DE69421285T2 - Substituierte oxazine und thiazine oxazolidinone als antimikrobielle mittel - Google Patents
Substituierte oxazine und thiazine oxazolidinone als antimikrobielle mittelInfo
- Publication number
- DE69421285T2 DE69421285T2 DE69421285T DE69421285T DE69421285T2 DE 69421285 T2 DE69421285 T2 DE 69421285T2 DE 69421285 T DE69421285 T DE 69421285T DE 69421285 T DE69421285 T DE 69421285T DE 69421285 T2 DE69421285 T2 DE 69421285T2
- Authority
- DE
- Germany
- Prior art keywords
- fluoro
- oxazolidinyl
- phenyl
- oxo
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims description 9
- 239000004599 antimicrobial Substances 0.000 title abstract description 6
- 150000004893 oxazines Chemical class 0.000 title description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- -1 C1-C8alkoxy Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 241000186367 Mycobacterium avium Species 0.000 claims abstract description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 241001148536 Bacteroides sp. Species 0.000 claims abstract description 4
- 241001112696 Clostridia Species 0.000 claims abstract description 4
- 241000186359 Mycobacterium Species 0.000 claims abstract description 4
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims abstract description 4
- 241000295644 Staphylococcaceae Species 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 3
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- FJTGTORNCIBUGT-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(1,3-thiazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CSCC1 FJTGTORNCIBUGT-LBPRGKRZSA-N 0.000 claims description 3
- WNRIDZUNMXATND-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxo-1,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCS(=O)CC1 WNRIDZUNMXATND-ZDUSSCGKSA-N 0.000 claims description 3
- UYMQTPUEEPRWLS-ZDUSSCGKSA-N n-[[(5s)-3-[4-(1,1-dioxo-1,4-thiazinan-4-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCS(=O)(=O)CC1 UYMQTPUEEPRWLS-ZDUSSCGKSA-N 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- FNDDDNOJWPQCBZ-ZDUSSCGKSA-N sutezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCSCC1 FNDDDNOJWPQCBZ-ZDUSSCGKSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- MBVRUJBHHUCNLT-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1COCC1 MBVRUJBHHUCNLT-LBPRGKRZSA-N 0.000 claims description 2
- HOSRDHHVNZJRLI-LBPRGKRZSA-N n-[[(5s)-3-[4-(1,1-dioxo-1,3-thiazolidin-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CS(=O)(=O)CC1 HOSRDHHVNZJRLI-LBPRGKRZSA-N 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- YEXPTKNKQPHGOQ-NSHDSACASA-N 2,2-dichloro-n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C(Cl)Cl)C2)=O)=CC=C1N1CCOCC1 YEXPTKNKQPHGOQ-NSHDSACASA-N 0.000 claims 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- WGIFOQVMODBSBA-LBPRGKRZSA-N n-[[(5s)-3-(3,5-difluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC(F)=C1N1CCOCC1 WGIFOQVMODBSBA-LBPRGKRZSA-N 0.000 claims 1
- KJQHEZGBHYZSKA-LBPRGKRZSA-N n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-hydroxyacetamide Chemical compound O=C1O[C@@H](CNC(=O)CO)CN1C(C=C1F)=CC=C1N1CCOCC1 KJQHEZGBHYZSKA-LBPRGKRZSA-N 0.000 claims 1
- SLSMGQVMFZCVRS-RQXQQJJBSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxothiazepan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CNS(=O)CCC1 SLSMGQVMFZCVRS-RQXQQJJBSA-N 0.000 claims 1
- LKXALCSGNWOQLV-PYMCNQPYSA-N n-[[(5s)-3-[3-fluoro-4-(oxazepan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CNOCCC1 LKXALCSGNWOQLV-PYMCNQPYSA-N 0.000 claims 1
- DPWACSJLQZCNLC-PYMCNQPYSA-N n-[[(5s)-3-[3-fluoro-4-(thiazepan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CNSCCC1 DPWACSJLQZCNLC-PYMCNQPYSA-N 0.000 claims 1
- PZKQAWFQXIHRBC-PYMCNQPYSA-N n-[[(5s)-3-[4-(1,1-dioxothiazepan-4-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CNS(=O)(=O)CCC1 PZKQAWFQXIHRBC-PYMCNQPYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 abstract description 3
- 241001148470 aerobic bacillus Species 0.000 abstract description 3
- 244000052769 pathogen Species 0.000 abstract description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 241000894007 species Species 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 173
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 113
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
- 239000007787 solid Substances 0.000 description 69
- 235000019439 ethyl acetate Nutrition 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 38
- 239000000203 mixture Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- 150000001540 azides Chemical class 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000013058 crude material Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 description 4
- NVZIFMAZKAYQJR-UHFFFAOYSA-N 3-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCN1CCOC1=O NVZIFMAZKAYQJR-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 4
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- 241000699670 Mus sp. Species 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 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
- GEGRWPYIEYMGHO-SNVBAGLBSA-N (5r)-3-[3-fluoro-4-(1,3-thiazolidin-3-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N1CSCC1 GEGRWPYIEYMGHO-SNVBAGLBSA-N 0.000 description 3
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- 239000003054 catalyst Substances 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
- 239000013078 crystal Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
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- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- OQFUNFPIPRUQAE-UHFFFAOYSA-N 1,4-thiazepane Chemical compound C1CNCCSC1 OQFUNFPIPRUQAE-UHFFFAOYSA-N 0.000 description 2
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- 229960003646 lysine Drugs 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
- 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
- 208000004396 mastitis Diseases 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XVWPGZHRCDQQGP-UHFFFAOYSA-N n-[(2-oxo-1,3-oxazolidin-3-yl)methyl]-2-phenylmethoxyacetamide Chemical compound C1COC(=O)N1CNC(=O)COCC1=CC=CC=C1 XVWPGZHRCDQQGP-UHFFFAOYSA-N 0.000 description 1
- DMBCNSZDUQUMNS-JMSDCMLSSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxo-1,3-thiazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CS(=O)CC1 DMBCNSZDUQUMNS-JMSDCMLSSA-N 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
- 238000003305 oral gavage Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000001301 oxygen Substances 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
- 230000035515 penetration Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 210000000952 spleen Anatomy 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl 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
- 238000000967 suction filtration Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository 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
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11927993A | 1993-09-09 | 1993-09-09 | |
| US22615894A | 1994-04-11 | 1994-04-11 | |
| PCT/US1994/008904 WO1995007271A1 (en) | 1993-09-09 | 1994-08-16 | Substituted oxazine and thiazine oxazolidinone antimicrobials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69421285D1 DE69421285D1 (de) | 1999-11-25 |
| DE69421285T2 true DE69421285T2 (de) | 2000-02-24 |
Family
ID=26817181
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69421285T Expired - Lifetime DE69421285T2 (de) | 1993-09-09 | 1994-08-16 | Substituierte oxazine und thiazine oxazolidinone als antimikrobielle mittel |
| DE10299007C Active DE10299007I2 (de) | 1993-09-09 | 1994-08-16 | Substituierte oxazin- und thiazin oxazolidinone als antimikrobielle mittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10299007C Active DE10299007I2 (de) | 1993-09-09 | 1994-08-16 | Substituierte oxazin- und thiazin oxazolidinone als antimikrobielle mittel |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0717738B1 (https=) |
| JP (1) | JP3176630B2 (https=) |
| KR (1) | KR100301269B1 (https=) |
| CN (1) | CN1057087C (https=) |
| AT (1) | ATE185804T1 (https=) |
| AU (1) | AU687866B2 (https=) |
| CA (1) | CA2168560C (https=) |
| DE (2) | DE69421285T2 (https=) |
| DK (1) | DK0717738T3 (https=) |
| ES (1) | ES2139093T3 (https=) |
| GR (1) | GR3031809T3 (https=) |
| IL (1) | IL110802A (https=) |
| LV (1) | LV12605B (https=) |
| MY (1) | MY115155A (https=) |
| NL (1) | NL300079I1 (https=) |
| NZ (1) | NZ271805A (https=) |
| PH (1) | PH31634A (https=) |
| SI (1) | SI0717738T1 (https=) |
| TW (1) | TW293817B (https=) |
| WO (1) | WO1995007271A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| PT792273E (pt) * | 1994-11-15 | 2003-06-30 | Upjohn Co | Produtos antibacterianos de oxazolidinona substituida com oxazina e tiazina biciclicas |
| ATE205205T1 (de) * | 1995-02-03 | 2001-09-15 | Upjohn Co | Durch hetero-aromatische ring substituierte phenyloxazolidinone als antimikrobielles mittel |
| DE69614847T2 (de) * | 1995-05-11 | 2002-04-04 | Pharmacia & Upjohn Co., Kalamazoo | Spirocyclische und bicyclische diazinyl- und carbazinyloxazolidinone |
| DE69631347T2 (de) * | 1995-09-15 | 2004-10-07 | Upjohn Co | Aminoaryl oxazolidinone n-oxide |
| AU6902096A (en) * | 1995-09-15 | 1997-04-01 | Pharmacia & Upjohn Company | 5-amidomethyl alpha, beta-saturated and -unsaturated 3-aryl butyrolactone antibacterial agents |
| GB9521508D0 (en) * | 1995-10-20 | 1995-12-20 | Zeneca Ltd | Chemical compounds |
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| GB9702213D0 (en) * | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| MY116093A (en) * | 1996-02-26 | 2003-11-28 | Upjohn Co | Azolyl piperazinyl phenyl oxazolidinone antimicrobials |
| GB9604301D0 (en) * | 1996-02-29 | 1996-05-01 | Zeneca Ltd | Chemical compounds |
| DK1114819T3 (da) * | 1996-04-11 | 2008-04-14 | Pharmacia & Upjohn Co Llc | Fremgangsmåde til fremstilling af oxazolidinoner |
| GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| DE19709443C1 (de) * | 1997-03-07 | 1998-10-08 | Clariant Gmbh | Verfahren zur Herstellung von N-Carboxyalkyl-3-fluor-4-dialkylaminoanilinen und N-Carboxymethyl-3-fluor-4-morpholinoanilin und N-Carboxyisobutyl-3-fluor-4-morpholinoanilin |
| SK156499A3 (en) * | 1997-05-30 | 2000-06-12 | Upjohn Co | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| US6255304B1 (en) | 1997-05-30 | 2001-07-03 | Pharmacia & Upjohn Company | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| EP1772453A1 (en) * | 1997-11-07 | 2007-04-11 | Pharmacia & Upjohn Company LLC | Process to produce Oxazolidinones |
| GB9725244D0 (en) * | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| US6562844B2 (en) | 1998-01-23 | 2003-05-13 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| BR9907183A (pt) * | 1998-01-23 | 2003-06-10 | Versicor Inc | Colet neas combinatórias de oxazolidinona, composições e processos de preparação |
| US7002020B1 (en) | 1998-01-23 | 2006-02-21 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| JP2002503655A (ja) * | 1998-02-13 | 2002-02-05 | ファルマシア・アンド・アップジョン・カンパニー | 抗菌剤として有用な置換アミノフェニルイソオキサゾリン誘導体 |
| US6288234B1 (en) * | 1998-06-08 | 2001-09-11 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
| AU1379900A (en) * | 1998-11-17 | 2000-06-05 | Bayer Aktiengesellschaft | Novel substituted phenyloxazolidone derivatives |
| HK1040707A1 (zh) * | 1998-11-27 | 2002-06-21 | 法玛西雅厄普约翰美国公司 | 具有硫代羰基官能團的噁唑烷酮抗菌劑 |
| US6413981B1 (en) | 1999-08-12 | 2002-07-02 | Ortho-Mcneil Pharamceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| US6608081B2 (en) | 1999-08-12 | 2003-08-19 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| US6297242B1 (en) | 1999-08-12 | 2001-10-02 | Ortho-Mcneil Pharmaceutical, Inc. | N-substituted amidine and guanidine oxazolidinone antibacterials and methods of use thereof |
| US6518285B2 (en) * | 1999-12-21 | 2003-02-11 | Ortho Mcneil Pharmaceutical, Inc. | Piperidinyloxy and pyrrolidinyloxy oxazolidinone antibacterials |
| SK7572002A3 (en) * | 1999-12-21 | 2002-12-03 | Upjohn Co | Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents |
| KR100355345B1 (ko) * | 2000-01-21 | 2002-10-12 | 한국과학기술연구원 | 티오펜환을 함유한 신규한 옥사졸리디논 유도체, 그의 제조방법 및 조성물 |
| AR027261A1 (es) * | 2000-02-02 | 2003-03-19 | Upjohn Co | Linezolid forma cristalina ii |
| US6642238B2 (en) | 2000-02-10 | 2003-11-04 | Pharmacia And Upjohn Company | Oxazolidinone thioamides with piperazine amide substituents |
| US6562820B2 (en) * | 2000-07-05 | 2003-05-13 | Pharmacia & Upjohn Company | Method for treatment and prevention of mastitis |
| US6638908B1 (en) | 2000-08-09 | 2003-10-28 | Yale University | Crystals of the large ribosomal subunit |
| US6947844B2 (en) | 2000-08-09 | 2005-09-20 | Yale University | Modulators of ribosomal function and identification thereof |
| ES2256318T3 (es) * | 2000-10-17 | 2006-07-16 | PHARMACIA & UPJOHN COMPANY LLC | Metodos de produccion de compuestos de oxazolidinona. |
| YU52403A (sh) * | 2000-12-26 | 2006-03-03 | Dr.Reddy's Research Foundation | Heterociklična jedinjenja koja imaju antibakterijsko dejstvo, postupak za njihovo dobijanje i farmaceutske smeše koje ih sadrže |
| US7160912B2 (en) | 2000-12-26 | 2007-01-09 | Dr.Reddy's Laboratories Ltd. | Heterocyclic compounds having antibacterial activity: process for their preparation and pharmaceutical compositions containing them |
| US6951863B2 (en) | 2001-02-07 | 2005-10-04 | Ortho-Mcneil Pharmaceutical, Inc. | Pyridoarylphenly oxazolidinone antibacterials, and related compositions and methods |
| GB0108764D0 (en) * | 2001-04-07 | 2001-05-30 | Astrazeneca Ab | Chemical compounds |
| GB0108793D0 (en) * | 2001-04-07 | 2001-05-30 | Astrazeneca Ab | Chemical compounds |
| GB0108794D0 (en) * | 2001-04-07 | 2001-05-30 | Astrazeneca Ab | Chemical compound |
| DE60212959T2 (de) * | 2001-04-07 | 2007-02-15 | Astrazeneca Ab | Eine sulfonimid-gruppe enthaltende oxazolidinone als antibiotika |
| JP2004521937A (ja) | 2001-04-20 | 2004-07-22 | ファルマシア・アンド・アップジョン・カンパニー | オキサゾリジノンの製法 |
| ES2186550B2 (es) | 2001-06-27 | 2003-11-16 | Vita Lab | Nuevos derivados de oxazolidinonas como antibacterianos. |
| CA2453182A1 (en) * | 2001-07-10 | 2003-01-23 | Meredith L. Greene | Crystalline thiazine oxazolidinones |
| IL151012A0 (en) | 2001-08-03 | 2003-02-12 | Ribosomes Structure And Protei | Ribosomes structure and protein synthesis inhibitors |
| US6952650B2 (en) | 2001-08-03 | 2005-10-04 | Yale University | Modulators of ribosomal function and identification thereof |
| BR0307103A (pt) * | 2002-01-24 | 2004-12-28 | Upjohn Co | Dihidrotiazina e dihidrotiopirano oxazolidinovas antimicrobianas |
| AR038536A1 (es) | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| US7141588B2 (en) | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| CN1653064A (zh) * | 2002-02-28 | 2005-08-10 | 阿斯特拉曾尼卡有限公司 | 噁唑烷酮衍生物、其制备方法以及包含它们的药用组合物 |
| CN1649866A (zh) | 2002-02-28 | 2005-08-03 | 阿斯特拉曾尼卡有限公司 | 3－环状基－5－(含氮5－元环)甲基－噁唑烷酮衍生物及其作为抗菌药物的用途 |
| AU2003224345A1 (en) * | 2002-04-30 | 2003-11-17 | Orchid Chemicals & Pharmaceuticals | Antibacterial agents |
| DE60304360T2 (de) | 2002-08-12 | 2006-11-16 | Pharmacia & Upjohn Co. Llc, Kalamazoo | N-aryl-2-oxazolidinone und deren derivate |
| WO2004026848A1 (en) * | 2002-09-20 | 2004-04-01 | Lupin Limited | Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents |
| TW200420573A (en) | 2002-09-26 | 2004-10-16 | Rib X Pharmaceuticals Inc | Bifunctional heterocyclic compounds and methods of making and using same |
| US6875784B2 (en) | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
| KR100490643B1 (ko) * | 2002-10-29 | 2005-05-19 | 한국과학기술연구원 | 새로운 메틸리덴 피페리딘일 옥사졸리딘온 유도체 및이들의 제조방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54160371A (en) * | 1978-06-02 | 1979-12-19 | Kyowa Hakko Kogyo Co Ltd | Novel piperidine derivative and hypotensive agents comprising it |
| ES533097A0 (es) * | 1983-06-07 | 1985-08-01 | Du Pont | Un procedimiento para la preparacion de nuevos derivados del amino-metil-oxooxazolidinil-benzeno. |
| CA1260948A (en) * | 1984-12-05 | 1989-09-26 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents |
| US4948801A (en) * | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| EP0610265B1 (en) * | 1991-11-01 | 1996-12-27 | PHARMACIA & UPJOHN COMPANY | Substituted aryl- and heteroarylphenyloxazolidinones useful as antibacterial agents |
| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
-
1994
- 1994-08-13 MY MYPI94002115A patent/MY115155A/en unknown
- 1994-08-16 KR KR1019960701191A patent/KR100301269B1/ko not_active Expired - Lifetime
- 1994-08-16 SI SI9430287T patent/SI0717738T1/xx unknown
- 1994-08-16 TW TW083107479A patent/TW293817B/zh not_active IP Right Cessation
- 1994-08-16 EP EP94925765A patent/EP0717738B1/en not_active Expired - Lifetime
- 1994-08-16 AU AU75570/94A patent/AU687866B2/en not_active Expired
- 1994-08-16 DE DE69421285T patent/DE69421285T2/de not_active Expired - Lifetime
- 1994-08-16 AT AT94925765T patent/ATE185804T1/de active
- 1994-08-16 NZ NZ271805A patent/NZ271805A/en not_active IP Right Cessation
- 1994-08-16 DE DE10299007C patent/DE10299007I2/de active Active
- 1994-08-16 CN CN94193313A patent/CN1057087C/zh not_active Expired - Lifetime
- 1994-08-16 ES ES94925765T patent/ES2139093T3/es not_active Expired - Lifetime
- 1994-08-16 CA CA002168560A patent/CA2168560C/en not_active Expired - Lifetime
- 1994-08-16 JP JP50866595A patent/JP3176630B2/ja not_active Expired - Lifetime
- 1994-08-16 DK DK94925765T patent/DK0717738T3/da active
- 1994-08-16 WO PCT/US1994/008904 patent/WO1995007271A1/en not_active Ceased
- 1994-08-22 PH PH48830A patent/PH31634A/en unknown
- 1994-08-29 IL IL11080294A patent/IL110802A/xx not_active IP Right Cessation
-
1999
- 1999-11-10 GR GR990402902T patent/GR3031809T3/el unknown
-
2000
- 2000-10-20 LV LVP-00-142A patent/LV12605B/en unknown
-
2002
- 2002-01-24 NL NL300079C patent/NL300079I1/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR960704866A (ko) | 1996-10-09 |
| CN1057087C (zh) | 2000-10-04 |
| EP0717738B1 (en) | 1999-10-20 |
| AU687866B2 (en) | 1998-03-05 |
| MY115155A (en) | 2003-04-30 |
| SI0717738T1 (en) | 2000-02-29 |
| DE10299007I1 (de) | 2002-07-04 |
| CA2168560C (en) | 2001-08-14 |
| NZ271805A (en) | 1998-02-26 |
| IL110802A0 (en) | 1994-11-11 |
| NL300079I1 (nl) | 2002-04-02 |
| PH31634A (en) | 1999-01-12 |
| ATE185804T1 (de) | 1999-11-15 |
| AU7557094A (en) | 1995-03-27 |
| CA2168560A1 (en) | 1995-03-16 |
| ES2139093T3 (es) | 2000-02-01 |
| DE10299007I2 (de) | 2008-09-18 |
| CN1130379A (zh) | 1996-09-04 |
| KR100301269B1 (ko) | 2001-10-22 |
| TW293817B (https=) | 1996-12-21 |
| IL110802A (en) | 2000-09-28 |
| DK0717738T3 (da) | 2000-05-08 |
| JP3176630B2 (ja) | 2001-06-18 |
| LV12605A (en) | 2001-01-20 |
| JPH09502436A (ja) | 1997-03-11 |
| GR3031809T3 (en) | 2000-02-29 |
| EP0717738A1 (en) | 1996-06-26 |
| LV12605B (en) | 2001-05-20 |
| WO1995007271A1 (en) | 1995-03-16 |
| DE69421285D1 (de) | 1999-11-25 |
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