DE69734988T2 - Zubereitungen enthaltend mikropartikel von wasserunlöslichen stoffen und verfahren zu deren herstellung - Google Patents
Zubereitungen enthaltend mikropartikel von wasserunlöslichen stoffen und verfahren zu deren herstellung Download PDFInfo
- Publication number
- DE69734988T2 DE69734988T2 DE69734988T DE69734988T DE69734988T2 DE 69734988 T2 DE69734988 T2 DE 69734988T2 DE 69734988 T DE69734988 T DE 69734988T DE 69734988 T DE69734988 T DE 69734988T DE 69734988 T2 DE69734988 T2 DE 69734988T2
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- Prior art keywords
- agent
- phospholipid
- compound
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- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000011859 microparticle Substances 0.000 title claims abstract description 45
- 239000000126 substance Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims description 44
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002245 particle Substances 0.000 claims abstract description 94
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000004094 surface-active agent Substances 0.000 claims description 35
- 239000000725 suspension Substances 0.000 claims description 31
- -1 fatty acid ester Chemical class 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 235000013601 eggs Nutrition 0.000 claims description 20
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 20
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 15
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 10
- 239000001961 anticonvulsive agent Substances 0.000 claims description 10
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 10
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- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 7
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 6
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- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 6
- KAKVFSYQVNHFBS-UHFFFAOYSA-N (5-hydroxycyclopenten-1-yl)-phenylmethanone Chemical compound OC1CCC=C1C(=O)C1=CC=CC=C1 KAKVFSYQVNHFBS-UHFFFAOYSA-N 0.000 claims description 5
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- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims description 5
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- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 5
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 claims description 5
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 claims description 5
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 5
- 235000015097 nutrients Nutrition 0.000 claims description 5
- ZHALDANPYXAMJF-UHFFFAOYSA-N octadecanoate;tris(2-hydroxyethyl)azanium Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCCCCCCC([O-])=O ZHALDANPYXAMJF-UHFFFAOYSA-N 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 239000000932 sedative agent Substances 0.000 claims description 5
- FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 claims description 5
- 229940083575 sodium dodecyl sulfate Drugs 0.000 claims description 5
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 claims description 5
- 229940029614 triethanolamine stearate Drugs 0.000 claims description 5
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims description 4
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000164 antipsychotic agent Substances 0.000 claims description 4
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001840 cholesterol esters Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000003905 phosphatidylinositols Chemical class 0.000 claims description 4
- 150000003839 salts Chemical group 0.000 claims description 4
- 229940012831 stearyl alcohol Drugs 0.000 claims description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 3
- 229940125681 anticonvulsant agent Drugs 0.000 claims description 3
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 3
- 239000012216 imaging agent Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000005185 salting out Methods 0.000 claims description 3
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- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 239000012296 anti-solvent Substances 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000000693 micelle Substances 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
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- QLNOOKSBAYIHQI-SKZICHJRSA-M sodium;2,3-dihydroxypropyl [(2r)-2,3-di(tetradecanoyloxy)propyl] phosphate Chemical compound [Na+].CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCC QLNOOKSBAYIHQI-SKZICHJRSA-M 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 6
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- 230000003444 anaesthetic effect Effects 0.000 claims 4
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- 239000003416 antiarrhythmic agent Substances 0.000 claims 4
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- 125000001453 quaternary ammonium group Chemical group 0.000 claims 4
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- 150000002194 fatty esters Chemical class 0.000 claims 2
- 238000000227 grinding Methods 0.000 claims 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
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- 125000003724 cholesterol ester group Chemical group 0.000 claims 1
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- TTZNHSISALZPTM-UHFFFAOYSA-N ethane-1,2-diamine;2-methyloxirane Chemical compound CC1CO1.NCCN TTZNHSISALZPTM-UHFFFAOYSA-N 0.000 claims 1
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- 238000001361 intraarterial administration Methods 0.000 claims 1
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- HNJXPTMEWIVQQM-UHFFFAOYSA-M triethyl(hexadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC HNJXPTMEWIVQQM-UHFFFAOYSA-M 0.000 claims 1
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Classifications
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- 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
- A61K9/51—Nanocapsules; Nanoparticles
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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
- A61K9/48—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
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/5123—Organic compounds, e.g. fats, sugars
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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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
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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
- A61K9/48—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
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5146—Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
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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
- A61K9/48—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
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5192—Processes
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
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- Y10S977/827—Nanostructure formed from hybrid organic/inorganic semiconductor compositions
- Y10S977/828—Biological composition interconnected with inorganic material
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/84—Manufacture, treatment, or detection of nanostructure
- Y10S977/882—Assembling of separate components, e.g. by attaching
- Y10S977/883—Fluidic self-assembly, FSA
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/906—Drug delivery
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/915—Therapeutic or pharmaceutical composition
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/931—Medical device coating
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Biomedical Technology (AREA)
- Nanotechnology (AREA)
- Physics & Mathematics (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70148396A | 1996-08-22 | 1996-08-22 | |
| US701483 | 1996-08-22 | ||
| PCT/US1997/004695 WO1998007414A1 (en) | 1996-08-22 | 1997-03-28 | Compositions comprising microparticles of water-insoluble substances and method for preparing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69734988D1 DE69734988D1 (de) | 2006-02-02 |
| DE69734988T2 true DE69734988T2 (de) | 2006-09-21 |
Family
ID=24817566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69734988T Expired - Lifetime DE69734988T2 (de) | 1996-08-22 | 1997-03-28 | Zubereitungen enthaltend mikropartikel von wasserunlöslichen stoffen und verfahren zu deren herstellung |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5922355A (OSRAM) |
| EP (1) | EP0925061B1 (OSRAM) |
| JP (1) | JP2000516244A (OSRAM) |
| KR (1) | KR100542816B1 (OSRAM) |
| CN (1) | CN1303985C (OSRAM) |
| AT (1) | ATE314055T1 (OSRAM) |
| AU (1) | AU719085B2 (OSRAM) |
| CA (1) | CA2263102C (OSRAM) |
| CZ (1) | CZ299790B6 (OSRAM) |
| DE (1) | DE69734988T2 (OSRAM) |
| ES (1) | ES2252780T3 (OSRAM) |
| HU (1) | HU226608B1 (OSRAM) |
| IL (1) | IL128632A (OSRAM) |
| NO (1) | NO325197B1 (OSRAM) |
| NZ (1) | NZ333844A (OSRAM) |
| PL (1) | PL192560B1 (OSRAM) |
| RO (1) | RO120603B1 (OSRAM) |
| RU (1) | RU2186562C2 (OSRAM) |
| WO (1) | WO1998007414A1 (OSRAM) |
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| JP4484247B2 (ja) * | 1995-02-24 | 2010-06-16 | エラン ファーマ インターナショナル，リミティド | ナノ粒子分散体を含有するエアロゾル |
| US6143211A (en) * | 1995-07-21 | 2000-11-07 | Brown University Foundation | Process for preparing microparticles through phase inversion phenomena |
| EP0855906B1 (en) * | 1995-10-17 | 2008-02-20 | Jagotec AG | Insoluble drug delivery |
| US5858401A (en) | 1996-01-22 | 1999-01-12 | Sidmak Laboratories, Inc. | Pharmaceutical composition for cyclosporines |
| US6465016B2 (en) * | 1996-08-22 | 2002-10-15 | Research Triangle Pharmaceuticals | Cyclosporiine particles |
| US7255877B2 (en) | 1996-08-22 | 2007-08-14 | Jagotec Ag | Fenofibrate microparticles |
| US6565885B1 (en) | 1997-09-29 | 2003-05-20 | Inhale Therapeutic Systems, Inc. | Methods of spray drying pharmaceutical compositions |
| US20060165606A1 (en) | 1997-09-29 | 2006-07-27 | Nektar Therapeutics | Pulmonary delivery particles comprising water insoluble or crystalline active agents |
| US6337092B1 (en) | 1998-03-30 | 2002-01-08 | Rtp Pharma Inc. | Composition and method of preparing microparticles of water-insoluble substances |
| KR100628341B1 (ko) * | 1998-03-30 | 2006-09-27 | 스키에파마 캐나다 인코포레이티드 | 수-불용성 물질의 미소입자 조성물 및 이의 제조방법 |
| US6979456B1 (en) | 1998-04-01 | 2005-12-27 | Jagotec Ag | Anticancer compositions |
| HK1039458B (zh) | 1998-05-29 | 2006-09-01 | Skyepharma Canada Inc. | 熱保護微粒組合物及其最終蒸汽滅菌的方法 |
| WO1999065469A2 (en) | 1998-06-19 | 1999-12-23 | Rtp Pharma Inc. | Processes to generate submicron particles of water-insoluble compounds |
| HK1040195B (zh) | 1998-08-19 | 2006-06-02 | Skyepharma Canada Inc. | 普鲁泊福的可注射水分散体 |
| US6551613B1 (en) * | 1998-09-08 | 2003-04-22 | Alza Corporation | Dosage form comprising therapeutic formulation |
| US8236352B2 (en) * | 1998-10-01 | 2012-08-07 | Alkermes Pharma Ireland Limited | Glipizide compositions |
| AU6283299A (en) * | 1998-10-01 | 2000-04-17 | Elan Pharma International Limited | Controlled release nanoparticulate compositions |
| US20040013613A1 (en) * | 2001-05-18 | 2004-01-22 | Jain Rajeev A | Rapidly disintegrating solid oral dosage form |
| US20090297602A1 (en) * | 1998-11-02 | 2009-12-03 | Devane John G | Modified Release Loxoprofen Compositions |
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| WO2000030615A1 (en) * | 1998-11-20 | 2000-06-02 | Rtp Pharma Inc. | Method of preparing stable suspensions of insoluble microparticles |
| AU767154B2 (en) * | 1998-11-20 | 2003-10-30 | Skyepharma Canada Inc. | Dispersible phospholipid stabilized microparticles |
| US6251886B1 (en) | 1998-12-07 | 2001-06-26 | Schering Corporation | Methods of using temozolomide in the treatment of cancers |
| EE200100342A (xx) | 1998-12-23 | 2002-10-15 | Idea Ag | Parendatud ravimvorm in vivo mitteinvasiivseks paikseks rakendamiseks |
| US7374779B2 (en) * | 1999-02-26 | 2008-05-20 | Lipocine, Inc. | Pharmaceutical formulations and systems for improved absorption and multistage release of active agents |
| US20030236236A1 (en) * | 1999-06-30 | 2003-12-25 | Feng-Jing Chen | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
| MXPA02000053A (es) | 1999-07-05 | 2003-07-21 | Idea Ag | Un metodo para mejorar el tratamiento a traves de barreras adaptables semipermeables. |
| DE19932157A1 (de) * | 1999-07-13 | 2001-01-18 | Pharmasol Gmbh | Verfahren zur schonenden Herstellung von hochfeinen Mikropartikeln und Nanopartikeln |
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- 1997-03-28 IL IL12863297A patent/IL128632A/xx not_active IP Right Cessation
- 1997-03-28 CZ CZ0059699A patent/CZ299790B6/cs not_active IP Right Cessation
- 1997-03-28 JP JP10510706A patent/JP2000516244A/ja active Pending
- 1997-03-28 HU HU9903537A patent/HU226608B1/hu not_active IP Right Cessation
- 1997-03-28 CN CNB971973652A patent/CN1303985C/zh not_active Expired - Fee Related
- 1997-03-28 RO RO99-00195A patent/RO120603B1/ro unknown
- 1997-03-28 PL PL331715A patent/PL192560B1/pl unknown
- 1997-03-28 RU RU99105851/14A patent/RU2186562C2/ru not_active IP Right Cessation
- 1997-03-28 EP EP97917593A patent/EP0925061B1/en not_active Expired - Lifetime
- 1997-03-28 AT AT97917593T patent/ATE314055T1/de not_active IP Right Cessation
- 1997-03-28 ES ES97917593T patent/ES2252780T3/es not_active Expired - Lifetime
- 1997-03-28 DE DE69734988T patent/DE69734988T2/de not_active Expired - Lifetime
- 1997-03-28 WO PCT/US1997/004695 patent/WO1998007414A1/en not_active Ceased
- 1997-03-28 AU AU25871/97A patent/AU719085B2/en not_active Ceased
- 1997-03-28 NZ NZ333844A patent/NZ333844A/xx not_active IP Right Cessation
- 1997-03-28 KR KR1019997001435A patent/KR100542816B1/ko not_active Expired - Fee Related
- 1997-03-28 CA CA002263102A patent/CA2263102C/en not_active Expired - Fee Related
- 1997-09-29 US US08/939,699 patent/US5922355A/en not_active Expired - Lifetime
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1998
- 1998-12-22 US US09/218,080 patent/US6228399B1/en not_active Expired - Lifetime
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- 1999-02-19 NO NO19990790A patent/NO325197B1/no not_active IP Right Cessation
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| CA2263102C (en) | 2006-08-15 |
| CZ59699A3 (cs) | 1999-06-16 |
| KR100542816B1 (ko) | 2006-01-11 |
| PL331715A1 (en) | 1999-08-02 |
| IL128632A0 (en) | 2000-01-31 |
| JP2000516244A (ja) | 2000-12-05 |
| AU719085B2 (en) | 2000-05-04 |
| AU2587197A (en) | 1998-03-06 |
| NZ333844A (en) | 2000-10-27 |
| CA2263102A1 (en) | 1998-02-26 |
| CN1303985C (zh) | 2007-03-14 |
| CZ299790B6 (cs) | 2008-11-26 |
| RU2186562C2 (ru) | 2002-08-10 |
| KR20000035808A (ko) | 2000-06-26 |
| NO990790D0 (no) | 1999-02-19 |
| HK1021140A1 (en) | 2000-06-02 |
| NO325197B1 (no) | 2008-02-18 |
| HUP9903537A2 (hu) | 2000-02-28 |
| WO1998007414A1 (en) | 1998-02-26 |
| US6228399B1 (en) | 2001-05-08 |
| ES2252780T3 (es) | 2006-05-16 |
| HU226608B1 (hu) | 2009-04-28 |
| EP0925061A1 (en) | 1999-06-30 |
| EP0925061B1 (en) | 2005-12-28 |
| RO120603B1 (ro) | 2006-05-30 |
| HUP9903537A3 (en) | 2000-05-29 |
| DE69734988D1 (de) | 2006-02-02 |
| PL192560B1 (pl) | 2006-11-30 |
| CN1228021A (zh) | 1999-09-08 |
| IL128632A (en) | 2003-03-12 |
| ATE314055T1 (de) | 2006-01-15 |
| US5922355A (en) | 1999-07-13 |
| NO990790L (no) | 1999-04-19 |
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