NO323230B1 - Mikrogranulater for kontrollert frigjoring for oral administrering som inneholder cisplatin, farmasoytiske preparater derav og anvendelse derav. - Google Patents
Mikrogranulater for kontrollert frigjoring for oral administrering som inneholder cisplatin, farmasoytiske preparater derav og anvendelse derav. Download PDFInfo
- Publication number
- NO323230B1 NO323230B1 NO19993881A NO993881A NO323230B1 NO 323230 B1 NO323230 B1 NO 323230B1 NO 19993881 A NO19993881 A NO 19993881A NO 993881 A NO993881 A NO 993881A NO 323230 B1 NO323230 B1 NO 323230B1
- Authority
- NO
- Norway
- Prior art keywords
- microgranules
- cisplatin
- stated
- coating
- mixture
- Prior art date
Links
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 title claims abstract description 89
- 229960004316 cisplatin Drugs 0.000 title claims abstract description 88
- 238000013270 controlled release Methods 0.000 title claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 6
- 238000011319 anticancer therapy Methods 0.000 claims abstract description 3
- 239000013066 combination product Substances 0.000 claims abstract description 3
- 229940127555 combination product Drugs 0.000 claims abstract description 3
- 239000011248 coating agent Substances 0.000 claims description 34
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 108010006654 Bleomycin Proteins 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 229960001561 bleomycin Drugs 0.000 claims description 6
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000008280 blood Substances 0.000 claims description 5
- 210000004369 blood Anatomy 0.000 claims description 5
- 239000010410 layer Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000000454 talc Substances 0.000 claims description 5
- 229910052623 talc Inorganic materials 0.000 claims description 5
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical group FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
- 229960002949 fluorouracil Drugs 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 229930012538 Paclitaxel Natural products 0.000 claims description 3
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 3
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 3
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide 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](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
- 229960005420 etoposide Drugs 0.000 claims description 3
- 239000002609 medium Substances 0.000 claims description 3
- 229960001592 paclitaxel Drugs 0.000 claims description 3
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- 238000001959 radiotherapy Methods 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 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 claims description 3
- 239000001069 triethyl citrate Substances 0.000 claims description 3
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 3
- 235000013769 triethyl citrate Nutrition 0.000 claims description 3
- 229960003048 vinblastine Drugs 0.000 claims description 3
- 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 claims description 3
- RYYCJUAHISIHTL-UHFFFAOYSA-N 5-azaorotic acid Chemical compound OC(=O)C1=NC(=O)NC(=O)N1 RYYCJUAHISIHTL-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- ZPLQIPFOCGIIHV-UHFFFAOYSA-N Gimeracil Chemical compound OC1=CC(=O)C(Cl)=CN1 ZPLQIPFOCGIIHV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 238000002512 chemotherapy Methods 0.000 claims description 2
- 229950009822 gimeracil Drugs 0.000 claims description 2
- 229950000193 oteracil Drugs 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- 229940068968 polysorbate 80 Drugs 0.000 claims description 2
- 239000011253 protective coating Substances 0.000 claims description 2
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 claims description 2
- 229960001674 tegafur Drugs 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 12
- 238000009472 formulation Methods 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 abstract description 5
- 238000009096 combination chemotherapy Methods 0.000 abstract description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
- 241000282472 Canis lupus familiaris Species 0.000 description 10
- 229910052697 platinum Inorganic materials 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 230000003111 delayed effect Effects 0.000 description 7
- 238000001990 intravenous administration Methods 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
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- 231100000417 nephrotoxicity Toxicity 0.000 description 5
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- 241000700159 Rattus Species 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000001093 anti-cancer Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007972 injectable composition Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 210000001185 bone marrow Anatomy 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
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- 230000036571 hydration Effects 0.000 description 2
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- 230000003902 lesion Effects 0.000 description 2
- 239000004531 microgranule Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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- 208000004880 Polyuria Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229930006000 Sucrose Natural products 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
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- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
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- 210000000936 intestine Anatomy 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
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- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
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- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
- A61K9/1676—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface having a drug-free core with discrete complete coating layer containing drug
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9701545A FR2759293B1 (fr) | 1997-02-11 | 1997-02-11 | Microgranules contenant du cisplatine, procede de fabrication, preparation pharmaceutique et utilisation en polychimiotherapie ou en association avec une radiotherapie |
| PCT/FR1998/000251 WO1998034599A1 (fr) | 1997-02-11 | 1998-02-10 | Microgranules contenant du cisplatine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993881D0 NO993881D0 (no) | 1999-08-11 |
| NO993881L NO993881L (no) | 1999-09-29 |
| NO323230B1 true NO323230B1 (no) | 2007-02-05 |
Family
ID=9503556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993881A NO323230B1 (no) | 1997-02-11 | 1999-08-11 | Mikrogranulater for kontrollert frigjoring for oral administrering som inneholder cisplatin, farmasoytiske preparater derav og anvendelse derav. |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6458389B1 (https=) |
| EP (1) | EP0971702B1 (https=) |
| JP (1) | JP4549445B2 (https=) |
| KR (1) | KR100471672B1 (https=) |
| AR (1) | AR011133A1 (https=) |
| AT (1) | ATE255409T1 (https=) |
| BG (1) | BG64247B1 (https=) |
| BR (1) | BR9807319A (https=) |
| CA (1) | CA2282082C (https=) |
| DE (1) | DE69820239T2 (https=) |
| DK (1) | DK0971702T3 (https=) |
| EA (1) | EA001760B1 (https=) |
| ES (1) | ES2210726T3 (https=) |
| FR (1) | FR2759293B1 (https=) |
| HU (1) | HU225425B1 (https=) |
| IL (1) | IL131326A (https=) |
| IN (1) | IN187998B (https=) |
| NO (1) | NO323230B1 (https=) |
| NZ (1) | NZ337216A (https=) |
| PL (1) | PL191631B1 (https=) |
| PT (1) | PT971702E (https=) |
| TW (1) | TW561055B (https=) |
| WO (1) | WO1998034599A1 (https=) |
| ZA (1) | ZA981123B (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050096304A1 (en) * | 1998-09-08 | 2005-05-05 | David White | Method of treating cancer using dithiocarbamate derivatives |
| FR2790668B1 (fr) * | 1999-03-12 | 2002-07-26 | D B F | Granules contenant une substance vegetale et leur procede de preparation |
| BR0010649A (pt) * | 1999-05-17 | 2002-02-19 | D B F | Grãnulos que contêm pelo menos uma substância vegetal e processo de preparação dos mesmos |
| KR101148734B1 (ko) * | 2003-10-10 | 2012-07-05 | 에띠빠흠 | 징코 빌로바 추출물을 포함하는 서방형 미세과립 및 이것을 제조하는 방법 |
| FR2861990B1 (fr) * | 2003-11-10 | 2006-02-10 | Nouveaux Produits Pharma | Comprimes faiblement doses a reseau de polymeres |
| AR052142A1 (es) * | 2004-11-18 | 2007-03-07 | Bristol Myers Squibb Co | Perla recubierta enterica que comprende ixabepilona, y preparacion y administracion de la misma |
| EP1832293A4 (en) * | 2004-12-10 | 2009-01-07 | Tmrc Co Ltd | MEANS FOR THE TREATMENT OF CANCER METASTAS AND CANNESMAS TREATMENT |
| US9107824B2 (en) | 2005-11-08 | 2015-08-18 | Insmed Incorporated | Methods of treating cancer with high potency lipid-based platinum compound formulations administered intraperitoneally |
| FR2918567B1 (fr) * | 2007-07-11 | 2012-08-03 | Pf Medicament | Composition pharmaceutique stable d'un sel hydrosoluble de vinorelbine. |
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| DE3523454A1 (de) * | 1985-07-01 | 1987-01-08 | Eberhard Prof Dr Nuernberg | Formkoerper |
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1997
- 1997-02-11 FR FR9701545A patent/FR2759293B1/fr not_active Expired - Lifetime
-
1998
- 1998-02-10 AT AT98908157T patent/ATE255409T1/de active
- 1998-02-10 DK DK98908157T patent/DK0971702T3/da active
- 1998-02-10 NZ NZ337216A patent/NZ337216A/xx not_active IP Right Cessation
- 1998-02-10 HU HU0001719A patent/HU225425B1/hu not_active IP Right Cessation
- 1998-02-10 DE DE69820239T patent/DE69820239T2/de not_active Expired - Lifetime
- 1998-02-10 EP EP98908157A patent/EP0971702B1/fr not_active Expired - Lifetime
- 1998-02-10 IN IN337DE1998 patent/IN187998B/en unknown
- 1998-02-10 EA EA199900734A patent/EA001760B1/ru not_active IP Right Cessation
- 1998-02-10 BR BR9807319-2A patent/BR9807319A/pt not_active Application Discontinuation
- 1998-02-10 PT PT98908157T patent/PT971702E/pt unknown
- 1998-02-10 KR KR10-1999-7007263A patent/KR100471672B1/ko not_active Expired - Fee Related
- 1998-02-10 TW TW087101722A patent/TW561055B/zh not_active IP Right Cessation
- 1998-02-10 WO PCT/FR1998/000251 patent/WO1998034599A1/fr not_active Ceased
- 1998-02-10 ES ES98908157T patent/ES2210726T3/es not_active Expired - Lifetime
- 1998-02-10 CA CA002282082A patent/CA2282082C/fr not_active Expired - Lifetime
- 1998-02-10 IL IL13132698A patent/IL131326A/xx not_active IP Right Cessation
- 1998-02-10 US US09/367,270 patent/US6458389B1/en not_active Expired - Lifetime
- 1998-02-10 PL PL335107A patent/PL191631B1/pl not_active IP Right Cessation
- 1998-02-10 JP JP53389798A patent/JP4549445B2/ja not_active Expired - Lifetime
- 1998-02-11 ZA ZA981123A patent/ZA981123B/xx unknown
- 1998-02-11 AR ARP980100613A patent/AR011133A1/es active IP Right Grant
-
1999
- 1999-08-10 BG BG103647A patent/BG64247B1/bg unknown
- 1999-08-11 NO NO19993881A patent/NO323230B1/no not_active IP Right Cessation
-
2002
- 2002-07-25 US US10/200,998 patent/US20030017210A1/en not_active Abandoned
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