WO2000059468A1 - Suspension pharmaceutique buvable - Google Patents
Suspension pharmaceutique buvable Download PDFInfo
- Publication number
- WO2000059468A1 WO2000059468A1 PCT/FR2000/000870 FR0000870W WO0059468A1 WO 2000059468 A1 WO2000059468 A1 WO 2000059468A1 FR 0000870 W FR0000870 W FR 0000870W WO 0059468 A1 WO0059468 A1 WO 0059468A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oral pharmaceutical
- agent
- weight
- suspension according
- suspension
- Prior art date
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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/04—Amoebicides
Definitions
- the present invention relates to a drinkable pharmaceutical composition intended for facilitated oral administration.
- the oral administration of solid forms such as tablets can prove difficult or even dangerous for children and the elderly, who prefer chewable tablets, tablets which melt. in the mouth or in a spoon of water, granules, powders, solutions or suspensions
- the active ingredients incorporated in these types of formulations sometimes have a bitter taste which persists for a long time and which cannot be effectively masked by the addition of a sweetener or flavoring agent
- the taste and the taste-flavor are important criteria for the patient's acceptance of the drug
- the active principle is generally coated with a lipid substance, either directly or after having been incorporated into a nucleus
- the lipid substances used are for example a partially hydrogenated vegetable oil (EP 670 722), stearic acid and / or palmitic acid (FR 2 615 101), glyceryl t ⁇ palmitate (EP 664 701), a mixture of glyceryl monostearate and beeswax in the proportions 9 / 1 (EP 769 948)
- the granules containing the active principle are coated with a soluble polymeric membrane at a pH greater than or equal to 5
- the granules also contain 1 to 20% by weight of an acidic compound intended to reduce the dissolution of the membrane in the oral cavity Ibuprofen is an active ingredient with a bitter taste which has been the subject of numerous studies to formulate it in stable compositions in which its taste is masked
- a solution of the prior art consists in coating the granules containing the Ibuprofen with a polymer intended to mask its bitter taste.
- This polymer is for example a phthalate (WO 91/16043), a vinyl acetal (JP 91/83922), a cellulose acetate phthalate (WO 95/05166) or a methacrylic acid copolymer (EP 524 180)
- the disadvantage of these formulations lies in the properties of the polymer used. Indeed, all the polymers of the prior art used to mask the taste of Ibuprofen causes the delayed release of the active principle so that its dissolution profile is modified.
- Another solution of the prior art consists in preparing an aqueous suspension of Ibuprofen.
- This suspension contains either a lipid substance and a surfactant (WO 94/25006, US 5 110 606, WO 96/22762, WO 94/05260), or a suspending agent, such as a polysaccharide (JP 98/182 449) , a mixture of cellulose and xanthan gum (EP 556,057), a mixture of polyethylene glycol and sodium carboxymethylcellulose (US 5,602,182), a mixture of xanthan gum and pregelatinized starch (EP 405,930) xanthan gum, microcrystalline cellulose and carboxymethylcellulose (EP 298 740).
- a suspending agent such as a polysaccharide (JP 98/182 449) , a mixture of cellulose and xanthan gum (EP 556,057), a mixture of polyethylene glycol and sodium carboxymethylcellulose (US 5,602,182), a mixture of xanthan gum and pregelatinized starch (EP 405,930) xanthan
- the object of the present invention is an oral pharmaceutical suspension consisting of a liquid phase in which one or more solid active ingredients is dispersed, characterized in that the soluble fraction of said active ingredient (s) in the liquid phase is less than 10% by weight, preferably 5% by weight, more preferably 1% by weight relative to the weight of the suspension.
- the active principle is in the form of crystals, preferably crystals of dimension less than 500 microns, or formulated in granules or flexible spheroids.
- the granules can be coated with a material intended either to ensure the modified or prolonged release of the active ingredient (s) attached to the center of the granules, or to mask the taste of the said active ingredient (s), or to avoid dissolving the active ingredient (s) in the liquid phase of the suspension.
- the granules and spheroids have a final size of between 50 and 1000 microns, preferably between 200 and 600 microns. They consist of an inert core of size substantially between 100 and 350 microns and of spherical shape to which the active ingredient (s) is applied by means of a binder or by simple absorption if the active ingredients are in solution.
- the granules are for example obtained by mounting the active ingredient (s) on a neutral support, consisting of sugar and starch.
- the assembly can be carried out according to several techniques, such as dusting, spraying a solution, the MELT technique, or any other conventional technology known to those skilled in the art.
- the neutral support coated with active principle is then optionally coated with a polymer film consisting of a single polymer or of a combination of several polymers or a succession of different layers of polymer, depending on the expected effect.
- This step can be carried out using the various excipients and technologies well known to those skilled in the art. It is preferable to use aqueous solvents or the MELT technique.
- Soft spheroids are the subject of applications FR 97 146 31 and FR 97 146 35 not yet published, the content of which is included by reference in the present application.
- thermoplastic excipient has a melting point of between 25 and 100 ° C; it is characterized by a pasty to semi-solid consistency, at 20 ° C. It can be chosen among others from partially hydrogenated oils, beeswax and silicone waxes.
- the polymeric material is preferably an acrylic, vinyl or cellulosic copolymer, to which a plasticizer is optionally added so that its percentage of elongation is greater than 50%.
- the oral pharmaceutical suspension according to the invention advantageously consists of an aqueous liquid phase or consists of a mixture of water with a co-solvent, for example an oil, propylene glycol, glycerin or a sorbitol solution.
- a co-solvent for example an oil, propylene glycol, glycerin or a sorbitol solution.
- the active principle can be chosen without limitation from Ibuprofen, Secnidazoie hydrate, Erythromycin and its derivatives, Paracetamol, Tinidazole and Codeine.
- the pharmaceutical oral suspension according to the invention contains a viscosity agent, a bulking agent and a preservative.
- the viscosity agent is chosen from pharmaceutically acceptable viscosity agents, for example xanthan gum, hydroxypropylmethylcellulose, methylcellulose, carageenane, carboxymethylcellulose, microcrystalline cellulose, polyvinylpyrolidone and carboxyvinyl copolymers.
- the viscosity agent is preferably a carboxyvinyl copolymer, such as Carbopol ®. This viscosity agent has the advantage of being used in small quantities.
- the viscosity agent represents 0.1 to 10%, preferably 0.1 to 2.5%, by weight relative to the weight of the suspension.
- the bulking agent represents 10 to 70%, preferably 30 to 55%, by weight relative to the weight of the suspension.
- the preservative represents 0.05 to 3%, preferably 0.1 to 1%, by weight relative to the weight of the suspension.
- the preservative is chosen from methyl hydroxybenzoates, propyl hydroxybenzoates, alkylparabens and sorbic acid.
- the oral suspension according to the invention may also contain at least one agent chosen from an alkalizing or acidifying agent, a flavoring agent, an antioxidant agent, a surface-active agent, a coloring agent, a stabilizing agent, a lubricating agent. and a sweetener.
- at least one agent chosen from an alkalizing or acidifying agent, a flavoring agent, an antioxidant agent, a surface-active agent, a coloring agent, a stabilizing agent, a lubricating agent. and a sweetener.
- the sweetener is chosen, for example, from natural or synthetic sweeteners such as sorbitol, sucrose, xylitol, aspartame, sodium saccharin, sodium cyclamate and their mixtures.
- the flavoring agent is chosen, for example, from products with a mint, strawberry and banana flavor. It represents 0.1 to 3% by weight relative to the weight of the suspension.
- the dye is for example a pigment with titanium dioxide or with iron oxide
- the lubricating agent is for example talc, aluminum oxide or silica
- the surfactant is for example chosen from sodium lauryl sulfate, polyethylene copolymers, nonionic polyoxypropylene copolymers and their mixtures
- the surfactant preferably represents 0.1 to 10% by weight relative to the weight of the suspension
- the suspension according to the invention is offered to the patient in ready-to-use liquid form or in the form of a reconstitutable powder.
- the reconstitutable powder is prepared by mixing the active principle in the form of crystals, granules or spheroids, and the suspension adjuvant. It can be granulated according to the various conventional granulation techniques well known to those skilled in the art. The powder is then divided into vials or unit sachets The vials are large enough that the amount of water needed for reconstitution can be added
- Example 1 suspension of Ibuprofen crystals.
- a batch corresponding to 300 liters of suspension, ie 2000 vials of 150 ml, is prepared from the following formula
- the content does not vary significantly during filling
- the suspension remains homogeneous Stability tests performed under accelerated conditions
- the suspension is made according to the following formula
- the total parabens representing 0.1% o (w / w) of the suspension are a mixture of three esters of parahydroxybenzoates in the following proportions 73% Methylparaben 16% o Ethylparaben 11% Propylparaben This suspension is subjected to accelerated storage conditions (40 ° C and
- the suspension is stable for six months under these conditions.
- a microbiological test is carried out according to the method described in the European Pharmacopoeia 3rd ed.
- the test meets the criteria of the European Pharmacopoeia 3rd ed
- concentration of 0.1% (w /) in total parabens allows effective protection of the suspension
- microgranules are produced by spraying successive layers of active ingredients and then a coating dispersion enabling the bitterness of the active principle to be masked.
- the Ibuprofene granules titrated at 200 mg / g are added to obtain a suspension at 20 mg / ml of Ibuprofene.
- the syrup is produced according to the previous examples.
- microgranules are prepared as in Example 4.
- the various dry components are mixed for 15 minutes in a cubic mixer.
- the excipients are then granulated by adding purified water to the mixture, for a sufficient time.
- the granules are dried at 35 ° C for 3 hours, then calibrated on a 1.25 mm mesh grid.
- a quantity of sparkiets and granules is added according to the proportion defined in the table above.
- the suspension is prepared by adding water to the bottle. By vigorous stirring, the granules are dispersed in the liquid phase. After 1 to 2 minutes at rest, the suspension is reacted. The granules are then homogeneously distributed in the liquid phase and remain in suspension.
- microgranules are prepared as in Example 1.
- microgranules are prepared as in Example 1.
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pain & Pain Management (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00917140A EP1165043A1 (fr) | 1999-04-06 | 2000-04-06 | Suspension pharmaceutique buvable |
IL14576800A IL145768A0 (en) | 1999-04-06 | 2000-04-06 | Drinkable pharmaceutical solution |
AU38252/00A AU778364B2 (en) | 1999-04-06 | 2000-04-06 | Drinkable pharmaceutical solution |
BR0009551-6A BR0009551A (pt) | 1999-04-06 | 2000-04-06 | Suspensão farmacêutica para beber |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR99/04251 | 1999-04-06 | ||
FR9904251A FR2791888B1 (fr) | 1999-04-06 | 1999-04-06 | Suspension pharmaceutique buvable |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000059468A1 true WO2000059468A1 (fr) | 2000-10-12 |
Family
ID=9544041
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/000870 WO2000059468A1 (fr) | 1999-04-06 | 2000-04-06 | Suspension pharmaceutique buvable |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1165043A1 (fr) |
CN (1) | CN1351488A (fr) |
AU (1) | AU778364B2 (fr) |
BR (1) | BR0009551A (fr) |
FR (1) | FR2791888B1 (fr) |
HU (1) | HUP0200711A3 (fr) |
IL (1) | IL145768A0 (fr) |
WO (1) | WO2000059468A1 (fr) |
ZA (2) | ZA200108116B (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003082243A1 (fr) * | 2002-04-03 | 2003-10-09 | Venus Danilo R | Preparation de suspension orale |
US10335390B2 (en) | 2014-09-05 | 2019-07-02 | Symbiomix Therapeutics, Llc | Secnidazole for use in the treatment of bacterial vaginosis |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1411899B1 (fr) * | 2001-08-01 | 2009-03-11 | Novartis AG | Composition de masquage de gout |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1985003000A1 (fr) * | 1984-01-13 | 1985-07-18 | Battelle Development Corporation | Formulations de dosage liquide a liberation regulee pour produits pharmaceutiques |
EP0378137A2 (fr) * | 1989-01-13 | 1990-07-18 | Kali-Chemie Pharma GmbH | Forme galénique |
EP0413533A1 (fr) * | 1989-08-14 | 1991-02-20 | Eurand America, Incorporated | Microencapsulation, avec dissimulation de goût, de NSAID insoluble dans l'eau |
WO1993012771A1 (fr) * | 1991-12-31 | 1993-07-08 | Abbott Laboratories | Enrobages de prolamine pour masquer le gout de medicaments s'administrant par voie orale |
EP0717992A2 (fr) * | 1994-12-21 | 1996-06-26 | McNEIL-PPC, INC. | Formulations de suspension aqueuses pour applications pharmaceutiques |
WO1996035436A1 (fr) * | 1995-05-09 | 1996-11-14 | The Procter & Gamble Company | Compositions comprenant du bismuth et un ou plusieurs antimicrobiens, pour la prevention et le traitement de troubles gastro-intestinaux |
-
1999
- 1999-04-06 FR FR9904251A patent/FR2791888B1/fr not_active Expired - Fee Related
-
2000
- 2000-04-06 HU HU0200711A patent/HUP0200711A3/hu unknown
- 2000-04-06 AU AU38252/00A patent/AU778364B2/en not_active Ceased
- 2000-04-06 IL IL14576800A patent/IL145768A0/xx unknown
- 2000-04-06 EP EP00917140A patent/EP1165043A1/fr not_active Withdrawn
- 2000-04-06 BR BR0009551-6A patent/BR0009551A/pt not_active IP Right Cessation
- 2000-04-06 CN CN00807589A patent/CN1351488A/zh active Pending
- 2000-04-06 WO PCT/FR2000/000870 patent/WO2000059468A1/fr not_active Application Discontinuation
-
2001
- 2001-10-03 ZA ZA200108116A patent/ZA200108116B/xx unknown
- 2001-10-05 ZA ZA200108206A patent/ZA200108206B/xx unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1985003000A1 (fr) * | 1984-01-13 | 1985-07-18 | Battelle Development Corporation | Formulations de dosage liquide a liberation regulee pour produits pharmaceutiques |
EP0378137A2 (fr) * | 1989-01-13 | 1990-07-18 | Kali-Chemie Pharma GmbH | Forme galénique |
EP0413533A1 (fr) * | 1989-08-14 | 1991-02-20 | Eurand America, Incorporated | Microencapsulation, avec dissimulation de goût, de NSAID insoluble dans l'eau |
WO1993012771A1 (fr) * | 1991-12-31 | 1993-07-08 | Abbott Laboratories | Enrobages de prolamine pour masquer le gout de medicaments s'administrant par voie orale |
EP0717992A2 (fr) * | 1994-12-21 | 1996-06-26 | McNEIL-PPC, INC. | Formulations de suspension aqueuses pour applications pharmaceutiques |
WO1996035436A1 (fr) * | 1995-05-09 | 1996-11-14 | The Procter & Gamble Company | Compositions comprenant du bismuth et un ou plusieurs antimicrobiens, pour la prevention et le traitement de troubles gastro-intestinaux |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003082243A1 (fr) * | 2002-04-03 | 2003-10-09 | Venus Danilo R | Preparation de suspension orale |
US10335390B2 (en) | 2014-09-05 | 2019-07-02 | Symbiomix Therapeutics, Llc | Secnidazole for use in the treatment of bacterial vaginosis |
US10682338B2 (en) | 2014-09-05 | 2020-06-16 | Lupin Inc. | Secnidazole for use in the treatment of bacterial vaginosis |
US10849884B2 (en) | 2014-09-05 | 2020-12-01 | Lupin Inc. | Secnidazole for use in the treatment of bacterial vaginosis |
US10857133B2 (en) | 2014-09-05 | 2020-12-08 | Lupin Inc. | Secnidazole for use in the treatment of bacterial vaginosis |
US11000507B2 (en) | 2014-09-05 | 2021-05-11 | Lupin Inc. | Secnidazole for use in the treatment of bacterial vaginosis |
US11000508B2 (en) | 2014-09-05 | 2021-05-11 | Lupin Inc. | Secnidazole for use in the treatment of trichomoniasis |
US11020377B2 (en) | 2014-09-05 | 2021-06-01 | Lupin Inc. | Secnidazole for use in the treatment of bacterial vaginosis |
US11324721B2 (en) | 2014-09-05 | 2022-05-10 | Lupin Inc. | Secnidazole for use in the treatment of trichomoniasis |
US11602522B2 (en) | 2014-09-05 | 2023-03-14 | Lupin Inc. | Secnidazole for use in the treatment of sexually transmitted infection |
US11684607B2 (en) | 2014-09-05 | 2023-06-27 | Lupin, Inc. | Secnidazole for use in the treatment of bacterial vaginosis |
Also Published As
Publication number | Publication date |
---|---|
AU778364B2 (en) | 2004-12-02 |
IL145768A0 (en) | 2002-07-25 |
ZA200108206B (en) | 2002-12-24 |
ZA200108116B (en) | 2002-09-25 |
FR2791888B1 (fr) | 2004-10-08 |
BR0009551A (pt) | 2002-05-28 |
HUP0200711A2 (hu) | 2002-07-29 |
FR2791888A1 (fr) | 2000-10-13 |
EP1165043A1 (fr) | 2002-01-02 |
HUP0200711A3 (en) | 2003-04-28 |
AU3825200A (en) | 2000-10-23 |
CN1351488A (zh) | 2002-05-29 |
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