AR016387A1 - COMPOUNDS THAT INHIBIT THE ADHESION OF LEUKOCYTES INTERMEDIATED BY VLA-4, METHOD TO ADHER VLA-4 IN A BIOLOGICAL SAMPLE, PHARMACEUTICAL COMPOSITION, METHOD OF TREATMENT WITH SUCH COMPOUNDS - Google Patents
COMPOUNDS THAT INHIBIT THE ADHESION OF LEUKOCYTES INTERMEDIATED BY VLA-4, METHOD TO ADHER VLA-4 IN A BIOLOGICAL SAMPLE, PHARMACEUTICAL COMPOSITION, METHOD OF TREATMENT WITH SUCH COMPOUNDSInfo
- Publication number
- AR016387A1 AR016387A1 ARP980103776A ARP980103776A AR016387A1 AR 016387 A1 AR016387 A1 AR 016387A1 AR P980103776 A ARP980103776 A AR P980103776A AR P980103776 A ARP980103776 A AR P980103776A AR 016387 A1 AR016387 A1 AR 016387A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- heterocyclic
- compounds
- group
- aryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 108010008212 Integrin alpha4beta1 Proteins 0.000 title abstract 4
- 210000000265 leukocyte Anatomy 0.000 title abstract 3
- 239000012472 biological sample Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 14
- 125000001072 heteroaryl group Chemical group 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- 125000003107 substituted aryl group Chemical group 0.000 abstract 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 230000021164 cell adhesion Effects 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 208000027866 inflammatory disease Diseases 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 208000030507 AIDS Diseases 0.000 abstract 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 201000001320 Atherosclerosis Diseases 0.000 abstract 1
- 206010012289 Dementia Diseases 0.000 abstract 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 abstract 1
- 206010027476 Metastases Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 210000004556 brain Anatomy 0.000 abstract 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 230000009401 metastasis Effects 0.000 abstract 1
- 201000006417 multiple sclerosis Diseases 0.000 abstract 1
- 208000031225 myocardial ischemia Diseases 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
-
- 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)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Se describen compuestos que se adhieren a VLA-4. Algunos de estos compuestos inhiben también la adhesion de leucocitos y en particular, la adhesion deleucocitos intermediada por VLA-4. Dichos compuestos son utiles para el tratamiento de enfermedadesinflamatorias en un paciente mamífero, por ejemplo en unser humano, tal como asma, enfermedad de Alzheimer, ateroesclerosis, demencia causada por SIDA, diabetes, enfermedad inflamatoria del intestino, artritisreumatoide, transplantes de tejidos, metástasis de tumores e isquemia de miocardio. Los componentes pueden administrarse también para el tratamiento deenfermedades inflamatorias del cerebro tales como esclerosis multiple. Los compuestos de la formula I donde R1 está seleccionado del grupo que consiste enalquilo, alquilo sustituido, arilo, arilo sustituido, cicloalquilo, cicloalquilo sustituido, heterocíclico, heterocíclico sustituido, heteroarilo yheteroarilo sustituido. R2 está seleccionado del grupo que consiste en hidrogeno, alquilo, alquilo sustituido, cicloalquilo, cicloalquilo sustituido,cicloalquenilo, cicloalquenilo sustituido, heterocíclico, heterocíclico sustituido, arilo, arilo sustituido, heteroarilo, heteroarilo sustituido, y R1 y R2conjuntamente con el átomo de nitrogeno unido a R2 y el grupo SO2 unido a R1 pueden formar un grupo heterocíclico o heterocíclico sustituido; R3 estárelacionado del grupo que consiste en alquilo, alquilo sustituido, cicloalquilo, cicloalquilo sustituido, arilo, arilo sustituido, heteroarilo, heteroarilosustituido, heterocíclico, heterocíclico sustituido y cuando R2 no forma un grupo heterocíclico con R1 y R2 y R3 conjuntamente con el átomo de nitrogenoadherido a R2 y el átomo de carbono adherido a R3, pueden formar un grupo heterocíclico o heterocíclico sustituido; R4 está seleccionado del grupo que consisteen alquilo, alquilo sustituido, arilo, arilo sustituido, heteroarilo, heteroarilo sustituido, y, cuando R3 no forma un grupo heteroc'cilico con R2, entonces R3y R4 conjuntamente con átomo de carbono al cual están unidos pueden formar un cicloalquilo, cicloalquilo sustituido, un heterocíclico o un grupo heterocíclicoCompounds that adhere to VLA-4 are described. Some of these compounds also inhibit white blood cell adhesion and in particular, white blood cell adhesion mediated by VLA-4. Such compounds are useful for the treatment of inflammatory diseases in a mammalian patient, for example in a human being, such as asthma, Alzheimer's disease, atherosclerosis, dementia caused by AIDS, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplants, metastasis of tumors and myocardial ischemia. The components can also be administered for the treatment of inflammatory diseases of the brain such as multiple sclerosis. The compounds of the formula I wherein R 1 is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, heterocyclic, substituted heterocyclic, heteroaryl and substituted heteroaryl. R2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkenyl, substituted cycloalkenyl, heterocyclic, substituted heterocyclic, aryl, substituted aryl, heteroaryl, substituted heteroaryl, and R1 and R2 together with the attached nitrogen atom at R2 and the SO2 group attached to R1 can form a substituted heterocyclic or heterocyclic group; R3 is related to the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryls, heterocyclic, substituted heterocyclic and when R2 does not form a heterocyclic group with R1 and R2 and R3 together with the nitrogen atom attached at R2 and the carbon atom adhered to R3, they can form a substituted heterocyclic or heterocyclic group; R4 is selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, and, when R3 does not form a heterocyclic group with R2, then R3 and R4 together with the carbon atom to which they are attached can form a cycloalkyl, substituted cycloalkyl, a heterocyclic or a heterocyclic group
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90441597A | 1997-07-31 | 1997-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR016387A1 true AR016387A1 (en) | 2001-07-04 |
Family
ID=25419114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP980103776A AR016387A1 (en) | 1997-07-31 | 1998-07-30 | COMPOUNDS THAT INHIBIT THE ADHESION OF LEUKOCYTES INTERMEDIATED BY VLA-4, METHOD TO ADHER VLA-4 IN A BIOLOGICAL SAMPLE, PHARMACEUTICAL COMPOSITION, METHOD OF TREATMENT WITH SUCH COMPOUNDS |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0994895A1 (en) |
| JP (1) | JP2001512137A (en) |
| KR (1) | KR20010022412A (en) |
| CN (1) | CN1265673A (en) |
| AR (1) | AR016387A1 (en) |
| AU (1) | AU8661298A (en) |
| BR (1) | BR9811599A (en) |
| CA (1) | CA2291475A1 (en) |
| HU (1) | HUP0002682A3 (en) |
| IL (1) | IL133642A0 (en) |
| NO (1) | NO20000412L (en) |
| PL (1) | PL338554A1 (en) |
| WO (1) | WO1999006435A1 (en) |
| ZA (1) | ZA986834B (en) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6903075B1 (en) | 1997-05-29 | 2005-06-07 | Merck & Co., Inc. | Heterocyclic amide compounds as cell adhesion inhibitors |
| US6221888B1 (en) | 1997-05-29 | 2001-04-24 | Merck & Co., Inc. | Sulfonamides as cell adhesion inhibitors |
| WO1998053818A1 (en) * | 1997-05-29 | 1998-12-03 | Merck & Co., Inc. | Sulfonamides as cell adhesion inhibitors |
| JP2002501518A (en) * | 1997-05-30 | 2002-01-15 | セルテック セラピューティックス リミテッド | Anti-inflammatory tyrosine derivative |
| ATE249421T1 (en) | 1997-06-23 | 2003-09-15 | Tanabe Seiyaku Co | INHIBITORS OF ALPHA4-BETA1-MEDIATED CELL ADHESION |
| US6455550B1 (en) * | 1997-08-22 | 2002-09-24 | Hoffmann-La Roche Inc. | N-alkanoylphenylalanine derivatives |
| MY153569A (en) | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| ATE273273T1 (en) | 1998-02-26 | 2004-08-15 | Celltech Therapeutics Ltd | PHENYLALANINE DERIVATIVES AS INHIBITORS OF ALPHA4 INTEGRINS |
| US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
| GB9811159D0 (en) | 1998-05-22 | 1998-07-22 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9811969D0 (en) * | 1998-06-03 | 1998-07-29 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9812088D0 (en) * | 1998-06-05 | 1998-08-05 | Celltech Therapeutics Ltd | Chemical compounds |
| US6685617B1 (en) | 1998-06-23 | 2004-02-03 | Pharmacia & Upjohn Company | Inhibitors of α4β1 mediated cell adhesion |
| GB9814414D0 (en) | 1998-07-03 | 1998-09-02 | Celltech Therapeutics Ltd | Chemical compounds |
| US6339101B1 (en) * | 1998-08-14 | 2002-01-15 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or isosteres for vision and memory disorders |
| US6333340B1 (en) * | 1998-08-14 | 2001-12-25 | Gpi Nil Holdings, Inc. | Small molecule sulfonamides for vision and memory disorders |
| GB9821061D0 (en) | 1998-09-28 | 1998-11-18 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821222D0 (en) | 1998-09-30 | 1998-11-25 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9825652D0 (en) | 1998-11-23 | 1999-01-13 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9826174D0 (en) | 1998-11-30 | 1999-01-20 | Celltech Therapeutics Ltd | Chemical compounds |
| TR200102399T2 (en) * | 1999-02-18 | 2002-01-21 | F. Hoffmann-La Roch Ag | Thioamide derivatives |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| PT1265606E (en) * | 1999-08-13 | 2007-01-31 | Biogen Idec Inc | Cell adhesion inhibitors |
| ATE364592T1 (en) * | 1999-09-24 | 2007-07-15 | Genentech Inc | TYROSINE DERIVATIVES |
| US6534513B1 (en) | 1999-09-29 | 2003-03-18 | Celltech R&D Limited | Phenylalkanoic acid derivatives |
| US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
| JP2003519697A (en) | 1999-12-28 | 2003-06-24 | ファイザー・プロダクツ・インク | Non-peptide VLA-4-dependent cell binding inhibitors useful for the treatment of inflammatory diseases, autoimmune diseases and respiratory diseases |
| ES2295150T3 (en) | 2000-04-17 | 2008-04-16 | Ucb Pharma, S.A. | ENAMINE DERIVATIVES AS CELLULAR ADHESION MOLECULES. |
| US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
| US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
| US6960597B2 (en) | 2000-06-30 | 2005-11-01 | Orth-Mcneil Pharmaceutical, Inc. | Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists |
| EP1301488A1 (en) | 2000-07-07 | 2003-04-16 | Celltech R&D Limited | Squaric acid derivatives containing a bicyclic heteroaromatic ring as integrin antagonists |
| WO2002008206A1 (en) | 2000-07-21 | 2002-01-31 | Elan Pharmaceuticals, Inc. | 3-amino-2-(4-aminocarbonyloxy)phenyl-propionic acid derivatives as alpha-4- integrin inhibitors |
| AU2001275724A1 (en) | 2000-08-02 | 2002-02-13 | Celltech R&D Limited | 3-substituted isoquinolin-1-yl derivatives |
| MY129000A (en) | 2000-08-31 | 2007-03-30 | Tanabe Seiyaku Co | INHIBITORS OF a4 MEDIATED CELL ADHESION |
| JP2004526733A (en) * | 2001-03-20 | 2004-09-02 | メルク エンド カムパニー インコーポレーテッド | Substituted N-arylsulfonyl-proline derivatives as potent cell adhesion inhibitors |
| MY140707A (en) | 2002-02-28 | 2010-01-15 | Mitsubishi Tanabe Pharma Corp | Process for preparing a phenylalanine derivative and intermediates thereof |
| CA2561164A1 (en) * | 2004-04-01 | 2005-10-20 | Elan Pharmaceuticals, Inc. | Steroid sparing agents and their use |
| EP2510941A3 (en) | 2007-02-20 | 2013-01-23 | Merrimack Pharmaceuticals, Inc. | Methods of treating multiple sclerosis by administration of alpha-fetoprotein in combination with an integrin antagonist |
| PL2288715T3 (en) | 2008-04-11 | 2015-03-31 | Merrimack Pharmaceuticals Inc | Human serum albumin linkers and conjugates thereof |
| EP2774919A1 (en) * | 2013-03-06 | 2014-09-10 | Pharmeste S.R.L. In Liquidazione | Novel sulfonamide TRPA1 receptor antagonists |
| WO2014142255A1 (en) | 2013-03-14 | 2014-09-18 | 武田薬品工業株式会社 | Heterocyclic compound |
| EP3018123B1 (en) | 2013-07-03 | 2023-05-10 | Takeda Pharmaceutical Company Limited | Amide compound |
| EP3018126A4 (en) * | 2013-07-03 | 2016-12-07 | Takeda Pharmaceuticals Co | HETEROCYCLIC COMPOUND |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995015973A1 (en) * | 1993-12-06 | 1995-06-15 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
| US6306840B1 (en) * | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
-
1998
- 1998-07-30 AU AU86612/98A patent/AU8661298A/en not_active Abandoned
- 1998-07-30 KR KR1020007000992A patent/KR20010022412A/en not_active Withdrawn
- 1998-07-30 PL PL98338554A patent/PL338554A1/en unknown
- 1998-07-30 CA CA002291475A patent/CA2291475A1/en not_active Abandoned
- 1998-07-30 ZA ZA9806834A patent/ZA986834B/en unknown
- 1998-07-30 HU HU0002682A patent/HUP0002682A3/en unknown
- 1998-07-30 WO PCT/US1998/015314 patent/WO1999006435A1/en not_active Ceased
- 1998-07-30 AR ARP980103776A patent/AR016387A1/en unknown
- 1998-07-30 EP EP98937991A patent/EP0994895A1/en not_active Withdrawn
- 1998-07-30 CN CN98807762A patent/CN1265673A/en active Pending
- 1998-07-30 IL IL13364298A patent/IL133642A0/en unknown
- 1998-07-30 BR BR9811599-5A patent/BR9811599A/en not_active Application Discontinuation
- 1998-07-30 JP JP2000505190A patent/JP2001512137A/en not_active Withdrawn
-
2000
- 2000-01-27 NO NO20000412A patent/NO20000412L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA986834B (en) | 2000-05-02 |
| IL133642A0 (en) | 2001-04-30 |
| NO20000412L (en) | 2000-03-24 |
| CN1265673A (en) | 2000-09-06 |
| AU8661298A (en) | 1999-02-22 |
| HUP0002682A1 (en) | 2001-07-30 |
| NO20000412D0 (en) | 2000-01-27 |
| JP2001512137A (en) | 2001-08-21 |
| BR9811599A (en) | 2000-09-19 |
| HUP0002682A3 (en) | 2001-12-28 |
| KR20010022412A (en) | 2001-03-15 |
| PL338554A1 (en) | 2000-11-06 |
| WO1999006435A1 (en) | 1999-02-11 |
| EP0994895A1 (en) | 2000-04-26 |
| CA2291475A1 (en) | 1999-02-11 |
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