TW426683B - Oxazolidinone antibacterial agent with tricyclic substituents - Google Patents

Oxazolidinone antibacterial agent with tricyclic substituents Download PDF

Info

Publication number: TW426683B
Authority: TW; Taiwan
Prior art keywords: methyl; oxo; patent application; mmol; page
Prior art date: 1995-11-17

Application number

TW085114048A

Other languages

English (en)

Chinese (zh)

Inventor

Richard C Thomas

Gary J Cleek

Douglas K Hutchinson

Hiroyoshi Yamada

Original Assignee

Pharmacia & Amp Upjohn Company

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.)

1995-11-17

Filing date

1996-11-15

Publication date

2001-03-21

1996-11-15 Application filed by Pharmacia & Amp Upjohn Company filed Critical Pharmacia & Amp Upjohn Company

2001-03-21 Application granted granted Critical

2001-03-21 Publication of TW426683B publication Critical patent/TW426683B/zh

Links

IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 9
239000003242 anti bacterial agent Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 75
150000003839 salts Chemical class 0.000 claims abstract description 16
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
239000004599 antimicrobial Substances 0.000 claims abstract description 7
-1 hydroxyethylfluorenyl Chemical group 0.000 claims description 102
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 80
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 46
238000011049 filling Methods 0.000 claims description 44
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 38
238000002360 preparation method Methods 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
229910001868 water Inorganic materials 0.000 claims description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 23
238000000034 method Methods 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
230000002079 cooperative effect Effects 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 15
239000000741 silica gel Substances 0.000 claims description 15
229910002027 silica gel Inorganic materials 0.000 claims description 15
239000012267 brine Substances 0.000 claims description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
239000012141 concentrate Substances 0.000 claims description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
239000011261 inert gas Substances 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 11
239000007789 gas Substances 0.000 claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
239000000243 solution Substances 0.000 claims description 11
101150041968 CDC13 gene Proteins 0.000 claims description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 10
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
239000007791 liquid phase Substances 0.000 claims description 9
239000012044 organic layer Substances 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
230000008018 melting Effects 0.000 claims description 8
238000002844 melting Methods 0.000 claims description 8
125000002971 oxazolyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
238000012937 correction Methods 0.000 claims description 7
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000000160 oxazolidinyl group Chemical group 0.000 claims description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
238000005481 NMR spectroscopy Methods 0.000 claims description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 6
230000000845 anti-microbial effect Effects 0.000 claims description 6
125000005605 benzo group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
229910000104 sodium hydride Inorganic materials 0.000 claims description 6
239000012312 sodium hydride Substances 0.000 claims description 6
229910052722 tritium Inorganic materials 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 5
FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 5
239000005711 Benzoic acid Substances 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
238000004587 chromatography analysis Methods 0.000 claims description 5
239000010410 layer Substances 0.000 claims description 5
150000004702 methyl esters Chemical class 0.000 claims description 5
235000015170 shellfish Nutrition 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 claims description 4
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
235000019441 ethanol Nutrition 0.000 claims description 4
235000012054 meals Nutrition 0.000 claims description 4
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
238000003756 stirring Methods 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
108010010803 Gelatin Proteins 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000005909 Kieselgur Substances 0.000 claims description 3
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 claims description 3
239000000443 aerosol Substances 0.000 claims description 3
230000008859 change Effects 0.000 claims description 3
239000008273 gelatin Substances 0.000 claims description 3
229920000159 gelatin Polymers 0.000 claims description 3
235000019322 gelatine Nutrition 0.000 claims description 3
235000011852 gelatine desserts Nutrition 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
208000015181 infectious disease Diseases 0.000 claims description 3
239000012074 organic phase Substances 0.000 claims description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
230000002441 reversible effect Effects 0.000 claims description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
239000002689 soil Substances 0.000 claims description 3
GRZHHTYDZVRPIC-UHFFFAOYSA-N (benzyloxy)acetic acid Chemical compound OC(=O)COCC1=CC=CC=C1 GRZHHTYDZVRPIC-UHFFFAOYSA-N 0.000 claims description 2
238000005160 1H NMR spectroscopy Methods 0.000 claims description 2
ZNKHURCEXVMNMH-UHFFFAOYSA-N 2-phenylmethoxyethanimidamide Chemical compound NC(=N)COCC1=CC=CC=C1 ZNKHURCEXVMNMH-UHFFFAOYSA-N 0.000 claims description 2
CTCRKZWVAYSSAF-UHFFFAOYSA-N C(C)(=O)Cl.C(C)(=N)N Chemical compound C(C)(=O)Cl.C(C)(=N)N CTCRKZWVAYSSAF-UHFFFAOYSA-N 0.000 claims description 2
PGONDLCQEMLZBJ-UHFFFAOYSA-L C([O-])([O-])=O.[Os+4].[Na+] Chemical compound C([O-])([O-])=O.[Os+4].[Na+] PGONDLCQEMLZBJ-UHFFFAOYSA-L 0.000 claims description 2
241001674048 Phthiraptera Species 0.000 claims description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
239000012298 atmosphere Substances 0.000 claims description 2
229940007550 benzyl acetate Drugs 0.000 claims description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims description 2
230000037396 body weight Effects 0.000 claims description 2
239000006229 carbon black Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
239000009519 fu-yuan Substances 0.000 claims description 2
230000000813 microbial effect Effects 0.000 claims description 2
239000002480 mineral oil Substances 0.000 claims description 2
235000010446 mineral oil Nutrition 0.000 claims description 2
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical group [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 claims description 2
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
238000004088 simulation Methods 0.000 claims description 2
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
239000011780 sodium chloride Substances 0.000 claims description 2
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims description 2
239000000052 vinegar Substances 0.000 claims description 2
235000021419 vinegar Nutrition 0.000 claims description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
239000000284 extract Substances 0.000 claims 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims 1
TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims 1
229960001173 oxybenzone Drugs 0.000 claims 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 abstract description 11
241001112696 Clostridia Species 0.000 abstract description 5
244000052769 pathogen Species 0.000 abstract description 5
241000606125 Bacteroides Species 0.000 abstract description 4
241000186367 Mycobacterium avium Species 0.000 abstract description 4
241000295644 Staphylococcaceae Species 0.000 abstract description 4
239000000126 substance Substances 0.000 abstract description 4
241001148470 aerobic bacillus Species 0.000 abstract description 2
239000002904 solvent Substances 0.000 description 18
125000004432 carbon atom Chemical group C* 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
239000002585 base Substances 0.000 description 10
230000000875 corresponding effect Effects 0.000 description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
239000011593 sulfur Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
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238000004364 calculation method Methods 0.000 description 6
239000003814 drug Substances 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
150000001540 azides Chemical class 0.000 description 5
239000012071 phase Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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229910052736 halogen Inorganic materials 0.000 description 4
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125000000623 heterocyclic group Chemical group 0.000 description 4
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
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BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
125000001072 heteroaryl group Chemical group 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
DOWJXOHBNXRUOD-UHFFFAOYSA-N methylphenanthrene Natural products C1=CC2=CC=CC=C2C2=C1C(C)=CC=C2 DOWJXOHBNXRUOD-UHFFFAOYSA-N 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
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125000004354 sulfur functional group Chemical group 0.000 description 3
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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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000001514 detection method Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000008393 encapsulating agent Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000011981 lindlar catalyst Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant 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
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940049920 malate Drugs 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
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical group C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000001717 pathogenic effect Effects 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
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
PRAYXGYYVXRDDW-UHFFFAOYSA-N piperidin-2-ylmethanol Chemical compound OCC1CCCCN1 PRAYXGYYVXRDDW-UHFFFAOYSA-N 0.000 description 1
229960004526 piracetam Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
239000011677 pyridoxine Substances 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000008452 qiyu Substances 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
JSMUIAGOLVNWBE-UHFFFAOYSA-N sulfanyl benzoate Chemical compound SOC(=O)C1=CC=CC=C1 JSMUIAGOLVNWBE-UHFFFAOYSA-N 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229940011671 vitamin b6 Drugs 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

TW085114048A 1995-11-17 1996-11-15 Oxazolidinone antibacterial agent with tricyclic substituents TW426683B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US737195P	1995-11-17	1995-11-17

Publications (1)

Publication Number	Publication Date
TW426683B true TW426683B (en)	2001-03-21

Family

ID=21725778

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW085114048A TW426683B (en)	1995-11-17	1996-11-15	Oxazolidinone antibacterial agent with tricyclic substituents

Country Status (12)

Country	Link
US (2)	US5922707A (2)
EP (1)	EP0874852B1 (2)
JP (1)	JP2000500489A (2)
AT (1)	ATE263172T1 (2)
AU (1)	AU7665196A (2)
DE (1)	DE69632074T2 (2)
DK (1)	DK0874852T3 (2)
ES (1)	ES2217329T3 (2)
PT (1)	PT874852E (2)
TW (1)	TW426683B (2)
WO (1)	WO1997019089A1 (2)
ZA (1)	ZA968661B (2)

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ZA968661B (en) *	1995-11-17	1998-04-14	Upjohn Co	Oxazolidinone antibacterial agent with tricyclic substituents.
GB9601666D0 (en) *	1996-01-27	1996-03-27	Zeneca Ltd	Chemical compounds
GB9702213D0 (en)	1996-02-24	1997-03-26	Zeneca Ltd	Chemical compounds
GB9609919D0 (en)	1996-05-11	1996-07-17	Zeneca Ltd	Chemical compounds
AU8457298A (en) *	1997-08-15	1999-03-08	Pfizer Products Inc.	2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1H-indole derivatives interacting with the dopamine D4 receptor
GB9717804D0 (en)	1997-08-22	1997-10-29	Zeneca Ltd	Chemical compounds
GB9717807D0 (en)	1997-08-22	1997-10-29	Zeneca Ltd	Chemical compounds
GB9725244D0 (en)	1997-11-29	1998-01-28	Zeneca Ltd	Chemical compounds
DE19802239A1 (de) *	1998-01-22	1999-07-29	Bayer Ag	Neue mit Bicyclen substituierte Oxazolidinone
DE19802235A1 (de) *	1998-01-22	1999-07-29	Bayer Ag	Mit tricyclischen Indolen substituierte Oxazolidinone
US7002020B1 (en)	1998-01-23	2006-02-21	Pharmacia & Upjohn Company	Oxazolidinone combinatorial libraries, compositions and methods of preparation
US6562844B2 (en)	1998-01-23	2003-05-13	Pharmacia & Upjohn Company	Oxazolidinone combinatorial libraries, compositions and methods of preparation
WO1999037630A1 (en)	1998-01-23	1999-07-29	Versicor, Inc.	Oxazolidinone combinatorial libraries, compositions and methods of preparation
DE19805117A1 (de) *	1998-02-09	1999-08-12	Bayer Ag	Neue Oxazolidinone mit azolhaltigen Tricyclen
KR20010052615A (ko)	1998-06-05	2001-06-25	다비드 에 질레스	옥사졸리디논 유도체, 이것의 제조 방법 및 이것을함유하는 약학 조성물
MY122454A (en) *	1998-06-05	2006-04-29	Upjohn Co	Use of oxazolidinones for the preparation of a medicament for transdermal delivery
PL346795A1 (en)	1998-09-22	2002-02-25	Yamanouchi Pharma Co Ltd	Cyanophenyl derivatives
EP1147422A1 (en)	1999-01-27	2001-10-24	Pharmacia & Upjohn Company	Assays for modulators of "elongation factor p" activity
JP2003501351A (ja) *	1999-05-27	2003-01-14	ファルマシア・アンド・アップジョン・カンパニー	抗菌剤としての二環系オキサゾリジノン
GB9928568D0 (en)	1999-12-03	2000-02-02	Zeneca Ltd	Chemical compounds
GB0009803D0 (en) *	2000-04-25	2000-06-07	Astrazeneca Ab	Chemical compounds
WO2004014897A1 (en)	2002-08-12	2004-02-19	Pharmacia & Upjohn Company Llc	N-aryl-2-oxazolidinones and their derivatives
WO2004045616A1 (en)	2002-11-21	2004-06-03	Pharmacia & Upjohn Company Llc	N-(4-(piperazin-1-yl)-phenyl-2-oxazolidinone-5-carboxamide derivates and related compounds as antibacterial agents
EP1594865A2 (en) *	2003-02-07	2005-11-16	Warner-Lambert Company LLC	Antibacterial agents
EP1661898A4 (en) *	2003-08-29	2009-04-15	Takeda Pharmaceutical	BICYCLIC PIPERAZINE COMPOUND AND ITS USE
AR057828A1 (es) *	2005-09-29	2007-12-19	Astrazeneca Ab	Compuestos derivados de azetidina, su preparacion y composicion farmaceuutica
WO2007087250A2 (en) *	2006-01-23	2007-08-02	Amira Pharmaceuticals, Inc.	Tricyclic inhibitors of 5-lipoxygenase
CN113603707B (zh) *	2016-12-12	2023-03-31	石药集团中奇制药技术（石家庄）有限公司	一类含有三环杂芳基的化合物
CN114644634B (zh) *	2020-12-21	2023-06-20	深圳市祥根生物医药有限公司	一种吡咯衍生物及其制备方法和用途

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US4080499A (en) *	1976-12-20	1978-03-21	1	Substituted 7,8-dihydro-6H-(1,2,5)thiadiazolo(3',4'-5,6)pyrazino(2,3-b)(1,4)oxazines
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BR9509673A (pt) *	1994-11-15	1997-09-30	Upjohn Co	Compostos e uso dos mesmos
ZA968661B (en) *	1995-11-17	1998-04-14	Upjohn Co	Oxazolidinone antibacterial agent with tricyclic substituents.

1996
- 1996-10-14 ZA ZA9608661A patent/ZA968661B/xx unknown
- 1996-11-05 ES ES96939496T patent/ES2217329T3/es not_active Expired - Lifetime
- 1996-11-05 AU AU76651/96A patent/AU7665196A/en not_active Abandoned
- 1996-11-05 EP EP96939496A patent/EP0874852B1/en not_active Expired - Lifetime
- 1996-11-05 WO PCT/US1996/017120 patent/WO1997019089A1/en not_active Ceased
- 1996-11-05 DK DK96939496T patent/DK0874852T3/da active
- 1996-11-05 PT PT96939496T patent/PT874852E/pt unknown
- 1996-11-05 DE DE69632074T patent/DE69632074T2/de not_active Expired - Fee Related
- 1996-11-05 AT AT96939496T patent/ATE263172T1/de not_active IP Right Cessation
- 1996-11-05 JP JP9519726A patent/JP2000500489A/ja not_active Withdrawn
- 1996-11-15 TW TW085114048A patent/TW426683B/zh not_active IP Right Cessation
1997
- 1997-05-02 US US08/850,424 patent/US5922707A/en not_active Expired - Fee Related
1999
- 1999-02-15 US US09/250,382 patent/US5955460A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0874852B1 (en)	2004-03-31
ZA968661B (en)	1998-04-14
JP2000500489A (ja)	2000-01-18
EP0874852A1 (en)	1998-11-04
WO1997019089A1 (en)	1997-05-29
PT874852E (pt)	2004-08-31
DE69632074T2 (de)	2005-01-20
US5922707A (en)	1999-07-13
DK0874852T3 (da)	2004-06-07
US5955460A (en)	1999-09-21
DE69632074D1 (de)	2004-05-06
ATE263172T1 (de)	2004-04-15
ES2217329T3 (es)	2004-11-01
AU7665196A (en)	1997-06-11

Legal Events

Date	Code	Title	Description
2001-08-03	GD4A	Issue of patent certificate for granted invention patent
2006-04-01	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
US5955460A (en)	1999-09-21	Oxazolidinone antibacterial agent with tricyclic substituents
DE69829846T2 (de)	2006-02-23	Antibakteriell wirksam oxazolidinone mit einer thiocarbonylfunktionalität
DE69914478T2 (de)	2004-11-11	Oxazolidinon-derivate als antibiotika, verfahren zu ihrer herstellung und diese derivate enthaltende pharmazeutische zusammensetzungen
CA2122571C (en)	2005-04-12	Adhesion receptor antagonists
JP3628329B2 (ja)	2005-03-09	オキサゾリジノン誘導体及びこれを有効成分とする医薬組成物
US5668286A (en)	1997-09-16	Oxazolidinone derivatives and pharmaceutical compositions containing them
DE69723104T2 (de)	2004-04-29	Piridin-2-yl-methylamin-derivate, verfahren zu deren herstellung und ihre verwendung als arzneimittel
DE60103754T2 (de)	2005-06-16	Oxazolidinonderivate mit antibiotischer aktivität
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