NO317291B1 - Oksazolidinonderivater og farmasoytiske preparater - Google Patents

Oksazolidinonderivater og farmasoytiske preparater Download PDF

Info

Publication number: NO317291B1
Authority: NO; Norway
Prior art keywords: oxo; mixture; methyl; formula; compound
Prior art date: 1997-11-12

Application number

NO20002434A

Other languages

English (en)

Norwegian (no)

Other versions

NO20002434D0 (no

NO20002434L (no

Inventor

Jr Jackson B Hester

Original Assignee

Pharmacia & Upjohn Co Llc

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.)

1997-11-12

Filing date

2000-05-11

Publication date

2004-10-04

2000-05-11 Application filed by Pharmacia & Upjohn Co Llc filed Critical Pharmacia & Upjohn Co Llc

2000-05-11 Publication of NO20002434D0 publication Critical patent/NO20002434D0/no

2000-05-11 Publication of NO20002434L publication Critical patent/NO20002434L/no

2004-10-04 Publication of NO317291B1 publication Critical patent/NO317291B1/no

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 58
150000003839 salts Chemical class 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 9
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
230000000813 microbial effect Effects 0.000 claims description 2
IEEKDTALXZSEBL-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-(5-oxo-1,4-diazepan-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCC(=O)NCC1 IEEKDTALXZSEBL-ZDUSSCGKSA-N 0.000 claims description 2
TUROGGJOBCYLHI-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-methyl-5-oxo-1,4-diazepan-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(=O)N(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F TUROGGJOBCYLHI-AWEZNQCLSA-N 0.000 claims 1
URLVUWSNWKCFCU-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-methyl-5-oxo-1,4-diazepan-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound C1CC(=O)N(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=S)C2)=O)C=C1F URLVUWSNWKCFCU-AWEZNQCLSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
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 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
238000002360 preparation method Methods 0.000 description 18
239000002904 solvent Substances 0.000 description 17
239000012267 brine Substances 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
239000011734 sodium Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000004599 antimicrobial Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000000908 ammonium hydroxide Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000012258 stirred mixture Substances 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 5
ONMOULMPIIOVTQ-UHFFFAOYSA-M 3-Nitrobenzene sulphonate Chemical compound [O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-M 0.000 description 4
241000186367 Mycobacterium avium Species 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241000606768 Haemophilus influenzae Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000588655 Moraxella catarrhalis Species 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000008272 agar Substances 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
KCOPWUJJPSTRIZ-UHFFFAOYSA-N ethyl ethanedithioate Chemical compound CCSC(C)=S KCOPWUJJPSTRIZ-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
-1 oxazolidinone compound Chemical class 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
230000002265 prevention Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000001974 tryptic soy broth Substances 0.000 description 3
108010050327 trypticase-soy broth Proteins 0.000 description 3
NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 description 2
241000606125 Bacteroides Species 0.000 description 2
241001112696 Clostridia Species 0.000 description 2
208000035473 Communicable disease Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000006241 alcohol protecting group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
244000037640 animal pathogen Species 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
JOTXKOXGEZBEEM-UHFFFAOYSA-N azanium;dichloromethane;hydroxide Chemical compound [NH4+].[OH-].ClCCl JOTXKOXGEZBEEM-UHFFFAOYSA-N 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000036765 blood level Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000006285 cell suspension Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
244000052637 human pathogen Species 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000002609 medium Substances 0.000 description 2
UWAHVVNOMMENRW-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-oxopiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=O)CC1 UWAHVVNOMMENRW-AWEZNQCLSA-N 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
WRSMQTCQORNRLX-LBPRGKRZSA-N (5s)-5-(aminomethyl)-3-[3-fluoro-4-(4-methyl-5-oxo-1,4-diazepan-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound C1CC(=O)N(C)CCN1C1=CC=C(N2C(O[C@@H](CN)C2)=O)C=C1F WRSMQTCQORNRLX-LBPRGKRZSA-N 0.000 description 1
XGIDKHVCCPKVKK-NSHDSACASA-N (5s)-5-(aminomethyl)-3-[3-fluoro-4-(5-oxo-1,4-diazepan-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CN)CN1C(C=C1F)=CC=C1N1CCC(=O)NCC1 XGIDKHVCCPKVKK-NSHDSACASA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 1
QPPLBCQXWDBQFS-UHFFFAOYSA-N 1,4-diazepan-5-one Chemical group O=C1CCNCCN1 QPPLBCQXWDBQFS-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
HBNIOTNXXWJMJK-ZDUSSCGKSA-N 8-[2-fluoro-4-[(5s)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-8-azaspiro[4.5]decane-1,4-dione Chemical compound O=C1O[C@H](CO)CN1C(C=C1F)=CC=C1N1CCC2(C(CCC2=O)=O)CC1 HBNIOTNXXWJMJK-ZDUSSCGKSA-N 0.000 description 1
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 1
DXSVIVLMRAWPIM-UHFFFAOYSA-N 8-azaspiro[4.5]decane-1,4-dione Chemical compound O=C1CCC(=O)C11CCNCC1 DXSVIVLMRAWPIM-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000012988 Dithioester Substances 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-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
238000005481 NMR spectroscopy Methods 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
FPWNQPQTICPCOM-UHFFFAOYSA-N acetonitrile;propan-2-ol Chemical compound CC#N.CC(C)O FPWNQPQTICPCOM-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
150000004891 diazines Chemical class 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000005022 dithioester group Chemical group 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000008393 encapsulating agent Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000000499 gel Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
JYGYEBCBALMPDC-UHFFFAOYSA-N heptane;propan-2-one Chemical compound CC(C)=O.CCCCCCC JYGYEBCBALMPDC-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
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
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 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
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UCYYNBWREITJRJ-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-hydroxyiminopiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=NO)CC1 UCYYNBWREITJRJ-AWEZNQCLSA-N 0.000 description 1
KTLHCJNSFNSLOZ-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-(5-oxo-1,4-diazepan-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(=O)NCC1 KTLHCJNSFNSLOZ-ZDUSSCGKSA-N 0.000 description 1
DVHNGZMRRRNHJG-HNNXBMFYSA-N n-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-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=C1N1CCC2(OCCO2)CC1 DVHNGZMRRRNHJG-HNNXBMFYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 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
239000008177 pharmaceutical agent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase 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
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical class O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 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
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 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
239000007909 solid dosage form Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 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
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 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
239000012808 vapor phase Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- 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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

NO20002434A 1997-11-12 2000-05-11 Oksazolidinonderivater og farmasoytiske preparater NO317291B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US6537697P	1997-11-12	1997-11-12
PCT/US1998/022639 WO1999024428A1 (en)	1997-11-12	1998-10-30	Oxazolidinone derivatives and pharmaceutical compositions

Publications (3)

Publication Number	Publication Date
NO20002434D0 NO20002434D0 (no)	2000-05-11
NO20002434L NO20002434L (no)	2000-05-11
NO317291B1 true NO317291B1 (no)	2004-10-04

Family

ID=22062294

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20002434A NO317291B1 (no)	1997-11-12	2000-05-11	Oksazolidinonderivater og farmasoytiske preparater

Country Status (22)

Country	Link
US (1)	US5998406A (sk)
EP (1)	EP1030852B1 (sk)
JP (1)	JP2001522849A (sk)
KR (1)	KR20010031953A (sk)
CN (1)	CN1154644C (sk)
AT (1)	ATE250054T1 (sk)
AU (1)	AU739055B2 (sk)
BR (1)	BR9813985A (sk)
CA (1)	CA2303959A1 (sk)
DE (1)	DE69818294T2 (sk)
DK (1)	DK1030852T3 (sk)
ES (1)	ES2207010T3 (sk)
HK (1)	HK1030373A1 (sk)
HU (1)	HUP0100470A3 (sk)
IL (1)	IL136062A (sk)
NO (1)	NO317291B1 (sk)
NZ (1)	NZ504503A (sk)
PT (1)	PT1030852E (sk)
RU (1)	RU2215740C2 (sk)
SK (1)	SK284577B6 (sk)
TR (1)	TR200001330T2 (sk)
WO (1)	WO1999024428A1 (sk)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1311787A (zh)	1998-06-05	2001-09-05	阿斯特拉曾尼卡有限公司	噁唑烷酮衍生物、其制备方法以及含有它们的药物组合物
DE19962924A1 (de)	1999-12-24	2001-07-05	Bayer Ag	Substituierte Oxazolidinone und ihre Verwendung
KR100355345B1 (ko) *	2000-01-21	2002-10-12	한국과학기술연구원	티오펜환을 함유한 신규한 옥사졸리디논 유도체, 그의 제조방법 및 조성물
DE10129725A1 (de)	2001-06-20	2003-01-02	Bayer Ag	Kombinationstherapie substituierter Oxazolidinone
CA2491287A1 (en)	2002-08-12	2004-02-19	Pharmacia & Upjohn Company	N-aryl-2-oxazolidinones and their derivatives
DE10300111A1 (de) *	2003-01-07	2004-07-15	Bayer Healthcare Ag	Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid
CA2536480A1 (en) *	2003-08-25	2005-03-03	Warner-Lambert Company Llc	Novel antimicrobial aryloxazolidinone compounds
DE10355461A1 (de)	2003-11-27	2005-06-23	Bayer Healthcare Ag	Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung
KR100854211B1 (ko) *	2003-12-18	2008-08-26	동아제약주식회사	신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물
JP2008521792A (ja) *	2004-11-29	2008-06-26	ファルマシア・アンド・アップジョン・カンパニー・エルエルシー	抗菌薬としてのジアゼピンオキサゾリジノン
DE102004062475A1 (de) *	2004-12-24	2006-07-06	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung
EP1685841A1 (en) *	2005-01-31	2006-08-02	Bayer Health Care Aktiengesellschaft	Prevention and treatment of thromboembolic disorders
WO2007000644A1 (en)	2005-06-29	2007-01-04	Pharmacia & Upjohn Company Llc	Homomorpholine oxazolidinones as antibacterial agents
DE102005045518A1 (de) *	2005-09-23	2007-03-29	Bayer Healthcare Ag	2-Aminoethoxyessigsäure-Derivate und ihre Verwendung
DE102005047558A1 (de) *	2005-10-04	2008-02-07	Bayer Healthcare Ag	Kombinationstherapie substituierter Oxazolidinone zur Prophylaxe und Behandlung von cerebralen Durchblutungsstörungen
BRPI0616801B8 (pt)	2005-10-04	2021-05-25	Bayer Healthcare Ag	"forma polimórfica de 5-cloro-n-({(5s)-2-oxo-3-[4-(3-oxo-4-morfolinil)-fenil]-1,3-oxazolidin-5-il}-metil)-2-tiofenocarboxamida, seus processos de preparação e seus usos, medicamento, e processo para prevenção de coagulação de sangue in vitro
DE102005047561A1 (de)	2005-10-04	2007-04-05	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung
TW200804358A (en)	2006-03-31	2008-01-16	Res Found Itsuu Lab	Novel compound having heterocycle
JPWO2009044777A1 (ja) *	2007-10-02	2011-02-10	財団法人乙卯研究所	７員ヘテロ環を有するオキサゾリジノン誘導体
US20130296569A1 (en)	2010-11-03	2013-11-07	Vijaykumar Jagdishwar Patil	Process for the preparation of phosphoric acid mono-(1--4-methoxymethyl-piperidin-4-yl) ester
WO2015173664A1 (en)	2014-05-14	2015-11-19	Wockhardt Limited	Process for the preparation of (5s)-n-{3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4801600A (en) *	1987-10-09	1989-01-31	E. I. Du Pont De Nemours And Company	Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents
CA1320730C (en) *	1987-10-16	1993-07-27	The Du Pont Merck Pharmaceutical Company	Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents
ATE95176T1 (de) *	1987-10-21	1993-10-15	Du Pont Merck Pharma	Aminomethyl-oxo-oxazolidinyl-ethenylbenzenderivate, nuetzlich als antibakterielles mittel.
US4948801A (en) *	1988-07-29	1990-08-14	E. I. Du Pont De Nemours And Company	Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents
JP2865211B2 (ja) *	1988-09-15	1999-03-08	ファルマシア・アンド・アップジョン・カンパニー	５’―インドリニル―５β―アミドメチルオキサゾリジン―２―オン類、３―（縮合環置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類および３―（窒素原子置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類
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
EP0730591B1 (en) *	1993-11-22	1999-07-14	PHARMACIA & UPJOHN COMPANY	Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones
JPH0873455A (ja) *	1994-03-15	1996-03-19	Upjohn Co:The	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
GB9601666D0 (en) *	1996-01-27	1996-03-27	Zeneca Ltd	Chemical compounds

1998
- 1998-10-30 EP EP98956200A patent/EP1030852B1/en not_active Expired - Lifetime
- 1998-10-30 IL IL13606298A patent/IL136062A/en not_active IP Right Cessation
- 1998-10-30 US US09/183,432 patent/US5998406A/en not_active Expired - Fee Related
- 1998-10-30 DK DK98956200T patent/DK1030852T3/da active
- 1998-10-30 CN CNB988093952A patent/CN1154644C/zh not_active Expired - Fee Related
- 1998-10-30 TR TR2000/01330T patent/TR200001330T2/xx unknown
- 1998-10-30 NZ NZ504503A patent/NZ504503A/xx unknown
- 1998-10-30 RU RU2000114891/04A patent/RU2215740C2/ru not_active IP Right Cessation
- 1998-10-30 PT PT98956200T patent/PT1030852E/pt unknown
- 1998-10-30 KR KR1020007005061A patent/KR20010031953A/ko not_active Application Discontinuation
- 1998-10-30 DE DE69818294T patent/DE69818294T2/de not_active Expired - Fee Related
- 1998-10-30 WO PCT/US1998/022639 patent/WO1999024428A1/en not_active Application Discontinuation
- 1998-10-30 JP JP2000520440A patent/JP2001522849A/ja not_active Withdrawn
- 1998-10-30 ES ES98956200T patent/ES2207010T3/es not_active Expired - Lifetime
- 1998-10-30 HU HU0100470A patent/HUP0100470A3/hu unknown
- 1998-10-30 AT AT98956200T patent/ATE250054T1/de not_active IP Right Cessation
- 1998-10-30 AU AU12778/99A patent/AU739055B2/en not_active Ceased
- 1998-10-30 SK SK618-2000A patent/SK284577B6/sk unknown
- 1998-10-30 CA CA002303959A patent/CA2303959A1/en not_active Abandoned
- 1998-10-30 BR BR9813985-1A patent/BR9813985A/pt not_active IP Right Cessation
2000
- 2000-05-11 NO NO20002434A patent/NO317291B1/no unknown
2001
- 2001-02-23 HK HK01101329A patent/HK1030373A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
SK6182000A3 (en)	2000-12-11
BR9813985A (pt)	2000-09-26
US5998406A (en)	1999-12-07
PT1030852E (pt)	2004-02-27
IL136062A (en)	2004-02-08
DK1030852T3 (da)	2003-12-22
HUP0100470A2 (hu)	2002-05-29
JP2001522849A (ja)	2001-11-20
ES2207010T3 (es)	2004-05-16
AU739055B2 (en)	2001-10-04
IL136062A0 (en)	2001-05-20
NO20002434D0 (no)	2000-05-11
CN1271358A (zh)	2000-10-25
AU1277899A (en)	1999-05-31
ATE250054T1 (de)	2003-10-15
KR20010031953A (ko)	2001-04-16
NO20002434L (no)	2000-05-11
HK1030373A1 (en)	2001-05-04
WO1999024428A1 (en)	1999-05-20
CN1154644C (zh)	2004-06-23
NZ504503A (en)	2002-10-25
HUP0100470A3 (en)	2002-08-28
EP1030852B1 (en)	2003-09-17
CA2303959A1 (en)	1999-05-20
TR200001330T2 (tr)	2000-11-21
EP1030852A1 (en)	2000-08-30
SK284577B6 (sk)	2005-07-01
RU2215740C2 (ru)	2003-11-10
DE69818294T2 (de)	2004-07-08
DE69818294D1 (de)	2003-10-23

Publication	Publication Date	Title
NO317291B1 (no)	2004-10-04	Oksazolidinonderivater og farmasoytiske preparater
US6218413B1 (en)	2001-04-17	Oxazolidinone antibacterial agents having a thiocarbonyl functionality
EP0750618B1 (en)	2003-02-19	Oxazolidinone derivatives and pharmaceutical compositions containing them
US5668286A (en)	1997-09-16	Oxazolidinone derivatives and pharmaceutical compositions containing them
US5700799A (en)	1997-12-23	Oxazolidinone antimicrobials containing substituted diazine moieties
US5688792A (en)	1997-11-18	Substituted oxazine and thiazine oxazolidinone antimicrobials
US6090820A (en)	2000-07-18	Spirocyclic and bicyclic diazinyl and carbazinyl oxazolidinones
US4461773A (en)	1984-07-24	P-Oxooxazolidinylbenzene compounds as antibacterial agents
EP1036074B1 (en)	2003-01-29	S-oxide tetrahydrothiopyran phenyloxazolidinones
US7012088B2 (en)	2006-03-14	Indolone oxazolidinones and derivatives thereof
JP2008544979A (ja)	2008-12-11	抗菌剤としてのホモモルホリンオキサゾリジノン
PL190431B1 (pl)	2005-12-30	Pochodne oksazolidynonów, ich zastosowanie i kompozycja farmaceutyczna je zawierająca
US7435751B2 (en)	2008-10-14	7-Fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents
MXPA00004528A (en)	2001-07-09	Oxazolidinone derivatives and pharmaceutical compositions
CZ20001687A3 (cs)	2000-10-11	Deriváty oxazolidinonu a farmaceutické kompozice
US20040142939A1 (en)	2004-07-22	N-Aryl-2-oxazolidinone-5-carboxamides and their derivatives
US20040204463A1 (en)	2004-10-14	N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
US6348459B1 (en)	2002-02-19	Sultam and sultone derived oxazolidinones
WO2007004032A1 (en)	2007-01-11	Oxazolidiones containing cyclobutane as antibacterial agents
WO2006051408A1 (en)	2006-05-18	Oxazolidinone derivatives as antimicrobials
SI9300172A (sl)	1993-12-31	Novi (1-normon-2-il)oksazoli