SK101198A3 - Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents - Google Patents
Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents Download PDFInfo
- Publication number
- SK101198A3 SK101198A3 SK1011-98A SK101198A SK101198A3 SK 101198 A3 SK101198 A3 SK 101198A3 SK 101198 A SK101198 A SK 101198A SK 101198 A3 SK101198 A3 SK 101198A3
- Authority
- SK
- Slovakia
- Prior art keywords
- compounds
- formula
- group
- pyridyl
- desphenyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 19
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 title claims description 4
- 239000002246 antineoplastic agent Substances 0.000 title description 3
- PIINXYKJQGMIOZ-UHFFFAOYSA-N 1,2-dipyridin-2-ylethane-1,2-dione Chemical group C=1C=CC=NC=1C(=O)C(=O)C1=CC=CC=N1 PIINXYKJQGMIOZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 230000032050 esterification Effects 0.000 claims abstract description 10
- 238000005886 esterification reaction Methods 0.000 claims abstract description 10
- 238000006266 etherification reaction Methods 0.000 claims abstract description 8
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 6
- 229940123237 Taxane Drugs 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims abstract description 3
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-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)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 HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims abstract description 3
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims abstract description 3
- 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 claims abstract description 3
- 229960004853 betadex Drugs 0.000 claims abstract description 3
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-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)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 GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims abstract description 3
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims abstract description 3
- 239000002502 liposome Substances 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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- 239000000654 additive Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 abstract description 24
- 229930012538 Paclitaxel Natural products 0.000 abstract description 15
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 abstract description 15
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- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000000027 (C1-C10) alkoxy group Chemical class 0.000 abstract 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- 239000000203 mixture Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- -1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- 230000000699 topical effect Effects 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009529 traumatic brain injury Effects 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 229960002324 trifluoperazine Drugs 0.000 description 1
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19605024A DE19605024A1 (de) | 1996-01-31 | 1996-01-31 | Neue selektive Taxane, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| PCT/EP1997/000440 WO1997028156A1 (en) | 1996-01-31 | 1997-01-31 | Taxane derivatives having a pyridyl substituted c13 side chain, their preparation and their use as anti-tumor agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK101198A3 true SK101198A3 (en) | 1998-12-02 |
Family
ID=7785142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1011-98A SK101198A3 (en) | 1996-01-31 | 1997-01-31 | Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6162920A (de) |
| EP (1) | EP0896577B1 (de) |
| JP (1) | JP2001505527A (de) |
| KR (1) | KR19990082151A (de) |
| CN (1) | CN1073108C (de) |
| AT (1) | ATE233757T1 (de) |
| AU (1) | AU714313B2 (de) |
| BR (1) | BR9708295A (de) |
| CA (1) | CA2244746A1 (de) |
| CZ (1) | CZ292504B6 (de) |
| DE (2) | DE19605024A1 (de) |
| DK (1) | DK0896577T3 (de) |
| ES (1) | ES2192261T3 (de) |
| HK (1) | HK1018778A1 (de) |
| HU (1) | HUP9901027A3 (de) |
| IL (1) | IL124951A (de) |
| NO (1) | NO983509L (de) |
| PL (1) | PL186796B1 (de) |
| PT (1) | PT896577E (de) |
| RU (1) | RU2163599C2 (de) |
| SK (1) | SK101198A3 (de) |
| TR (1) | TR199801415T2 (de) |
| TW (1) | TW444015B (de) |
| UA (1) | UA49007C2 (de) |
| WO (1) | WO1997028156A1 (de) |
| ZA (1) | ZA97847B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2311591T3 (es) | 2001-03-07 | 2009-02-16 | Daiichi Sankyo Company, Limited | Proceso para producir un derivado de 2-azetidinona. |
| EP1605866B1 (de) | 2003-03-03 | 2016-07-06 | Syntach AG | Implantatvorrichtung für elektrischen leitungsblock |
| CN1296391C (zh) * | 2004-03-04 | 2007-01-24 | 中国人民解放军第二军医大学 | 氟代羧烷基环糊精醚类化合物及其制备方法和应用 |
| US8658203B2 (en) | 2004-05-03 | 2014-02-25 | Merrimack Pharmaceuticals, Inc. | Liposomes useful for drug delivery to the brain |
| CA2821167C (en) | 2004-05-03 | 2016-06-28 | Merrimack Pharmaceuticals, Inc. | Drug delivery liposomes containing anionic polyols or anionic sugars |
| AU2013202947B2 (en) | 2012-06-13 | 2016-06-02 | Ipsen Biopharm Ltd. | Methods for treating pancreatic cancer using combination therapies comprising liposomal irinotecan |
| US9717724B2 (en) | 2012-06-13 | 2017-08-01 | Ipsen Biopharm Ltd. | Methods for treating pancreatic cancer using combination therapies |
| US11318131B2 (en) | 2015-05-18 | 2022-05-03 | Ipsen Biopharm Ltd. | Nanoliposomal irinotecan for use in treating small cell lung cancer |
| TWI724018B (zh) | 2015-08-20 | 2021-04-11 | 英商益普生生物製藥有限公司 | 用於癌症治療之組合療法 |
| EP3337478B1 (de) | 2015-08-21 | 2020-08-12 | Ipsen Biopharm Ltd. | Arzneimittelkombination enthaltend liposomales irinotecan, oxaliplatin, 5-fluorouracil und leucovorin zur behandlung von metastasierendem pankreaskrebs |
| SG10201912568PA (en) | 2015-10-16 | 2020-02-27 | Ipsen Biopharm Ltd | Stabilizing camptothecin pharmaceutical compositions |
| MX2019004783A (es) | 2016-11-02 | 2019-08-12 | Ipsen Biopharm Ltd | Tratamiento de cancer gastrico usando terapias de combinacion que comprenden irinotecan liposomico oxaliplatino, 5-fluoruracilo (y leucovorina). |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227400A (en) * | 1991-09-23 | 1993-07-13 | Florida State University | Furyl and thienyl substituted taxanes and pharmaceutical compositions containing them |
| US5489601A (en) * | 1991-09-23 | 1996-02-06 | Florida State University | Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them |
| IL109049A (en) * | 1993-03-22 | 2006-12-31 | Univ Florida State | Texans have a side chain that is converted into pyridyl and pharmaceutical preparations that contain them |
| US5415869A (en) * | 1993-11-12 | 1995-05-16 | The Research Foundation Of State University Of New York | Taxol formulation |
| FR2715307B1 (fr) * | 1994-01-25 | 1996-04-05 | Commissariat Energie Atomique | Procédé de solubilisation dans un milieu aqueux d'agents antitumoraux de la famille du taxol, et cyclodextrines ramifiées utilisables pour cette solubilisation. |
| ES2123996T3 (es) * | 1994-06-28 | 1999-01-16 | Upjohn Co | Analogos de 7-etertaxol, uso antineoplasico y composiciones farmaceuticas que los contienen. |
-
1996
- 1996-01-31 DE DE19605024A patent/DE19605024A1/de not_active Withdrawn
-
1997
- 1997-01-31 PL PL97328055A patent/PL186796B1/pl not_active IP Right Cessation
- 1997-01-31 RU RU98116122/04A patent/RU2163599C2/ru not_active IP Right Cessation
- 1997-01-31 DK DK97902286T patent/DK0896577T3/da active
- 1997-01-31 JP JP52730897A patent/JP2001505527A/ja active Pending
- 1997-01-31 HU HU9901027A patent/HUP9901027A3/hu unknown
- 1997-01-31 CA CA002244746A patent/CA2244746A1/en not_active Abandoned
- 1997-01-31 EP EP97902286A patent/EP0896577B1/de not_active Expired - Lifetime
- 1997-01-31 SK SK1011-98A patent/SK101198A3/sk unknown
- 1997-01-31 WO PCT/EP1997/000440 patent/WO1997028156A1/en not_active Application Discontinuation
- 1997-01-31 AU AU15984/97A patent/AU714313B2/en not_active Ceased
- 1997-01-31 CN CN97192006A patent/CN1073108C/zh not_active Expired - Fee Related
- 1997-01-31 CZ CZ19982426A patent/CZ292504B6/cs not_active IP Right Cessation
- 1997-01-31 US US09/117,506 patent/US6162920A/en not_active Expired - Fee Related
- 1997-01-31 ZA ZA9700847A patent/ZA97847B/xx unknown
- 1997-01-31 DE DE69719502T patent/DE69719502T2/de not_active Expired - Lifetime
- 1997-01-31 TW TW086101169A patent/TW444015B/zh active
- 1997-01-31 UA UA98084638A patent/UA49007C2/uk unknown
- 1997-01-31 KR KR1019980705874A patent/KR19990082151A/ko not_active Application Discontinuation
- 1997-01-31 BR BR9708295A patent/BR9708295A/pt not_active Application Discontinuation
- 1997-01-31 AT AT97902286T patent/ATE233757T1/de not_active IP Right Cessation
- 1997-01-31 TR TR1998/01415T patent/TR199801415T2/xx unknown
- 1997-01-31 PT PT97902286T patent/PT896577E/pt unknown
- 1997-01-31 IL IL12495197A patent/IL124951A/xx not_active IP Right Cessation
- 1997-01-31 ES ES97902286T patent/ES2192261T3/es not_active Expired - Lifetime
-
1998
- 1998-07-30 NO NO983509A patent/NO983509L/no unknown
-
1999
- 1999-09-02 HK HK99103795A patent/HK1018778A1/xx not_active IP Right Cessation
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