WO1993017665A1 - Methods and apparatus for drug delivery using supercritical solutions - Google Patents
Methods and apparatus for drug delivery using supercritical solutions Download PDFInfo
- Publication number
- WO1993017665A1 WO1993017665A1 PCT/US1993/001501 US9301501W WO9317665A1 WO 1993017665 A1 WO1993017665 A1 WO 1993017665A1 US 9301501 W US9301501 W US 9301501W WO 9317665 A1 WO9317665 A1 WO 9317665A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methods
- supercritical fluid
- physiologically active
- drug delivery
- animal
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/30—Mixing gases with solids
- B01F23/39—Mixing systems, i.e. flow charts or diagrams
-
- 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
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
-
- 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
- A61K9/12—Aerosols; Foams
-
- 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
- A61K9/12—Aerosols; Foams
- A61K9/124—Aerosols; Foams characterised by the propellant
-
- 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
- A61K9/1682—Processes
- A61K9/1688—Processes resulting in pure drug agglomerate optionally containing up to 5% of excipient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M15/00—Inhalators
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/04—Specific aggregation state of one or more of the phases to be mixed
- B01F23/043—Mixing fluids or with fluids in a supercritical state, in supercritical conditions or variable density fluids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/09—Mixing systems, i.e. flow charts or diagrams for components having more than two different of undetermined agglomeration states, e.g. supercritical states
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/30—Mixing gases with solids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/30—Mixing gases with solids
- B01F23/32—Mixing gases with solids by introducing solids in gas volumes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/20—Jet mixers, i.e. mixers using high-speed fluid streams
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/20—Jet mixers, i.e. mixers using high-speed fluid streams
- B01F25/28—Jet mixers, i.e. mixers using high-speed fluid streams characterised by the specific design of the jet injector
- B01F25/281—Jet mixers, i.e. mixers using high-speed fluid streams characterised by the specific design of the jet injector the jet injector being of the explosive rapid expansion of supercritical solutions [RESS] or fluid injection of molecular spray [FIMS] type, i.e. the liquid is jetted in an environment (gas or liquid) by nozzles, in conditions of significant pressure drop, with the possible generation of shock waves
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J3/00—Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
- B01J3/008—Processes carried out under supercritical conditions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05B—SPRAYING APPARATUS; ATOMISING APPARATUS; NOZZLES
- B05B7/00—Spraying apparatus for discharge of liquids or other fluent materials from two or more sources, e.g. of liquid and air, of powder and gas
- B05B7/24—Spraying apparatus for discharge of liquids or other fluent materials from two or more sources, e.g. of liquid and air, of powder and gas with means, e.g. a container, for supplying liquid or other fluent material to a discharge device
- B05B7/26—Apparatus in which liquids or other fluent materials from different sources are brought together before entering the discharge device
- B05B7/28—Apparatus in which liquids or other fluent materials from different sources are brought together before entering the discharge device in which one liquid or other fluent material is fed or drawn through an orifice into a stream of a carrying fluid
- B05B7/32—Apparatus in which liquids or other fluent materials from different sources are brought together before entering the discharge device in which one liquid or other fluent material is fed or drawn through an orifice into a stream of a carrying fluid the fed liquid or other fluent material being under pressure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/02—Processes for applying liquids or other fluent materials performed by spraying
- B05D1/025—Processes for applying liquids or other fluent materials performed by spraying using gas close to its critical state
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F2101/00—Mixing characterised by the nature of the mixed materials or by the application field
- B01F2101/22—Mixing of ingredients for pharmaceutical or medical compositions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D2401/00—Form of the coating product, e.g. solution, water dispersion, powders or the like
- B05D2401/90—Form of the coating product, e.g. solution, water dispersion, powders or the like at least one component of the composition being in supercritical state or close to supercritical state
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU37261/93A AU3726193A (en) | 1992-03-06 | 1993-02-19 | Methods and apparatus for drug delivery using supercritical solutions |
DE69314326T DE69314326T2 (en) | 1992-03-06 | 1993-02-19 | METHOD AND DEVICE FOR RELEASING ACTIVE SUBSTANCE BY SUPER-CRITICAL SOLUTIONS |
EP93906094A EP0627910B1 (en) | 1992-03-06 | 1993-02-19 | Methods and apparatus for drug delivery using supercritical solutions |
CA002131393A CA2131393C (en) | 1992-03-06 | 1993-02-19 | Method and apparatus for drug delivery using supercritical solutions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US846,331 | 1992-03-06 | ||
US07/846,331 US5301664A (en) | 1992-03-06 | 1992-03-06 | Methods and apparatus for drug delivery using supercritical solutions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993017665A1 true WO1993017665A1 (en) | 1993-09-16 |
Family
ID=25297595
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1993/001501 WO1993017665A1 (en) | 1992-03-06 | 1993-02-19 | Methods and apparatus for drug delivery using supercritical solutions |
Country Status (7)
Country | Link |
---|---|
US (1) | US5301664A (en) |
EP (1) | EP0627910B1 (en) |
AT (1) | ATE158716T1 (en) |
CA (1) | CA2131393C (en) |
DE (1) | DE69314326T2 (en) |
MX (1) | MX9301246A (en) |
WO (1) | WO1993017665A1 (en) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995024892A1 (en) * | 1994-03-14 | 1995-09-21 | Abbott Laboratories | Aerosol drug formulations containing vitamin e |
WO1995031964A1 (en) * | 1994-05-21 | 1995-11-30 | Glaxo Wellcome Australia Limited | Fluticasone propionate formulations |
EP0718035A3 (en) * | 1994-12-19 | 1997-04-09 | Basf Ag | Method and apparatus for preparing dispersions containing active substances |
US5639441A (en) * | 1992-03-06 | 1997-06-17 | Board Of Regents Of University Of Colorado | Methods for fine particle formation |
WO1998029110A2 (en) * | 1996-12-30 | 1998-07-09 | Battelle Memorial Institute | Formulation and method for treating neoplasms by inhalation |
WO1998034595A1 (en) * | 1997-02-05 | 1998-08-13 | Jago Research Ag | Medical aerosol formulations |
WO1999055319A1 (en) * | 1998-04-24 | 1999-11-04 | Glaxo Group Limited | Aerosol formulations of salmeterol xinafoate |
WO2000006121A1 (en) * | 1998-07-24 | 2000-02-10 | Jago Research Ag | Medicinal aerosol formulations |
US6032836A (en) * | 1995-04-13 | 2000-03-07 | Glaxo Group Limited | Metered dose aerosol valve |
US6039974A (en) * | 1997-08-26 | 2000-03-21 | Hoechst Marion Roussel, Inc. | Pharmaceutical composition for combination of piperidinoalkanol-decongestant |
US6113942A (en) * | 1995-02-28 | 2000-09-05 | Aventis Pharmaceuticals Inc. | Pharmaceutical composition for piperidinoalkanol compounds |
US6475467B1 (en) | 1998-08-04 | 2002-11-05 | Jago Research Ag | Medicinal aerosol formulations |
EP1354581A1 (en) * | 2000-12-26 | 2003-10-22 | Takeda Chemical Industries, Ltd. | Porous substance and process for producing the same |
CN106063778A (en) * | 2015-04-21 | 2016-11-02 | 北京化工大学 | A kind of preparation method of beclometasone transparent aqueous phase Nanodispersion |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6063910A (en) * | 1991-11-14 | 2000-05-16 | The Trustees Of Princeton University | Preparation of protein microparticles by supercritical fluid precipitation |
DK0797988T3 (en) | 1993-07-19 | 2009-05-11 | Univ British Columbia | Anti-angiogenic compositions and methods for their use |
US5716981A (en) * | 1993-07-19 | 1998-02-10 | Angiogenesis Technologies, Inc. | Anti-angiogenic compositions and methods of use |
US5451569A (en) * | 1994-04-19 | 1995-09-19 | Hong Kong University Of Science And Technology R & D Corporation Limited | Pulmonary drug delivery system |
JP5038552B2 (en) * | 1995-10-17 | 2012-10-03 | オバン・エナジー・リミテッド | Insoluble drug delivery |
US5833891A (en) * | 1996-10-09 | 1998-11-10 | The University Of Kansas | Methods for a particle precipitation and coating using near-critical and supercritical antisolvents |
US5874029A (en) * | 1996-10-09 | 1999-02-23 | The University Of Kansas | Methods for particle micronization and nanonization by recrystallization from organic solutions sprayed into a compressed antisolvent |
DE19616573C2 (en) * | 1996-04-25 | 1999-03-04 | Pari Gmbh | Use of subcritical blowing agent mixtures and aerosols for the micronization of drugs with the help of dense gases |
AU737078C (en) * | 1996-05-24 | 2002-05-02 | Angiotech Pharmaceuticals, Inc. | Compositions and methods for treating or preventing diseases of body passageways |
US6515016B2 (en) | 1996-12-02 | 2003-02-04 | Angiotech Pharmaceuticals, Inc. | Composition and methods of paclitaxel for treating psoriasis |
US6218353B1 (en) * | 1997-08-27 | 2001-04-17 | Micell Technologies, Inc. | Solid particulate propellant systems and aerosol containers employing the same |
US6200352B1 (en) | 1997-08-27 | 2001-03-13 | Micell Technologies, Inc. | Dry cleaning methods and compositions |
GB9810559D0 (en) * | 1998-05-15 | 1998-07-15 | Bradford Particle Design Ltd | Method and apparatus for particle formation |
SE9804001D0 (en) * | 1998-11-23 | 1998-11-23 | Astra Ab | New process |
US7081133B2 (en) * | 1999-01-19 | 2006-07-25 | Carbomedics Inc. | Antibiotic treated implantable medical devices |
CN1198593C (en) | 1999-06-09 | 2005-04-27 | 罗伯特·E·希弗斯 | Supercritical fluid-assisted nebulization and bubble drying |
WO2001024917A1 (en) | 1999-10-07 | 2001-04-12 | Battelle Memorial Institute | Method and apparatus for obtaining a suspension of particles |
FR2803538B1 (en) * | 1999-12-15 | 2002-06-07 | Separex Sa | METHOD AND DEVICE FOR CAPTURING FINE PARTICLES BY PERCOLATION IN A BED OF GRANULES |
US6248136B1 (en) | 2000-02-03 | 2001-06-19 | Micell Technologies, Inc. | Methods for carbon dioxide dry cleaning with integrated distribution |
US8820316B2 (en) * | 2000-02-11 | 2014-09-02 | Respironics Respiratory Drug Delivery (Uk) Ltd | Drug delivery apparatus |
AU2001263098A1 (en) | 2000-05-12 | 2001-11-26 | Iep Pharmaceutical Devices, Inc. | Powder/liquid metering valve |
US6620351B2 (en) | 2000-05-24 | 2003-09-16 | Auburn University | Method of forming nanoparticles and microparticles of controllable size using supercritical fluids with enhanced mass transfer |
AU2001285242A1 (en) * | 2000-09-08 | 2002-03-22 | Ferro Corporation | Controlled-release pharmaceuticals prepared by supercritical fluid processing techniques |
ES2223034T3 (en) * | 2001-02-26 | 2005-02-16 | Dompe S.P.A. | APPARATUS AND METHOD FOR THE FORMATION OF MICRONIC AND SUBMICRONIC PARTICLES. |
US20030044514A1 (en) * | 2001-06-13 | 2003-03-06 | Richard Robert E. | Using supercritical fluids to infuse therapeutic on a medical device |
US7276184B2 (en) * | 2001-07-12 | 2007-10-02 | Eastman Kodak Company | Surfactant assisted nanomaterial generation process |
ES2261782T3 (en) * | 2001-10-10 | 2006-11-16 | Boehringer Ingelheim Pharmaceuticals Inc. | DUST TREATMENT WITH PRESSURIZED GASEOUS FLUIDS. |
US20030157031A1 (en) * | 2002-02-08 | 2003-08-21 | Lalit Chordia | Method of and apparatus for forming and administering fine particles |
EP1572915A4 (en) * | 2002-04-11 | 2011-01-05 | Medimmune Vaccines Inc | Preservation of bioactive materials by spray drying |
US8313760B2 (en) * | 2002-05-24 | 2012-11-20 | Angiotech International Ag | Compositions and methods for coating medical implants |
WO2003099346A2 (en) * | 2002-05-24 | 2003-12-04 | Angiotech International Ag | Compositions and methods for coating medical implants |
US20060002862A1 (en) * | 2002-12-17 | 2006-01-05 | Medimmune Vaccines, Inc. | High pressure spray-dry of bioactive materials |
AU2004293075A1 (en) * | 2003-11-20 | 2005-06-09 | Angiotech International Ag | Soft tissue implants and anti-scarring agents |
CN1878602A (en) * | 2003-11-28 | 2006-12-13 | 三菱化学株式会社 | Manufacturing method of organic compound particulate |
US20060041248A1 (en) * | 2004-08-23 | 2006-02-23 | Patton David L | Pharmaceutical compositions delivery system and methods |
CA2529427C (en) * | 2004-12-17 | 2011-03-15 | University Of New Brunswick | Synthesis, recharging and processing of hydrogen storage materials using supercritical fluids |
AU2005100176A4 (en) * | 2005-03-01 | 2005-04-07 | Gym Tv Pty Ltd | Garbage bin clip |
WO2007011989A2 (en) * | 2005-07-15 | 2007-01-25 | Map Pharmaceuticals, Inc. | Multiple active pharmaceutical ingredients combined in discrete inhalation particles and formulations thereof |
US8475845B2 (en) * | 2005-07-15 | 2013-07-02 | Map Pharmaceuticals, Inc. | Method of particle formation |
US9010329B2 (en) * | 2009-02-10 | 2015-04-21 | Aerophase | Electronically-controlled, high pressure flow control valve and method of use |
US20100291221A1 (en) * | 2009-05-15 | 2010-11-18 | Robert Owen Cook | Method of administering dose-sparing amounts of formoterol fumarate-budesonide combination particles by inhalation |
US20100298602A1 (en) * | 2009-05-19 | 2010-11-25 | Massachusetts Institute Of Technology | Systems and methods for microfluidic crystallization |
US20100294986A1 (en) * | 2009-05-19 | 2010-11-25 | Massachusetts Institute Of Technology | Supercritical fluid facilitated particle formation in microfluidic systems |
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US10857311B2 (en) | 2010-01-12 | 2020-12-08 | Omega Life Science Ltd. | Method and apparatus for producing fine concentrated aerosol |
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AU2015280412B2 (en) | 2014-06-26 | 2018-07-26 | Island Breeze Systems Ca, Llc | MDI related products and methods of use |
IL292671B2 (en) | 2014-10-13 | 2023-05-01 | Omega Life Science Ltd | Nebulizers |
AU2021207583A1 (en) * | 2020-01-16 | 2022-09-01 | Kindeva Drug Delivery L.P. | Medicinal compositions for carbon dioxide based metered dose inhalers |
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EP0008454A2 (en) * | 1978-08-25 | 1980-03-05 | Bayer Ag | Process for the sterilization of pharmaceutical products |
US4582731A (en) * | 1983-09-01 | 1986-04-15 | Battelle Memorial Institute | Supercritical fluid molecular spray film deposition and powder formation |
WO1990003782A2 (en) * | 1988-10-05 | 1990-04-19 | The Upjohn Company | Finely divided solid crystalline powders via precipitation into an anti-solvent |
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-
1992
- 1992-03-06 US US07/846,331 patent/US5301664A/en not_active Expired - Lifetime
-
1993
- 1993-02-19 CA CA002131393A patent/CA2131393C/en not_active Expired - Fee Related
- 1993-02-19 DE DE69314326T patent/DE69314326T2/en not_active Expired - Fee Related
- 1993-02-19 AT AT93906094T patent/ATE158716T1/en not_active IP Right Cessation
- 1993-02-19 EP EP93906094A patent/EP0627910B1/en not_active Expired - Lifetime
- 1993-02-19 WO PCT/US1993/001501 patent/WO1993017665A1/en active IP Right Grant
- 1993-03-05 MX MX9301246A patent/MX9301246A/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0008454A2 (en) * | 1978-08-25 | 1980-03-05 | Bayer Ag | Process for the sterilization of pharmaceutical products |
US4582731A (en) * | 1983-09-01 | 1986-04-15 | Battelle Memorial Institute | Supercritical fluid molecular spray film deposition and powder formation |
WO1990003782A2 (en) * | 1988-10-05 | 1990-04-19 | The Upjohn Company | Finely divided solid crystalline powders via precipitation into an anti-solvent |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
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US5639441A (en) * | 1992-03-06 | 1997-06-17 | Board Of Regents Of University Of Colorado | Methods for fine particle formation |
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Also Published As
Publication number | Publication date |
---|---|
CA2131393A1 (en) | 1993-09-16 |
EP0627910B1 (en) | 1997-10-01 |
EP0627910A1 (en) | 1994-12-14 |
MX9301246A (en) | 1993-09-01 |
ATE158716T1 (en) | 1997-10-15 |
DE69314326T2 (en) | 1998-04-09 |
CA2131393C (en) | 2002-05-28 |
DE69314326D1 (en) | 1997-11-06 |
US5301664A (en) | 1994-04-12 |
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