WO1991016068A1 - Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs - Google Patents

Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs Download PDF

Info

Publication number
WO1991016068A1
WO1991016068A1 PCT/US1991/002804 US9102804W WO9116068A1 WO 1991016068 A1 WO1991016068 A1 WO 1991016068A1 US 9102804 W US9102804 W US 9102804W WO 9116068 A1 WO9116068 A1 WO 9116068A1
Authority
WO
WIPO (PCT)
Prior art keywords
drug
water
lecithin
phospholipid
lipid
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.)
Ceased
Application number
PCT/US1991/002804
Other languages
English (en)
French (fr)
Inventor
Duncan H. Haynes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to EP91908933A priority Critical patent/EP0533690B1/en
Priority to DK91908933T priority patent/DK0533690T3/da
Priority to RU9292016352A priority patent/RU2100030C1/ru
Priority to CA002078990A priority patent/CA2078990C/en
Priority to DE69131349T priority patent/DE69131349T2/de
Publication of WO1991016068A1 publication Critical patent/WO1991016068A1/en
Anticipated expiration legal-status Critical
Priority to GR990401915T priority patent/GR3030825T3/el
Ceased legal-status Critical Current

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
    • A61K9/48—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
    • A61K9/5005—Wall or coating material
    • A61K9/5015—Organic compounds, e.g. fats, sugars
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
    • 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
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/55555—Liposomes; Vesicles, e.g. nanoparticles; Spheres, e.g. nanospheres; Polymers

Definitions

  • the formulation must allow injection of sufficient quantities of drug:
  • the formulation must carry the drug at high concentration. As an example, if the highest concentration available for a drug is 2% (w/v) or 20 mg/ml and the largest practical volume for an IM injection into man is 5 ml, then a single injection can supply only 100 mg of the drug. If the drug is sufficiently potent, this will present no problem. However, there are many examples in which 1-2 gm of drug must be introduced into the body. This would require either a 10- or 20-fold larger volume (impractical or impossible) or 10-20 times the concentration (heretofore unachievable).
  • diazepam (Valium ) is solublized to a concentration of 5 mg/ml (0.5%) in a solution of 40% propylene glycol, 10% ethyl alcohol, water and preservatives.
  • warnings are given to reduce the possibility of venous thrombosis, phlebitis, local irritation, etc. which are reported under adverse reaction.
  • the preparation is not stable to dilution in water (Roche, 1988 PDR, pp. 1764-1766.
  • a pre-anesthetic sedative product containing 2 mg/ml or 4 mg/ml lorazepam and 0.18 ml/ml polyethylene glycol 400 (non-ionic detergent) in propylene glycol is available for IM injection or IV injection after dilution. It is reported to cause pain and burning with 17% incidence with IM injection (Wyeth, 1988 PDR, pp. 2258-2259).
  • the data for days 1-7 post-injection are compared with results for the same quantity of OTC injected as a commercial 2-methyl-pyrolidone solution.
  • FIG. 4 shows the levels of OTC in central arterial blood in the experiment of Fig. 3.
  • FIG. 7 shows typical time courses of the level anesthesia in rats measured as vocalization threshold (mAmp) to intradermal electrical stimuli after intra-venous injection of lecithin-coated alphaxalone microcrystals.
  • mAmp vocalization threshold
  • my invention makes novel use of membrane -forming lipids as mechanical buffers, organizers of aqueous volume and retardants of recrystallization of the drug. This is achieved by excess phospholipid in the form of unilamellar and multi-lameliar phospholipid vesicles which form a secondary coating of the suspended microcrystal. Predominantly unilamellar vesicles are formed as a byproduct of the sonication and primary coating process. Their retention in the preparation was found to improve the long-term stability of the formulation.
  • the drug microcrystals exhibit only restricted Brownian Motion. Under microscopic observation they are not observed to change position in relation to eachother. They vibrate or "dance in place” about their central position. This partial restriction of motion is probably an important factor in the long-term stability of the preparation. When stored, concentrated preparations are diluted many thousand-fold into drug-saturated water, the microcrystals retain their micron or sub-micron size.
  • the aqueous suspension may show advantages for topical application, instillation into the eye.
  • the preparation can deliver drugs by the inhalation route, in the form of either an aqueous suspension or a lyophilized powder. It is also likely that the preparation will be useful for administration of pesticides and in creating high value biocompatible products, as exemplified by suspension of drugs in drinking water (Example 15).
  • OTC oxytetracycline
  • the lecithin-coated OTC microcrystal fraction had the following weight-averaged particle size distribution: 980+460 (SD) nm, 59%; 2,880+400 (SD) nm, 41%.
  • SD weight-averaged particle size distribution
  • Analysis of the preparation by electron microscopy using negative staining corroborated the above findings.
  • Several preparations were made as described above and were filled into rubber-stoppered glass ampules and glass bottles. With storage over a period of weeks some settling was observed, but the preparation could be rendered homogeneous with three inversions. The preparation retained its properties, including size distribution, OTC concentration, chemical integrity and syringability (20 gauge or narrower) for over 9 months.
  • lecithin-coated microparticles from a material with a melting point below the boiling point of water and above that of the intended temperature of use (37°C).
  • Pharmaceutically acceptable waxes and solids, of biological and synthetic origin include but not limited to hydrogenated castor oil, cetostearyl alcohol, cetyl alcohol, cetyl esters wax, myristyl alcohol, petrolatum, paraffin, and various waxes (emulsifying, microcrystalline, white, yellow, etc.). It is also possible to use these materials to provide a waxy coating for the drug microcrystals, which is in turn coated with phospholipid. The waxy coating will further slow the rate of release of the drug, thus prolonging its duration of action.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
PCT/US1991/002804 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs Ceased WO1991016068A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP91908933A EP0533690B1 (en) 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs
DK91908933T DK0533690T3 (da) 1990-04-26 1991-04-23 Phospholipid-coatede mikrokrystaller: injicerbare formuleringer af vanduopløselige lægemidler
RU9292016352A RU2100030C1 (ru) 1990-04-26 1991-04-23 Водная суспензия, содержащая микрокристаллы фармакологически активного водонерастворимого лекарственного вещества, покрытые мембранообразующим липидом (варианты), и лиофилизированный препарат водной суспензии
CA002078990A CA2078990C (en) 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs
DE69131349T DE69131349T2 (de) 1990-04-26 1991-04-23 Phospholipid-beschichtete mikrokristalle: injizierbare formulierungen wasserlöslicher arzneimittel
GR990401915T GR3030825T3 (en) 1990-04-26 1999-07-20 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US514,012 1990-04-26
US07/514,012 US5091188A (en) 1990-04-26 1990-04-26 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs

Publications (1)

Publication Number Publication Date
WO1991016068A1 true WO1991016068A1 (en) 1991-10-31

Family

ID=24045456

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/002804 Ceased WO1991016068A1 (en) 1990-04-26 1991-04-23 Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs

Country Status (16)

Country Link
US (2) US5091188A (https=)
EP (1) EP0533690B1 (https=)
JP (1) JP3261129B2 (https=)
KR (1) KR0159114B1 (https=)
AT (1) ATE181234T1 (https=)
AU (1) AU7852891A (https=)
CA (1) CA2078990C (https=)
DE (1) DE69131349T2 (https=)
DK (1) DK0533690T3 (https=)
ES (1) ES2134776T3 (https=)
GR (1) GR3030825T3 (https=)
MX (1) MX25532A (https=)
RU (1) RU2100030C1 (https=)
TW (1) TW203559B (https=)
WO (1) WO1991016068A1 (https=)
ZA (1) ZA913122B (https=)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993015731A1 (en) * 1992-02-14 1993-08-19 Robert Lamb Phosphate derivatives of vitamin e to protect cells from effects of aging and injury
DE4221268A1 (de) * 1992-06-26 1994-01-05 Lancaster Group Ag Verwendung eines Dermatikums zur Unterstützung des Sauerstofftransportes in der Haut
FR2702160A1 (fr) * 1993-03-02 1994-09-09 Biovecteurs As Vecteurs particulaires synthétiques et procédé de préparation.
WO1995001776A1 (de) * 1993-07-03 1995-01-19 Rhone-Poulenc Rorer Gmbh Phospholipidische zusammensetzung sowie verwendung einer derartigen zusammensetzung
EP0795585A1 (de) * 1996-03-11 1997-09-17 Basf Aktiengesellschaft Feinverteilte Carotinoid- und Retinoidsuspensionen und Verfahren zu ihrer Herstellung
WO2000050009A1 (en) * 1999-02-26 2000-08-31 Idexx Laboratories, Inc. Methods for administering pharmacologically active compounds to vertebrates
US6835396B2 (en) 2001-09-26 2004-12-28 Baxter International Inc. Preparation of submicron sized nanoparticles via dispersion lyophilization
US6869617B2 (en) 2000-12-22 2005-03-22 Baxter International Inc. Microprecipitation method for preparing submicron suspensions
US6884436B2 (en) 2000-12-22 2005-04-26 Baxter International Inc. Method for preparing submicron particle suspensions
US6951656B2 (en) 2000-12-22 2005-10-04 Baxter International Inc. Microprecipitation method for preparing submicron suspensions
US6977085B2 (en) 2000-12-22 2005-12-20 Baxter International Inc. Method for preparing submicron suspensions with polymorph control
US6979456B1 (en) 1998-04-01 2005-12-27 Jagotec Ag Anticancer compositions
US7112340B2 (en) 2001-10-19 2006-09-26 Baxter International Inc. Compositions of and method for preparing stable particles in a frozen aqueous matrix
US7193084B2 (en) 2000-12-22 2007-03-20 Baxter International Inc. Polymorphic form of itraconazole
US8067032B2 (en) 2000-12-22 2011-11-29 Baxter International Inc. Method for preparing submicron particles of antineoplastic agents
US8722091B2 (en) 2001-09-26 2014-05-13 Baxter International Inc. Preparation of submicron sized nanoparticles via dispersion lyophilization
EP3178479A1 (en) * 2015-12-08 2017-06-14 Verano Ilac Sanayi Ve Ticaret A.S. An injectable composition of ricobendazole
US9700866B2 (en) 2000-12-22 2017-07-11 Baxter International Inc. Surfactant systems for delivery of organic compounds

Families Citing this family (209)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5705187A (en) * 1989-12-22 1998-01-06 Imarx Pharmaceutical Corp. Compositions of lipids and stabilizing materials
US5399363A (en) * 1991-01-25 1995-03-21 Eastman Kodak Company Surface modified anticancer nanoparticles
AU642066B2 (en) * 1991-01-25 1993-10-07 Nanosystems L.L.C. X-ray contrast compositions useful in medical imaging
US5552160A (en) * 1991-01-25 1996-09-03 Nanosystems L.L.C. Surface modified NSAID nanoparticles
US5464696A (en) * 1992-08-13 1995-11-07 Bracco International B.V. Particles for NMR imaging
US5336507A (en) * 1992-12-11 1994-08-09 Sterling Winthrop Inc. Use of charged phospholipids to reduce nanoparticle aggregation
US20030073642A1 (en) * 1993-02-22 2003-04-17 American Bioscience, Inc. Methods and formulations for delivery of pharmacologically active agents
US20070117862A1 (en) * 1993-02-22 2007-05-24 Desai Neil P Novel formulations of pharmacological agents, methods for the preparation thereof and methods for the use thereof
US5393461A (en) * 1993-10-04 1995-02-28 Rtd Corporation Preparation of stable aqueous emulsions of water-insoluble particles
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
US5747001A (en) * 1995-02-24 1998-05-05 Nanosystems, L.L.C. Aerosols containing beclomethazone nanoparticle dispersions
DE19511276C2 (de) * 1995-03-27 1999-02-18 Immuno Ag Adjuvans auf der Basis kolloidaler Eisenverbindungen
US5788959A (en) 1995-04-24 1998-08-04 University Of Maryland, Baltimore County Drug delivery device and method for employing the same
US5785975A (en) * 1995-06-26 1998-07-28 Research Triangle Pharmaceuticals Adjuvant compositions and vaccine formulations comprising same
US5931809A (en) * 1995-07-14 1999-08-03 Depotech Corporation Epidural administration of therapeutic compounds with sustained rate of release
US5834025A (en) 1995-09-29 1998-11-10 Nanosystems L.L.C. Reduction of intravenously administered nanoparticulate-formulation-induced adverse physiological reactions
ATE386506T1 (de) 1995-10-17 2008-03-15 Jagotec Ag Verabreichung unlöslicher arzneistoffe
US7255877B2 (en) * 1996-08-22 2007-08-14 Jagotec Ag Fenofibrate microparticles
WO1998007414A1 (en) 1996-08-22 1998-02-26 Research Triangle Pharmaceuticals Ltd. Compositions comprising microparticles of water-insoluble substances and method for preparing same
US6465016B2 (en) 1996-08-22 2002-10-15 Research Triangle Pharmaceuticals Cyclosporiine particles
US8137684B2 (en) 1996-10-01 2012-03-20 Abraxis Bioscience, Llc Formulations of pharmacological agents, methods for the preparation thereof and methods for the use thereof
US20070185032A1 (en) * 1996-12-11 2007-08-09 Praecis Pharmaceuticals, Inc. Pharmaceutical formulations for sustained drug delivery
JP4642946B2 (ja) 1996-12-20 2011-03-02 アルザ コーポレイション ゲル組成物および方法
FR2757768B1 (fr) * 1996-12-27 1999-04-02 Biovector Therapeutics Sa Vecteur particulaire homeocharge et composition pharmaceutique ou cosmetique le contenant
KR20000075745A (ko) * 1997-02-27 2000-12-26 가마후라 아키오 의약 조성물
WO1998047492A1 (en) * 1997-04-18 1998-10-29 Vertex Pharmaceuticals Incorporated Nanosized aspartyl protease inhibitors
PT1023050E (pt) * 1997-06-27 2013-12-04 Abraxis Bioscience Llc Novas formulações de agentes farmacológicos, métodos para a sua preparação e métodos para a sua utilização
US20030199425A1 (en) * 1997-06-27 2003-10-23 Desai Neil P. Compositions and methods for treatment of hyperplasia
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
CA2312900A1 (en) * 1997-12-02 1999-06-10 Powderject Vaccines, Inc. Transdermal delivery of particulate vaccine compositions
US20010003580A1 (en) * 1998-01-14 2001-06-14 Poh K. Hui Preparation of a lipid blend and a phospholipid suspension containing the lipid blend
DE69908304T2 (de) * 1998-02-11 2004-02-19 Rtp Pharma Corp. Ungesättigte fettsäure und steroide enthaltende kombinationspräparate zur behandlung von entzündungen
SE9801287D0 (sv) * 1998-04-14 1998-04-14 Astra Ab Incorporation of active substances in carrier matrixes
KR100635456B1 (ko) 1998-05-29 2006-10-18 스키에파마 캐나다 인코포레이티드 열보호화 마이크로입자 조성물 및 그의 말단의 스팀멸균방법
GB9814507D0 (en) * 1998-07-03 1998-09-02 Univ Southampton A method and apparatus for controlling pests
US7343710B2 (en) * 1998-07-03 2008-03-18 I.D.A Limited Method and apparatus for controlling pests
DE69912441T2 (de) 1998-08-19 2004-08-19 Skyepharma Canada Inc., Verdun Injizierbare wässerige propofoldispersionen
NZ511798A (en) * 1998-10-19 2004-01-30 Powderject Vaccines Inc Minimal promoters comprising a promoter not linked to its native enhancer and such minimal promoters linked to an antigen
US6881723B1 (en) 1998-11-05 2005-04-19 Powderject Vaccines, Inc. Nucleic acid constructs
US6180136B1 (en) 1998-11-10 2001-01-30 Idexx Laboratories, Inc. Phospholipid-coated microcrystals for the sustained release of pharmacologically active compounds and methods of their manufacture and use
US7521068B2 (en) * 1998-11-12 2009-04-21 Elan Pharma International Ltd. Dry powder aerosols of nanoparticulate drugs
US20040141925A1 (en) * 1998-11-12 2004-07-22 Elan Pharma International Ltd. Novel triamcinolone compositions
IL143197A0 (en) * 1998-11-20 2002-04-21 Rtp Pharma Inc Dispersible phospholipid stabilized microparticles
US6251886B1 (en) 1998-12-07 2001-06-26 Schering Corporation Methods of using temozolomide in the treatment of cancers
US6682758B1 (en) 1998-12-22 2004-01-27 The United States Of America As Represented By The Department Of Health And Human Services Water-insoluble drug delivery system
KR100359252B1 (ko) * 1999-12-21 2002-11-04 주식회사 엘지생명과학 항원을 포함하는 고체상 미세입자 및 이를 포함하는 제제
DE19901687B4 (de) * 1999-01-18 2006-06-01 Grünenthal GmbH Opioide Analgetika mit kontrollierter Wirkstofffreisetzung
AU3593200A (en) 1999-02-09 2000-08-29 Powderject Vaccines, Inc. (mycobacterium tuberculosis), immunization
US6248363B1 (en) * 1999-11-23 2001-06-19 Lipocine, Inc. Solid carriers for improved delivery of active ingredients in pharmaceutical compositions
US7374779B2 (en) * 1999-02-26 2008-05-20 Lipocine, Inc. Pharmaceutical formulations and systems for improved absorption and multistage release of active agents
US6602719B1 (en) 1999-03-26 2003-08-05 Idexx Laboratories, Inc. Method and device for detecting analytes in fluids
US6551842B1 (en) 1999-03-26 2003-04-22 Idexx Laboratories, Inc. Method and device for detecting analytes in fluids
US6511814B1 (en) 1999-03-26 2003-01-28 Idexx Laboratories, Inc. Method and device for detecting analytes in fluids
US20030236236A1 (en) * 1999-06-30 2003-12-25 Feng-Jing Chen Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs
MXPA02000538A (es) * 1999-07-16 2002-07-02 Unilever Nv Dispersiones grasas fluibles.
IL148247A0 (en) 1999-08-24 2002-09-12 Teva Pharma A vaccine composition and method of using the same
US6592869B2 (en) * 1999-08-24 2003-07-15 Teva Pharmaceutical Industries, Ltd. Vaccine composition and method of using the same
AU7984200A (en) * 1999-09-21 2001-04-24 Skyepharma Canada Inc. Surface modified particulate compositions of biologically active substances
US6919009B2 (en) * 1999-10-01 2005-07-19 Nanoplex Technologies, Inc. Method of manufacture of colloidal rod particles as nanobarcodes
US7225082B1 (en) 1999-10-01 2007-05-29 Oxonica, Inc. Colloidal rod particles as nanobar codes
US20050032226A1 (en) * 1999-10-01 2005-02-10 Natan Michael J. Encoded nanoparticles in paper manufacture
US20040209376A1 (en) * 1999-10-01 2004-10-21 Surromed, Inc. Assemblies of differentiable segmented particles
US7045049B1 (en) 1999-10-01 2006-05-16 Nanoplex Technologies, Inc. Method of manufacture of colloidal rod particles as nanobar codes
US20040178076A1 (en) * 1999-10-01 2004-09-16 Stonas Walter J. Method of manufacture of colloidal rod particles as nanobarcodes
US7196066B1 (en) 1999-11-03 2007-03-27 Powderject Vaccines, Inc. DNA-vaccines based on constructs derived from the genomes of human and animal pathogens
US7732404B2 (en) 1999-12-30 2010-06-08 Dexcel Ltd Pro-nanodispersion for the delivery of cyclosporin
GB0009773D0 (en) * 2000-04-19 2000-06-07 Univ Cardiff Particulate composition
EP1276465B1 (en) 2000-04-20 2014-03-12 Jagotec AG Improved water-insoluble drug particle process
JP4763957B2 (ja) 2000-05-10 2011-08-31 オバン・エナジー・リミテッド メディアミリング
EP1292282A2 (en) 2000-06-16 2003-03-19 RTP Pharma Inc. Improved injectable dispersions of propofol
JP4969761B2 (ja) 2000-08-31 2012-07-04 オバン・エナジー・リミテッド 所望粒度を持つ固体基材の小粒子および第一材料の小粒状物を含む相乗作用性混合物を製造する方法
US6579519B2 (en) * 2000-09-18 2003-06-17 Registrar, University Of Delhi Sustained release and long residing ophthalmic formulation and the process of preparing the same
EP1320362B1 (en) * 2000-09-20 2011-08-31 Jagotec AG Stabilised fibrate microparticles
US8586094B2 (en) * 2000-09-20 2013-11-19 Jagotec Ag Coated tablets
US20040077604A1 (en) 2001-12-19 2004-04-22 Lenard Lichtenberger Method and compositions employing formulations of lecithin oils and nsaids for protecting the gastrointestinal tract and providingenhanced therapeutic activity
US20100173876A1 (en) * 2000-12-19 2010-07-08 The Board Of Regents Of The University Of Texas System Oil-based nsaid compositions and methods for making and using same
CA2431606C (en) * 2000-12-19 2011-07-19 The Board Of Regents Of The University Of Texas System Method and compositions employing formulations of lecithin oils and nsaids for protecting the gastrointestinal tract and providing enhanced therapeutic activity
US20040256749A1 (en) * 2000-12-22 2004-12-23 Mahesh Chaubal Process for production of essentially solvent-free small particles
US20040022862A1 (en) * 2000-12-22 2004-02-05 Kipp James E. Method for preparing small particles
US20030096013A1 (en) * 2000-12-22 2003-05-22 Jane Werling Preparation of submicron sized particles with polymorph control
US20050048126A1 (en) * 2000-12-22 2005-03-03 Barrett Rabinow Formulation to render an antimicrobial drug potent against organisms normally considered to be resistant to the drug
US20030072807A1 (en) * 2000-12-22 2003-04-17 Wong Joseph Chung-Tak Solid particulate antifungal compositions for pharmaceutical use
US20020150615A1 (en) * 2001-02-12 2002-10-17 Howard Sands Injectable pharmaceutical composition comprising microdroplets of a camptothecin
US6497896B2 (en) 2001-02-12 2002-12-24 Supergen, Inc. Method for administering camptothecins via injection of a pharmaceutical composition comprising microdroplets containing a camptothecin
US6509027B2 (en) 2001-02-12 2003-01-21 Supergen, Inc. Injectable pharmaceutical composition comprising coated particles of camptothecin
NZ527408A (en) * 2001-02-22 2005-04-29 Skyepharma Canada Inc Hydroxymethylglutarylcoenzyme A (HMG CoA) reductase inhibitor (or a statin) and a fibrate in a single effective oral dosage form to treat dyslipidaemia and dyslipoproteinaemia
US20020176841A1 (en) * 2001-03-19 2002-11-28 Praecis Pharmaceuticals Inc. Pharmaceutical formulations for sustained release
ATE440593T1 (de) * 2001-03-27 2009-09-15 Phares Pharm Res Nv Verfahren und zusammensetzung zur solubilisierung einer biologisch wirksamen verbindung mit geringer wasserlíslichkeit
AU2002307090A1 (en) * 2001-04-03 2002-10-21 Surromed, Inc. Methods and reagents for multiplexed analyte capture, surface array self-assembly, and analysis of complex biological samples
EP1392245A2 (en) * 2001-04-05 2004-03-03 Universite Laval Process for making protein delivery matrix and uses thereof
GB0114532D0 (en) * 2001-06-14 2001-08-08 Jagotec Ag Novel compositions
US6676958B2 (en) * 2001-06-19 2004-01-13 Advanced Bioadjuvants, Llc Adjuvant composition for mucosal and injection delivered vaccines
US7758890B2 (en) 2001-06-23 2010-07-20 Lyotropic Therapeutics, Inc. Treatment using dantrolene
GB0119480D0 (en) * 2001-08-09 2001-10-03 Jagotec Ag Novel compositions
GB0122318D0 (en) * 2001-09-14 2001-11-07 Novartis Ag Organic compounds
US20030054042A1 (en) * 2001-09-14 2003-03-20 Elaine Liversidge Stabilization of chemical compounds using nanoparticulate formulations
WO2003034988A2 (en) * 2001-10-19 2003-05-01 Idexx Laboratories, Inc. Injectable compositions for the controlled delivery of pharmacologically active compound
US20030129242A1 (en) * 2002-01-04 2003-07-10 Bosch H. William Sterile filtered nanoparticulate formulations of budesonide and beclomethasone having tyloxapol as a surface stabilizer
KR100836035B1 (ko) * 2002-02-19 2008-06-09 (주)아모레퍼시픽 포화 및 불포화 레시틴 함유 나노에멀젼 및 이를 함유하는화장료 조성물
WO2003080027A1 (en) * 2002-03-20 2003-10-02 Elan Pharma International, Ltd. Nanoparticulate compositions of angiogenesis inhibitors
US20080220075A1 (en) * 2002-03-20 2008-09-11 Elan Pharma International Ltd. Nanoparticulate compositions of angiogenesis inhibitors
US7101566B2 (en) * 2002-06-28 2006-09-05 Ethicon, Inc. Polymer coated microparticles for sustained release
US20050169979A1 (en) * 2002-07-03 2005-08-04 Dov Michaeli Liposomal vaccine
US20040247661A1 (en) * 2002-07-03 2004-12-09 Dov Michaeli Liposomal vaccine
US7838034B2 (en) * 2002-07-30 2010-11-23 Grunenthal Gmbh Intravenous pharmaceutical form of administration
WO2004035537A2 (en) 2002-10-16 2004-04-29 Euro-Celtique S.A. Antibodies that bind cell-associated ca 125/o772p and methods of use thereof
RU2331424C2 (ru) * 2002-12-13 2008-08-20 Джеготек Аг Топический состав, содержащий наночастицы спиронолактона
JP2006511525A (ja) * 2002-12-13 2006-04-06 ヤゴテック アーゲー ナノ粒子状スピロノラクトン局所製剤
US7731947B2 (en) * 2003-11-17 2010-06-08 Intarcia Therapeutics, Inc. Composition and dosage form comprising an interferon particle formulation and suspending vehicle
WO2005013919A2 (en) 2003-03-04 2005-02-17 Lyotropic Therapeutics, Inc. Treatment using dantrolene
US20050019556A1 (en) * 2003-06-17 2005-01-27 Surromed, Inc. Labeling and authentication of metal objects
DE10327839A1 (de) * 2003-06-20 2005-01-05 Arvinmeritor Gmbh Fahrzeugdachmodul
US8986736B2 (en) * 2003-06-24 2015-03-24 Baxter International Inc. Method for delivering particulate drugs to tissues
AU2004249172A1 (en) * 2003-06-24 2004-12-29 Baxter International Inc. Specific delivery of drugs to the brain
US20080051373A1 (en) * 2003-07-31 2008-02-28 The Board Of Regents Of The University Of Texas System Parenteral preparations of GI-safer phospholipid-associated anti-inflammatories and methods of preparation and use
US20050049209A1 (en) * 2003-08-06 2005-03-03 Chen Andrew Xian Pharmaceutical compositions for delivering macrolides
JP2005097295A (ja) * 2003-09-01 2005-04-14 Wakunaga Pharmaceut Co Ltd ビタミン安定液剤
AU2004275764B2 (en) 2003-09-22 2010-01-14 Baxter Healthcare S.A. High-pressure sterilization to terminally sterilize pharmaceutical preparations and medical products
US20060003002A1 (en) * 2003-11-03 2006-01-05 Lipocine, Inc. Pharmaceutical compositions with synchronized solubilizer release
JP3903061B2 (ja) * 2003-12-24 2007-04-11 株式会社Ｌｔｔバイオファーマ 薬物を含有するナノ粒子およびその製造方法、ならびに当該ナノ粒子からなる非経口投与用製剤
US20050202094A1 (en) * 2004-01-29 2005-09-15 Werling Jane O. Nanosuspensions of anti-retroviral agents for increased central nervous system delivery
JP2007520555A (ja) * 2004-02-05 2007-07-26 バクスター・インターナショナル・インコーポレイテッド 自己安定化剤の使用により調製された分散剤
EP1730516A1 (en) * 2004-03-30 2006-12-13 Pfizer Products Incorporated Method and device for evaluation of pharmaceutical compositions
US20060009469A1 (en) * 2004-05-28 2006-01-12 Leonore Witchey-Lakshmanan Particulate-stabilized injectable pharmacutical compositions of posaconazole
CN1988887A (zh) * 2004-05-28 2007-06-27 先灵公司 包含泊沙康唑的注射用药物混悬剂
US20060160823A1 (en) * 2004-05-28 2006-07-20 Leonore Witchey-Lakshmanan Particulate-stabilized injectable pharmaceutical compositions of Posaconazole
RU2006144851A (ru) * 2004-06-15 2008-06-20 Бакстер Интернэшнл Инк. (Us) Применение терапевтических средств ex-vivo в виде твердых микрочастиц
US20080171687A1 (en) * 2004-09-16 2008-07-17 Abraxis Bioscience, Inc. Compositions And Methods For The Preparation And Administration Of Poorly Water Soluble Drugs
US11246913B2 (en) 2005-02-03 2022-02-15 Intarcia Therapeutics, Inc. Suspension formulation comprising an insulinotropic peptide
WO2006083761A2 (en) 2005-02-03 2006-08-10 Alza Corporation Solvent/polymer solutions as suspension vehicles
WO2006138202A2 (en) * 2005-06-14 2006-12-28 Baxter International Inc. Pharmaceutical formulations for minimizing drug-drug interactions
US20070134341A1 (en) * 2005-11-15 2007-06-14 Kipp James E Compositions of lipoxygenase inhibitors
AU2007233155B2 (en) 2006-03-29 2012-04-26 Scitech Development Llc Liposomal nanoparticles and other formulations of fenretinide for use in therapy and drug delivery
WO2008054508A2 (en) * 2006-04-13 2008-05-08 Alza Corporation Stable nanosized amorphous drug
KR101106510B1 (ko) 2006-05-30 2012-01-20 인타르시아 세라퓨틱스 인코포레이티드 투피스, 내부채널 삼투압 전달 시스템 유동 조절기
WO2008002485A2 (en) * 2006-06-23 2008-01-03 Alza Corporation Increased amorphous stability of poorly water soluble drugs by nanosizing
ES2405733T3 (es) * 2006-07-26 2013-06-03 The Board Of Regents Of The University Of Texas System Preparaciones parenterales de antiinflamatorios asociados a fosfolípidos GI más seguros y procedimientos de preparación y uso
EP2359808B1 (en) 2006-08-09 2013-05-22 Intarcia Therapeutics, Inc Osmotic delivery systems and piston assemblies
AR063704A1 (es) * 2006-09-14 2009-02-11 Makhteshim Chem Works Ltd Nanoparticulas de pesticida obtenida obtenidas a partir de microemulsiones y nanoemulsiones
EP2061583B1 (en) * 2006-09-14 2019-04-10 Yissum Research Development Company, of The Hebrew University of Jerusalem Organic nanoparticles obtained from microemulsions by solvent evaporation
WO2008065502A1 (en) * 2006-11-29 2008-06-05 Pfizer Products Inc. Pharmaceutical compositions based on a) nanoparticles comprising enteric polymers and b) casein
WO2008080047A2 (en) * 2006-12-23 2008-07-03 Baxter International Inc. Magnetic separation of fine particles from compositions
WO2008125940A2 (en) * 2007-04-17 2008-10-23 Pfizer Products Inc. Nanoparticles comprising non-crystalline drug
WO2008133908A2 (en) 2007-04-23 2008-11-06 Intarcia Therapeutics, Inc. Suspension formulations of insulinotropic peptides and uses thereof
US8703204B2 (en) * 2007-05-03 2014-04-22 Bend Research, Inc. Nanoparticles comprising a cholesteryl ester transfer protein inhibitor and anon-ionizable polymer
WO2008135852A2 (en) * 2007-05-03 2008-11-13 Pfizer Products Inc. Pharmaceutical compositions comprising nanoparticles and casein
US8309129B2 (en) * 2007-05-03 2012-11-13 Bend Research, Inc. Nanoparticles comprising a drug, ethylcellulose, and a bile salt
US8530463B2 (en) * 2007-05-07 2013-09-10 Hale Biopharma Ventures Llc Multimodal particulate formulations
EP2152274A4 (en) * 2007-05-07 2010-07-21 Questor Pharmaceuticals Inc NASAL ADMINISTRATION OF BENZODIAZEPINES
US8426467B2 (en) * 2007-05-22 2013-04-23 Baxter International Inc. Colored esmolol concentrate
US20080292663A1 (en) * 2007-05-22 2008-11-27 Gerber Jay D Adjuvant compositions and methods for delivering vaccines
US8722736B2 (en) * 2007-05-22 2014-05-13 Baxter International Inc. Multi-dose concentrate esmolol with benzyl alcohol
US20080293814A1 (en) * 2007-05-22 2008-11-27 Deepak Tiwari Concentrate esmolol
WO2008149230A2 (en) 2007-06-04 2008-12-11 Pfizer Products Inc. Nanoparticles comprising drug, a non-ionizable cellulosic polymer and tocopheryl polyethylene glycol succinate
EP2162120B1 (en) * 2007-06-04 2016-05-04 Bend Research, Inc Nanoparticles comprising a non-ionizable cellulosic polymer and an amphiphilic non-ionizable block copolymer
US20080319039A1 (en) * 2007-06-25 2008-12-25 Jacqueline Rose Bersch Unit dosage forms of temozolomide
US20100215747A1 (en) * 2007-07-13 2010-08-26 Corey Jay Bloom Nanoparticles comprising ionizable, poorly water soluble cellulosic polymers
CN106310293A (zh) 2007-09-27 2017-01-11 免疫疫苗技术有限公司 在包括连续疏水相的载体中的脂质体在体内输送多核苷酸中的应用
WO2009073216A1 (en) * 2007-12-06 2009-06-11 Bend Research, Inc. Nanoparticles comprising a non-ionizable polymer and an amine-functionalized methacrylate copolymer
EP2231169B1 (en) * 2007-12-06 2016-05-04 Bend Research, Inc. Pharmaceutical compositions comprising nanoparticles and a resuspending material
EP2244783B1 (en) 2008-01-22 2019-12-18 Board Of Regents, The University Of Texas System Volatile anesthetic compositions and methods of use
CA2726861C (en) 2008-02-13 2014-05-27 Intarcia Therapeutics, Inc. Devices, formulations, and methods for delivery of multiple beneficial agents
RU2496482C2 (ru) 2008-03-05 2013-10-27 Бакстер Интернэшнл Инк. Композиции и способы для доставки лекарственных средств
CA2718416C (en) * 2008-03-13 2018-01-02 Mallinckrodt Inc. Multi-function, foot-activated controller for imaging system
US20090258865A1 (en) 2008-03-28 2009-10-15 Hale Biopharma Ventures, Llc Administration of benzodiazepine compositions
WO2009146523A1 (en) 2008-06-05 2009-12-10 Immunovaccine Technologies Inc. Compositions comprising liposomes, an antigen, a polynucleotide and a carrier comprising a continuous phase of a hydrophobic substance
US8173621B2 (en) 2008-06-11 2012-05-08 Gilead Pharmasset Llc Nucleoside cyclicphosphates
GB2460915B (en) * 2008-06-16 2011-05-25 Biovascular Inc Controlled release compositions of agents that reduce circulating levels of platelets and methods therefor
PA8855601A1 (es) 2008-12-23 2010-07-27 Forformidatos de nucleósidos
AU2009329872B2 (en) 2008-12-23 2016-07-07 Gilead Pharmasset Llc Synthesis of purine nucleosides
NZ593649A (en) 2008-12-23 2013-11-29 Gilead Pharmasset Llc Nucleoside analogs
US11304960B2 (en) 2009-01-08 2022-04-19 Chandrashekar Giliyar Steroidal compositions
CN109394689A (zh) * 2009-05-05 2019-03-01 德州大学系统董事会 挥发性麻醉剂的新型制剂及其用于减轻炎症的使用方法
US10952965B2 (en) * 2009-05-15 2021-03-23 Baxter International Inc. Compositions and methods for drug delivery
TWI583692B (zh) 2009-05-20 2017-05-21 基利法瑪席特有限責任公司 核苷磷醯胺
RU2547990C2 (ru) 2009-09-28 2015-04-10 Интарсия Терапьютикс, Инк. Быстрое достижение и/или прекращение существенной стабильной доставки лекарственного средства
UY33310A (es) 2010-03-31 2011-10-31 Pharmasset Inc Sintesis estereoselectiva de activos que contienen fosforo
SG184324A1 (en) 2010-03-31 2012-11-29 Gilead Pharmasset Llc Nucleoside phosphoramidates
US8563530B2 (en) 2010-03-31 2013-10-22 Gilead Pharmassel LLC Purine nucleoside phosphoramidate
US9034858B2 (en) 2010-11-30 2015-05-19 Lipocine Inc. High-strength testosterone undecanoate compositions
US20180153904A1 (en) 2010-11-30 2018-06-07 Lipocine Inc. High-strength testosterone undecanoate compositions
US9358241B2 (en) 2010-11-30 2016-06-07 Lipocine Inc. High-strength testosterone undecanoate compositions
CA2818853A1 (en) 2010-11-30 2012-06-07 Gilead Pharmasset Llc 2'-spirocyclo-nucleosides for use in therapy of hcv or dengue virus
US20120310140A1 (en) 2010-12-01 2012-12-06 Spinal Modulation, Inc. Directed delivery of agents to neural anatomy
US20120148675A1 (en) 2010-12-10 2012-06-14 Basawaraj Chickmath Testosterone undecanoate compositions
US20120208755A1 (en) 2011-02-16 2012-08-16 Intarcia Therapeutics, Inc. Compositions, Devices and Methods of Use Thereof for the Treatment of Cancers
ES2683902T3 (es) 2011-06-14 2018-09-28 Hale Biopharma Ventures, Llc Administración de benzodiacepina
EP2760433B1 (en) 2011-09-29 2023-05-31 PLx Opco Inc. pH DEPENDENT CARRIERS FOR TARGETED RELEASE OF PHARMACEUTICALS ALONG THE GASTROINTESTINAL TRACT, COMPOSITIONS THEREFROM, AND MAKING AND USING SAME
CN113876945A (zh) 2011-10-06 2022-01-04 免疫疫苗技术有限公司 包括激活或增加tlr2活性的佐剂的脂质体组合物及其应用
EP4218808A3 (en) 2012-03-12 2023-08-09 Advanced BioAdjuvants, LLC Adjuvant and vaccine compositions
PL2968214T3 (pl) 2013-03-15 2021-11-02 Newvapogen, Inc. Nowe kompozycje przeciwbólowe
RU2541156C1 (ru) * 2013-07-09 2015-02-10 Общество с ограниченной ответственностью Научно-производственное объединение "Клеточные технологии" Трансдермальное антигельминтное средство на основе кремнийорганических ниосом с альбендазолом
US9498485B2 (en) 2014-08-28 2016-11-22 Lipocine Inc. Bioavailable solid state (17-β)-hydroxy-4-androsten-3-one esters
WO2016033549A2 (en) 2014-08-28 2016-03-03 Lipocine Inc. (17-ß)-3-OXOANDROST-4-EN-17-YL TRIDECANOATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE
US9889085B1 (en) 2014-09-30 2018-02-13 Intarcia Therapeutics, Inc. Therapeutic methods for the treatment of diabetes and related conditions for patients with high baseline HbA1c
RU2730996C2 (ru) 2015-06-03 2020-08-26 Интарсия Терапьютикс, Инк. Системы установки и извлечения имплантата
US20160361322A1 (en) 2015-06-15 2016-12-15 Lipocine Inc. Composition and method for oral delivery of androgen prodrugs
KR102574993B1 (ko) 2016-05-16 2023-09-06 인타르시아 세라퓨틱스 인코포레이티드 글루카곤-수용체 선택적 폴리펩티드 및 이들의 이용 방법
USD840030S1 (en) 2016-06-02 2019-02-05 Intarcia Therapeutics, Inc. Implant placement guide
USD860451S1 (en) 2016-06-02 2019-09-17 Intarcia Therapeutics, Inc. Implant removal tool
US11559530B2 (en) 2016-11-28 2023-01-24 Lipocine Inc. Oral testosterone undecanoate therapy
JP7286542B2 (ja) 2017-01-03 2023-06-05 インターシア セラピューティクス，インコーポレイティド Ｇｌｐ－１受容体アゴニストの持続的投与及び薬物の同時投与を含む方法
US12599562B2 (en) * 2017-11-09 2026-04-14 The Board Of Regents Of The University Of Oklahoma Nanocrystal microparticles of poorly soluble drugs and methods of production and use thereof
WO2020018974A1 (en) 2018-07-20 2020-01-23 Lipocine Inc. Liver disease
JP2023518822A (ja) 2020-03-26 2023-05-08 ピーエルエックス オプコ インコーポレイテッド ｐＨ依存的再構築が可能な医薬キャリア、その製造方法及び使用方法
US11992483B2 (en) 2021-03-31 2024-05-28 Cali Biosciences Us, Llc Emulsions for local anesthetics
JP2024521399A (ja) 2021-06-10 2024-05-31 ニューレリス、インク． 小児患者における発作性障害を治療するための組成物および方法
CN116687847B (zh) * 2023-06-26 2024-03-29 石家庄四药有限公司 一种药物微晶注射液及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4411894A (en) * 1979-06-22 1983-10-25 Hoffmann-La Roche Inc. Pharmaceutical preparations
US4725442A (en) * 1983-06-17 1988-02-16 Haynes Duncan H Microdroplets of water-insoluble drugs and injectable formulations containing same
US4761288A (en) * 1984-09-24 1988-08-02 Mezei Associates Limited Multiphase liposomal drug delivery system

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1502774A (en) * 1974-06-25 1978-03-01 Nat Res Dev Immunological preparations
GB1578776A (en) * 1976-06-10 1980-11-12 Univ Illinois Hemoglobin liposome and method of making the same
US4078052A (en) * 1976-06-30 1978-03-07 The United States Of America As Represented By The Secretary Of Health, Education And Welfare Large unilamellar vesicles (LUV) and method of preparing same
US4298594A (en) * 1978-04-14 1981-11-03 Arthur D. Little, Inc. Xenobiotic delivery vehicles, method of forming them and method of using them
DE2856333C2 (de) * 1978-12-27 1983-09-22 A. Nattermann & Cie GmbH, 5000 Köln Oral einnehmbare Arzneimittel mit entzündungshemmender Wirkung
US4378354A (en) * 1978-12-27 1983-03-29 A. Nattermann & Cie. Gmbh Inflammation-preventing pharmaceutical composition of oral administration
US4421747A (en) * 1978-12-27 1983-12-20 A. Nattermann & Cie. Gmbh Inflammation-preventing pharmaceutical composition of oral administration
DE2914788A1 (de) * 1979-04-11 1980-10-16 Nattermann A & Cie Parenteral applizierbare, stabile arzneimittelloesungen mit entzuendungshemmender wirkung
US4345588A (en) * 1979-04-23 1982-08-24 Northwestern University Method of delivering a therapeutic agent to a target capillary bed
JPS562353A (en) * 1979-06-20 1981-01-12 Ricoh Co Ltd Novel disazo compound and its preparation
AR220263A1 (es) * 1980-02-19 1980-10-15 Bago Lab Sa Procedimiento para obtener una preparacion inyectable de sulfonamida potenciada de baja irritabilidad
US4331654A (en) * 1980-06-13 1982-05-25 Eli Lilly And Company Magnetically-localizable, biodegradable lipid microspheres
US5030453A (en) * 1983-03-24 1991-07-09 The Liposome Company, Inc. Stable plurilamellar vesicles
US4515736A (en) * 1983-05-12 1985-05-07 The Regents Of The University Of California Method for encapsulating materials into liposomes
US4622219A (en) * 1983-06-17 1986-11-11 Haynes Duncan H Method of inducing local anesthesia using microdroplets of a general anesthetic
US4492720A (en) * 1983-11-15 1985-01-08 Benjamin Mosier Method of preparing microspheres for intravascular delivery
US4610868A (en) * 1984-03-20 1986-09-09 The Liposome Company, Inc. Lipid matrix carriers for use in drug delivery systems
JPS60208910A (ja) * 1984-03-31 1985-10-21 Green Cross Corp:The 水難溶性薬物・リン脂質複合体の製造方法
JPS6176414A (ja) * 1984-09-21 1986-04-18 Shionogi & Co Ltd リポソーム製剤の製法
JPH0688911B2 (ja) * 1985-06-06 1994-11-09 国立予防衛生研究所長 インフルエンザワクチン及びその製造方法
JPH0617309B2 (ja) * 1985-11-29 1994-03-09 株式会社ビタミン研究所 アドリアマイシン包埋リポソ−ム製剤
AU7128887A (en) * 1986-02-10 1987-08-25 Liposome Technology, Inc. Controlled-release liposome delivery system
US4803070A (en) * 1986-04-15 1989-02-07 Ribi Immunochem Research Inc. Immunological emulsion adjuvants for polysaccharide vaccines
US4806352A (en) * 1986-04-15 1989-02-21 Ribi Immunochem Research Inc. Immunological lipid emulsion adjuvant
US4806350A (en) * 1986-04-18 1989-02-21 Norden Laboratories, Inc. Vaccine formulation
JPS62278241A (ja) * 1986-05-26 1987-12-03 Shoei Kagaku Kogyo Kk ボンデイングワイヤ
US4776991A (en) * 1986-08-29 1988-10-11 The United States Of America As Represented By The Secretary Of The Navy Scaled-up production of liposome-encapsulated hemoglobin
CA1338736C (fr) * 1986-12-05 1996-11-26 Roger Baurain Microcristaux comportant une substance active presentant une affinite pour les phospholipides, et au moins un phospholipide, procede de preparation
DK175531B1 (da) * 1986-12-15 2004-11-22 Nexstar Pharmaceuticals Inc Leveringsvehikel med amphiphil-associeret aktiv bestanddel
US4839111A (en) * 1987-02-02 1989-06-13 The University Of Tennessee Research Corporation Preparation of solid core liposomes
FR2651680B1 (fr) * 1989-09-14 1991-12-27 Medgenix Group Sa Nouveau procede de preparation de microparticules lipidiques.
GB8921222D0 (en) * 1989-09-20 1989-11-08 Riker Laboratories Inc Medicinal aerosol formulations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4411894A (en) * 1979-06-22 1983-10-25 Hoffmann-La Roche Inc. Pharmaceutical preparations
US4725442A (en) * 1983-06-17 1988-02-16 Haynes Duncan H Microdroplets of water-insoluble drugs and injectable formulations containing same
US4761288A (en) * 1984-09-24 1988-08-02 Mezei Associates Limited Multiphase liposomal drug delivery system

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993015731A1 (en) * 1992-02-14 1993-08-19 Robert Lamb Phosphate derivatives of vitamin e to protect cells from effects of aging and injury
DE4221268A1 (de) * 1992-06-26 1994-01-05 Lancaster Group Ag Verwendung eines Dermatikums zur Unterstützung des Sauerstofftransportes in der Haut
WO1994000109A1 (de) * 1992-06-26 1994-01-06 Lancaster Group Ag Dermatikum zur unterstützung des sauerstofftransportes in der haut
US5637318A (en) * 1992-06-26 1997-06-10 Lancaster Group Ag Dermatological agent for assisting the transport of oxygen in the skin
US6759060B2 (en) 1993-03-02 2004-07-06 Biovector Therapeutics, S.A. Synthetic particulate vectors and preparation process
FR2702160A1 (fr) * 1993-03-02 1994-09-09 Biovecteurs As Vecteurs particulaires synthétiques et procédé de préparation.
WO1994020078A1 (fr) * 1993-03-02 1994-09-15 Biovector Therapeutics Sa Vecteurs particulaires synthetiques et procede de preparation
WO1995001776A1 (de) * 1993-07-03 1995-01-19 Rhone-Poulenc Rorer Gmbh Phospholipidische zusammensetzung sowie verwendung einer derartigen zusammensetzung
EP0795585A1 (de) * 1996-03-11 1997-09-17 Basf Aktiengesellschaft Feinverteilte Carotinoid- und Retinoidsuspensionen und Verfahren zu ihrer Herstellung
US6979456B1 (en) 1998-04-01 2005-12-27 Jagotec Ag Anticancer compositions
WO2000050009A1 (en) * 1999-02-26 2000-08-31 Idexx Laboratories, Inc. Methods for administering pharmacologically active compounds to vertebrates
US7037528B2 (en) 2000-12-22 2006-05-02 Baxter International Inc. Microprecipitation method for preparing submicron suspensions
US6884436B2 (en) 2000-12-22 2005-04-26 Baxter International Inc. Method for preparing submicron particle suspensions
US6951656B2 (en) 2000-12-22 2005-10-04 Baxter International Inc. Microprecipitation method for preparing submicron suspensions
US6977085B2 (en) 2000-12-22 2005-12-20 Baxter International Inc. Method for preparing submicron suspensions with polymorph control
US6869617B2 (en) 2000-12-22 2005-03-22 Baxter International Inc. Microprecipitation method for preparing submicron suspensions
US7193084B2 (en) 2000-12-22 2007-03-20 Baxter International Inc. Polymorphic form of itraconazole
US8067032B2 (en) 2000-12-22 2011-11-29 Baxter International Inc. Method for preparing submicron particles of antineoplastic agents
US9700866B2 (en) 2000-12-22 2017-07-11 Baxter International Inc. Surfactant systems for delivery of organic compounds
US6835396B2 (en) 2001-09-26 2004-12-28 Baxter International Inc. Preparation of submicron sized nanoparticles via dispersion lyophilization
US8722091B2 (en) 2001-09-26 2014-05-13 Baxter International Inc. Preparation of submicron sized nanoparticles via dispersion lyophilization
US7112340B2 (en) 2001-10-19 2006-09-26 Baxter International Inc. Compositions of and method for preparing stable particles in a frozen aqueous matrix
EP3178479A1 (en) * 2015-12-08 2017-06-14 Verano Ilac Sanayi Ve Ticaret A.S. An injectable composition of ricobendazole

Also Published As

Publication number Publication date
DK0533690T3 (da) 1999-11-22
RU2100030C1 (ru) 1997-12-27
GR3030825T3 (en) 1999-11-30
US5091188A (en) 1992-02-25
JPH05507685A (ja) 1993-11-04
DE69131349D1 (de) 1999-07-22
TW203559B (https=) 1993-04-11
ATE181234T1 (de) 1999-07-15
AU7852891A (en) 1991-11-11
CA2078990A1 (en) 1991-10-27
EP0533690B1 (en) 1999-06-16
DE69131349T2 (de) 1999-11-18
EP0533690A1 (en) 1993-03-31
ES2134776T3 (es) 1999-10-16
CA2078990C (en) 2002-06-04
JP3261129B2 (ja) 2002-02-25
USRE35338E (en) 1996-09-24
ZA913122B (en) 1992-04-29
KR0159114B1 (ko) 1998-12-01
MX25532A (es) 1993-10-01
EP0533690A4 (en) 1993-04-14

Similar Documents

Publication Publication Date Title
EP0533690B1 (en) Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs
US5091187A (en) Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs
US5246707A (en) Sustained release delivery of water-soluble bio-molecules and drugs using phospholipid-coated microcrystals, microdroplets and high-concentration liposomes
JP2518605B2 (ja) 水不溶性薬剤を含む微小滴
US5340588A (en) Liposphere carriers of vaccines
Tice et al. Parenteral drug delivery: injectables
Frezard Liposomes: from biophysics to the design of peptide vaccines
JP3233402B2 (ja) 物質の制御送達用のリポスフェア
US4725442A (en) Microdroplets of water-insoluble drugs and injectable formulations containing same
JP3836874B2 (ja) 免疫アジュバントとして少ラメラ脂質小胞を含むワクチン
JP3571717B2 (ja) 粒子、該粒子の製法及びその使用
KR890001882B1 (ko) 스테로이드계 리포좀
US5188837A (en) Lipsopheres for controlled delivery of substances
DE69131709T2 (de) Liposomen enthaltende impfstoffzusammensetzungen
KR100446832B1 (ko) 장벽을 통한 활성성분의 비침습성 도포 또는 운반용 제제를 제조하기 위한 액체 소적
JP2003500365A (ja) 体液性および細胞性免疫応答を増強するための安定性、生体適合性最適化アジュバント（ｓｂａ）
WO1998053799A2 (en) Immunogenic compositions
Lakshmi et al. Ufasomes: A potential vesicular carrier system
JPH0651109B2 (ja) 脂質膜構造体
Southern et al. Parenteral Drug Delivery: Injectables
Singh A Review on Liposome
Crommelin et al. Liposomes

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AT AU BB BG BR CA CH DE DK ES FI GB HU JP KP KR LK LU MC MG MW NL NO RO SD SE SU

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE BF BJ CF CG CH CM DE DK ES FR GA GB GR IT LU ML MR NL SE SN TD TG

WWE Wipo information: entry into national phase

Ref document number: 2078990

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 1991908933

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 1019920702656

Country of ref document: KR

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: 1991908933

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1991908933

Country of ref document: EP