WO1994012198A1 - Composition a base de taxol injectable - Google Patents
Composition a base de taxol injectable Download PDFInfo
- Publication number
- WO1994012198A1 WO1994012198A1 PCT/AU1993/000599 AU9300599W WO9412198A1 WO 1994012198 A1 WO1994012198 A1 WO 1994012198A1 AU 9300599 W AU9300599 W AU 9300599W WO 9412198 A1 WO9412198 A1 WO 9412198A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- solution
- taxol
- injectable
- composition according
- Prior art date
Links
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
- A61K9/0012—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
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides 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
- A61K47/44—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
Definitions
- Taxol is a compound extracted from the bark of a western yew, Taxus brev ⁇ folxa and known for its antineoplastic activity. It is described for example in the Merck Index, Eleventh Edition 1989, monograph 9049.
- taxol was chosen for development as an antineoplastic agent because of its unique mechanism of action and good cytotoxic activity against IP. implanted bl6 melanoma and the human MX-1 mammary tumor xenograft. Taxol is believed to function as a mitotic spindle poison and as a potent inhibitor of cell replication in vitro. Other mitotic spindle poisons (colchicine and podophyllotoxin) inhibit microtubule assembly. Taxol employs a different mechanism of action since it appears to shift the equilibrium of polymerization/depolymerization toward polymer assembly and to stabilize microtubules against depolymerization under conditions which would cause rapid disaggregation of microtubules.
- taxol entered clinical trials in 1983. Over the past few years, taxol has demonstrated good response rates in treating both ovarian and breast cancer patients who were not benefiting from vinca alkaloid or cisplatin therapy. It has also shown encouraging results in patients with other types of cancer including lung, melanoma, lymphoma, head and neck.
- NCI National Cancer Institute
- a known formulation contains taxol, cremophor EL (a polyethoxylated castor oil which acts as a solubilizer) and ethanol. It is a disadvantage of the known formulation that the taxol therein degrades, unless stored at or below 8°C, with the result that the shelf life of the formulation is unsatisfactory, and there is therefore a need for a taxol solution of improved stability.
- cremophor EL a polyethoxylated castor oil which acts as a solubilizer
- the invention provides a solution containing taxol, a pharmaceutically acceptable solubilising agent (for example a polyethoxylated castor oil), and a pharmaceutically acceptable organic solvent (such as ethanol), characterized in that the pH of the solution has been adjusted to a pH less than 8.1, preferably into the range 1 to 8 by addition of an acid.
- a pharmaceutically acceptable solubilising agent for example a polyethoxylated castor oil
- a pharmaceutically acceptable organic solvent such as ethanol
- Acids in the form of powders for example citric acid, are preferred over those which contain water, for example sulphuric acid.
- the most preferred acid for use in accordance with the present invention is anhydrous citric acid but a wide range of acids may be used including the following: Citric acid - Monohydrous
- taxol Due to its limited solubility in water, taxol is usually prepared and administered in a vehicle containing cremophor EL (a polyethoxylated castor oil which acts as a solubiliser) and ethanol.
- a solution prepared by the formulation as stated in the NCI Taxol Clinical brochure has a pH of 9.1.
- the invention essentially teaches addition of an acid to a taxol formulation to adjust its pH into the range below 8.1, preferably 1 to 8, and more preferably 5 to 7.5.
- Citric acid was dissolved in ethanol (absolute alcohol), using a ratio of 8 mis of absolute alcohol to 1 gram of citric acid, and the solution was stirred for fifteen (15) minutes.
- Cremophor EL was weighed out into the main mixing vessel.
- Solution 1 was added to solution 2, and the container used for solution 2 was washed with a minimum quantity of absolute alcohol to ensure complete transfer of the citric acid.
- Solution 3 was mixed and bubbled with nitrogen for at least 15 minutes.
- the taxol was weighed out and slurried using absolute alcohol, using a ratio of 8 ml of absolute alcohol to 1 gm of taxol.
- the slurried taxol was added to solution 3 and the slurrying vessel was washed with a minimum quantity of absolute alcohol.
- Solution 3 was adjusted to 75% of required volume using absolute alcohol, and thoroughly stirred for at least 45 minutes until completely dissolved. Once completely dissolved, the volume was made up with absolute alcohol and the final solution stirred for 5 minutes.
- Citric Acid (Anhydrous) 2.O g Taxol 6.Omg Absolute Alcohol to 1.0OmL
- Cremophor EL 0.5mL Taxol 6mg
- the solution was filled into clear type 1 glass 5mL vials and sealed with rubber bungs.
- the solution was stored at 40°C for 7 days.
- citric acid which is preferably used in the anhydrous form, at pH 5 to 7.5, the formulation at pH 6.1 showing the lowest levels for both total and individual major impurities.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU55538/94A AU5553894A (en) | 1992-11-27 | 1993-11-25 | Injectable taxol composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPL607492 | 1992-11-27 | ||
AUPL6074 | 1992-11-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994012198A1 true WO1994012198A1 (fr) | 1994-06-09 |
Family
ID=3776561
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/AU1993/000599 WO1994012198A1 (fr) | 1992-11-27 | 1993-11-25 | Composition a base de taxol injectable |
Country Status (8)
Country | Link |
---|---|
KR (1) | KR100371062B1 (fr) |
CN (2) | CN1096673A (fr) |
AU (1) | AU5553894A (fr) |
IL (2) | IL107776A0 (fr) |
IN (1) | IN176188B (fr) |
NZ (1) | NZ258044A (fr) |
WO (1) | WO1994012198A1 (fr) |
ZA (1) | ZA938844B (fr) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2710534A1 (fr) * | 1994-09-28 | 1995-04-07 | Bristol Myers Squibb Co | Solvant de stabilisation, composition pharmaceutique le contenant, et son procédé de préparation. |
EP0674510A4 (fr) * | 1992-11-27 | 1995-08-12 | Napro Biotherapeutics Inc | Composition injectable. |
NL9500340A (nl) * | 1995-02-22 | 1996-10-01 | Yew Tree Pharmaceuticals B V | Gestabiliseerde paclitaxel-oplossing en farmaceutisch preparaat dat deze oplossing bevat. |
ES2095802A1 (es) * | 1993-09-29 | 1997-02-16 | Bristol Myers Squibb Co | Composicion farmaceutica estabilizada y solvente de estabilizacion. |
US5686488A (en) * | 1995-08-25 | 1997-11-11 | Alcon Laboratories, Inc. | Polyethoxylated castor oil products as anti-inflammatory agents |
WO1997041850A1 (fr) * | 1996-05-02 | 1997-11-13 | Yeong Wook Song | Paclitaxel pour le traitement d'affections rhumatismales |
EP0876145A1 (fr) * | 1995-12-21 | 1998-11-11 | Genelabs Technologies, Inc. | Composition de taxane et procede s'y rapportant |
WO1998053810A1 (fr) * | 1997-05-30 | 1998-12-03 | Man Woo Han | Solution pharmaceutique injectable contenant du 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 |
US6045808A (en) * | 1997-01-31 | 2000-04-04 | Pharmacia & Upjohn Company | Method for removing high boiling solvents from drug formulations by vacuum drying |
WO2000032186A2 (fr) * | 1998-12-02 | 2000-06-08 | Mylan Pharmaceuticals, Inc. | Compositions pharmaceutiques injectables stabilisees contenant des agents anti-neoplastiques taxoides |
KR100330373B1 (ko) * | 1996-05-28 | 2002-11-07 | 주식회사한국신약 | 탁솔을 함유한 주사용 약제 조성물 |
KR100358934B1 (ko) * | 1996-09-13 | 2003-01-29 | 주식회사한국신약 | 탁솔을함유한주사용약제조성물 |
WO2003022247A1 (fr) * | 2001-09-10 | 2003-03-20 | Choongwae Pharma Corporation | Composition injectable de paclitaxel |
US6919370B2 (en) | 2000-11-28 | 2005-07-19 | Transform Pharmaceuticals, Inc. | Pharmaceutical formulations comprising paclitaxel, derivatives, and pharmaceutically acceptable salts thereof |
JP2005534656A (ja) * | 2002-06-10 | 2005-11-17 | プリヴァ−ラチェマ アー.エス. | ポリオキシエチル化ひまし油に基づく安定化医薬組成物およびその製造方法 |
EP1904052A1 (fr) * | 2005-06-17 | 2008-04-02 | Hospira Australia Pty Ltd | Compositions pharmaceutiques liquides de docétaxel |
JP2012072188A (ja) * | 2002-06-26 | 2012-04-12 | Medigene Ag | 脂肪親和性化合物を含む陽イオン性リポソームの製法 |
US9308180B2 (en) | 2005-08-31 | 2016-04-12 | Abraxis Bioscience, Llc | Compositions and methods for preparation of poorly water soluble drugs with increased stability |
US11529441B2 (en) | 2015-09-15 | 2022-12-20 | W. L. Gore & Associates, Inc. | Drug composition and coating |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19536165A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren zur Reinigung von alkoxylierten Fetten |
CN1101677C (zh) * | 1997-05-30 | 2003-02-19 | 韩万愚 | 含有紫杉醇的药用注射溶液 |
DE10115740A1 (de) * | 2001-03-26 | 2002-10-02 | Ulrich Speck | Zubereitung für die Restenoseprophylaxe |
CN101396354B (zh) * | 2007-09-30 | 2010-12-01 | 江苏恒瑞医药股份有限公司 | 一种稳定的塔三烷类化合物液体组合物及其制备方法和其应用 |
CN101829051B (zh) * | 2010-05-31 | 2012-09-12 | 南昌弘益科技有限公司 | 1’-乙酰氧基胡椒酚乙酸酯注射液 |
CN103432109B (zh) * | 2013-09-01 | 2015-09-23 | 吴静 | 紫杉醇的药物组合物 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1990010443A1 (fr) * | 1989-03-09 | 1990-09-20 | University Of Kansas | Derives de taxol, leurs compositions pharmaceutiques et leurs procedes de preparation |
EP0428376A1 (fr) * | 1989-11-14 | 1991-05-22 | Florida State University | Procédé pour la préparation du taxol utilisant une oxazinone |
EP0505047A1 (fr) * | 1991-03-18 | 1992-09-23 | Virginia Tech Intellectual Properties, Inc. | Dérivés de Taxol redisposés et procédé d'utilisation dans l'essai d'activité in vivo |
US5157049A (en) * | 1988-03-07 | 1992-10-20 | The United States Of America As Represented By The Department Of Health & Human Services | Method of treating cancers sensitive to treatment with water soluble derivatives of taxol |
AU1888792A (en) * | 1991-04-19 | 1992-11-17 | University Of Mississippi, The | Methods and compositions for isolating taxanes |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
NZ224497A (en) * | 1987-05-18 | 1990-04-26 | Janssen Pharmaceutica Nv | Pharmaceutical composition comprising flunarizine |
-
1993
- 1993-11-25 KR KR1019940702575A patent/KR100371062B1/ko not_active IP Right Cessation
- 1993-11-25 NZ NZ258044A patent/NZ258044A/en not_active IP Right Cessation
- 1993-11-25 WO PCT/AU1993/000599 patent/WO1994012198A1/fr active Application Filing
- 1993-11-25 AU AU55538/94A patent/AU5553894A/en not_active Abandoned
- 1993-11-26 IL IL10777693A patent/IL107776A0/xx not_active IP Right Cessation
- 1993-11-26 ZA ZA938844A patent/ZA938844B/xx unknown
- 1993-11-26 IN IN730CA1993 patent/IN176188B/en unknown
- 1993-11-26 CN CN93115293A patent/CN1096673A/zh active Pending
- 1993-11-27 CN CN93120529A patent/CN1047305C/zh not_active Expired - Fee Related
-
1998
- 1998-09-10 IL IL12617898A patent/IL126178A0/xx unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5157049A (en) * | 1988-03-07 | 1992-10-20 | The United States Of America As Represented By The Department Of Health & Human Services | Method of treating cancers sensitive to treatment with water soluble derivatives of taxol |
WO1990010443A1 (fr) * | 1989-03-09 | 1990-09-20 | University Of Kansas | Derives de taxol, leurs compositions pharmaceutiques et leurs procedes de preparation |
EP0428376A1 (fr) * | 1989-11-14 | 1991-05-22 | Florida State University | Procédé pour la préparation du taxol utilisant une oxazinone |
EP0505047A1 (fr) * | 1991-03-18 | 1992-09-23 | Virginia Tech Intellectual Properties, Inc. | Dérivés de Taxol redisposés et procédé d'utilisation dans l'essai d'activité in vivo |
AU1888792A (en) * | 1991-04-19 | 1992-11-17 | University Of Mississippi, The | Methods and compositions for isolating taxanes |
Cited By (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6306894B1 (en) | 1992-11-27 | 2001-10-23 | Napro Biotherapeutics, Inc. | Injectable composition |
EP0674510A4 (fr) * | 1992-11-27 | 1995-08-12 | Napro Biotherapeutics Inc | Composition injectable. |
EP0674510A1 (fr) * | 1992-11-27 | 1995-10-04 | Napro Biotherapeutics, Inc. | Composition injectable |
US6140359A (en) * | 1992-11-27 | 2000-10-31 | Napro Biotherapeutics, Inc. | Injectable composition |
EP1500393A1 (fr) * | 1992-11-27 | 2005-01-26 | Mayne Pharma (USA) Inc. | Composition injectable de taxol |
EP1384474A1 (fr) * | 1992-11-27 | 2004-01-28 | Napro Biotherapeutics, Inc. | Composition injectable de taxol |
US5977164A (en) * | 1992-11-27 | 1999-11-02 | Napro Biotherapeutics, Inc. | Stabilized pharmaceutical composition |
EP0835657A1 (fr) * | 1992-11-27 | 1998-04-15 | Napro Biotherapeutics, Inc. | Composition injectable |
US5972992A (en) * | 1992-11-27 | 1999-10-26 | Napro Biotherapeutics, Inc. | Injectable composition |
ES2095802A1 (es) * | 1993-09-29 | 1997-02-16 | Bristol Myers Squibb Co | Composicion farmaceutica estabilizada y solvente de estabilizacion. |
FR2710534A1 (fr) * | 1994-09-28 | 1995-04-07 | Bristol Myers Squibb Co | Solvant de stabilisation, composition pharmaceutique le contenant, et son procédé de préparation. |
NL9500340A (nl) * | 1995-02-22 | 1996-10-01 | Yew Tree Pharmaceuticals B V | Gestabiliseerde paclitaxel-oplossing en farmaceutisch preparaat dat deze oplossing bevat. |
US5686488A (en) * | 1995-08-25 | 1997-11-11 | Alcon Laboratories, Inc. | Polyethoxylated castor oil products as anti-inflammatory agents |
EP0876145A4 (fr) * | 1995-12-21 | 1999-04-21 | Genelabs Tech Inc | Composition de taxane et procede s'y rapportant |
EP0876145A1 (fr) * | 1995-12-21 | 1998-11-11 | Genelabs Technologies, Inc. | Composition de taxane et procede s'y rapportant |
WO1997041850A1 (fr) * | 1996-05-02 | 1997-11-13 | Yeong Wook Song | Paclitaxel pour le traitement d'affections rhumatismales |
KR100330373B1 (ko) * | 1996-05-28 | 2002-11-07 | 주식회사한국신약 | 탁솔을 함유한 주사용 약제 조성물 |
KR100358934B1 (ko) * | 1996-09-13 | 2003-01-29 | 주식회사한국신약 | 탁솔을함유한주사용약제조성물 |
US6045808A (en) * | 1997-01-31 | 2000-04-04 | Pharmacia & Upjohn Company | Method for removing high boiling solvents from drug formulations by vacuum drying |
WO1998053810A1 (fr) * | 1997-05-30 | 1998-12-03 | Man Woo Han | Solution pharmaceutique injectable contenant du taxol |
BE1011216A3 (fr) * | 1997-06-13 | 1999-06-01 | Thissen En Abrege L T B Lab | Forme pharmaceutique pour l'administration de paclitaxel, procede de preparation d'une composition de paclitaxel prete a l'emploi et utilisation de cette composition. |
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 |
WO2000032186A3 (fr) * | 1998-12-02 | 2000-11-16 | Mylan Pharmaceuticals Inc | Compositions pharmaceutiques injectables stabilisees contenant des agents anti-neoplastiques taxoides |
WO2000032186A2 (fr) * | 1998-12-02 | 2000-06-08 | Mylan Pharmaceuticals, Inc. | Compositions pharmaceutiques injectables stabilisees contenant des agents anti-neoplastiques taxoides |
US6919370B2 (en) | 2000-11-28 | 2005-07-19 | Transform Pharmaceuticals, Inc. | Pharmaceutical formulations comprising paclitaxel, derivatives, and pharmaceutically acceptable salts thereof |
US7186751B2 (en) | 2001-09-10 | 2007-03-06 | Choongwae Pharma Corporation | Injectable composition of paclitaxel |
KR100774366B1 (ko) * | 2001-09-10 | 2007-11-08 | 주식회사 중외제약 | 파클리탁셀 주사제 조성물 |
WO2003022247A1 (fr) * | 2001-09-10 | 2003-03-20 | Choongwae Pharma Corporation | Composition injectable de paclitaxel |
JP2005534656A (ja) * | 2002-06-10 | 2005-11-17 | プリヴァ−ラチェマ アー.エス. | ポリオキシエチル化ひまし油に基づく安定化医薬組成物およびその製造方法 |
JP2012072188A (ja) * | 2002-06-26 | 2012-04-12 | Medigene Ag | 脂肪親和性化合物を含む陽イオン性リポソームの製法 |
EP1904052A1 (fr) * | 2005-06-17 | 2008-04-02 | Hospira Australia Pty Ltd | Compositions pharmaceutiques liquides de docétaxel |
EP2138164A1 (fr) * | 2005-06-17 | 2009-12-30 | Hospira Australia Pty Ltd | Formulations pharmaceutiques liquide comprenant du docétaxel |
EP2308467A3 (fr) * | 2005-06-17 | 2011-06-22 | Hospira Australia Pty Ltd | Compositions Pharmaceutiques Liquides de Docétaxel |
EP1904052A4 (fr) * | 2005-06-17 | 2008-12-10 | Hospira Australia Pty Ltd | Compositions pharmaceutiques liquides de docétaxel |
US9308180B2 (en) | 2005-08-31 | 2016-04-12 | Abraxis Bioscience, Llc | Compositions and methods for preparation of poorly water soluble drugs with increased stability |
US11529441B2 (en) | 2015-09-15 | 2022-12-20 | W. L. Gore & Associates, Inc. | Drug composition and coating |
Also Published As
Publication number | Publication date |
---|---|
CN1096673A (zh) | 1994-12-28 |
CN1047305C (zh) | 1999-12-15 |
CN1095266A (zh) | 1994-11-23 |
IN176188B (fr) | 1996-02-24 |
AU667142B2 (en) | 1996-03-07 |
KR100371062B1 (ko) | 2003-04-21 |
ZA938844B (en) | 1994-08-02 |
NZ258044A (en) | 1995-12-21 |
AU5553894A (en) | 1994-06-22 |
AU5196793A (en) | 1994-06-09 |
IL107776A0 (en) | 1994-02-27 |
IL126178A0 (en) | 1999-05-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5972992A (en) | Injectable composition | |
WO1994012198A1 (fr) | Composition a base de taxol injectable | |
AU724842B2 (en) | Taxane composition and method | |
HU217839B (hu) | Eljárások taxánszármazékokat tartalmazó új stabil gyógyszerkészítmények előállítására | |
AU2002361701A1 (en) | Pharmaceutical compositons of orally active taxane derivatives having enhanced bioavailability | |
US6017948A (en) | Water-miscible pharmaceutical compositions | |
EP0605753B1 (fr) | Complexe d'inclusion du taxol, procédé pour sa préparation et utilisation | |
AU2002351169B2 (en) | Method for preparing and using polyoxyethylated castor oil in pharmaceutical compositions | |
EP2306976A2 (fr) | Composition pharmaceutique de taxane injectable | |
KR980008219A (ko) | 안정화된 주사제용 약제학적 조성물 | |
JP6292267B2 (ja) | ドセタキセル製剤 | |
EP0236280B1 (fr) | Formulations pharmaceutiques injectables de principes actifs à activité anesthésique générale | |
JP3748912B2 (ja) | オーレオバシジン類の高濃度溶液製剤 | |
RU2279873C2 (ru) | Пероральная фармацевтическая композиция для мягких капсул, содержащая винорелбин, и способ лечения | |
JP2018115178A (ja) | ドセタキセル製剤 | |
WO2005044257A1 (fr) | Compositions de discodermolide | |
WO2005074889A1 (fr) | Nouvelles compositions de derives de taxol et procede de fabrication associe |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AT AU BB BG BR BY CA CH CZ DE DK ES FI GB HU JP KP KR KZ LK LU LV MG MN MW NL NO NZ PL PT RO RU SD SE SK UA UZ VN |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG |
|
WWE | Wipo information: entry into national phase |
Ref document number: 258044 Country of ref document: NZ |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1019940702575 Country of ref document: KR |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
122 | Ep: pct application non-entry in european phase | ||
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
NENP | Non-entry into the national phase |
Ref country code: CA |