ZA200300471B - Oxazolidinone derivatives as antimicrobials. - Google Patents
Oxazolidinone derivatives as antimicrobials. Download PDFInfo
- Publication number
- ZA200300471B ZA200300471B ZA200300471A ZA200300471A ZA200300471B ZA 200300471 B ZA200300471 B ZA 200300471B ZA 200300471 A ZA200300471 A ZA 200300471A ZA 200300471 A ZA200300471 A ZA 200300471A ZA 200300471 B ZA200300471 B ZA 200300471B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- fluoro
- formula
- oxo
- acetamide
- Prior art date
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- 239000004599 antimicrobial Substances 0.000 title description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 389
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 177
- 150000001875 compounds Chemical class 0.000 claims description 145
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 140
- 125000000217 alkyl group Chemical group 0.000 claims description 113
- 125000004193 piperazinyl group Chemical group 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
- -1 Cs-12 Chemical group 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 9
- 150000002390 heteroarenes Chemical class 0.000 claims description 9
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 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 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004989 dicarbonyl group Chemical group 0.000 claims description 4
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002207 metabolite Substances 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 3
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 229940043279 diisopropylamine Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 150000003233 pyrroles Chemical class 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- 229940035437 1,3-propanediol Drugs 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000000813 microbial effect Effects 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 229940086542 triethylamine Drugs 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- WTXXSZUATXIAJO-OWBHPGMISA-N (Z)-14-methylpentadec-2-enoic acid Chemical compound CC(CCCCCCCCCC\C=C/C(=O)O)C WTXXSZUATXIAJO-OWBHPGMISA-N 0.000 claims 1
- 240000006890 Erythroxylum coca Species 0.000 claims 1
- 102100022631 Glutamate receptor ionotropic, NMDA 2C Human genes 0.000 claims 1
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 235000008957 cocaer Nutrition 0.000 claims 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 1
- 238000012053 enzymatic serum creatinine assay Methods 0.000 claims 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 229940093956 potassium carbonate Drugs 0.000 claims 1
- 229960001407 sodium bicarbonate Drugs 0.000 claims 1
- 108091008646 testicular receptors Proteins 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
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- 230000000844 anti-bacterial effect Effects 0.000 description 6
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- 239000003242 anti bacterial agent Substances 0.000 description 4
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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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN654DE2000 | 2000-07-17 |
Publications (1)
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|---|---|
| ZA200300471B true ZA200300471B (en) | 2003-10-29 |
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|---|---|---|---|
| ZA200300471A ZA200300471B (en) | 2000-07-17 | 2003-01-17 | Oxazolidinone derivatives as antimicrobials. |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6734307B2 (fr) |
| EP (1) | EP1303511A1 (fr) |
| JP (1) | JP2004504321A (fr) |
| CN (1) | CN1447808A (fr) |
| AU (2) | AU6937001A (fr) |
| BR (1) | BR0112826A (fr) |
| CA (1) | CA2415965A1 (fr) |
| CZ (1) | CZ2003228A3 (fr) |
| HU (1) | HUP0302918A2 (fr) |
| MX (1) | MXPA03000503A (fr) |
| NZ (1) | NZ523700A (fr) |
| PL (1) | PL363960A1 (fr) |
| RU (1) | RU2292345C9 (fr) |
| SK (1) | SK1402003A3 (fr) |
| WO (1) | WO2002006278A1 (fr) |
| ZA (1) | ZA200300471B (fr) |
Families Citing this family (45)
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| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| US6734307B2 (en) | 2000-07-17 | 2004-05-11 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| WO2003008389A1 (fr) * | 2001-07-16 | 2003-01-30 | Ranbaxy Laboratories Limited | Derives d'oxazolidinone utilises comme antimicrobiens potentiels |
| EP1385834B1 (fr) * | 2001-04-17 | 2005-09-14 | Merck & Co., Inc. | Antibiotiques oxazolidinone contenant du bicyclo[3,1,0] hexane et derives de ces derniers |
| US6956040B2 (en) | 2001-07-16 | 2005-10-18 | Ranbaxy Laboratories Limited | Oxazolidinone piperazinyl derivatives as potential antimicrobials |
| FR2828488B1 (fr) | 2001-08-08 | 2005-06-10 | Oreal | Composition pour la teinture de fibres keratiniques contenant une paraphenylenediamine substituee par un radical diazacycloheptane |
| CA2478502A1 (fr) * | 2002-04-01 | 2003-10-09 | Cadila Healthcare Limited | Nouveaux composes anti-infectieux, processus de preparation de ces composes et compositions pharmaceutiques les contenant |
| WO2003093247A2 (fr) * | 2002-04-30 | 2003-11-13 | Orchid Chemicals & Pharmaceuticals Ltd | Nouveaux agents antibacteriens |
| JP2005529924A (ja) * | 2002-05-15 | 2005-10-06 | ランバクシー ラボラトリーズ リミテッド | フェニルオキサゾリジノン誘導体 |
| WO2003097640A1 (fr) * | 2002-05-22 | 2003-11-27 | Orchid Chemicals & Pharmaceuticals Ltd. | Derives d'oxazolidinone utilises en tant qu'agents antibacteriens |
| EA200500283A1 (ru) * | 2002-07-29 | 2005-08-25 | Рэнбакси Лабораториз Лимитед | Производные оксазолидинона как противомикробные средства |
| US7217726B2 (en) | 2002-08-22 | 2007-05-15 | Orchid Chemicals & Pharmaceuticals Limited | Antibacterial agents |
| AU2002339721A1 (en) | 2002-09-20 | 2004-04-08 | Lupin Limited | Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents |
| US6875784B2 (en) * | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| AU2003202753A1 (en) * | 2003-02-07 | 2004-08-30 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| US7223788B2 (en) | 2003-02-14 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Substituted N-aryl heterocycles, process for their preparation and their use as medicaments |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US20080214565A1 (en) * | 2003-04-07 | 2008-09-04 | Anita Mehta | Oxazolidinone Derivatives as Antimicrobials |
| CA2521685A1 (fr) | 2003-04-09 | 2004-10-21 | Pharmacia & Upjohn Company Llc | Derives de [3.1.0] bicyclohexylphenyl-oxazolidinone antimicrobiens et leurs analogues |
| WO2005003087A2 (fr) * | 2003-07-01 | 2005-01-13 | Orchid Chemicals And Pharmaceuticals Ltd. | Composes nouveaux utiles comme agents anti-bacteriens |
| JP2007521283A (ja) * | 2003-07-02 | 2007-08-02 | メルク アンド カンパニー インコーポレーテッド | シクロプロピル基で置換されたオキサゾリジノン系抗生物質およびその誘導体 |
| US20070293493A1 (en) * | 2003-07-02 | 2007-12-20 | Milton Hammond | Oxazolidinone antibiotics and derivatives thereof |
| KR20060113625A (ko) | 2003-07-02 | 2006-11-02 | 머크 앤드 캄파니 인코포레이티드 | 시클로프로필기 치환된 옥사졸리디논 항생제 및 그의유도체 |
| AU2004256084B2 (en) * | 2003-07-02 | 2007-10-18 | Kyorin Pharmaceutical Co., Ltd. | Oxazolidinone antibiotics and derivatives thereof |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| WO2005051933A1 (fr) * | 2003-11-28 | 2005-06-09 | Ranbaxy Laboratories Limited | Procede ameliore de synthese d'ester test-butylique d'acide 4-(4-benzyloxy-carbonylamino-2-fluorophenyl)-piperazine-1-carboxylique, compose intermediaire cle de la preparation d'agents antimicrobiens a l'oxazolidinone, et composes ainsi prepares |
| WO2005082899A1 (fr) * | 2004-01-28 | 2005-09-09 | Ranbaxy Laboratories Limited | Derives d'oxazolidinones utilises en tant qu'antimicrobiens |
| WO2006040614A1 (fr) * | 2004-10-11 | 2006-04-20 | Ranbaxy Laboratories Limited | Derives d'oxazolidinone substitues |
| CA2610978A1 (fr) | 2005-06-29 | 2007-01-04 | Pharmacia & Upjohn Company Llc | Oxazolidinones d'homomorpholine en tant qu'agents antibacteriens |
| FR2895735B1 (fr) | 2005-12-30 | 2008-04-18 | Ecopack France | Valve a poche amelioree |
| US7728031B2 (en) | 2006-02-24 | 2010-06-01 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole derivatives |
| CA2647605A1 (fr) * | 2006-03-31 | 2007-10-11 | Research Foundation Itsuu Laboratory | Nouveau compose ayant un heterocycle |
| WO2009036132A1 (fr) | 2007-09-11 | 2009-03-19 | Abbott Laboratories | N-oxydes d'octahydro-pyrrolo[3,4-b]pyrrole |
| EP2233484A3 (fr) | 2007-10-02 | 2012-04-04 | Research Foundation Itsuu Laboratory | Dérivés de oxazolidone ayant un cycle hétérocyclique à sept membre |
| WO2009132310A1 (fr) * | 2008-04-25 | 2009-10-29 | Wisconsin Alumni Research Foundation | Inhibiteurs de udp-galactopyranose empêchant la croissance mycobactérienne |
| JP2014500247A (ja) | 2010-11-03 | 2014-01-09 | ウォックハート リミテッド | リン酸モノ−（１−｛４−［（ｓ）―５−（アセチルアミノメチル）−２−オキソ−オキサゾリジン−３−イル］−２，６−ジフルオロフェニル｝−４−メトキシメチルピペリジン−４−イル）エステルの調製方法 |
| US9359344B2 (en) | 2011-09-29 | 2016-06-07 | Xuanzhu Pharma Co., Ltd. | Biaryl heterocycle substituted oxazolidinone antibacterial agents |
| WO2015173664A1 (fr) | 2014-05-14 | 2015-11-19 | Wockhardt Limited | Procédé pour la préparation de(5s)-n-{3- [3,5-difluoro-4- (4-hydroxy -4-méthoxyméthyl-pipéridine-1-yl)-phényl]-2-oxo-oxazolidine-5-ylméthyl}-acétamide |
| US10080757B2 (en) | 2016-03-11 | 2018-09-25 | Wisconsin Alumni Research Foundation | Inhibitors of UDP-galactopyranose mutase |
| CN109020873B (zh) * | 2018-07-16 | 2020-04-28 | 青岛农业大学 | 以靶标蛋白甾醇14α-脱甲基酶三维结构筛选的化合物及其在在制备杀菌剂中的应用 |
| EP3886854A4 (fr) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Composés pyrrole et pyrazole et leurs procédés d'utilisation |
| CA3134635A1 (fr) | 2019-04-03 | 2020-10-08 | Aligos Therapeutics, Inc. | Composes de pyrrole |
| CA3183397A1 (fr) | 2020-06-18 | 2021-12-23 | Daryl C. Drummond | Composes du type oxazolidinone, compositions de liposome comprenant des composes du type oxazolidinone et methodes d'utilisation associees |
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| US4801600A (en) | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4921869A (en) | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| CA1320730C (fr) | 1987-10-16 | 1993-07-27 | The Du Pont Merck Pharmaceutical Company | Derives d'aminomethyloxooxazolidinylaroylbenzene, agents antibacteriens |
| US5254577A (en) | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene 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 |
| WO1990002744A1 (fr) | 1988-09-15 | 1990-03-22 | The Upjohn Company | 5-beta-amidomethyle-oxazolidine-2-ones a substitution en position 3 |
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| DK0610265T3 (da) | 1991-11-01 | 1997-06-09 | Upjohn Co | Substituerede aryl- og heteroarylphenyloxazolidioner, som kan anvendes som antibakterielle midler |
| SK283420B6 (sk) | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| KR100312903B1 (ko) * | 1993-11-22 | 2002-02-28 | 로렌스 티. 마이젠헬더 | 치환된-하이드록시아세틸피페라진페닐옥사졸리디논의에스테르 |
| 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 |
| PT1019385E (pt) * | 1995-09-15 | 2004-06-30 | Upjohn Co | N-oxidos de aminoaril-oxazolidinona |
| GB9521508D0 (en) | 1995-10-20 | 1995-12-20 | 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 |
| GB9614238D0 (en) * | 1996-07-06 | 1996-09-04 | Zeneca Ltd | Chemical compounds |
| WO1998054161A1 (fr) * | 1997-05-30 | 1998-12-03 | Pharmacia & Upjohn Company | Agents antibacteriens oxazolidinone ayant une fonctionnalite thiocarbonyle |
| CA2351062A1 (fr) | 1998-11-27 | 2000-06-08 | Pharmacia & Upjohn Company | Agents antibacteriens oxazolidinone a fonction thiocarbonyle |
| US6734307B2 (en) | 2000-07-17 | 2004-05-11 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
-
2001
- 2001-07-16 US US09/906,215 patent/US6734307B2/en not_active Expired - Fee Related
- 2001-07-16 HU HU0302918A patent/HUP0302918A2/hu unknown
- 2001-07-16 AU AU6937001A patent/AU6937001A/xx active Pending
- 2001-07-16 JP JP2002512181A patent/JP2004504321A/ja active Pending
- 2001-07-16 CA CA002415965A patent/CA2415965A1/fr not_active Abandoned
- 2001-07-16 PL PL01363960A patent/PL363960A1/xx not_active Application Discontinuation
- 2001-07-16 CN CN01814422A patent/CN1447808A/zh active Pending
- 2001-07-16 WO PCT/IB2001/001262 patent/WO2002006278A1/fr active IP Right Grant
- 2001-07-16 CZ CZ2003228A patent/CZ2003228A3/cs unknown
- 2001-07-16 BR BR0112826-4A patent/BR0112826A/pt not_active IP Right Cessation
- 2001-07-16 RU RU2003103767/04A patent/RU2292345C9/ru not_active IP Right Cessation
- 2001-07-16 SK SK140-2003A patent/SK1402003A3/sk not_active Application Discontinuation
- 2001-07-16 MX MXPA03000503A patent/MXPA03000503A/es unknown
- 2001-07-16 AU AU2001269370A patent/AU2001269370B2/en not_active Ceased
- 2001-07-16 NZ NZ523700A patent/NZ523700A/en unknown
- 2001-07-16 EP EP01947730A patent/EP1303511A1/fr not_active Withdrawn
-
2002
- 2002-01-21 US US10/483,905 patent/US20040242591A1/en not_active Abandoned
-
2003
- 2003-01-17 ZA ZA200300471A patent/ZA200300471B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001269370B2 (en) | 2005-10-27 |
| US20020103186A1 (en) | 2002-08-01 |
| BR0112826A (pt) | 2003-06-24 |
| RU2292345C9 (ru) | 2007-05-10 |
| US6734307B2 (en) | 2004-05-11 |
| WO2002006278A1 (fr) | 2002-01-24 |
| RU2292345C2 (ru) | 2007-01-27 |
| JP2004504321A (ja) | 2004-02-12 |
| SK1402003A3 (en) | 2003-08-05 |
| HUP0302918A2 (hu) | 2003-12-29 |
| CA2415965A1 (fr) | 2002-01-24 |
| US20040242591A1 (en) | 2004-12-02 |
| CN1447808A (zh) | 2003-10-08 |
| NZ523700A (en) | 2004-11-26 |
| AU6937001A (en) | 2002-01-30 |
| CZ2003228A3 (cs) | 2003-06-18 |
| MXPA03000503A (es) | 2003-10-14 |
| PL363960A1 (en) | 2004-11-29 |
| EP1303511A1 (fr) | 2003-04-23 |
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