NO326464B1 - Analoger av camptotecin, anvendelse derav, samt medikament - Google Patents
Analoger av camptotecin, anvendelse derav, samt medikament Download PDFInfo
- Publication number
- NO326464B1 NO326464B1 NO19992998A NO992998A NO326464B1 NO 326464 B1 NO326464 B1 NO 326464B1 NO 19992998 A NO19992998 A NO 19992998A NO 992998 A NO992998 A NO 992998A NO 326464 B1 NO326464 B1 NO 326464B1
- Authority
- NO
- Norway
- Prior art keywords
- quinoline
- ethyl
- dihydro
- hydroxy
- dione
- Prior art date
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 229910002651 NO3 Inorganic materials 0.000 description 1
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
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- 229930013930 alkaloid Natural products 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
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- 229960003677 chloroquine Drugs 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
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- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 1
- 229960005542 ethidium bromide Drugs 0.000 description 1
- MBMGTUOUOVDVDO-UHFFFAOYSA-N ethyl 2-chloro-4-(chloromethyl)-6-fluoroquinoline-3-carboxylate Chemical compound C1=CC(F)=CC2=C(CCl)C(C(=O)OCC)=C(Cl)N=C21 MBMGTUOUOVDVDO-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 210000005267 prostate cell Anatomy 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9615774A FR2757514B1 (fr) | 1996-12-20 | 1996-12-20 | Nouveaux analogues de la camptothecine, des procedes de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| PCT/FR1997/002218 WO1998028305A1 (fr) | 1996-12-20 | 1997-12-05 | Nouveaux analogues de la camptothecine, leur application comme medicaments et les compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992998D0 NO992998D0 (no) | 1999-06-18 |
| NO992998L NO992998L (no) | 1999-08-18 |
| NO326464B1 true NO326464B1 (no) | 2008-12-08 |
Family
ID=9498938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19992998A NO326464B1 (no) | 1996-12-20 | 1999-06-18 | Analoger av camptotecin, anvendelse derav, samt medikament |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0946567B1 (de) |
| JP (2) | JP3576175B2 (de) |
| KR (1) | KR100516874B1 (de) |
| CN (1) | CN1097056C (de) |
| AR (1) | AR008543A1 (de) |
| AT (1) | ATE248177T1 (de) |
| AU (1) | AU734485B2 (de) |
| BR (1) | BR9714170A (de) |
| CA (1) | CA2275351C (de) |
| CZ (1) | CZ299795B6 (de) |
| DE (1) | DE69724453T2 (de) |
| DK (1) | DK0946567T3 (de) |
| ES (1) | ES2206761T3 (de) |
| FR (1) | FR2757514B1 (de) |
| HK (1) | HK1024695A1 (de) |
| HU (1) | HUP9904210A3 (de) |
| MX (1) | MXPA99005776A (de) |
| MY (1) | MY119473A (de) |
| NO (1) | NO326464B1 (de) |
| NZ (1) | NZ335939A (de) |
| PL (1) | PL188181B1 (de) |
| PT (1) | PT946567E (de) |
| RU (1) | RU2194051C2 (de) |
| UA (1) | UA57758C2 (de) |
| WO (1) | WO1998028305A1 (de) |
| ZA (1) | ZA9711129B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2790261B1 (fr) * | 1999-02-26 | 2004-09-10 | Sod Conseils Rech Applic | Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation |
| US6291676B1 (en) * | 1999-03-03 | 2001-09-18 | University Of Kentucky Research Foundation | Water-soluble derivatives of camptothecin/homocamptothecin |
| US6207832B1 (en) | 1999-04-09 | 2001-03-27 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| AU3455100A (en) * | 1999-05-28 | 2000-12-18 | Nippon Chemiphar Co. Ltd. | Process for the preparation of 2-halo-3-(3-quinolyl)propionic acid derivatives |
| US6372906B1 (en) | 2001-04-12 | 2002-04-16 | University Of Pittsburgh | Synthesis of silyl camptothecins and silyl homocamptothecins |
| US6723853B2 (en) | 2001-08-27 | 2004-04-20 | University Of Pittsburgh | Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins |
| AU2003225642A1 (en) * | 2002-03-01 | 2003-09-16 | Fluorous Techonologies Inc | Mappicine analogs, intermediates in the synthesis of mappicine analogs and methods of synthesis of mappicine analogs |
| ITRM20040288A1 (it) * | 2004-06-11 | 2004-09-11 | Sigma Tau Ind Farmaceuti | Uso della 7-t-butossiimminometilcamptotecina per la preparazione di un medicamento per il trattamento delle neoplasie dell'utero. |
| EP1794127A1 (de) * | 2004-09-21 | 2007-06-13 | Société de Conseils de Recherches et d'Applications Scientifiques ( S.C.R.A.S.) | Neue verfahren zur herstellung von nützlichen zwischenprodukten |
| CN102746314B (zh) * | 2011-04-18 | 2016-07-06 | 华东师范大学 | 含有稳定7元内酯环的喜树碱类化合物、制备方法和用途 |
| CN117164601A (zh) * | 2022-06-02 | 2023-12-05 | 华东师范大学 | 一种高喜树碱类小分子及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391745A (en) * | 1992-07-23 | 1995-02-21 | Sloan-Kettering Institute For Cancer Research | Methods of preparation of camptothecin analogs |
| RU2164515C2 (ru) * | 1995-06-21 | 2001-03-27 | Сосьете де Консей де Решерш э Д'Аппликасьон Сьентифик (СКРАС) | Соединения камптотецина, способы их получения, промежуточные соединения и терапевтические композиции |
-
1996
- 1996-12-20 FR FR9615774A patent/FR2757514B1/fr not_active Expired - Fee Related
-
1997
- 1997-05-12 UA UA99063449A patent/UA57758C2/uk unknown
- 1997-12-05 CA CA002275351A patent/CA2275351C/fr not_active Expired - Fee Related
- 1997-12-05 PL PL97334125A patent/PL188181B1/pl not_active IP Right Cessation
- 1997-12-05 NZ NZ335939A patent/NZ335939A/xx not_active IP Right Cessation
- 1997-12-05 CN CN97180815A patent/CN1097056C/zh not_active Expired - Fee Related
- 1997-12-05 AU AU53265/98A patent/AU734485B2/en not_active Ceased
- 1997-12-05 JP JP52844898A patent/JP3576175B2/ja not_active Expired - Fee Related
- 1997-12-05 DE DE69724453T patent/DE69724453T2/de not_active Expired - Lifetime
- 1997-12-05 KR KR10-1999-7005603A patent/KR100516874B1/ko not_active IP Right Cessation
- 1997-12-05 EP EP97950236A patent/EP0946567B1/de not_active Expired - Lifetime
- 1997-12-05 BR BR9714170-4A patent/BR9714170A/pt not_active Application Discontinuation
- 1997-12-05 RU RU99115829/04A patent/RU2194051C2/ru not_active IP Right Cessation
- 1997-12-05 AT AT97950236T patent/ATE248177T1/de active
- 1997-12-05 CZ CZ0220599A patent/CZ299795B6/cs not_active IP Right Cessation
- 1997-12-05 WO PCT/FR1997/002218 patent/WO1998028305A1/fr active IP Right Grant
- 1997-12-05 HU HU9904210A patent/HUP9904210A3/hu unknown
- 1997-12-05 ES ES97950236T patent/ES2206761T3/es not_active Expired - Lifetime
- 1997-12-05 DK DK97950236T patent/DK0946567T3/da active
- 1997-12-05 MX MXPA99005776A patent/MXPA99005776A/es not_active IP Right Cessation
- 1997-12-05 PT PT97950236T patent/PT946567E/pt unknown
- 1997-12-10 ZA ZA9711129A patent/ZA9711129B/xx unknown
- 1997-12-17 MY MYPI97006088A patent/MY119473A/en unknown
- 1997-12-19 AR ARP970106043A patent/AR008543A1/es active IP Right Grant
-
1999
- 1999-06-18 NO NO19992998A patent/NO326464B1/no not_active IP Right Cessation
-
2000
- 2000-07-04 HK HK00104036A patent/HK1024695A1/xx not_active IP Right Cessation
-
2003
- 2003-11-26 JP JP2003395513A patent/JP2004115535A/ja not_active Withdrawn
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