BG61122B2 - Оптично активни производни на пиридонкарбоксилната киселина - Google Patents
Оптично активни производни на пиридонкарбоксилната киселина Download PDFInfo
- Publication number
- BG61122B2 BG61122B2 BG098620A BG9862094A BG61122B2 BG 61122 B2 BG61122 B2 BG 61122B2 BG 098620 A BG098620 A BG 098620A BG 9862094 A BG9862094 A BG 9862094A BG 61122 B2 BG61122 B2 BG 61122B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- group
- amino
- cis
- compound
- methylamino
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 26
- 230000003287 optical effect Effects 0.000 title description 4
- 238000011282 treatment Methods 0.000 claims abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 claims abstract 2
- -1 piperazine radical Chemical class 0.000 claims description 216
- 150000001875 compounds Chemical class 0.000 claims description 173
- 239000000203 mixture Substances 0.000 claims description 82
- 125000003277 amino group Chemical group 0.000 claims description 55
- 125000004122 cyclic group Chemical group 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical group CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- ARHYWWAJZDAYDJ-UHFFFAOYSA-N 1,2-dimethylpiperazine Chemical compound CC1CNCCN1C ARHYWWAJZDAYDJ-UHFFFAOYSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract description 6
- 241000894006 Bacteria Species 0.000 abstract description 3
- 230000002458 infectious effect Effects 0.000 abstract description 3
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 194
- 230000002829 reductive effect Effects 0.000 description 114
- 239000000243 solution Substances 0.000 description 108
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 96
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 88
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 79
- 239000002904 solvent Substances 0.000 description 76
- 239000013078 crystal Substances 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 238000002844 melting Methods 0.000 description 61
- 230000008018 melting Effects 0.000 description 61
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- 239000011541 reaction mixture Substances 0.000 description 57
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 54
- 230000000052 comparative effect Effects 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 42
- 238000005160 1H NMR spectroscopy Methods 0.000 description 36
- 238000000921 elemental analysis Methods 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- 229940086542 triethylamine Drugs 0.000 description 29
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000284 extract Substances 0.000 description 22
- 238000001914 filtration Methods 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 19
- 239000008346 aqueous phase Substances 0.000 description 19
- 150000007660 quinolones Chemical class 0.000 description 18
- VWSDKMQGCVVQBV-NTSWFWBYSA-N tert-butyl n-[(1r,2s)-2-fluorocyclopropyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1C[C@@H]1F VWSDKMQGCVVQBV-NTSWFWBYSA-N 0.000 description 18
- DTYLXDLAOLOTKT-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=C1 DTYLXDLAOLOTKT-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 230000000845 anti-microbial effect Effects 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical group OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- KGVGRFMTXSHZBB-UHFFFAOYSA-N 1-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=C1)C(=O)C(=CN2[N+](=O)[O-])C(=O)O KGVGRFMTXSHZBB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- HZQKMZGKYVDMCT-GBXIJSLDSA-N (1s,2s)-2-fluorocyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@@H]1F HZQKMZGKYVDMCT-GBXIJSLDSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 241000204031 Mycoplasma Species 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XGTAZORWPDEZKF-ONGXEEELSA-N (3s,4r)-4-amino-1-benzyl-3-methylpyrrolidin-2-one Chemical compound O=C1[C@@H](C)[C@@H](N)CN1CC1=CC=CC=C1 XGTAZORWPDEZKF-ONGXEEELSA-N 0.000 description 4
- CIMIGBCQBKCGOR-UHFFFAOYSA-N 1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=N1 CIMIGBCQBKCGOR-UHFFFAOYSA-N 0.000 description 4
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000006286 aqueous extract Substances 0.000 description 4
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- QRMKWVNXYORDRU-DZGCQCFKSA-N tert-butyl n-[(3s,4s)-1-benzyl-4-methylpyrrolidin-3-yl]carbamate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)[C@@H](C)CN1CC1=CC=CC=C1 QRMKWVNXYORDRU-DZGCQCFKSA-N 0.000 description 4
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- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
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- 201000003146 cystitis Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GSVNICIOQSJQHL-UHFFFAOYSA-N ethyl 3-(3-acetyloxy-2,4,5-trifluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC(F)=C(F)C(OC(C)=O)=C1F GSVNICIOQSJQHL-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- QQWYQAQQADNEIC-RVDMUPIBSA-N tert-butyl [(z)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(/C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-RVDMUPIBSA-N 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 2
- TUKJTSUSKQOYCD-STHAYSLISA-N (1r,2s)-2-fluorocyclopropan-1-amine Chemical compound N[C@@H]1C[C@@H]1F TUKJTSUSKQOYCD-STHAYSLISA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- QGJLSNCHRAYIKZ-UHFFFAOYSA-N 1-cyclopropylquinolin-2-one Chemical class O=C1C=CC2=CC=CC=C2N1C1CC1 QGJLSNCHRAYIKZ-UHFFFAOYSA-N 0.000 description 2
- CISXRFRLKWCFJS-UHFFFAOYSA-N 2,4,5-trifluoro-3-methylbenzoic acid Chemical compound CC1=C(F)C(F)=CC(C(O)=O)=C1F CISXRFRLKWCFJS-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- HZQKMZGKYVDMCT-UHFFFAOYSA-N 2-fluorocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1F HZQKMZGKYVDMCT-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 208000032969 Hemorrhagic Septicemia Diseases 0.000 description 2
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000005188 oxoalkyl group Chemical group 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 201000005115 pasteurellosis Diseases 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 201000006509 pleuropneumonia Diseases 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 201000002765 pyometritis Diseases 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 206010039447 salmonellosis Diseases 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- RDMVVTNPIKHJHP-YUMQZZPRSA-N tert-butyl (2s,4s)-4-amino-2-methylpyrrolidine-1-carboxylate Chemical compound C[C@H]1C[C@H](N)CN1C(=O)OC(C)(C)C RDMVVTNPIKHJHP-YUMQZZPRSA-N 0.000 description 1
- QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-UHFFFAOYSA-N 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
- HJUZGKGDCUOVML-DTWKUNHWSA-N tert-butyl n-[(1s)-1-[(3r)-pyrrolidin-3-yl]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C)[C@@H]1CCNC1 HJUZGKGDCUOVML-DTWKUNHWSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10462588 | 1988-04-27 | ||
| JP29698488 | 1988-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG61122B2 true BG61122B2 (bg) | 1996-11-29 |
Family
ID=26445063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG098620A BG61122B2 (bg) | 1988-04-27 | 1994-02-28 | Оптично активни производни на пиридонкарбоксилната киселина |
Country Status (26)
| Country | Link |
|---|---|
| US (4) | US5587386A (el) |
| EP (1) | EP0341493B1 (el) |
| JP (5) | JP2714597B2 (el) |
| KR (1) | KR0184614B1 (el) |
| CN (1) | CN1033751C (el) |
| AT (1) | ATE182145T1 (el) |
| AU (1) | AU625414B2 (el) |
| BG (1) | BG61122B2 (el) |
| CA (1) | CA1340801C (el) |
| DE (1) | DE68929030T2 (el) |
| DK (1) | DK175467B1 (el) |
| ES (1) | ES2135372T3 (el) |
| FI (1) | FI96947C (el) |
| GR (1) | GR3031365T3 (el) |
| HK (1) | HK1002108A1 (el) |
| HU (1) | HU211136A9 (el) |
| IL (1) | IL90062A (el) |
| LV (1) | LV10092B (el) |
| MY (1) | MY105136A (el) |
| NO (1) | NO175939C (el) |
| NZ (1) | NZ228893A (el) |
| PT (1) | PT90377B (el) |
| RU (1) | RU2075475C1 (el) |
| SG (1) | SG48036A1 (el) |
| UA (1) | UA29378C2 (el) |
| YU (1) | YU48432B (el) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL90062A (en) * | 1988-04-27 | 1994-10-07 | Daiichi Seiyaku Co | History of pyridonecarboxylic acid, their preparation and pharmaceutical preparations containing them |
| JPH0674261B2 (ja) * | 1988-06-21 | 1994-09-21 | 塩野義製薬株式会社 | キノロンカルボン酸誘導体 |
| CA1336090C (en) * | 1988-08-31 | 1995-06-27 | Isao Hayakawa | Spiro-substituted cyclic amines of quinolone derivatives |
| CA2036516A1 (en) * | 1990-02-19 | 1991-08-20 | Yoshikazu Asahina | Optically active 8-methoxyouinolonecarboxylic acid derivatives, their preparative processes and their intermediates |
| MY109714A (en) * | 1990-10-18 | 1997-04-30 | Daiichi Seiyaku Co | Process for preparing 8-chloroquinolone derivatives |
| ES2151488T3 (es) * | 1991-05-28 | 2001-01-01 | Daiichi Seiyaku Co | Derivado de acido piridonacarboxilico. |
| ATE184603T1 (de) * | 1991-06-19 | 1999-10-15 | Pfizer | Azaspirochinolone als antibakterielle wirkstoffe |
| KR960011370B1 (ko) * | 1991-12-31 | 1996-08-22 | 재단법인 한국화학연구소 | 스피로알킬아민 유도체와 그의 제조방법 |
| NO301165B1 (no) * | 1992-12-25 | 1997-09-22 | Daiichi Seiyaku Co | Bicykliske aminderivater og antibakterielle midler inneholdende disse |
| ZA946853B (en) * | 1993-09-10 | 1995-04-24 | Daiichi Seiyaku Co | Crystals of antimicrobial compound. |
| CZ12097A3 (en) * | 1994-07-18 | 1997-09-17 | Ube Industries | Trifluoromethylquinolinecarboxylic acid derivatives and pharmaceutical composition containing thereof |
| CA2212007C (en) * | 1995-02-02 | 2004-09-14 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives substitued by a bicyclic amino group |
| TW466237B (en) | 1995-02-07 | 2001-12-01 | Daiichi Seiyaku Co | Heterocyclic spiro-derivative |
| JPH09124556A (ja) | 1995-08-30 | 1997-05-13 | Dai Ichi Seiyaku Co Ltd | ハロゲン化シクロプロパン誘導体の製造方法 |
| CN1119343C (zh) * | 1995-11-22 | 2003-08-27 | 第一制药株式会社 | 取代的氨基环烷基吡咯烷衍生物 |
| US6121285A (en) * | 1995-11-22 | 2000-09-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives |
| IL124944A (en) * | 1996-02-09 | 2003-06-24 | Toyama Chemical Co Ltd | Quinolonecarboxylic acid derivatives or their salts and pharmaceutical compositions containing them |
| ID16655A (id) * | 1996-04-24 | 1997-10-30 | Daiichi Seiyaku Co | Turunan-turunan sikloalkilaminometilpirolidina |
| WO1998024781A1 (fr) * | 1996-12-04 | 1998-06-11 | Daiichi Pharmaceutical Co., Ltd. | Derives d'aminomethylpyrrolidine substitue |
| ATE297912T1 (de) * | 1998-11-24 | 2005-07-15 | Daiichi Seiyaku Co | Cycloalkylsubstituierte aminomethylpyrrolidin- derivate |
| ATE268329T1 (de) * | 1999-03-10 | 2004-06-15 | Daiichi Seiyaku Co | Aminomethylpyrrolidin-derivate mit aromatischen substituenten |
| CN1343128B (zh) | 1999-03-17 | 2010-04-21 | 第一制药株式会社 | 药物组合物 |
| DK1262477T3 (da) * | 2000-02-09 | 2008-12-01 | Daiichi Sankyo Co Ltd | Antibakterielle midler, der er virksomme mod syrefaste bakterier og indeholder pyridoncarboxylsyrer som aktiv ingrediens |
| NZ522667A (en) | 2000-03-31 | 2004-06-25 | Daiichi Seiyaku Co | Quinolonecarboxylic acid derivative with high antibacterial acitivity and safety and highly stable to light and ahumidity. |
| CA2406849C (en) * | 2000-04-24 | 2007-10-23 | Daiichi Pharmaceutical Co., Ltd. | Stabilized liquid preparation |
| CA2417764C (en) | 2000-08-08 | 2009-05-05 | Katsuo Kataoka | Highly absorbable solid preparations containing sitafloxacin and tartaric acid |
| RU2004136997A (ru) * | 2002-05-17 | 2005-06-27 | Дайити Фармасьютикал Ко., Лтд. (JP) | Способ получения производных хинолонкарбоновой кислоты |
| CN1304356C (zh) * | 2003-01-07 | 2007-03-14 | 第一制药株式会社 | 还原脱卤方法 |
| US7085154B2 (en) * | 2003-06-03 | 2006-08-01 | Samsung Electronics Co., Ltd. | Device and method for pulse width control in a phase change memory device |
| JP4820290B2 (ja) | 2004-05-13 | 2011-11-24 | 第一三共株式会社 | 置換ピロリジン誘導体 |
| US7563805B2 (en) | 2005-05-19 | 2009-07-21 | Daiichi Pharmaceutical Co., Ltd. | Tri-, tetra-substituted-3-aminopyrrolidine derivative |
| JP5063032B2 (ja) * | 2005-05-19 | 2012-10-31 | 第一三共株式会社 | トリ−、テトラ−置換−３−アミノピロリジン誘導体 |
| US7928232B2 (en) * | 2005-05-20 | 2011-04-19 | Daiichi Sankyo Company, Limited | Method for producing asymmetric tetrasubstituted carbon atom-containing compound |
| US7977346B2 (en) | 2006-01-17 | 2011-07-12 | Guoqing Paul Chen | Spiro compounds and methods of use |
| TWI386401B (zh) * | 2006-03-27 | 2013-02-21 | Daiichi Seiyaku Co | 醫藥用水合物 |
| WO2008082009A2 (en) | 2007-01-05 | 2008-07-10 | Daiichi Sankyo Company, Limited | Fused substituted aminopyrrolidine derivative |
| JP5414395B2 (ja) | 2008-07-11 | 2014-02-12 | 住友化学株式会社 | （１ｓ，２ｒ）−２−クロロ−２−フルオロシクロプロパンカルボン酸の製造方法 |
| FR2961207B1 (fr) * | 2010-06-09 | 2013-01-18 | Oreal | Utilisation d'un derive de 4- carboxy 2-pyrrolidinone comme solvant dans les compositions cosmetiques ; compositions cosmetiques les contenant ; nouveaux composes |
| CN103467448B (zh) * | 2013-09-18 | 2015-04-15 | 浙江司太立制药股份有限公司 | 7-(3-氨基-4-烷氧亚胺基-1-哌啶基)-1-[(1r,2s)-2-氟环丙基]喹诺酮羧酸类化合物及其制备方法 |
| EP2957561A1 (en) * | 2014-06-18 | 2015-12-23 | Université Paris 6 Pierre et Marie Curie UPMC | Novel fluoroquinolones and use thereof to treat bacterial infections |
| CN105330590B (zh) * | 2015-10-15 | 2018-09-25 | 广州市朗启医药科技有限责任公司 | 西他沙星五元环侧链中间体的制备方法 |
| CN109912504B (zh) * | 2019-04-04 | 2020-11-10 | 山东省联合农药工业有限公司 | 一种喹啉羧酸类化合物及其制备方法与用途 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0191185B1 (en) * | 1984-12-14 | 1990-03-07 | Daiichi Seiyaku Co., Ltd. | Quinoline-carboxylic acid derivatives |
| HUT40639A (en) * | 1985-03-08 | 1987-01-28 | Kyorin Seiyaku Kk | Process for producing quinolon-carboxylic acid derivative and pharmaceutical composition containing them |
| 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 |
| US4668680A (en) * | 1985-12-12 | 1987-05-26 | Warner-Lambert Company | 5-amino-6,8-difluoroquinolones as antibacterial agents |
| US4735949A (en) | 1986-02-18 | 1988-04-05 | Warner-Lambert Company | Disubstituted-7-pyrrolidinonaphthyridine antibacterial agents |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| DE3702393A1 (de) * | 1987-01-28 | 1988-08-11 | Bayer Ag | 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo- 3-chinolincarbonsaeuren, verfahren zu ihrer herstellung und diese enthaltende antibakterielle mittel |
| US5290934A (en) * | 1987-04-16 | 1994-03-01 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
| US4851418A (en) * | 1987-08-21 | 1989-07-25 | Warner-Lambert Company | Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent |
| IL90062A (en) * | 1988-04-27 | 1994-10-07 | Daiichi Seiyaku Co | History of pyridonecarboxylic acid, their preparation and pharmaceutical preparations containing them |
| FI95130C (fi) * | 1988-07-20 | 1995-12-27 | Sankyo Co | Menetelmä lääkeaineena käyttökelpoisten 4-oksokinoliini-3-karboksyylihapon johdannaisten valmistamiseksi |
| US5286723A (en) | 1988-08-31 | 1994-02-15 | Daiichi Seiyaku Co., Ltd. | Spiro compound |
| AU5123690A (en) * | 1989-03-13 | 1990-09-13 | Bristol-Myers Squibb Company | 5-substituted-1,4-dihydro-4-oxo-nephthyridine-3-carboxylate antibacterial agents |
| DE3910663A1 (de) * | 1989-04-03 | 1990-10-04 | Bayer Ag | 5-alkylchinoloncarbonsaeuren |
| NZ522667A (en) * | 2000-03-31 | 2004-06-25 | Daiichi Seiyaku Co | Quinolonecarboxylic acid derivative with high antibacterial acitivity and safety and highly stable to light and ahumidity. |
| JP4820290B2 (ja) * | 2004-05-13 | 2011-11-24 | 第一三共株式会社 | 置換ピロリジン誘導体 |
-
1989
- 1989-04-24 IL IL9006289A patent/IL90062A/en unknown
- 1989-04-24 MY MYPI89000521A patent/MY105136A/en unknown
- 1989-04-25 NO NO891698A patent/NO175939C/no not_active IP Right Cessation
- 1989-04-26 AT AT89107550T patent/ATE182145T1/de not_active IP Right Cessation
- 1989-04-26 DE DE68929030T patent/DE68929030T2/de not_active Expired - Lifetime
- 1989-04-26 AU AU33702/89A patent/AU625414B2/en not_active Ceased
- 1989-04-26 SG SG1996006401A patent/SG48036A1/en unknown
- 1989-04-26 PT PT90377A patent/PT90377B/pt not_active IP Right Cessation
- 1989-04-26 FI FI891980A patent/FI96947C/fi not_active IP Right Cessation
- 1989-04-26 ES ES89107550T patent/ES2135372T3/es not_active Expired - Lifetime
- 1989-04-26 CA CA000597865A patent/CA1340801C/en not_active Expired - Fee Related
- 1989-04-26 UA UA5001894A patent/UA29378C2/uk unknown
- 1989-04-26 EP EP89107550A patent/EP0341493B1/en not_active Expired - Lifetime
- 1989-04-26 NZ NZ228893A patent/NZ228893A/xx unknown
- 1989-04-26 JP JP1106762A patent/JP2714597B2/ja not_active Expired - Lifetime
- 1989-04-26 YU YU87589A patent/YU48432B/sh unknown
- 1989-04-27 KR KR1019890005539A patent/KR0184614B1/ko not_active IP Right Cessation
- 1989-04-27 CN CN89103911A patent/CN1033751C/zh not_active Expired - Lifetime
- 1989-04-27 DK DK205789A patent/DK175467B1/da not_active IP Right Cessation
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1991
- 1991-10-29 RU SU915001894A patent/RU2075475C1/ru not_active IP Right Cessation
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1992
- 1992-12-30 LV LVP-92-696A patent/LV10092B/en unknown
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1993
- 1993-10-28 US US08/142,105 patent/US5587386A/en not_active Ceased
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1994
- 1994-02-28 BG BG098620A patent/BG61122B2/bg unknown
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1995
- 1995-04-13 JP JP7088282A patent/JP2903292B2/ja not_active Expired - Lifetime
- 1995-06-07 US US08/477,886 patent/US5767127A/en not_active Expired - Lifetime
- 1995-06-22 HU HU95P/P00371P patent/HU211136A9/hu unknown
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1997
- 1997-07-31 JP JP9205599A patent/JP2917010B2/ja not_active Expired - Fee Related
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1998
- 1998-01-21 HK HK98100553A patent/HK1002108A1/xx not_active IP Right Cessation
- 1998-04-06 US US09/055,127 patent/US6031102A/en not_active Expired - Fee Related
- 1998-08-20 JP JP10233763A patent/JPH11124367A/ja active Pending
- 1998-08-20 JP JP10233764A patent/JPH11124380A/ja active Pending
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1999
- 1999-09-29 GR GR990402459T patent/GR3031365T3/el unknown
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2004
- 2004-06-03 US US10/859,587 patent/USRE41149E1/en not_active Expired - Lifetime
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