CA2468681C - Adenosine a2a receptor antagonists - Google Patents
Adenosine a2a receptor antagonists Download PDFInfo
- Publication number
- CA2468681C CA2468681C CA2468681A CA2468681A CA2468681C CA 2468681 C CA2468681 C CA 2468681C CA 2468681 A CA2468681 A CA 2468681A CA 2468681 A CA2468681 A CA 2468681A CA 2468681 C CA2468681 C CA 2468681C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- group
- mmol
- aryl
- 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
Links
- YYBDTYHGKDQGRA-UHFFFAOYSA-N CC(C)c1cc(-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)ccc1 Chemical compound CC(C)c1cc(-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)ccc1 YYBDTYHGKDQGRA-UHFFFAOYSA-N 0.000 description 1
- KPIAVEQLXHXMGH-UHFFFAOYSA-N CN(CCc1ccccc1)Cc1ccccc1-c1cc2nc(-c3ccc[o]3)n[n]2c(N)n1 Chemical compound CN(CCc1ccccc1)Cc1ccccc1-c1cc2nc(-c3ccc[o]3)n[n]2c(N)n1 KPIAVEQLXHXMGH-UHFFFAOYSA-N 0.000 description 1
- FCTPEAYMTQIFGW-UHFFFAOYSA-O CN1CCN(Cc(cccc2)c2-c2cc3nc(-c4ccc[o]4)n[n]3c(N)[nH+]2)CC1 Chemical compound CN1CCN(Cc(cccc2)c2-c2cc3nc(-c4ccc[o]4)n[n]3c(N)[nH+]2)CC1 FCTPEAYMTQIFGW-UHFFFAOYSA-O 0.000 description 1
- DTXXZCBVLCRBBI-UHFFFAOYSA-N COCCOc(cc1)ccc1N1CCN(Cc2ccccc2-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)CC1 Chemical compound COCCOc(cc1)ccc1N1CCN(Cc2ccccc2-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)CC1 DTXXZCBVLCRBBI-UHFFFAOYSA-N 0.000 description 1
- OLGJHFLZQUTNEK-UHFFFAOYSA-N COc(cc1)ccc1N1CCN(Cc(cccc2)c2-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)CC1 Chemical compound COc(cc1)ccc1N1CCN(Cc(cccc2)c2-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)CC1 OLGJHFLZQUTNEK-UHFFFAOYSA-N 0.000 description 1
- JFULOOVEGJLBED-UHFFFAOYSA-N Cc1c[s]c(-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)c1 Chemical compound Cc1c[s]c(-c2cc3nc(-c4ccc[o]4)n[n]3c(N)n2)c1 JFULOOVEGJLBED-UHFFFAOYSA-N 0.000 description 1
- GZXCNDQELURUEB-UHFFFAOYSA-N Nc1nc(-c([s]2)ccc2Cl)cc2nc(-c3ccc[o]3)n[n]12 Chemical compound Nc1nc(-c([s]2)ccc2Cl)cc2nc(-c3ccc[o]3)n[n]12 GZXCNDQELURUEB-UHFFFAOYSA-N 0.000 description 1
- PIAQAKHGQBJDIW-UHFFFAOYSA-N Nc1nc(-c2c(CN(CC3)CCN3c(ccc(F)c3)c3F)cccc2)cc2nc(-c3ccc[o]3)n[n]12 Chemical compound Nc1nc(-c2c(CN(CC3)CCN3c(ccc(F)c3)c3F)cccc2)cc2nc(-c3ccc[o]3)n[n]12 PIAQAKHGQBJDIW-UHFFFAOYSA-N 0.000 description 1
- HWMOGULJRPVFOS-UHFFFAOYSA-N Nc1nc(-c2c(CN3CCOCC3)cccc2)cc2nc(-c3ccc[o]3)n[n]12 Chemical compound Nc1nc(-c2c(CN3CCOCC3)cccc2)cc2nc(-c3ccc[o]3)n[n]12 HWMOGULJRPVFOS-UHFFFAOYSA-N 0.000 description 1
- HLZWWIGPJVCGMI-UHFFFAOYSA-N Nc1nc(-c2ccc(CO)cc2)cc2nc(-c3ccc[o]3)n[n]12 Chemical compound Nc1nc(-c2ccc(CO)cc2)cc2nc(-c3ccc[o]3)n[n]12 HLZWWIGPJVCGMI-UHFFFAOYSA-N 0.000 description 1
- HHAIUQZUHVUHSD-UHFFFAOYSA-N Nc1nc(-c2ccccc2CN2CCCCC2)cc2nc(-c3ccc[o]3)n[n]12 Chemical compound Nc1nc(-c2ccccc2CN2CCCCC2)cc2nc(-c3ccc[o]3)n[n]12 HHAIUQZUHVUHSD-UHFFFAOYSA-N 0.000 description 1
- NHZYHGYDBWKPRJ-UHFFFAOYSA-N Nc1nc(-c2ccncc2)cc2nc(-c3ccc[o]3)n[n]12 Chemical compound Nc1nc(-c2ccncc2)cc2nc(-c3ccc[o]3)n[n]12 NHZYHGYDBWKPRJ-UHFFFAOYSA-N 0.000 description 1
- ZBJBBCUUKWBBGA-UHFFFAOYSA-N Nc1nc(-c2cnccc2)cc2nc(-c3ccc[o]3)n[n]12 Chemical compound Nc1nc(-c2cnccc2)cc2nc(-c3ccc[o]3)n[n]12 ZBJBBCUUKWBBGA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61P25/18—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
- A61P25/24—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33429301P | 2001-11-30 | 2001-11-30 | |
| US60/334,293 | 2001-11-30 | ||
| PCT/US2002/038134 WO2003048164A2 (en) | 2001-11-30 | 2002-11-26 | Adenosine a2a receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2468681A1 CA2468681A1 (en) | 2003-06-12 |
| CA2468681C true CA2468681C (en) | 2011-01-25 |
Family
ID=23306533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2468681A Expired - Fee Related CA2468681C (en) | 2001-11-30 | 2002-11-26 | Adenosine a2a receptor antagonists |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7041666B2 (https=) |
| EP (1) | EP1453835B1 (https=) |
| JP (2) | JP4284181B2 (https=) |
| KR (1) | KR20050044607A (https=) |
| CN (1) | CN1596258A (https=) |
| AR (1) | AR038366A1 (https=) |
| AT (1) | ATE317844T1 (https=) |
| AU (1) | AU2002346572A1 (https=) |
| CA (1) | CA2468681C (https=) |
| DE (1) | DE60209251T2 (https=) |
| ES (1) | ES2258164T3 (https=) |
| HU (1) | HUP0402270A3 (https=) |
| IL (1) | IL161572A0 (https=) |
| MX (1) | MXPA04005156A (https=) |
| PE (1) | PE20030739A1 (https=) |
| TW (1) | TW200300686A (https=) |
| WO (1) | WO2003048164A2 (https=) |
| ZA (1) | ZA200404160B (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004029056A1 (ja) * | 2002-09-24 | 2004-04-08 | Kyowa Hakko Kogyo Co., Ltd. | [１，２，４]トリアゾロ[１，５−ｃ]ピリミジン誘導体 |
| TWI331036B (en) | 2002-12-19 | 2010-10-01 | Schering Corp | Adenosine a2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders |
| US20060106040A1 (en) | 2002-12-19 | 2006-05-18 | Michael Grzelak | Adenosine A2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders |
| WO2004092172A2 (en) * | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosin e receptor antagonists |
| WO2005039506A2 (en) * | 2003-10-24 | 2005-05-06 | Exelixis, Inc. | P70s6 kinase modulators and method of use |
| AR050926A1 (es) | 2004-09-03 | 2006-12-06 | Astrazeneca Ab | Derivados de benzamida como inhibidores de la histonadesacetilasa(hdac) |
| WO2006129626A1 (ja) * | 2005-05-30 | 2006-12-07 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]トリアゾロ[1,5-c]ピリミジン誘導体の製造法 |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| CA2687942A1 (en) * | 2007-05-24 | 2008-12-04 | Mitsubishi Tanabe Pharma Corporation | Therapeutic agent for cerebral infarction |
| CA2690748A1 (en) * | 2007-06-25 | 2008-12-31 | Neurogen Corporation | Piperazinyl oxoalkyl tetrahydro-beta-carbolines and related analogues |
| US20100093764A1 (en) * | 2008-10-13 | 2010-04-15 | Devraj Chakravarty | AMINES AND SULFOXIDES OF THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| US20100093756A1 (en) * | 2008-10-13 | 2010-04-15 | Berbay J Kent | HETEROARYL SUBSTITUTED THIENO[2,3-d]PYRIMIDINE AND THEIR USE AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| BRPI0921570A2 (pt) | 2008-11-25 | 2019-09-24 | Nissan Motor | membro condutor de eletricidade e célula de combustível de eletrólito de polímero utilizando o mesmo |
| WO2010126811A1 (en) * | 2009-04-27 | 2010-11-04 | Boehringer Ingelheim International Gmbh | Cxcr3 receptor antagonists |
| WO2011084985A1 (en) | 2010-01-07 | 2011-07-14 | Boehringer Ingelheim International Gmbh | Cxcr3 receptor antagonists |
| AU2011306358B2 (en) * | 2010-09-24 | 2014-08-14 | Impetis Biosciences Ltd. | Fused tricyclic compounds as adenosine receptor antagonist |
| WO2012127472A1 (en) * | 2011-03-22 | 2012-09-27 | Mapi Pharma Ltd. | Process and intermediates for the preparation of preladenant and related compounds |
| PL3611174T3 (pl) * | 2017-04-07 | 2022-08-08 | Medshine Discovery Inc. | Pochodne [1,2,4]triazolo[1,5-c]pirymidyny jako inhibitor receptora a2a |
| TWI877770B (zh) * | 2018-02-27 | 2025-03-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之咪唑并嘧啶及三唑并嘧啶 |
| PL3766884T3 (pl) * | 2018-04-28 | 2022-07-18 | Medshine Discovery Inc. | Postać krystaliczna i rodzaj soli związku triazolopirymidynowego oraz sposób jej wytwarzania |
| EP3810610A1 (en) * | 2018-05-18 | 2021-04-28 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| WO2020010197A1 (en) | 2018-07-05 | 2020-01-09 | Incyte Corporation | Fused pyrazine derivatives as a2a / a2b inhibitors |
| AR116315A1 (es) * | 2018-09-12 | 2021-04-21 | Dizal Jiangsu Pharmaceutical Co Ltd | Compuestos de triazolo-pirimidina y usos de los mismos |
| US12414952B2 (en) | 2018-11-20 | 2025-09-16 | Merck Sharp & Dohme Llc | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| AU2019383948A1 (en) | 2018-11-20 | 2021-05-20 | Merck Sharp & Dohme Llc | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| WO2020112700A1 (en) | 2018-11-30 | 2020-06-04 | Merck Sharp & Dohme Corp. | 9-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| AU2019388872A1 (en) | 2018-11-30 | 2021-05-27 | Merck Sharp & Dohme Llc | 7-, 8-, and 10-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| CA3124088A1 (en) | 2018-12-20 | 2020-06-25 | Incyte Corporation | Imidazopyridazine and imidazopyridine compounds as inhibitors of activin receptor-like kinase-2 |
| WO2020128036A1 (en) * | 2018-12-21 | 2020-06-25 | Ryvu Therapeutics S.A. | Modulators of the adenosine a2a receptor |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
| IT1264901B1 (it) | 1993-06-29 | 1996-10-17 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina |
| WO1995003806A1 (en) | 1993-07-27 | 1995-02-09 | Kyowa Hakko Kogyo Co., Ltd. | Remedy for parkinson's disease |
| IT1277392B1 (it) | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
| DE69820866T2 (de) * | 1997-03-24 | 2004-12-30 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]TRIAZOLO[1,5-c]PYRIMIDIN-DERIVATE |
| IT1291372B1 (it) | 1997-05-21 | 1999-01-07 | Schering Plough S P A | Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie |
| WO2000017201A1 (en) * | 1998-09-22 | 2000-03-30 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]TRIAZOLO[1,5-c]PYRIMIDINE DERIVATIVES |
| DE60110219T2 (de) | 2000-05-26 | 2006-03-09 | Schering Corp. | Adenosin a2a rezeptor antagonisten |
| JPWO2002079204A1 (ja) * | 2001-03-28 | 2004-07-22 | 協和醗酵工業株式会社 | ８−チアゾリル［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体 |
| IL161573A0 (en) | 2001-11-30 | 2004-09-27 | Schering Corp | [1,2,4]-TRIAZOLE BICYCLIC ADENOSINE A2a RECEPTOR ANTAGONISTS |
-
2002
- 2002-11-25 AR ARP020104528A patent/AR038366A1/es unknown
- 2002-11-25 TW TW091134178A patent/TW200300686A/zh unknown
- 2002-11-25 PE PE2002001128A patent/PE20030739A1/es not_active Application Discontinuation
- 2002-11-26 AU AU2002346572A patent/AU2002346572A1/en not_active Abandoned
- 2002-11-26 CA CA2468681A patent/CA2468681C/en not_active Expired - Fee Related
- 2002-11-26 DE DE60209251T patent/DE60209251T2/de not_active Expired - Lifetime
- 2002-11-26 MX MXPA04005156A patent/MXPA04005156A/es active IP Right Grant
- 2002-11-26 AT AT02784641T patent/ATE317844T1/de not_active IP Right Cessation
- 2002-11-26 HU HU0402270A patent/HUP0402270A3/hu unknown
- 2002-11-26 ES ES02784641T patent/ES2258164T3/es not_active Expired - Lifetime
- 2002-11-26 JP JP2003549354A patent/JP4284181B2/ja not_active Expired - Fee Related
- 2002-11-26 IL IL16157202A patent/IL161572A0/xx unknown
- 2002-11-26 EP EP02784641A patent/EP1453835B1/en not_active Expired - Lifetime
- 2002-11-26 KR KR1020047008031A patent/KR20050044607A/ko not_active Withdrawn
- 2002-11-26 WO PCT/US2002/038134 patent/WO2003048164A2/en not_active Ceased
- 2002-11-26 US US10/304,504 patent/US7041666B2/en not_active Expired - Lifetime
- 2002-11-26 CN CNA028239229A patent/CN1596258A/zh active Pending
-
2004
- 2004-05-27 ZA ZA200404160A patent/ZA200404160B/en unknown
-
2008
- 2008-06-04 JP JP2008147394A patent/JP2008303217A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60209251T2 (de) | 2006-11-09 |
| PE20030739A1 (es) | 2003-08-28 |
| AR038366A1 (es) | 2005-01-12 |
| KR20050044607A (ko) | 2005-05-12 |
| HUP0402270A2 (hu) | 2005-02-28 |
| TW200300686A (en) | 2003-06-16 |
| ES2258164T3 (es) | 2006-08-16 |
| ZA200404160B (en) | 2005-04-08 |
| HUP0402270A3 (en) | 2008-09-29 |
| MXPA04005156A (es) | 2004-08-11 |
| ATE317844T1 (de) | 2006-03-15 |
| EP1453835A2 (en) | 2004-09-08 |
| CN1596258A (zh) | 2005-03-16 |
| IL161572A0 (en) | 2004-09-27 |
| US7041666B2 (en) | 2006-05-09 |
| AU2002346572A1 (en) | 2003-06-17 |
| CA2468681A1 (en) | 2003-06-12 |
| HK1064100A1 (en) | 2005-01-21 |
| JP4284181B2 (ja) | 2009-06-24 |
| EP1453835B1 (en) | 2006-02-15 |
| US20030212080A1 (en) | 2003-11-13 |
| JP2008303217A (ja) | 2008-12-18 |
| JP2005511698A (ja) | 2005-04-28 |
| WO2003048164A2 (en) | 2003-06-12 |
| DE60209251D1 (de) | 2006-04-20 |
| WO2003048164A3 (en) | 2003-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20131126 |