ES2217406T3 - 2,3-benzodiazepin-4-onas sustituidas y su uso. - Google Patents
2,3-benzodiazepin-4-onas sustituidas y su uso.Info
- Publication number
- ES2217406T3 ES2217406T3 ES97916722T ES97916722T ES2217406T3 ES 2217406 T3 ES2217406 T3 ES 2217406T3 ES 97916722 T ES97916722 T ES 97916722T ES 97916722 T ES97916722 T ES 97916722T ES 2217406 T3 ES2217406 T3 ES 2217406T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- benzodiazepin
- dihydro
- methylenedioxy
- substituted
- 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.)
- Expired - Lifetime
Links
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- ZREPCAXZLIBMDG-UHFFFAOYSA-N methyl 2-[6-(2-chloro-4-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1Cl ZREPCAXZLIBMDG-UHFFFAOYSA-N 0.000 description 1
- CHWTWRBHKJJMHW-UHFFFAOYSA-N methyl 2-[6-(3-methoxy-4-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=C([N+]([O-])=O)C(OC)=C1 CHWTWRBHKJJMHW-UHFFFAOYSA-N 0.000 description 1
- IEMQDQVIQIMCLA-UHFFFAOYSA-N methyl 2-[6-(3-methyl-4-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=C([N+]([O-])=O)C(C)=C1 IEMQDQVIQIMCLA-UHFFFAOYSA-N 0.000 description 1
- VPJNVZORYJEMOC-UHFFFAOYSA-N methyl 2-[6-(3-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=CC([N+]([O-])=O)=C1 VPJNVZORYJEMOC-UHFFFAOYSA-N 0.000 description 1
- JSCZANNMYBUKJA-UHFFFAOYSA-N methyl 2-[6-(4-fluorobenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=C(F)C=C1 JSCZANNMYBUKJA-UHFFFAOYSA-N 0.000 description 1
- NGXNADOTFBPSML-UHFFFAOYSA-N methyl 2-[6-(4-methoxybenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=C(OC)C=C1 NGXNADOTFBPSML-UHFFFAOYSA-N 0.000 description 1
- XTWPYPVQQFQLDB-UHFFFAOYSA-N methyl 2-[6-(4-methylbenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=C(C)C=C1 XTWPYPVQQFQLDB-UHFFFAOYSA-N 0.000 description 1
- XAIMYQGVNXSMPS-UHFFFAOYSA-N methyl 2-[6-(4-nitrobenzoyl)-1,3-benzodioxol-5-yl]acetate Chemical compound COC(=O)CC1=CC=2OCOC=2C=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 XAIMYQGVNXSMPS-UHFFFAOYSA-N 0.000 description 1
- HYDHNYHBKZFKBA-UHFFFAOYSA-N methyl 2-[6-(4-nitrobenzoyl)-1,3-benzodioxol-5-yl]propanoate Chemical compound COC(=O)C(C)C1=CC=2OCOC=2C=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 HYDHNYHBKZFKBA-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
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- 230000007625 mitochondrial abnormality Effects 0.000 description 1
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- 210000003205 muscle Anatomy 0.000 description 1
- XAWRFNNHUHTBGT-UHFFFAOYSA-N n-[4-(8-oxo-7,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(C1=C2)=NNC(=O)CC1=CC1=C2OCO1 XAWRFNNHUHTBGT-UHFFFAOYSA-N 0.000 description 1
- KGVROGWGQGUTCZ-UHFFFAOYSA-N n-methyl-8-oxo-5-phenyl-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-7-carboxamide Chemical compound C12=CC=3OCOC=3C=C2CC(=O)N(C(=O)NC)N=C1C1=CC=CC=C1 KGVROGWGQGUTCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 230000003705 neurological process Effects 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
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- 230000002085 persistent effect Effects 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003906 phosphoinositides Chemical class 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/02—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1381396P | 1996-03-21 | 1996-03-21 | |
| US13813P | 1996-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2217406T3 true ES2217406T3 (es) | 2004-11-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97916722T Expired - Lifetime ES2217406T3 (es) | 1996-03-21 | 1997-03-21 | 2,3-benzodiazepin-4-onas sustituidas y su uso. |
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|---|---|
| US (1) | US5891871A (enExample) |
| EP (1) | EP1021418B1 (enExample) |
| JP (1) | JP2000506890A (enExample) |
| AT (1) | ATE267177T1 (enExample) |
| AU (1) | AU2527097A (enExample) |
| DE (1) | DE69729227T2 (enExample) |
| DK (1) | DK1021418T3 (enExample) |
| ES (1) | ES2217406T3 (enExample) |
| PT (1) | PT1021418E (enExample) |
| WO (1) | WO1997034878A1 (enExample) |
| ZA (1) | ZA972496B (enExample) |
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| DE19604920A1 (de) * | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| DE19604919A1 (de) | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| US6635632B1 (en) * | 1996-12-23 | 2003-10-21 | Athena Neurosciences, Inc. | Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds |
| HU227128B1 (en) * | 1999-07-07 | 2010-07-28 | Egyt Gyogyszervegyeszeti Gyar | New 2,3-benzodiazepine derivatives |
| DE10004572A1 (de) * | 2000-02-02 | 2001-08-09 | Boehringer Ingelheim Pharma | Neue positive allosterische AMPA-Rezeptor Modulatoren (PAARM), Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| PT1300396E (pt) | 2000-06-12 | 2009-04-20 | Eisai R&D Man Co Ltd | Compostos de 1,2-di-hidropiridina, processos para a sua preparação e sua utilização |
| US6432944B1 (en) | 2000-07-06 | 2002-08-13 | Bristol-Myers Squibb Company | Benzodiazepinone β-amyloid inhibitors: arylacetamidoalanyl derivatives |
| HU225100B1 (hu) * | 2000-12-21 | 2006-06-28 | Egyt Gyogyszervegyeszeti Gyar | 2,3-Benzodiazepinszármazékok, ilyen hatóanyagot tartalmazó gyógyászati készítmények és alkalmazásuk |
| US6649607B2 (en) * | 2001-05-18 | 2003-11-18 | Vela Pharmaceuticals, Inc. | Compositions and methods for treating or preventing convulsions or seizures |
| EP1392663A2 (fr) * | 2001-06-07 | 2004-03-03 | Neuro3D | Inhibiteurs des phosphodiesterases des nucleotides cycliques, preparation et utilisations de ces inhibiteurs |
| GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| JP2006510634A (ja) * | 2002-12-03 | 2006-03-30 | ヴェラ ファーマスーティカルズ インコーポレイテッド | １−（３，４−ジメトキシフェニル）−４−メチル−５−エチル−７−メトキシ−８−ヒドロキシ−５ｈ−２，３−ベンゾジアゼピンの製薬組成物及びその用途 |
| US20040152695A1 (en) * | 2002-12-03 | 2004-08-05 | Vela Pharmaceuticals, Inc. | Pharmaceutical composition of 1-(3-hydroxy-4-methoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine and uses thereof |
| US6638928B1 (en) | 2002-12-03 | 2003-10-28 | Vela Pharmaceuticals, Inc. | Treatment of irritable bowel syndrome and nonulcer dyspepsia with substituted 2,3-benzodiazepines |
| US7022700B2 (en) * | 2002-12-03 | 2006-04-04 | Vela Pharmaceuticals, Inc. | Method of increasing neutrophil production using optically-pure (R)-2,3-benzodiazepines |
| US6864251B2 (en) * | 2002-12-03 | 2005-03-08 | Vela Pharmaceuticals, Inc. | Treatment of LTB4-mediated inflammatory disorders with optically-pure (R)-2,3-benzodiazepines |
| WO2004062616A2 (en) | 2003-01-13 | 2004-07-29 | Cortex Pharmaceuticals, Inc. | Method of treating cognitive decline due to sleep deprivation and stress |
| US20040152694A1 (en) * | 2003-02-04 | 2004-08-05 | Istvan Kurucz | Methods and compositions for treating inflammatory disorders of the airways |
| US20040224943A1 (en) * | 2003-02-19 | 2004-11-11 | Leventer Steven M. | Method of lowering body temperature with (R) - 2,3-benzodiazepines |
| US20040162284A1 (en) * | 2003-02-19 | 2004-08-19 | Harris Herbert W. | Method of lowering body temperature with (S) tofisopam |
| GB0325175D0 (en) * | 2003-10-28 | 2003-12-03 | Novartis Ag | Organic compounds |
| MY148809A (en) | 2004-07-06 | 2013-05-31 | Eisai R&D Man Co Ltd | Crystals of 1,2-dihydropyridine compound and their production process |
| JP2007153755A (ja) * | 2005-12-01 | 2007-06-21 | Gifu Univ | プロリン類縁体 |
| EP2338492A1 (en) | 2009-12-24 | 2011-06-29 | Universidad del Pais Vasco | Methods and compositions for the treatment of alzheimer |
| FR2972454B1 (fr) * | 2011-03-08 | 2013-03-01 | Servier Lab | Nouveaux derives dihydro-oxazolobenzodiazepinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PE20150729A1 (es) | 2012-08-16 | 2015-06-14 | Bayer Pharma AG | 2,3-benzodiazepines |
| CA2901352A1 (en) | 2013-02-19 | 2014-08-28 | Bayer Pharma Aktiengesellschaft | Bicyclo 2,3-benzodiazepines and spirocyclically substituted 2,3-benzodiazepines |
| HK1212345A1 (en) | 2013-02-22 | 2016-06-10 | Bayer Pharma Aktiengesellschaft | 4-substituted pyrrolo- and pyrazolo-diazepines |
| JP2016513117A (ja) | 2013-02-22 | 2016-05-12 | バイエル ファーマ アクチエンゲゼルシャフト | 過剰増殖性疾患を治療するためのｂｅｔタンパク質阻害剤としてのピロロ−およびピラゾロ−トリアゾロジアゼピン類 |
| BR112015031249A2 (pt) | 2013-06-13 | 2017-07-25 | Veroscience Llc | método de tratamento, método para tratar um distúrbio metabólico ou um elemento chave do mesmo, método para normalizar um ritmo diário de liberação de dopamina no sumn, método para estimular a liberação de dopamina de neurônios dopaminérgicos no sumn de um indivíduo e composição farmacêutica |
| US20190112300A1 (en) | 2016-03-29 | 2019-04-18 | Arnold Stan Lippa | Compositions And Methods For Treating Attention Deficit Disorders |
| CN113226286B (zh) | 2018-12-14 | 2024-08-20 | 卫材R&D管理有限公司 | 1,2-二氢吡啶化合物的水基药物制剂 |
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| FR2085645A1 (en) * | 1970-04-22 | 1971-12-31 | Chimidrog | 1-phenyl-2,3-benzodiazepin-4-ones - as tranquillizers |
| HU191698B (en) * | 1984-07-27 | 1987-03-30 | Gyogyszerkutato Intezet | Process for producing new 1-aryl-5h-2beta-benzodiazepines |
| HU198494B (en) * | 1986-08-15 | 1989-10-30 | Gyogyszerkutato Intezet | Process for producing new 3,4-dihydro-5h-2,3-benzodiazepine derivative and acid addition salts thereof, as well as pharmaceutical compositions comprising same |
| HU219778B (hu) * | 1990-12-21 | 2001-07-30 | Gyógyszerkutató Intézet Közös Vállalat | Eljárás N-acil-2,3-benzodiazepin-származékok, savaddíciós sóik és az ezeket tartalmazó gyógyászati készítmények előállítására, valamint a vegyületek egy csoportja, és az ezeket tartalmazó gyógyászati készítmények |
| US5550124A (en) * | 1991-12-10 | 1996-08-27 | University Of Southern California | Use of peripheral-type benzodiazpine sites for treatment of CNS trauma or disease |
| US5922773A (en) * | 1992-12-04 | 1999-07-13 | The Children's Medical Center Corp. | Glaucoma treatment |
| DE19604920A1 (de) * | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
-
1997
- 1997-03-20 US US08/821,638 patent/US5891871A/en not_active Expired - Fee Related
- 1997-03-21 ES ES97916722T patent/ES2217406T3/es not_active Expired - Lifetime
- 1997-03-21 PT PT97916722T patent/PT1021418E/pt unknown
- 1997-03-21 AT AT97916722T patent/ATE267177T1/de not_active IP Right Cessation
- 1997-03-21 DK DK97916722T patent/DK1021418T3/da active
- 1997-03-21 AU AU25270/97A patent/AU2527097A/en not_active Abandoned
- 1997-03-21 DE DE69729227T patent/DE69729227T2/de not_active Expired - Fee Related
- 1997-03-21 WO PCT/US1997/003462 patent/WO1997034878A1/en not_active Ceased
- 1997-03-21 EP EP97916722A patent/EP1021418B1/en not_active Expired - Lifetime
- 1997-03-21 JP JP9533496A patent/JP2000506890A/ja not_active Ceased
- 1997-03-24 ZA ZA9702496A patent/ZA972496B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5891871A (en) | 1999-04-06 |
| ZA972496B (en) | 1997-10-02 |
| EP1021418A1 (en) | 2000-07-26 |
| EP1021418A4 (en) | 2001-06-13 |
| EP1021418B1 (en) | 2004-05-19 |
| JP2000506890A (ja) | 2000-06-06 |
| DE69729227T2 (de) | 2005-05-04 |
| ATE267177T1 (de) | 2004-06-15 |
| WO1997034878A1 (en) | 1997-09-25 |
| DE69729227D1 (de) | 2004-06-24 |
| PT1021418E (pt) | 2004-10-29 |
| DK1021418T3 (da) | 2004-09-20 |
| AU2527097A (en) | 1997-10-10 |
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