SK285715B6 - Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom - Google Patents
Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom Download PDFInfo
- Publication number
- SK285715B6 SK285715B6 SK566-2003A SK5662003A SK285715B6 SK 285715 B6 SK285715 B6 SK 285715B6 SK 5662003 A SK5662003 A SK 5662003A SK 285715 B6 SK285715 B6 SK 285715B6
- Authority
- SK
- Slovakia
- Prior art keywords
- desloratadine
- formula
- synthesis
- hemisulphate
- salts
- Prior art date
Links
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical class C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 title claims description 7
- 238000003786 synthesis reaction Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 229960001271 desloratadine Drugs 0.000 claims abstract description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 8
- 230000003266 anti-allergic effect Effects 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 16
- 229960003088 loratadine Drugs 0.000 claims description 15
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- BFUKZAZVGNXTDM-UHFFFAOYSA-N 8-chloro-11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1.C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 BFUKZAZVGNXTDM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000007864 aqueous solution Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 11
- 238000002360 preparation method Methods 0.000 abstract description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 238000000265 homogenisation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
- -1 bisulfate anions Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0004701A HU226998B1 (en) | 2000-11-23 | 2000-11-23 | Desloratadine hemisulphate, process for the preparation thereof and pharmaceutical compositions containing the same |
| PCT/HU2001/000111 WO2002042290A1 (en) | 2000-11-23 | 2001-11-14 | New desloratadine salts, process for their synthesis and pharmaceutical compositions thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK5662003A3 SK5662003A3 (en) | 2003-10-07 |
| SK285715B6 true SK285715B6 (sk) | 2007-06-07 |
Family
ID=89978790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK566-2003A SK285715B6 (sk) | 2000-11-23 | 2001-11-14 | Soli desloratadínu, spôsob ich prípravy a farmaceutické prípravky s ich obsahom |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7196195B2 (cs) |
| EP (1) | EP1347965B1 (cs) |
| JP (1) | JP4427249B2 (cs) |
| CN (1) | CN1199968C (cs) |
| AT (1) | ATE316525T1 (cs) |
| AU (1) | AU2002218422A1 (cs) |
| CA (1) | CA2425422C (cs) |
| CY (1) | CY1105595T1 (cs) |
| CZ (1) | CZ304694B6 (cs) |
| DE (1) | DE60116902T2 (cs) |
| DK (1) | DK1347965T3 (cs) |
| ES (1) | ES2257467T3 (cs) |
| HU (1) | HU226998B1 (cs) |
| NO (1) | NO325155B1 (cs) |
| PL (1) | PL206973B1 (cs) |
| RU (1) | RU2285001C2 (cs) |
| SK (1) | SK285715B6 (cs) |
| UA (1) | UA74858C2 (cs) |
| WO (1) | WO2002042290A1 (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7678908B2 (en) | 2002-04-15 | 2010-03-16 | Sun Pharmaceutical Industries Limited | Process of preparing desaloratadine |
| KR20050069976A (ko) * | 2002-08-05 | 2005-07-05 | 산도즈 아게 | 데스로라타딘 헤미푸마레이트의 신규 염 및 다형체 |
| JP4501015B2 (ja) | 2004-03-17 | 2010-07-14 | 味の素株式会社 | アミノピリミジン化合物の製造方法 |
| RS20070008A (en) * | 2004-07-07 | 2008-11-28 | Egis Gyogyszergyar Rt., | New pseudopolymorph of desloratidine formed with carbon dioxide |
| CA2541045A1 (en) * | 2006-03-24 | 2007-09-24 | Pharmascience Inc. | A descarbonylethoxyloratadine containing pharmaceutical composition |
| EP2837631A1 (en) * | 2013-08-14 | 2015-02-18 | Merck & Cie | New stable salt of 5,10-methylene-(6R)-tetrahydrofolic acid |
| WO2021086133A1 (ko) * | 2019-10-31 | 2021-05-06 | (주)제이디바이오사이언스 | 삼환식 화합물 및 이의 약학적 용도 |
| CN115785065A (zh) * | 2022-12-02 | 2023-03-14 | 山东达因海洋生物制药股份有限公司 | 一种地氯雷他定共晶及其制备方法与应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282233B1 (en) * | 1980-06-19 | 2000-09-05 | Schering Corp | Antihistaminic 11-(4-piperidylidene)-5h-benzoÄ5,6Ü-cyclohepta-Ä1,2Ü-pyridines |
| WO1985003707A1 (en) * | 1984-02-15 | 1985-08-29 | Schering Corporation | 8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDYLIDENE)-5H-BENZO AD5,6 BDCYCLOHEPTA AD1,2-b BDPYRIDINE AND ITS SALTS, PROCESSES FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS |
| DE3677842D1 (de) * | 1985-05-13 | 1991-04-11 | Schering Corp | Verfahren zur herstellung von piperidyliden-dihydrodibenzo(a,d)zykloheptenen und deren azoderivate, so hergestellte verbindungen und ihre anwendung zur vorbereitung von heilmitteln. |
| DK0656348T3 (da) * | 1993-12-03 | 2000-09-11 | Hoffmann La Roche | Eddikesyrederivater som medikamenter |
| GB9709945D0 (en) * | 1997-05-17 | 1997-07-09 | Glaxo Group Ltd | A novel salt |
| WO2001045676A2 (en) * | 1999-12-20 | 2001-06-28 | Schering Corporation | Extended release oral dosage composition |
| RU2164796C1 (ru) * | 2000-05-25 | 2001-04-10 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Противогистаминное средство и способ его получения |
-
2000
- 2000-11-23 HU HU0004701A patent/HU226998B1/hu unknown
-
2001
- 2001-11-14 US US10/432,387 patent/US7196195B2/en not_active Expired - Lifetime
- 2001-11-14 SK SK566-2003A patent/SK285715B6/sk not_active IP Right Cessation
- 2001-11-14 UA UA2003065756A patent/UA74858C2/uk unknown
- 2001-11-14 PL PL362126A patent/PL206973B1/pl unknown
- 2001-11-14 CZ CZ2003-1321A patent/CZ304694B6/cs unknown
- 2001-11-14 WO PCT/HU2001/000111 patent/WO2002042290A1/en active IP Right Grant
- 2001-11-14 RU RU2003118425/04A patent/RU2285001C2/ru active
- 2001-11-14 EP EP01997485A patent/EP1347965B1/en not_active Expired - Lifetime
- 2001-11-14 JP JP2002544424A patent/JP4427249B2/ja not_active Expired - Lifetime
- 2001-11-14 DE DE60116902T patent/DE60116902T2/de not_active Expired - Lifetime
- 2001-11-14 CA CA002425422A patent/CA2425422C/en not_active Expired - Lifetime
- 2001-11-14 ES ES01997485T patent/ES2257467T3/es not_active Expired - Lifetime
- 2001-11-14 AU AU2002218422A patent/AU2002218422A1/en not_active Abandoned
- 2001-11-14 CN CNB018193382A patent/CN1199968C/zh not_active Expired - Lifetime
- 2001-11-14 AT AT01997485T patent/ATE316525T1/de active
- 2001-11-14 DK DK01997485T patent/DK1347965T3/da active
-
2003
- 2003-05-22 NO NO20032314A patent/NO325155B1/no not_active IP Right Cessation
-
2006
- 2006-03-29 CY CY20061100435T patent/CY1105595T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1347965B1 (en) | 2006-01-25 |
| CA2425422A1 (en) | 2002-05-30 |
| DK1347965T3 (da) | 2006-06-06 |
| ES2257467T3 (es) | 2006-08-01 |
| NO20032314L (no) | 2003-07-18 |
| PL206973B1 (pl) | 2010-10-29 |
| SK5662003A3 (en) | 2003-10-07 |
| HU226998B1 (en) | 2010-04-28 |
| US7196195B2 (en) | 2007-03-27 |
| ATE316525T1 (de) | 2006-02-15 |
| CY1105595T1 (el) | 2010-07-28 |
| JP2004514675A (ja) | 2004-05-20 |
| EP1347965A1 (en) | 2003-10-01 |
| CN1199968C (zh) | 2005-05-04 |
| DE60116902T2 (de) | 2006-08-24 |
| CZ20031321A3 (cs) | 2003-08-13 |
| DE60116902D1 (de) | 2006-04-13 |
| HU0004701D0 (cs) | 2001-02-28 |
| JP4427249B2 (ja) | 2010-03-03 |
| CN1476443A (zh) | 2004-02-18 |
| HUP0004701A2 (hu) | 2002-11-28 |
| NO325155B1 (no) | 2008-02-11 |
| UA74858C2 (en) | 2006-02-15 |
| NO20032314D0 (no) | 2003-05-22 |
| RU2285001C2 (ru) | 2006-10-10 |
| AU2002218422A1 (en) | 2002-06-03 |
| WO2002042290A1 (en) | 2002-05-30 |
| CA2425422C (en) | 2009-11-10 |
| CZ304694B6 (cs) | 2014-09-03 |
| US20050203116A1 (en) | 2005-09-15 |
| PL362126A1 (en) | 2004-10-18 |
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| MK4A | Patent expired |
Expiry date: 20211114 |