CN1138565C - 聚合物键接的喜树碱衍生物 - Google Patents
聚合物键接的喜树碱衍生物 Download PDFInfo
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- CN1138565C CN1138565C CNB941907759A CN94190775A CN1138565C CN 1138565 C CN1138565 C CN 1138565C CN B941907759 A CNB941907759 A CN B941907759A CN 94190775 A CN94190775 A CN 94190775A CN 1138565 C CN1138565 C CN 1138565C
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- Prior art keywords
- phe
- leu
- gly
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- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title claims abstract description 92
- 229920000642 polymer Polymers 0.000 title claims description 17
- 229940127093 camptothecin Drugs 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical group CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000006850 spacer group Chemical group 0.000 claims abstract 7
- BOURDYMMTZXVRY-UHFFFAOYSA-N 2-(2-methylprop-2-enoylamino)acetic acid Chemical compound CC(=C)C(=O)NCC(O)=O BOURDYMMTZXVRY-UHFFFAOYSA-N 0.000 claims abstract 3
- VZKBEZDJWDUUFH-UHFFFAOYSA-N n-[2-(2-hydroxypropylamino)-2-oxoethyl]-2-methylprop-2-enamide Chemical group CC(O)CNC(=O)CNC(=O)C(C)=C VZKBEZDJWDUUFH-UHFFFAOYSA-N 0.000 claims abstract 2
- -1 Phe-G1y-Phe Chemical compound 0.000 claims description 22
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- KFKWRHQBZQICHA-STQMWFEESA-N Leu-Phe Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 KFKWRHQBZQICHA-STQMWFEESA-N 0.000 claims description 4
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- HSQGMTRYSIHDAC-BQBZGAKWSA-N Leu-Ala Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](C)C(O)=O HSQGMTRYSIHDAC-BQBZGAKWSA-N 0.000 claims description 2
- LESXFEZIFXFIQR-LURJTMIESA-N Leu-Gly Chemical compound CC(C)C[C@H](N)C(=O)NCC(O)=O LESXFEZIFXFIQR-LURJTMIESA-N 0.000 claims description 2
- YOKVEHGYYQEQOP-QWRGUYRKSA-N Leu-Leu-Gly Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)NCC(O)=O YOKVEHGYYQEQOP-QWRGUYRKSA-N 0.000 claims description 2
- MIDZLCFIAINOQN-WPRPVWTQSA-N Phe-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CC1=CC=CC=C1 MIDZLCFIAINOQN-WPRPVWTQSA-N 0.000 claims description 2
- GLUBLISJVJFHQS-VIFPVBQESA-N Phe-Gly Chemical compound OC(=O)CNC(=O)[C@@H](N)CC1=CC=CC=C1 GLUBLISJVJFHQS-VIFPVBQESA-N 0.000 claims description 2
- SMFGCTXUBWEPKM-KBPBESRZSA-N Phe-Leu-Gly Chemical compound OC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC1=CC=CC=C1 SMFGCTXUBWEPKM-KBPBESRZSA-N 0.000 claims description 2
- GKZIWHRNKRBEOH-HOTGVXAUSA-N Phe-Phe Chemical compound C([C@H]([NH3+])C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)C1=CC=CC=C1 GKZIWHRNKRBEOH-HOTGVXAUSA-N 0.000 claims description 2
- IWZRODDWOSIXPZ-IRXDYDNUSA-N Phe-Phe-Gly Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC(O)=O)C1=CC=CC=C1 IWZRODDWOSIXPZ-IRXDYDNUSA-N 0.000 claims description 2
- AXIOGMQCDYVTNY-ACRUOGEOSA-N Phe-Phe-Leu Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 AXIOGMQCDYVTNY-ACRUOGEOSA-N 0.000 claims description 2
- CBENHWCORLVGEQ-HJOGWXRNSA-N Phe-Phe-Phe Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 CBENHWCORLVGEQ-HJOGWXRNSA-N 0.000 claims description 2
- QTDBZORPVYTRJU-KKXDTOCCSA-N Phe-Tyr-Ala Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](C)C(O)=O QTDBZORPVYTRJU-KKXDTOCCSA-N 0.000 claims description 2
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- 238000012545 processing Methods 0.000 description 1
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- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/65—Peptidic linkers, binders or spacers, e.g. peptidic enzyme-labile linkers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9320781.9 | 1993-10-08 | ||
| GB939320781A GB9320781D0 (en) | 1993-10-08 | 1993-10-08 | Polymer-bound camptothecin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1115564A CN1115564A (zh) | 1996-01-24 |
| CN1138565C true CN1138565C (zh) | 2004-02-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB941907759A Expired - Fee Related CN1138565C (zh) | 1993-10-08 | 1994-09-21 | 聚合物键接的喜树碱衍生物 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5773522A (https=) |
| EP (1) | EP0673258B1 (https=) |
| JP (1) | JPH08504217A (https=) |
| KR (1) | KR100359005B1 (https=) |
| CN (1) | CN1138565C (https=) |
| AT (1) | ATE239507T1 (https=) |
| AU (1) | AU679788B2 (https=) |
| CA (1) | CA2150132A1 (https=) |
| DE (1) | DE69432627T2 (https=) |
| DK (1) | DK0673258T3 (https=) |
| ES (1) | ES2198421T3 (https=) |
| FI (1) | FI952746A7 (https=) |
| GB (1) | GB9320781D0 (https=) |
| HU (1) | HU215588B (https=) |
| IL (1) | IL111173A (https=) |
| MY (1) | MY116624A (https=) |
| NZ (1) | NZ273952A (https=) |
| PL (1) | PL178132B1 (https=) |
| PT (1) | PT673258E (https=) |
| RU (1) | RU2149646C1 (https=) |
| TW (1) | TW316905B (https=) |
| UA (1) | UA42706C2 (https=) |
| WO (1) | WO1995010304A1 (https=) |
| ZA (1) | ZA947823B (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5880131A (en) * | 1993-10-20 | 1999-03-09 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5965566A (en) * | 1993-10-20 | 1999-10-12 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5646159A (en) * | 1994-07-20 | 1997-07-08 | Research Triangle Institute | Water-soluble esters of camptothecin compounds |
| DE19512484A1 (de) | 1995-04-04 | 1996-10-17 | Bayer Ag | Kohlenhydratmodifizierte Cytostatika |
| SG50747A1 (en) * | 1995-08-02 | 1998-07-20 | Tanabe Seiyaku Co | Comptothecin derivatives |
| CA2192725C (en) * | 1995-12-28 | 2004-04-20 | Kenji Tsujihara | Camptothecin derivatives |
| US6441025B2 (en) * | 1996-03-12 | 2002-08-27 | Pg-Txl Company, L.P. | Water soluble paclitaxel derivatives |
| ATE210673T1 (de) * | 1996-09-30 | 2001-12-15 | Bayer Ag | Glycokonjugate von modifizierten camptothecin- derivaten (20-o-verknüpfung) |
| DE19640969A1 (de) * | 1996-10-04 | 1998-04-16 | Bayer Ag | 20-0-verknüpfte Glycokonjugate von Camptothecin |
| ID23424A (id) | 1997-05-14 | 2000-04-20 | Bayer Ag | Glikokonjugat dari 20(s)-kamptotesin |
| GB9721070D0 (en) * | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Bioactive derivatives of camptothecin |
| GB9721069D0 (en) * | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| US6153655A (en) * | 1998-04-17 | 2000-11-28 | Enzon, Inc. | Terminally-branched polymeric linkers and polymeric conjugates containing the same |
| GB9915180D0 (en) * | 1999-06-29 | 1999-09-01 | Pharmacia & Upjohn Spa | Antitumour compound |
| AU775373B2 (en) | 1999-10-01 | 2004-07-29 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| US20030054977A1 (en) * | 1999-10-12 | 2003-03-20 | Cell Therapeutics, Inc. | Manufacture of polyglutamate-therapeutic agent conjugates |
| WO2001036002A1 (en) * | 1999-11-17 | 2001-05-25 | School Of Pharmacy, University Of London | Conjugates of hpma copolymer and ellipticin |
| US20020077290A1 (en) * | 2000-03-17 | 2002-06-20 | Rama Bhatt | Polyglutamic acid-camptothecin conjugates and methods of preparation |
| GB0008928D0 (en) * | 2000-04-11 | 2000-05-31 | Pharmacia & Upjohn Spa | A method of administering an antitumour compound |
| US6350756B1 (en) | 2001-01-18 | 2002-02-26 | California Pacific Medical Center | Camptothecin derivatives |
| US6403604B1 (en) | 2001-03-01 | 2002-06-11 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| US6855720B2 (en) | 2001-03-01 | 2005-02-15 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| WO2003033525A1 (en) * | 2001-10-12 | 2003-04-24 | Debio Recherche Pharmacuetique S.A. | Amino-substituted camptothecin polymer derivatives and use of the same for the manufacture of a medicament |
| US6933302B2 (en) | 2002-06-03 | 2005-08-23 | California Pacific Medical Center | Nitrogen-based homo-camptothecin derivatives |
| ITPD20050242A1 (it) * | 2005-08-03 | 2007-02-04 | Fidia Farmaceutici | Bioconiugati antitumorali dell'acido ialuronico o dei suoi derivati, ottenibili per coniugazione chimica diretta o indiretta, e loro impiego in campo farmaceutico |
| US7875602B2 (en) | 2005-10-21 | 2011-01-25 | Sutter West Bay Hospitals | Camptothecin derivatives as chemoradiosensitizing agents |
| CN101265331B (zh) * | 2007-03-12 | 2010-10-13 | 中国科学院化学研究所 | Peg改性phpma材料及其制备方法 |
| US9895449B2 (en) | 2010-05-25 | 2018-02-20 | Syndevrx, Inc. | Polymer-conjugated MetAP2 inhibitors, and therapeutic methods of use thereof |
| DK2576638T3 (da) | 2010-05-25 | 2021-03-15 | Syndevrx Inc | Polymerkonjugerede metap2-inhibitorer og terapeutiske fremgangsmåder til anvendelse deraf |
| CN105431426A (zh) | 2013-04-10 | 2016-03-23 | 新德发制药有限公司 | Metap2抑制剂和治疗肥胖症的方法 |
| JP6529130B2 (ja) * | 2013-08-26 | 2019-06-12 | 国立研究開発法人科学技術振興機構 | 接着剤 |
| US9969722B2 (en) | 2015-12-10 | 2018-05-15 | Syndevrx, Inc. | Fumagillol derivatives and polymorphs thereof |
| CN108697807B (zh) | 2016-01-11 | 2021-11-26 | 辛德弗雷克斯公司 | 代谢功能障碍引起的肿瘤的治疗 |
| CN113453721B (zh) | 2018-10-26 | 2025-09-16 | 辛德弗雷克斯公司 | Metap2抑制剂的生物标志物及其应用 |
Family Cites Families (5)
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| US4943579A (en) * | 1987-10-06 | 1990-07-24 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Water soluble prodrugs of camptothecin |
| GB9200247D0 (en) * | 1992-01-07 | 1992-02-26 | Erba Carlo Spa | Pharmaceutical compositions containing polymer derivative-bound anthracycline glycosides and a method for their preparation |
| US5258453A (en) * | 1992-01-21 | 1993-11-02 | University Of Utah | Drug delivery system for the simultaneous delivery of drugs activatable by enzymes and light |
| GB9213077D0 (en) * | 1992-06-19 | 1992-08-05 | Erba Carlo Spa | Polymerbound taxol derivatives |
| GB9309663D0 (en) * | 1993-05-11 | 1993-06-23 | Erba Carlo Spa | Biologically active compounds |
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1993
- 1993-10-08 GB GB939320781A patent/GB9320781D0/en active Pending
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1994
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- 1994-09-21 DK DK94928387T patent/DK0673258T3/da active
- 1994-09-21 EP EP94928387A patent/EP0673258B1/en not_active Expired - Lifetime
- 1994-09-21 CN CNB941907759A patent/CN1138565C/zh not_active Expired - Fee Related
- 1994-09-21 KR KR1019950702308A patent/KR100359005B1/ko not_active Expired - Fee Related
- 1994-09-21 RU RU95112841A patent/RU2149646C1/ru not_active IP Right Cessation
- 1994-09-21 JP JP7511221A patent/JPH08504217A/ja active Pending
- 1994-09-21 WO PCT/EP1994/003154 patent/WO1995010304A1/en not_active Ceased
- 1994-09-21 US US08/448,330 patent/US5773522A/en not_active Expired - Fee Related
- 1994-09-21 CA CA002150132A patent/CA2150132A1/en not_active Abandoned
- 1994-09-21 AT AT94928387T patent/ATE239507T1/de not_active IP Right Cessation
- 1994-09-21 NZ NZ273952A patent/NZ273952A/en unknown
- 1994-09-21 PL PL94309328A patent/PL178132B1/pl not_active IP Right Cessation
- 1994-09-21 PT PT94928387T patent/PT673258E/pt unknown
- 1994-09-21 AU AU77836/94A patent/AU679788B2/en not_active Ceased
- 1994-09-21 DE DE69432627T patent/DE69432627T2/de not_active Expired - Fee Related
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- 1994-09-21 UA UA95073111A patent/UA42706C2/uk unknown
- 1994-09-21 FI FI952746A patent/FI952746A7/fi unknown
- 1994-09-22 TW TW083108713A patent/TW316905B/zh active
- 1994-10-05 IL IL11117394A patent/IL111173A/en not_active IP Right Cessation
- 1994-10-06 ZA ZA947823A patent/ZA947823B/xx unknown
- 1994-10-06 MY MYPI94002652A patent/MY116624A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7783694A (en) | 1995-05-04 |
| RU2149646C1 (ru) | 2000-05-27 |
| HU9502084D0 (en) | 1995-09-28 |
| DE69432627T2 (de) | 2004-03-25 |
| PL309328A1 (en) | 1995-10-02 |
| KR100359005B1 (ko) | 2003-04-26 |
| HU215588B (hu) | 1999-01-28 |
| DE69432627D1 (en) | 2003-06-12 |
| IL111173A0 (en) | 1994-12-29 |
| AU679788B2 (en) | 1997-07-10 |
| ZA947823B (en) | 1995-07-03 |
| NZ273952A (en) | 1996-10-28 |
| GB9320781D0 (en) | 1993-12-01 |
| IL111173A (en) | 1998-10-30 |
| EP0673258B1 (en) | 2003-05-07 |
| WO1995010304A1 (en) | 1995-04-20 |
| HUT71678A (en) | 1996-01-29 |
| RU95112841A (ru) | 1997-06-27 |
| PL178132B1 (pl) | 2000-03-31 |
| FI952746A0 (fi) | 1995-06-05 |
| ES2198421T3 (es) | 2004-02-01 |
| CN1115564A (zh) | 1996-01-24 |
| FI952746A7 (fi) | 1995-06-05 |
| MY116624A (en) | 2004-03-31 |
| UA42706C2 (uk) | 2001-11-15 |
| US5773522A (en) | 1998-06-30 |
| TW316905B (https=) | 1997-10-01 |
| CA2150132A1 (en) | 1995-04-20 |
| JPH08504217A (ja) | 1996-05-07 |
| EP0673258A1 (en) | 1995-09-27 |
| PT673258E (pt) | 2003-09-30 |
| ATE239507T1 (de) | 2003-05-15 |
| DK0673258T3 (da) | 2003-08-25 |
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Correction item: International date of application, international application number, international date of entry Correct: 1994.09.21 PCT/EP1994/03154 1995.06.08 Number: 7 Page: 370 Volume: 20 |
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Correction item: International date of application, international application number, international date of entry Correct: 1994.09.21 PCT/EP1994/03154 1995.06.08 Number: 7 Page: The title page Volume: 20 |
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