WO2002026216A1 - Preparation pharmaceutique a base d'oxans - Google Patents
Preparation pharmaceutique a base d'oxans Download PDFInfo
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- WO2002026216A1 WO2002026216A1 PCT/FR2001/002980 FR0102980W WO0226216A1 WO 2002026216 A1 WO2002026216 A1 WO 2002026216A1 FR 0102980 W FR0102980 W FR 0102980W WO 0226216 A1 WO0226216 A1 WO 0226216A1
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- WIPO (PCT)
- Prior art keywords
- weight
- parts
- adhesive
- matrix
- matrix device
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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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Definitions
- the present invention relates generally to topical pharmaceutical preparations consisting of the combination of an active ingredient, namely an oxan, and a pharmaceutically acceptable excipient allowing transdermal administration of said active ingredient.
- oxan will denote any imidazoline derivative endowed with antagonistic properties of the ⁇ 2-adrenergic receptors and in particular: idazoxan or 2- (1,4-benzodiosan-2-yl) -2-imidazoline in the form of a free base or hydrochloride (as described in patent GB 2,068,376); alkoxy-idazoxans, i.e. 2- (2-alkoxy-1,4-benzodioxan-2-yl) -2-imidazolines), in particular 2-methoxy- and 2-ethoxy-idazoxan (as described in patent EP 92 328); . fluorinated benzodioxane imidazoline derivatives of formula:
- R represents a linear or branched or cyclized alkyl or alkenyl group comprising 1 to 7 carbon atoms, or a benzyl group
- the fluorine atom can occupy position 5, 6, 7 or 8; (as described in French patent application No. 99 08302).
- 3-dihydroxybenzofuran derivatives disubstituted in position 2 such as efaroxan, i.e. 2- [2- (2-ethyl- 2, 3-dihydroxybenzofuranyl)] -2-imidazoline, or dexefaroxan which can be prepared by the process described in international patent application WO-0002836.
- composition of the pharmaceutical preparations which are the subject of the present invention
- various oxans capable of entering into the composition of the pharmaceutical preparations which are the subject of the present invention can be used in the form of their racemic mixtures, of various enantiomeric forms or mixtures, in the form of free base or else of addition salts of acid with pharmacologically acceptable acids, in particular the hydrochloride.
- the present invention therefore relates to such topical pharmaceutical preparations which can be in various dosage forms, in particular in the form of creams, ointments, gels, aerosol dispensers or film-forming spray, or also in the form of a transdermal matrix device.
- the subject of the present invention is a transdermal pharmaceutical preparation containing as active ingredient efaroxan or 2- [2- (2-ethyl-2, 3-dihydrobenzofuranyl)] -2-imidazoline in base or hydrochloride form, as well as the method of obtaining this preparation.
- the present invention relates to a transdermal device formulated so as to allow the absorption of efaroxan through the skin, the latter making it possible to prolong the therapeutic activity of this molecule.
- the matrix device includes a support, a polymeric adhesive matrix and a protector.
- the transdermal route is a recognized route of administration in order to overcome the drawbacks of the other routes of administration, and in particular in order to allow the progressive installation of regular plasma levels, in the case of repeated administration.
- this route of administration improves the patient's compliance with the treatment, which is more particularly true in the case of patients susceptible to a therapeutic remedy based on efaroxan.
- Efaroxan is a potent and selective antagonist of ⁇ 2-adrenergic receptors, the uses of which therapy could benefit either the treatment of Alzeihmer's disease or that of progressive supranuclear palsy (PSP).
- a sudden rise in plasma levels is capable of causing the occurrence of undesirable effects; in the case of efaroxan, the latter are of the cardiovascular type.
- the present invention relates in particular to a new transdermal galenic form and to its method of preparation.
- the production of adhesive matrix devices for administering oxans, and in particular dexefaroxan in base or hydrochloride form is therefore proposed.
- This invention brings together on the one hand several formulations, and secondly that of their manufacturing process.
- an adhesive device for the systemic administration of dexefaroxan or one of its salts comprising a support, a protector and an active self-adhesive matrix (MAAA) characterized by:
- the adhesive copolymer is composed either of one or more adhesive polyacrylates, or of one or more hydrophilic polymers, or of silicone polymers.
- This adhesive copolymer can be an acrylic adhesive copolymer formed from at least two of the monomers among the products hereinafter designated, acrylic acid, butylacrylate, 2-ethylhexylacrylate, vinylacetate, methylacrylate, glycidylmethacrylate, 2- hydroxyethylacrylate, ethylmethacrylate, n-vinylpyrrolidone, butylmethacrylate, methacrylic esters and dimethylaminoethylmethacrylate.
- the hydrophilic polymer is obtained by combination of polyvinyl alcohol and polyvinylpyrrolidone.
- the plasticizing adjuvant is part either of the family of mineral oils such as glycerol, or of products obtained by polymerization of ethylene and preferably of polyethylene glycol type with a molecular mass of between 200 and 8,000.
- the matrix comprises, for a total of 100 parts by weight: a) 60 to 80 parts by weight of an adhesive and self-crosslinking acrylic copolymer, in the form of a solution at approximately 47.5% w / v of 2-ethylhexylacrylate, glycidylmetacrylate, 2-hydroxyethylacrylate, vinylacetate copolymer and, as crosslinking agent, of polybutyltitanate, said "ready-to-use" adhesive copolymer having a glass transition temperature of -50 ° C; b) 0.5 to 10 parts by weight of polyvidone; c) 5 to 15 parts by weight of dexefaroxan in hydrochloride form; d) 0 to 2 parts by weight of antioxidant; e) 0
- the matrix comprises for a total of 100 parts by weight: a) 60 to 80 parts by weight of an adhesive and self-crosslinking acrylic copolymer, in the form of a solution at around 47.5% w / v of acrylic acid, butylacrylate copolymer,
- the matrix comprises for a total of 100 parts by weight: a) 30 to 60 parts by weight of an adhesive acrylic copolymer, in the form of a solution about 60% w / v of dimethylaminoethyl methacrylate copolymer, methacrylic esters and as a crosslinking agent, succinic acid, and as a plasticizing agent for acetyltributylcitrate; b) 0.5 to 10 parts by weight of polyvidone; c) 5 to 10 parts by weight of dexefaroxan in hydrochloride form; d) 0 to 2 parts by weight of antioxidant; e) 0 to 15 parts by weight of one or more absorption promoters.
- an adhesive acrylic copolymer in the form of a solution about 60% w / v of dimethylaminoethyl methacrylate copolymer, methacrylic esters and as a crosslinking agent, succinic acid, and as a plasticizing agent for acetyl
- the matrix comprises for a total of 100 parts by weight; a) 5 to 20 parts by weight of polyvinyl alcohol; b) 20 to 60 parts by weight of polyvidone; c) 10 to 30 parts by weight of glycerol; d) 10 to 30 parts by weight of polyethylene glycol; e) 5 to 15 parts by weight of dexefaroxan in hydrochloride form; f) 0 to 2 parts by weight of 1 antioxidant; g) 0 to 15 parts by weight of one or more absorption promoters.
- the matrix comprises for a total of 100 parts by weight; a) 70 to 95 parts by weight of silicone polymer; b) 5 to 15 parts by weight of dexefaroxan in hydrochloride form; c) 0 to 2 parts by weight of antioxidant; d) 0 to 15 parts by weight of one or more absorption promoters.
- the topical formulation comprises for a total of 100 parts by weight; a) 5 to 30 parts by weight of polysaccharide polymer; b) 1 to 15 parts by weight of dexefaroxan in hydrochloride form; c) 5 to 30 parts by weight of ethanol; d) 20 to 60 parts by weight of water; e) 0 to 15 parts by weight of one or more absorption promoters.
- the topical formulation comprises for a total of 100 parts by weight: a) 2 to 40 parts by weight of carbomer; b) 1 to 15 parts by weight of dexefaroxan in hydrochloride form; c) 5 to 25 parts by weight of isopropyl alcohol; d) 5 to 25 parts by weight of polyoxyethylene alkyl ether; e) 5 to 25 parts by weight of fatty acid esters; f) 5 to 25 parts by weight of fatty alcohol esters; g) 0 to 15 parts by weight of one or more absorption promoters.
- the matrix device further comprises one or more absorption promoters, preferably selected from alcohols, glycols, polyglycols, amides of the pyrrolidone type and derivatives, surfactants of the nonionic type, polysorbates, alkyl ethers, aryl ethers, poloxamers, saturated or unsaturated fatty acids, with carbon chain between C 5 and C 30 , fatty alcohols, polyglycolysed glycerides, alone or mixed, glycols, propylene glycol or polyglycerol esters, fatty acid esters of the polyol, alkyl glyceryl ether, propylene glycol, glycerin, polyoxyethylene glycerol, polyglycerol, sorbitan, polyoxyethylene sorbitan, polyoxyethylene castor oil, alkyl ether type esters of sugars, derivatives of collagen, terpene essential oils, compounds of the m-diethyltolu
- absorption promoters preferably
- the present invention also relates to a process for the preparation of a transdermal adhesive matrix device involving the implementation of the following successive steps: preparing a premix of active principle in the co-solvent (s) of the adhesive or in an additional solvent manufacturing, in order to obtain either a solution or a dispersion;
- a support film preferably of the polyester silicone type, so as to obtain a layer of thickness between 50 and 100 g / m 2 (expressed in dry weight); dry the coating thus obtained in order to evaporate the manufacturing solvents and allow the crosslinking of the polymers, by progressive drying at a temperature between 50 ° C and 110 ° C, and preferably via different drying modes;
- the present invention also extends in general to the use of an oxan as defined above for the manufacture of a topical pharmaceutical preparation intended for the treatment of lipolysis and obesity or else for the treatment of Alzeihmer's disease, progressive supranuclear palsy (PSP), Parkinson's disease and / or depression.
- a topical pharmaceutical preparation will be used in the form of a cream, ointment, gel, aerosol dispenser or film-forming spray for the treatment of lipolysis and obesity, while for the treatment of Alzeihmer's disease , progressive supranuclear palsy, Parkinson's disease and depression, it will be more readily used with a transdermal matrix device.
- a manufacturing process is also recommended for the preparation of said transdermal matrix system, which involves the succession of the following steps described in more detail: i) preparing a premix of active ingredient in the cosolvent (s) adhesive or in an additional manufacturing solvent; ii) add to the premix i) the necessary quantities of plasticizers and of adhesive or non-adhesive polymers; iii) depositing the mixture directly ii) on a support film preferably of polyester silicone type, so as to obtain a layer of thickness between 50 and 100 g / m 2 (expressed in dry weight); iv) drying the coating thus obtained in order to evaporate the manufacturing solvents and allowing the crosslinking of the polymers, by progressive drying at a temperature between 50 ° C.
- the active ingredient thus present either as a solution or as a molecular dispersion; v) laminate an occlusive film, for example of the polyester type, to the dried coating.
- the following compounds will be used to constitute MAAA, alone or in combination; a) or an acrylic copolymer of low to medium molecular weight, with alcoholic functionality, characterized by the presence of 4 basic monomers such as 2-ethylhexylacrylate, glycidylmethacrylate, 2-hydroxyethylacrylate and vinylacetate.
- This acrylic copolymer (for example DURO-TAK® 387-2516 from the company National Starch & Chemical) is a “ready-to-use” self-crosslinked adhesive available in the form of an organic solution with a theoretical density close to 0.90 g / cm 3 , of relative viscosity between 3.1 and 4.2 and of average viscosity on Brookfield (at 25 ° C, 12 rpm, mobile no.3) between 2,700 and 6,000 mPa.s; b) or an acrylic copolymer of low to medium molecular weight, with carboxylic functionality, characterized by the presence of 4 basic monomers such as acrylic acid, butylacrylate, 2-ethylhexylacrylate and vinyl acetate.
- 4 basic monomers such as acrylic acid, butylacrylate, 2-ethylhexylacrylate and vinyl acetate.
- This acrylic copolymer (for example DURO-TAK® 387-2052 from the company National Starch & Chemical) is a self-crosslinked "ready-to-use" adhesive available in the form of an organic solution with a theoretical density close to 0.92 g / cm 3 , with a relative viscosity between 2.5 and 2.9 and an average viscosity on Brookfield (at 25 ° C, 12 rpm, mobile no.3) between 1,500 and 4,000 mPa.s; c) or a cationic acrylic copolymer, characterized by the presence of monomers of the dimethylaminoethyl methacrylate type and methacrylic esters.
- This acrylic copolymer (for example EUDRAGIT E100® from the company Rohm) is available in the form of a granule, the implementation of which in an organic medium also requires the addition of plasticizers and crosslinking agents.
- the product thus obtained has good adhesion properties, has an average viscosity on Brookfield (at 20 ° C, II / 6) of between 800 and 1000 mPa. s. Its dry matter content is close to 60%; d) either a hydrophilic polyvinylpyrrolidone polymer and more particularly of the l-vinyl-2-pyrrolidone type with a molecular mass of between 30,000 and 1,500,000, or a combination of these same compounds.
- these products are available in the form of hygroscopic powders of different particle size and allow the manufacture of a "dry" matrix whose adhesiveness will develop after prior moistening of the skin and will develop over the time of application.
- these polymers can increase the stability of MAAA by acting on the free volume of acrylic copolymers; e) either a hydrophilic polyvinyl alcohol polymer with a molecular mass of between 30,000 and 200,000 or a combination of these same compounds.
- these products are available in the form of hygroscopic powders, used for their properties of viscosifying agents, nonionic surfactants or film-forming agents. In the present case, they participate in the manufacture of a "dry" matrix, the adhesiveness of which will develop after prior moistening of the skin and will develop during the time of application; f) or a polymer belonging to the group of silicones.
- these products are available in the form of a solution in ethyl acetate, with an average viscosity of between 800 and 1200 mPa.s; g) or a polymer belonging to the family of partially substituted cellulose ethers, such as 1 hydroxyethylcellulose, 1 hydroxypropylcellulose, sodium carboxymethylcellulose or that of polysaccharide gums.
- these products for example RHODIGEL 200 from the company Rhodia
- these products are available in molecular weights between 80,000 and 1,200,000, making it possible to obtain hydroalcoholic gels of variable viscosity; h) or a polymer belonging to the group of carbo ers; these synthetic polymers are obtained by copolymerization of acrylic acid with allylsucrose or allyl ethers of pentaerythritol.
- these carbomers for example CARBOMER 943P from the company BF Goodrich
- adjuvants of the formulation which are suitable according to the invention, mention may be made of the use of hydrophilic plasticizers capable of stabilizing the dispersion of the active principle in the polymers, or of improving the skin tolerance of the transdermal device. Mention may preferably be made of polyethylene glycols as well as glycerol, alone or in combination.
- the support which protects the adhesive matrix may be any support generally used in the formulation of transdermal devices, occlusive and inert with respect to the constituents of the matrix.
- any support generally used for example with thin layers of aluminum, combinations of copolymers of vinyl acetate and ethylene in the form films or foam.
- a polyester support film or a multilayer complex of the low density polyethylene and polyvinylidene chloride type will be used.
- the protector which constitutes the disposable part of the adhesive device before application is generally a product having good cutting properties, inert with respect to the components of the matrix; one of the most frequently used products is paper, polyester, polyvinyl chloride.
- a silicone or fluorinated polyester film will be used which can be cut beforehand in order to facilitate its removal before application.
- the final device will be packaged by a bag type waterproof protection using complex polyethylene-aluminum films, or blister type.
- a variation is also recommended which consists of the presence of antioxidant or sequestering agents, which in the form of adjusted amounts, reinforce the stability of the composition.
- a variation is also recommended which consists of the presence of one or more absorption promoters and / or solubilizing agents, which in the form of adjusted amounts, facilitate skin permeation of the active principle or its solubilization in the adhesive matrix.
- composition comprising:
- composition comprising:
- composition comprising:
- composition comprising: Dexefaxoran hydrochloride 16.6 mg (equivalent to 10% m / m base)
- composition comprising:
- composition comprising:
- composition comprising:
- Figs 1a and 1b represent the quantities released of dexefaroxan base ex vivo from animal skins, respectively in cumulative quantity ( ⁇ g / cm 2 ), and in flow ( ⁇ g / cm 2 / h), in the case of transdermal formulations according to 1 invention.
- the best fluxes obtained at steady state from these formulations are between 5 and 10 ⁇ g / cm 2 / h. Compared to those obtained from a hydroalcoholic solution of the same active principle, they are lower, which is explained by the very different characteristics of the galenical formulation itself. Indeed, as a general rule, the release kinetics are faster from topical gel forms with respect to transdermal forms.
- the flux values obtained more particularly with Examples 2 and 3 according to the invention confirm the possibility of considering a transdermal formulation based on dexefaroxan hydrochloride.
- the amount of dexefaroxan (expressed in base form) administered to humans would be between 0.9 and 1.7 mg.
- FIGS. 2a and 2b represent the quantities released of dexefaroxan base ex vivo from animal skins, respectively in cumulative quantity ( ⁇ g / cm 2 ), and in flow ( ⁇ g / cm 2 / h), in the case of transdermal formulations according to Example 1 of the invention, by comparing different concentrations.
- the flux values obtained more particularly with Example 1 according to the invention confirm the possibility of considering modulating the release of the active principle.
- the quantities released at 24 hours increase significantly depending on the concentration of dexefaroxan.
- ex vivo permeation studies on animal skin are carried out using a reference product whose kinetics constitute "a blank", then after pre-treatment of the skin with the promoter compound.
- FIG. 3 represents the quantities expressed in dexefaroxan base of the cumulative quantities ( ⁇ g / cm 2 ); it involves comparing the reference lot CM586 with or without individual pre-treatment by promoters.
- the ratio of the cumulative quantity at 24 h of the test compared to the reference makes it possible to calculate a permeation index (PI) which reflects the capacity of the product tested to promote the flow expressed in dexefaroxan base; the ranking of the promoters tested in ascending order of this index is as follows; it highlights a more marked effect of polar promoters.
- PI permeation index
- FIG. 4 represents the quantities released of idazoxan base and hydrochloride, ex vivo from animal skins, in the case of hydroalcoholic solutions according to the invention.
- the quantities released at 24 h are significantly greater for the base form of idazoxan, which confirms the good skin permeation potential of this molecule.
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2001292001A AU2001292001A1 (en) | 2000-09-26 | 2001-09-26 | Pharmaceutical oxan preparation |
US10/381,801 US20040022834A1 (en) | 2000-09-26 | 2001-09-26 | Pharmaceutical oxan preparation |
JP2002530046A JP2004509916A (ja) | 2000-09-26 | 2001-09-26 | オキサンに基づく薬剤 |
CA002424949A CA2424949A1 (fr) | 2000-09-26 | 2001-09-26 | Preparation pharmaceutique a base d'oxans |
EP01972214A EP1322298A1 (fr) | 2000-09-26 | 2001-09-26 | Preparation pharmaceutique a base d'oxans |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0012197A FR2814368B1 (fr) | 2000-09-26 | 2000-09-26 | Preparation pharmaceutique a base d'oxans |
FR0012197 | 2000-09-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002026216A1 true WO2002026216A1 (fr) | 2002-04-04 |
WO2002026216A8 WO2002026216A8 (fr) | 2003-01-16 |
Family
ID=8854662
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2001/002980 WO2002026216A1 (fr) | 2000-09-26 | 2001-09-26 | Preparation pharmaceutique a base d'oxans |
Country Status (7)
Country | Link |
---|---|
US (1) | US20040022834A1 (fr) |
EP (1) | EP1322298A1 (fr) |
JP (1) | JP2004509916A (fr) |
AU (1) | AU2001292001A1 (fr) |
CA (1) | CA2424949A1 (fr) |
FR (1) | FR2814368B1 (fr) |
WO (1) | WO2002026216A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7446117B2 (en) | 2002-09-16 | 2008-11-04 | Glaxo Group Limited | Cox-2 inhibiting pyridine derivatives |
US7858114B2 (en) | 2006-05-08 | 2010-12-28 | Teikoku Seiyaku Co., Ltd. | Percutaneous absorption preparations of antidementia drugs |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6654365B2 (ja) * | 2015-06-17 | 2020-02-26 | 日東電工株式会社 | 貼付製剤 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994013285A1 (fr) * | 1992-12-07 | 1994-06-23 | Pierre Fabre Medicament | Utilisation de l'idazoxan et ses derives pour la preparation d'un medicament destine au traitement de la maladie de parkinson et de son evolution |
US5635204A (en) * | 1994-03-04 | 1997-06-03 | Montefiore Medical Center | Method for transdermal induction of anesthesia, analgesia or sedation |
WO1998037870A1 (fr) * | 1997-02-28 | 1998-09-03 | Cygnus, Inc. | Liberation transdermique de medicaments de base par utilisation de systemes adhesifs non polaires et d'agents de solubilisation acides |
WO2001039740A1 (fr) * | 1999-12-01 | 2001-06-07 | Pierre Fabre Dermo-Cosmetique | Nouvelles compositions topiques a base d'idazoxan et de cafeine ou de ses derives solubles et leur utilisation comme amincissant et/ou dans le traitement de la cellulite |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4301783C1 (de) * | 1993-01-23 | 1994-02-03 | Lohmann Therapie Syst Lts | Transdermales therapeutisches System mit Galanthamin als wirksamem Bestandteil |
FR2706303B1 (fr) * | 1993-06-18 | 1995-09-08 | Pf Medicament | Utilisation de l'Efaroxan et de ses dérivés pour la préparation d'un médicament destiné au traitement de la maladie de Parkinson. |
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2000
- 2000-09-26 FR FR0012197A patent/FR2814368B1/fr not_active Expired - Fee Related
-
2001
- 2001-09-26 EP EP01972214A patent/EP1322298A1/fr not_active Withdrawn
- 2001-09-26 JP JP2002530046A patent/JP2004509916A/ja active Pending
- 2001-09-26 US US10/381,801 patent/US20040022834A1/en not_active Abandoned
- 2001-09-26 AU AU2001292001A patent/AU2001292001A1/en not_active Abandoned
- 2001-09-26 CA CA002424949A patent/CA2424949A1/fr not_active Abandoned
- 2001-09-26 WO PCT/FR2001/002980 patent/WO2002026216A1/fr not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994013285A1 (fr) * | 1992-12-07 | 1994-06-23 | Pierre Fabre Medicament | Utilisation de l'idazoxan et ses derives pour la preparation d'un medicament destine au traitement de la maladie de parkinson et de son evolution |
US5635204A (en) * | 1994-03-04 | 1997-06-03 | Montefiore Medical Center | Method for transdermal induction of anesthesia, analgesia or sedation |
WO1998037870A1 (fr) * | 1997-02-28 | 1998-09-03 | Cygnus, Inc. | Liberation transdermique de medicaments de base par utilisation de systemes adhesifs non polaires et d'agents de solubilisation acides |
WO2001039740A1 (fr) * | 1999-12-01 | 2001-06-07 | Pierre Fabre Dermo-Cosmetique | Nouvelles compositions topiques a base d'idazoxan et de cafeine ou de ses derives solubles et leur utilisation comme amincissant et/ou dans le traitement de la cellulite |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7446117B2 (en) | 2002-09-16 | 2008-11-04 | Glaxo Group Limited | Cox-2 inhibiting pyridine derivatives |
US7858114B2 (en) | 2006-05-08 | 2010-12-28 | Teikoku Seiyaku Co., Ltd. | Percutaneous absorption preparations of antidementia drugs |
Also Published As
Publication number | Publication date |
---|---|
FR2814368B1 (fr) | 2004-05-07 |
WO2002026216A8 (fr) | 2003-01-16 |
JP2004509916A (ja) | 2004-04-02 |
EP1322298A1 (fr) | 2003-07-02 |
AU2001292001A1 (en) | 2002-04-08 |
FR2814368A1 (fr) | 2002-03-29 |
CA2424949A1 (fr) | 2002-04-04 |
US20040022834A1 (en) | 2004-02-05 |
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