UA80112C2 - N-aryl-2-oxazolidinone-5-carboxamides, their derivatives and their use as antibacterials - Google Patents
N-aryl-2-oxazolidinone-5-carboxamides, their derivatives and their use as antibacterials Download PDFInfo
- Publication number
- UA80112C2 UA80112C2 UA20040807036A UA20040807036A UA80112C2 UA 80112 C2 UA80112 C2 UA 80112C2 UA 20040807036 A UA20040807036 A UA 20040807036A UA 20040807036 A UA20040807036 A UA 20040807036A UA 80112 C2 UA80112 C2 UA 80112C2
- Authority
- UA
- Ukraine
- Prior art keywords
- oxo
- oxazolidinecarboxamide
- dihydro
- methyl
- phenyl
- Prior art date
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- 230000000844 anti-bacterial effect Effects 0.000 title description 6
- 229940088710 antibiotic agent Drugs 0.000 title 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 196
- 238000000034 method Methods 0.000 claims description 192
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- 125000001424 substituent group Chemical group 0.000 claims description 29
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/12—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
-
- 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
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35949502P | 2002-02-25 | 2002-02-25 | |
| PCT/US2003/003125 WO2003072553A1 (en) | 2002-02-25 | 2003-02-24 | N-aryl-2-oxazolidinone-5-carboxamides and their derivates and their use as antibacterials |
Publications (1)
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| UA80112C2 true UA80112C2 (en) | 2007-08-27 |
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| UA20040807036A UA80112C2 (en) | 2002-02-25 | 2003-02-24 | N-aryl-2-oxazolidinone-5-carboxamides, their derivatives and their use as antibacterials |
Country Status (36)
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| EP (1) | EP1478629B1 (ru) |
| JP (1) | JP2005524660A (ru) |
| KR (1) | KR100613532B1 (ru) |
| CN (1) | CN1639135A (ru) |
| AP (1) | AP1902A (ru) |
| AR (1) | AR038536A1 (ru) |
| AT (1) | ATE342258T1 (ru) |
| AU (1) | AU2003210807A1 (ru) |
| BR (1) | BR0307924A (ru) |
| CA (1) | CA2476038A1 (ru) |
| CO (1) | CO5611128A2 (ru) |
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| DE (1) | DE60308998T2 (ru) |
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| EA (1) | EA007490B1 (ru) |
| EC (1) | ECSP045245A (ru) |
| ES (1) | ES2271615T3 (ru) |
| GE (1) | GEP20074198B (ru) |
| HR (1) | HRP20040717A2 (ru) |
| IS (1) | IS7376A (ru) |
| MA (1) | MA27180A1 (ru) |
| MX (1) | MXPA04008205A (ru) |
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| NO (1) | NO20044062L (ru) |
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| PL (1) | PL372461A1 (ru) |
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| TW (1) | TW200305568A (ru) |
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| WO (1) | WO2003072553A1 (ru) |
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| US7141588B2 (en) | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| AU2003265090A1 (en) | 2002-10-10 | 2004-05-04 | Pharmacia & Upjohn Comapny LLC | Antimicrobial 1-aryl dihydropyridone compounds |
| WO2004089943A1 (en) * | 2003-04-09 | 2004-10-21 | Pharmacia & Upjohn Company Llc | Antimicrobial [3.1.0] bicyclohexylphenyl-oxazolidinone derivatives and analogues |
| US8324398B2 (en) | 2003-06-03 | 2012-12-04 | Rib-X Pharmaceuticals, Inc. | Process for the synthesis of biaryl oxazolidinones |
| PT1656370E (pt) | 2003-06-03 | 2012-11-29 | Rib X Pharmaceuticals Inc | Compostos biaril-heterocíclicos e métodos de os produzir e de os utilizar |
| WO2005005399A1 (en) * | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Oxazolidinone antibiotics and derivatives thereof |
| KR20060113625A (ko) | 2003-07-02 | 2006-11-02 | 머크 앤드 캄파니 인코포레이티드 | 시클로프로필기 치환된 옥사졸리디논 항생제 및 그의유도체 |
| TW200526626A (en) | 2003-09-13 | 2005-08-16 | Astrazeneca Ab | Chemical compounds |
| US7304050B2 (en) * | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| TW200526649A (en) | 2003-12-17 | 2005-08-16 | Rib X Pharmaceuticals Inc | Halogenated biaryl heterocyclic compounds and methods of making and using the same |
| KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| WO2005082900A2 (en) * | 2004-01-28 | 2005-09-09 | Pharmacia & Upjohn Company Llc | Oxazolidinone amidoximes as antibacterial agents |
| MX2007001568A (es) * | 2004-08-06 | 2007-04-16 | Pharmacia & Upjohn Co Llc | Oxindol oxazolidinonas como agentes antibacterianos. |
| WO2006056877A2 (en) * | 2004-11-29 | 2006-06-01 | Pharmacia & Upjohn Company Llc | Diazepine oxazolidinones as antibacterial agents |
| EE05394B1 (et) * | 2004-12-24 | 2011-04-15 | Janssen Pharmaceutica N.V. | Kinoliinihendid kasutamiseks latentse tuberkuloosi ravis |
| EP1853586B1 (en) | 2005-02-18 | 2013-07-24 | AstraZeneca AB | Antibacterial piperidine derivatives |
| AU2006231919A1 (en) | 2005-04-06 | 2006-10-12 | Pharmacia & Upjohn Company Llc | 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents |
| US7592335B2 (en) | 2005-04-15 | 2009-09-22 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| ATE496914T1 (de) | 2005-06-08 | 2011-02-15 | Rib X Pharmaceuticals Inc | Verfahren zur synthese von triazolen |
| DE602006010702D1 (de) | 2005-06-29 | 2010-01-07 | Pharmacia & Upjohn Co Llc | Homomorpholinoxazolidinone als antibakterielle mittel |
| CA2614105A1 (en) * | 2005-07-06 | 2007-01-11 | Pharmacia & Upjohn Company Llc | Oxazolidinone carboxamides containing azetidine and cyclobutane as antibacterial agents |
| WO2007004032A1 (en) * | 2005-07-06 | 2007-01-11 | Pharmacia & Upjohn Company Llc | Oxazolidiones containing cyclobutane as antibacterial agents |
| CN101389627A (zh) * | 2005-12-23 | 2009-03-18 | 阿斯利康(瑞典)有限公司 | 具有抗菌作用的吡咯并吡啶、吡咯并嘧啶和吡咯并氮杂 |
| WO2007088478A1 (en) * | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Indazole oxazolidinones as antibacterial agents |
| CN101460495B (zh) * | 2006-03-31 | 2013-08-14 | 财团法人乙卯研究所 | 具有杂环的化合物 |
| EP2062878A4 (en) * | 2006-08-30 | 2010-09-08 | Shionogi & Co | HYDRAZINE AMIDE DERIVATIVE |
| US8088777B2 (en) * | 2006-08-30 | 2012-01-03 | Shionogi & Co., Ltd. | Urea derivative |
| CN101720325B (zh) * | 2007-08-06 | 2013-04-24 | 上海盟科药业有限公司 | 用于治疗细菌感染的抗菌邻-氟苯基噁唑烷酮 |
| EP2233484A3 (en) | 2007-10-02 | 2012-04-04 | Research Foundation Itsuu Laboratory | Oxazolidinone derivatives having a 7-membered heterocyclic ring |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| BRPI0917394A2 (pt) * | 2008-08-18 | 2019-09-24 | Univ Yale | moduladores de mif |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| US8841306B2 (en) | 2008-11-20 | 2014-09-23 | Panacea Biotec Ltd. | Antimicrobials |
| AU2010210627B2 (en) * | 2009-02-03 | 2016-03-03 | Merck Sharp & Dohme Llc | Crystalline form of R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate |
| AU2010264027B9 (en) | 2009-06-26 | 2013-06-13 | Panacea Biotec Ltd. | Novel azabicyclohexanes |
| CN103140483B (zh) | 2010-07-15 | 2015-06-24 | 拜耳知识产权有限责任公司 | 作为杀虫剂的新杂环化合物 |
| UA112897C2 (uk) | 2012-05-09 | 2016-11-10 | Байєр Фарма Акцієнгезелльшафт | Біциклічно заміщені урацили та їх застосування для лікування і/або профілактики захворювань |
| WO2015127316A1 (en) | 2014-02-21 | 2015-08-27 | Micurx Pharmaceuticals, Inc. | Water-soluble o-carbonyl phosphoramidate prodrugs for therapeutic administration |
| IL275443B (en) * | 2018-02-26 | 2022-07-01 | Sumitomo Chemical Co | Production method for an oxazolidinan compound |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705799A (en) | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| US5043443A (en) | 1988-07-29 | 1991-08-27 | Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives |
| US5182403A (en) | 1988-09-15 | 1993-01-26 | The Upjohn Company | Substituted 3(5'indazolyl) oxazolidin-2-ones |
| US5225565A (en) | 1988-09-15 | 1993-07-06 | The Upjohn Company | Antibacterial 3-(fused-ring substituted)phenyl-5β-amidomethyloxazolidin-2-ones |
| US5164510A (en) | 1988-09-15 | 1992-11-17 | The Upjohn Company | 5'Indolinyl-5β-amidomethyloxazolidin-2-ones |
| EP0417044A3 (en) | 1989-09-07 | 1991-06-12 | Ciba-Geigy Ag | Oxazolidinones and thiones as plantgrowth regulators |
| US5231188A (en) | 1989-11-17 | 1993-07-27 | The Upjohn Company | Tricyclic [6.5.51]-fused oxazolidinone antibacterial agents |
| CA2119556C (en) | 1991-11-01 | 2004-07-06 | Michael Robert Barbachyn | Substituted aryl- and heteroaryl-phenyloxazolidinones |
| SK283420B6 (sk) | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| CA2136324A1 (en) | 1992-07-08 | 1994-01-20 | Steven Joseph Brickner | 5'-indolinyl oxazolidinones useful against mycobacterium tuberculosis |
| ATE161833T1 (de) | 1992-12-08 | 1998-01-15 | Upjohn Co | Durch eine tropon gruppe substituierte phenyloxazolidinone-derivate als antibakterielles mittel |
| 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 |
| US5652238A (en) | 1993-11-22 | 1997-07-29 | Pharmacia & Upjohn Company | Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones |
| JPH0873455A (ja) | 1994-03-15 | 1996-03-19 | Upjohn Co:The | オキサゾリジノン誘導体及びこれを有効成分とする医薬組成物 |
| DE4425613A1 (de) | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| DE4425612A1 (de) | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| DE4425609A1 (de) | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
| DE19514313A1 (de) | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
| DE4429461A1 (de) * | 1994-08-19 | 1996-02-22 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| PT788498E (pt) | 1994-10-26 | 2002-02-28 | Upjohn Co | Compostos antimicrobianos de feniloxazolidinona |
| ES2193201T3 (es) | 1994-11-15 | 2003-11-01 | Upjohn Co | Agentes antibacterianos tipo oxazolidonas sustituidas con oxazina y tiazina biciclica. |
| EP0807112B1 (en) | 1995-02-03 | 2001-09-05 | PHARMACIA & UPJOHN COMPANY | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials |
| HRP960159A2 (en) | 1995-04-21 | 1997-08-31 | Bayer Ag | Benzocyclopentane oxazolidinones containing heteroatoms |
| ES2162047T3 (es) | 1995-05-11 | 2001-12-16 | Upjohn Co | Oxazolidinonas con resto diazinilo y carbazinilo espirociclico y biciclico. |
| RU2175324C2 (ru) | 1995-09-01 | 2001-10-27 | Фармация Энд Апджон Компани | Фенилоксазолидиноны, имеющие с-с-связь с 4-8-членными гетероциклическими кольцами |
| DE19601264A1 (de) | 1996-01-16 | 1997-07-17 | Bayer Ag | Pyrido-annellierte Thienyl- und Furanyl-Oxazolidinone |
| DE19601265A1 (de) | 1996-01-16 | 1997-07-17 | Bayer Ag | 2-Oxo- und 2-Thio-1,2-dihydrochinolinyl-oxazolidinone |
| DE19601627A1 (de) | 1996-01-18 | 1997-07-24 | Bayer Ag | Heteroatomhaltige Cyclopentanopyridyl-Oxazolidinone |
| GB9601666D0 (en) | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| DE19604223A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
| GB9702213D0 (en) | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| DE69716925T2 (de) | 1996-08-21 | 2003-09-11 | Pharmacia & Upjohn Co., Kalamazoo | Isoxazoline derivate und ihre verwendung als antimikroben |
| ATE293609T1 (de) | 1997-05-30 | 2005-05-15 | Upjohn Co | Antibakteriell wirksam oxazolidinone mit einer thiocarbonylfunktionalität |
| DE19730847A1 (de) | 1997-07-18 | 1999-01-28 | Bayer Ag | Tricyclisch substituierte Oxazolidinone |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| US6083967A (en) | 1997-12-05 | 2000-07-04 | Pharmacia & Upjohn Company | S-oxide and S,S-dioxide tetrahydrothiopyran phenyloxazolidinones |
| DE19802239A1 (de) | 1998-01-22 | 1999-07-29 | Bayer Ag | Neue mit Bicyclen substituierte Oxazolidinone |
| DE19802235A1 (de) | 1998-01-22 | 1999-07-29 | Bayer Ag | Mit tricyclischen Indolen substituierte Oxazolidinone |
| EP1049682A1 (en) | 1998-01-23 | 2000-11-08 | Versicor, Inc. | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| DE19805117A1 (de) | 1998-02-09 | 1999-08-12 | Bayer Ag | Neue Oxazolidinone mit azolhaltigen Tricyclen |
| TR200003595T2 (tr) | 1998-06-05 | 2001-07-23 | Astrazeneca Ab | Kimyasal bileşikler |
| GB9821938D0 (en) | 1998-10-09 | 1998-12-02 | Zeneca Ltd | Chemical compounds |
| IL144669A0 (en) | 1999-02-01 | 2002-05-23 | Upjohn Co | Process to prepare cyclic-sulfur fluorine containing oxazolidinones |
| JP2003501351A (ja) | 1999-05-27 | 2003-01-14 | ファルマシア・アンド・アップジョン・カンパニー | 抗菌剤としての二環系オキサゾリジノン |
| GB9928499D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical processes and intermediates |
| PL356478A1 (en) | 1999-12-21 | 2004-06-28 | Pharmacia & Upjohn Company | Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| GB0100110D0 (en) | 2001-01-04 | 2001-02-14 | Univ Leeds | Modulation of calcium channel activity |
| GB0113297D0 (en) | 2001-06-01 | 2001-07-25 | Astrazeneca Ab | Chemical Process |
| US7049443B2 (en) * | 2001-07-12 | 2006-05-23 | Pharmacia & Upjohn Company | Amide-containing compound having improved solubility and method of improving the solubility of an amide-containing compound |
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2003
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- 2003-02-21 MY MYPI20030608A patent/MY135233A/en unknown
- 2003-02-24 BR BR0307924-4A patent/BR0307924A/pt not_active IP Right Cessation
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- 2003-02-24 AU AU2003210807A patent/AU2003210807A1/en not_active Abandoned
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- 2003-02-24 AP APAP/P/2004/003110A patent/AP1902A/en active
- 2003-02-24 EP EP03743112A patent/EP1478629B1/en not_active Expired - Lifetime
- 2003-02-24 WO PCT/US2003/003125 patent/WO2003072553A1/en active IP Right Grant
- 2003-02-24 US US10/373,286 patent/US6919329B2/en not_active Expired - Fee Related
- 2003-02-24 YU YU72804A patent/YU72804A/sh unknown
- 2003-02-24 DK DK03743112T patent/DK1478629T3/da active
- 2003-02-24 AT AT03743112T patent/ATE342258T1/de not_active IP Right Cessation
- 2003-02-24 KR KR1020047013297A patent/KR100613532B1/ko not_active IP Right Cessation
- 2003-02-24 GE GEAP8378A patent/GEP20074198B/en unknown
- 2003-02-24 CN CNA038044986A patent/CN1639135A/zh active Pending
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