CA2637811A1 - Benzisoxazole oxazolidinones as antibacterial agents - Google Patents
Benzisoxazole oxazolidinones as antibacterial agents Download PDFInfo
- Publication number
- CA2637811A1 CA2637811A1 CA002637811A CA2637811A CA2637811A1 CA 2637811 A1 CA2637811 A1 CA 2637811A1 CA 002637811 A CA002637811 A CA 002637811A CA 2637811 A CA2637811 A CA 2637811A CA 2637811 A1 CA2637811 A1 CA 2637811A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- benzo
- compound
- isoxazol
- oxo
- 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.)
- Abandoned
Links
- SUIUGBRIEQZELS-UHFFFAOYSA-N 1,2-benzoxazole;1,3-oxazolidin-2-one Chemical class O=C1NCCO1.C1=CC=C2C=NOC2=C1 SUIUGBRIEQZELS-UHFFFAOYSA-N 0.000 title description 4
- 239000003242 anti bacterial agent Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- -1 NHC1-6alkyl Chemical group 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 239000011593 sulfur Chemical group 0.000 claims abstract description 4
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- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
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- 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
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- 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 4
- 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
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- 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 2
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- 239000000203 mixture Substances 0.000 description 37
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
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- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 239000001993 wax Substances 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)
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76411306P | 2006-02-01 | 2006-02-01 | |
| US60/764,113 | 2006-02-01 | ||
| PCT/IB2007/000179 WO2007088438A2 (en) | 2006-02-01 | 2007-01-22 | Benzisoxazole oxazolidinones as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2637811A1 true CA2637811A1 (en) | 2007-08-09 |
Family
ID=38222566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002637811A Abandoned CA2637811A1 (en) | 2006-02-01 | 2007-01-22 | Benzisoxazole oxazolidinones as antibacterial agents |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20090221655A1 (enExample) |
| EP (1) | EP2032565A2 (enExample) |
| JP (1) | JP2009525318A (enExample) |
| CA (1) | CA2637811A1 (enExample) |
| WO (1) | WO2007088438A2 (enExample) |
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 |
|---|---|---|---|---|
| US112832A (en) * | 1871-03-21 | Improvement in apparatus for removing paint, varnish | ||
| US247622A (en) * | 1881-09-27 | Waltee e | ||
| US3597321A (en) * | 1969-04-17 | 1971-08-03 | Warner Lambert Pharmaceutical | Diagnostic compostion for the differentiation of staphylococci |
| WO1995024404A1 (en) * | 1994-03-11 | 1995-09-14 | Shaman Pharmaceuticals, Inc. | Preparation of symmetrical and unsymmetrical dithiin compounds |
| DE19514313A1 (de) * | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
| PL183919B1 (pl) * | 1995-06-02 | 2002-08-30 | Sanofi Synthelabo | Pochodne oksazolidynonu, sposób ich otrzymywania oraz ich farmaceutyczne zastosowanie |
| 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 |
| US6942802B2 (en) * | 2001-04-13 | 2005-09-13 | Wyeth Holdings Corporation | Removal of bacterial endotoxin in a protein solution by immobilized metal affinity chromatography |
-
2007
- 2007-01-22 US US12/278,006 patent/US20090221655A1/en not_active Abandoned
- 2007-01-22 CA CA002637811A patent/CA2637811A1/en not_active Abandoned
- 2007-01-22 EP EP07700520A patent/EP2032565A2/en not_active Withdrawn
- 2007-01-22 WO PCT/IB2007/000179 patent/WO2007088438A2/en not_active Ceased
- 2007-01-22 JP JP2008552906A patent/JP2009525318A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007088438A3 (en) | 2007-11-01 |
| WO2007088438A2 (en) | 2007-08-09 |
| US20090221655A1 (en) | 2009-09-03 |
| JP2009525318A (ja) | 2009-07-09 |
| EP2032565A2 (en) | 2009-03-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |