DE60331724D1 - Verwendung von bestimmten lösungsmitteln zur herstellung von bisphosphonsäuren - Google Patents
Verwendung von bestimmten lösungsmitteln zur herstellung von bisphosphonsäurenInfo
- Publication number
- DE60331724D1 DE60331724D1 DE60331724T DE60331724T DE60331724D1 DE 60331724 D1 DE60331724 D1 DE 60331724D1 DE 60331724 T DE60331724 T DE 60331724T DE 60331724 T DE60331724 T DE 60331724T DE 60331724 D1 DE60331724 D1 DE 60331724D1
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- bisphosphonic acids
- certain solvents
- acid
- diluent
- 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
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- -1 risedronic acid Chemical class 0.000 abstract 1
- 229960000759 risedronic acid Drugs 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38128402P | 2002-05-17 | 2002-05-17 | |
| US40131302P | 2002-08-06 | 2002-08-06 | |
| US42333702P | 2002-11-01 | 2002-11-01 | |
| US43183802P | 2002-12-09 | 2002-12-09 | |
| US45019303P | 2003-02-25 | 2003-02-25 | |
| PCT/US2003/015676 WO2003097655A1 (en) | 2002-05-17 | 2003-05-19 | Use of certain diluents for making bisphosphonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE60331724D1 true DE60331724D1 (de) | 2010-04-29 |
Family
ID=29554537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60331724T Expired - Fee Related DE60331724D1 (de) | 2002-05-17 | 2003-05-19 | Verwendung von bestimmten lösungsmitteln zur herstellung von bisphosphonsäuren |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US7038083B2 (de) |
| EP (1) | EP1476451B1 (de) |
| JP (1) | JP3857706B2 (de) |
| KR (1) | KR100681282B1 (de) |
| CN (1) | CN1665825A (de) |
| AT (1) | ATE461205T1 (de) |
| AU (1) | AU2003233569A1 (de) |
| CA (2) | CA2657002A1 (de) |
| DE (1) | DE60331724D1 (de) |
| IL (1) | IL165227A0 (de) |
| PL (1) | PL373574A1 (de) |
| WO (1) | WO2003097655A1 (de) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0215413A (pt) * | 2001-12-24 | 2004-12-14 | Teva Pharma | Formula dosada com um comprimido central de ingrediente ativo encapado em uma capa anular prensada de material em pó ou granulado e processo e conjunto de ferramentas para a sua produção |
| US20040052843A1 (en) * | 2001-12-24 | 2004-03-18 | Lerner E. Itzhak | Controlled release dosage forms |
| WO2003097655A1 (en) * | 2002-05-17 | 2003-11-27 | Teva Pharmaceutical Industries Ltd. | Use of certain diluents for making bisphosphonic acids |
| PT1656386E (pt) | 2003-08-21 | 2010-03-05 | Sun Pharmaceuticals Ind Ltd | Processo para a preparação de compostos de ácido bifosfónico |
| DE602004032577D1 (de) * | 2003-12-23 | 2011-06-16 | Alchymars S P A | Amorphe Form das Natriumsalzes der Ibandronsäure |
| WO2005063717A1 (en) * | 2003-12-26 | 2005-07-14 | Natco Pharma Limited | An improved process for the preparation of zoledronic acid |
| MX2007000087A (es) * | 2004-06-23 | 2007-11-06 | Teva Pharma | Acido ibandronico solido y cristalino. |
| WO2006039721A2 (en) | 2004-10-08 | 2006-04-13 | The Board Of Trustees Of The University Of Illinois | Bisphosphonate compounds and methods for bone resorption diseases, cancer, bone pain, immune disorders, and infectious diseases |
| US8012949B2 (en) | 2004-10-08 | 2011-09-06 | The Board Of Trustees Of The University Of Illinois | Bisphosphonate compounds and methods with enhanced potency for multiple targets including FPPS, GGPPS, and DPPS |
| US7214818B2 (en) * | 2004-10-29 | 2007-05-08 | Hoffmann-La Roche Inc. | Method for synthesizing bisphosphonate |
| PL199215B1 (pl) * | 2004-12-28 | 2008-08-29 | Politechnika Gdanska | Sposób wytwarzania kwasu [1-hydroksy-2-(3-pirydylo)etylidenobisfosfonowego] oraz jego soli monosodowej dwu i pół wodnej |
| EP1891081B1 (de) * | 2005-06-13 | 2014-08-20 | Jubilant Organosys Limited | Verfahren zur herstellung von bisphosphonsäuren und formen davon |
| US8003820B2 (en) * | 2005-10-20 | 2011-08-23 | Dr. Reddy's Laboratories Limited | Process for preparing bisphosphonic acids |
| WO2007069049A2 (en) * | 2005-12-16 | 2007-06-21 | Wockhardt Ltd | Processes for the preparation of pure zoledronic acid |
| WO2007083240A2 (en) * | 2006-01-20 | 2007-07-26 | Aurobindo Pharma Limited | An improved process for the preparation of bisphosphonic acids |
| KR20080111070A (ko) | 2006-03-17 | 2008-12-22 | 더 보오드 오브 트러스티스 오브 더 유니버시티 오브 일리노이즈 | 비스포스포네이트 화합물 및 방법 |
| CN101421284A (zh) * | 2006-04-25 | 2009-04-29 | 特瓦制药工业有限公司 | 伊班膦酸的结晶形式和其制备方法 |
| WO2007125521A2 (en) * | 2006-05-02 | 2007-11-08 | Ranbaxy Laboratories Limited | Polymorphic form of zoledronic acid and processes for their preparation |
| JP5354858B2 (ja) * | 2006-05-09 | 2013-11-27 | 株式会社Ａｄｅｋａ | スルホンアミド化合物の金属塩を含有するポリエステル樹脂組成物 |
| KR20090005206A (ko) | 2006-05-11 | 2009-01-12 | 인드-스위프트 래버러토리즈 리미티드 | 순수한 리세드론산 또는 염의 제조 방법 |
| WO2008044245A2 (en) * | 2006-10-10 | 2008-04-17 | Matrix Laboratories Ltd | A process for the preparation of risedronate sodium hemipentahydrate |
| CA2570949A1 (en) * | 2006-12-12 | 2008-06-12 | Apotex Pharmachem Inc. | Ibandronate sodium propylene glycol solvate and processes for the preparation thereof |
| EP2144919B1 (de) * | 2007-04-11 | 2015-12-02 | F. Hoffmann-La Roche AG | Mehrstufige synthese von ibandronat |
| US7605148B2 (en) * | 2007-04-16 | 2009-10-20 | Aurobindo Pharma Ltd. | Aqueous oral solution of bisphosphonic acid |
| US20100317859A1 (en) * | 2007-05-16 | 2010-12-16 | Actavis Group Ptc Ehf | Process for the Preparation of Risedronate Sodium |
| WO2009050731A2 (en) * | 2007-06-20 | 2009-04-23 | Alkem Laboratories Ltd | Novel process for preparing risedronic acid |
| KR100877667B1 (ko) | 2007-06-28 | 2009-01-08 | 보령제약 주식회사 | 리세드로네이트의 제조 방법 |
| WO2009034580A1 (en) * | 2007-09-11 | 2009-03-19 | Fleming Laboratories Limited | Improved process for the preparation of risedronate sodium hemipentahydrate |
| JP5258370B2 (ja) * | 2008-05-08 | 2013-08-07 | ダイト株式会社 | リセドロン酸の工業的製造方法 |
| WO2010003704A2 (en) * | 2008-07-11 | 2010-01-14 | Synthon B.V. | Process for making 1-hydroxyalkylidene-1,1-biphosphonic acids |
| PL213599B1 (pl) | 2008-10-31 | 2013-03-29 | Politechnika Gdanska | Sposób otrzymywania kwasu [1-hydroksy-2-(1H-imidazol-1-ilo)-etylideno] bisfosfonowego |
| EP2192126B1 (de) | 2008-11-26 | 2013-03-27 | Synthon B.V. | Verfahren zur Herstellung von Zoledronsäure |
| WO2010060619A1 (en) * | 2008-11-26 | 2010-06-03 | Synthon B.V. | Process for making zoledronic acid |
| US20100130746A1 (en) * | 2008-11-26 | 2010-05-27 | Martin Kas | Process for Making Zoledronic Acid |
| AU2010278860B2 (en) | 2009-07-31 | 2016-05-26 | Thar Pharma, Llc | Crystallization method and bioavailability |
| US9169279B2 (en) | 2009-07-31 | 2015-10-27 | Thar Pharmaceuticals, Inc. | Crystallization method and bioavailability |
| US20160016982A1 (en) | 2009-07-31 | 2016-01-21 | Thar Pharmaceuticals, Inc. | Crystallization method and bioavailability |
| WO2011016738A1 (en) | 2009-08-05 | 2011-02-10 | Zaklady Farmaceutyczne Polpharma Sa | A process for the synthesis of 1-hydroxy-3-(n-methylpentylamino) propylidene bisphosphonic acid monosodium salt, monohydrate |
| EP2470549B1 (de) | 2009-08-28 | 2014-07-16 | Synthon B.V. | Verfahren zur herstellung von hydroxyalkyliden-1,1-biphosphonsäuren |
| US8882740B2 (en) * | 2009-12-23 | 2014-11-11 | Stryker Trauma Gmbh | Method of delivering a biphosphonate and/or strontium ranelate below the surface of a bone |
| US9340565B2 (en) | 2010-11-24 | 2016-05-17 | Thar Pharmaceuticals, Inc. | Crystalline forms |
| US10195218B2 (en) | 2016-05-31 | 2019-02-05 | Grunenthal Gmbh | Crystallization method and bioavailability |
| EP3553067A1 (de) * | 2018-04-10 | 2019-10-16 | Abiogen Pharma S.p.A. | Polymorph von natriumneridronat und herstellungsverfahren dafür |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3016289A1 (de) * | 1980-04-28 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren |
| IT1201087B (it) * | 1982-04-15 | 1989-01-27 | Gentili Ist Spa | Bifosfonati farmacologicamente attivi,procedimento per la loro preparazione e relative composizioni farmaceutiche |
| IT1196315B (it) * | 1984-10-29 | 1988-11-16 | Gentili Ist Spa | Procedimento per la preparazione di acidi difosfonici |
| DE3623397A1 (de) * | 1986-07-11 | 1988-01-14 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3700772A1 (de) | 1987-01-13 | 1988-07-21 | Inst Khim Kinetiki I Gorenija | Verfahren zur herstellung von i-funktionellsubstituierten alkyliden-i,i-diphosphonsaeuren und deren gemischen |
| US4922007A (en) * | 1989-06-09 | 1990-05-01 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof |
| US5019651A (en) * | 1990-06-20 | 1991-05-28 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof |
| US5159108A (en) * | 1990-09-18 | 1992-10-27 | Merck & Co., Inc. | Process for preparing an antihypercalcemic agent |
| US5039819A (en) * | 1990-09-18 | 1991-08-13 | Merck & Co., Inc. | Diphosphonate intermediate for preparing an antihypercalcemic agent |
| US5327490A (en) * | 1991-02-19 | 1994-07-05 | Intervoice, Inc. | System and method for controlling call placement rate for telephone communication systems |
| US5358941A (en) * | 1992-12-02 | 1994-10-25 | Merck & Co., Inc. | Dry mix formulation for bisphosphonic acids with lactose |
| TW257765B (de) * | 1993-08-25 | 1995-09-21 | Merck & Co Inc | |
| US5510517A (en) * | 1993-08-25 | 1996-04-23 | Merck & Co., Inc. | Process for producing N-amino-1-hydroxy-alkylidene-1,1-bisphosphonic acids |
| US5449819A (en) * | 1994-06-06 | 1995-09-12 | Merck & Co., Inc. | Process for removing waste pox, alendronate and its by products |
| US5589691A (en) * | 1994-06-06 | 1996-12-31 | Merck & Co., Inc. | Process for recovery and recycle of methanesulfonic acid and phosphorous acid |
| JP3349032B2 (ja) * | 1996-03-15 | 2002-11-20 | 株式会社東芝 | 発呼制御方法 |
| KR100192215B1 (ko) | 1996-09-03 | 1999-06-15 | 강재헌 | 3-아미노-1-히드록시프로판-1,1-디포스폰산의 제조방법 |
| CA2197267C (en) * | 1997-02-11 | 2000-02-08 | Yong Tao | Process for the production of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof |
| ES2153794B1 (es) * | 1999-08-06 | 2001-10-16 | Medichem Sa | Procedimiento para la obtencion del acido 4-amino-1-hidroxibutiliden-1,1-bisfosfonico y de su sal monosodica trihidratada. |
| PE20011065A1 (es) | 2000-02-01 | 2001-11-21 | Procter & Gamble | Proceso para fabricar bisfosfonatos geminales |
| TR200101250A2 (tr) | 2001-05-10 | 2003-04-21 | E�S Eczaciba�I �Zg�N K�Myasal �R�Nler Sanay� A.�. | 4-amino-1-hidroksibutiliden-1,1-bifosfonik asit veya tuzlarının hazırlanmasına ilişkin proses |
| GB0115824D0 (en) * | 2001-06-28 | 2001-08-22 | Rhodia Cons Spec Ltd | Improved solvent systems |
| US6645974B2 (en) * | 2001-07-31 | 2003-11-11 | Merck & Co., Inc. | Androgen receptor modulators and methods for use thereof |
| ITMI20020908A1 (it) * | 2002-04-29 | 2003-10-29 | Chemi Spa | Processo di preparazione di sodio alendronato |
| WO2003097655A1 (en) * | 2002-05-17 | 2003-11-27 | Teva Pharmaceutical Industries Ltd. | Use of certain diluents for making bisphosphonic acids |
| HUP0300227A2 (hu) * | 2003-01-28 | 2004-09-28 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás nagy tisztaságú 2-szubsztituált -1-(hidroxi-etilidén)-1,1-biszfoszfonsavak és sóik előállítására |
| PT1656386E (pt) * | 2003-08-21 | 2010-03-05 | Sun Pharmaceuticals Ind Ltd | Processo para a preparação de compostos de ácido bifosfónico |
| DE602004032577D1 (de) * | 2003-12-23 | 2011-06-16 | Alchymars S P A | Amorphe Form das Natriumsalzes der Ibandronsäure |
| US7361761B2 (en) * | 2004-09-28 | 2008-04-22 | Orchid Chemicals & Pharmaceuticals Ltd. | Process for the preparation of bisphosphonic acid |
| US8003820B2 (en) * | 2005-10-20 | 2011-08-23 | Dr. Reddy's Laboratories Limited | Process for preparing bisphosphonic acids |
| ES2323728T3 (es) * | 2005-12-27 | 2009-07-23 | Ipca Laboratories Limited | Proceso mejorado para la fabricacion de 4-amino-hidroxibutilideno-1,1-bisfosfonico y sus sales. |
| WO2007083240A2 (en) * | 2006-01-20 | 2007-07-26 | Aurobindo Pharma Limited | An improved process for the preparation of bisphosphonic acids |
| WO2007096896A1 (en) * | 2006-02-20 | 2007-08-30 | Alembic Limited | An improved process for the preparation of biphosphonic derivatives |
-
2003
- 2003-05-19 WO PCT/US2003/015676 patent/WO2003097655A1/en active Application Filing
- 2003-05-19 KR KR1020047018564A patent/KR100681282B1/ko not_active IP Right Cessation
- 2003-05-19 DE DE60331724T patent/DE60331724D1/de not_active Expired - Fee Related
- 2003-05-19 JP JP2004505386A patent/JP3857706B2/ja not_active Expired - Lifetime
- 2003-05-19 CA CA002657002A patent/CA2657002A1/en not_active Abandoned
- 2003-05-19 AU AU2003233569A patent/AU2003233569A1/en not_active Abandoned
- 2003-05-19 IL IL16522703A patent/IL165227A0/xx unknown
- 2003-05-19 US US10/442,001 patent/US7038083B2/en not_active Expired - Fee Related
- 2003-05-19 CN CN038160226A patent/CN1665825A/zh active Pending
- 2003-05-19 PL PL03373574A patent/PL373574A1/xx not_active Application Discontinuation
- 2003-05-19 CA CA2485443A patent/CA2485443C/en not_active Expired - Fee Related
- 2003-05-19 EP EP03729005A patent/EP1476451B1/de not_active Expired - Lifetime
- 2003-05-19 AT AT03729005T patent/ATE461205T1/de not_active IP Right Cessation
-
2006
- 2006-02-08 US US11/350,462 patent/US20060128960A1/en not_active Abandoned
-
2009
- 2009-02-10 US US12/368,805 patent/US20090209763A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP3857706B2 (ja) | 2006-12-13 |
| KR20040111633A (ko) | 2004-12-31 |
| IL165227A0 (en) | 2005-12-18 |
| CA2657002A1 (en) | 2003-11-27 |
| EP1476451B1 (de) | 2010-03-17 |
| AU2003233569A1 (en) | 2003-12-02 |
| EP1476451A1 (de) | 2004-11-17 |
| CA2485443A1 (en) | 2003-11-27 |
| US20060128960A1 (en) | 2006-06-15 |
| ATE461205T1 (de) | 2010-04-15 |
| WO2003097655A1 (en) | 2003-11-27 |
| JP2005526140A (ja) | 2005-09-02 |
| US7038083B2 (en) | 2006-05-02 |
| KR100681282B1 (ko) | 2007-02-12 |
| PL373574A1 (en) | 2005-09-05 |
| CA2485443C (en) | 2010-04-06 |
| CN1665825A (zh) | 2005-09-07 |
| US20090209763A1 (en) | 2009-08-20 |
| US20040043967A1 (en) | 2004-03-04 |
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