CA2610978A1 - Homomorpholine oxazolidinones as antibacterial agents - Google Patents
Homomorpholine oxazolidinones as antibacterial agents Download PDFInfo
- Publication number
- CA2610978A1 CA2610978A1 CA002610978A CA2610978A CA2610978A1 CA 2610978 A1 CA2610978 A1 CA 2610978A1 CA 002610978 A CA002610978 A CA 002610978A CA 2610978 A CA2610978 A CA 2610978A CA 2610978 A1 CA2610978 A1 CA 2610978A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- oxazepan
- phenyl
- oxo
- oxazolidine
- 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
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- YKNYRRVISWJDSR-GSVOUGTGSA-N methyl (2r)-oxirane-2-carboxylate Chemical compound COC(=O)[C@H]1CO1 YKNYRRVISWJDSR-GSVOUGTGSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 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
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-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
- 229960003732 tyramine Drugs 0.000 description 1
- 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
- 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
- C07D413/10—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69486205P | 2005-06-29 | 2005-06-29 | |
| US60/694,862 | 2005-06-29 | ||
| PCT/IB2006/001730 WO2007000644A1 (en) | 2005-06-29 | 2006-06-20 | Homomorpholine oxazolidinones as antibacterial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2610978A1 true CA2610978A1 (en) | 2007-01-04 |
Family
ID=37101665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002610978A Abandoned CA2610978A1 (en) | 2005-06-29 | 2006-06-20 | Homomorpholine oxazolidinones as antibacterial agents |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1899331B1 (enExample) |
| JP (1) | JP2008544979A (enExample) |
| AT (1) | ATE449773T1 (enExample) |
| CA (1) | CA2610978A1 (enExample) |
| DE (1) | DE602006010702D1 (enExample) |
| DK (1) | DK1899331T3 (enExample) |
| ES (1) | ES2335307T3 (enExample) |
| WO (1) | WO2007000644A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP5455906B2 (ja) * | 2007-08-06 | 2014-03-26 | ミクウルク ファーマシューティカルズ，インコーポレイテッド | 細菌感染症治療のための抗微生物性オルト−フルオロフェニルオキサゾリジノン |
| EP2669283A1 (en) * | 2007-10-02 | 2013-12-04 | Shionogi&Co., Ltd. | Oxazolidinone derivative having 7-membered hetero ring |
| CA2939098A1 (en) | 2014-02-21 | 2015-08-27 | Micurx Pharmaceuticals, Inc. | Water-soluble o-carbonyl phosphoramidate prodrugs for therapeutic administration |
| CN113603683B (zh) * | 2015-07-17 | 2024-06-14 | 结核病药物开发全球联盟公司 | 用于抗微生物治疗的经取代苯基噁唑烷酮 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK283420B6 (sk) | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| US5952324A (en) | 1994-11-15 | 1999-09-14 | Pharmacia & Upjohn Company | Bicyclic oxazine and thiazine oxazolidinone antibacterials |
| CN1154644C (zh) | 1997-11-12 | 2004-06-23 | 法玛西雅厄普约翰美国公司 | 噁唑烷酮衍生物和药物组合物 |
| JP2000204084A (ja) | 1998-11-11 | 2000-07-25 | Hokuriku Seiyaku Co Ltd | チオカルバミド酸誘導体 |
| 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 |
| US6297242B1 (en) | 1999-08-12 | 2001-10-02 | Ortho-Mcneil Pharmaceutical, Inc. | N-substituted amidine and guanidine oxazolidinone antibacterials and methods of use thereof |
| SK7572002A3 (en) | 1999-12-21 | 2002-12-03 | Upjohn Co | Oxazolidinones having a sulfoximine functionality and their use as antimicrobial agents |
| AU2001253113B2 (en) | 2000-04-20 | 2005-02-03 | Pharmacia & Upjohn Company | Use of thioamide oxazolidinones for the treatment of bone resorption and osteoporosis |
| ATE301474T1 (de) | 2000-06-30 | 2005-08-15 | Pharmacia & Upjohn Co Llc | Zusammensetzungen zur behandlung baktrieller infektionen, welche ein oxazolidinonderivat, sulbactam und ampicillin enthalten |
| GB0017225D0 (en) | 2000-07-14 | 2000-08-30 | Really Useful Products Limited | Container |
| DE10034627A1 (de) | 2000-07-17 | 2002-01-31 | Bayer Ag | Aryl-substituierte Oxazolidinone mit Cytokin inhibitorischer Wirkung |
| HUP0302918A2 (hu) | 2000-07-17 | 2003-12-29 | Ranbaxy Laboratories Limited | Mikrobaellenes oxazolidinonszármazékok és a vegyületeket tartalmazó gyógyászati készítmények és eljárás a vegyületek előállítására |
| DE60144522D1 (de) | 2000-08-24 | 2011-06-09 | Sirf Tech Inc | Vorrichtung zur reduzierung von autokorrelation und kreuzkorrelation bei schwachen cdma-signalen |
| PE20020578A1 (es) | 2000-10-10 | 2002-08-14 | Upjohn Co | Una composicion de antibiotico topico para el tratamiento de infecciones oculares |
| US20030008012A1 (en) | 2001-02-05 | 2003-01-09 | Pena Lorraine E. | Composition for rectal delivery of an oxazolidinone antibacterial drug |
| DE10105989A1 (de) | 2001-02-09 | 2002-08-14 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| ES2268011T3 (es) | 2001-04-07 | 2007-03-16 | Astrazeneca Ab | Oxazolidinonas que contienen un grupo sulfonimida como antibioticos. |
| GB0108793D0 (en) | 2001-04-07 | 2001-05-30 | Astrazeneca Ab | Chemical compounds |
| EP1409464A4 (en) | 2001-07-16 | 2005-11-02 | Ranbaxy Lab Ltd | OXAZOLIDINONE DERIVATIVES AS POTENTIAL ANTIMICROBIALS |
| US6956040B2 (en) | 2001-07-16 | 2005-10-18 | Ranbaxy Laboratories Limited | Oxazolidinone piperazinyl derivatives as potential antimicrobials |
| TW200302095A (en) | 2002-01-25 | 2003-08-01 | Upjohn Co | Oxazolidinone cotherapy |
| TW200400055A (en) | 2002-02-22 | 2004-01-01 | Pharmacia Corp | Ophthalmic formulation with novel gum composition |
| WO2003072141A1 (en) | 2002-02-22 | 2003-09-04 | Pharmacia Corporation | Ophthalmic antibiotic drug formulations containing a cyclodextrin compound and cetyl pyridinium chloride |
| AR038536A1 (es) | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| KR20040086465A (ko) | 2002-02-28 | 2004-10-08 | 아스트라제네카 아베 | 화합물 |
| AU2003207340A1 (en) | 2002-02-28 | 2003-09-09 | Astrazeneca Ab | 3-cyclyl-5-(nitrogen-containing 5-membered ring) methyl-oxazolidinone derivatives and their use as antibacterial agents |
| EP1490059A1 (en) | 2002-03-29 | 2004-12-29 | Pharmacia & Upjohn Company LLC | Parenteral, intravenous, and oral administration of oxazolidinones for treating diabetic foot infections |
| AU2003224345A1 (en) | 2002-04-30 | 2003-11-17 | Orchid Chemicals & Pharmaceuticals | Antibacterial agents |
| TW200403240A (en) | 2002-06-28 | 2004-03-01 | Upjohn Co | Difluorothioacetamides of oxazolidinones as antibacterial agents |
| WO2004009587A1 (en) | 2002-07-22 | 2004-01-29 | Orchid Chemicals & Pharmaceuticals Ltd | Oxazolidinone derivatives as antibacterial agents |
| EA200500283A1 (ru) | 2002-07-29 | 2005-08-25 | Рэнбакси Лабораториз Лимитед | Производные оксазолидинона как противомикробные средства |
| AU2003253141A1 (en) | 2002-08-22 | 2004-03-11 | Orchid Chemicals And Pharmaceuticals Ltd | Novel antibacterial agents |
-
2006
- 2006-06-20 JP JP2008518998A patent/JP2008544979A/ja not_active Withdrawn
- 2006-06-20 WO PCT/IB2006/001730 patent/WO2007000644A1/en not_active Ceased
- 2006-06-20 AT AT06779767T patent/ATE449773T1/de not_active IP Right Cessation
- 2006-06-20 ES ES06779767T patent/ES2335307T3/es active Active
- 2006-06-20 DE DE602006010702T patent/DE602006010702D1/de active Active
- 2006-06-20 EP EP06779767A patent/EP1899331B1/en not_active Not-in-force
- 2006-06-20 CA CA002610978A patent/CA2610978A1/en not_active Abandoned
- 2006-06-20 DK DK06779767.0T patent/DK1899331T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| DK1899331T3 (da) | 2010-03-08 |
| JP2008544979A (ja) | 2008-12-11 |
| ES2335307T3 (es) | 2010-03-24 |
| DE602006010702D1 (de) | 2010-01-07 |
| WO2007000644A1 (en) | 2007-01-04 |
| EP1899331B1 (en) | 2009-11-25 |
| ATE449773T1 (de) | 2009-12-15 |
| EP1899331A1 (en) | 2008-03-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |