DD244553A5 - Verfahren zur herstellung von 5,6-difluor-naphthyridinen und 5,6,8-trifluorchinolinen - Google Patents
Verfahren zur herstellung von 5,6-difluor-naphthyridinen und 5,6,8-trifluorchinolinen Download PDFInfo
- Publication number
- DD244553A5 DD244553A5 DD86289148A DD28914886A DD244553A5 DD 244553 A5 DD244553 A5 DD 244553A5 DD 86289148 A DD86289148 A DD 86289148A DD 28914886 A DD28914886 A DD 28914886A DD 244553 A5 DD244553 A5 DD 244553A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxo
- dihydro
- acid
- ethyl
- compounds
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- -1 5,6,8-trifluoroquinoline-carboxylic acid compound Chemical group 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 54
- 150000001412 amines Chemical class 0.000 abstract description 7
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 239000000203 mixture Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MKMDVNZEIQDZEP-UHFFFAOYSA-N 1,2,3,4-tetrafluoro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=C(F)C(F)=C1F MKMDVNZEIQDZEP-UHFFFAOYSA-N 0.000 description 2
- WLSCGLVTCNCINQ-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-7-[3-(methylaminomethyl)pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CNC)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F WLSCGLVTCNCINQ-UHFFFAOYSA-N 0.000 description 2
- SVEHNJWIJXQLJE-UHFFFAOYSA-N 1-ethyl-5,6,8-trifluoro-7-(7-methyl-2,7-diazaspiro[4.4]nonan-2-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=C(F)C(F)=C1N(C1)CCC21CCN(C)C2 SVEHNJWIJXQLJE-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 2
- AJRDXJVCIORVSV-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F AJRDXJVCIORVSV-UHFFFAOYSA-N 0.000 description 2
- RNGGHZDRIWKJPY-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CN)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F RNGGHZDRIWKJPY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- SFYYMUUQGSQVFT-UHFFFAOYSA-N ethyl 3-oxo-3-(2,3,4,5,6-pentafluorophenyl)propanoate Chemical compound CCOC(=O)CC(=O)C1=C(F)C(F)=C(F)C(F)=C1F SFYYMUUQGSQVFT-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 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 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PKUJRODRXLZVLA-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-4-oxo-7-[3-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]quinoline-3-carboxylic acid Chemical compound C1C(CNC(C)C)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F PKUJRODRXLZVLA-UHFFFAOYSA-N 0.000 description 1
- LEHLTWOUQLFQMB-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(ethylamino)pyrrolidin-1-yl]-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(NCC)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F LEHLTWOUQLFQMB-UHFFFAOYSA-N 0.000 description 1
- ITHQPOFCHYUMGN-UHFFFAOYSA-N 1-cyclopropyl-7-[3-(ethylaminomethyl)pyrrolidin-1-yl]-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(CNCC)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F ITHQPOFCHYUMGN-UHFFFAOYSA-N 0.000 description 1
- KJYCMDODSMDSMF-UHFFFAOYSA-N 1-ethyl-5,6-difluoro-7-(7-methyl-2,7-diazaspiro[4.4]nonan-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=C(F)C(F)=C1N(C1)CCC21CCN(C)C2 KJYCMDODSMDSMF-UHFFFAOYSA-N 0.000 description 1
- QOHGZGPSCREOEX-UHFFFAOYSA-N 1-ethyl-7-(7-ethyl-2,7-diazaspiro[4.4]nonan-2-yl)-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1N(CC)CCC11CN(C=2C(=C3C(C(C(C(O)=O)=CN3CC)=O)=C(F)C=2F)F)CC1 QOHGZGPSCREOEX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SUJKVJSPRDGSJX-UHFFFAOYSA-N 6,8-difluoro-4-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=C(F)C=C2C(=O)C(C(=O)O)=CNC2=C1F SUJKVJSPRDGSJX-UHFFFAOYSA-N 0.000 description 1
- DSFDVDNPOHOYHF-UHFFFAOYSA-N 6-fluoro-4-oxo-1h-1,8-naphthyridine-3-carboxylic acid Chemical class C1=C(F)C=C2C(=O)C(C(=O)O)=CNC2=N1 DSFDVDNPOHOYHF-UHFFFAOYSA-N 0.000 description 1
- FRIAJVUWKSBGQB-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-5,6-difluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C(C(=C1F)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1CC1 FRIAJVUWKSBGQB-UHFFFAOYSA-N 0.000 description 1
- LOAIMLIVHIOXPX-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-ethyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=C(F)C(F)=C1N1CCC(N)C1 LOAIMLIVHIOXPX-UHFFFAOYSA-N 0.000 description 1
- KTRJRDAOHJICSW-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-5,6-difluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(CN)CCN1C(C(=C1F)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1CC1 KTRJRDAOHJICSW-UHFFFAOYSA-N 0.000 description 1
- IUKSPGQZMOUTIK-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-1-ethyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=C(F)C(F)=C1N1CCC(CN)C1 IUKSPGQZMOUTIK-UHFFFAOYSA-N 0.000 description 1
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RQNPMQYSVFPKQM-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2,3,4,5,6-pentafluorobenzoyl)prop-2-enoate Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1C(=O)C(C(=O)OCC)=CNC1CC1 RQNPMQYSVFPKQM-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 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
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 239000011345 viscous material Substances 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
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/724,442 US4657913A (en) | 1985-04-18 | 1985-04-18 | Trifluoro- quinoline -3- carboxylic acids and their use as anti-bacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD244553A5 true DD244553A5 (de) | 1987-04-08 |
Family
ID=24910460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86289148A DD244553A5 (de) | 1985-04-18 | 1986-04-15 | Verfahren zur herstellung von 5,6-difluor-naphthyridinen und 5,6,8-trifluorchinolinen |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4657913A (fr) |
| EP (1) | EP0202763B1 (fr) |
| JP (1) | JPS61243077A (fr) |
| KR (1) | KR890005199B1 (fr) |
| CN (1) | CN1012064B (fr) |
| AR (1) | AR240458A1 (fr) |
| AT (1) | ATE47853T1 (fr) |
| AU (1) | AU587811B2 (fr) |
| DD (1) | DD244553A5 (fr) |
| DE (1) | DE3666820D1 (fr) |
| DK (1) | DK172786A (fr) |
| ES (1) | ES8800160A1 (fr) |
| FI (1) | FI861574A7 (fr) |
| GR (1) | GR860998B (fr) |
| HU (1) | HU195498B (fr) |
| IL (1) | IL78528A (fr) |
| NO (1) | NO166080C (fr) |
| NZ (1) | NZ215868A (fr) |
| OA (1) | OA08236A (fr) |
| PH (1) | PH23770A (fr) |
| PT (1) | PT82414B (fr) |
| ZA (1) | ZA862388B (fr) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE58742B1 (en) * | 1984-07-20 | 1993-11-05 | Warner Lambert Co | Substituted-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de] [1,4]benzoxauine-6-carboxylic acids; sibstituted-5-amino-6-6fluoro-4-oxo.1,4-dihydroquinoline-3 carboxylic acids; substituted-5-amino-6-fluoro-1,4-dihydro-4-oxo-1.8-naphthyridine-3-carboxylic acids; derivatives thereof; pharmaceutical compositions comprising the compounds; and processes for producing the compounds |
| EP0207420B1 (fr) * | 1985-06-26 | 1992-05-06 | Daiichi Pharmaceutical Co., Ltd. | Dérivés d'acide pyridonecarboxylique |
| AU594983B2 (en) * | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| EP0242789A3 (fr) * | 1986-04-25 | 1990-09-05 | Dainippon Pharmaceutical Co., Ltd. | Dérivés de quinoléine et procédés pour leur préparation |
| GB8612137D0 (en) * | 1986-05-19 | 1986-06-25 | Fujisawa Pharmaceutical Co | Quinolone compounds |
| FR2607503B1 (fr) * | 1986-12-02 | 1989-02-24 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2607504B1 (fr) * | 1986-12-02 | 1989-01-27 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2607506B1 (fr) * | 1986-12-02 | 1989-01-06 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| DE3711193A1 (de) * | 1987-04-02 | 1988-10-13 | Bayer Ag | 5-substituierte chinolon- und naphthyridoncarbonsaeure-derivate |
| US5290934A (en) * | 1987-04-16 | 1994-03-01 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
| US5563138A (en) * | 1987-04-16 | 1996-10-08 | 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 |
| JPH0794452B2 (ja) * | 1987-10-16 | 1995-10-11 | 大日本製薬株式会社 | 新規ピリドンカルボン酸誘導体、そのエステルおよびその塩 |
| WO1989005643A1 (fr) * | 1987-12-18 | 1989-06-29 | Pfizer Inc. | Acides carboxyliques de quinoline a substitution heterocyclique |
| DE3814517A1 (de) * | 1988-02-05 | 1989-08-17 | Bayer Ag | Chinolon- und naphthyridoncarbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| IL90062A (en) | 1988-04-27 | 1994-10-07 | Daiichi Seiyaku Co | Pyridonecarboxylic acid derivatives, their preparation and pharmaceutical compositions containing them |
| DE3906365A1 (de) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| US4992449A (en) * | 1990-02-01 | 1991-02-12 | American Cyanamid Company | 7-(substituted)cycloalkylamino-1-(substituted)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
| FR2692577B1 (fr) * | 1992-05-26 | 1996-02-02 | Bouchara Sa | Nouvelles quinolones fluorees, leur procede de preparation et les compositions pharmaceutiques en renfermant. |
| ID16655A (id) * | 1996-04-24 | 1997-10-30 | Daiichi Seiyaku Co | Turunan-turunan sikloalkilaminometilpirolidina |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963736A (en) * | 1970-01-28 | 1976-06-15 | Sumitomo Chemical Company, Limited | Preparation of 1-(lower alkyl)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acids |
| US3907808A (en) * | 1971-05-17 | 1975-09-23 | Sterling Drug Inc | 1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives |
| CA1175836A (fr) * | 1977-09-20 | 1984-10-09 | Marcel Pesson | Production de derives de l'acide 1,4- dihydroquinoline-3-carboxylique |
| JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
| SE440354B (sv) * | 1981-02-19 | 1985-07-29 | Kyorin Seiyaku Kk | Kinolinkarboxylsyraderivat |
| ES512969A0 (es) * | 1981-06-11 | 1983-02-16 | Warner Lambert Co | "un procedimiento para preparar sales de compuestos de naftiridina y quinoleina". |
| US4477449A (en) * | 1982-04-19 | 1984-10-16 | Warner-Lambert Company | Certain 1,8-naphthyridine compounds useful as antibacterial agents |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| IE58742B1 (en) * | 1984-07-20 | 1993-11-05 | Warner Lambert Co | Substituted-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de] [1,4]benzoxauine-6-carboxylic acids; sibstituted-5-amino-6-6fluoro-4-oxo.1,4-dihydroquinoline-3 carboxylic acids; substituted-5-amino-6-fluoro-1,4-dihydro-4-oxo-1.8-naphthyridine-3-carboxylic acids; derivatives thereof; pharmaceutical compositions comprising the compounds; and processes for producing the compounds |
| AU4042085A (en) * | 1985-03-27 | 1986-10-02 | Brugnoli, Angelo | Energy system using hydrostatic pressure air compressor |
-
1985
- 1985-04-18 US US06/724,442 patent/US4657913A/en not_active Expired - Fee Related
-
1986
- 1986-04-01 ZA ZA862388A patent/ZA862388B/xx unknown
- 1986-04-03 AU AU55615/86A patent/AU587811B2/en not_active Ceased
- 1986-04-14 FI FI861574A patent/FI861574A7/fi not_active Application Discontinuation
- 1986-04-15 DE DE8686302812T patent/DE3666820D1/de not_active Expired
- 1986-04-15 DD DD86289148A patent/DD244553A5/de not_active IP Right Cessation
- 1986-04-15 AT AT86302812T patent/ATE47853T1/de not_active IP Right Cessation
- 1986-04-15 EP EP86302812A patent/EP0202763B1/fr not_active Expired
- 1986-04-15 GR GR860998A patent/GR860998B/el unknown
- 1986-04-16 DK DK172786A patent/DK172786A/da active IP Right Grant
- 1986-04-16 IL IL78528A patent/IL78528A/xx unknown
- 1986-04-17 JP JP61087237A patent/JPS61243077A/ja active Pending
- 1986-04-17 NO NO861509A patent/NO166080C/no unknown
- 1986-04-17 NZ NZ215868A patent/NZ215868A/xx unknown
- 1986-04-17 AR AR303682A patent/AR240458A1/es active
- 1986-04-17 HU HU861617A patent/HU195498B/hu not_active IP Right Cessation
- 1986-04-17 PT PT82414A patent/PT82414B/pt not_active IP Right Cessation
- 1986-04-17 PH PH33665A patent/PH23770A/en unknown
- 1986-04-17 OA OA58838A patent/OA08236A/xx unknown
- 1986-04-18 ES ES554142A patent/ES8800160A1/es not_active Expired
- 1986-04-18 KR KR1019860002997A patent/KR890005199B1/ko not_active Expired
- 1986-04-18 CN CN86102683A patent/CN1012064B/zh not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO166080C (no) | 1991-05-29 |
| EP0202763B1 (fr) | 1989-11-08 |
| KR860008164A (ko) | 1986-11-12 |
| DK172786D0 (da) | 1986-04-16 |
| AU587811B2 (en) | 1989-08-31 |
| PT82414A (en) | 1986-05-01 |
| FI861574A7 (fi) | 1986-10-19 |
| IL78528A (en) | 1990-09-17 |
| HUT41020A (en) | 1987-03-30 |
| NZ215868A (en) | 1988-08-30 |
| JPS61243077A (ja) | 1986-10-29 |
| ES8800160A1 (es) | 1987-10-16 |
| PT82414B (pt) | 1988-05-27 |
| CN1012064B (zh) | 1991-03-20 |
| NO166080B (no) | 1991-02-18 |
| DE3666820D1 (en) | 1989-12-14 |
| GR860998B (en) | 1986-08-12 |
| AR240458A1 (es) | 1990-04-30 |
| EP0202763A1 (fr) | 1986-11-26 |
| KR890005199B1 (ko) | 1989-12-18 |
| ZA862388B (en) | 1987-11-25 |
| US4657913A (en) | 1987-04-14 |
| OA08236A (en) | 1987-10-30 |
| DK172786A (da) | 1986-10-19 |
| ATE47853T1 (de) | 1989-11-15 |
| AU5561586A (en) | 1986-10-23 |
| HU195498B (en) | 1988-05-30 |
| ES554142A0 (es) | 1987-10-16 |
| PH23770A (en) | 1989-11-03 |
| IL78528A0 (en) | 1986-08-31 |
| NO861509L (no) | 1986-10-20 |
| CN86102683A (zh) | 1986-12-03 |
| FI861574A0 (fi) | 1986-04-14 |
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