CA2263765C - Procedes de production de particules de proteines utiles dans la diffusion d'agents pharmacologiques - Google Patents
Procedes de production de particules de proteines utiles dans la diffusion d'agents pharmacologiques Download PDFInfo
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- CA2263765C CA2263765C CA2263765A CA2263765A CA2263765C CA 2263765 C CA2263765 C CA 2263765C CA 2263765 A CA2263765 A CA 2263765A CA 2263765 A CA2263765 A CA 2263765A CA 2263765 C CA2263765 C CA 2263765C
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- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 claims 2
- 229960005356 urokinase Drugs 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- JSWWYAITRNDLLQ-HBJDUEGVSA-N (3s,3ar,6s,6as)-3,6,6a-trihydroxy-6-(5-methylfuran-2-yl)-3,3a-dihydro-2h-furo[3,2-b]furan-5-one Chemical compound O1C(C)=CC=C1[C@]1(O)[C@@]2(O)OC[C@H](O)[C@H]2OC1=O JSWWYAITRNDLLQ-HBJDUEGVSA-N 0.000 claims 1
- MHFRGQHAERHWKZ-HHHXNRCGSA-N (R)-edelfosine Chemical compound CCCCCCCCCCCCCCCCCCOC[C@@H](OC)COP([O-])(=O)OCC[N+](C)(C)C MHFRGQHAERHWKZ-HHHXNRCGSA-N 0.000 claims 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims 1
- JDVVGAQPNNXQDW-WCMLQCRESA-N Castanospermine Natural products O[C@H]1[C@@H](O)[C@H]2[C@@H](O)CCN2C[C@H]1O JDVVGAQPNNXQDW-WCMLQCRESA-N 0.000 claims 1
- JDVVGAQPNNXQDW-TVNFTVLESA-N Castinospermine Chemical compound C1[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H](O)CCN21 JDVVGAQPNNXQDW-TVNFTVLESA-N 0.000 claims 1
- DYEFUKCXAQOFHX-UHFFFAOYSA-N Ebselen Chemical compound [se]1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 DYEFUKCXAQOFHX-UHFFFAOYSA-N 0.000 claims 1
- 102000000795 Galectin 1 Human genes 0.000 claims 1
- 108010001498 Galectin 1 Proteins 0.000 claims 1
- 102000008070 Interferon-gamma Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- HZQDCMWJEBCWBR-UUOKFMHZSA-N Mizoribine Chemical compound OC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HZQDCMWJEBCWBR-UUOKFMHZSA-N 0.000 claims 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 1
- 229960004150 aciclovir Drugs 0.000 claims 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 1
- 229960001280 amantadine hydrochloride Drugs 0.000 claims 1
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 claims 1
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 claims 1
- 229960002495 buspirone Drugs 0.000 claims 1
- 229910001424 calcium ion Inorganic materials 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 238000013270 controlled release Methods 0.000 claims 1
- 229950010033 ebselen Drugs 0.000 claims 1
- 229950011461 edelfosine Drugs 0.000 claims 1
- 229950002798 enlimomab Drugs 0.000 claims 1
- 238000001476 gene delivery Methods 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229960003130 interferon gamma Drugs 0.000 claims 1
- 229950000844 mizoribine Drugs 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 1
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 1
- 238000001890 transfection Methods 0.000 claims 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims 1
- 229960002555 zidovudine Drugs 0.000 claims 1
- 150000002500 ions Chemical class 0.000 abstract 2
- 239000002105 nanoparticle Substances 0.000 abstract 2
- 102000008100 Human Serum Albumin Human genes 0.000 abstract 1
- 108091006905 Human Serum Albumin Proteins 0.000 abstract 1
- 102000007562 Serum Albumin Human genes 0.000 abstract 1
- 108010071390 Serum Albumin Proteins 0.000 abstract 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 abstract 1
- 238000000975 co-precipitation Methods 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 239000011859 microparticle Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 230000006920 protein precipitation Effects 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
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
- A61K9/48—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
- A61K9/5169—Proteins, e.g. albumin, gelatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/223—Microbubbles, hollow microspheres, free gas bubbles, gas microspheres
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1658—Proteins, e.g. albumin, gelatin
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biomedical Technology (AREA)
- Optics & Photonics (AREA)
- Nanotechnology (AREA)
- Acoustics & Sound (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Abstract
La présente invention concerne un procédé mis au point en vue de la formation de particules submicromies (nanoparticules) par dénaturation thermique de protéines (telles que l'albumine sérique humaine) en présence d'ions polyvalents (tels que du calcium). Elle concerne également des produits nouveaux élaborés par application dudit procédé. Une concentration appropriée d'ions polyvalents, compris dans une gamme relativement étroite de concentrations, entraîne la précipitation d'une protéine sous la forme de particules colloïdales, à une température bien inférieure à celle de la dénaturation thermique de la protéine (cette température pouvant aller jusqu'à 60 ·C dans le cas de l'albumine sérique). Les températures utilisées dans l'application dudit procédé sont suffisamment basses pour que d'autres molécules puissent être incorporées dans les particules submicromiques de la présente invention, y compris des composés ne supportant pas des températures élevées (cette incorporation se faisant par exemple, par coprécipitation). Ces procédés facilitent la production de nanoparticules et de microparticules contenant diverses molécules (telles que des acides nucléiques, des oligonucléotides, des polynucléotides, de l'ADN, de l'ARN, des polysaccharides, des ribozymes, des composés pharmacologiquement actifs, et d'autres composés similaires) utiles, notamment, à des fins thérapeutiques et diagnostiques. L'adjonction de cations polyvalents sert à la fois à induire la précipitation et à permettre la liaison de molécules à charge négative, telles que l'ADN, avec une protéine à charge négative.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2396896P | 1996-08-19 | 1996-08-19 | |
| US60/023,968 | 1996-08-19 | ||
| PCT/US1997/014661 WO1998007410A1 (fr) | 1996-08-19 | 1997-08-19 | Procedes de production de particules de proteines utiles dans la diffusion d'agents pharmacologiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2263765A1 CA2263765A1 (fr) | 1998-02-26 |
| CA2263765C true CA2263765C (fr) | 2010-03-30 |
Family
ID=21818165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2263765A Expired - Lifetime CA2263765C (fr) | 1996-08-19 | 1997-08-19 | Procedes de production de particules de proteines utiles dans la diffusion d'agents pharmacologiques |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0938299A4 (fr) |
| AU (1) | AU3916997A (fr) |
| CA (1) | CA2263765C (fr) |
| WO (1) | WO1998007410A1 (fr) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6254890B1 (en) * | 1997-12-12 | 2001-07-03 | Massachusetts Institute Of Technology | Sub-100nm biodegradable polymer spheres capable of transporting and releasing nucleic acids |
| EP1348034B1 (fr) * | 2000-11-15 | 2016-07-20 | Minerva Biotechnologies Corporation | Identifieurs d'oligonucleotides |
| US6884436B2 (en) | 2000-12-22 | 2005-04-26 | Baxter International Inc. | Method for preparing submicron particle suspensions |
| US9700866B2 (en) | 2000-12-22 | 2017-07-11 | Baxter International Inc. | Surfactant systems for delivery of organic compounds |
| US6977085B2 (en) | 2000-12-22 | 2005-12-20 | Baxter International Inc. | Method for preparing submicron suspensions with polymorph control |
| US7193084B2 (en) | 2000-12-22 | 2007-03-20 | Baxter International Inc. | Polymorphic form of itraconazole |
| US6869617B2 (en) | 2000-12-22 | 2005-03-22 | Baxter International Inc. | Microprecipitation method for preparing submicron suspensions |
| US6951656B2 (en) | 2000-12-22 | 2005-10-04 | Baxter International Inc. | Microprecipitation method for preparing submicron suspensions |
| US8067032B2 (en) | 2000-12-22 | 2011-11-29 | Baxter International Inc. | Method for preparing submicron particles of antineoplastic agents |
| CA2441108A1 (fr) * | 2001-04-05 | 2002-10-17 | Universite Laval | Procede de fabrication d'une matrice d'administration et utilisations |
| JP2005504090A (ja) | 2001-09-26 | 2005-02-10 | バクスター・インターナショナル・インコーポレイテッド | 分散体および溶媒相または液相の除去によるサブミクロンサイズ−ナノ粒子の調製 |
| US20060003012A9 (en) | 2001-09-26 | 2006-01-05 | Sean Brynjelsen | Preparation of submicron solid particle suspensions by sonication of multiphase systems |
| US7112340B2 (en) | 2001-10-19 | 2006-09-26 | Baxter International Inc. | Compositions of and method for preparing stable particles in a frozen aqueous matrix |
| JP4212921B2 (ja) * | 2002-03-29 | 2009-01-21 | 独立行政法人科学技術振興機構 | 抗体を提示するタンパク質中空ナノ粒子を用いる治療薬剤およびタンパク質中空ナノ粒子 |
| IL150906A0 (en) | 2002-07-25 | 2003-02-12 | Yissum Res Dev Co | Diagnostic microspheres |
| EP1585548B1 (fr) | 2002-12-09 | 2018-06-27 | Abraxis BioScience, LLC | Compositions et methodes d'administration d'agents pharmacologiques |
| FR2902007B1 (fr) * | 2006-06-09 | 2012-01-13 | Flamel Tech Sa | Formulations pharmaceutiques pour la liberation prolongee de principe(s) actif(s) ainsi que leurs applications notamment therapeutiques |
| WO2011153010A1 (fr) | 2010-06-04 | 2011-12-08 | Abraxis Biosciences, Llc | Procédés de traitement du cancer du pancréas |
| EP2510930A1 (fr) | 2011-04-15 | 2012-10-17 | Bionanoplus, S.L. | Nanoparticules comportant des semi-esters de poly (méthyl vinyl éther-co-maléique anhydride) et leurs utilisations |
| CA2965759C (fr) | 2014-10-31 | 2023-12-12 | Glaxosmithkline Intellectual Property Development Limited | Polypeptides en poudre presentant moins d'impuretes de disulfide comprenant des materiaux cationiques divalents |
| CN110302364A (zh) * | 2019-06-24 | 2019-10-08 | 浙江工商大学 | 一种自组装过氧化氢酶纳米颗粒及其制备方法和应用 |
| CN115154651B (zh) * | 2022-06-23 | 2023-10-27 | 华中科技大学 | 一种生物矿化的牛血清白蛋白@钙硒纳米球、制备方法及应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6020059B2 (ja) * | 1980-09-16 | 1985-05-20 | 雪印乳業株式会社 | 食品または医薬品に適したマイクロカプセルの製造法 |
| US5585112A (en) * | 1989-12-22 | 1996-12-17 | Imarx Pharmaceutical Corp. | Method of preparing gas and gaseous precursor-filled microspheres |
| GB9106686D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
| JP3482242B2 (ja) * | 1994-06-10 | 2003-12-22 | 株式会社キティー | 生理活性物質の封入されている微粒子及びその製法 |
-
1997
- 1997-08-19 AU AU39169/97A patent/AU3916997A/en not_active Abandoned
- 1997-08-19 EP EP97936517A patent/EP0938299A4/fr not_active Withdrawn
- 1997-08-19 WO PCT/US1997/014661 patent/WO1998007410A1/fr not_active Application Discontinuation
- 1997-08-19 CA CA2263765A patent/CA2263765C/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU3916997A (en) | 1998-03-06 |
| EP0938299A4 (fr) | 2001-01-17 |
| WO1998007410A1 (fr) | 1998-02-26 |
| CA2263765A1 (fr) | 1998-02-26 |
| EP0938299A1 (fr) | 1999-09-01 |
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