CA2603899A1 - 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents - Google Patents
7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents Download PDFInfo
- Publication number
- CA2603899A1 CA2603899A1 CA002603899A CA2603899A CA2603899A1 CA 2603899 A1 CA2603899 A1 CA 2603899A1 CA 002603899 A CA002603899 A CA 002603899A CA 2603899 A CA2603899 A CA 2603899A CA 2603899 A1 CA2603899 A1 CA 2603899A1
- Authority
- CA
- Canada
- Prior art keywords
- fluoro
- compound
- indol
- dihydro
- mmol
- 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
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- 239000003242 anti bacterial agent Substances 0.000 title abstract description 14
- FFMDRLBKWBUTEW-UHFFFAOYSA-N 7-fluoro-1,3-dihydroindol-2-one;1,3-oxazolidin-2-one Chemical class O=C1NCCO1.FC1=CC=CC2=C1NC(=O)C2 FFMDRLBKWBUTEW-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 33
- 208000015181 infectious disease Diseases 0.000 claims description 22
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- RYXZVPPFWXWUKQ-JTQLQIEISA-N methyl n-[[(5s)-3-(7-fluoro-1-methyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CNC(=O)OC)CN1C(C=C1F)=CC2=C1N(C)C(=O)C2 RYXZVPPFWXWUKQ-JTQLQIEISA-N 0.000 claims description 2
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- UJMYZAYRKMULLR-UQKRIMTDSA-N tert-butyl N-[[(5S)-3-(1-cyclopropyl-7-fluoro-2-oxo-3H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate carbonyl dichloride Chemical compound C(=O)(Cl)Cl.C(C)(C)(C)OC(NC[C@H]1CN(C(O1)=O)C=1C=C2CC(N(C2=C(C1)F)C1CC1)=O)=O UJMYZAYRKMULLR-UQKRIMTDSA-N 0.000 description 1
- KEIIOKXOKJWFAI-ZOWNYOTGSA-N tert-butyl N-[[(5S)-3-(1-ethyl-7-fluoro-2-oxo-3H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate carbonyl dichloride Chemical compound C(=O)(Cl)Cl.C(C)(C)(C)OC(NC[C@H]1CN(C(O1)=O)C=1C=C2CC(N(C2=C(C1)F)CC)=O)=O KEIIOKXOKJWFAI-ZOWNYOTGSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YGCLIPSOSCUQIT-CQSZACIVSA-N tert-butyl n-[(2r)-3-[(1-cyclopropyl-7-fluoro-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound C1=2C(F)=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC=2CC(=O)N1C1CC1 YGCLIPSOSCUQIT-CQSZACIVSA-N 0.000 description 1
- HNRNBWFGROREEV-CQSZACIVSA-N tert-butyl n-[(2r)-3-[(7-fluoro-2-oxo-1-propyl-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC(F)=C2N(CCC)C(=O)CC2=C1 HNRNBWFGROREEV-CQSZACIVSA-N 0.000 description 1
- VBLBMUZMFMXIJD-OAHLLOKOSA-N tert-butyl n-[(2r)-3-[[1-(cyclopropylmethyl)-7-fluoro-2-oxo-3h-indol-5-yl]amino]-2-hydroxypropyl]carbamate Chemical compound C1=2C(F)=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC=2CC(=O)N1CC1CC1 VBLBMUZMFMXIJD-OAHLLOKOSA-N 0.000 description 1
- ASWYDKGGNIWGIM-ZDUSSCGKSA-N tert-butyl n-[[(5s)-3-[7-fluoro-1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CNC(=O)OC(C)(C)C)CN1C(C=C1F)=CC2=C1N(CCF)C(=O)C2 ASWYDKGGNIWGIM-ZDUSSCGKSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
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- 230000036964 tight binding Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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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
- C07D413/04—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66871505P | 2005-04-06 | 2005-04-06 | |
| US60/668,715 | 2005-04-06 | ||
| US68403305P | 2005-05-24 | 2005-05-24 | |
| US60/684,033 | 2005-05-24 | ||
| PCT/IB2006/000954 WO2006106427A1 (en) | 2005-04-06 | 2006-03-27 | 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2603899A1 true CA2603899A1 (en) | 2006-10-12 |
Family
ID=36636389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002603899A Abandoned CA2603899A1 (en) | 2005-04-06 | 2006-03-27 | 7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7435751B2 (https=) |
| EP (1) | EP1869030A1 (https=) |
| JP (1) | JP2008534672A (https=) |
| KR (1) | KR20070108938A (https=) |
| AP (1) | AP2007004172A0 (https=) |
| AR (1) | AR053839A1 (https=) |
| AU (1) | AU2006231919A1 (https=) |
| BR (1) | BRPI0610533A2 (https=) |
| CA (1) | CA2603899A1 (https=) |
| CR (1) | CR9417A (https=) |
| DO (1) | DOP2006000080A (https=) |
| GT (1) | GT200600133A (https=) |
| IL (1) | IL186119A0 (https=) |
| MX (1) | MX2007012386A (https=) |
| NL (1) | NL1031525C2 (https=) |
| NO (1) | NO20075505L (https=) |
| PE (1) | PE20061301A1 (https=) |
| TN (1) | TNSN07373A1 (https=) |
| TW (1) | TW200716101A (https=) |
| UY (1) | UY29452A1 (https=) |
| WO (1) | WO2006106427A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1781642A1 (en) * | 2004-08-06 | 2007-05-09 | Pharmacia & Upjohn Company LLC | Oxazolidinones containing oxindoles as antibacterial agents |
| KR100891485B1 (ko) | 2007-10-29 | 2009-04-02 | 주식회사 만도 | 디스크 브레이크의 주차브레이크 장치 |
| US20090124737A1 (en) * | 2007-11-12 | 2009-05-14 | Eastman Chemical Company | Acrylic plastisol viscosity reducers |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164510A (en) * | 1988-09-15 | 1992-11-17 | The Upjohn Company | 5'Indolinyl-5β-amidomethyloxazolidin-2-ones |
| JP2865211B2 (ja) | 1988-09-15 | 1999-03-08 | ファルマシア・アンド・アップジョン・カンパニー | ５’―インドリニル―５β―アミドメチルオキサゾリジン―２―オン類、３―（縮合環置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類および３―（窒素原子置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類 |
| DE4425612A1 (de) | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| DE4425613A1 (de) | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| US6015429A (en) * | 1994-09-08 | 2000-01-18 | Gore Enterprise Holdings, Inc. | Procedures for introducing stents and stent-grafts |
| DE19604223A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
| DE19649095A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue Heteroaryl-Oxazolidinone |
| BR9907183A (pt) | 1998-01-23 | 2003-06-10 | Versicor Inc | Colet neas combinatórias de oxazolidinona, composições e processos de preparação |
| DE69912264T2 (de) | 1998-04-14 | 2004-07-22 | Samsung Fine Chemicals Co., Ltd. | Verfahren zur herstellung chiraler (s)-2,3-disubstituierter 1-propylamin-derivate |
| AU1379900A (en) | 1998-11-17 | 2000-06-05 | Bayer Aktiengesellschaft | Novel substituted phenyloxazolidone derivatives |
| HK1040707A1 (zh) | 1998-11-27 | 2002-06-21 | 法玛西雅厄普约翰美国公司 | 具有硫代羰基官能團的噁唑烷酮抗菌劑 |
| 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 |
| ES2256318T3 (es) | 2000-10-17 | 2006-07-16 | PHARMACIA & UPJOHN COMPANY LLC | Metodos de produccion de compuestos de oxazolidinona. |
| DE60212959T2 (de) | 2001-04-07 | 2007-02-15 | Astrazeneca Ab | Eine sulfonimid-gruppe enthaltende oxazolidinone als antibiotika |
| AU2002255803B2 (en) | 2001-04-20 | 2008-07-03 | Pharmacia And Upjohn Company | Process to prepare oxazolidinones |
| AR038536A1 (es) | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| US7012088B2 (en) * | 2003-02-24 | 2006-03-14 | Pharmacia & Upjohn Company | Indolone oxazolidinones and derivatives thereof |
| EP1781642A1 (en) * | 2004-08-06 | 2007-05-09 | Pharmacia & Upjohn Company LLC | Oxazolidinones containing oxindoles as antibacterial agents |
-
2006
- 2006-03-26 AU AU2006231919A patent/AU2006231919A1/en not_active Abandoned
- 2006-03-27 JP JP2008504870A patent/JP2008534672A/ja not_active Withdrawn
- 2006-03-27 CA CA002603899A patent/CA2603899A1/en not_active Abandoned
- 2006-03-27 EP EP06727519A patent/EP1869030A1/en not_active Withdrawn
- 2006-03-27 KR KR1020077022657A patent/KR20070108938A/ko not_active Ceased
- 2006-03-27 MX MX2007012386A patent/MX2007012386A/es unknown
- 2006-03-27 BR BRPI0610533-5A patent/BRPI0610533A2/pt not_active Application Discontinuation
- 2006-03-27 WO PCT/IB2006/000954 patent/WO2006106427A1/en not_active Ceased
- 2006-03-27 AP AP2007004172A patent/AP2007004172A0/xx unknown
- 2006-03-30 US US11/393,961 patent/US7435751B2/en not_active Expired - Fee Related
- 2006-04-04 TW TW095112018A patent/TW200716101A/zh unknown
- 2006-04-04 AR ARP060101328A patent/AR053839A1/es unknown
- 2006-04-04 PE PE2006000363A patent/PE20061301A1/es not_active Application Discontinuation
- 2006-04-04 UY UY29452A patent/UY29452A1/es not_active Application Discontinuation
- 2006-04-05 DO DO2006000080A patent/DOP2006000080A/es unknown
- 2006-04-05 GT GT200600133A patent/GT200600133A/es unknown
- 2006-04-05 NL NL1031525A patent/NL1031525C2/nl not_active IP Right Cessation
-
2007
- 2007-09-20 IL IL186119A patent/IL186119A0/en unknown
- 2007-10-05 TN TNP2007000373A patent/TNSN07373A1/fr unknown
- 2007-10-05 CR CR9417A patent/CR9417A/es unknown
- 2007-10-31 NO NO20075505A patent/NO20075505L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CR9417A (es) | 2007-12-04 |
| JP2008534672A (ja) | 2008-08-28 |
| MX2007012386A (es) | 2007-11-07 |
| GT200600133A (es) | 2006-11-29 |
| WO2006106427A8 (en) | 2007-12-06 |
| AR053839A1 (es) | 2007-05-23 |
| KR20070108938A (ko) | 2007-11-13 |
| US7435751B2 (en) | 2008-10-14 |
| NO20075505L (no) | 2007-10-31 |
| US20060229349A1 (en) | 2006-10-12 |
| NL1031525A1 (nl) | 2006-10-09 |
| AP2007004172A0 (en) | 2007-10-31 |
| AU2006231919A1 (en) | 2006-10-12 |
| NL1031525C2 (nl) | 2007-01-30 |
| UY29452A1 (es) | 2006-11-30 |
| EP1869030A1 (en) | 2007-12-26 |
| TNSN07373A1 (fr) | 2009-03-17 |
| DOP2006000080A (es) | 2006-12-15 |
| TW200716101A (en) | 2007-05-01 |
| IL186119A0 (en) | 2008-01-20 |
| BRPI0610533A2 (pt) | 2010-06-29 |
| WO2006106427A1 (en) | 2006-10-12 |
| PE20061301A1 (es) | 2007-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |