CA2330619A1 - N1-modified glycopeptides - Google Patents
N1-modified glycopeptides Download PDFInfo
- Publication number
- CA2330619A1 CA2330619A1 CA002330619A CA2330619A CA2330619A1 CA 2330619 A1 CA2330619 A1 CA 2330619A1 CA 002330619 A CA002330619 A CA 002330619A CA 2330619 A CA2330619 A CA 2330619A CA 2330619 A1 CA2330619 A1 CA 2330619A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- phenyl
- amino acid
- substituted
- alpha
- 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
- 108010015899 Glycopeptides Proteins 0.000 title claims description 6
- 102000002068 Glycopeptides Human genes 0.000 title claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 13
- 229940024606 amino acid Drugs 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- -1 p-biphenylyl Chemical group 0.000 claims description 6
- 125000006187 phenyl benzyl group Chemical group 0.000 claims description 6
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 125000001475 halogen functional group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- XJODGRWDFZVTKW-ZCFIWIBFSA-N n-methylleucine Chemical compound CN[C@@H](C(O)=O)CC(C)C XJODGRWDFZVTKW-ZCFIWIBFSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 claims description 3
- 108010059993 Vancomycin Proteins 0.000 claims description 3
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims description 3
- 229960003165 vancomycin Drugs 0.000 claims description 3
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 2
- NIGWMJHCCYYCSF-UHFFFAOYSA-N Fenclonine Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1 NIGWMJHCCYYCSF-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004473 Threonine Substances 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229960003767 alanine Drugs 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229960003121 arginine Drugs 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 235000009697 arginine Nutrition 0.000 claims description 2
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- 235000009582 asparagine Nutrition 0.000 claims description 2
- 229960005261 aspartic acid Drugs 0.000 claims description 2
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229960002433 cysteine Drugs 0.000 claims description 2
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- 238000009472 formulation Methods 0.000 claims description 2
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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- 238000006731 degradation reaction Methods 0.000 description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 241000192125 Firmicutes Species 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8387998P | 1998-05-01 | 1998-05-01 | |
| US60/083,879 | 1998-05-01 | ||
| PCT/US1999/004306 WO1999056760A1 (en) | 1998-05-01 | 1999-02-26 | N1-modified glycopeptides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2330619A1 true CA2330619A1 (en) | 1999-11-11 |
Family
ID=22181253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002330619A Abandoned CA2330619A1 (en) | 1998-05-01 | 1999-02-26 | N1-modified glycopeptides |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US6670446B1 (https=) |
| EP (1) | EP1073447B1 (https=) |
| JP (1) | JP4307723B2 (https=) |
| AT (1) | ATE361931T1 (https=) |
| AU (1) | AU2881399A (https=) |
| CA (1) | CA2330619A1 (https=) |
| DE (1) | DE69936052T2 (https=) |
| DK (1) | DK1073447T3 (https=) |
| ES (1) | ES2283107T3 (https=) |
| WO (1) | WO1999056760A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999056760A1 (en) * | 1998-05-01 | 1999-11-11 | Eli Lilly And Company | N1-modified glycopeptides |
| PT1140993E (pt) | 1998-12-23 | 2003-10-31 | Theravance Inc | Derivados de glicopeptidos e composicoes farmaceuticas contendo os mesmos |
| US6699836B2 (en) | 1999-04-02 | 2004-03-02 | The Trustees Of Princeton University | Vancomycin analogs |
| US6518243B1 (en) | 1999-04-02 | 2003-02-11 | Trustees Of Princeton University | Desleucyl glycopeptide antibiotics and methods of making same |
| CA2399640A1 (en) | 2000-02-11 | 2001-08-16 | Eli Lilly And Company | Selective n-acylation of a82846 glycopeptide analogs |
| AR053347A1 (es) | 2005-04-06 | 2007-05-02 | Astrazeneca Ab | Derivados de [1,3]tiazolo[4,5-d]pirimidin-2(3h)-ona 5,7-sustituidos |
| UA90707C2 (en) | 2005-04-06 | 2010-05-25 | Астразенека Аб | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
| CA2623198C (en) | 2005-09-22 | 2014-08-05 | Medivas, Llc | Bis-(a-amino)-diol-diester-containing poly(ester amide) and poly(ester urethane) compositions and methods of use |
| JP5178520B2 (ja) | 2005-09-22 | 2013-04-10 | メディバス エルエルシー | 固体ポリマー送達組成物およびその使用法 |
| EP2260060A4 (en) | 2008-04-01 | 2013-01-16 | Univ Cornell | ORGANIC SOLUBLE CHITOSA SALT AND CHITOSAN DERIVED BIOMATERIALS MANUFACTURED THEREFROM |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4698327A (en) | 1985-04-25 | 1987-10-06 | Eli Lilly And Company | Novel glycopeptide derivatives |
| US4639433A (en) | 1985-08-14 | 1987-01-27 | Eli Lilly And Company | Glycopeptide derivatives |
| US4643987A (en) | 1985-08-14 | 1987-02-17 | Eli Lilly And Company | Modified glycopeptides |
| EG18377A (en) * | 1986-09-19 | 1993-04-30 | Lilly Co Eli | Process for preparing glycopeptide antibiotics |
| US5534420A (en) | 1988-07-28 | 1996-07-09 | Eli Lilly And Company | Biotransformation of glycopeptide antibiotics |
| ZA909847B (en) | 1989-12-13 | 1992-08-26 | Lilly Co Eli | Glycopeptide derivatives |
| TW457248B (en) | 1994-01-28 | 2001-10-01 | Lilly Co Eli | Glycopeptide antibiotic derivatives |
| US5952310A (en) * | 1997-05-20 | 1999-09-14 | Eli Lilly And Company | Glycopeptide hexapeptides |
| WO1999056760A1 (en) * | 1998-05-01 | 1999-11-11 | Eli Lilly And Company | N1-modified glycopeptides |
-
1999
- 1999-02-26 WO PCT/US1999/004306 patent/WO1999056760A1/en not_active Ceased
- 1999-02-26 DK DK99909654T patent/DK1073447T3/da active
- 1999-02-26 CA CA002330619A patent/CA2330619A1/en not_active Abandoned
- 1999-02-26 EP EP99909654A patent/EP1073447B1/en not_active Expired - Lifetime
- 1999-02-26 AT AT99909654T patent/ATE361931T1/de not_active IP Right Cessation
- 1999-02-26 US US09/647,113 patent/US6670446B1/en not_active Expired - Fee Related
- 1999-02-26 AU AU28813/99A patent/AU2881399A/en not_active Abandoned
- 1999-02-26 ES ES99909654T patent/ES2283107T3/es not_active Expired - Lifetime
- 1999-02-26 DE DE69936052T patent/DE69936052T2/de not_active Expired - Fee Related
- 1999-02-26 JP JP2000546785A patent/JP4307723B2/ja not_active Expired - Fee Related
-
2003
- 2003-11-18 US US10/717,163 patent/US6939947B2/en not_active Expired - Fee Related
-
2005
- 2005-09-02 US US11/219,523 patent/US20060128609A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE361931T1 (de) | 2007-06-15 |
| DE69936052T2 (de) | 2008-01-17 |
| US6939947B2 (en) | 2005-09-06 |
| US20060128609A1 (en) | 2006-06-15 |
| EP1073447B1 (en) | 2007-05-09 |
| EP1073447A1 (en) | 2001-02-07 |
| JP2002513764A (ja) | 2002-05-14 |
| EP1073447A4 (en) | 2001-10-04 |
| US6670446B1 (en) | 2003-12-30 |
| WO1999056760A1 (en) | 1999-11-11 |
| ES2283107T3 (es) | 2007-10-16 |
| US20050037950A1 (en) | 2005-02-17 |
| JP4307723B2 (ja) | 2009-08-05 |
| DK1073447T3 (da) | 2007-09-03 |
| AU2881399A (en) | 1999-11-23 |
| DE69936052D1 (de) | 2007-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |