NO313588B1 - Termodynamisk stabil modifikasjon av 1-(4-karbazolyloksy)-3- [2-(2-metoksyfenoksy)etylamino]-2-propanol, fremgangsmåte forfremstilling derav og farmasöytiske blandinger som inneholder den - Google Patents
Termodynamisk stabil modifikasjon av 1-(4-karbazolyloksy)-3- [2-(2-metoksyfenoksy)etylamino]-2-propanol, fremgangsmåte forfremstilling derav og farmasöytiske blandinger som inneholder den Download PDFInfo
- Publication number
- NO313588B1 NO313588B1 NO20000301A NO20000301A NO313588B1 NO 313588 B1 NO313588 B1 NO 313588B1 NO 20000301 A NO20000301 A NO 20000301A NO 20000301 A NO20000301 A NO 20000301A NO 313588 B1 NO313588 B1 NO 313588B1
- Authority
- NO
- Norway
- Prior art keywords
- carbazolyloxy
- ethylamino
- propanol
- carvedilol
- methoxyphenoxy
- Prior art date
Links
- OGHNVEJMJSYVRP-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000012986 modification Methods 0.000 title claims abstract description 12
- 230000004048 modification Effects 0.000 title claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 229960004195 carvedilol Drugs 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 238000002329 infrared spectrum Methods 0.000 claims description 4
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- 208000019622 heart disease Diseases 0.000 claims description 3
- 229910016523 CuKa Inorganic materials 0.000 claims description 2
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
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- 238000002955 isolation Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
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- 230000008707 rearrangement Effects 0.000 claims 1
- 238000006462 rearrangement reaction Methods 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
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- 201000010099 disease Diseases 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 150000001450 anions Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 229910052623 talc Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
- -1 gums Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 239000006210 lotion Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
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- 235000015424 sodium Nutrition 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97112491A EP0893440A1 (de) | 1997-07-22 | 1997-07-22 | Eine thermodynamisch stabile Modifikation von 1-(4-Carbazolyloxy)-3-[2-(2-methoxyphenoxy)ethylamino]- 2-propanole, Verfahren zu ihrer Herstellung und ihre enthaltende Arznemittel |
| PCT/EP1998/004475 WO1999005105A1 (en) | 1997-07-22 | 1998-07-18 | Thermodynamically stable modification of 1-(4-carbazolyloxy)-3-[2-(2-methoxyphenoxy)ethylamino]-2-propanole, process for its preparation and pharmaceutical compositions containing it |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20000301L NO20000301L (no) | 2000-01-21 |
| NO20000301D0 NO20000301D0 (no) | 2000-01-21 |
| NO313588B1 true NO313588B1 (no) | 2002-10-28 |
Family
ID=8227094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20000301A NO313588B1 (no) | 1997-07-22 | 2000-01-21 | Termodynamisk stabil modifikasjon av 1-(4-karbazolyloksy)-3- [2-(2-metoksyfenoksy)etylamino]-2-propanol, fremgangsmåte forfremstilling derav og farmasöytiske blandinger som inneholder den |
Country Status (32)
| Country | Link |
|---|---|
| EP (2) | EP0893440A1 (de) |
| JP (1) | JP2001510824A (de) |
| KR (1) | KR100336229B1 (de) |
| CN (1) | CN1125047C (de) |
| AR (1) | AR015133A1 (de) |
| AT (1) | ATE236123T1 (de) |
| AU (1) | AU740453B2 (de) |
| BR (1) | BR9810776A (de) |
| CA (1) | CA2296637C (de) |
| CZ (1) | CZ296947B6 (de) |
| DE (1) | DE69812964T2 (de) |
| DK (1) | DK1000027T3 (de) |
| ES (1) | ES2195366T3 (de) |
| HK (1) | HK1029339A1 (de) |
| HR (1) | HRP980406A2 (de) |
| HU (1) | HUP0003198A3 (de) |
| IL (1) | IL133677A (de) |
| MA (1) | MA26523A1 (de) |
| MY (1) | MY117734A (de) |
| NO (1) | NO313588B1 (de) |
| NZ (1) | NZ502136A (de) |
| PE (1) | PE96999A1 (de) |
| PL (1) | PL191602B1 (de) |
| PT (1) | PT1000027E (de) |
| RU (1) | RU2202542C2 (de) |
| SI (1) | SI1000027T1 (de) |
| TR (1) | TR200000148T2 (de) |
| TW (1) | TW505631B (de) |
| UY (1) | UY25108A1 (de) |
| WO (1) | WO1999005105A1 (de) |
| YU (1) | YU2200A (de) |
| ZA (1) | ZA986475B (de) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2227206T3 (es) * | 2000-04-03 | 2005-04-01 | F. Hoffmann-La Roche Ag | Soluciones concentradas de carvedilol. |
| MXPA02012795A (es) | 2000-06-28 | 2004-07-30 | Teva Pharma | Carvedilol. |
| EP1655285A1 (de) * | 2000-06-28 | 2006-05-10 | Teva Pharmaceutical Industries Ltd. | Verfahren zur Herstellung einer kristallinen Form von Carvedilol (Form II) |
| ATE328595T1 (de) * | 2001-07-13 | 2006-06-15 | Smithkline Beecham Corp | Carvedilolpolymorph |
| EP1929998A3 (de) | 2001-09-21 | 2008-11-26 | Egalet A/S | Festdispersionen mit gesteuerter Freisetzung von Carvedilol |
| ES2291503T3 (es) * | 2001-09-28 | 2008-03-01 | F. Hoffmann-La Roche Ag | Formas pseudopolimorficas de carvedilol. |
| MXPA04006909A (es) | 2002-01-15 | 2005-04-19 | Teva Pharma | Solidos cristalinos de carvedilol y procesos para su preparacion. |
| WO2003092622A2 (en) * | 2002-04-30 | 2003-11-13 | Sb Pharmco Puerto Rico Inc. | Carvedilol monocitrate monohydrate |
| EP1539140A4 (de) * | 2002-06-27 | 2005-12-07 | Sb Pharmco Inc | Carvedilolhydobromid |
| BR0312102A (pt) * | 2002-06-27 | 2007-05-29 | Sb Pharmco Inc | sais de fosfato de carvedilol e/ou seus solvatos, composições correspondentes, e/ou métodos de tratamento |
| EP1562552A1 (de) * | 2002-11-08 | 2005-08-17 | Egalet A/S | Zusammensetzung zur kontrollierten wirkstoffabgabe von carvedilol |
| EP1610767B1 (de) | 2003-03-26 | 2011-01-19 | Egalet A/S | Morphin-system mit kontrollierter freisetzung |
| WO2004094378A1 (en) * | 2003-04-21 | 2004-11-04 | Matrix Laboratories Ltd | Process for the preparation of carvedilol form-ii |
| SI21616A (sl) * | 2003-09-02 | 2005-04-30 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove kristalne oblike karvedilola |
| JP2007512372A (ja) * | 2003-11-25 | 2007-05-17 | エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド | カルベジロール塩、対応する組成物、送達および／または治療方法 |
| PT1838670E (pt) * | 2004-12-09 | 2009-12-18 | Zach System Spa | Processo para a preparação de carvedilol e seus enantiómeros |
| US20070043099A1 (en) * | 2005-06-09 | 2007-02-22 | Igor Lifshitz | Crystalline forms of carvedilol and processes for their preparation |
| US8022094B2 (en) | 2006-06-28 | 2011-09-20 | Teva Pharmaceutical Industries Ltd. | Carvedilol phosphate |
| US20080249317A1 (en) * | 2007-04-04 | 2008-10-09 | Apotex Inc. | Novel amorphous form of carvedilol phosphate and processes for the preparation thereof |
| EP2155167A2 (de) | 2007-06-04 | 2010-02-24 | Egalet A/S | Pharmazeutische zusammensetzungen mit gesteuerter freisetzung für verlängerte wirkung |
| NZ594207A (en) | 2009-02-06 | 2013-03-28 | Egalet Ltd | Immediate release composition resistant to abuse by intake of alcohol |
| AU2010265213B2 (en) | 2009-06-24 | 2012-08-23 | Egalet Ltd. | Controlled release formulations |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2815926A1 (de) * | 1978-04-13 | 1979-10-18 | Boehringer Mannheim Gmbh | Neue carbazolyl-(4)-oxy-propanolamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3319027A1 (de) * | 1983-05-26 | 1984-11-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur herstellung von optisch aktiven carbazol-derivaten, neue r- und s-carbazol-derivate, sowie arzneimittel, die diese verbindungen enthalten |
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1997
- 1997-07-22 EP EP97112491A patent/EP0893440A1/de not_active Withdrawn
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1998
- 1998-07-15 PE PE1998000626A patent/PE96999A1/es not_active Application Discontinuation
- 1998-07-15 MY MYPI98003245A patent/MY117734A/en unknown
- 1998-07-18 CZ CZ20000221A patent/CZ296947B6/cs not_active IP Right Cessation
- 1998-07-18 ES ES98937576T patent/ES2195366T3/es not_active Expired - Lifetime
- 1998-07-18 PT PT98937576T patent/PT1000027E/pt unknown
- 1998-07-18 WO PCT/EP1998/004475 patent/WO1999005105A1/en active IP Right Grant
- 1998-07-18 IL IL13367798A patent/IL133677A/en not_active IP Right Cessation
- 1998-07-18 TR TR2000/00148T patent/TR200000148T2/xx unknown
- 1998-07-18 CN CN98807436A patent/CN1125047C/zh not_active Expired - Fee Related
- 1998-07-18 DK DK98937576T patent/DK1000027T3/da active
- 1998-07-18 RU RU2000103033/04A patent/RU2202542C2/ru not_active IP Right Cessation
- 1998-07-18 PL PL338432A patent/PL191602B1/pl unknown
- 1998-07-18 AU AU86319/98A patent/AU740453B2/en not_active Ceased
- 1998-07-18 HU HU0003198A patent/HUP0003198A3/hu unknown
- 1998-07-18 AT AT98937576T patent/ATE236123T1/de not_active IP Right Cessation
- 1998-07-18 SI SI9830442T patent/SI1000027T1/xx unknown
- 1998-07-18 CA CA002296637A patent/CA2296637C/en not_active Expired - Fee Related
- 1998-07-18 BR BR9810776-3A patent/BR9810776A/pt not_active Application Discontinuation
- 1998-07-18 YU YU2200A patent/YU2200A/sh unknown
- 1998-07-18 NZ NZ502136A patent/NZ502136A/en unknown
- 1998-07-18 JP JP2000504104A patent/JP2001510824A/ja active Pending
- 1998-07-18 DE DE69812964T patent/DE69812964T2/de not_active Expired - Fee Related
- 1998-07-18 TW TW087111738A patent/TW505631B/zh not_active IP Right Cessation
- 1998-07-18 EP EP98937576A patent/EP1000027B1/de not_active Expired - Lifetime
- 1998-07-18 KR KR1020007000667A patent/KR100336229B1/ko not_active IP Right Cessation
- 1998-07-20 MA MA25178A patent/MA26523A1/fr unknown
- 1998-07-21 AR ARP980103547A patent/AR015133A1/es unknown
- 1998-07-21 ZA ZA9806475A patent/ZA986475B/xx unknown
- 1998-07-22 UY UY25108A patent/UY25108A1/es not_active IP Right Cessation
- 1998-07-22 HR HR97112491.2A patent/HRP980406A2/hr not_active Application Discontinuation
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2000
- 2000-01-21 NO NO20000301A patent/NO313588B1/no unknown
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2001
- 2001-01-02 HK HK01100012A patent/HK1029339A1/xx not_active IP Right Cessation
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