WO1994012171A1 - Compositions injectables a base de derives des taxanes - Google Patents
Compositions injectables a base de derives des taxanes Download PDFInfo
- Publication number
- WO1994012171A1 WO1994012171A1 PCT/FR1993/001166 FR9301166W WO9412171A1 WO 1994012171 A1 WO1994012171 A1 WO 1994012171A1 FR 9301166 W FR9301166 W FR 9301166W WO 9412171 A1 WO9412171 A1 WO 9412171A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compositions according
- additive
- surfactant
- solution
- chosen
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 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 7
- 239000004094 surface-active agent Substances 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 52
- 239000000243 solution Substances 0.000 claims description 31
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 14
- 230000000996 additive effect Effects 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920000136 polysorbate Polymers 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical group C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- -1 ester ethers Chemical class 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000007972 injectable composition Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229940068965 polysorbates Drugs 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 238000001802 infusion Methods 0.000 abstract description 4
- 239000003978 infusion fluid Substances 0.000 description 7
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 6
- 229940063683 taxotere Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229930012538 Paclitaxel Natural products 0.000 description 5
- 229960001592 paclitaxel Drugs 0.000 description 5
- 239000008389 polyethoxylated castor oil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 description 5
- 239000010413 mother solution Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 229940068968 polysorbate 80 Drugs 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 206010002199 Anaphylactic shock Diseases 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- 0 C[C@](C(C*1)([C@](*)[C@]1C[C@@]1O)[C@]1(C)C([C@@](C(C1(C)C)=C(C)[C@](C2)OC([C@@]([C@@](*)c3ccccc3)O)=O)O*)=O)[C@@]12O Chemical compound C[C@](C(C*1)([C@](*)[C@]1C[C@@]1O)[C@]1(C)C([C@@](C(C1(C)C)=C(C)[C@](C2)OC([C@@]([C@@](*)c3ccccc3)O)=O)O*)=O)[C@@]12O 0.000 description 1
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 229940124650 anti-cancer therapies Drugs 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000011319 anticancer therapy Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Definitions
- the present invention relates to a new pharmaceutical form based on a therapeutic agent having an antitumor and antileukemic activity. It relates more particularly to a new injectable form containing taxoids such as taxol, taxotere or derivatives of the following general formula:
- R represents a hydrogen atom or an acetyl radical
- Ri represents a tert-butoxycarbonylamino or benzoyloxyamino radical.
- R represents an acetyl group and R-
- the first of these two compounds is better known under the name of taxol, the second is known under the name of Taxotere.
- mother solution containing approximately 6 mg / ml of taxol in a solvent mixture composed of:
- this solution When injected, this solution is mixed with an infusion fluid containing sodium chloride or dextrose. To obtain a stable mixture, from both a physical and a chemical point of view, the authors of this article say that the concentration of active ingredient in the infusion solution must be limited to concentrations of approximately 0.03 0.6 mg / ml (see previous publication page 1251 column 1, third paragraph).
- a mother solution was prepared containing the active principle in a mixture of solvents composed of ethanol which is the best biocompatible solvent for the active principles of the class of taxanes and a surfactant chosen from the polysorbates sold in particular under the names Tween and Montanox, or the ether-ether of ethylene oxide and fatty acid glycerides (hydrogenated or non-hydrogenated castor oil) sold for example under the name Cremophor or Emulphor.
- the stock solution was prepared by dissolving the active ingredient in ethanol and then gradually adding the surfactant. It was thus possible to prepare solutions containing 10 to 100 mg / ml of active principle in a mixture containing approximately 50% of surfactant. The ethanol contained in this solution was then removed at least partially by evaporation under vacuum or by any other suitable means.
- the active principle was directly dissolved in the surfactant.
- a surfactant solution containing in particular 1 to 2% of ethanol was prepared and the active principle was continuously added to this solution by stirring using for example a grinder helical or a grinding turbine.
- the presence of a small amount of ethanol provides several advantages, the medium has a lower viscosity, the wetting of the powder is improved as well as the final filtration of the solution.
- the stock solution with a low ethanol content, preferably contains less than 5% of ethanol, it even more preferably contains less than 2% ethanol.
- This solution is stable and can thus contain up to 200 mg / ml and preferably up to 80 mg / ml of active principle in the surfactant.
- the stock solution of taxol had according to this invention a concentration of between 6 and 20 mg / ml of active principle in the surfactant.
- the parent solution of Taxotere preferably had a concentration of between 20 and 80 mg / ml of active principle in the surfactant.
- Another solution for dissolving the mother solution in the infusion solution consists in heating the whole to around 40 ° C. But in this case, the compound of formula (I) is partially degraded
- the present invention therefore consists in producing an intermediate solution between the solution of derivatives of the taxane class in the surfactant and an aqueous solution containing an additive subsequently promoting the dissolution of said intermediate solution in the infusion solution.
- additives are chosen from all of the additives which are capable of breaking or avoiding the formation of the gelled phase which is formed between the emulsifier containing the derivative of the taxane class and water.
- additives making it possible to break or avoid the formation of this gelled phase
- derivatives having a molecular weight equal to or less than about 200.
- these compounds those more preferred are those which carry at least one hydroxyl function or an amino function such as amino acids.
- Mineral salts such as sodium chloride can also be used.
- the amount of additive used varies depending on the nature of the additive, it is preferably greater than 6% by weight relative to the mass of surfactant and even more preferably greater than 15% by weight for the polyols such than glycerol, glucose or sorbitol.
- solutions of the taxoids in the surfactant with the aqueous solution of the dilution additive are preferably presented in ampoules, vials or a double-compartment device allowing the extemporaneous mixing of the two solutions at the time of injection into the infusion bag.
- Taxotere or taxol infusions are then injected into humans at a predetermined rate depending on the amount of active ingredient that one wants to inject. We do not observe with these solutions the phenomena of anaphylactic shocks that we observed with the solutions of the prior art. Thus these last infusions have made it possible to reduce, compared to the prior art, the amounts of surfactant injected into humans by approximately 80%.
- the solution obtained is stable, it contains 40 mg / ml of Taxotere.
- Example 1 is repeated, replacing the glycerol solution with an aqueous glucose solution containing 35% by weight of glucose. After manual stirring, the solution is fluid.
- EXAMPLES 3 to 4 are repeated, replacing the glycerol solution with an aqueous glucose solution containing 35% by weight of glucose. After manual stirring, the solution is fluid.
- Example 1 is reproduced, replacing the Polysorbate with different surfactants the results are shown in the following table:
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Epoxy Compounds (AREA)
- Detergent Compositions (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL93309197A PL174334B1 (pl) | 1992-12-02 | 1993-11-26 | Sposób wytwarzania kompozycji do iniekcji zawierającej pochodne z grupy taksanów przeznaczonej do przygotowania roztworu do perfuzji |
| AT94900881T ATE190838T1 (de) | 1992-12-02 | 1993-11-26 | Injizierbare arzneizubereitungen enthaltend taxanderivate |
| HU9501596A HU222833B1 (hu) | 1992-12-02 | 1993-11-26 | Taxánszármazékot tartalmazó injektálható gyógyszerkészítmények |
| DK94900881T DK0671912T3 (da) | 1992-12-02 | 1993-11-26 | Injicerbare præparater baseret på taxanderivater |
| CA002150576A CA2150576C (fr) | 1992-12-02 | 1993-11-26 | Compositions injectables a base de derives des taxanes |
| DE69328192A DE69328192D1 (de) | 1992-12-02 | 1993-11-26 | Injizierbare Arzneizubereitungen enthaltend Taxanderivate |
| RU95113494A RU2144356C1 (ru) | 1992-12-02 | 1993-11-26 | Композиция для инъекций на основе таксоидов |
| KR1019950702223A KR100330316B1 (ko) | 1992-12-02 | 1993-11-26 | 탁산유도체를기재로한주사용조성물 |
| DE69328192T DE69328192T4 (de) | 1992-12-02 | 1993-11-26 | Injizierbare Arzneizubereitungen enthaltend Taxanderivate |
| SK725-95A SK281558B6 (sk) | 1992-12-02 | 1993-11-26 | Injikovateľná kompozícia na prípravu infúzneho roztoku obsahujúca deriváty skupiny taxánov |
| JP50090394A JP3689791B2 (ja) | 1992-12-02 | 1993-11-26 | タキソイドに基づく新規な組成物 |
| AU55669/94A AU691476B2 (en) | 1992-12-02 | 1993-11-26 | Injectable taxane derivative based compositions |
| EP94900881A EP0671912B1 (fr) | 1992-12-02 | 1993-11-26 | Compositions injectables a base de derives des taxanes |
| NO19952151A NO314436B1 (no) | 1992-12-02 | 1995-05-31 | Injiserbare, taxanderivat-baserte preparater |
| FI952680A FI113619B (fi) | 1992-12-02 | 1995-06-01 | Menetelmä injektoitavien taksaanijohdannaisiin pohjautuvien koostumusten valmistamiseksi |
| GR990401833T GR3032828T3 (en) | 1992-12-02 | 2000-03-23 | Injectable taxane derivative based compositions. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR92/14501 | 1992-12-02 | ||
| FR9214501A FR2698543B1 (fr) | 1992-12-02 | 1992-12-02 | Nouvelles compositions à base de taxoides. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1994012171A1 true WO1994012171A1 (fr) | 1994-06-09 |
Family
ID=9436137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR1993/001166 WO1994012171A1 (fr) | 1992-12-02 | 1993-11-26 | Compositions injectables a base de derives des taxanes |
Country Status (28)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997041850A1 (en) * | 1996-05-02 | 1997-11-13 | Yeong Wook Song | Paclitaxel for the treatment of rheumatic diseases |
| WO1998053810A1 (en) * | 1997-05-30 | 1998-12-03 | Man Woo Han | Pharmaceutical injection solution containing taxol |
| WO1998057630A1 (fr) * | 1997-06-13 | 1998-12-23 | Laboratoires Thissen (L.T.B.) | Forme pharmaceutique pour l'administration de paclitaxel, procede de preparation d'une composition de paclitaxel prete a l'emploi et utilisation de cette composition |
| EP0876145A4 (en) * | 1995-12-21 | 1999-04-21 | Genelabs Tech Inc | TAX COMPOSITION AND PROCEDURE |
| EP0920311A4 (en) * | 1996-06-28 | 2001-10-04 | Univ Texas | PACLITAXEL PARENTERAL IN A STABLE NON-TOXIC FORMULATION |
| DE19655141B4 (de) | 1996-11-08 | 2005-04-07 | Eppendorf Ag | Gradienten-Temperierblock für Laborthermostaten |
Families Citing this family (114)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5716981A (en) * | 1993-07-19 | 1998-02-10 | Angiogenesis Technologies, Inc. | Anti-angiogenic compositions and methods of use |
| DK2226085T3 (da) | 1993-07-19 | 2014-02-03 | Angiotech Pharm Inc | Anti-angiogene sammensætninger samt fremgangsmåder til anvendelse deraf |
| US5681846A (en) * | 1995-03-17 | 1997-10-28 | Board Of Regents, The University Of Texas System | Extended stability formulations for paclitaxel |
| US6395770B1 (en) * | 1995-10-26 | 2002-05-28 | Baker Norton Pharmaceuticals, Inc. | Method and compositions for administering taxanes orally to human patients |
| US6964946B1 (en) | 1995-10-26 | 2005-11-15 | Baker Norton Pharmaceuticals, Inc. | Oral pharmaceutical compositions containing taxanes and methods of treatment employing the same |
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