SK7572002A3 - Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents - Google Patents

Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents Download PDF

Info

Publication number: SK7572002A3
Authority: SK; Slovakia
Prior art keywords: oxo; phenyl; methyl; fluoro; oxazolidin
Prior art date: 1999-12-21

Application number

SK757-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Jackson B Hester

David L Alexander

Original Assignee

Upjohn Co

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.)

1999-12-21

Filing date

2000-12-12

Publication date

2002-12-03

2000-12-12 Application filed by Upjohn Co filed Critical Upjohn Co

2002-12-03 Publication of SK7572002A3 publication Critical patent/SK7572002A3/sk

Links

IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 11
125000005555 sulfoximide group Chemical group 0.000 title description 3
239000004599 antimicrobial Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 86
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 48
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 138
WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 claims description 98
-1 4, 4-thiazinan-4-yl Chemical group 0.000 claims description 83
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 48
IIPJWNFOLPDTEQ-UHFFFAOYSA-N cyclopropanecarbothioamide Chemical compound NC(=S)C1CC1 IIPJWNFOLPDTEQ-UHFFFAOYSA-N 0.000 claims description 42
125000001841 imino group Chemical group [H]N=* 0.000 claims description 41
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 17
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims description 15
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
208000015181 infectious disease Diseases 0.000 claims description 8
125000003713 acetylimino group Chemical group [H]C([H])([H])C(=O)N=[*] 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 5
230000000813 microbial effect Effects 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
150000002923 oximes Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
208000001860 Eye Infections Diseases 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
208000011323 eye infectious disease Diseases 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
206010040872 skin infection Diseases 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 7
241000894006 Bacteria Species 0.000 abstract description 3
230000003389 potentiating effect Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
238000000034 method Methods 0.000 description 30
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LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 23
239000000243 solution Substances 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
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238000006243 chemical reaction Methods 0.000 description 18
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
229940125758 compound 15 Drugs 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000012258 stirred mixture Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229940125782 compound 2 Drugs 0.000 description 4
229940126214 compound 3 Drugs 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
239000007788 liquid Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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239000007858 starting material Substances 0.000 description 4
150000003462 sulfoxides Chemical class 0.000 description 4
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 3
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
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239000012141 concentrate Substances 0.000 description 3
WHQPNJDXIICPAH-UHFFFAOYSA-N ethyl propanedithioate Chemical compound CCSC(=S)CC WHQPNJDXIICPAH-UHFFFAOYSA-N 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
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150000002576 ketones Chemical class 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
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229940125936 compound 42 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000005022 dithioester group Chemical group 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
229940032049 enterococcus faecalis Drugs 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 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
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 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
235000019359 magnesium stearate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
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 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 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
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 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
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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
238000005932 reductive alkylation reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
229910000029 sodium carbonate 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
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003564 thiocarbonyl compounds Chemical class 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
230000017105 transposition 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
241001148471 unidentified anaerobic bacterium Species 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008215 water for injection 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
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- 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)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Ophthalmology & Optometry (AREA)
Dermatology (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)

SK757-2002A 1999-12-21 2000-12-12 Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents SK7572002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US17191699P	1999-12-21	1999-12-21
PCT/US2000/032451 WO2001046185A1 (fr)	1999-12-21	2000-12-12	Oxazolidinones presentant une fonctionnalite sulfoximine et leur utilisation comme agents antimicrobiens

Publications (1)

Publication Number	Publication Date
SK7572002A3 true SK7572002A3 (en)	2002-12-03

Family

ID=22625632

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK757-2002A SK7572002A3 (en)	1999-12-21	2000-12-12	Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents

Country Status (22)

Country	Link
US (1)	US20010046987A1 (fr)
EP (1)	EP1242417A1 (fr)
JP (1)	JP2003518117A (fr)
KR (1)	KR20020067557A (fr)
CN (1)	CN1221548C (fr)
AR (1)	AR029211A1 (fr)
AU (1)	AU782078B2 (fr)
BR (1)	BR0016605A (fr)
CA (1)	CA2389482A1 (fr)
CO (1)	CO5251427A1 (fr)
CZ (1)	CZ20022142A3 (fr)
EA (1)	EA005567B1 (fr)
HU (1)	HUP0203869A2 (fr)
IL (1)	IL150348A0 (fr)
MX (1)	MXPA02006233A (fr)
NO (1)	NO20022973L (fr)
NZ (1)	NZ519725A (fr)
PE (1)	PE20010931A1 (fr)
PL (1)	PL356478A1 (fr)
SK (1)	SK7572002A3 (fr)
WO (1)	WO2001046185A1 (fr)
ZA (1)	ZA200204166B (fr)

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GB9928568D0 (en)	1999-12-03	2000-02-02	Zeneca Ltd	Chemical compounds
DE19962924A1 (de)	1999-12-24	2001-07-05	Bayer Ag	Substituierte Oxazolidinone und ihre Verwendung
GB0009803D0 (en)	2000-04-25	2000-06-07	Astrazeneca Ab	Chemical compounds
EP1385844B1 (fr) *	2001-04-07	2006-07-05	Astrazeneca AB	Oxazolidinones contenant un groupe sulfonimide en tant qu'antibiotique
GB0108793D0 (en) *	2001-04-07	2001-05-30	Astrazeneca Ab	Chemical compounds
GB0108794D0 (en) *	2001-04-07	2001-05-30	Astrazeneca Ab	Chemical compound
GB0108764D0 (en) *	2001-04-07	2001-05-30	Astrazeneca Ab	Chemical compounds
DE10129725A1 (de)	2001-06-20	2003-01-02	Bayer Ag	Kombinationstherapie substituierter Oxazolidinone
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
TW200403240A (en)	2002-06-28	2004-03-01	Upjohn Co	Difluorothioacetamides of oxazolidinones as antibacterial agents
US6875784B2 (en)	2002-10-09	2005-04-05	Pharmacia & Upjohn Company	Antimibicrobial [3.1.0.] bicyclic oxazolidinone 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
WO2004089943A1 (fr) *	2003-04-09	2004-10-21	Pharmacia & Upjohn Company Llc	Derives de [3.1.0] bicyclohexylphenyl-oxazolidinone antimicrobiens et leurs analogues
US7304050B2 (en)	2003-09-16	2007-12-04	Pfizer Inc.	Antibacterial agents
US7265140B2 (en) *	2003-09-23	2007-09-04	Pfizer Inc	Acyloxymethylcarbamate prodrugs of oxazolidinones
DE10355461A1 (de)	2003-11-27	2005-06-23	Bayer Healthcare Ag	Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung
CA2589250A1 (fr) *	2004-11-29	2006-06-01	Pharmacia & Upjohn Company Llc	Utilisation de diazepine oxazolidinones comme agents antibacteriens
DE102004062475A1 (de) *	2004-12-24	2006-07-06	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung
EP1685841A1 (fr)	2005-01-31	2006-08-02	Bayer Health Care Aktiengesellschaft	Prevention et traitement de troubles thromboemboliques
ATE449773T1 (de)	2005-06-29	2009-12-15	Pharmacia & Upjohn Co Llc	Homomorpholinoxazolidinone als antibakterielle mittel
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
JP5416408B2 (ja)	2005-10-04	2014-02-12	バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング	５−クロロ−ｎ−（｛（５ｓ）−２−オキソ−３−［４−（３−オキソ−４−モルホリニル）−フェニル］−１，３−オキサゾリジン−５−イル｝−メチル）−２−チオフェンカルボキサミドの新規多形および無定形
DE102005047561A1 (de)	2005-10-04	2007-04-05	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung
DE102007028319A1 (de) *	2007-06-20	2008-12-24	Bayer Healthcare Ag	Substituierte Oxazolidinone und ihre Verwendung
WO2021184339A1 (fr) *	2020-03-20	2021-09-23	Merck Sharp & Dohme Corp.	Composé d'oxazolidinone et procédés d'utilisation de celui-ci comme agent antibactérien

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MY115155A (en) *	1993-09-09	2003-04-30	Upjohn Co	Substituted oxazine and thiazine oxazolidinone antimicrobials.
US5688792A (en) *	1994-08-16	1997-11-18	Pharmacia & Upjohn Company	Substituted oxazine and thiazine oxazolidinone antimicrobials
PT792273E (pt) *	1994-11-15	2003-06-30	Upjohn Co	Produtos antibacterianos de oxazolidinona substituida com oxazina e tiazina biciclicas
ATE207487T1 (de) *	1995-09-01	2001-11-15	Upjohn Co	Phenyloxazolidinone mit einer c-c-bindung zu 4-8 gliedrigen heterocyclen
CN1138765C (zh) *	1997-05-30	2004-02-18	法玛西雅厄普约翰美国公司	带有硫代羰基功能基的噁唑烷酮抗菌剂

2000
- 2000-12-12 CA CA002389482A patent/CA2389482A1/fr not_active Abandoned
- 2000-12-12 HU HU0203869A patent/HUP0203869A2/hu unknown
- 2000-12-12 MX MXPA02006233A patent/MXPA02006233A/es unknown
- 2000-12-12 EP EP00983792A patent/EP1242417A1/fr not_active Withdrawn
- 2000-12-12 CN CNB008160449A patent/CN1221548C/zh not_active Expired - Fee Related
- 2000-12-12 NZ NZ519725A patent/NZ519725A/en unknown
- 2000-12-12 WO PCT/US2000/032451 patent/WO2001046185A1/fr not_active Application Discontinuation
- 2000-12-12 EA EA200200699A patent/EA005567B1/ru not_active IP Right Cessation
- 2000-12-12 BR BR0016605-7A patent/BR0016605A/pt not_active IP Right Cessation
- 2000-12-12 SK SK757-2002A patent/SK7572002A3/sk unknown
- 2000-12-12 CZ CZ20022142A patent/CZ20022142A3/cs unknown
- 2000-12-12 KR KR1020027007958A patent/KR20020067557A/ko not_active Withdrawn
- 2000-12-12 JP JP2001547095A patent/JP2003518117A/ja active Pending
- 2000-12-12 IL IL15034800A patent/IL150348A0/xx unknown
- 2000-12-12 PL PL00356478A patent/PL356478A1/xx not_active Application Discontinuation
- 2000-12-12 AU AU20502/01A patent/AU782078B2/en not_active Ceased
- 2000-12-14 US US09/736,858 patent/US20010046987A1/en not_active Abandoned
- 2000-12-19 PE PE2000001363A patent/PE20010931A1/es not_active Application Discontinuation
- 2000-12-20 CO CO00096639A patent/CO5251427A1/es not_active Application Discontinuation
- 2000-12-20 AR ARP000106795A patent/AR029211A1/es unknown
2002
- 2002-05-24 ZA ZA200204166A patent/ZA200204166B/xx unknown
- 2002-06-20 NO NO20022973A patent/NO20022973L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
PE20010931A1 (es)	2001-08-29
CA2389482A1 (fr)	2001-06-28
AU782078B2 (en)	2005-06-30
CN1221548C (zh)	2005-10-05
ZA200204166B (en)	2003-10-29
BR0016605A (pt)	2003-02-25
NO20022973D0 (no)	2002-06-20
US20010046987A1 (en)	2001-11-29
AU2050201A (en)	2001-07-03
CO5251427A1 (es)	2003-02-28
KR20020067557A (ko)	2002-08-22
HUP0203869A2 (hu)	2003-07-28
JP2003518117A (ja)	2003-06-03
EA005567B1 (ru)	2005-04-28
IL150348A0 (en)	2002-12-01
MXPA02006233A (es)	2002-12-05
EA200200699A1 (ru)	2003-02-27
NZ519725A (en)	2004-05-28
CZ20022142A3 (cs)	2002-11-13
PL356478A1 (en)	2004-06-28
EP1242417A1 (fr)	2002-09-25
CN1391572A (zh)	2003-01-15
WO2001046185A1 (fr)	2001-06-28
AR029211A1 (es)	2003-06-18
NO20022973L (no)	2002-08-20

Publication	Publication Date	Title
SK7572002A3 (en)	2002-12-03	Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents
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JPH08301869A (ja)	1996-11-19	ヘテロ原子−含有ベンゾシクロペンタン−オキサゾリジノン
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WO2009041972A1 (fr)	2009-04-02	Composés antibactériens et leurs procédés d'utilisation
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CA2589250A1 (fr)	2006-06-01	Utilisation de diazepine oxazolidinones comme agents antibacteriens
MXPA00000374A (en)	2001-03-05	Thiadiazolyl and oxadiazolyl phenyl oxazolidinone antibacterial agents
CA2383992A1 (fr)	2001-05-10	Oxazolidinones derivees de sultame et de sultone comme antibiotiques
CZ20001687A3 (cs)	2000-10-11	Deriváty oxazolidinonu a farmaceutické kompozice