CA2407345C - 4-benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidine-3,4-diol - Google Patents
4-benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidine-3,4-diol Download PDFInfo
- Publication number
- CA2407345C CA2407345C CA002407345A CA2407345A CA2407345C CA 2407345 C CA2407345 C CA 2407345C CA 002407345 A CA002407345 A CA 002407345A CA 2407345 A CA2407345 A CA 2407345A CA 2407345 C CA2407345 C CA 2407345C
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- Canada
- Prior art keywords
- piperidine
- benzyl
- mmol
- hydroxy
- ethyl
- 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.)
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
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- 239000008120 corn starch Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
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- 239000013604 expression vector Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 108091008634 hepatocyte nuclear factors 4 Proteins 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 210000003657 middle cerebral artery Anatomy 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LLYKPZOWCPVRPD-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine;n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=CC=N1 LLYKPZOWCPVRPD-UHFFFAOYSA-N 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 239000004090 neuroprotective agent Substances 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000012402 patch clamp technique Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229950007002 phosphocreatine Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001536 pro-arrhythmogenic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
- C07D211/50—Aroyl radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00108769 | 2000-04-25 | ||
| EP00108769.1 | 2000-04-25 | ||
| PCT/EP2001/004305 WO2001081309A2 (en) | 2000-04-25 | 2001-04-17 | 4-benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidine-3,4-diol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2407345A1 CA2407345A1 (en) | 2001-11-01 |
| CA2407345C true CA2407345C (en) | 2009-04-07 |
Family
ID=8168543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002407345A Expired - Fee Related CA2407345C (en) | 2000-04-25 | 2001-04-17 | 4-benzyl-1-[2-(4-hydroxy-phenoxy)-ethyl]-piperidine-3,4-diol |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6432985B2 (OSRAM) |
| EP (1) | EP1278730B1 (OSRAM) |
| JP (1) | JP3831255B2 (OSRAM) |
| KR (1) | KR100527527B1 (OSRAM) |
| CN (1) | CN1178914C (OSRAM) |
| AR (1) | AR028357A1 (OSRAM) |
| AT (1) | ATE313527T1 (OSRAM) |
| AU (1) | AU785153B2 (OSRAM) |
| BR (1) | BR0110233A (OSRAM) |
| CA (1) | CA2407345C (OSRAM) |
| DE (1) | DE60116080T2 (OSRAM) |
| DK (1) | DK1278730T3 (OSRAM) |
| ES (1) | ES2254422T3 (OSRAM) |
| MX (1) | MXPA02010573A (OSRAM) |
| PE (1) | PE20011229A1 (OSRAM) |
| UY (1) | UY26681A1 (OSRAM) |
| WO (1) | WO2001081309A2 (OSRAM) |
| ZA (1) | ZA200208134B (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7640062B2 (en) | 2000-05-08 | 2009-12-29 | Brainsgate Ltd. | Methods and systems for management of alzheimer's disease |
| US7684859B2 (en) | 2002-04-25 | 2010-03-23 | Brainsgate Ltd. | Stimulation of the OTIC ganglion for treating medical conditions |
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| JP2006515999A (ja) | 2002-11-14 | 2006-06-15 | ブレインズゲート リミティド | 刺激のための外科用ツール及び技法 |
| US9233245B2 (en) | 2004-02-20 | 2016-01-12 | Brainsgate Ltd. | SPG stimulation |
| US8010189B2 (en) * | 2004-02-20 | 2011-08-30 | Brainsgate Ltd. | SPG stimulation for treating complications of subarachnoid hemorrhage |
| US8055347B2 (en) | 2005-08-19 | 2011-11-08 | Brainsgate Ltd. | Stimulation for treating brain events and other conditions |
| EP1976495A2 (en) * | 2006-01-06 | 2008-10-08 | Aarhus Universitet | Compounds acting on the serotonin transporter |
| CA2688784A1 (en) * | 2007-05-21 | 2008-11-27 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using quinolinone based atypical antipsychotic agents |
| US8008253B2 (en) * | 2007-07-03 | 2011-08-30 | Andrew Tasker | Treatment for anxiety |
| US7860569B2 (en) | 2007-10-18 | 2010-12-28 | Brainsgate, Ltd. | Long-term SPG stimulation therapy for prevention of vascular dementia |
| BRPI0909378A2 (pt) * | 2008-03-27 | 2015-10-06 | Evotec Neurosciences Gmbh | métodos para tratar distúrbios usando antagonista seletivo de nmda subtipo nr2b |
| US8846315B2 (en) | 2008-08-12 | 2014-09-30 | Zinfandel Pharmaceuticals, Inc. | Disease risk factors and methods of use |
| PE20150362A1 (es) * | 2008-08-12 | 2015-03-20 | Zinfandel Pharmaceuticals Inc | Metodo de identificacion de factores de riesgo de la enfermedad |
| CA2824050A1 (en) | 2011-01-10 | 2012-07-19 | Zinfandel Pharmaceuticals, Inc. | Methods and drug products for treating alzheimer's disease |
| US8703763B2 (en) * | 2011-03-02 | 2014-04-22 | Hoffmann-La Roche Inc. | Bridged piperidine derivatives |
| US9675796B2 (en) | 2013-11-10 | 2017-06-13 | Brainsgate Ltd. | Implant and delivery system for neural stimulator |
| EP3233799B1 (en) | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| EP3233077A4 (en) | 2014-12-19 | 2018-08-08 | The Broad Institute Inc. | Dopamine d2 receptor ligands |
| EP3093043B1 (en) | 2015-05-13 | 2018-11-14 | Brainsgate Ltd. | Implant and delivery system for neural stimulator |
| AR110122A1 (es) * | 2016-11-08 | 2019-02-27 | Hoffmann La Roche | Fenoxitriazoles |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA9610745B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| ZA9610738B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | Subtype selective nmda receptor ligands and the use thereof |
| TW498067B (en) | 1996-07-19 | 2002-08-11 | Hoffmann La Roche | 4-hydroxy-piperidine derivatives |
-
2001
- 2001-03-19 US US09/811,888 patent/US6432985B2/en not_active Expired - Fee Related
- 2001-04-17 AT AT01933833T patent/ATE313527T1/de not_active IP Right Cessation
- 2001-04-17 BR BR0110233-8A patent/BR0110233A/pt not_active Application Discontinuation
- 2001-04-17 DK DK01933833T patent/DK1278730T3/da active
- 2001-04-17 WO PCT/EP2001/004305 patent/WO2001081309A2/en not_active Ceased
- 2001-04-17 CN CNB018085911A patent/CN1178914C/zh not_active Expired - Fee Related
- 2001-04-17 AU AU60213/01A patent/AU785153B2/en not_active Ceased
- 2001-04-17 ES ES01933833T patent/ES2254422T3/es not_active Expired - Lifetime
- 2001-04-17 KR KR10-2002-7014261A patent/KR100527527B1/ko not_active Expired - Fee Related
- 2001-04-17 DE DE60116080T patent/DE60116080T2/de not_active Expired - Lifetime
- 2001-04-17 MX MXPA02010573A patent/MXPA02010573A/es active IP Right Grant
- 2001-04-17 EP EP01933833A patent/EP1278730B1/en not_active Expired - Lifetime
- 2001-04-17 CA CA002407345A patent/CA2407345C/en not_active Expired - Fee Related
- 2001-04-17 JP JP2001578404A patent/JP3831255B2/ja not_active Expired - Fee Related
- 2001-04-19 PE PE2001000359A patent/PE20011229A1/es not_active Application Discontinuation
- 2001-04-23 AR ARP010101869A patent/AR028357A1/es active IP Right Grant
- 2001-04-24 UY UY26681A patent/UY26681A1/es not_active Application Discontinuation
-
2002
- 2002-10-09 ZA ZA200208134A patent/ZA200208134B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE313527T1 (de) | 2006-01-15 |
| MXPA02010573A (es) | 2003-03-10 |
| EP1278730A2 (en) | 2003-01-29 |
| PE20011229A1 (es) | 2001-12-08 |
| DK1278730T3 (da) | 2006-05-01 |
| AU6021301A (en) | 2001-11-07 |
| US6432985B2 (en) | 2002-08-13 |
| DE60116080D1 (de) | 2006-01-26 |
| WO2001081309A3 (en) | 2002-01-17 |
| EP1278730B1 (en) | 2005-12-21 |
| KR20040007216A (ko) | 2004-01-24 |
| ES2254422T3 (es) | 2006-06-16 |
| JP3831255B2 (ja) | 2006-10-11 |
| CN1443166A (zh) | 2003-09-17 |
| BR0110233A (pt) | 2003-01-21 |
| ZA200208134B (en) | 2004-01-22 |
| KR100527527B1 (ko) | 2005-11-09 |
| US20010047014A1 (en) | 2001-11-29 |
| AR028357A1 (es) | 2003-05-07 |
| UY26681A1 (es) | 2001-10-25 |
| WO2001081309A2 (en) | 2001-11-01 |
| DE60116080T2 (de) | 2006-08-24 |
| CA2407345A1 (en) | 2001-11-01 |
| AU785153B2 (en) | 2006-10-05 |
| CN1178914C (zh) | 2004-12-08 |
| JP2004509837A (ja) | 2004-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |