PT89352B - Processo para a preparacao de derivados dos acidos 7-(1-azetidinil)-1,4-dihidro-4-oxoquinoleina-3-carboxilicos e de composicoes farmaceuticas que os contem - Google Patents
Processo para a preparacao de derivados dos acidos 7-(1-azetidinil)-1,4-dihidro-4-oxoquinoleina-3-carboxilicos e de composicoes farmaceuticas que os contem Download PDFInfo
- Publication number
- PT89352B PT89352B PT89352A PT8935288A PT89352B PT 89352 B PT89352 B PT 89352B PT 89352 A PT89352 A PT 89352A PT 8935288 A PT8935288 A PT 8935288A PT 89352 B PT89352 B PT 89352B
- Authority
- PT
- Portugal
- Prior art keywords
- dihydro
- oxo
- azetidinyl
- cyclopropyl
- difluoro
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 65
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 85
- -1 alkyl radical Chemical class 0.000 claims description 83
- 239000002253 acid Substances 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
- YCAZALSUJDPQPP-UHFFFAOYSA-N 4-oxo-3h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)C=NC2=C1 YCAZALSUJDPQPP-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- CTJMNBROBOZHAP-UHFFFAOYSA-N 7-(3-aminoazetidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 CTJMNBROBOZHAP-UHFFFAOYSA-N 0.000 claims description 3
- URLUPDCRQWXDCW-UHFFFAOYSA-N 7-[3-(aminomethyl)azetidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CN)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F URLUPDCRQWXDCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- LTEMZCCDDFSPQZ-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6,8-difluoro-7-[3-methyl-3-[(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(NC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=CC=3)F)C2=C1F LTEMZCCDDFSPQZ-UHFFFAOYSA-N 0.000 claims description 2
- XZLGGGLACMVVTI-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-[3-[[(2,2,2-trifluoroacetyl)amino]methyl]azetidin-1-yl]quinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(CNC(=O)C(F)(F)F)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 XZLGGGLACMVVTI-UHFFFAOYSA-N 0.000 claims description 2
- UAYYWDWWESZIPA-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 UAYYWDWWESZIPA-UHFFFAOYSA-N 0.000 claims description 2
- UHRNUAOWXYNRRP-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-6,8-difluoro-1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(F)=CC=3)C2=C1F UHRNUAOWXYNRRP-UHFFFAOYSA-N 0.000 claims description 2
- UUXXDPWABMNWFB-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-6-fluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2CCF UUXXDPWABMNWFB-UHFFFAOYSA-N 0.000 claims description 2
- LFUFXWPGZKTTHK-UHFFFAOYSA-N 7-[3-(aminomethyl)-3-methylazetidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(CN)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F LFUFXWPGZKTTHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- HUISPBVVUOUAHW-UHFFFAOYSA-N 6,8-difluoro-1-(4-fluorophenyl)-7-[3-methyl-3-[(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(NC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C=CC(F)=CC=3)C2=C1F HUISPBVVUOUAHW-UHFFFAOYSA-N 0.000 claims 1
- JMWWRQAAIBOINE-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F JMWWRQAAIBOINE-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- MEPPHXILHQKRGG-UHFFFAOYSA-N ethyl 7-[3-(acetamidomethyl)azetidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(N3CC(CNC(C)=O)C3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 MEPPHXILHQKRGG-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 2
- ZMZJWNQVCHLZAX-UHFFFAOYSA-N 7-(azetidin-1-yl)-4-oxo-1h-quinoline-3-carboxylic acid Chemical class C=1C=C2C(=O)C(C(=O)O)=CNC2=CC=1N1CCC1 ZMZJWNQVCHLZAX-UHFFFAOYSA-N 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 102
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 93
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- 238000002844 melting Methods 0.000 description 53
- 230000008018 melting Effects 0.000 description 53
- 238000004611 spectroscopical analysis Methods 0.000 description 52
- 239000000203 mixture Substances 0.000 description 39
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 238000010992 reflux Methods 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- RGNZSFXVBCYEPT-UHFFFAOYSA-N 2,2,2-trifluoro-n-(3-methylazetidin-3-yl)acetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)NC1(C)CNC1 RGNZSFXVBCYEPT-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- NMASXYCNDJMMFR-UHFFFAOYSA-N 1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 NMASXYCNDJMMFR-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 244000005700 microbiome Species 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 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 description 5
- FEMZVDSBIXDODB-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F FEMZVDSBIXDODB-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000167854 Bourreria succulenta Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- 241000607768 Shigella Species 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 235000019693 cherries Nutrition 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NCMNCUSDKZJEKW-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(O)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F NCMNCUSDKZJEKW-UHFFFAOYSA-N 0.000 description 2
- IQYHBRUTDXPOJT-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-(3-methylsulfonyloxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(OS(=O)(=O)C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F IQYHBRUTDXPOJT-UHFFFAOYSA-N 0.000 description 2
- HVUJMIKTWOKCJD-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(ethylaminomethyl)-3-methylazetidin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CNCC)(C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 HVUJMIKTWOKCJD-UHFFFAOYSA-N 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- 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 description 2
- QLHBFUQSCBWFAS-UHFFFAOYSA-N 7-(3-amino-3-methylazetidin-1-yl)-1-(2,4-difluorophenyl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C=3C(=CC(F)=CC=3)F)C2=C1F QLHBFUQSCBWFAS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- MVBOOIHDYIGMEC-UHFFFAOYSA-N N-ethyl-2,2,2-trifluoro-N-[(3-methylazetidin-3-yl)methyl]acetamide hydrochloride Chemical compound Cl.FC(F)(F)C(=O)N(CC)CC1(C)CNC1 MVBOOIHDYIGMEC-UHFFFAOYSA-N 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- UQUPQEUNHVVNKW-UHFFFAOYSA-N azetidin-1-ium-3-ol;chloride Chemical compound Cl.OC1CNC1 UQUPQEUNHVVNKW-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
- FGICMAMEHORFNK-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 FGICMAMEHORFNK-UHFFFAOYSA-N 0.000 description 2
- PGXGEQOSJMUQBW-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(N3CC(O)C3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 PGXGEQOSJMUQBW-UHFFFAOYSA-N 0.000 description 2
- POZIHPKRJFLANV-UHFFFAOYSA-N ethyl 2-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2NC(=O)C(C(=O)OCC)=CC2=C1 POZIHPKRJFLANV-UHFFFAOYSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
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- DHXXDTCOJUYKOQ-UHFFFAOYSA-N n,n-dimethylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.CN(C)C1CNC1 DHXXDTCOJUYKOQ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- CCEKAJIANROZEO-UHFFFAOYSA-N sulfluramid Chemical group CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CCEKAJIANROZEO-UHFFFAOYSA-N 0.000 description 2
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- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
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- QSNYNWOQOIJCFV-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[3-(methylamino)azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(NC)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F QSNYNWOQOIJCFV-UHFFFAOYSA-N 0.000 description 1
- SZKDCHHLZYNMLV-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[3-methyl-3-[(2,2,2-trifluoroacetyl)amino]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(NC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F SZKDCHHLZYNMLV-UHFFFAOYSA-N 0.000 description 1
- XOMWMRGJYMHAON-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[3-methyl-3-[[(2,2,2-trifluoroacetyl)amino]methyl]azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)(CNC(=O)C(F)(F)F)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F XOMWMRGJYMHAON-UHFFFAOYSA-N 0.000 description 1
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- XDLPWPNVUPKKSN-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[3-(methylamino)azetidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(NC)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 XDLPWPNVUPKKSN-UHFFFAOYSA-N 0.000 description 1
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- IKZBNCORGKYEDZ-UHFFFAOYSA-N 7-(3-aminoazetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F IKZBNCORGKYEDZ-UHFFFAOYSA-N 0.000 description 1
- UXQLQLPOBVXSHN-UHFFFAOYSA-N 7-(azetidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 UXQLQLPOBVXSHN-UHFFFAOYSA-N 0.000 description 1
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- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000588919 Citrobacter freundii Species 0.000 description 1
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- 241000589516 Pseudomonas Species 0.000 description 1
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- 241000607715 Serratia marcescens Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001467018 Typhis Species 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- OOSDLMAZIRAMDN-UHFFFAOYSA-N azetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.NC1CNC1 OOSDLMAZIRAMDN-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
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- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 description 1
- 150000001539 azetidines Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
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- LKIBSJCOAXOWJY-UHFFFAOYSA-N ethyl 4-oxo-3h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)C=NC2=C1 LKIBSJCOAXOWJY-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MKRHDBKTGMBWHU-UHFFFAOYSA-N n,n,3-trimethylazetidin-3-amine;hydrochloride Chemical compound Cl.CN(C)C1(C)CNC1 MKRHDBKTGMBWHU-UHFFFAOYSA-N 0.000 description 1
- MHZANEMPEHAGBC-UHFFFAOYSA-N n-(1-methylazetidin-3-yl)acetamide;hydrochloride Chemical compound Cl.CN1CC(NC(C)=O)C1 MHZANEMPEHAGBC-UHFFFAOYSA-N 0.000 description 1
- HVPRNFJOJFQOMZ-UHFFFAOYSA-N n-(azetidin-3-yl)-2,2,2-trifluoroacetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)NC1CNC1 HVPRNFJOJFQOMZ-UHFFFAOYSA-N 0.000 description 1
- VNLUDOWOYBHVIO-UHFFFAOYSA-N n-(azetidin-3-ylmethyl)-2,2,2-trifluoroacetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)NCC1CNC1 VNLUDOWOYBHVIO-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 1
- 229960001732 pipemidic acid Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 230000000306 recurrent effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960001957 stomatological preparations Drugs 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8718289A FR2625200A1 (en) | 1987-12-29 | 1987-12-29 | 7-(1-Azetidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and their application as medicaments |
| FR888809816A FR2634483B2 (fr) | 1987-12-29 | 1988-07-20 | Derives des acides 7-(1-azetidinyl)-1,4-dihydro-4-oxoquinoleine-3-carboxyliques, leur preparation et leur application en tant que medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT89352A PT89352A (pt) | 1989-12-29 |
| PT89352B true PT89352B (pt) | 1993-09-30 |
Family
ID=26226417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT89352A PT89352B (pt) | 1987-12-29 | 1988-12-28 | Processo para a preparacao de derivados dos acidos 7-(1-azetidinil)-1,4-dihidro-4-oxoquinoleina-3-carboxilicos e de composicoes farmaceuticas que os contem |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4927926A (en, 2012) |
| EP (1) | EP0324298B1 (en, 2012) |
| JP (1) | JPH0813811B2 (en, 2012) |
| KR (1) | KR920004136B1 (en, 2012) |
| AU (1) | AU617735B2 (en, 2012) |
| DE (1) | DE3876969T2 (en, 2012) |
| DK (1) | DK726188A (en, 2012) |
| ES (1) | ES2010114A6 (en, 2012) |
| FR (1) | FR2634483B2 (en, 2012) |
| GR (1) | GR3006664T3 (en, 2012) |
| HU (1) | HU206206B (en, 2012) |
| NO (1) | NO176605C (en, 2012) |
| PT (1) | PT89352B (en, 2012) |
| YU (1) | YU47124B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4839355A (en) * | 1987-09-09 | 1989-06-13 | Sterling Drug Inc. | Tricyclic-pyridinylquinoline compounds, their preparation and use |
| US5173484A (en) * | 1988-02-05 | 1992-12-22 | Bayer Aktiengesellschaft | Quinolone- and naphthyridone carboxylic acid derivatives, process for their production, antibacterial compositions and feed additives containing them |
| DE3814517A1 (de) * | 1988-02-05 | 1989-08-17 | Bayer Ag | Chinolon- und naphthyridoncarbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| 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 |
| EP0366189A3 (en) * | 1988-10-24 | 1992-01-02 | Norwich Eaton Pharmaceuticals, Inc. | Novel antimicrobial lactam-quinolones |
| FR2649106A2 (fr) * | 1989-06-29 | 1991-01-04 | Esteve Labor Dr | Derives d'acides pyridone carboxyliques azetidinyl substitues, leur preparation et leur application en tant que medicament |
| FR2644455B1 (fr) * | 1989-03-16 | 1994-09-23 | Esteve Labor Dr | Derives d'acides pyridone carboxyliques azetidinyl substitues, leur preparation et leur application en tant que medicaments |
| FR2654728B2 (fr) * | 1989-03-16 | 1994-09-23 | Esteve Labor Dr | Derives d'acides pyridone carboxyliques azetidinyl substitues, leur preparation et leur application en tant que medicament. |
| NO177302C (no) * | 1989-03-16 | 1995-08-23 | Esteve Labor Dr | Analogifremgangsmåte til fremstilling av terapeutisk aktive substituerte azetidinylkinolon(naftyridon)karboksylsyrederivater |
| IE912902A1 (en) * | 1990-08-24 | 1992-02-26 | Abbott Lab | Quinbenzoxazine, quinobenzothiazine, and pyrido-acridine¹antineoplastic agents |
| FR2676445B1 (fr) * | 1991-05-16 | 1995-02-03 | Esteve Labor Dr | Derives de pyridone amino acide azetidinyl substitues, leur preparation et leur application en tant que medicaments. |
| US5556861A (en) * | 1991-10-01 | 1996-09-17 | Laboratoire Roger Bellon | 1,8 benzonaphthyridine derivatives and antimicrobial compositions |
| FR2690161B1 (fr) * | 1992-04-16 | 1995-06-30 | Esteve Labor Dr | Derives de pyridone azetidinyl substitues avec activite antimicrobienne. |
| FR2692577B1 (fr) * | 1992-05-26 | 1996-02-02 | Bouchara Sa | Nouvelles quinolones fluorees, leur procede de preparation et les compositions pharmaceutiques en renfermant. |
| JP2005097116A (ja) * | 1999-11-11 | 2005-04-14 | Wakunaga Pharmaceut Co Ltd | キノリンカルボン酸誘導体アルカリ金属塩及びこれを用いたキノリンカルボン酸誘導体の精製法 |
| WO2005026146A1 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Azetidinyl quinolones as antibacterial agents |
| EP1781669B1 (en) * | 2004-08-02 | 2010-10-13 | Glaxo Group Limited | Antibacterial agents |
| EP2797912B1 (en) | 2011-12-01 | 2016-05-25 | Purdue Pharma L.P. | Azetidine-substituted quinoxaline-type piperidine compounds and uses thereof |
| AU2013331493A1 (en) | 2012-10-16 | 2015-04-09 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORyt |
| EA201590750A1 (ru) | 2012-10-16 | 2015-09-30 | Янссен Фармацевтика Нв | СВЯЗАННЫЕ С ФЕНИЛОМ ХИНОЛИНИЛОВЫЕ МОДУЛЯТОРЫ RORγT |
| PE20150778A1 (es) | 2012-10-16 | 2015-05-23 | Janssen Pharmaceutica Nv | Moduladores de quinolinilo unidos a metileno de ror-gamma-t |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| CN105848483A (zh) | 2013-10-15 | 2016-08-10 | 詹森药业有限公司 | RORγt 的喹啉基调节剂 |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| EP3057421B1 (en) * | 2013-10-15 | 2019-11-20 | Janssen Pharmaceutica NV | Alkyl linked quinolinyl modulators of ror(gamma)t |
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| CN113045539B (zh) * | 2021-03-30 | 2021-12-07 | 苏州大学 | 2-(4,4-二氯-1-(8-喹啉基)-2-氮杂环丁基)羧酸酯衍生物的制备方法 |
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| JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| US4540690A (en) * | 1982-02-09 | 1985-09-10 | The Upjohn Company | 2-(Phenylmethylene)cycloalkylamines and -azetidines |
| US4665079A (en) * | 1984-02-17 | 1987-05-12 | Warner-Lambert Company | Antibacterial agents |
| US4777175A (en) * | 1982-09-09 | 1988-10-11 | Warner-Lambert Company | Antibacterial agents |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| JPS6089480A (ja) * | 1983-10-21 | 1985-05-20 | Dainippon Pharmaceut Co Ltd | ピリドンカルボン酸誘導体 |
| JPS60126284A (ja) * | 1983-12-09 | 1985-07-05 | Dainippon Pharmaceut Co Ltd | ピリドンカルボン酸誘導体およびその塩 |
| EP0160284B1 (en) * | 1984-04-26 | 1990-10-24 | Abbott Laboratories | Quino-benoxazine antibacterial compounds |
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| US4617308A (en) * | 1985-01-25 | 1986-10-14 | Warner-Lambert Company | 7-substituted amino-1-aryl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids and derivatives thereof as antibacterial agents |
| DK164287A (da) * | 1986-03-31 | 1987-10-01 | Sankyo Co | Quinolin-3-carboxylsyrederivater og fremgangsmaade til fremstilling deraf og deres anvendelse |
| US5039683A (en) * | 1987-10-26 | 1991-08-13 | Pfizer Inc. | Azetidinyl quinolone carboxylic acids and esters |
| AU603936B2 (en) * | 1988-02-04 | 1990-11-29 | Chenault D. Lee | Disposable vaginal speculum |
-
1988
- 1988-07-20 FR FR888809816A patent/FR2634483B2/fr not_active Expired - Lifetime
- 1988-12-27 US US07/290,315 patent/US4927926A/en not_active Expired - Fee Related
- 1988-12-28 PT PT89352A patent/PT89352B/pt not_active IP Right Cessation
- 1988-12-28 DE DE8888403352T patent/DE3876969T2/de not_active Expired - Fee Related
- 1988-12-28 ES ES8900318A patent/ES2010114A6/es not_active Expired
- 1988-12-28 DK DK726188A patent/DK726188A/da not_active Application Discontinuation
- 1988-12-28 EP EP88403352A patent/EP0324298B1/fr not_active Expired - Lifetime
- 1988-12-28 NO NO885797A patent/NO176605C/no unknown
- 1988-12-28 JP JP63335712A patent/JPH0813811B2/ja not_active Expired - Lifetime
- 1988-12-28 YU YU237088A patent/YU47124B/sh unknown
- 1988-12-29 AU AU27578/88A patent/AU617735B2/en not_active Ceased
- 1988-12-29 KR KR1019880017747A patent/KR920004136B1/ko not_active Expired
- 1988-12-29 HU HU886648A patent/HU206206B/hu not_active IP Right Cessation
-
1992
- 1992-12-24 GR GR920403018T patent/GR3006664T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT50467A (en) | 1990-02-28 |
| DE3876969T2 (de) | 1993-05-19 |
| YU47124B (sh) | 1994-12-28 |
| JPH0813811B2 (ja) | 1996-02-14 |
| YU237088A (en) | 1990-12-31 |
| NO176605C (no) | 1995-05-03 |
| NO176605B (no) | 1995-01-23 |
| DK726188D0 (da) | 1988-12-28 |
| FR2634483B2 (fr) | 1994-03-04 |
| DK726188A (da) | 1989-06-30 |
| KR920004136B1 (ko) | 1992-05-25 |
| EP0324298B1 (fr) | 1992-12-23 |
| HU206206B (en) | 1992-09-28 |
| KR890009911A (ko) | 1989-08-04 |
| AU2757888A (en) | 1989-06-29 |
| JPH01301677A (ja) | 1989-12-05 |
| AU617735B2 (en) | 1991-12-05 |
| NO885797D0 (no) | 1988-12-28 |
| GR3006664T3 (en, 2012) | 1993-06-30 |
| EP0324298A1 (fr) | 1989-07-19 |
| PT89352A (pt) | 1989-12-29 |
| NO885797L (no) | 1989-06-30 |
| US4927926A (en) | 1990-05-22 |
| FR2634483A2 (fr) | 1990-01-26 |
| DE3876969D1 (de) | 1993-02-04 |
| ES2010114A6 (es) | 1989-10-16 |
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| FG3A | Patent granted, date of granting |
Effective date: 19930305 |
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