UA74531C2 - Antagonsists for treating disorders mediated by cd11/cd18 adhesion receptors - Google Patents
Antagonsists for treating disorders mediated by cd11/cd18 adhesion receptors Download PDFInfo
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- UA74531C2 UA74531C2 UA2000106027A UA2000106027A UA74531C2 UA 74531 C2 UA74531 C2 UA 74531C2 UA 2000106027 A UA2000106027 A UA 2000106027A UA 2000106027 A UA2000106027 A UA 2000106027A UA 74531 C2 UA74531 C2 UA 74531C2
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- 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
- A61K31/4192—1,2,3-Triazoles
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- 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
- A61K31/433—Thidiazoles
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7973298P | 1998-03-27 | 1998-03-27 | |
| PCT/US1999/006410 WO1999049856A2 (fr) | 1998-03-27 | 1999-03-24 | Antagonistes destines au traitement de troubles induits par le recepteur d'adhesion de cd11/cd18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA74531C2 true UA74531C2 (en) | 2006-01-16 |
Family
ID=22152446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2000106027A UA74531C2 (en) | 1998-03-27 | 1999-03-24 | Antagonsists for treating disorders mediated by cd11/cd18 adhesion receptors |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20050203135A1 (fr) |
| EP (1) | EP1063982B1 (fr) |
| JP (2) | JP2002509881A (fr) |
| KR (1) | KR100596109B1 (fr) |
| CN (1) | CN1191063C (fr) |
| AT (1) | ATE353640T1 (fr) |
| AU (1) | AU764524B2 (fr) |
| BR (1) | BR9909418A (fr) |
| CA (1) | CA2325986A1 (fr) |
| DE (1) | DE69935133T2 (fr) |
| EA (1) | EA007852B1 (fr) |
| HU (1) | HUP0101587A3 (fr) |
| IL (2) | IL138297A0 (fr) |
| NO (1) | NO20004800L (fr) |
| NZ (1) | NZ506779A (fr) |
| PL (1) | PL343555A1 (fr) |
| UA (1) | UA74531C2 (fr) |
| WO (1) | WO1999049856A2 (fr) |
| ZA (1) | ZA200004653B (fr) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6331640B1 (en) | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
| US6867203B2 (en) | 1998-12-29 | 2005-03-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds |
| US6878700B1 (en) | 1998-12-29 | 2005-04-12 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds |
| US6110922A (en) | 1998-12-29 | 2000-08-29 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds |
| JP3833532B2 (ja) | 1999-07-21 | 2006-10-11 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 炎症性疾患の治療において有用な小分子 |
| WO2001007044A1 (fr) | 1999-07-21 | 2001-02-01 | Boehringer Ingelheim Pharmaceuticals, Inc. | Petites molecules utiles pour le traitement de maladies inflammatoires |
| US6492408B1 (en) | 1999-07-21 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Small molecules useful in the treatment of inflammatory disease |
| WO2001007052A1 (fr) | 1999-07-21 | 2001-02-01 | Boehringer Ingelheim Pharmaceuticals, Inc. | Petites molecules des plus utiles dans le traitement de maladies inflammatoires |
| CZ2002518A3 (cs) * | 1999-08-13 | 2002-05-15 | Biogen, Inc. | Inhibitory buněčné adheze a farmaceutické prostředky, které je obsahují |
| US6515124B2 (en) | 2000-02-09 | 2003-02-04 | Hoffman-La Roche Inc. | Dehydroamino acids |
| PL205134B1 (pl) * | 2000-03-27 | 2010-03-31 | Scripps Research Inst | Pochodne glicylolizyny, preparat farmaceutyczny i zastosowanie pochodnych glicylolizyny |
| EP1294704A1 (fr) | 2000-06-29 | 2003-03-26 | Abbott Laboratories | Derives d'aryle phenylheterocyclyle sulfures et leur utilisation en tant qu'agents immunosuppresseurs anti-inflammatoires inhibant l'adherence cellulaire |
| US6521619B2 (en) | 2000-06-29 | 2003-02-18 | Icos Corporation | Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents |
| WO2002059114A1 (fr) | 2000-11-28 | 2002-08-01 | Genentech, Inc. | Composes antagonistes lfa-1 |
| AU2003265398A1 (en) * | 2002-08-09 | 2004-02-25 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
| WO2004032861A2 (fr) | 2002-10-11 | 2004-04-22 | Bristol-Myers Squibb Company | Composes hexahydro-benzimidazolones utiles en tant qu'agents anti-inflammatoires |
| US20050026844A1 (en) | 2003-04-03 | 2005-02-03 | Regents Of The University Of California | Inhibitors for the soluble epoxide hydrolase |
| WO2005089380A2 (fr) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reduction de la nephropathie au moyen d'inhibiteurs d'hydrolase d'epoxyde soluble et d'epoxyeicosanoides |
| US7501538B2 (en) * | 2003-08-08 | 2009-03-10 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| US7208601B2 (en) * | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| US7920906B2 (en) | 2005-03-10 | 2011-04-05 | Dexcom, Inc. | System and methods for processing analyte sensor data for sensor calibration |
| US7199125B2 (en) | 2003-10-02 | 2007-04-03 | Bristol-Myers Squibb Company | Spiro-cyclic compounds useful as anti-inflammatory agents |
| CA2544678C (fr) | 2003-11-05 | 2013-12-31 | Sunesis Pharmaceuticals, Inc. | Modulateurs de l'adhesion cellulaire |
| US9247900B2 (en) | 2004-07-13 | 2016-02-02 | Dexcom, Inc. | Analyte sensor |
| US8989833B2 (en) | 2004-07-13 | 2015-03-24 | Dexcom, Inc. | Transcutaneous analyte sensor |
| US20070045902A1 (en) | 2004-07-13 | 2007-03-01 | Brauker James H | Analyte sensor |
| US7375237B2 (en) | 2004-08-18 | 2008-05-20 | Bristol-Myers Squibb Company | Pyrrolizine compounds useful as anti-inflammatory agents |
| TW200616634A (en) | 2004-10-01 | 2006-06-01 | Bristol Myers Squibb Co | Crystalline forms and process for preparing spiro-hydantoin compounds |
| JP2008517072A (ja) * | 2004-10-20 | 2008-05-22 | ザ レジェンツ オブ ザ ユニバーシティー オブ カリフォルニア | 可溶性エポキシド加水分解酵素の改良された阻害剤 |
| US7186727B2 (en) | 2004-12-14 | 2007-03-06 | Bristol-Myers Squibb Company | Pyridyl-substituted spiro-hydantoin compounds and use thereof |
| DK2444079T3 (en) | 2005-05-17 | 2017-01-30 | Sarcode Bioscience Inc | Compositions and Methods for the Treatment of Eye Diseases |
| WO2007127272A2 (fr) * | 2006-04-24 | 2007-11-08 | The Cbr Institute For Biomedical Research | Méthode de production d'immunoliposomes et compositions les incluant |
| EP2018436A2 (fr) * | 2006-04-25 | 2009-01-28 | Immune Disease Institute Inc. | Administration ciblée vers des leucocytes au moyen de supports non protéiniques |
| ES2830024T3 (es) | 2007-10-19 | 2021-06-02 | Novartis Ag | Composiciones y métodos para el tratamiento del edema macular |
| MX2010004995A (es) | 2007-11-29 | 2010-05-20 | Boehringer Ingelheim Int | Derivados de amidas del acido 6,7-dihidro-5h-imidazo[1,2-a]imidazo l-3-carboxilico. |
| WO2009139817A2 (fr) | 2008-04-15 | 2009-11-19 | Sarcode Corporation | Produit pharmaceutique cristallin et ses procédés de préparation et d'utilisation |
| WO2009128932A1 (fr) * | 2008-04-15 | 2009-10-22 | Sarcode Corporation | Administration d'antagonistes de lfa-1 au système gastro-intestinal |
| WO2009128934A1 (fr) | 2008-04-15 | 2009-10-22 | Sarcode Corporation | Antagonistes de lfa-1 topiques utilisés dans le traitement localisé de troubles de nature immunitaire |
| PT2303270T (pt) | 2008-05-05 | 2017-08-25 | Sanofi Sa | Derivados fundidos do ácido ciclopentanocarboxílico substituídos por acilamino e sua utilização como produtos farmacêuticos |
| US8835498B2 (en) | 2008-11-19 | 2014-09-16 | Pola Chemical Industries Inc. | Anti-wrinkle agents |
| WO2010141330A1 (fr) | 2009-06-02 | 2010-12-09 | Boehringer Ingelheim International Gmbh | Dérivés d'amides d'acide 6,7-dihydro-5h-imidazo [1,2-a] imidazole-3-carboxylique |
| BRPI1012581A2 (pt) | 2009-06-02 | 2016-03-29 | Boehringer Ingelheim Int | derivados de amidas de ácido 6, 7-di-hidro-5h-imidazol[1,2-a]imidazol-3-carboxílico |
| WO2011050175A1 (fr) | 2009-10-21 | 2011-04-28 | Sarcode Corporation | Agent pharmaceutique cristallin et procédés de préparation et utilisation de celui-ci |
| AR079022A1 (es) | 2009-11-02 | 2011-12-21 | Sanofi Aventis | Derivados de acido carboxilico ciclico sustituidos con acilamino, su uso como productos farmaceuticos, composicion farmaceutica y metodo de preparacion |
| US8404859B2 (en) | 2011-03-16 | 2013-03-26 | Hoffmann-La Roche Inc. | Thiazole and thiophene compounds |
| CN103420917B (zh) * | 2012-05-18 | 2015-08-19 | 国药一心制药有限公司 | 含稠环结构的苯甲酰胺类化合物及其作为抗肿瘤药物应用 |
| KR20200108932A (ko) | 2012-07-25 | 2020-09-21 | 에스에이알코드 바이오사이언스 인코포레이티드 | Lfa-1 저해제 및 그의 다형체 |
| FR3019901B1 (fr) * | 2014-04-09 | 2020-10-30 | Bio Rad Innovations | Marqueur de controle pour la mise en oeuvre de procedes d'analyse sur spots |
| WO2017102014A1 (fr) * | 2015-12-17 | 2017-06-22 | Universite D'aix-Marseille | Dérivés de thiophène propénamide utilisés comme inhibiteurs de flavivirus et leur utilisation |
| CN107987105B (zh) * | 2017-11-24 | 2019-10-01 | 无锡微色谱生物科技有限公司 | 一种可用于皮肤敷料的h2s给体化合物、海绵敷料和制备方法 |
| WO2021119199A1 (fr) * | 2019-12-10 | 2021-06-17 | The Regents Of The University Of California | Inhibiteurs d'alpha-5 bêta-1 |
| CA3181786A1 (fr) * | 2020-05-01 | 2021-11-04 | The Regents Of The University Of California | Inhibiteurs de l'integrine alpha 2 beta 1 et leurs procedes d'utilisation |
| WO2023204330A1 (fr) * | 2022-04-22 | 2023-10-26 | 트윈피그바이오랩(주) | Système d'administration de médicament à médiation par itgb2 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1182518A (en) * | 1968-11-01 | 1970-02-25 | Parke Davis & Co | Novel Dibasic Acid Compounds and Means for the Production Thereof |
| US4314988A (en) * | 1979-10-31 | 1982-02-09 | Baker Instruments Corp. | Folic acid derivatives and process for preparation |
| US4871743A (en) * | 1988-01-19 | 1989-10-03 | The Trustees Of Princeton University | L-glutamic acid derivatives |
| US5013738A (en) * | 1990-04-18 | 1991-05-07 | The Trustees Of Princeton University | L-glutamic acid derivatives |
| DE69216509T2 (de) * | 1991-08-12 | 1997-05-28 | Takeda Chemical Industries Ltd | Kondensierte Pyrimidinderivate, ihre Herstellung und ihre Verwendung als Antitumormittel |
| JPH05306226A (ja) * | 1992-04-27 | 1993-11-19 | Takeda Chem Ind Ltd | 慢性免疫疾患治療剤 |
| PT674516E (pt) * | 1992-12-16 | 2000-05-31 | Agouron Pharma | Compostos de 5-tiapirimidinona e 5-selenopirimidinona substituidos antiproliferativos |
| EP0849256B1 (fr) * | 1995-08-22 | 2005-06-08 | Japan Tobacco Inc. | Composes amide et leur utilisation |
| EP1005445B1 (fr) * | 1997-08-22 | 2004-05-26 | F. Hoffmann-La Roche Ag | Derives de n-alcanoylphenilalanine |
| AU1411499A (en) * | 1997-11-20 | 1999-06-15 | Merck & Co., Inc. | Para-aminomethylaryl carboxamide derivatives |
| MY153569A (en) * | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
-
1999
- 1999-03-24 JP JP2000540822A patent/JP2002509881A/ja not_active Withdrawn
- 1999-03-24 EA EA200000985A patent/EA007852B1/ru not_active IP Right Cessation
- 1999-03-24 WO PCT/US1999/006410 patent/WO1999049856A2/fr not_active Ceased
- 1999-03-24 HU HU0101587A patent/HUP0101587A3/hu unknown
- 1999-03-24 PL PL99343555A patent/PL343555A1/xx not_active Application Discontinuation
- 1999-03-24 DE DE69935133T patent/DE69935133T2/de not_active Expired - Fee Related
- 1999-03-24 BR BR9909418-5A patent/BR9909418A/pt not_active Application Discontinuation
- 1999-03-24 IL IL13829799A patent/IL138297A0/xx not_active IP Right Cessation
- 1999-03-24 CN CNB998043753A patent/CN1191063C/zh not_active Expired - Fee Related
- 1999-03-24 EP EP99912869A patent/EP1063982B1/fr not_active Expired - Lifetime
- 1999-03-24 AT AT99912869T patent/ATE353640T1/de not_active IP Right Cessation
- 1999-03-24 UA UA2000106027A patent/UA74531C2/uk unknown
- 1999-03-24 NZ NZ506779A patent/NZ506779A/en unknown
- 1999-03-24 AU AU31137/99A patent/AU764524B2/en not_active Ceased
- 1999-03-24 KR KR1020007010720A patent/KR100596109B1/ko not_active Expired - Fee Related
- 1999-03-24 CA CA002325986A patent/CA2325986A1/fr not_active Abandoned
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2000
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- 2000-09-06 IL IL138297A patent/IL138297A/en unknown
- 2000-09-26 NO NO20004800A patent/NO20004800L/no not_active Application Discontinuation
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2003
- 2003-08-26 US US10/649,762 patent/US20050203135A1/en not_active Abandoned
-
2007
- 2007-04-09 JP JP2007101875A patent/JP2007224037A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN1191063C (zh) | 2005-03-02 |
| JP2007224037A (ja) | 2007-09-06 |
| IL138297A0 (en) | 2001-10-31 |
| WO1999049856A2 (fr) | 1999-10-07 |
| NO20004800D0 (no) | 2000-09-26 |
| KR20010034708A (ko) | 2001-04-25 |
| EP1063982B1 (fr) | 2007-02-14 |
| WO1999049856A3 (fr) | 1999-11-18 |
| ATE353640T1 (de) | 2007-03-15 |
| JP2002509881A (ja) | 2002-04-02 |
| EA007852B1 (ru) | 2007-02-27 |
| DE69935133D1 (de) | 2007-03-29 |
| IL138297A (en) | 2006-06-11 |
| EA200000985A1 (ru) | 2001-06-25 |
| PL343555A1 (en) | 2001-08-27 |
| US20050203135A1 (en) | 2005-09-15 |
| BR9909418A (pt) | 2001-09-25 |
| AU764524B2 (en) | 2003-08-21 |
| NO20004800L (no) | 2000-11-24 |
| KR100596109B1 (ko) | 2006-07-05 |
| HUP0101587A2 (hu) | 2001-08-28 |
| HUP0101587A3 (en) | 2003-03-28 |
| NZ506779A (en) | 2003-08-29 |
| EP1063982A2 (fr) | 2001-01-03 |
| DE69935133T2 (de) | 2007-11-22 |
| CN1295471A (zh) | 2001-05-16 |
| CA2325986A1 (fr) | 1999-10-07 |
| ZA200004653B (en) | 2002-02-27 |
| AU3113799A (en) | 1999-10-18 |
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