WO1996000389A1 - Procede de determination de la quantite de principe actif liberee de preparations solides ou semi-liquides utilisees chez l'homme et chez l'animal - Google Patents
Procede de determination de la quantite de principe actif liberee de preparations solides ou semi-liquides utilisees chez l'homme et chez l'animal Download PDFInfo
- Publication number
- WO1996000389A1 WO1996000389A1 PCT/EP1995/002269 EP9502269W WO9600389A1 WO 1996000389 A1 WO1996000389 A1 WO 1996000389A1 EP 9502269 W EP9502269 W EP 9502269W WO 9600389 A1 WO9600389 A1 WO 9600389A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- test solution
- dosage form
- solid
- membrane bag
- active substance
- Prior art date
Links
- 239000013543 active substance Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 27
- 241001465754 Metazoa Species 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 239000007787 solid Substances 0.000 title description 5
- 239000012085 test solution Substances 0.000 claims abstract description 49
- 239000012528 membrane Substances 0.000 claims abstract description 40
- 238000012360 testing method Methods 0.000 claims abstract description 13
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- 241000282412 Homo Species 0.000 claims abstract description 8
- 239000000243 solution Substances 0.000 claims abstract description 8
- 230000004962 physiological condition Effects 0.000 claims abstract description 6
- 239000002552 dosage form Substances 0.000 claims description 29
- 239000007909 solid dosage form Substances 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 21
- 239000008299 semisolid dosage form Substances 0.000 claims description 18
- 238000005259 measurement Methods 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 10
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 9
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims description 4
- -1 ethyl hydroxypropyl Chemical group 0.000 claims description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 238000004898 kneading Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000896 Ethulose Polymers 0.000 claims description 2
- 239000001856 Ethyl cellulose Substances 0.000 claims description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 2
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920003134 Eudragit® polymer Polymers 0.000 claims description 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 229920003086 cellulose ether Polymers 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229920001249 ethyl cellulose Polymers 0.000 claims description 2
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 2
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 claims description 2
- 230000002572 peristaltic effect Effects 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000001069 triethyl citrate Substances 0.000 claims description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000013769 triethyl citrate Nutrition 0.000 claims description 2
- 150000003673 urethanes Chemical class 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 229920001477 hydrophilic polymer Polymers 0.000 claims 1
- 229920002959 polymer blend Polymers 0.000 claims 1
- 238000002835 absorbance Methods 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 238000001914 filtration Methods 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- 210000004051 gastric juice Anatomy 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229940068196 placebo Drugs 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 229940071117 starch glycolate Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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
- A61K9/009—Sachets, pouches characterised by the material or function of the envelope
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
Definitions
- the invention relates to a method for determining the release of active substance from solid or semi-solid dosage forms for use in humans and animals according to the preamble of claim 1.
- Dosage forms that are to be used on the human or animal organism must be adapted to the physiological conditions prevailing on or in the living organism, for example on the skin or in the gastrointestinal tract, in order, for example, with regard to their dissolution rate and the release behavior of a pharmacological active ingredient to be optimal on the living Organism and the therapeutic requirements to be coordinated.
- analysis regulations e.g. "United States Pharmacopoeia XXII, 1990" have been recommended by the authorities, which are based on the real physiological conditions of the living organism and should allow a comparison of the dosage forms.
- the determination of the dissolution rate and the release of active substance is used, for example, to test different production batches of one dosage form for their similarity.
- Such analyzes are also used regularly for stability tests of dosage forms depending on the storage period and climatic load
- the dosage forms intended for use in humans or animals generally do not only consist of the pure active ingredient, but rather they mostly comprise a relatively large amount of fillers and carriers, auxiliaries or binders etc.
- a method for determining the release of active substance from solid or semi-solid dosage forms for use in humans and animals is to be improved so that the test solution can be analyzed optically reliably and without additional effort. Additional separation stages, filtration or centrifugation steps or other possible cleaning steps should be dispensed with.
- the solid or semi-solid dosage form to be examined is introduced into a test solution which corresponds to the physiological conditions when the dosage form is administered to the human or animal organism;
- the dosage form is dissolved in the test solution under controlled conditions, the active ingredient contained in the dosage form being converted into solution;
- the solid or semi-solid dosage form to be tested is completely covered with a membrane bag that is permeable to the test solution, but which, on the other hand, is water-insoluble components of the dosage form and, if necessary, still essentially retains undissolved active ingredient
- the membrane bag completely envelops the dosage form to be tested and retains impurities in the membrane bag, but allows a largely unhindered inflow and the outflow of the test liquid or test solution.
- the active ingredient contained in the dosage form can be converted into solution without hindrance, while the fillers and carriers, auxiliaries or binders are essentially retained in the membrane bag.
- the membrane bag can be easily removed from the test solution and disposed of. Because the fillers and carriers, auxiliaries or binders contained in the solid or semi-solid dosage form are retained within the membrane bag, this residue can also be checked very easily if necessary.
- the solid or semi-solid dosage form to be tested is made from a hydrophilic material (for water-soluble drugs) or from a membrane bag lipophilic membrane (for lipophilic active substances) coated This allows the most diverse types of solid or semi-solid dosage forms to be investigated by carefully selecting the covering membrane.
- Single or multilayer laminates that are porous or teabag-like are used as materials for the membrane bag, for example.
- the preferred material for the membrane bag is polymeric films, especially films made of cellulose ethers such as methyl or ethyl cellulose, hydroxypropyl cellulose, methyl or ethyl hydroxyethyl cellulose, methyl or ethyl hydroxypropyl cellulose, carboxymethyl cellulose, polyvinyl acetate, polyvinyl pyrrolidone, or copolymer made from polyacrylonitrile, made from copolymeric, polyacrylonitrile several of the polymers mentioned, for example, from copolymers of acrylic and methacrylic acid esters with a low content of quaternary ammonium groups (such as EUDRAGIT® RL 12.5 or RS 12.5 from Röhm Pharma GmbH, Germany), from mixtures of polyvinylpyrrolidone with polyvinyl alcohol, resins based on phthalic anhydride-polyhydroxy alcohol , Urethanes, polyamides or from polyvinyl alcohol.
- cellulose ethers such as
- plasticizers can be added to the film materials. This is particularly advantageous if a test apparatus is used which simulates the peristaltic kneading movements of the gastrointestinal tract.
- the plasticizer ensures that the membrane bag material has sufficient elasticity that the membrane bag does not burst during the simulated kneading movements.
- Glycerol polyethylene glycol fatty acid esters such as polyethylene glycol 400 stearate or polyethylene glycol 2000 stearate, triethyl citrate, diethyl phthalate or diethyl sebacate are preferably added as plasticizers.
- FIG. 2 shows the time course of the release of the active ingredient of the dosage form from FIG. 1 with a membrane bag covering
- the solid or semi-solid dosage forms are tested in a test solution made of synthetic gastric juice.
- the test apparatus and test method used for this corresponds, for example, to the "paddle apparatus” or "United States Pharmacopoeia XX ⁇ , 1990", pages 1577-1583 "Paddle method”.
- a sample identical to the solid dosage form according to Example 1 is first completely encased and sealed with a membrane bag made of polyvinyl alcohol (Moviol 28/99 from Hoechst, Germany) and then the membrane bag with the solid dosage form is added to the test solution and directly via optical Absorption measurement determines the active substance concentration in the test solution, that is, extractions or filtrations are omitted before the actual measurement process, since the test solution remains clear.
- the results of the measurement are shown in FIG. 2.
- Curve C therein shows the active substance release in percent.
- the bar chart display shows the actually measured concentration.
- a squeeze containing 25 mg of active ingredient and 120 mg of polyethylene glycol stearate is placed in a test solution made of synthetic gastric juice. A cloudy mixture with excessive UV extinction is formed. An optical absorption measurement to determine the active substance concentration in the test solution is not possible.
- a squeeze according to Example 3 is first enveloped and sealed with a membrane bag made of polyvinyl alcohol.
- the membrane bag with the dosage form contained therein is used in synthetic gastric juice.
- the test solution remains clear and is subjected directly to an optical absorption measurement in order to determine the active ingredient concentration in the test solution over time ( one measurement every two hours).
- the material release curves of three such samples are designated D, E and F.
- the curve shape corresponds qualitatively to the curve shapes from FIGS. 1 and 2.
- the membrane bag completely envelops the dosage form to be tested and retains impurities in the membrane bag, but allows a largely unimpeded inflow and the outflow of the test liquid or the test solution.
- the active ingredient contained in the dosage form can be converted into solution without hindrance, while the fillers and carriers, auxiliaries or binders are essentially retained in the membrane bag.
- the concentration of the released active ingredient in the test solution can be determined directly, lengthy filtration, extractions and chromatographic preparation of the test solution are unnecessary.
- the test equipment remains free and free from grease or other water-insoluble substances.
- the membrane bag can be easily removed from the test solution and disposed of. Because the fillers and carriers, auxiliaries or binders contained in the solid or semi-solid dosage form are retained within the membrane bag, this residue can also be checked very easily if necessary.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Medicinal Preparation (AREA)
Abstract
L'invention concerne un procédé qui permet de déterminer la quantité de principe actif libérée de préparations utilisées chez l'homme et chez l'animal, selon lequel: - la forme galénique à analyser est introduite dans une solution de contrôle qui reproduit les conditions physiologiques qui régnent au moment où la préparation est libérée dans l'organisme humain ou animal, - la préparation est dissoute dans la solution de contrôle dans des conditions contrôlées, et le principe actif contenu dans la préparation est alors converti en solution, - la solution de contrôle qui contient le principe actif dissous est analysée à intervalles déterminés, l'analyse se présentant de préférence sous forme de mesure optique d'absorption, afin de déterminer à des moments précis la concentration en principe actif d'un volume donné de solution de contrôle; - la préparation à vérifier est entièrement enrobée d'un sachet membranaire perméable à la solution de contrôle, mais qui retient par contre essentiellement les constituants insolubles dans l'eau de la préparation et éventuellement du principe actif qui n'est pas encore dissous.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU27912/95A AU2791295A (en) | 1994-06-24 | 1995-06-12 | Method of determining the amount of active substance released from solid or semi-solid preparations administered to humans or animals |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2030/94-0 | 1994-06-24 | ||
| CH203094 | 1994-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996000389A1 true WO1996000389A1 (fr) | 1996-01-04 |
Family
ID=4224287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/002269 WO1996000389A1 (fr) | 1994-06-24 | 1995-06-12 | Procede de determination de la quantite de principe actif liberee de preparations solides ou semi-liquides utilisees chez l'homme et chez l'animal |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2791295A (fr) |
| WO (1) | WO1996000389A1 (fr) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2304327A1 (fr) * | 1975-03-19 | 1976-10-15 | Procter & Gamble | Article a liberation controlee |
| FR2391721A1 (fr) * | 1977-05-23 | 1978-12-22 | Alza Corp | Systemes en copolyesters segmentes pour apporter des substances a un milieu environnant |
| US4207890A (en) * | 1977-01-04 | 1980-06-17 | Mcneilab, Inc. | Drug-dispensing device and method |
| EP0071170A2 (fr) * | 1981-07-28 | 1983-02-09 | Hoechst Aktiengesellschaft | Articles sélectivement perméable aux gaz et aux fluides, conformés à partir de copolymères fluorés, et ayant également des propriétés oléophiles et oléophobes |
| EP0164569A2 (fr) * | 1984-05-11 | 1985-12-18 | Koken Co. Ltd. | Composition pour la libération d'un médicament |
| EP0262893A2 (fr) * | 1986-10-02 | 1988-04-06 | Sohrab Darougar | Dispositif d'insertion oculaire |
| EP0307904A1 (fr) * | 1987-09-18 | 1989-03-22 | Ciba-Geigy Ag | Formes à liberation prolongée enrobées |
-
1995
- 1995-06-12 WO PCT/EP1995/002269 patent/WO1996000389A1/fr active Application Filing
- 1995-06-12 AU AU27912/95A patent/AU2791295A/en not_active Abandoned
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2304327A1 (fr) * | 1975-03-19 | 1976-10-15 | Procter & Gamble | Article a liberation controlee |
| US4207890A (en) * | 1977-01-04 | 1980-06-17 | Mcneilab, Inc. | Drug-dispensing device and method |
| FR2391721A1 (fr) * | 1977-05-23 | 1978-12-22 | Alza Corp | Systemes en copolyesters segmentes pour apporter des substances a un milieu environnant |
| EP0071170A2 (fr) * | 1981-07-28 | 1983-02-09 | Hoechst Aktiengesellschaft | Articles sélectivement perméable aux gaz et aux fluides, conformés à partir de copolymères fluorés, et ayant également des propriétés oléophiles et oléophobes |
| EP0164569A2 (fr) * | 1984-05-11 | 1985-12-18 | Koken Co. Ltd. | Composition pour la libération d'un médicament |
| EP0262893A2 (fr) * | 1986-10-02 | 1988-04-06 | Sohrab Darougar | Dispositif d'insertion oculaire |
| EP0307904A1 (fr) * | 1987-09-18 | 1989-03-22 | Ciba-Geigy Ag | Formes à liberation prolongée enrobées |
Non-Patent Citations (1)
| Title |
|---|
| RUDOLF VOIGT; MANFRED BORNSCHEIN: "Lehrbuch der pharmazeutischen Technologie", VERLAG CHEMIE, WEINHEIM, DE; DEERFIELD BEACH, FL, US; BASEL, CH * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2791295A (en) | 1996-01-19 |
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