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WO1996003142A1 - Composition d'apport de medicament utile pour administrer des agents antiviraux par voie orale - Google Patents

Composition d'apport de medicament utile pour administrer des agents antiviraux par voie orale Download PDF

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Publication number
WO1996003142A1
WO1996003142A1 PCT/GB1995/001735 GB9501735W WO9603142A1 WO 1996003142 A1 WO1996003142 A1 WO 1996003142A1 GB 9501735 W GB9501735 W GB 9501735W WO 9603142 A1 WO9603142 A1 WO 9603142A1
Authority
WO
WIPO (PCT)
Prior art keywords
delivery composition
icam
microspheres
chitosan
composition according
Prior art date
Application number
PCT/GB1995/001735
Other languages
English (en)
Inventor
Peter Watts
Lisbeth Illum
Original Assignee
Danbiosyst Uk Limited
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 Danbiosyst Uk Limited filed Critical Danbiosyst Uk Limited
Priority to EP95925947A priority Critical patent/EP0773791A1/fr
Priority to JP8505576A priority patent/JPH10506376A/ja
Priority to GB9700817A priority patent/GB2305606B/en
Priority to AU29886/95A priority patent/AU707462C/en
Publication of WO1996003142A1 publication Critical patent/WO1996003142A1/fr
Priority to NO970252A priority patent/NO970252D0/no
Priority to FI970331A priority patent/FI970331A0/fi

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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
    • A61K9/14—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
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/177—Receptors; Cell surface antigens; Cell surface determinants
    • A61K38/1774—Immunoglobulin superfamily (e.g. CD2, CD4, CD8, ICAM molecules, B7 molecules, Fc-receptors, MHC-molecules)
    • 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
    • A61K9/0043—Nose
    • 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
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals

Definitions

  • the present invention relates to compositions for nasal administration and, more particularly, to compositions for nasal administration of the antiviral agent known as Intercellular Adhesion Molecule 1 (ICAM-1).
  • ICM-1 Intercellular Adhesion Molecule 1
  • Viral infections affecting the nasal cavity such as influenza and rhinoviral infections can be not only unpleasant disease conditions in normal individuals, but in certain "at risk” groups represent a serious threat to health.
  • agents are now available that can be considered as a possible mode of treatment. These include low molecular weight antiviral agents such as Enviroxine, Pirodavir as well as antiviral proteins such as interferon-alpha and sialidase inhibitors (see for example Von Itzstein et al. Nature. 3Ji_i 418, 1993). More recently it has been shown that rhinoviruses attach to tissue via a specific adhesion process and consequently the binding of virus can be prevented using a cell adhesion molecule such as ICAM-1 or its fragments. (Martin et al., A soluble form of intercellular adhesion molecule- 1 inhibits rhinovirus infection, Nature 344, 1990, 70-72).
  • Chitosan as a bioadhesive material to improve the absorption of polar drugs from the nasal cavity and across other mucosal surfaces has been described by Ilium in Topics in Pharmaceutical Science 1991. Editors: Crommellin D.J.A. and Midha, K.K., Stuttgart, Medpharm., 1992. p 71 and in PCT/GB90/00291.
  • Chitosan systems for local application have been described by Partain (US 4946870). He described systems that formed substantive films in contact with topical surfaces. The various examples provided by Partain are intended for application as lotions to the skin. Intranasal administration is mentioned in US 4946870 but no examples of systems that are not film forming in the nasal cavity are declared. It is also noted that in order to form coherent and substantive films the Partain examples contain high quantities of volatile material such as ethanol. This method would be precluded in the nasal application of such systems.
  • bioadhesive to include a material that adheres to the nasal mucosa by chemical or physical binding such as Van der Waals interaction, ionic interaction, hydrogen bonding or by polymer chain entanglement.
  • the adhesion may taken place to the epithelial (cellular) surface or to the mucus overlying that surface.
  • the bioadhesive material is chitosan, preferably as a solution.
  • the chitosan solution may be made in water or any suitable pharmaceutically acceptable buffer system. Phosphate or lactate buffers are especially preferred.
  • the concentration of chitosan in the solution is preferably in the range 0.01 to 50% w/v, more preferably 0.1 to 30%, more preferably 0.1 % to 15% and most preferably 0.2% to 2.0% .
  • Chitosan is deacetylated chitin, or poly-N-acetyl-D-glucosamine. It is available from Protan Laboratories Inc, Redmond, Washington 98052 and, depending on the grade selected, can be soluble in water up to pH 6.0.
  • a 1 % solution of non-water soluble chitosan (Sea Cure) may be made by making a slurry (eg. 2g/ 100ml) in water and adding an equal volume of organic acid (eg 100ml of 2% acetic acid) and stirring vigorously for one hour. Water-soluble chitosan (see Cure + ) may dissolve without organic or inorganic acids being present.
  • Chitosan has previously been used to precipitate proteinaceous material, to make surgical sutures and as an immunostimulant. It has also been employed previously in oral d g formulations in order to improve the dissolution of poorly soluble dmgs (Sawayanagi et al, Chem. Pharm. Bull., 31, 2062-2068 (1983)) or for the sustained release of dmgs (Nagai et al, Proc. Jt. US- Jpn. Semin. Adv. Chitin, Chitosan, Relat. Enzymes, 21-39. Zikakis J.P. (ed), Academic Press. Orlando (1984)) by a process of slow erosion from a hydrated compressed matrix.
  • the bioadhesive material is a plurality of microspheres.
  • the microsphere can be prepared from a suitable material such as starch, starch derivatives, amylodextrin, amylopectin and cross-linked variants thereof, gelatin, albumin, alginate, gellan, hyaluronic acid, chitosan, dextran and dextran derivatives.
  • the microspheres may also comprise ion-exchange materials.
  • derivatives we particularly mean esters and ethers of the parent compound that can be unfunctionalised or functionalised to contain, for example, ionic groupings.
  • Suitable starch derivatives include hydroxyethyl starch, hydroxypropyl starch, carboxymethyl starch, cationic starch, acetylated starch, phosphorylated starch, succinate derivatives or starch and grafted starches.
  • Such starch derivatives are well known and described in the art (for example Modified Starches: Properties and Uses, O.B. Wurzburg, CRC Press Boca Raton (1986)).
  • Suitable dextran derivatives include diethylaminoethyl-dextran (DEAE- dextran), dextran sulphate, dextran methyl-benzylamide sulphonates, dextran methyl-benzylamide carboxylates, carboxymethyl dextran, diphosphonate dextran, dextran hydrazide, palmitoyldextran and dextran phosphate.
  • DEAE- dextran diethylaminoethyl-dextran
  • dextran sulphate dextran methyl-benzylamide sulphonates
  • dextran methyl-benzylamide carboxylates carboxymethyl dextran
  • diphosphonate dextran dextran hydrazide
  • palmitoyldextran and dextran phosphate dextran phosphate.
  • microspheres can be prepared by emulsification procedures or by spray drying. Both are established procedures in pharmaceutical formulation and are familiar to those skilled in the art
  • the dmg-microsphere formulations are prepared as a freeze-dried or spray dried powder system or a physical mixture.
  • the microspheres can be administered by a nasal insufflator or a device that would be normally used for deposition of powders into the lungs but suitably modified for nasal administration. Examples include the Ventolin inhaler (from Glaxo) and the Dura Dry Powder Device (US Patent 5327883). Bespak device (WO935950).
  • the bioadhesive microspheres have the property of swelling in water. This swelling nature leads to a preferential binding to the mucosal surface of the nose thereby leading to improved retention.
  • the degree of swelling should be such that the particle increases its diameter (as measured by a suitable technique such as the light microscope, laser diffractomer) when immersed in water by a factor of at least 1.2 times.
  • the preferable increase in diameter is 1.5 times or greater.
  • albumin microspheres may be made using the water-in-oil emulsification method where a dispersion of albumin is produced in a suitable oil by homogenization techniques or stirring techniques, with the addition if necessary of small amounts of an appropriate surface active agent.
  • microspheres can be hardened by well known cross-linking procedures such as heat treatment or by chemical cross-linking agents.
  • Suitable agents include dialdehydes, including glyoxal, malondialdehyde, succinicaldehyde, adipaldehyde, glutaraldehyde and phthalaldehyde, diketones such as butadione, epichlorohydrin, polyphosphate and borate.
  • Dialdehydes are used to cross-link proteins such as albumin by interaction with amino groups and diketones form schiff bases with amino groups.
  • Epichlorohydrin activates compounds with nucleophiles such as amino or hydroxyl to an epoxide derivative.
  • microspheres were made as follows: Starch Microspheres
  • the content of ICAM-1 in the microsphere formulation is preferably in the range 0.1% to 50% w/w, more preferably 0.5% to 25% and most preferably 1 % to 20% w/w.
  • the bioadhesive material may be a liquid formulation comprising a polymeric material.
  • gellan gum which is the deacetylated form of the extracellular polysaccharide from Pseudomonas elodae.
  • Native/high-acyl gellan is composed of a linear sequence of tetra-saccharide repeating units containing D-glucuronopyranosyl, D-glucopyranosyl and
  • Xanthan is produced by a number of Xanthomonas strains.
  • the polymer backbone made up of (l-*4)-linked /S-D-glucopyranosyl units is identical to that of cellulose.
  • a trisaccharide side chain containing a D-glucoronosyl unit between two D- mannosyl units is attached.
  • the terminal 3-D-mannopyranosyl unit is glycosidically linked to the 0-4 position of the 3-D-glucopyranosyluronic acid unit, which in turn is glycosidically linked to the 0-2 position of an ⁇ -D-mannopyranosyl unit.
  • Carrageenan is a group of linear galactan polysaccharides extracted from red seaweeds of the Gigartinaceae, Hypneaceae, Solieriaceae, Phyllophoraceae and Furcellariaceae families that have an oster sulfate content of 15-40% and contain alternatively (l-*3)- ⁇ -D- and (l-*4)- ⁇ -D- glycosidic linkages.
  • Agar is a hydrophilic colloid extracted from certain marine algae of the class Rhodophyceae where it occurs as a structural carbohydrate in the cell walls (see also Kang and Pettitt: Xanthan, Gellan, Welan and Rhamsan in Industrial gums by Whistler and BeMiller (Eds), Academic Press Inc. London, 1993).
  • Suitable cations include sodium, potassium, magnesium and calcium.
  • the ionic concentration is chosen according to the degree of gelling required, and allowing for the effect that the ionised dmg present may have on gelling.
  • the divalent ions, calcium and magnesium give maximum gel hardness and modulus at molar concentrations approximately one fortieth ( 1 /40) of those required with the monovalent ions, sodium and potassium.
  • a finite concentration of each cation is required to induce gelation.
  • the ionic strength is kept sufficiently low to obtain a low viscosity formulation but sufficiently high to ensure gelation once administration into the nasal cavity where gelation will take place due to the presence of cations int he nasal liquid.
  • the polymeric material will typically be provided in a concentration of from 0.01 % to 20%, preferably 0.05-10%, more preferably 0.1 % - 5 % .
  • the compositions of the invention can also contain any other pharmacologically acceptable, non-toxic ingredients such as preservatives, antioxidants, flavourings, etc. Benzalkonium chloride may be used as a preservative.
  • the ICAM-1 is used in concentrations in the formulation in the range of 0.01 % to 20% w/v, more preferably 0.1 % to 10% w/v and most preferably 0.2% to 5% w/v.
  • the liquid formulations are administered using well-known nasal spray devices. If the formulations are freeze-dried, they can be administered using a nasal insufflator, as for the microsphere preparations.
  • chitosan glutamate (Sea Cure +210). 5ml of water was added to the chitosan which was left to stir overnight.
  • a beaker Into a beaker was weighed 1.36g of potassium diyhydrogen phosphate and 2.80g of sodium chloride. The salts were dissolved in 80ml of water, the solution adjusted to pH 5.7 using 2N NaOH solution and then made to 100ml with water. When the chitosan had dissolved, 5ml of the phosphate buffer solution was added.
  • a small magnetic stirrer bar was added to the vial, and the contents stirred at room temperature for 24 hours to disperse the gellan gum.
  • the flask contents were gently mixed and then left to stand for 30 minutes.
  • the contents of the conical flask were frozen by immersing the flask into liquid nitrogen.
  • the flask was swirled during freezing to obtain a homogeneous mixture.
  • the flask was transferred to a freeze drier and the contents lyophilised for 24 hours.
  • the resulting product was a free flowing powder containing lmg of ICAM/21mg of formulation.
  • the warmed Span/soya oil mixture was removed from the hot-plate and was stirred at 1000 rpm using an overhead stirrer.
  • the 10ml of ICAM/gelatin mixture was added to the stirring oil and stirred at 1000 rpm for 2 minutes.
  • gelatin-IC AM microspheres were recovered by centrifugation, washed with acetone and left to dry at room temperature.
  • the result was a free-flowing powder containing lmg of ICAM/26mg of formulation.
  • the mean diameter of the microspheres was measured, using laser diffraction, to be 50 ⁇ m.
  • An aqueous solution was prepared containing 2. Img/ml ICAM, 1.4mg/ml Mannitol and 0.7mg/ml PBS. The solution was spray-dried at 100°C to form microparticles of approximately 5 ⁇ m size. lOmg of spray dried ICAM and lOOmg of Eldexomer starch microspheres were weighed into a bottle and placed on to a roller mixer for 30 minutes. The resulting formulation consisted of starch microspheres coated with particles of spray-dried ICAM.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Zoology (AREA)
  • Cell Biology (AREA)
  • Oncology (AREA)
  • Otolaryngology (AREA)
  • Virology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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Abstract

Composition d'apport de médicament destinée à l'administration par voie nasale comprenant l'agent antiviral ICAM-1 et une matière bioadhésive. La matière bioadhésive peut être une solution de chitosane, une formulation liquide comprenant une matière polymère ou une pluralité de microsphères bioadhésives. La matière polymère est de préférence de la gomme de gellane ou de l'alginate. Les microsphères peuvent être formées avec l'amidon, du chitosane, de l'acide hyaluronique ou de la gélatine.
PCT/GB1995/001735 1994-07-26 1995-07-24 Composition d'apport de medicament utile pour administrer des agents antiviraux par voie orale WO1996003142A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP95925947A EP0773791A1 (fr) 1994-07-26 1995-07-24 Composition d'apport de medicament utile pour administrer des agents antiviraux par voie orale
JP8505576A JPH10506376A (ja) 1994-07-26 1995-07-24 薬剤移送用組成物および薬剤投与方法
GB9700817A GB2305606B (en) 1994-07-26 1995-07-24 Drug delivery composition for the nasal administration of ICAM-1
AU29886/95A AU707462C (en) 1994-07-26 1995-07-24 Drug delivery composition for the nasal administration of antiviral agents
NO970252A NO970252D0 (no) 1994-07-26 1997-01-21 Blanding for nasal administrering av et medikament
FI970331A FI970331A0 (fi) 1994-07-26 1997-01-27 Lääkkeen antokoostumus virustenvastaisten aineiden nenään toteutettavaa antoa varten

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9414966.3 1994-07-26
GB9414966A GB9414966D0 (en) 1994-07-26 1994-07-26 Pharmaceutical compositions for the nasal administration of antiviral agents

Related Child Applications (2)

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US08776470 A-371-Of-International 1997-03-28
US09/848,600 Continuation US20010053359A1 (en) 1994-07-26 2001-05-03 Drug delivery composition for the nasal administration of antiviral agents

Publications (1)

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WO1996003142A1 true WO1996003142A1 (fr) 1996-02-08

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PCT/GB1995/001735 WO1996003142A1 (fr) 1994-07-26 1995-07-24 Composition d'apport de medicament utile pour administrer des agents antiviraux par voie orale

Country Status (7)

Country Link
EP (1) EP0773791A1 (fr)
JP (1) JPH10506376A (fr)
CA (1) CA2195639A1 (fr)
FI (1) FI970331A0 (fr)
GB (2) GB9414966D0 (fr)
NO (1) NO970252D0 (fr)
WO (1) WO1996003142A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032596A1 (fr) * 1996-03-06 1997-09-12 Boehringer Ingelheim Pharmaceuticals, Inc. Formulation en poudre de molecules a adhesion intracellulaire
EP0833614A1 (fr) * 1995-06-07 1998-04-08 Sri International Systeme et procede de production de microparticules chargees de medicaments
WO1998030207A1 (fr) * 1997-01-14 1998-07-16 Danbiosyst Uk Limited Microparticules a base de chitosane et de gelatine de type a
WO1999022768A1 (fr) * 1997-10-31 1999-05-14 Monsanto Company Composition a liberation lente comprenant des gels a gomme gellane
EP0994700A1 (fr) * 1997-07-18 2000-04-26 Bayer Corporation Procedes d'elimination de solvant residuel dans les compositions medicamenteuses administrees par voie nasale
JP2001524509A (ja) * 1997-12-02 2001-12-04 ウエスト・ファーマシューティカル・サービセズ・ドラッグ・デリバリー・アンド・クリニカル・リサーチ・センター・リミテッド 鼻孔投与用組成物
WO2002000268A1 (fr) * 2000-06-28 2002-01-03 Bristol-Myers Squibb Company Compositions de soins des plaies pulverisables
US6391452B1 (en) 1997-07-18 2002-05-21 Bayer Corporation Compositions for nasal drug delivery, methods of making same, and methods of removing residual solvent from pharmaceutical preparations
GB2378383A (en) * 2001-06-06 2003-02-12 Gursharan Moonga Nasal delivery of pharmaceutical compositions in powder form
WO2005079749A3 (fr) * 2004-02-21 2006-03-23 Cal Res Ct Ltd West Pharmaceut Solution contenant du chitosane
US7132395B1 (en) 1988-09-01 2006-11-07 Bayer Pharmaceuticals Corporation Antiviral methods using human rhinovirus receptor (ICAM-1)
WO2008091588A1 (fr) 2007-01-22 2008-07-31 Targacept, Inc. Administration intranasale, buccale ou sublinguale d'analogues de métanicotine
JP2009079052A (ja) * 1997-04-18 2009-04-16 Archimedes Development Ltd 粘膜表面への改良された薬物供給
DE102008007759A1 (de) 2007-12-04 2009-06-18 Atlantichem Gmbh Mittel zum Verhindern von Verfärbungen beim Waschen von Textilien
US7947257B2 (en) 2003-12-05 2011-05-24 Archimedes Development Limited Method of intranasal administration of granisetron
US8216604B2 (en) 2003-01-10 2012-07-10 Archimedes Development Limited Method of managing or treating pain

Families Citing this family (1)

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RU2185822C2 (ru) * 2000-08-01 2002-07-27 Общество с ограниченной ответственностью "Фармаген" Препарат для лечения и профилактики вирусных заболеваний

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EP0314863A2 (fr) * 1987-11-02 1989-05-10 Baylor College Of Medicine Utilisation du ICAM-1 ou de ses derivés fonctionels pour le traitement des inflammations non spécifiques
EP0362531A1 (fr) * 1988-09-01 1990-04-11 Bayer Corporation Protéine du récepteur du rhinovirus humain, qui inhibe le caractère infectieux du virus
WO1990005522A1 (fr) * 1988-11-17 1990-05-31 Per Prisell Preparation pharmaceutique
WO1991006282A1 (fr) * 1989-11-04 1991-05-16 Danbiosyst Uk Limited Compositions pharmacologiques a particules de taille reduite
WO1993006842A1 (fr) * 1991-10-02 1993-04-15 Boehringer Ingelheim Pharmaceuticals, Inc. Utilisation de molecules d'adhesion intercellulaire et de leurs ligands de liaison dans le traitement de l'asthme
WO1994000485A1 (fr) * 1992-06-22 1994-01-06 Miles Inc. Formes multimeres de la proteine propre au recepteur du rhinovirus humain
WO1994027576A1 (fr) * 1993-05-20 1994-12-08 Danbiosyst Uk Limited Composition d'administration par voie nasale d'un medicament, contenant de la nicotine

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US4946870A (en) * 1986-06-06 1990-08-07 Union Carbide Chemicals And Plastics Company Inc. Delivery systems for pharmaceutical or therapeutic actives

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EP0314863A2 (fr) * 1987-11-02 1989-05-10 Baylor College Of Medicine Utilisation du ICAM-1 ou de ses derivés fonctionels pour le traitement des inflammations non spécifiques
EP0362531A1 (fr) * 1988-09-01 1990-04-11 Bayer Corporation Protéine du récepteur du rhinovirus humain, qui inhibe le caractère infectieux du virus
WO1990005522A1 (fr) * 1988-11-17 1990-05-31 Per Prisell Preparation pharmaceutique
WO1991006282A1 (fr) * 1989-11-04 1991-05-16 Danbiosyst Uk Limited Compositions pharmacologiques a particules de taille reduite
WO1993006842A1 (fr) * 1991-10-02 1993-04-15 Boehringer Ingelheim Pharmaceuticals, Inc. Utilisation de molecules d'adhesion intercellulaire et de leurs ligands de liaison dans le traitement de l'asthme
WO1994000485A1 (fr) * 1992-06-22 1994-01-06 Miles Inc. Formes multimeres de la proteine propre au recepteur du rhinovirus humain
WO1994027576A1 (fr) * 1993-05-20 1994-12-08 Danbiosyst Uk Limited Composition d'administration par voie nasale d'un medicament, contenant de la nicotine

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Title
L. ILLUM: "The nasal delivery of peptides and proteins.", TRENDS IN BIOTECHNOLOGY, vol. 9, no. 8, CAMBRIDGE, GB, pages 284 - 289 *
S MARLIN ET AL.: "A soluble form of intercellular adhesion molecule-1 inhibits rhinovirus infection.", NATURE, vol. 344, 1 March 1990 (1990-03-01), LONDON, GB, pages 70 - 72 *
See also references of EP0773791A1 *

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7132395B1 (en) 1988-09-01 2006-11-07 Bayer Pharmaceuticals Corporation Antiviral methods using human rhinovirus receptor (ICAM-1)
EP0833614A1 (fr) * 1995-06-07 1998-04-08 Sri International Systeme et procede de production de microparticules chargees de medicaments
US7087245B2 (en) 1995-06-07 2006-08-08 Bomberger David C ICAM-1 formulation having controlled-size microparticles
EP0833614A4 (fr) * 1995-06-07 2001-07-11 Stanford Res Inst Int Systeme et procede de production de microparticules chargees de medicaments
WO1997032596A1 (fr) * 1996-03-06 1997-09-12 Boehringer Ingelheim Pharmaceuticals, Inc. Formulation en poudre de molecules a adhesion intracellulaire
WO1998030207A1 (fr) * 1997-01-14 1998-07-16 Danbiosyst Uk Limited Microparticules a base de chitosane et de gelatine de type a
GB2335357A (en) * 1997-01-14 1999-09-22 Danbiosyst Uk Chitosan-gelatin A microparticles
GB2335357B (en) * 1997-01-14 2000-12-13 Danbiosyst Uk Ltd Chitosan-gelatin a microparticles
US6465626B1 (en) 1997-01-14 2002-10-15 West Pharmaceutical Services Drug Delivery And Clincal Research Centre, Limited Pharmaceutical compositions of chitosan with type-A gelatin
JP2009079052A (ja) * 1997-04-18 2009-04-16 Archimedes Development Ltd 粘膜表面への改良された薬物供給
US6391452B1 (en) 1997-07-18 2002-05-21 Bayer Corporation Compositions for nasal drug delivery, methods of making same, and methods of removing residual solvent from pharmaceutical preparations
EP0994700A4 (fr) * 1997-07-18 2000-10-18 Bayer Ag Procedes d'elimination de solvant residuel dans les compositions medicamenteuses administrees par voie nasale
EP0994700A1 (fr) * 1997-07-18 2000-04-26 Bayer Corporation Procedes d'elimination de solvant residuel dans les compositions medicamenteuses administrees par voie nasale
WO1999022768A1 (fr) * 1997-10-31 1999-05-14 Monsanto Company Composition a liberation lente comprenant des gels a gomme gellane
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GB9414966D0 (en) 1994-09-14
EP0773791A1 (fr) 1997-05-21
AU707462B2 (en) 1999-07-08
GB2305606A (en) 1997-04-16
AU2988695A (en) 1996-02-22
NO970252L (no) 1997-01-21
NO970252D0 (no) 1997-01-21
CA2195639A1 (fr) 1996-02-08
GB2305606B (en) 1998-08-05
GB9700817D0 (en) 1997-03-05
FI970331L (fi) 1997-01-27
FI970331A0 (fi) 1997-01-27
JPH10506376A (ja) 1998-06-23

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