DK171276B1 - 1-Substituerede 7-(N-diazabicycloalkyl)-6-fluor-1,4-dihydro-4-oxo-quinolin-3-carboxylsyre-forbindelser, disse forbindelser til anvendelse som lægemidler og antibaktielle præparater indeholdende disse forbindelser - Google Patents

1-Substituerede 7-(N-diazabicycloalkyl)-6-fluor-1,4-dihydro-4-oxo-quinolin-3-carboxylsyre-forbindelser, disse forbindelser til anvendelse som lægemidler og antibaktielle præparater indeholdende disse forbindelser Download PDF

Info

Publication number: DK171276B1
Authority: DK; Denmark
Prior art keywords: compounds; oxo; carboxylic acid; dihydro; diazabicyclo
Prior art date: 1985-09-18

Application number

DK445886A

Other languages

Danish (da)

English (en)

Other versions

DK445886A (da

DK445886D0 (da

Inventor

Martin Raymond Jefson

Paul Robert Mcguirk

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-09-18

Filing date

1986-09-17

Publication date

1996-08-19

1986-09-17 Application filed by Pfizer filed Critical Pfizer

1986-09-17 Publication of DK445886D0 publication Critical patent/DK445886D0/da

1987-05-27 Publication of DK445886A publication Critical patent/DK445886A/da

1996-08-19 Application granted granted Critical

1996-08-19 Publication of DK171276B1 publication Critical patent/DK171276B1/da

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 60
230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 7
239000003814 drug Substances 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 3
229940079593 drug Drugs 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 3
-1 methoxy, N-methylamino, p-fluorophenyl Chemical group 0.000 abstract description 26
229910052739 hydrogen Inorganic materials 0.000 abstract description 9
239000001257 hydrogen Substances 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 5
150000001768 cations Chemical class 0.000 abstract description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
229910052799 carbon Inorganic materials 0.000 abstract 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 abstract 1
125000001188 haloalkyl group Chemical group 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
229920002554 vinyl polymer Chemical group 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 12
239000007787 solid Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000010410 layer Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
239000011734 sodium Substances 0.000 description 5
XJKNACDCUAFDHD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CC2CCN1CCN2 XJKNACDCUAFDHD-UHFFFAOYSA-N 0.000 description 4
MHFJYVWFBPABTI-UHFFFAOYSA-N 1-ethyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHFJYVWFBPABTI-UHFFFAOYSA-N 0.000 description 4
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 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000002923 oximes Chemical class 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 4
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
150000003951 lactams Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
PIDOCGDMKRSJMT-RSLHMRQOSA-N (1s,4s)-2,5-diazabicyclo[2.2.1]heptane;dihydrochloride Chemical compound Cl.Cl.C1N[C@@H]2CN[C@H]1C2 PIDOCGDMKRSJMT-RSLHMRQOSA-N 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
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 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
XNZIHVKLRKGFBS-UHFFFAOYSA-N 8-methyl-3,8-diazabicyclo[3.2.1]octane;dihydrochloride Chemical compound Cl.Cl.C1NCC2CCC1N2C XNZIHVKLRKGFBS-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
229910010084 LiAlH4 Inorganic materials 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
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229920006395 saturated elastomer Polymers 0.000 description 2
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238000000967 suction filtration Methods 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
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CNBHGTBRNNCVMY-UHFFFAOYSA-N 1,2-diazabicyclo[3.2.2]nonane Chemical compound C1CC2CCN1NCC2 CNBHGTBRNNCVMY-UHFFFAOYSA-N 0.000 description 1
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NYPUYWSDUIENGC-UHFFFAOYSA-N 1,4-diazabicyclo[3.3.1]nonane Chemical compound C1N2CCCC1NCC2 NYPUYWSDUIENGC-UHFFFAOYSA-N 0.000 description 1
ZKMZPXWMMSBLNO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2C(=O)CN1CC2 ZKMZPXWMMSBLNO-UHFFFAOYSA-N 0.000 description 1
FOHQYUUKGNBVNW-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-4-oxo-2,3-dihydroquinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)CN1C1CC1 FOHQYUUKGNBVNW-UHFFFAOYSA-N 0.000 description 1
ZNZXELIYKDHAJA-UHFFFAOYSA-N 1-ethyl-6-fluoro-7-(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N2C)CCC2CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(CC)C2=C1 ZNZXELIYKDHAJA-UHFFFAOYSA-N 0.000 description 1
FDTFTAPRLVHJQS-QWRGUYRKSA-N 1-ethyl-6-fluoro-7-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1[C@H](CN2C)C[C@H]2C1 FDTFTAPRLVHJQS-QWRGUYRKSA-N 0.000 description 1
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZZHWFUDVZGOQSF-UHFFFAOYSA-N 4,9-diazabicyclo[4.2.1]nonane Chemical compound C1NCCC2CCC1N2 ZZHWFUDVZGOQSF-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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OXURVGFLFRPDCF-UHFFFAOYSA-N 7-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-1-ethyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN2CCC1CC2 OXURVGFLFRPDCF-UHFFFAOYSA-N 0.000 description 1
AAWPEBWRUYSNEA-UHFFFAOYSA-N 7-(1,4-diazabicyclo[3.3.1]nonan-4-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C2)CCCC2N1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(CC)C2=C1 AAWPEBWRUYSNEA-UHFFFAOYSA-N 0.000 description 1
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
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229910010082 LiAlH Inorganic materials 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
102100035591 POU domain, class 2, transcription factor 2 Human genes 0.000 description 1
101710084411 POU domain, class 2, transcription factor 2 Proteins 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 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
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229960003405 ciprofloxacin Drugs 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WLNWKZXPHXIQKT-UHFFFAOYSA-N cyclohepta-2,6-dien-1-one Chemical compound O=C1C=CCCC=C1 WLNWKZXPHXIQKT-UHFFFAOYSA-N 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical compound OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
229960000210 nalidixic acid Drugs 0.000 description 1
229960001180 norfloxacin Drugs 0.000 description 1
KIMVTSGNCBGHES-UHFFFAOYSA-N octane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCC KIMVTSGNCBGHES-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical class C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 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
- C07D471/08—Bridged systems
- 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
- 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
- C07D487/08—Bridged systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Materials For Photolithography (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DK445886A 1985-09-18 1986-09-17 1-Substituerede 7-(N-diazabicycloalkyl)-6-fluor-1,4-dihydro-4-oxo-quinolin-3-carboxylsyre-forbindelser, disse forbindelser til anvendelse som lægemidler og antibaktielle præparater indeholdende disse forbindelser DK171276B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US77747185A	1985-09-18	1985-09-18
US77747185		1985-09-18

Publications (3)

Publication Number	Publication Date
DK445886D0 DK445886D0 (da)	1986-09-17
DK445886A DK445886A (da)	1987-05-27
DK171276B1 true DK171276B1 (da)	1996-08-19

Family

ID=25110350

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK445886A DK171276B1 (da)	1985-09-18	1986-09-17	1-Substituerede 7-(N-diazabicycloalkyl)-6-fluor-1,4-dihydro-4-oxo-quinolin-3-carboxylsyre-forbindelser, disse forbindelser til anvendelse som lægemidler og antibaktielle præparater indeholdende disse forbindelser

Country Status (42)

Country	Link
US (3)	US4775668A (fr)
EP (1)	EP0215650B1 (fr)
JP (1)	JPH0798819B2 (fr)
KR (1)	KR870000961B1 (fr)
CN (1)	CN1014789B (fr)
AT (1)	ATE72245T1 (fr)
AU (1)	AU576302B2 (fr)
BG (2)	BG49275A3 (fr)
CA (1)	CA1340734C (fr)
CY (1)	CY1774A (fr)
CZ (1)	CZ277825B6 (fr)
DD (1)	DD259190A5 (fr)
DE (2)	DE19675019I2 (fr)
DK (1)	DK171276B1 (fr)
EG (1)	EG18184A (fr)
ES (1)	ES2001428A6 (fr)
FI (1)	FI87565C (fr)
GR (1)	GR862363B (fr)
HK (1)	HK132795A (fr)
HU (1)	HU200462B (fr)
IE (1)	IE58966B1 (fr)
IL (1)	IL80033A (fr)
IN (1)	IN166416B (fr)
LU (1)	LU90356I2 (fr)
MA (1)	MA20770A1 (fr)
MW (1)	MW5886A1 (fr)
MX (1)	MX173358B (fr)
MY (1)	MY102518A (fr)
NO (1)	NO170335C (fr)
NZ (1)	NZ217614A (fr)
OA (1)	OA08410A (fr)
PH (2)	PH24048A (fr)
PL (1)	PL149987B1 (fr)
PT (1)	PT83388B (fr)
SG (1)	SG28094G (fr)
SK (1)	SK667886A3 (fr)
SU (1)	SU1482531A3 (fr)
UA (1)	UA6340A1 (fr)
YU (1)	YU45024B (fr)
ZA (1)	ZA867063B (fr)
ZM (1)	ZM8586A1 (fr)
ZW (1)	ZW19386A1 (fr)

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US4965273A (en) *	1986-10-08	1990-10-23	Bristol-Myers Company	Certain 1-tertiary-butyl-naphthyridone carboxylic acid derivatives anti-bacterial agents
WO1989000158A1 (fr) *	1987-07-02	1989-01-12	Pfizer Inc.	Acides et esters carboxyliques de quinolone de diazabicycloalkyle shunte
US4968799A (en) *	1987-07-31	1990-11-06	Warner-Lambert Company	Antibacterial agents
US4923879A (en) *	1987-07-31	1990-05-08	Warner-Lambert Company	1,8-Naphthyridines and their use as antibacterial agents
US4992546A (en) *	1987-07-31	1991-02-12	Warner-Lambert Company	Process for preparing 6,8-diazabicyclo[3.2.2]nonane derivatives
US4933335A (en) *	1987-08-07	1990-06-12	Warner-Lambert Company	Quinolones as antibacterial agents
WO1989005643A1 (fr) *	1987-12-18	1989-06-29	Pfizer Inc.	Acides carboxyliques de quinoline a substitution heterocyclique
DE3902079A1 (de) *	1988-04-15	1989-10-26	Bayer Ag	I.m. injektionsformen von gyrase-inhibitoren
WO1990002123A1 (fr) *	1988-08-23	1990-03-08	Pfizer Inc.	Acides et esters carboxyliques de quinolones azabicycliques a structure en pont et a substitution amino
US5147873A (en) *	1988-08-23	1992-09-15	Pfizer Inc.	Amino-substituted bridged azabicyclic quinolone carboxylic acids and esters
US4895943A (en) *	1988-10-25	1990-01-23	Pfizer Inc.	Preparation of 1,4-diazabicyclo(3.2.2)nonane
US5036153A (en) *	1989-05-11	1991-07-30	Braish Tamim F	Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates
US5214051A (en) *	1989-08-01	1993-05-25	Pfizer Inc.	Thiazolyl and oxazolyl[5,4-c]piperidyl-substituted quinolone-carboxylic acid and related analogs thereof having antibacterial properties are disclosed
US5013839A (en) *	1989-09-25	1991-05-07	Pfizer Inc.	Process for optically active 2-alkyl-2,5-diazabicyclo(2.2.1) heptanes
US5095121A (en) *	1989-09-25	1992-03-10	Pfizer Inc	Process for optically active 2-alkyl-2,5-diazabicyclo(2.2.1)heptanes
US5157125A (en) *	1989-09-25	1992-10-20	Pfizer Inc.	Optically active 2-alkyl-2,5-diazabicyclo[2.2.1]heptanes
FI921475L (fi) *	1989-10-06	1992-04-03	Pfizer	1,4-dihydro-4-oxo-3-kinolinderivat som selektivt toxiska antibakteriella aemenn hos daeggdjur.
US5385913A (en) *	1989-10-06	1995-01-31	Pfizer Inc.	1,4-dihydro-4-oxo-3-quinoline derivatives as selectively toxic mammalian antibacterial agents
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
US5580872A (en) *	1990-05-02	1996-12-03	Abbott Laboratories	Quinolizinone type compounds
ES2065175T3 (es) *	1991-03-01	1995-02-01	Pfizer	Derivados de 1-azabiciclo(3.2.2)nonan-3-amina.
US5235054A (en) *	1992-07-15	1993-08-10	Pfizer Inc.	3-carboxaldehyde substituted quinolines and naphthyridines
GB2291421A (en) *	1994-07-16	1996-01-24	Pfizer	A process for preparing a quinoline carboxylic acid
ES2092963B1 (es) *	1995-04-12	1997-12-16	Sint Quimica Sa	Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales.
US5929086A (en) *	1996-05-10	1999-07-27	Pharmacia & Upjohn Company	Topical administration of antimicrobial agents for the treatment of systemic bacterial diseases
US6056436A (en) *	1997-02-20	2000-05-02	University Of Maryland	Simultaneous measurement of temperature and strain using optical sensors
US6114531A (en) *	1998-07-28	2000-09-05	Pfizer Inc.	Process for preparing quinolone and naphthyridone carboxylic acids
NZ513575A (en) *	1999-05-04	2003-07-25	Neurosearch As	Heteroaryl diazabicycloalkanes useful for treating or preventing a disease or a disorder responsive to the activity of nAChR modulators
FR2809731B1 (fr) *	2000-05-31	2002-07-19	Sanofi Synthelabo	Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique
FR2809732B1 (fr) *	2000-05-31	2002-07-19	Sanofi Synthelabo	DERIVES DE 4(-2-PHENYLTHIAZOL-5-yl)-1,4-DIAZABICYCLO-[3.2.2] NONANE, LEUR PREPARATION ET LEUR APPLICATION ENTHERAPEUTIQUE
FR2809730B1 (fr) *	2000-05-31	2002-07-19	Sanofi Synthelabo	Derives de 1,4-diazabicyclo[3.2.2] nonanebenzoxazole, -benzothiazole et -benzimidazole, leur preparation et leur application therapeutique
CN1331864C (zh) *	2001-03-02	2007-08-15	神经研究公司	新型2,5－二氮杂二环[2.2.1]庚烷衍生物
WO2004024729A1 (fr) *	2002-09-10	2004-03-25	Pfizer Products Inc.	Composes diazabicycliques utilises dans le traitement de troubles associes au snc
AU2003276919B2 (en) *	2002-09-25	2013-05-16	Memory Pharmaceuticals Corporation	Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof
DE10312346A1 (de) *	2003-03-20	2004-09-30	Bayer Healthcare Ag	Kontrolliertes Freisetzungssystem
DE10351448A1 (de)	2003-11-04	2005-06-09	Bayer Healthcare Ag	Geschmackstoffhaltige Arzneimittelformulierungen mit verbesserten pharmazeutischen Eigenschaften
DE602004010299T2 (de) *	2003-12-22	2008-09-18	Memory Pharmaceuticals Corp.	Indole, 1h-indazole, 1,2-benzisoxazole und 1,2-benzisothiazole und deren herstellung und anwendungen
RU2417225C2 (ru)	2004-03-25	2011-04-27	Мемори Фармасьютиклз Корпорейшн	Индазолы, бензотиазолы, бензоизотиазолы, бензизоксазолы и их получение и применение
JP2007534692A (ja) *	2004-04-22	2007-11-29	メモリー・ファーマシューティカルズ・コーポレイション	インドール、１ｈ−インダゾール、１，２−ベンズイソキサゾール、１，２−ベンゾイソチアゾール、ならびにその調製および使用
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1986
- 1986-08-18 IN IN740/DEL/86A patent/IN166416B/en unknown
- 1986-08-19 US US06/898,458 patent/US4775668A/en not_active Expired - Lifetime
- 1986-08-19 US US06/898,473 patent/US4861779A/en not_active Expired - Lifetime
- 1986-08-28 MW MW58/86A patent/MW5886A1/xx unknown
- 1986-09-03 ZM ZM85/86A patent/ZM8586A1/xx unknown
- 1986-09-12 EP EP86307045A patent/EP0215650B1/fr not_active Expired - Lifetime
- 1986-09-12 AT AT86307045T patent/ATE72245T1/de active
- 1986-09-12 DE DE1996175019 patent/DE19675019I2/de active Active
- 1986-09-12 DE DE8686307045T patent/DE3683711D1/de not_active Expired - Lifetime
- 1986-09-15 IL IL80033A patent/IL80033A/xx not_active IP Right Cessation
- 1986-09-15 EG EG580/86A patent/EG18184A/xx active
- 1986-09-16 ES ES8601935A patent/ES2001428A6/es not_active Expired
- 1986-09-16 PL PL1986261410A patent/PL149987B1/pl unknown
- 1986-09-16 CZ CS866678A patent/CZ277825B6/cs not_active IP Right Cessation
- 1986-09-16 PT PT83388A patent/PT83388B/pt unknown
- 1986-09-16 GR GR862363A patent/GR862363B/el unknown
- 1986-09-16 CA CA000518238A patent/CA1340734C/fr not_active Expired - Lifetime
- 1986-09-16 SK SK6678-86A patent/SK667886A3/sk unknown
- 1986-09-17 ZW ZW193/86A patent/ZW19386A1/xx unknown
- 1986-09-17 DD DD86294486A patent/DD259190A5/de unknown
- 1986-09-17 CN CN86106385A patent/CN1014789B/zh not_active Expired
- 1986-09-17 MX MX003751A patent/MX173358B/es unknown
- 1986-09-17 HU HU863976A patent/HU200462B/hu unknown
- 1986-09-17 KR KR1019860007855A patent/KR870000961B1/ko not_active Expired
- 1986-09-17 IE IE247986A patent/IE58966B1/en not_active IP Right Cessation
- 1986-09-17 UA UA4028142A patent/UA6340A1/uk unknown
- 1986-09-17 DK DK445886A patent/DK171276B1/da not_active IP Right Cessation
- 1986-09-17 NO NO863718A patent/NO170335C/no not_active IP Right Cessation
- 1986-09-17 YU YU1617/86A patent/YU45024B/xx unknown
- 1986-09-17 MA MA20998A patent/MA20770A1/fr unknown
- 1986-09-17 FI FI863756A patent/FI87565C/fi not_active IP Right Cessation
- 1986-09-17 ZA ZA867063A patent/ZA867063B/xx unknown
- 1986-09-17 OA OA58953A patent/OA08410A/fr unknown
- 1986-09-17 SU SU864028142A patent/SU1482531A3/ru active
- 1986-09-17 NZ NZ217614A patent/NZ217614A/xx unknown
- 1986-09-17 AU AU62768/86A patent/AU576302B2/en not_active Expired
- 1986-09-18 BG BG076465A patent/BG49275A3/xx unknown
- 1986-09-18 PH PH34266A patent/PH24048A/en unknown
- 1986-09-18 JP JP61220819A patent/JPH0798819B2/ja not_active Expired - Lifetime
1987
- 1987-08-25 MY MYPI87001447A patent/MY102518A/en unknown
1988
- 1988-02-16 US US07/157,182 patent/US5091383A/en not_active Expired - Fee Related
1989
- 1989-07-11 PH PH38922A patent/PH25338A/en unknown
1992
- 1992-03-17 BG BG096080A patent/BG61091B2/bg unknown
1994
- 1994-02-22 SG SG28094A patent/SG28094G/en unknown
1995
- 1995-08-24 HK HK132795A patent/HK132795A/en not_active IP Right Cessation
- 1995-10-20 CY CY177495A patent/CY1774A/xx unknown
1999
- 1999-02-24 LU LU90356C patent/LU90356I2/fr unknown

Also Published As

Publication number	Publication date
AU6276886A (en)	1987-03-19
PT83388A (en)	1986-10-01
CN1014789B (zh)	1991-11-20
HK132795A (en)	1995-09-01
ZA867063B (en)	1988-04-27
ZW19386A1 (en)	1986-12-10
EP0215650A3 (en)	1987-12-02
MY102518A (en)	1992-07-31
NO170335B (no)	1992-06-29
DD259190A5 (de)	1988-08-17
US4775668A (en)	1988-10-04
PL261410A1 (en)	1987-11-16
YU161786A (en)	1987-10-31
IL80033A (en)	1992-05-25
CA1340734C (fr)	1999-09-14
SG28094G (en)	1994-10-28
YU45024B (en)	1991-06-30
EP0215650B1 (fr)	1992-01-29
GR862363B (en)	1987-01-19
DE19675019I2 (de)	2004-01-29
IN166416B (fr)	1990-05-05
DE3683711D1 (de)	1992-03-12
HUT43070A (en)	1987-09-28
US4861779A (en)	1989-08-29
NZ217614A (en)	1989-11-28
LU90356I2 (fr)	1999-04-26
MW5886A1 (en)	1987-12-09
NO863718L (no)	1987-03-19
EG18184A (en)	1992-12-30
FI863756A0 (fi)	1986-09-17
JPH0798819B2 (ja)	1995-10-25
MX3751A (es)	1993-09-01
HU200462B (en)	1990-06-28
MA20770A1 (fr)	1987-04-01
FI87565B (fi)	1992-10-15
UA6340A1 (uk)	1994-12-29
SK278605B6 (en)	1997-11-05
FI87565C (fi)	1993-01-25
SU1482531A3 (ru)	1989-05-23
DK445886A (da)	1987-05-27
BG61091B2 (bg)	1996-10-31
ZM8586A1 (en)	1987-03-27
SK667886A3 (en)	1997-11-05
CZ277825B6 (en)	1993-06-16
KR870003106A (ko)	1987-04-15
IE862479L (en)	1987-03-18
CY1774A (en)	1995-10-20
ATE72245T1 (de)	1992-02-15
NO863718D0 (no)	1986-09-17
CN86106385A (zh)	1987-06-03
NO170335C (no)	1992-10-07
PH25338A (en)	1991-04-30
DK445886D0 (da)	1986-09-17
KR870000961B1 (ko)	1987-05-14
ES2001428A6 (es)	1988-05-16
IE58966B1 (en)	1993-12-01
IL80033A0 (en)	1986-12-31
PH24048A (en)	1990-03-05
PT83388B (pt)	1989-05-12
OA08410A (fr)	1988-06-30
PL149987B1 (en)	1990-04-30
US5091383A (en)	1992-02-25
MX173358B (es)	1994-02-23
BG49275A3 (en)	1991-09-16
EP0215650A2 (fr)	1987-03-25
AU576302B2 (en)	1988-08-18
JPS62103083A (ja)	1987-05-13
FI863756L (fi)	1987-03-19
CZ667886A3 (en)	1993-02-17

Legal Events

Date	Code	Title	Description
2006-10-02	PUP	Patent expired

Publication	Publication Date	Title
US5091383A (en)	1992-02-25	Substituted bridged diazabicycloalkyl quinolone carboxylic acids
US4571396A (en)	1986-02-18	Antibacterial agents
JP4790703B2 (ja)	2011-10-12	環式化合物
US5434161A (en)	1995-07-18	Imidazopyridines as serotonergic 5-HT3 antagonists
US8236793B2 (en)	2012-08-07	Diazabicyclic aryl derivatives as cholinergic receptor modulators
EP1177196B1 (fr)	2004-03-10	Diazabicycloalcanes heteroaryles, leur preparation et leur utilisation
US5091384A (en)	1992-02-25	Anti-bacterial quinolone- and naphthyridone-carboxylic acid compounds
JPH05213947A (ja)	1993-08-24	７−アザイソインドリニル−キノロン−及びナフチリドンカルボン酸誘導体
EP0655451B1 (fr)	2001-06-20	Composés hétérocycliques condensés tétracycliques, pour le traitement de la démence sénile
CZ297938B6 (cs)	2007-05-02	Derivát indol-2,3-dion-3-oximu, zpusob jeho prípravy a farmaceutická kompozice ho obsahující
NO178149B (no)	1995-10-23	Analogifremgangsmåte for fremstilling av terapeutisk aktive 7-tetrahydro-naftyridin-6-fluor-1,4-dihydro-4-okso-kinolin-3-karboksylsyrer
WO2006051410A1 (fr)	2006-05-18	Azabenzoxazoles pour le traitement de troubles du systeme nerveux central
SK123895A3 (en)	1996-06-05	Derivatives of quinolone carboxylic and naphtyridone carboxylic acid, manufacturing process thereof, drugs containing same and their use
EP3597642A1 (fr)	2020-01-22	Dérivés pharmaceutiques de noyau hétérobicyclique 6,5
IE61370B1 (en)	1994-11-02	Amino-substituted bridged azabicyclic quinolone carboxylic acids and esters
IE19970856A1 (en)	2000-02-23	7-(1-Pyrrolidinyl)-3-quinolone and naphthyridone carboxylic acid derivatives, method for their preparation and for substituted mono- and bicyclic pyrrolidine intermediates, and their antibacterial and feed additive compositions