarboxylsyre |
| BRPI0709220A2 (pt) * | 2006-03-28 | 2011-07-12 | Procter & Gamble | processo de acoplamento para preparo de intermediários de quinolona |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5777683A (en) * | 1980-09-03 | 1982-05-15 | Bayer Ag | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro- naphthyridine-3-carboxylic acids or salts thereof, manufacture and antibacterial thereof as active ingredient |
| JPS5910580A (ja) * | 1982-07-09 | 1984-01-20 | Hokuriku Seiyaku Co Ltd | ７−フエニル置換ピペラジノ−４−オキソ−１，４−ジヒドロキノリン−３−カルボン酸誘導体 |
| JPS5929685A (ja) * | 1982-08-11 | 1984-02-16 | Hokuriku Seiyaku Co Ltd | ７−置換フエニルピペラジノ−４−オキソ−１，４−ジヒドロキノリン−３−カルボン酸誘導体 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3142854A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| SE440354B (sv) * | 1981-02-19 | 1985-07-29 | Kyorin Seiyaku Kk | Kinolinkarboxylsyraderivat |
| DE3142856A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoylchlorid |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| DE3248506A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(alkyl-1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3248507A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | Mikrobizide mittel auf chinoloncarbonsaeure basis |
| DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, 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 |
-
1984
- 1984-06-04 DE DE19843420798 patent/DE3420798A1/de not_active Withdrawn
-
1985
- 1985-05-17 US US06/735,493 patent/US4599334A/en not_active Expired - Fee Related
- 1985-05-22 EP EP85106252A patent/EP0169993B1/de not_active Expired
- 1985-05-22 DE DE8585106252T patent/DE3567021D1/de not_active Expired
- 1985-05-22 AT AT85106252T patent/ATE39488T1/de active
- 1985-05-23 NO NO852063A patent/NO165105C/no unknown
- 1985-05-27 PH PH32319A patent/PH22492A/en unknown
- 1985-05-29 GR GR851314A patent/GR851314B/el unknown
- 1985-05-31 NZ NZ212271A patent/NZ212271A/xx unknown
- 1985-05-31 FI FI852205A patent/FI82041C/fi not_active IP Right Cessation
- 1985-05-31 IE IE1364/85A patent/IE57814B1/en not_active IP Right Cessation
- 1985-05-31 AU AU43206/85A patent/AU571333B2/en not_active Ceased
- 1985-05-31 CA CA000482912A patent/CA1248954A/en not_active Expired
- 1985-05-31 IL IL75370A patent/IL75370A/xx unknown
- 1985-05-31 JP JP60116836A patent/JPS611683A/ja active Pending
- 1985-06-03 DK DK249685A patent/DK162527C/da not_active IP Right Cessation
- 1985-06-03 ES ES543839A patent/ES8607294A1/es not_active Expired
- 1985-06-03 ZA ZA854168A patent/ZA854168B/xx unknown
- 1985-06-03 PT PT80580A patent/PT80580B/pt not_active IP Right Cessation
- 1985-06-03 HU HU852145A patent/HU194866B/hu not_active IP Right Cessation
- 1985-06-03 DD DD85276974A patent/DD240016A5/de not_active IP Right Cessation
- 1985-06-03 KR KR1019850003855A patent/KR920000759B1/ko not_active Expired
-
1986
- 1986-02-28 ES ES552573A patent/ES8800195A1/es not_active Expired
- 1986-02-28 ES ES552574A patent/ES8800196A1/es not_active Expired
-
1993
- 1993-12-15 JP JP5342256A patent/JPH06279411A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5777683A (en) * | 1980-09-03 | 1982-05-15 | Bayer Ag | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro- naphthyridine-3-carboxylic acids or salts thereof, manufacture and antibacterial thereof as active ingredient |
| JPS5910580A (ja) * | 1982-07-09 | 1984-01-20 | Hokuriku Seiyaku Co Ltd | ７−フエニル置換ピペラジノ−４−オキソ−１，４−ジヒドロキノリン−３−カルボン酸誘導体 |
| JPS5929685A (ja) * | 1982-08-11 | 1984-02-16 | Hokuriku Seiyaku Co Ltd | ７−置換フエニルピペラジノ−４−オキソ−１，４−ジヒドロキノリン−３−カルボン酸誘導体 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021521238A (ja) * | 2018-04-25 | 2021-08-26 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ａｎｉｍａｌ Ｈｅａｌｔｈ Ｇｍｂｈ | キノロンカルボン酸エステルの加水分解プロセス |
Also Published As
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