HRP20070246T5 - Process for the synthesis of ivabradine and its pharmaceutically acceptable acid addition salts - Google Patents
Process for the synthesis of ivabradine and its pharmaceutically acceptable acid addition saltsInfo
- Publication number
- HRP20070246T5 HRP20070246T5 HR20070246T HRP20070246T HRP20070246T5 HR P20070246 T5 HRP20070246 T5 HR P20070246T5 HR 20070246 T HR20070246 T HR 20070246T HR P20070246 T HRP20070246 T HR P20070246T HR P20070246 T5 HRP20070246 T5 HR P20070246T5
- Authority
- HR
- Croatia
- Prior art keywords
- ivabradine
- pharmaceutically acceptable
- formula
- acceptable acid
- synthesis
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 4
- ACRHBAYQBXXRTO-OAQYLSRUSA-N ivabradine Chemical compound C1CC2=CC(OC)=C(OC)C=C2CC(=O)N1CCCN(C)C[C@H]1CC2=C1C=C(OC)C(OC)=C2 ACRHBAYQBXXRTO-OAQYLSRUSA-N 0.000 title abstract 4
- 229960003825 ivabradine Drugs 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 2
- -1 1 , 3-dioxolanyl 1,3-dioxepan Chemical compound 0.000 abstract 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C11/00—Details of pavings
- E01C11/16—Reinforcements
- E01C11/165—Reinforcements particularly for bituminous or rubber- or plastic-bound pavings
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Architecture (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0403830A FR2868777B1 (fr) | 2004-04-13 | 2004-04-13 | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20070246T3 HRP20070246T3 (en) | 2007-08-31 |
| HRP20070246T5 true HRP20070246T5 (en) | 2008-10-31 |
Family
ID=34941959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20070246T HRP20070246T5 (en) | 2004-04-13 | 2007-05-29 | Process for the synthesis of ivabradine and its pharmaceutically acceptable acid addition salts |
Country Status (43)
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2868776B1 (fr) * | 2004-04-13 | 2008-04-18 | Servier Lab | Nouveau procede de synthese de derives de la 1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2868775B1 (fr) * | 2004-04-13 | 2008-04-11 | Servier Lab | Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2882554B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme critalline beta d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2882553B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline beta du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2882556B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2882555B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2891826B1 (fr) | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline 6 du chlorhydrate de l'ivabradine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2891827B1 (fr) * | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline deltad du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2894826B1 (fr) * | 2005-12-21 | 2010-10-22 | Servier Lab | Nouvelle association d'un inhibiteur du courant if sinusal et d'un inhibiteur calcique et les compositions pharmaceutiques qui la contiennent |
| ES2381771T3 (es) | 2006-11-30 | 2012-05-31 | Cadila Healthcare Limited | Procedimiento para la preparación de hidrocloruro de ivabradina |
| WO2008125006A1 (fr) * | 2007-04-12 | 2008-10-23 | Utopharm (Shanghai) Co., Ltd | Procédés de préparation du chlorhydrate d'ivabradine et de sa forme cristalline stable |
| US8212026B2 (en) | 2007-05-30 | 2012-07-03 | Ind-Swift Laboratories Limited | Process for the preparation of ivabradine hydrochloride and polymorph thereof |
| SI22750A (sl) * | 2008-04-07 | 2009-10-31 | Krka D.D. | Ivabradin hidrobromid |
| FR2932800B1 (fr) | 2008-06-20 | 2015-02-20 | Servier Lab | Nouveau procede de synthese de la 7,8-dimethoxy-1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2933975B1 (fr) | 2008-07-17 | 2011-02-18 | Servier Lab | Nouveau procede de preparation de benzocyclobutenes fonctionnalises,et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| FR2935381B1 (fr) | 2008-08-29 | 2010-12-17 | Servier Lab | Nouveau procede de resolution des enantiomerees du (3,4-dimethoxy-bicyclo°4.2.0!octa-1,3,5-trien-7-yl)nitrile et application a la synthese de l'ivabradine |
| CN101723897B (zh) * | 2008-10-31 | 2011-11-16 | 齐鲁制药有限公司 | 伊伐布雷定的合成方法 |
| EP2367782B1 (en) | 2008-12-22 | 2013-02-13 | KRKA, D.D., Novo Mesto | Process for preparation of ivabradine |
| FR2940287B1 (fr) * | 2008-12-24 | 2010-12-24 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| CN101768117B (zh) * | 2008-12-29 | 2014-05-07 | 北京德众万全药物技术开发有限公司 | 一种盐酸伊伐布雷定晶型及其制备方法 |
| CN101768116B (zh) * | 2008-12-29 | 2014-06-18 | 北京德众万全药物技术开发有限公司 | 一种伊伐布雷定的制备方法 |
| FR2941695B1 (fr) * | 2009-02-04 | 2011-02-18 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| ME00986B (me) | 2009-03-31 | 2012-06-20 | Servier Lab | Novi postupak sinteze ivabradina i njegovih adicionih soli sa farmaceutski prihvatljivom kiselinom |
| FR2943667B1 (fr) * | 2009-03-31 | 2011-05-06 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| WO2010128525A2 (en) | 2009-05-04 | 2010-11-11 | Dinesh Shantilal Patel | A formulation of ivabradine for treating the cardiovascular disease |
| SI23290A (sl) | 2010-02-12 | 2011-08-31 | Krka D.D., Novo Mesto | Nove oblike ivabradin hidroklorida |
| FR2956401B1 (fr) * | 2010-02-17 | 2012-02-03 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| WO2011104723A2 (en) * | 2010-02-23 | 2011-09-01 | Ind-Swift Laboratories Limited | Acid addition salts of ivabradine and preparation thereof |
| HUP1000245A2 (en) * | 2010-05-07 | 2011-11-28 | Richter Gedeon Nyrt | Industrial process for the production ivabradin salts |
| TWI499587B (zh) * | 2010-06-03 | 2015-09-11 | Jiangsu Hengrui Medicine Co | 硫酸伊伐佈雷定及其ｉ型結晶的製備方法 |
| PT2579858E (pt) | 2010-06-14 | 2014-07-18 | Ratiopharm Gmbh | Composição farmacêutica que contém ivabradina |
| WO2012025940A1 (en) | 2010-08-25 | 2012-03-01 | Cadila Healthcare Limited | Polymorphic form of ivabradine hydrochloride and process for preparation thereof |
| FR2971507B1 (fr) * | 2011-02-14 | 2013-01-18 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| CN102304088B (zh) * | 2011-07-07 | 2013-06-19 | 石药集团欧意药业有限公司 | 一种伊伐布雷定化合物、制备方法及其药物组合物 |
| EP2726462B1 (en) | 2011-08-02 | 2017-03-22 | Sandoz AG | Acetone solvate of ivabradine hydrochloride |
| EP2773621B1 (en) | 2011-11-04 | 2015-12-30 | Synthon BV | A process for making crystalline delta-form of ivabradine hydrochloride |
| EP2589594A1 (en) | 2011-11-04 | 2013-05-08 | Urquima S.A. | Ivabradine hydrochloride Form IV |
| WO2013102919A1 (en) | 2011-11-14 | 2013-07-11 | Cadila Healthcare Limited | Polymorphic forms of ivabradine hydrochloride |
| FR2984320B1 (fr) * | 2011-12-20 | 2013-11-29 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2984319B1 (fr) * | 2011-12-20 | 2013-12-27 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2986804A1 (fr) * | 2012-02-09 | 2013-08-16 | Servier Lab | Procede de synthese enzymatique de l'acide (7s) 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene 7-carboxylique ou de ses esters, et application a la synthese de l'ivabradine et de ses sels |
| FR2988720B1 (fr) * | 2012-03-27 | 2014-03-14 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2993561B1 (fr) * | 2012-07-17 | 2014-10-31 | Servier Lab | Procede de synthese enzymatique de la (7s)-1-(3,4-dimethoxy bicyclo[4.2.0]octa-1,3,5-triene 7-yl) n-methyl methanamine, et application a la synthese de l'ivabradine et de ses sels |
| CN103848789B (zh) * | 2012-11-29 | 2016-05-18 | 江苏恒瑞医药股份有限公司 | 一种伊伐布雷定的制备方法 |
| CN103012268B (zh) * | 2013-01-05 | 2015-02-25 | 江苏宇田生物医药科技有限公司 | 一种伊伐布雷定制备方法 |
| EP2948432B1 (en) | 2013-01-24 | 2018-09-19 | Synthon BV | Process for making ivabradine |
| ITMI20130684A1 (it) * | 2013-04-24 | 2014-10-25 | Chemo Res S L | Nuovo polimorfo del cloridrato di ivabradina e metodo per la sua preparazione |
| ITMI20130416A1 (it) * | 2013-03-19 | 2014-09-20 | Chemo Res S L | Nuovo polimorfo del cloridrato di ivabradina e metodo per la sua preparazione |
| EP2781509B2 (en) | 2013-03-19 | 2023-06-14 | Chemo Research, S.L. | New polymorph of ivabradine hydrochloride and method for its preparation |
| CZ2013767A3 (cs) | 2013-10-02 | 2015-04-29 | Zentiva, K.S. | Pevná forma Ivabradin hydrochloridu a (S)-mandlové kyseliny a její farmaceutická kompozice |
| MX363389B (es) | 2013-12-12 | 2019-03-20 | Synthon Bv | Composicion farmaceutica que comprende ivabradina amorfa. |
| CN103864690B (zh) * | 2014-01-06 | 2016-09-14 | 北京莱瑞森医药科技有限公司 | 伊伐布雷定盐酸盐的s晶型、其制备方法和药物组合物 |
| ES2717715T3 (es) | 2014-02-14 | 2019-06-24 | Synthon Bv | Composición farmacéutica que comprende polimorfo IV de clorhidrato de ivabradina |
| CN103880748B (zh) * | 2014-04-03 | 2015-09-16 | 南京正大天晴制药有限公司 | 一种盐酸伊伐布雷定结构类似物及其制备方法和应用 |
| CZ2014478A3 (cs) | 2014-07-10 | 2015-09-16 | Zentiva, K.S. | Pevná forma Ivabradin hydrochloridu a (R)-mandlové kyseliny a její farmaceutická kompozice |
| WO2016102423A1 (en) | 2014-12-22 | 2016-06-30 | Ratiopharm Gmbh | Composition comprising ivabradine in a dissolved form |
| EP3101010A1 (en) | 2015-06-03 | 2016-12-07 | Urquima S.A. | New method for the preparation of highly pure ivabradine base and salts thereof |
| CN107056706B (zh) * | 2015-12-21 | 2020-05-05 | 江苏恒瑞医药股份有限公司 | 一种用于制备盐酸伊伐布雷定α晶型的方法 |
| TR201703066A2 (tr) | 2017-02-28 | 2018-09-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | İvabradi̇ni̇n kati oral farmasöti̇k kompozi̇syonlari |
| EP3366282B1 (en) | 2017-02-28 | 2025-10-01 | Sanovel Ilac Sanayi ve Ticaret A.S. | Solid oral pharmaceutical compositions of ivabradine |
| US20230140818A1 (en) | 2017-04-27 | 2023-05-04 | The University Of Hong Kong | Use of hcn inhibitors for treatment of cancer |
| US20230181472A1 (en) | 2018-10-30 | 2023-06-15 | Amgen Inc. | Process of making ivabradine hydrochloride drug product |
| IT202000025312A1 (it) | 2020-10-26 | 2022-04-26 | Cambrex Profarmaco Milano S R L | Processi per la preparazione di polimorfi di ivabradina hcl |
| CN115286577B (zh) * | 2022-08-25 | 2023-10-20 | 江苏永安制药有限公司 | 一种盐酸伊伐布雷定及其中间体的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3119874A1 (de) | 1981-05-19 | 1982-12-09 | Dr. Karl Thomae Gmbh, 7950 Biberach | "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel" |
| DE3418270A1 (de) | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| EP0204349A3 (de) | 1985-06-01 | 1990-01-03 | Dr. Karl Thomae GmbH | Neue heteroaromatische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE3519735A1 (de) * | 1985-06-01 | 1986-12-04 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| FR2681862B1 (fr) | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
| FR2834896B1 (fr) * | 2002-01-23 | 2004-02-27 | Servier Lab | Composition pharmaceutique orodispersible d'ivabradine |
| FR2868776B1 (fr) * | 2004-04-13 | 2008-04-18 | Servier Lab | Nouveau procede de synthese de derives de la 1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2868775B1 (fr) * | 2004-04-13 | 2008-04-11 | Servier Lab | Nouveau procede de synthese de derives de la 1,3,4,5- tetrahydro-2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2882556B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2882554B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme critalline beta d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2882555B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2882553B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline beta du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2891827B1 (fr) * | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline deltad du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2891826B1 (fr) * | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline 6 du chlorhydrate de l'ivabradine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
-
2004
- 2004-04-13 FR FR0403830A patent/FR2868777B1/fr not_active Expired - Fee Related
-
2005
- 2005-02-07 CA CA2496723A patent/CA2496723C/fr not_active Expired - Lifetime
- 2005-02-07 AP AP2005003222A patent/AP1821A/xx active
- 2005-02-14 CU CU20050034A patent/CU23465B7/es unknown
- 2005-02-14 US US11/057,492 patent/US7176197B2/en not_active Expired - Lifetime
- 2005-02-15 CR CR7691A patent/CR7691A/es unknown
- 2005-02-15 CO CO05013707A patent/CO5670092A1/es not_active Application Discontinuation
- 2005-02-15 SG SG200500771A patent/SG116575A1/en unknown
- 2005-02-17 EC EC2005005610A patent/ECSP055610A/es unknown
- 2005-02-18 MY MYPI20050620A patent/MY141194A/en unknown
- 2005-02-18 NO NO20050884A patent/NO329807B1/no unknown
- 2005-02-18 AR ARP050100588A patent/AR047745A1/es active IP Right Grant
- 2005-02-18 OA OA1200500056A patent/OA12913A/en unknown
- 2005-02-18 CN CNB2005100517790A patent/CN1305856C/zh not_active Expired - Lifetime
- 2005-02-18 UA UAA200501522A patent/UA80834C2/xx unknown
- 2005-02-18 MA MA28114A patent/MA27600A1/fr unknown
- 2005-02-18 UY UY28759A patent/UY28759A1/es not_active Application Discontinuation
- 2005-02-18 GE GEAP8649A patent/GEP20074138B/en unknown
- 2005-02-18 JP JP2005041812A patent/JP4515934B2/ja not_active Expired - Lifetime
- 2005-02-18 NI NI200500031A patent/NI200500031A/es unknown
- 2005-02-18 NZ NZ538326A patent/NZ538326A/en not_active IP Right Cessation
- 2005-02-18 AU AU2005200861A patent/AU2005200861B2/en not_active Expired
- 2005-02-18 ZA ZA2005/01466A patent/ZA200501466B/en unknown
- 2005-02-19 KR KR1020050013859A patent/KR100677019B1/ko not_active Expired - Lifetime
- 2005-02-19 SA SA05260016A patent/SA05260016B1/ar unknown
- 2005-02-21 ES ES05290381T patent/ES2285651T3/es not_active Expired - Lifetime
- 2005-02-21 PT PT05290381T patent/PT1589005E/pt unknown
- 2005-02-21 DE DE602005000765T patent/DE602005000765T2/de not_active Expired - Lifetime
- 2005-02-21 SI SI200530017T patent/SI1589005T1/sl unknown
- 2005-02-21 BR BRPI0500585A patent/BRPI0500585B8/pt not_active IP Right Cessation
- 2005-02-21 DK DK05290381T patent/DK1589005T3/da active
- 2005-02-21 ME MEP-2007-219A patent/ME01396B/me unknown
- 2005-02-21 PL PL05290381T patent/PL1589005T3/pl unknown
- 2005-02-21 EP EP05290381A patent/EP1589005B1/fr not_active Expired - Lifetime
- 2005-02-21 AT AT05290381T patent/ATE358123T1/de active
- 2005-02-21 IL IL167013A patent/IL167013A/en active IP Right Grant
- 2005-02-21 EA EA200500238A patent/EA007745B1/ru unknown
- 2005-02-21 RS RSP-2007/0219A patent/RS50511B/sr unknown
- 2005-02-21 WO PCT/FR2005/000394 patent/WO2005110993A1/fr not_active Ceased
- 2005-04-07 MX MXPA05003694A patent/MXPA05003694A/es active IP Right Grant
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2006
- 2006-01-05 HK HK06100189.5A patent/HK1080362B/zh not_active IP Right Cessation
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2007
- 2007-01-18 US US11/654,719 patent/US7867994B2/en active Active
- 2007-05-16 CY CY20071100664T patent/CY1106597T1/el unknown
- 2007-05-29 HR HR20070246T patent/HRP20070246T5/xx unknown
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2009
- 2009-09-25 JP JP2009220557A patent/JP4848449B2/ja not_active Expired - Lifetime
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2010
- 2010-11-05 CR CR11780A patent/CR11780A/es unknown
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