CA2294031C - Self-emulsifying formulation for lipophilic compounds - Google Patents
Self-emulsifying formulation for lipophilic compounds Download PDFInfo
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- CA2294031C CA2294031C CA002294031A CA2294031A CA2294031C CA 2294031 C CA2294031 C CA 2294031C CA 002294031 A CA002294031 A CA 002294031A CA 2294031 A CA2294031 A CA 2294031A CA 2294031 C CA2294031 C CA 2294031C
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- diglyceride
- monoglyceride
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- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4433—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
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- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Bioinformatics & Cheminformatics (AREA)
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- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biophysics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Silicon Polymers (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention provides a novel pharmaceutical composition based on the use of a particular oil phase which comprises a lipophilic, pharmaceutically active agent, a mixture of diglyceride and monoglyceride in a ratio of from about 9:1 to about 6:4 by weight (diglyceride:monoglyceride) wherein the diglyceride and monoglyceride are mono-or di-unsaturated fatty acid esters of glycerol having sixteen to twenty-two carbon chain length, one or more pharmaceutically acceptable solvents, and one or more pharmaceutically acceptable surfactants. The composition is in a form of self-emulsifying formulation which provides high concentration and high oral bioavailability for lipophilic compounds.
Claims (39)
1. A pharmaceutical composition comprising;
(a) a lipophilic, pharmaceutically active agent, (b) a mixture consisting essentially of diglyceride and monoglyceride in a ratio of from about 9:1 to about 6:4 by weight (diglyceride:monoglyceride) wherein the diglyceride and monoglyceride are mono- or di-unsaturated fatty acid esters of glycerol having sixteen to twenty-two carbon chain length, (c) one or more pharmaceutically acceptable solvents, and (d) one or more pharmaceutically acceptable surfactants; wherein the solvent is propylene glycol, polypropylene glycol, polyethylene glycol, glycerol, ethanol, dimethyl isosorbide, glycofurol, propylene carbonate, dimethyl acetamide, or a mixture thereof; wherein said surfactant is Polyoxyl 40 hydrogenated castor oil, Polyoxyl 35 castor oil, polyethylene glycol 12-hydroxy stearate, polyoxyethylene glyceryl trioleate, Peglicol 6-oleate, Polyoxyethylene stearates, Poloxamers, Polysorbates, or Saturated Polyglycolyzed Glycerides; with the proviso that said lipophilic, pharmaceutically active agent has a LOG P value >=2, an intrinsic aqueous solubility <=0.1 in the pH range of 1 to 8 and a solubility greater than 1 mg/ml in the mixture of b, c and d as defined herein.
(a) a lipophilic, pharmaceutically active agent, (b) a mixture consisting essentially of diglyceride and monoglyceride in a ratio of from about 9:1 to about 6:4 by weight (diglyceride:monoglyceride) wherein the diglyceride and monoglyceride are mono- or di-unsaturated fatty acid esters of glycerol having sixteen to twenty-two carbon chain length, (c) one or more pharmaceutically acceptable solvents, and (d) one or more pharmaceutically acceptable surfactants; wherein the solvent is propylene glycol, polypropylene glycol, polyethylene glycol, glycerol, ethanol, dimethyl isosorbide, glycofurol, propylene carbonate, dimethyl acetamide, or a mixture thereof; wherein said surfactant is Polyoxyl 40 hydrogenated castor oil, Polyoxyl 35 castor oil, polyethylene glycol 12-hydroxy stearate, polyoxyethylene glyceryl trioleate, Peglicol 6-oleate, Polyoxyethylene stearates, Poloxamers, Polysorbates, or Saturated Polyglycolyzed Glycerides; with the proviso that said lipophilic, pharmaceutically active agent has a LOG P value >=2, an intrinsic aqueous solubility <=0.1 in the pH range of 1 to 8 and a solubility greater than 1 mg/ml in the mixture of b, c and d as defined herein.
2. The pharmaceutical composition of claim 1 wherein the lipophilic, pharmaceutically active agent is selected from the group consisting of Medroxyprogesterone Acetate, Progesterone, Testosterone, Troglitazone, Pioglitazone, Glyburide, Ketoconazole, Itraconazole, Camptothecin, (4S)4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':
6,7]indolizino[1,2-b]quinoline-
6,7]indolizino[1,2-b]quinoline-
3,14(4H,12H)- dione, Irinotecan hydrochloride, Paclitaxel, Docetaxel, 2aR-[2a.alpha.,4a.beta.,6.beta.,7.beta.,9 (.alpha.R*, .beta.S*),11.alpha., 12.alpha.,12a.alpha.,12b.alpha.]]-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,4a,5,6,7,10,11,12, 12a, 12b-decahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz [1,2-b]oxet-9-yl (3-[[[(1,1-dimethylethyl)amino]carbonyl]
amino]-a-hydroxy benzenepropanoate, (1S,2S,3R,4S,7R,10R,12R)-4,12-bis(acetyloxy)-15-[((2R,3S)-3-{[(tert-butylamino)carbonyl] amino]-2-hydroxy-3-phenylpropanoyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6- oxatetracyclo[11.3.1.03.10.04.7 ]heptadeca-8,14-dien-2-yl benzoate, PGE2.alpha., PGE1, PGE2, Delavirdine mesylate, Vitamin E, Tirilazad Mesylate, Griseofulvin, Phenytoin, Ibuprofen, Flurbiprofen, 1-[(2,4-di(1-pyrrolidinyl)-9H-pyrimido[4,5-b]-yl]indol-9-ylacetyl]-1-(1-pyrrolidine), 2-[2,4-di(1-pyrrolidinyl)-9H-pyrimido[4,5-b)indol-9-yl]-1-(1-pyrrolidinyl)-1-ethanone, (S)-1-[2-[4-[4-(aminocarbonyl)phenyl]-1-piperazinyl]ethyl]-3,4-dihydro-N-methyl-1 H-2-benzopyran-6-carboxamide, 1H-2-benzopyran-6-carboxamide, 1-[2-[4-[4-(aminocarbonyl) phenyl]-piperazinyl]ethyl]-3,4-dihydro-N-methyl-, (S)- or (1S)-1-(2-{4-[4-(aminocarbonyl) phenyl]-1-piperazinyl}ethyl)-N-methyl-3,4-dihydro-1 H-isochromene-6-carboxamide, (-)-6-chloro-2-[(1-furo[2,3-c]pyridin-5-ylethyl)thio]-4-pyrimidinamine, and 6-chloro-2-f [(1S)-1-furo[2,3-c]pyridin-5-ylethyl]sulfonyl}-4-pyrimidinylamine.
3. The pharmaceutical composition of claim 1 wherein the lipophilic, pharmaceutically active agent is Irinotecan hydrochloride.
amino]-a-hydroxy benzenepropanoate, (1S,2S,3R,4S,7R,10R,12R)-4,12-bis(acetyloxy)-15-[((2R,3S)-3-{[(tert-butylamino)carbonyl] amino]-2-hydroxy-3-phenylpropanoyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6- oxatetracyclo[11.3.1.03.10.04.7 ]heptadeca-8,14-dien-2-yl benzoate, PGE2.alpha., PGE1, PGE2, Delavirdine mesylate, Vitamin E, Tirilazad Mesylate, Griseofulvin, Phenytoin, Ibuprofen, Flurbiprofen, 1-[(2,4-di(1-pyrrolidinyl)-9H-pyrimido[4,5-b]-yl]indol-9-ylacetyl]-1-(1-pyrrolidine), 2-[2,4-di(1-pyrrolidinyl)-9H-pyrimido[4,5-b)indol-9-yl]-1-(1-pyrrolidinyl)-1-ethanone, (S)-1-[2-[4-[4-(aminocarbonyl)phenyl]-1-piperazinyl]ethyl]-3,4-dihydro-N-methyl-1 H-2-benzopyran-6-carboxamide, 1H-2-benzopyran-6-carboxamide, 1-[2-[4-[4-(aminocarbonyl) phenyl]-piperazinyl]ethyl]-3,4-dihydro-N-methyl-, (S)- or (1S)-1-(2-{4-[4-(aminocarbonyl) phenyl]-1-piperazinyl}ethyl)-N-methyl-3,4-dihydro-1 H-isochromene-6-carboxamide, (-)-6-chloro-2-[(1-furo[2,3-c]pyridin-5-ylethyl)thio]-4-pyrimidinamine, and 6-chloro-2-f [(1S)-1-furo[2,3-c]pyridin-5-ylethyl]sulfonyl}-4-pyrimidinylamine.
3. The pharmaceutical composition of claim 1 wherein the lipophilic, pharmaceutically active agent is Irinotecan hydrochloride.
4. The pharmaceutical composition of claim 1 wherein the lipophilic, pharmaceutically active agent is in an amount of from about 1 % to about 40% by weight of the total composition.
5. The pharmaceutical composition of claim 1 wherein the lipophilic, pharmaceutically active agent is in an amount of from about 5% to about 30% by weight of the total composition.
6. The pharmaceutical composition of claim 1 wherein said diglyceride is diolein, dilinoleate or a mixture thereof.
7. The pharmaceutical composition of claim 1 wherein said diglyceride is diolein.
8. The pharmaceutical composition of claim 1 wherein said monoglyceride is monoolein, monolinoleate or a mixture thereof.
9. The pharmaceutical composition of claim 1 wherein said monoglyceride is monoolein.
10. The pharmaceutical composition of claim 1 wherein the mixture of diglyceride and monoglyceride is in an amount of from about 5% to about 40% by weight of the total composition.
11. The pharmaceutical composition of claim 1 wherein the mixture of diglyceride and monoglyceride is in an amount of from about 5% to about 35% by weight of the total composition.
12. The pharmaceutical composition of claim 1 wherein the mixture of diglyceride and monoglyceride is in a ratio of about 8:2 by weight (diglyceride:monoglyceride).
13. The pharmaceutical composition of claim 1 wherein the mixture of diglyceride and monoglyceride is in a ratio of about 9:1 by weight (diglyceride:monoglyceride).
14. The pharmaceutical composition of claim 1 wherein the pharmaceutically acceptable solvent is propylene glycol.
15. The pharmaceutical composition of claim 1 wherein the pharmaceutically acceptable solvent is a mixture comprising propylene glycol and 95% (v/v) ethanol in a ratio of about 1:1.
16. The pharmaceutical composition of claim 1 wherein the pharmaceutically acceptable solvent is in an amount of from about 10% to about 30% by weight of the total composition.
17. The pharmaceutical composition of claim 1 wherein the pharmaceutically acceptable solvent is in an amount of from about 15% to about 25% by weight of the total composition.
18. The pharmaceutical composition of claim 1 wherein the pharmaceutically acceptable surfactant is Polyoxyl 40 hydrogenated castor oil or Polyoxyl 35 castor oil.
19. The pharmaceutical composition of claim 1 wherein the surfactant is in an amount of from about 10% to about 50% by weight of the total composition.
20. The pharmaceutical composition of claim 1 wherein the surfactant is in an amount of from about 30% to about 45% by weight of the total composition.
21. The pharmaceutical composition of claim 1 wherein the composition further comprises an amine.
22. The pharmaceutical composition of claim 21 wherein the amine is lower alkylamine, basic amino acid or choline hydroxide.
23. The pharmaceutical composition of claim 22 wherein the lower alkylamine is ethanolamine, diethanolamine, triethanolamine, ethylenediamine, dimethylaminoethanol or tris(hydroxymethyl)aminomethane.
24. The pharmaceutical composition of claim 22 wherein the basic amino acid is arginine, lysine or guanidine.
25. The pharmaceutical composition of claim 21 wherein the amine is in an amount from about 0.1 % to about 10% by weight of the total composition.
26. A self emulsifying formulation vehicle comprising a mixture consisting essentially of diglyceride and monoglyceride in a ratio of from about 9:1 to about 6:4 by weight (diglyceride:monoglyceride) wherein the diglyceride and monoglyceride are mono-or di-unsaturated fatty acid esters of glycerol having sixteen to twenty-two carbon chain length, one or more pharmaceutically acceptable solvents, and one or more pharmaceutically acceptable surfactants;
wherein the solvent is propylene glycol, polypropylene glycol, polyethylene glycol, glycerol, ethanol, dimethyl isosorbide, glycofurol, propylene carbonate, dimethyl acetamide, or a mixture thereof; wherein said surfactant is Polyoxyl 40 hydrogenated castor oil, Polyoxyl 35 castor oil, polyethylene glycol 12-hydroxy stearate, polyoxyethylene glyceryl trioleate, Peglicol 6-oleate, Polyoxyethylene stearates, Poloxamers, Polysorbates, or Saturated Polyglycolyzed Glycerides.
wherein the solvent is propylene glycol, polypropylene glycol, polyethylene glycol, glycerol, ethanol, dimethyl isosorbide, glycofurol, propylene carbonate, dimethyl acetamide, or a mixture thereof; wherein said surfactant is Polyoxyl 40 hydrogenated castor oil, Polyoxyl 35 castor oil, polyethylene glycol 12-hydroxy stearate, polyoxyethylene glyceryl trioleate, Peglicol 6-oleate, Polyoxyethylene stearates, Poloxamers, Polysorbates, or Saturated Polyglycolyzed Glycerides.
27. The self emulsifying formulation vehicle of claim 26 further comprising an amine.
28. The self emulsifying formulation vehicle of claim 26 wherein said diglyceride is diolein, dilinoleate or a mixture thereof.
29. The self emulsifying formulation vehicle of claim 26 wherein said diglyceride is diolein.
30. The self emulsifying formulation vehicle of claim 26 wherein said monoglyceride is monoolein, monoolinoleate or a mixture thereof.
31. The self emulsifying formulation vehicle of claim 26 wherein said monoglyceride is monoolein.
32. The self emulsifying formulation vehicle of claim 26 wherein the mixture of diglyceride and monoglyceride is in a ratio of about 7:3 by weight diglyceride:monoglyceride).
33. The self emulsifying formulation vehicle of claim 26 wherein the mixture of diglyceride and monoglyceride is in a ratio of about 8:2 by weight (diglyceride:monoglyceride).
34. The self emulsifying formulation vehicle of claim 26 wherein the mixture of diglyceride and monoglyceride is in a ratio of about 9:1 by weight diglyceride:monoglyceride).
35. A pharmaceutical composition according to claim 1, wherein the mixture of diglyceride and monoglyceride is prepared by mixing diglyceride and monoglyceride in appropriate relative proportion.
36. A self emulsifying formulation vehicle according to claim 26, wherein the mixture of diglyceride and monoglyceride is prepared by mixing diglyceride and monoglyceride in appropriate relative proportion.
37. A pharmaceutical composition according to claim 1, wherein the composition is capable of forming a microemulsion upon mixing with water.
38. A pharmaceutical composition according to claim 37, wherein the microemulsion formed has an almost transparent or translucent appearance and the average particle (droplet) size of the emulsion is less than 150 nanometers (0.15 microns).
39. A pharmaceutical composition comprising:
(a) a lipophilic, pharmaceutically active agent;
(b) a mixture consisting of diolein and monoolein in a ratio of about 9:1 to about 8:2 by weight;
(c) a solvent comprising propylene glycol or a mixture of propylene glycol and ethanol in an amount of from about 15% to about 25% by weight of the total composition;
(d) a surfactant comprising glycerol polyethylene glycol oxystearate or glycerol polyethylene glycol ricinoleate in an amount of from about 30% to about 45% by weight of the total composition; and optionally a basic amine in an amount of about 0.1 % to about 7% of the total composition; and wherein the lipophilic active agent has a LOG P value >=2, an intrinsic aqueous solubility <=0.1 mg/ml in the pH range of 1 to 8, and a solubility greater than 1 mg/ml in the mixture of b, c and d as defined herein.
(a) a lipophilic, pharmaceutically active agent;
(b) a mixture consisting of diolein and monoolein in a ratio of about 9:1 to about 8:2 by weight;
(c) a solvent comprising propylene glycol or a mixture of propylene glycol and ethanol in an amount of from about 15% to about 25% by weight of the total composition;
(d) a surfactant comprising glycerol polyethylene glycol oxystearate or glycerol polyethylene glycol ricinoleate in an amount of from about 30% to about 45% by weight of the total composition; and optionally a basic amine in an amount of about 0.1 % to about 7% of the total composition; and wherein the lipophilic active agent has a LOG P value >=2, an intrinsic aqueous solubility <=0.1 mg/ml in the pH range of 1 to 8, and a solubility greater than 1 mg/ml in the mixture of b, c and d as defined herein.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5401297P | 1997-07-29 | 1997-07-29 | |
| US5407897P | 1997-07-29 | 1997-07-29 | |
| US60/054,012 | 1997-07-29 | ||
| US60/054,078 | 1997-07-29 | ||
| PCT/US1998/014818 WO1999006024A1 (en) | 1997-07-29 | 1998-07-27 | Self-emulsifying formulation for lipophilic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| CA2294031A1 CA2294031A1 (en) | 1999-02-11 |
| CA2294031C true CA2294031C (en) | 2005-01-18 |
| CA2294031E CA2294031E (en) | 2012-04-03 |
Family
ID=26732506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2294031A Expired - Fee Related CA2294031E (en) | 1997-07-29 | 1998-07-27 | Self-emulsifying formulation for lipophilic compounds |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0999826B1 (en) |
| JP (2) | JP2002511099A (en) |
| KR (1) | KR100509776B1 (en) |
| CN (1) | CN1208047C (en) |
| AT (1) | ATE265847T1 (en) |
| AU (1) | AU728698B2 (en) |
| BR (1) | BR9811058A (en) |
| CA (1) | CA2294031E (en) |
| CZ (1) | CZ297206B6 (en) |
| DE (1) | DE69823663T2 (en) |
| DK (1) | DK0999826T3 (en) |
| ES (1) | ES2219895T3 (en) |
| FI (1) | FI20000170A7 (en) |
| HU (1) | HU226114B1 (en) |
| NO (1) | NO328591B1 (en) |
| NZ (1) | NZ502569A (en) |
| PL (1) | PL191780B1 (en) |
| PT (1) | PT999826E (en) |
| RU (1) | RU2211021C2 (en) |
| SI (1) | SI0999826T1 (en) |
| SK (1) | SK284511B6 (en) |
| WO (1) | WO1999006024A1 (en) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6964946B1 (en) | 1995-10-26 | 2005-11-15 | Baker Norton Pharmaceuticals, Inc. | Oral pharmaceutical compositions containing taxanes and methods of treatment employing the same |
| SI0999838T1 (en) * | 1997-07-29 | 2002-08-31 | Pharmacia & Upjohn Company | Self-emulsifying formulation for lipophilic compounds |
| US5922754A (en) * | 1998-10-02 | 1999-07-13 | Abbott Laboratories | Pharmaceutical compositions containing paclitaxel |
| US6040330A (en) * | 1999-01-08 | 2000-03-21 | Bionumerik Pharmaceuticals, Inc. | Pharmaceutical formulations of taxanes |
| GB9903547D0 (en) | 1999-02-16 | 1999-04-07 | Novartis Ag | Organic compounds |
| US6294192B1 (en) * | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
| DE19912436A1 (en) * | 1999-03-19 | 2000-09-21 | Merckle Gmbh | Ibuprofen solution |
| US6652880B1 (en) | 1999-04-01 | 2003-11-25 | R.P. Scherer Technologies, Inc. | Oral pharmaceutical compositions containing long-chain triglycerides and liphophilic surfactants |
| EP1479382A1 (en) * | 1999-06-18 | 2004-11-24 | IVAX Research, Inc. | Oral pharmaceutical compositions containing taxanes and methods for treatment employing the same |
| GB2355656B (en) * | 1999-08-17 | 2004-04-07 | Galena As | Pharmaceutical compositions for oral and topical administration |
| GB0001928D0 (en) * | 2000-01-27 | 2000-03-22 | Novartis Ag | Organic compounds |
| KR20010100194A (en) * | 2000-03-13 | 2001-11-14 | 박호군 | Composition and formulation for solubilization of various compounds and preparation method thereof |
| US6610272B1 (en) * | 2000-05-01 | 2003-08-26 | Aeropharm Technology Incorporated | Medicinal aerosol formulation |
| US7115565B2 (en) | 2001-01-18 | 2006-10-03 | Pharmacia & Upjohn Company | Chemotherapeutic microemulsion compositions of paclitaxel with improved oral bioavailability |
| KR100425755B1 (en) * | 2001-08-27 | 2004-04-03 | 주식회사 원진신약 | Compositions containing itraconazole and their preparation methods |
| JP2005523295A (en) * | 2002-03-01 | 2005-08-04 | ノバガリ、ファルマ、エスアー | Self-emulsifying drug delivery system for poorly soluble drugs |
| EP1340497A1 (en) * | 2002-03-01 | 2003-09-03 | Novagali Sas | Self emulsifying drug delivery systems for poorly soluble drugs |
| US7182950B2 (en) * | 2002-06-12 | 2007-02-27 | Nutralease Ltd. | Nano-sized self-assembled liquid dilutable vehicles |
| KR100533458B1 (en) * | 2002-07-20 | 2005-12-07 | 대화제약 주식회사 | Composition for solubilization of paclitaxel and preparation method thereof |
| KR100573289B1 (en) * | 2002-07-20 | 2006-04-24 | 대화제약 주식회사 | Paclitaxel composition for the treatment of bladder cancer through intra-bladder administration and method for preparing the same |
| US20040185068A1 (en) * | 2003-03-18 | 2004-09-23 | Zhi-Jian Yu | Self-emulsifying compositions, methods of use and preparation |
| CA2520660C (en) * | 2003-03-28 | 2013-08-20 | Sigmoid Biotechnologies Limited | Solid oral dosage form containing seamless microcapsules |
| GT200500310A (en) * | 2004-11-19 | 2006-06-19 | ORGANIC COMPOUNDS | |
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1998
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