NO333586B1 - Krystallinsk clopidogrel og fremgangsmate for fremstilling derav - Google Patents
Krystallinsk clopidogrel og fremgangsmate for fremstilling derav Download PDFInfo
- Publication number
- NO333586B1 NO333586B1 NO20054763A NO20054763A NO333586B1 NO 333586 B1 NO333586 B1 NO 333586B1 NO 20054763 A NO20054763 A NO 20054763A NO 20054763 A NO20054763 A NO 20054763A NO 333586 B1 NO333586 B1 NO 333586B1
- Authority
- NO
- Norway
- Prior art keywords
- clopidogrel
- butyl
- besylate
- solvents
- clopidogrel besylate
- Prior art date
Links
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 title claims abstract description 69
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 title claims abstract description 32
- 229960003009 clopidogrel Drugs 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 229950010557 clopidogrel besilate Drugs 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 9
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- 238000001757 thermogravimetry curve Methods 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 229940127218 antiplatelet drug Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007787 solid Substances 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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- FDEODCTUSIWGLK-RSAXXLAASA-N clopidogrel sulfate Chemical compound [H+].OS([O-])(=O)=O.C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl FDEODCTUSIWGLK-RSAXXLAASA-N 0.000 description 2
- 239000002552 dosage form Substances 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
- -1 t- butyl Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical class OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 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
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 229940124345 antianginal agent Drugs 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 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
- 229940049636 dobesilic acid Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000000694 effects Effects 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
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229940020573 plavix Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 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)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN413MU2003 | 2003-04-25 | ||
| PCT/IN2004/000112 WO2004106344A2 (fr) | 2003-04-25 | 2004-04-22 | Sels de clopidogrel et procede de preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20054763D0 NO20054763D0 (no) | 2005-10-17 |
| NO20054763L NO20054763L (no) | 2006-01-16 |
| NO333586B1 true NO333586B1 (no) | 2013-07-15 |
Family
ID=33485475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20054763A NO333586B1 (no) | 2003-04-25 | 2005-10-17 | Krystallinsk clopidogrel og fremgangsmate for fremstilling derav |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7732608B2 (fr) |
| EP (4) | EP1618111B1 (fr) |
| KR (1) | KR20060013376A (fr) |
| CY (1) | CY1116554T1 (fr) |
| DE (1) | DE04770646T1 (fr) |
| DK (1) | DK1618111T3 (fr) |
| ES (1) | ES2531088T3 (fr) |
| HR (1) | HRP20150056T1 (fr) |
| NO (1) | NO333586B1 (fr) |
| PL (1) | PL1618111T3 (fr) |
| PT (1) | PT1618111E (fr) |
| SI (1) | SI1618111T1 (fr) |
| WO (1) | WO2004106344A2 (fr) |
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 |
| EP1603920A1 (fr) * | 2003-03-12 | 2005-12-14 | Cadila Healthcare Ltd. | Polymorphes et forme amorphe de bisulfate de (s) - (+) -clopidogrel |
| EP1618111B1 (fr) * | 2003-04-25 | 2014-12-24 | Cadila Healthcare Limited | Sels de clopidogrel et procede de preparation |
| US8907090B2 (en) * | 2003-11-03 | 2014-12-09 | Cadila Healthcare Limited | Processes for preparing different forms of (S)-(+)-Clopidogrel bisulfate |
| WO2005080890A1 (fr) * | 2004-02-24 | 2005-09-01 | Siegfried Generics International Ag | Sels de clopidogrel acceptables d'un point de vue pharmacologique |
| ZA200608035B (en) * | 2004-04-20 | 2008-07-30 | Sanofi Aventis | Clopidogrel salt and polymorphic forms thereof |
| WO2006074066A1 (fr) * | 2004-12-30 | 2006-07-13 | Nektar Therapeutics | Formulation non cristalline comprenant du clopidogrel |
| EP1934229B1 (fr) | 2005-09-05 | 2012-09-26 | Cadila Healthcare Limited | Procedes de preparation de differentes formes de (s)-(+)-clopidogrel besylate |
| 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 (fr) * | 2007-11-21 | 2009-05-27 | SOLVAY (Société Anonyme) | Production de peptides et procédé de purification |
| KR100920932B1 (ko) * | 2007-12-05 | 2009-10-20 | 한림제약(주) | 결정형의 클로피도그렐 벤젠술폰산염의 제조방법 |
| EP2107061A1 (fr) | 2008-04-02 | 2009-10-07 | Krka Tovarna Zdravil, D.D., Novo Mesto | Procédé de préparation de clopidogrel enrichi optiquement |
| WO2012123958A1 (fr) | 2011-02-14 | 2012-09-20 | Cadila Healthcare Limited | Sels très purs de clopidogrel exempts d'impuretés génotoxiques |
| 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 |
| 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 |
| 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 (fr) | 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 (fr) * | 2003-02-03 | 2005-12-21 | Nadkarni, Sunil Sadanand | Procede de preparation de clopidogrel, ses sels et compositions pharmaceutiques |
| DE10305984A1 (de) | 2003-02-13 | 2004-09-02 | Helm Ag | Salze organischer Säuren mit Clopidogrel und deren Verwendung zur Herstellung phamazeutischer Formulierungen |
| EP1603920A1 (fr) * | 2003-03-12 | 2005-12-14 | Cadila Healthcare Ltd. | Polymorphes et forme amorphe de bisulfate de (s) - (+) -clopidogrel |
| EP1618111B1 (fr) | 2003-04-25 | 2014-12-24 | Cadila Healthcare Limited | Sels de clopidogrel et procede de preparation |
| US8907090B2 (en) * | 2003-11-03 | 2014-12-09 | Cadila Healthcare Limited | Processes for preparing different forms of (S)-(+)-Clopidogrel bisulfate |
| EP1900358A1 (fr) | 2006-09-16 | 2008-03-19 | Cimex Pharma AG | Formulations pharmaceutiques contenant du clopidogrel |
-
2004
- 2004-04-22 EP EP04770646.0A patent/EP1618111B1/fr not_active Expired - Lifetime
- 2004-04-22 WO PCT/IN2004/000112 patent/WO2004106344A2/fr active Application Filing
- 2004-04-22 PT PT47706460T patent/PT1618111E/pt unknown
- 2004-04-22 KR KR1020057020142A patent/KR20060013376A/ko not_active Application Discontinuation
- 2004-04-22 PL PL04770646T patent/PL1618111T3/pl unknown
- 2004-04-22 EP EP09010218A patent/EP2113506A3/fr not_active Withdrawn
- 2004-04-22 ES ES04770646T patent/ES2531088T3/es not_active Expired - Lifetime
- 2004-04-22 EP EP14192561.0A patent/EP2865681A3/fr not_active Withdrawn
- 2004-04-22 EP EP08001523A patent/EP1927595B1/fr not_active Expired - Lifetime
- 2004-04-22 DK DK04770646.0T patent/DK1618111T3/en active
- 2004-04-22 DE DE4770646T patent/DE04770646T1/de active Pending
- 2004-04-22 US US10/554,367 patent/US7732608B2/en not_active Expired - Fee Related
- 2004-04-22 SI SI200432209T patent/SI1618111T1/sl 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
- 2015-01-16 HR HRP20150056TT patent/HRP20150056T1/hr unknown
- 2015-02-17 CY CY20151100161T patent/CY1116554T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2113506A2 (fr) | 2009-11-04 |
| US8053579B2 (en) | 2011-11-08 |
| PL1618111T3 (pl) | 2015-06-30 |
| WO2004106344A2 (fr) | 2004-12-09 |
| PT1618111E (pt) | 2015-02-05 |
| DK1618111T3 (en) | 2015-02-16 |
| NO20054763D0 (no) | 2005-10-17 |
| US20100197923A1 (en) | 2010-08-05 |
| DE04770646T1 (de) | 2011-12-08 |
| EP1927595A3 (fr) | 2008-09-24 |
| EP2113506A3 (fr) | 2010-02-24 |
| WO2004106344A3 (fr) | 2005-03-24 |
| EP2865681A3 (fr) | 2015-08-19 |
| EP1927595A2 (fr) | 2008-06-04 |
| US7732608B2 (en) | 2010-06-08 |
| EP1618111B1 (fr) | 2014-12-24 |
| EP2865681A2 (fr) | 2015-04-29 |
| HRP20150056T1 (hr) | 2015-04-24 |
| CY1116554T1 (el) | 2017-03-15 |
| KR20060013376A (ko) | 2006-02-09 |
| SI1618111T1 (sl) | 2015-05-29 |
| EP1927595B1 (fr) | 2013-03-06 |
| ES2531088T3 (es) | 2015-03-10 |
| US20060264636A1 (en) | 2006-11-23 |
| NO20054763L (no) | 2006-01-16 |
| EP1618111A2 (fr) | 2006-01-25 |
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