NO327995B1 - Krystallinsk form av vannfritt 1S-[1alfa(2S*,3R*), 9alfa]6,10-diokso-N-(2-etoksy-5-okso-tetrahydro-3-furanyl)-9[[(1-isokinolyl)karbonyl]amino]oktahydro-6H-piridazino[1,2-a][1,2]diazepin-1-karboksamid (form A), fremgangsmate for fremstilling av denne, og anvendelse av den for fremstilling av et medikament - Google Patents
Krystallinsk form av vannfritt 1S-[1alfa(2S*,3R*), 9alfa]6,10-diokso-N-(2-etoksy-5-okso-tetrahydro-3-furanyl)-9[[(1-isokinolyl)karbonyl]amino]oktahydro-6H-piridazino[1,2-a][1,2]diazepin-1-karboksamid (form A), fremgangsmate for fremstilling av denne, og anvendelse av den for fremstilling av et medikament Download PDFInfo
- Publication number
- NO327995B1 NO327995B1 NO20005060A NO20005060A NO327995B1 NO 327995 B1 NO327995 B1 NO 327995B1 NO 20005060 A NO20005060 A NO 20005060A NO 20005060 A NO20005060 A NO 20005060A NO 327995 B1 NO327995 B1 NO 327995B1
- Authority
- NO
- Norway
- Prior art keywords
- crystalline form
- drug
- diazepine
- dioxo
- carboxamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000003814 drug Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 229940079593 drug Drugs 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 11
- -1 2-ethoxy-5-oxo-tetrahydro-3-furanyl Chemical group 0.000 title 1
- PPIXVPFGMODPHO-UHFFFAOYSA-N N'-(isoquinoline-1-carbonyl)-2,3,4,6,7,8,9,10-octahydro-1H-pyridazino[1,2-a]diazepine-4-carbohydrazide Chemical compound C1(CCCN2N1CCCCC2)C(=O)NNC(=O)C1=NC=CC2=CC=CC=C12 PPIXVPFGMODPHO-UHFFFAOYSA-N 0.000 title 1
- 238000002425 crystallisation Methods 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000009102 absorption Effects 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 230000001363 autoimmune Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- AUHBCNJHXCDLMK-UHFFFAOYSA-N diazepine-1-carboxamide Chemical compound NC(=O)N1C=CC=CC=N1 AUHBCNJHXCDLMK-UHFFFAOYSA-N 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- LAOZSCRCYVBSJA-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CC1(C)C(=O)NC(=O)NC1=O LAOZSCRCYVBSJA-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- QRKPPWPLSQRGSU-UHFFFAOYSA-N diazepine-1-carboxylic acid Chemical compound OC(=O)N1C=CC=CC=N1 QRKPPWPLSQRGSU-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P37/02—Immunomodulators
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9804367A FR2777279B1 (fr) | 1998-04-08 | 1998-04-08 | Nouvelles formes cristallines du 1s-[1alpha(2s*,3r*), 9 alpha] 6,10-dioxo-n-(2-ethoxy-5-oxo-tetrahydro-3-furanyl) -9[[(1-isoquinolyl)carbonyl]amino]octohydro-6h-pyridazino [1,2-a][1,2]diazepine-1-carboxamide |
| PCT/FR1999/000799 WO1999052935A1 (fr) | 1998-04-08 | 1999-04-07 | Formes cristallines du 1s-[1alpha (2s*,3r*),9alpha]-6, 10-dioxo-n- (2-ethoxy-5 -oxo-tetrahydro-3 -furanyl) -9-[[(1-isoquinolyl) carbonyl]-amino] octahydro-6h -piridazino[1, 2-a][1,2] diazepine-1- carboxamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20005060D0 NO20005060D0 (no) | 2000-10-06 |
| NO20005060L NO20005060L (no) | 2000-10-06 |
| NO327995B1 true NO327995B1 (no) | 2009-11-02 |
Family
ID=9524993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20005060A NO327995B1 (no) | 1998-04-08 | 2000-10-06 | Krystallinsk form av vannfritt 1S-[1alfa(2S*,3R*), 9alfa]6,10-diokso-N-(2-etoksy-5-okso-tetrahydro-3-furanyl)-9[[(1-isokinolyl)karbonyl]amino]oktahydro-6H-piridazino[1,2-a][1,2]diazepin-1-karboksamid (form A), fremgangsmate for fremstilling av denne, og anvendelse av den for fremstilling av et medikament |
Country Status (38)
| Country | Link |
|---|---|
| US (2) | US6544977B1 (de) |
| EP (1) | EP1070083B1 (de) |
| JP (1) | JP2002511485A (de) |
| KR (1) | KR100582981B1 (de) |
| CN (1) | CN1202123C (de) |
| AP (1) | AP1734A (de) |
| AR (1) | AR018328A1 (de) |
| AT (1) | ATE315044T1 (de) |
| AU (1) | AU758042B2 (de) |
| BG (1) | BG64736B1 (de) |
| BR (1) | BR9909549A (de) |
| CA (1) | CA2325629C (de) |
| CU (1) | CU23055A3 (de) |
| CZ (1) | CZ299744B6 (de) |
| DE (1) | DE69929315T2 (de) |
| DK (1) | DK1070083T3 (de) |
| EA (1) | EA002761B1 (de) |
| EE (1) | EE04467B1 (de) |
| ES (1) | ES2253880T3 (de) |
| FR (1) | FR2777279B1 (de) |
| GE (1) | GEP20032974B (de) |
| HK (1) | HK1038575B (de) |
| HR (1) | HRP20000665B1 (de) |
| HU (1) | HU227561B1 (de) |
| ID (1) | ID26290A (de) |
| IL (2) | IL138818A (de) |
| ME (1) | ME01627B (de) |
| NO (1) | NO327995B1 (de) |
| NZ (1) | NZ507199A (de) |
| PL (1) | PL197016B1 (de) |
| RS (1) | RS49916B (de) |
| SI (1) | SI1070083T1 (de) |
| SK (1) | SK286267B6 (de) |
| TR (1) | TR200002914T2 (de) |
| TW (1) | TW522152B (de) |
| UA (1) | UA71563C2 (de) |
| WO (1) | WO1999052935A1 (de) |
| ZA (1) | ZA200005438B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8198450B2 (en) * | 2006-06-30 | 2012-06-12 | Novartis Ag | Quinolinone derivatives and their pharmaceutical compositions |
| AU2014277867B2 (en) * | 2007-12-04 | 2016-11-03 | Arbutus Biopharma Corporation | Targeting lipids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6204261B1 (en) * | 1995-12-20 | 2001-03-20 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β Converting enzyme inhibitors |
| US5552400A (en) * | 1994-06-08 | 1996-09-03 | Sterling Winthrop Inc. | Fused-bicyclic lactams as interleukin-1β converting enzyme inhibitors |
-
1998
- 1998-04-08 FR FR9804367A patent/FR2777279B1/fr not_active Expired - Lifetime
-
1999
- 1999-03-15 TW TW088103966A patent/TW522152B/zh not_active IP Right Cessation
- 1999-03-30 AR ARP990101432A patent/AR018328A1/es active IP Right Grant
- 1999-04-07 US US09/647,858 patent/US6544977B1/en not_active Expired - Lifetime
- 1999-04-07 EA EA200001047A patent/EA002761B1/ru not_active IP Right Cessation
- 1999-04-07 NZ NZ507199A patent/NZ507199A/xx not_active IP Right Cessation
- 1999-04-07 ME MEP-2000-608A patent/ME01627B/me unknown
- 1999-04-07 AU AU30416/99A patent/AU758042B2/en not_active Ceased
- 1999-04-07 ID IDW20002015A patent/ID26290A/id unknown
- 1999-04-07 BR BR9909549-1A patent/BR9909549A/pt not_active Application Discontinuation
- 1999-04-07 AT AT99911890T patent/ATE315044T1/de active
- 1999-04-07 JP JP2000543491A patent/JP2002511485A/ja active Pending
- 1999-04-07 DK DK99911890T patent/DK1070083T3/da active
- 1999-04-07 DE DE69929315T patent/DE69929315T2/de not_active Expired - Lifetime
- 1999-04-07 RS YUP-608/00A patent/RS49916B/sr unknown
- 1999-04-07 HU HU0101586A patent/HU227561B1/hu not_active IP Right Cessation
- 1999-04-07 AP APAP/P/2000/001939A patent/AP1734A/en active
- 1999-04-07 SI SI9930877T patent/SI1070083T1/sl unknown
- 1999-04-07 EE EEP200000586A patent/EE04467B1/xx unknown
- 1999-04-07 PL PL343350A patent/PL197016B1/pl unknown
- 1999-04-07 SK SK1488-2000A patent/SK286267B6/sk not_active IP Right Cessation
- 1999-04-07 TR TR2000/02914T patent/TR200002914T2/xx unknown
- 1999-04-07 CZ CZ20003678A patent/CZ299744B6/cs not_active IP Right Cessation
- 1999-04-07 KR KR1020007011159A patent/KR100582981B1/ko not_active IP Right Cessation
- 1999-04-07 WO PCT/FR1999/000799 patent/WO1999052935A1/fr active IP Right Grant
- 1999-04-07 GE GEAP19995614A patent/GEP20032974B/en unknown
- 1999-04-07 CN CNB998071455A patent/CN1202123C/zh not_active Expired - Fee Related
- 1999-04-07 CA CA2325629A patent/CA2325629C/fr not_active Expired - Fee Related
- 1999-04-07 ES ES99911890T patent/ES2253880T3/es not_active Expired - Lifetime
- 1999-04-07 CU CU20000213A patent/CU23055A3/es unknown
- 1999-04-07 EP EP99911890A patent/EP1070083B1/de not_active Expired - Lifetime
- 1999-07-04 UA UA2000116295A patent/UA71563C2/uk unknown
-
2000
- 2000-10-02 IL IL138818A patent/IL138818A/en not_active IP Right Cessation
- 2000-10-05 ZA ZA200005438A patent/ZA200005438B/en unknown
- 2000-10-06 NO NO20005060A patent/NO327995B1/no not_active IP Right Cessation
- 2000-10-06 BG BG104829A patent/BG64736B1/bg unknown
- 2000-10-09 HR HR20000665A patent/HRP20000665B1/xx not_active IP Right Cessation
-
2002
- 2002-01-07 HK HK02100107.8A patent/HK1038575B/zh not_active IP Right Cessation
- 2002-11-18 US US10/299,242 patent/US6946459B2/en not_active Expired - Lifetime
-
2005
- 2005-04-14 IL IL168047A patent/IL168047A/en not_active IP Right Cessation
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