CA2402751C - Decahydro-isoquinolines - Google Patents
Decahydro-isoquinolines Download PDFInfo
- Publication number
- CA2402751C CA2402751C CA002402751A CA2402751A CA2402751C CA 2402751 C CA2402751 C CA 2402751C CA 002402751 A CA002402751 A CA 002402751A CA 2402751 A CA2402751 A CA 2402751A CA 2402751 C CA2402751 C CA 2402751C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- difluoro
- compound
- benzo
- formula
- 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 - Fee Related
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- 230000002631 hypothermal effect Effects 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011503 in vivo imaging Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229960001078 lithium Drugs 0.000 description 1
- 210000004072 lung Anatomy 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
- 206010027175 memory impairment Diseases 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- NOUIRZGGWSLLAJ-MFKMUULPSA-N n-[(1r,2r)-1-hydroxy-1-phenylpropan-2-yl]-n-methylpropanamide Chemical compound CCC(=O)N(C)[C@H](C)[C@H](O)C1=CC=CC=C1 NOUIRZGGWSLLAJ-MFKMUULPSA-N 0.000 description 1
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- 239000003176 neuroleptic agent Substances 0.000 description 1
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- 238000011580 nude mouse model Methods 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- 230000035755 proliferation Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 230000004037 social stress Effects 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P25/18—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0007108.4A GB0007108D0 (en) | 2000-03-23 | 2000-03-23 | Organic compounds |
| GB0007108.4 | 2000-03-23 | ||
| PCT/EP2001/003211 WO2001070731A1 (en) | 2000-03-23 | 2001-03-21 | Decahydro-isoquinolines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2402751A1 CA2402751A1 (en) | 2001-09-27 |
| CA2402751C true CA2402751C (en) | 2010-01-19 |
Family
ID=9888307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002402751A Expired - Fee Related CA2402751C (en) | 2000-03-23 | 2001-03-21 | Decahydro-isoquinolines |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6635647B2 (enExample) |
| EP (1) | EP1268466B1 (enExample) |
| JP (1) | JP4118565B2 (enExample) |
| AR (1) | AR029821A1 (enExample) |
| AT (1) | ATE298332T1 (enExample) |
| AU (1) | AU2001239310A1 (enExample) |
| CA (1) | CA2402751C (enExample) |
| CO (1) | CO5271675A1 (enExample) |
| DE (1) | DE60111621T2 (enExample) |
| DK (1) | DK1268466T3 (enExample) |
| ES (1) | ES2243462T3 (enExample) |
| GB (1) | GB0007108D0 (enExample) |
| PE (1) | PE20011114A1 (enExample) |
| PT (1) | PT1268466E (enExample) |
| WO (1) | WO2001070731A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0128996D0 (en) | 2001-12-04 | 2002-01-23 | Novartis Ag | Organic compounds |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| BRPI0706778A2 (pt) * | 2006-01-30 | 2011-04-05 | Speedel Experimenta Ag | processos para a preparação estéreo-seletiva de álcoois a partir de compostos alfa, beta-insaturados |
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| KR20100065191A (ko) | 2007-09-14 | 2010-06-15 | 오르토-맥닐-얀센 파마슈티칼스 인코포레이티드 | １,３-이치환된 ４-(아릴-ｘ-페닐)-１ｈ-피리딘-２-온 |
| CA2696948C (en) | 2007-09-14 | 2013-04-30 | Jose Maria Cid-Nunez | 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h,1'h-[1,4']bipyridinyl-2'-ones |
| CA2735764C (en) | 2008-09-02 | 2016-06-14 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| BRPI0921333A2 (pt) | 2008-11-28 | 2015-12-29 | Addex Pharmaceuticals Sa | derivados de indol e benzoxazina como moduladores de receptores de glutamato metabotrópicos |
| NZ596078A (en) | 2009-05-12 | 2013-06-28 | Janssen Pharmaceuticals Inc | 1,2,4-TRIAZOLO [4,3-a] PYRIDINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OR PREVENTION OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS |
| EA020671B1 (ru) | 2009-05-12 | 2014-12-30 | Янссен Фармасьютикалз, Инк. | ПРОИЗВОДНЫЕ 1,2,4-ТРИАЗОЛО[4,3-a]ПИРИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПОЛОЖИТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR2 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| WO2011082271A2 (en) | 2009-12-30 | 2011-07-07 | Arqule, Inc. | Substituted triazolo-pyrimidine compounds |
| CA2815002C (en) | 2010-11-08 | 2019-10-22 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| CN103298810B (zh) | 2010-11-08 | 2016-03-16 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| EP2643320B1 (en) | 2010-11-08 | 2015-03-04 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| KR102414246B1 (ko) | 2014-01-21 | 2022-06-27 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
| LT3431106T (lt) | 2014-01-21 | 2021-02-10 | Janssen Pharmaceutica Nv | Deriniai, apimantys 2 potipio metabotropinio glutamaterginio receptoriaus teigiamus alosterinius moduliatorius arba ortosterinius agonistus, ir jų panaudojimas |
| EP3661500B1 (en) | 2017-07-31 | 2026-01-07 | Novartis AG | Use of mavoglurant in the reduction of cocaine use or in preventing relapse into cocaine use |
| SG11202002032SA (en) | 2017-09-22 | 2020-04-29 | Jubilant Epipad LLC | Heterocyclic compounds as pad inhibitors |
| CA3076476A1 (en) | 2017-10-18 | 2019-04-25 | Jubilant Epipad LLC | Imidazo-pyridine compounds as pad inhibitors |
| BR112020008851A2 (pt) | 2017-11-06 | 2020-10-20 | Jubilant Prodel LLC | composto da fórmula i, processo de preparação de compostos da fórmula i, composição farmacêutica, método para o tratamento e/ou prevenção de várias doenças, uso, método para o tratamento de câncer, método de tratamento de câncer e método para o tratamento e/ou prevenção de câncer e doenças infecciosas |
| PL3704120T3 (pl) | 2017-11-24 | 2024-09-16 | Jubilant Episcribe Llc | Związki heterocykliczne jako inhibitory prmt5 |
| SG11202008950PA (en) | 2018-03-13 | 2020-10-29 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
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| AU5265599A (en) * | 1998-04-08 | 1999-11-01 | Takeda Chemical Industries Ltd. | Amine compounds, their production and their use as somatostatin receptor antagonists or agonists |
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2000
- 2000-03-23 GB GBGB0007108.4A patent/GB0007108D0/en not_active Ceased
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2001
- 2001-03-21 PE PE2001000262A patent/PE20011114A1/es not_active Application Discontinuation
- 2001-03-21 EP EP01913896A patent/EP1268466B1/en not_active Expired - Lifetime
- 2001-03-21 AU AU2001239310A patent/AU2001239310A1/en not_active Abandoned
- 2001-03-21 PT PT01913896T patent/PT1268466E/pt unknown
- 2001-03-21 WO PCT/EP2001/003211 patent/WO2001070731A1/en not_active Ceased
- 2001-03-21 CO CO01022539A patent/CO5271675A1/es not_active Application Discontinuation
- 2001-03-21 JP JP2001568934A patent/JP4118565B2/ja not_active Expired - Fee Related
- 2001-03-21 DK DK01913896T patent/DK1268466T3/da active
- 2001-03-21 CA CA002402751A patent/CA2402751C/en not_active Expired - Fee Related
- 2001-03-21 US US10/221,983 patent/US6635647B2/en not_active Expired - Fee Related
- 2001-03-21 AR ARP010101320A patent/AR029821A1/es unknown
- 2001-03-21 AT AT01913896T patent/ATE298332T1/de not_active IP Right Cessation
- 2001-03-21 DE DE60111621T patent/DE60111621T2/de not_active Expired - Lifetime
- 2001-03-21 ES ES01913896T patent/ES2243462T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6635647B2 (en) | 2003-10-21 |
| AU2001239310A1 (en) | 2001-10-03 |
| EP1268466A1 (en) | 2003-01-02 |
| GB0007108D0 (en) | 2000-05-17 |
| ES2243462T3 (es) | 2005-12-01 |
| ATE298332T1 (de) | 2005-07-15 |
| CA2402751A1 (en) | 2001-09-27 |
| DK1268466T3 (da) | 2005-10-10 |
| US20030120072A1 (en) | 2003-06-26 |
| CO5271675A1 (es) | 2003-04-30 |
| PT1268466E (pt) | 2005-10-31 |
| JP4118565B2 (ja) | 2008-07-16 |
| PE20011114A1 (es) | 2001-11-30 |
| AR029821A1 (es) | 2003-07-16 |
| DE60111621T2 (de) | 2006-05-18 |
| DE60111621D1 (de) | 2005-07-28 |
| EP1268466B1 (en) | 2005-06-22 |
| WO2001070731A1 (en) | 2001-09-27 |
| JP2003528096A (ja) | 2003-09-24 |
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