NO312193B1 - Fremgangsmåte for fremstilling av optisk vesentlig rene enantiomerer av et pyridazinonderivat, fremgangsmåte for denoptiske opplösningen av et pyridazinonderovat, krystallinskpolymorf form av et pyridazinonderivat og en fremgangsmåte foroppnå - Google Patents
Fremgangsmåte for fremstilling av optisk vesentlig rene enantiomerer av et pyridazinonderivat, fremgangsmåte for denoptiske opplösningen av et pyridazinonderovat, krystallinskpolymorf form av et pyridazinonderivat og en fremgangsmåte foroppnå Download PDFInfo
- Publication number
- NO312193B1 NO312193B1 NO19984487A NO984487A NO312193B1 NO 312193 B1 NO312193 B1 NO 312193B1 NO 19984487 A NO19984487 A NO 19984487A NO 984487 A NO984487 A NO 984487A NO 312193 B1 NO312193 B1 NO 312193B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- tetrahydro
- oxo
- phenyl
- hydrazono
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000003287 optical effect Effects 0.000 title claims description 10
- 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 title description 25
- 238000002360 preparation method Methods 0.000 title description 4
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title 3
- WHXMKTBCFHIYNQ-UHFFFAOYSA-N 2-[[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]hydrazinylidene]propanedinitrile Chemical compound CC1CC(=O)NN=C1C1=CC=C(NN=C(C#N)C#N)C=C1 WHXMKTBCFHIYNQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 38
- GDMRFHZLKNYRRO-UHFFFAOYSA-N 3-(4-aminophenyl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N)C=C1 GDMRFHZLKNYRRO-UHFFFAOYSA-N 0.000 claims description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- 239000002244 precipitate Substances 0.000 claims description 25
- 239000000047 product Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 17
- 238000004090 dissolution Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 9
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 9
- 125000005638 hydrazono group Chemical group 0.000 claims description 8
- 239000012452 mother liquor Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
- 229940011051 isopropyl acetate Drugs 0.000 claims description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
- WHXMKTBCFHIYNQ-SECBINFHSA-N levosimendan Chemical compound C[C@@H]1CC(=O)NN=C1C1=CC=C(NN=C(C#N)C#N)C=C1 WHXMKTBCFHIYNQ-SECBINFHSA-N 0.000 claims description 3
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- -1 oxo-3-pyridazinyl Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 239000000496 cardiotonic agent Substances 0.000 abstract 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229960001270 d- tartaric acid Drugs 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GAWAYYRQGQZKCR-UWTATZPHSA-N (2r)-2-chloropropanoic acid Chemical compound C[C@@H](Cl)C(O)=O GAWAYYRQGQZKCR-UWTATZPHSA-N 0.000 description 1
- JJNZXLAFIPKXIG-UHFFFAOYSA-N 2-Chlorobenzylidenemalononitrile Chemical compound ClC1=CC=CC=C1C=C(C#N)C#N JJNZXLAFIPKXIG-UHFFFAOYSA-N 0.000 description 1
- VKIGAWAEXPTIOL-UHFFFAOYSA-N 2-hydroxyhexanenitrile Chemical compound CCCCC(O)C#N VKIGAWAEXPTIOL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- JMCFZKWHGZNZFS-UHFFFAOYSA-N N-[4-(4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl)anilino]ethanimidoyl cyanide Chemical compound CC1C(=NNC(C1)=O)C1=CC=C(C=C1)NN=C(C#N)C JMCFZKWHGZNZFS-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9606474.6A GB9606474D0 (en) | 1996-03-27 | 1996-03-27 | Method for obtaining pure enantiomers of a pyridazinone derivative |
| PCT/FI1997/000196 WO1997035841A2 (fr) | 1996-03-27 | 1997-03-27 | Procede d'obtention d'enantiomeres purs d'un derive de pyridazinone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO984487D0 NO984487D0 (no) | 1998-09-25 |
| NO984487L NO984487L (no) | 1998-11-26 |
| NO312193B1 true NO312193B1 (no) | 2002-04-08 |
Family
ID=10791141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19984487A NO312193B1 (no) | 1996-03-27 | 1998-09-25 | Fremgangsmåte for fremstilling av optisk vesentlig rene enantiomerer av et pyridazinonderivat, fremgangsmåte for denoptiske opplösningen av et pyridazinonderovat, krystallinskpolymorf form av et pyridazinonderivat og en fremgangsmåte foroppnå |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6180789B1 (fr) |
| EP (3) | EP0894087B1 (fr) |
| JP (3) | JP4179630B2 (fr) |
| AT (3) | ATE525361T1 (fr) |
| AU (1) | AU715887B2 (fr) |
| BR (1) | BR9708353A (fr) |
| CA (1) | CA2250062C (fr) |
| CZ (3) | CZ294964B6 (fr) |
| DE (2) | DE69733748T2 (fr) |
| DK (2) | DK0894087T3 (fr) |
| ES (3) | ES2370760T3 (fr) |
| GB (1) | GB9606474D0 (fr) |
| HU (1) | HU227541B1 (fr) |
| MX (1) | MXPA98007851A (fr) |
| NO (1) | NO312193B1 (fr) |
| NZ (1) | NZ332010A (fr) |
| PL (3) | PL189963B1 (fr) |
| PT (3) | PT894087E (fr) |
| SI (2) | SI2143715T1 (fr) |
| SK (3) | SK285364B6 (fr) |
| TR (1) | TR199801921T2 (fr) |
| WO (1) | WO1997035841A2 (fr) |
| ZA (1) | ZA972729B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9606474D0 (en) * | 1996-03-27 | 1996-06-05 | Orion Yhytmo Oy | Method for obtaining pure enantiomers of a pyridazinone derivative |
| FI973804A (fi) * | 1997-09-26 | 1999-03-27 | Orion Yhtymae Oy | Levosimendaanin oraalisia koostumuksia |
| FI105389B (fi) * | 1998-04-23 | 2000-08-15 | Orion Yhtymae Oyj | Menetelmä levosimendaaniannon siedettävyyden seuraamiseksi |
| FI104718B (fi) * | 1998-06-18 | 2000-03-31 | Orion Yhtymae Oyj | [[4-(2-atsido-3-metyyli-5-oksotetrahydrofuran-2-yyli)fenyyli]hydratsono]propaanidinitriili käytettäväksi referenssiaineena levosimendaanierien analyysissä |
| US5905078A (en) * | 1998-06-19 | 1999-05-18 | Orion Corporation | Use of a pyridazinone derivative |
| FI109659B (fi) | 1999-09-10 | 2002-09-30 | Orion Yhtymae Oyj | Levosimendaanin farmaseuttisia liuoksia |
| WO2008019055A2 (fr) * | 2006-08-03 | 2008-02-14 | Teva Pharmaceutical Industries Ltd. | Procédé de dédoublement optique de 1-phényl-1,2,3,4-tétrahydroisoquinoléine |
| US9000158B2 (en) | 2009-07-14 | 2015-04-07 | Cipla Limited | Process for preparing levosimendan and intermediates for use in the process |
| JP5482926B2 (ja) * | 2011-02-28 | 2014-05-07 | 株式会社リコー | 伝送管理装置 |
| CN103554033A (zh) * | 2013-11-12 | 2014-02-05 | 江苏正大清江制药有限公司 | 一种消旋体(±)- 6-(4-氨基苯基)-4,5-二氢-5-甲基-3(2h)-哒嗪酮的拆分方法 |
| CN103554032A (zh) * | 2013-11-12 | 2014-02-05 | 江苏正大清江制药有限公司 | 高光学纯度(-)-6-(4-氨基苯基)-4,5-二氢-5-甲基-3(2h)-哒嗪酮的制备方法 |
| ITMI20132185A1 (it) * | 2013-12-23 | 2015-06-24 | Edmond Pharma Srl | Polimorfi di levosimendan |
| EP3424908A1 (fr) * | 2017-07-07 | 2019-01-09 | Melody Healthcare Pvt. Ltd. | Procédé de préparation de levosimendan |
| US11760730B2 (en) * | 2021-01-11 | 2023-09-19 | Navinta, Llc | Process for the preparation of high purity Levosimendan |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1211589A (en) * | 1968-08-06 | 1970-11-11 | Ici Ltd | Enantiomer isolation process |
| US4946842A (en) | 1985-07-05 | 1990-08-07 | Smith Kline & French Laboratories Limited | Novel guanidino pyridazinones as cardiac stimulants |
| GB8903130D0 (en) * | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
| GB2251615B (en) * | 1991-01-03 | 1995-02-08 | Orion Yhtymae Oy | (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]pro panedinitrile |
| GB9606474D0 (en) * | 1996-03-27 | 1996-06-05 | Orion Yhytmo Oy | Method for obtaining pure enantiomers of a pyridazinone derivative |
| FI973804A (fi) * | 1997-09-26 | 1999-03-27 | Orion Yhtymae Oy | Levosimendaanin oraalisia koostumuksia |
-
1996
- 1996-03-27 GB GBGB9606474.6A patent/GB9606474D0/en active Pending
-
1997
- 1997-03-27 ES ES09013140T patent/ES2370760T3/es not_active Expired - Lifetime
- 1997-03-27 EP EP97914347A patent/EP0894087B1/fr not_active Expired - Lifetime
- 1997-03-27 ES ES97914347T patent/ES2243988T3/es not_active Expired - Lifetime
- 1997-03-27 CZ CZ19983041A patent/CZ294964B6/cs not_active IP Right Cessation
- 1997-03-27 SK SK5004-2006A patent/SK285364B6/sk not_active IP Right Cessation
- 1997-03-27 ES ES05010245T patent/ES2343525T3/es not_active Expired - Lifetime
- 1997-03-27 TR TR1998/01921T patent/TR199801921T2/xx unknown
- 1997-03-27 AT AT09013140T patent/ATE525361T1/de active
- 1997-03-27 EP EP09013140A patent/EP2143715B1/fr not_active Expired - Lifetime
- 1997-03-27 CA CA002250062A patent/CA2250062C/fr not_active Expired - Lifetime
- 1997-03-27 AT AT05010245T patent/ATE465154T1/de not_active IP Right Cessation
- 1997-03-27 CZ CZ20021282A patent/CZ295001B6/cs not_active IP Right Cessation
- 1997-03-27 JP JP53406397A patent/JP4179630B2/ja not_active Expired - Lifetime
- 1997-03-27 DE DE69733748T patent/DE69733748T2/de not_active Expired - Lifetime
- 1997-03-27 DK DK97914347T patent/DK0894087T3/da active
- 1997-03-27 SI SI9730798T patent/SI2143715T1/sl unknown
- 1997-03-27 EP EP05010245A patent/EP1619186B1/fr not_active Expired - Lifetime
- 1997-03-27 PT PT97914347T patent/PT894087E/pt unknown
- 1997-03-27 ZA ZA9702729A patent/ZA972729B/xx unknown
- 1997-03-27 MX MXPA98007851A patent/MXPA98007851A/es active IP Right Grant
- 1997-03-27 DK DK09013140.0T patent/DK2143715T3/da active
- 1997-03-27 WO PCT/FI1997/000196 patent/WO1997035841A2/fr active Application Filing
- 1997-03-27 SI SI9730713T patent/SI0894087T1/xx unknown
- 1997-03-27 US US09/155,294 patent/US6180789B1/en not_active Expired - Lifetime
- 1997-03-27 AU AU21626/97A patent/AU715887B2/en not_active Expired
- 1997-03-27 BR BR9708353A patent/BR9708353A/pt not_active IP Right Cessation
- 1997-03-27 PL PL97329068A patent/PL189963B1/pl unknown
- 1997-03-27 PT PT05010245T patent/PT1619186E/pt unknown
- 1997-03-27 CZ CZ20021283A patent/CZ295002B6/cs not_active IP Right Cessation
- 1997-03-27 NZ NZ332010A patent/NZ332010A/en not_active IP Right Cessation
- 1997-03-27 HU HU9904150A patent/HU227541B1/hu unknown
- 1997-03-27 SK SK5035-2005A patent/SK285363B6/sk not_active IP Right Cessation
- 1997-03-27 PL PL97364219A patent/PL190573B1/pl unknown
- 1997-03-27 AT AT97914347T patent/ATE299867T1/de active
- 1997-03-27 DE DE69739858T patent/DE69739858D1/de not_active Expired - Lifetime
- 1997-03-27 SK SK1316-98A patent/SK285362B6/sk not_active IP Right Cessation
- 1997-03-27 PL PL97364220A patent/PL190574B1/pl unknown
- 1997-03-27 PT PT09013140T patent/PT2143715E/pt unknown
-
1998
- 1998-09-25 NO NO19984487A patent/NO312193B1/no not_active IP Right Cessation
-
2008
- 2008-02-15 JP JP2008034860A patent/JP4825825B2/ja not_active Expired - Lifetime
-
2011
- 2011-08-18 JP JP2011179148A patent/JP5277295B2/ja not_active Expired - Lifetime
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| Date | Code | Title | Description |
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| MK1K | Patent expired |