DK1618111T3 - Salte af clopidogrel samt fremgangsmåde til fremstilling - Google Patents
Salte af clopidogrel samt fremgangsmåde til fremstilling Download PDFInfo
- Publication number
- DK1618111T3 DK1618111T3 DK04770646.0T DK04770646T DK1618111T3 DK 1618111 T3 DK1618111 T3 DK 1618111T3 DK 04770646 T DK04770646 T DK 04770646T DK 1618111 T3 DK1618111 T3 DK 1618111T3
- Authority
- DK
- Denmark
- Prior art keywords
- clopidogrel
- butyl
- besylate
- salts
- crystalline
- Prior art date
Links
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical class C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 title claims description 63
- 150000003839 salts Chemical class 0.000 title claims description 39
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 title claims description 31
- 229960003009 clopidogrel Drugs 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- 229950010557 clopidogrel besilate Drugs 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000009805 platelet accumulation Effects 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000012453 solvate Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 208000024172 Cardiovascular disease Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229940127218 antiplatelet drug Drugs 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- -1 sulfonic acids salts Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 229940124345 antianginal agent Drugs 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003958 clopidogrel bisulfate Drugs 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 229940049636 dobesilic acid Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical class OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940020573 plavix Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Claims (6)
1. Krystallinsk clopidogrelbesylat med et pulver-røntgendiffraktionsmønster som vist i fig. 2 og med et smeltepunkt i området 124 - 132 °C.
2. Krystallinsk clopidogrelbesylat ifølge krav 1, indeholdende 0,1 - 0,3 vægt-% vand.
3. Fremgangsmåde til fremstilling af krystallinsk clopidogrelbesylat ifølge ethvert af de foregående krav, omfattende følgende trin: i) opløsning af clopidogrelbase i/bringe clopidogrelbase i kontakt med egnede opløsningsmidler, ii) behandling af produktet i trin (i) med benzensulfonsyre, iii) fjernelse af opløsningsmidlerne for at tilvejebringe saltet.
4. Fremgangsmåde ifølge krav 3, kendetegnet ved, at egnede opløsningsmidler er valgt blandt vand, n-heptan, cyclohexan, petroleumæter, ætere hvori hver al-kylradikal af æteren uafhængigt er valgt fra gruppen bestående af metyl, etyl, propyl, isopropyl, butyl, 1-butyl, 2-butyl og t-butyl, eller blandinger deraf.
5. Farmaceutisk sammensætning omfattende clopidogrelbesylat i krystallinsk form ifølge ethvert af krav 1 eller 2 samt et farmaceutisk acceptabelt bindemiddel.
6. Anvendelse af saltene af clopidogrel ifølge ethvert af krav 1 eller 2 til fremstilling af mediciner til behandling af sygdomme tilknyttet blodpladeansamling.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN413MU2003 | 2003-04-25 | ||
| PCT/IN2004/000112 WO2004106344A2 (en) | 2003-04-25 | 2004-04-22 | Salts of clopidogrel and process for preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK1618111T3 true DK1618111T3 (da) | 2015-02-16 |
Family
ID=33485475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK04770646.0T DK1618111T3 (da) | 2003-04-25 | 2004-04-22 | Salte af clopidogrel samt fremgangsmåde til fremstilling |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7732608B2 (da) |
| EP (4) | EP2113506A3 (da) |
| KR (1) | KR20060013376A (da) |
| CY (1) | CY1116554T1 (da) |
| DE (1) | DE04770646T1 (da) |
| DK (1) | DK1618111T3 (da) |
| ES (1) | ES2531088T3 (da) |
| HR (1) | HRP20150056T1 (da) |
| NO (1) | NO333586B1 (da) |
| PL (1) | PL1618111T3 (da) |
| PT (1) | PT1618111E (da) |
| SI (1) | SI1618111T1 (da) |
| WO (1) | WO2004106344A2 (da) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10305984A1 (de) * | 2003-02-13 | 2004-09-02 | Helm Ag | Salze organischer Säuren mit Clopidogrel und deren Verwendung zur Herstellung phamazeutischer Formulierungen |
| AU2003238664A1 (en) * | 2003-03-12 | 2004-09-30 | Cadila Healthcare Limited | Polymorphs and amorphous form of (s) - (+) -clopidogrel bisulfate |
| ES2531088T3 (es) * | 2003-04-25 | 2015-03-10 | Cadila Healthcare Ltd | Sales de clopidogrel y procedimiento de preparación |
| ATE455778T1 (de) * | 2003-11-03 | 2010-02-15 | Cadila Healthcare Ltd | Verfahren zur herstellung form i von (s)-(+)- clopidogrelbisulfat |
| CN1922188A (zh) * | 2004-02-24 | 2007-02-28 | 齐格弗里德通用国际股份公司 | 氯吡格雷之药学可接受的盐 |
| ZA200608035B (en) * | 2004-04-20 | 2008-07-30 | Sanofi Aventis | Clopidogrel salt and polymorphic forms thereof |
| WO2006074066A1 (en) * | 2004-12-30 | 2006-07-13 | Nektar Therapeutics | Non-crystalline formulation comprising clopidogrel |
| ES2391410T3 (es) | 2005-09-05 | 2012-11-26 | Cadila Healthcare Limited | Procedimientos para la preparación de diferentes formas de (s)-(+)-clopidogrel besilato |
| ATE498626T1 (de) * | 2006-09-25 | 2011-03-15 | Adamed Sp Zoo | Neues clopidogrel-salz und seine kristallinen formen |
| KR101378596B1 (ko) | 2006-12-27 | 2014-03-26 | 경동제약 주식회사 | 결정성 클로피도그렐 · 황산염 형태 ｉ의 제조방법 |
| US7935697B2 (en) | 2006-12-28 | 2011-05-03 | Kinex Pharmaceuticals, Llc | Compositions for modulating a kinase cascade and methods of use thereof |
| KR100805675B1 (ko) | 2007-03-07 | 2008-02-21 | 한림제약(주) | 클로피도그렐 베실레이트를 포함하는 약학 조성물 및 그의제조방법 |
| EP2062909A1 (en) * | 2007-11-21 | 2009-05-27 | SOLVAY (Société Anonyme) | Peptide production and purification process |
| KR100920932B1 (ko) * | 2007-12-05 | 2009-10-20 | 한림제약(주) | 결정형의 클로피도그렐 벤젠술폰산염의 제조방법 |
| EP2107061A1 (en) | 2008-04-02 | 2009-10-07 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of optically enriched clopidogrel |
| WO2012123958A1 (en) | 2011-02-14 | 2012-09-20 | Cadila Healthcare Limited | Highly pure salts of clopidogrel free of genotoxic impurities |
| CN102285996A (zh) * | 2011-03-30 | 2011-12-21 | 天津红日药业股份有限公司 | 一种苯磺酸氯吡格雷晶型ⅱ及其制备方法和用途 |
| CN102199161B (zh) * | 2011-03-30 | 2013-07-03 | 天津红日药业股份有限公司 | 一种苯磺酸氯吡格雷晶型ⅰ及其制备方法和用途 |
| CN104193762B (zh) * | 2014-08-04 | 2017-02-15 | 浙江车头制药股份有限公司 | 一种制备苯磺酸氯吡格雷晶型ⅲ的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2530247B1 (fr) | 1982-07-13 | 1986-05-16 | Sanofi Sa | Nouveaux derives de la thieno (3, 2-c) pyridine, leur procede de preparation et leur application therapeutique |
| GB8608335D0 (en) | 1986-04-04 | 1986-05-08 | Pfizer Ltd | Pharmaceutically acceptable salts |
| FR2623810B2 (fr) | 1987-02-17 | 1992-01-24 | Sanofi Sa | Sels de l'alpha-(tetrahydro-4,5,6,7 thieno(3,2-c) pyridyl-5) (chloro-2 phenyl) -acetate de methyle dextrogyre et compositions pharmaceutiques en contenant |
| FR2779726B1 (fr) * | 1998-06-15 | 2001-05-18 | Sanofi Sa | Forme polymorphe de l'hydrogenosulfate de clopidogrel |
| US6509348B1 (en) | 1998-11-03 | 2003-01-21 | Bristol-Myers Squibb Company | Combination of an ADP-receptor blocking antiplatelet drug and a thromboxane A2 receptor antagonist and a method for inhibiting thrombus formation employing such combination |
| DE19857137A1 (de) | 1998-12-11 | 2000-06-15 | Bayer Ag | Integriertes Verfahren zur Herstellung von Epoxiden aus Olefinen |
| IN191030B (da) | 2001-01-24 | 2003-09-13 | Cadila Healthcare Ltd | |
| US6767913B2 (en) | 2001-12-18 | 2004-07-27 | Teva Pharmaceutical Industries Ltd. | Crystal forms iii, iv, v, and novel amorphous form of clopidogrel hydrogensulfate, processes for their preparation, processes for the preparation of form i, compositions containing the new forms and methods of administering the new forms |
| IL166593A0 (en) | 2002-08-02 | 2006-01-15 | Racemization and enantiomer separation of clopidogrel | |
| EP1606231A1 (en) * | 2003-02-03 | 2005-12-21 | Nadkarni, Sunil Sadanand | Process for preparation of clopidogrel, its salts and pharmaceutical compositions |
| DE10305984A1 (de) | 2003-02-13 | 2004-09-02 | Helm Ag | Salze organischer Säuren mit Clopidogrel und deren Verwendung zur Herstellung phamazeutischer Formulierungen |
| AU2003238664A1 (en) | 2003-03-12 | 2004-09-30 | Cadila Healthcare Limited | Polymorphs and amorphous form of (s) - (+) -clopidogrel bisulfate |
| ES2531088T3 (es) | 2003-04-25 | 2015-03-10 | Cadila Healthcare Ltd | Sales de clopidogrel y procedimiento de preparación |
| ATE455778T1 (de) | 2003-11-03 | 2010-02-15 | Cadila Healthcare Ltd | Verfahren zur herstellung form i von (s)-(+)- clopidogrelbisulfat |
| EP1900358A1 (en) | 2006-09-16 | 2008-03-19 | Cimex Pharma AG | Pharmaceutical formulations comprising clopidogrel |
-
2004
- 2004-04-22 ES ES04770646T patent/ES2531088T3/es not_active Expired - Lifetime
- 2004-04-22 WO PCT/IN2004/000112 patent/WO2004106344A2/en not_active Ceased
- 2004-04-22 KR KR1020057020142A patent/KR20060013376A/ko not_active Ceased
- 2004-04-22 SI SI200432209T patent/SI1618111T1/sl unknown
- 2004-04-22 PL PL04770646T patent/PL1618111T3/pl unknown
- 2004-04-22 DK DK04770646.0T patent/DK1618111T3/da active
- 2004-04-22 EP EP09010218A patent/EP2113506A3/en not_active Withdrawn
- 2004-04-22 US US10/554,367 patent/US7732608B2/en not_active Expired - Fee Related
- 2004-04-22 EP EP14192561.0A patent/EP2865681A3/en not_active Withdrawn
- 2004-04-22 PT PT47706460T patent/PT1618111E/pt unknown
- 2004-04-22 EP EP08001523A patent/EP1927595B1/en not_active Expired - Lifetime
- 2004-04-22 EP EP04770646.0A patent/EP1618111B1/en not_active Expired - Lifetime
- 2004-04-22 DE DE4770646T patent/DE04770646T1/de active Pending
- 2004-04-22 HR HRP20150056TT patent/HRP20150056T1/hr unknown
-
2005
- 2005-10-17 NO NO20054763A patent/NO333586B1/no not_active IP Right Cessation
-
2010
- 2010-04-14 US US12/760,523 patent/US8053579B2/en not_active Expired - Fee Related
-
2015
- 2015-02-17 CY CY20151100161T patent/CY1116554T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060013376A (ko) | 2006-02-09 |
| NO20054763L (no) | 2006-01-16 |
| US20100197923A1 (en) | 2010-08-05 |
| SI1618111T1 (sl) | 2015-05-29 |
| EP1927595A2 (en) | 2008-06-04 |
| ES2531088T3 (es) | 2015-03-10 |
| EP2865681A2 (en) | 2015-04-29 |
| PT1618111E (pt) | 2015-02-05 |
| WO2004106344A3 (en) | 2005-03-24 |
| US20060264636A1 (en) | 2006-11-23 |
| EP1927595A3 (en) | 2008-09-24 |
| CY1116554T1 (el) | 2017-03-15 |
| NO333586B1 (no) | 2013-07-15 |
| WO2004106344A2 (en) | 2004-12-09 |
| HRP20150056T1 (hr) | 2015-04-24 |
| NO20054763D0 (no) | 2005-10-17 |
| EP2113506A2 (en) | 2009-11-04 |
| EP1618111B1 (en) | 2014-12-24 |
| EP1618111A2 (en) | 2006-01-25 |
| EP2113506A3 (en) | 2010-02-24 |
| US8053579B2 (en) | 2011-11-08 |
| DE04770646T1 (de) | 2011-12-08 |
| EP1927595B1 (en) | 2013-03-06 |
| PL1618111T3 (pl) | 2015-06-30 |
| EP2865681A3 (en) | 2015-08-19 |
| US7732608B2 (en) | 2010-06-08 |
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