JP2009525318A - 抗菌剤としてのベンズイソオキサゾールオキサゾリジノン - Google Patents
抗菌剤としてのベンズイソオキサゾールオキサゾリジノン Download PDFInfo
- Publication number
- JP2009525318A JP2009525318A JP2008552906A JP2008552906A JP2009525318A JP 2009525318 A JP2009525318 A JP 2009525318A JP 2008552906 A JP2008552906 A JP 2008552906A JP 2008552906 A JP2008552906 A JP 2008552906A JP 2009525318 A JP2009525318 A JP 2009525318A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- benzo
- isoxazol
- bacteria
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- SUIUGBRIEQZELS-UHFFFAOYSA-N 1,2-benzoxazole;1,3-oxazolidin-2-one Chemical compound O=C1NCCO1.C1=CC=C2C=NOC2=C1 SUIUGBRIEQZELS-UHFFFAOYSA-N 0.000 title description 3
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- -1 1,2,3-triazol-1-ylmethyl Chemical group 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 241000894006 Bacteria Species 0.000 claims description 13
- YBHCQYXCJGYJAQ-NSHDSACASA-N (5r)-3-(3-methyl-1,2-benzoxazol-6-yl)-5-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one Chemical compound C([C@H]1CN(C(O1)=O)C=1C=C2ON=C(C2=CC=1)C)N1C=CN=N1 YBHCQYXCJGYJAQ-NSHDSACASA-N 0.000 claims description 10
- 208000035143 Bacterial infection Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- XSINJLZLAJNGPA-JTQLQIEISA-N methyl n-[[(5s)-3-(3-methyl-1,2-benzoxazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CNC(=O)OC)CN1C1=CC=C(C(C)=NO2)C2=C1 XSINJLZLAJNGPA-JTQLQIEISA-N 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- FHNCXMGWWSWATC-SNVBAGLBSA-N (5r)-3-(3-methyl-1,2-benzoxazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C=C2C(C)=NOC2=CC=1N1C[C@H](C(N)=O)OC1=O FHNCXMGWWSWATC-SNVBAGLBSA-N 0.000 claims description 4
- XPPNZDTXJBVDOT-LLVKDONJSA-N (5r)-n-methyl-3-(3-methyl-1,2-benzoxazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC=C(C(C)=NO2)C2=C1 XPPNZDTXJBVDOT-LLVKDONJSA-N 0.000 claims description 4
- CDVAHUJLILRHKN-NSHDSACASA-N n-[[(5s)-3-(3-methyl-1,2-benzoxazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C(C)=NO2)C2=C1 CDVAHUJLILRHKN-NSHDSACASA-N 0.000 claims description 4
- MAXZJAMYVNMHMI-NSHDSACASA-N n-[[(5s)-3-(3-methyl-1,2-benzoxazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(C(C)=NO2)C2=C1 MAXZJAMYVNMHMI-NSHDSACASA-N 0.000 claims description 4
- MLBTUBZPBFSYLU-INIZCTEOSA-N (5r)-3-(3-methyl-1,2-benzoxazol-6-yl)-5-[[4-(2-trimethylsilylethynyl)triazol-1-yl]methyl]-1,3-oxazolidin-2-one Chemical compound C([C@H]1CN(C(O1)=O)C=1C=C2ON=C(C2=CC=1)C)N1C=C(C#C[Si](C)(C)C)N=N1 MLBTUBZPBFSYLU-INIZCTEOSA-N 0.000 claims description 3
- LFIBOKAJICZQNE-LLVKDONJSA-N (5r)-n-methoxy-3-(3-methyl-1,2-benzoxazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NOC)CN1C1=CC=C(C(C)=NO2)C2=C1 LFIBOKAJICZQNE-LLVKDONJSA-N 0.000 claims description 3
- 241000192125 Firmicutes Species 0.000 claims description 3
- 241000588621 Moraxella Species 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 3
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 3
- 241000191967 Staphylococcus aureus Species 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- 206010014665 endocarditis Diseases 0.000 claims description 3
- 241000606125 Bacteroides Species 0.000 claims description 2
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 2
- 241000606161 Chlamydia Species 0.000 claims description 2
- 241000193403 Clostridium Species 0.000 claims description 2
- 208000008960 Diabetic foot Diseases 0.000 claims description 2
- 208000001860 Eye Infections Diseases 0.000 claims description 2
- 241000606790 Haemophilus Species 0.000 claims description 2
- 241000606768 Haemophilus influenzae Species 0.000 claims description 2
- 206010031252 Osteomyelitis Diseases 0.000 claims description 2
- 208000005141 Otitis Diseases 0.000 claims description 2
- 241000295644 Staphylococcaceae Species 0.000 claims description 2
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- 241000193996 Streptococcus pyogenes Species 0.000 claims description 2
- 208000019258 ear infection Diseases 0.000 claims description 2
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- 229940047650 haemophilus influenzae Drugs 0.000 claims description 2
- 230000003902 lesion Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 241000194017 Streptococcus Species 0.000 claims 2
- 206010014666 Endocarditis bacterial Diseases 0.000 claims 1
- 241000194033 Enterococcus Species 0.000 claims 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 1
- 241000191940 Staphylococcus Species 0.000 claims 1
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 1
- 208000033354 avian tuberculosis Diseases 0.000 claims 1
- 208000009361 bacterial endocarditis Diseases 0.000 claims 1
- 201000007119 infective endocarditis Diseases 0.000 claims 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 claims 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 description 44
- 238000002360 preparation method Methods 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 238000005481 NMR spectroscopy Methods 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- 239000012267 brine Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 239000010410 layer Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000007911 parenteral administration Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- LBNVCJHJRYJVPK-UHFFFAOYSA-N trimethyl(4-trimethylsilylbuta-1,3-diynyl)silane Chemical compound C[Si](C)(C)C#CC#C[Si](C)(C)C LBNVCJHJRYJVPK-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 239000003871 white petrolatum 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
- C07D413/14—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (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)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76411306P | 2006-02-01 | 2006-02-01 | |
| PCT/IB2007/000179 WO2007088438A2 (en) | 2006-02-01 | 2007-01-22 | Benzisoxazole oxazolidinones as antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009525318A true JP2009525318A (ja) | 2009-07-09 |
| JP2009525318A5 JP2009525318A5 (https=) | 2010-03-04 |
Family
ID=38222566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008552906A Withdrawn JP2009525318A (ja) | 2006-02-01 | 2007-01-22 | 抗菌剤としてのベンズイソオキサゾールオキサゾリジノン |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20090221655A1 (https=) |
| EP (1) | EP2032565A2 (https=) |
| JP (1) | JP2009525318A (https=) |
| CA (1) | CA2637811A1 (https=) |
| WO (1) | WO2007088438A2 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7973065B2 (en) * | 2009-10-07 | 2011-07-05 | Shaw Intellectual Properties Holding, Inc. | Antimicrobial compounds |
| PL236949B1 (pl) * | 2018-06-07 | 2021-03-08 | Politechnika Wroclawska | 1-(Bromometylo)-2,6,6-trimetylooktahydro-2-benzofuran, sposób jego wytwarzania oraz zastosowanie w inhibicji aktywności ureazy bakteryjnej |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US247622A (en) * | 1881-09-27 | Waltee e | ||
| US112832A (en) * | 1871-03-21 | Improvement in apparatus for removing paint, varnish | ||
| US3597321A (en) * | 1969-04-17 | 1971-08-03 | Warner Lambert Pharmaceutical | Diagnostic compostion for the differentiation of staphylococci |
| AU1989195A (en) * | 1994-03-11 | 1995-09-25 | Shaman Pharmaceuticals, Inc. | Preparation of symmetrical and unsymmetrical dithiin compounds |
| DE19514313A1 (de) * | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
| AU699367B2 (en) * | 1995-06-02 | 1998-12-03 | Sanofi-Aventis | Isoindole derivatives, their preparation and their application in therapy |
| US20040247622A1 (en) * | 1999-06-02 | 2004-12-09 | Genesis Research And Development Corporation Limited | Methods and compounds for the treatment of immunologically-mediated diseases using Mycobacterium vaccae |
| WO2002083710A2 (en) * | 2001-04-13 | 2002-10-24 | Wyeth Holdings Corporation | Removal of bacterial endotoxin in a protein solution by immobilized metal affinity chromatography |
-
2007
- 2007-01-22 JP JP2008552906A patent/JP2009525318A/ja not_active Withdrawn
- 2007-01-22 WO PCT/IB2007/000179 patent/WO2007088438A2/en not_active Ceased
- 2007-01-22 EP EP07700520A patent/EP2032565A2/en not_active Withdrawn
- 2007-01-22 US US12/278,006 patent/US20090221655A1/en not_active Abandoned
- 2007-01-22 CA CA002637811A patent/CA2637811A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090221655A1 (en) | 2009-09-03 |
| WO2007088438A3 (en) | 2007-11-01 |
| EP2032565A2 (en) | 2009-03-11 |
| WO2007088438A2 (en) | 2007-08-09 |
| CA2637811A1 (en) | 2007-08-09 |
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