LU85290A1 - NEW ORAL SULPIRIDE FORMS FOR SULPIRIDE - Google Patents
NEW ORAL SULPIRIDE FORMS FOR SULPIRIDE Download PDFInfo
- Publication number
- LU85290A1 LU85290A1 LU85290A LU85290A LU85290A1 LU 85290 A1 LU85290 A1 LU 85290A1 LU 85290 A LU85290 A LU 85290A LU 85290 A LU85290 A LU 85290A LU 85290 A1 LU85290 A1 LU 85290A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- sulpiride
- type
- weight
- eudragit
- dosage forms
- Prior art date
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Classifications
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
. _ 1 _ * i L'invention concerne des nouvelles formes galéniques du Sulpiride, utilisables par voie orale, ainsi que leur procédé de préparation.. _ 1 _ * i The invention relates to new galenical forms of Sulpiride, which can be used orally, as well as to the process for their preparation.
Le Sulpiride, de formule développée K- (éthyl-1 pyrrolidinyl-2) œéthyl méthoxy-2 suifamoy1-5 benzamide, est connu corme étant un excellent neuroleptique désinhibiteur, ayant comme indication thérapeutique 1 principale le traitement des psychoses aigîies et chroniques, et ses caractéristiques et ses propriétés sont notamment décrites dans les brevets français n° 1.472.025, 4879 K et 5916 M.Sulpiride, of structural formula K- (1-ethyl-pyrrolidinyl-2) œethyl-2-methoxy-suifamoy1-5 benzamide, is known as being an excellent inhibitory neuroleptic, having as main therapeutic indication 1 the treatment of acute and chronic psychoses, and its characteristics and properties are described in particular in French patents No. 1,472,025, 4,879 K and 5,916 M.
Les médicaments actifs par voie orale contenant du Sulpiride se présentent actuellement sous la forme de comprimés, de gélules ou de solutés buvables : * mais, et les résultats exposés ci-après le démontrent, ces formes actuelles ! nécessitent une pluralité de doses quotidiennes et ont parfois un pourcentage réduit d'absorption par l'organisme. i On a par conséquent cherché à modifier la forme galénique, de façon â ! améliorer de façon sensible son acceptation par les patients, en réduisant Γ i le nombre de prises journalières.Active oral medications containing Sulpiride are currently in the form of tablets, capsules or drinkable solutions: * but, and the results set out below demonstrate this, these current forms! require a plurality of daily doses and sometimes have a reduced percentage of absorption by the body. We have therefore sought to modify the dosage form so as to! significantly improve patient acceptance by reducing par i the number of daily intakes.
La demi-vie plasmatique du principe actif Sulpiride étant d'environ 8 h 30, il apparaît a priori possible de réaliser une forme galénique du produit, ; permettant de réduire la prise journalière moyenne à 2 gélules ou comprimés i par jour, dosés en Sulpiride ä 100 mg par gélules ou comprimés (avec ur.e | prise le matin et une prise le soir), sinon à 1 gélule ou 1 comprimé par t I jour, dosé à 200 mg de Sulpiride.The plasma half-life of the active principle Sulpiride being approximately 8 h 30, it appears a priori possible to produce a galenical form of the product; reducing the average daily intake to 2 capsules or tablets i per day, dosed in Sulpiride at 100 mg per capsule or tablet (with ur.e | taken in the morning and taken in the evening), otherwise to 1 capsule or 1 tablet per t I day, dosed at 200 mg of Sulpiride.
j Pour cela, on a réalise des microgranules a effet prolongé, selon les ! techniques classiques décrites notamment dans les brevets français n° 2.313.915 (Corneille) ou n° 2.453.642 (Labaz). Classiquement, on a utilisé des grains neutres dont la taille était d'environ 0,50 mm de diamètre, et constitués de 25 °Â d'amidon et de 75 % de saccharose, sur lesquels on a projeté en turbine le Sulpiride au moyen d'une solution i j alcoolique de polyvinylpyrrolicone, puis on a appliqué des fibres j. d'enrobage classiques, à base de polymère du type gomme laque, méthacrylates ou éthylcellulose, ce façon a obtenir une cinétique de ’ libération du principe actif Sulpiride in vitro cars des milieux gastriques et intestinaux pré-établie standard, conformement aux spécifications ci-après : “ 1ère heure : libération inférieure à 40 % - 4ème heure : libération inférieure à 75 % ' J - 6ème heure : libération supérieure à 75 % j 1 ^ Τιj For this, microgranules with long-term effect have been produced, according to! classical techniques described in particular in French patents No. 2,313,915 (Corneille) or No. 2,453,642 (Labaz). Conventionally, neutral grains have been used, the size of which was approximately 0.50 mm in diameter, and made up of 25 ° of starch and 75% of sucrose, onto which the Sulpiride has been sprayed using a turbine. an alcoholic solution of polyvinylpyrrolicone, then fibers j were applied. of conventional coatings, based on shellac, methacrylate or ethylcellulose type polymers, this way of obtaining kinetics for the release of the active principle Sulpiride in vitro cars from standard gastric and intestinal mediums, in accordance with the specifications below : “1st hour: release less than 40% - 4th hour: release less than 75% 'D - 6th hour: release more than 75% d 1 ^ Τι
La libération à la première heure est effectuée dans un suc gastrique artificiel ä pH 1,3, à la quatrième heure et § la huitième heure respectivement dans des sucs intestinaux artificiels à pH 4,5 et pH 7. Les conditions opératoires pour étudier la libération du principe actif sont connues et décrites dans les brevets précités.The release at the first hour is carried out in an artificial gastric juice at pH 1.3, at the fourth hour and at the eighth hour respectively in artificial intestinal juices at pH 4.5 and pH 7. The operating conditions for studying the release of the active ingredient are known and described in the aforementioned patents.
On a ensuite réalisé avec ces microgranules des gélules et des comprimés dosés à 100 ng et on a étudié l'absorption du Sulpiride en déterminant les taux plasmatiques circulant du Sulpiride par radio-innunologie, puis on a compare les résultats obtenus avec ceux issus de la forme gélules actuellement sur le marché.Capsules and tablets dosed at 100 ng were then made with these microgranules and the absorption of Sulpiride was studied by determining the circulating plasma levels of Sulpiride by radio-innunology, then the results obtained were compared with those obtained from the form capsules currently on the market.
Les résultats sont consignés dans le tableau A ci-aprês et montrent qu'avec les deux formulations de micrcgranules utilisés (forme I et forme II), la perte en taux de principe actif circulant est trop importante par rapport à ' celui de la forme normale en gélules (forme IV)., pour permettre de réaliser un médicament à effet prolongé efficace.The results are recorded in table A below and show that with the two formulations of microgranules used (form I and form II), the loss in rate of active principle circulating is too great compared to that of the normal form. in capsules (form IV)., to enable an effective long-acting drug to be produced.
A titre indicatif, pour l'homme de l'art, les formes I et II utilisées possédaient les cinétiques suivantes de libération in vitro en milieux artificiels :As an indication, for those skilled in the art, the forms I and II used had the following kinetics of in vitro release in artificial media:
forme I forme IIform I form II
Libération à la première heure dans un milieu de pH : 1,3 20,0 Z 29,2 %First hour release in pH medium: 1.3 20.0 Z 29.2%
Libération à la quatrième heure dans un milieu de pH : 4,5 68,6 % 58,4 %Release at the fourth hour in a pH medium: 4.5 68.6% 58.4%
Libération à la huitième heure dans un milieu de pH : 7 90,8 % 98,2 % ! " Après l'étude d'une série de formulations à effet prolongé qui ont toutes i donné des résultats incompatibles avec l'obtention d'une bonne forme orale bien absorbée, on a eu l'idée de conserver la forme microgranules (grains sensiblement sphériques de diamètre compris entre 0,2 et 2 nnn) qui doit - permettre en pratique une meilleure absorption du principe actif qu'une poudre classique de la gélule ou du comprimé, mais en ayant une cinétique j de libération in vitro beaucoup plus proche de ces formes immédiates, o'ost-a-dire libérant sensiblement 90 Z du principe actif au bout d'une j heure dans un milieu gastrique artificiel de pH 1,3.Release at the eighth hour in a pH medium: 7 90.8% 98.2%! "After studying a series of long-acting formulations which all gave results incompatible with obtaining a good well absorbed oral form, we had the idea of retaining the microgranule form (substantially spherical grains with a diameter of between 0.2 and 2 nnn) which must - in practice allow better absorption of the active principle than a conventional powder of the capsule or tablet, but having a kinetics of release in vitro much closer to these immediate forms, that is to say substantially releasing 90% of the active ingredient after one day in an artificial gastric medium of pH 1.3.
( j i(i
* -"J* - "J
De façon surprenante, les résultats des microgranules selon cette cinétique in vitro ont montre que, en fonction des taux plasmatiques comparatifs, cette forme III constituée de microgranules mis en gélules dosées à 100 mg permet d'obtenir une absorption double de celle obtenue avec les gélules classiques de Sulpiride (forme IV) tout en conservant une durée d'action légèrement supérieure et en réduisant considérablement d'un sujet à l'autre les écarts d'absorption. Cette amélioration de l'absorption du Sulpiride tant au niveau quantitatif qu'au niveau de sa régularité autorise une réduction des doses utilisées et du nombre des prises quotidiennes.Surprisingly, the results of the microgranules according to this kinetics in vitro have shown that, as a function of the comparative plasma levels, this form III consisting of microgranules put in capsules dosed at 100 mg makes it possible to obtain an absorption twice that obtained with the capsules. Sulpiride classics (form IV) while maintaining a slightly longer duration of action and considerably reducing the differences in absorption from one subject to another. This improvement in the absorption of Sulpiride both quantitatively and in terms of its regularity allows a reduction in the doses used and the number of daily doses.
ii
Ces résultats sont exprimés cens le Tableau A, ainsi que par la figure 1, montrant l'évolution des taux plasmatiques circulant exprimés en ng/ml de ! Sulpiride, entre 0 et 32 heures par comparaison entre la forme III et la forme IV.These results are expressed as Table A, as well as in Figure 1, showing the evolution of circulating plasma levels expressed in ng / ml of! Sulpiride, between 0 and 32 hours by comparison between form III and form IV.
Des expérimentations complémentaires au cours desquelles on a fait varier les enrobages externes des microgranules selon l'invention ont permis de déterminer que la forme préférentielle à absorption améliorée du Sulpiride devait répondre sensiblement aux conditions analytiques suivantes de libération in vitro : . 15 minutes : libération comprise entre 35 et 50 % dans un milieu gastrique artificiel de pH 1,3 . 30 minutes : libération comprise entre 60 et 75 % dans un milieu gastrique artificiel de pH 1,3 . 60 minutes : libération comprise entre 80 et 95 % dans un milieu intestinal artificiel de pH A,5 ! On note par ailleurs une libération globale supérieure a 90 % dans un milieu intestinal artificiel de pH 6,9Complementary experiments in which the external coatings of the microgranules according to the invention were varied have made it possible to determine that the preferential improved absorption form of Sulpiride had to respond substantially to the following analytical conditions of release in vitro:. 15 minutes: release between 35 and 50% in an artificial gastric medium of pH 1.3. 30 minutes: release between 60 and 75% in an artificial gastric medium of pH 1.3. 60 minutes: release between 80 and 95% in an artificial intestinal medium of pH A, 5! There is also an overall release greater than 90% in an artificial intestinal medium of pH 6.9
Comme exemple de réalisation, on a indiqué ci-après la formule de fabrication pour 2.500 gélules dosées à 100 sg de la forme III, ainsi que son procédé de fabrication.As an example of embodiment, the manufacturing formula for 2,500 capsules dosed at 100 μg of form III is indicated below, as well as its manufacturing process.
On utilise 50 g de grains neutres constitués d'environ 25 % d'amidon et de 75 % de saccharose, de taille sensiblement égale à 0,50 mm de diamètre, sur lesquels on applique en turbine 250 g de Sulpiride incorporé dans une solution alcoolique (éthanol) de polyvinylpyrrolïdone à 20 %.50 g of neutral grains are used, consisting of approximately 25% starch and 75% sucrose, of size substantially equal to 0.50 mm in diameter, to which 250 g of sulpiride incorporated in an alcoholic solution are applied in a turbine. (ethanol) of 20% polyvinylpyrrolidone.
Après séchage et tamisage, on a appliqué des couches extérieures composées de polymères méthacryliques commercialisés sous le nom d'Eudragit par j la société Rohm et Haas en solutions alcooliques s raison de 4 parties en / poids d'Eudragit type L, pour 1 partie en poids d'Eudragit type RL.After drying and sieving, outer layers were applied composed of methacrylic polymers marketed under the name Eudragit by j the company Rohm and Haas in alcoholic solutions s 4 parts by weight of Eudragit type L, for 1 part by Eudragit type RL weight.
• _ f —• _ f -
On sèche ensuite avec du talc en faibles proportions, jusqu’à l'obtention de microgranules libérant sensiblement 100 % en une heure selon les conditions analytiques définies ci-dessus.It is then dried with talc in small proportions, until microgranules are obtained which release substantially 100% in one hour according to the analytical conditions defined above.
On sèche ensuite à l'étuve à 37°C pendant environ deux jours, puis on termine la couche externe par projection de 40g d'u e solution éthanclicue , à 13,5 % d'Eudragit type RL. Le titre constaté est d'environ 730 r.g de principe actif par gramme de microgranules.Then dried in an oven at 37 ° C for about two days, then the outer layer is terminated by spraying 40g of an ethanclic solution, 13.5% Eudragit type RL. The titre observed is approximately 730 r.g of active principle per gram of microgranules.
Les microgranules ainsi obtenus répondent aux normes de libération in vitro définies ci-dessus, comme étant représentatives ces formes galéniques : nouvelles du Sulpiride selon l'invention.The microgranules thus obtained meet the in vitro release standards defined above, as being representative of these galenical: new forms of the Sulpiride according to the invention.
ii
Leurs stabilités accélérée et naturelle se sont révélées excellentes sans apparition de toxicité potentialisée.Their accelerated and natural stabilities have been shown to be excellent without the appearance of potentiated toxicity.
Ils peuvent être utilisés en gélules, en comprimés ou en suspension, dans | des milieux neutres.They can be used in capsules, tablets or suspension, in | neutral environments.
Bien entendu, l'homme de l'art pourra introduire des variantes, notamment dans les proportions respectives des excipients et du principe actif, la composition des grains neutres et dans la nature des polymères constituant les couches externes, sans pour cela sortir du cadre de l'invention.Of course, those skilled in the art can introduce variants, in particular in the respective proportions of the excipients and of the active principle, the composition of the neutral grains and in the nature of the polymers constituting the external layers, without thereby departing from the scope of the invention.
Claims (6)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8320635A FR2556964A1 (en) | 1983-12-23 | 1983-12-23 | NEW GALENIC FORMS OF SULPIRIDE USED ORALALLY |
FR8320635 | 1983-12-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU85290A1 true LU85290A1 (en) | 1984-10-26 |
Family
ID=9295477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU85290A LU85290A1 (en) | 1983-12-23 | 1984-04-06 | NEW ORAL SULPIRIDE FORMS FOR SULPIRIDE |
Country Status (38)
Country | Link |
---|---|
EP (1) | EP0147244A1 (en) |
JP (1) | JPS60139616A (en) |
KR (1) | KR910004570B1 (en) |
AR (1) | AR231398A1 (en) |
AU (1) | AU569516B2 (en) |
BE (1) | BE899331A (en) |
BG (1) | BG49707A3 (en) |
CH (1) | CH659386A5 (en) |
CZ (1) | CZ262984A3 (en) |
DD (1) | DD220782A5 (en) |
DE (1) | DE3412868A1 (en) |
DK (1) | DK165729C (en) |
ES (1) | ES532125A0 (en) |
FI (1) | FI82603C (en) |
FR (1) | FR2556964A1 (en) |
GB (1) | GB2151920B (en) |
GR (1) | GR79584B (en) |
HU (1) | HU190924B (en) |
IE (1) | IE57164B1 (en) |
IL (1) | IL71470A (en) |
IN (1) | IN160415B (en) |
IS (1) | IS1364B6 (en) |
IT (1) | IT1177655B (en) |
LU (1) | LU85290A1 (en) |
MA (1) | MA20088A1 (en) |
MX (1) | MX7715E (en) |
NO (1) | NO169575C (en) |
NZ (1) | NZ207753A (en) |
OA (1) | OA07700A (en) |
PH (1) | PH21938A (en) |
PL (1) | PL144356B1 (en) |
PT (1) | PT78382B (en) |
RO (1) | RO89437A (en) |
SU (1) | SU1478993A3 (en) |
YU (1) | YU44762B (en) |
ZA (1) | ZA842573B (en) |
ZM (1) | ZM2084A1 (en) |
ZW (1) | ZW6084A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0164959A2 (en) * | 1984-06-04 | 1985-12-18 | Sterwin Ag. | Pharmaceutical composition in sustained release unit dose form and process for its preparation |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0212746B1 (en) * | 1985-08-16 | 1991-04-10 | The Procter & Gamble Company | Drug particles having constant release |
US4853229A (en) * | 1987-10-26 | 1989-08-01 | Alza Corporation | Method for adminstering tiny pills |
JPH0791184B2 (en) * | 1988-03-31 | 1995-10-04 | 田辺製薬株式会社 | Controlled release formulation and process for producing the same |
GB8903328D0 (en) * | 1989-02-14 | 1989-04-05 | Ethical Pharma Ltd | Nifedipine-containing pharmaceutical compositions and process for the preparation thereof |
FR2762213B1 (en) * | 1997-04-18 | 1999-05-14 | Synthelabo | PHARMACEUTICAL COMPOSITION WITH GASTRIC RETENTION |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
FR2313915A1 (en) * | 1976-01-26 | 1977-01-07 | Corneille Gilbert | Sustained release vincamine microcapsules - with inert core, vincamine (deriv.) intermediate layer and microporous outer coating |
US4285665A (en) * | 1978-05-08 | 1981-08-25 | Johnson, Matthey & Co., Limited | Engines |
FR2453639A1 (en) * | 1979-04-09 | 1980-11-07 | Sanofi Sa | NAFTIDROFURYL-BASED IMMEDIATE-DELAYED RELEASE DRUG COMPOSITION |
FR2453642A1 (en) * | 1979-04-12 | 1980-11-07 | Sanofi Sa | Controlled release of ergo-toxin methane sulphonate - from micro-granules coated with anionic and cationic methacrylic! polymers and a plasticiser |
FR2454804B1 (en) * | 1979-04-26 | 1986-11-21 | Sanofi Sa | DIHYDROERGOTOXIN-BASED MEDICINAL PRODUCT AND PROCESS FOR PREPARING THE SAME |
FR2470599A1 (en) * | 1979-12-07 | 1981-06-12 | Panoz Donald | IMPROVEMENTS IN PROCESSES FOR THE PREPARATION OF GALENIC SHAPES WITH DELAYED ACTION AND PROGRAMMED RELEASE AND GALENIC FORMS OF MEDICAMENTS THUS OBTAINED |
SE8003805L (en) * | 1980-05-21 | 1981-11-22 | Haessle Ab | A PHARMACEUTICAL PREPARATION WITH IMPROVED EMISSION PROPERTY |
JPS5753326A (en) * | 1980-09-17 | 1982-03-30 | Dainippon Printing Co Ltd | Manufacture of biaxially stretching blow molded vessel of saturated polyester |
FR2492661A1 (en) * | 1980-10-28 | 1982-04-30 | Laruelle Claude | NOVEL GALENIC FORM OF ADMINISTRATION OF METOCLOPRAMIDE, ITS PREPARATION METHOD AND MEDICINAL PRODUCT COMPRISING THIS NOVEL FORM |
FR2494112B1 (en) * | 1980-11-19 | 1986-01-10 | Laruelle Claude | |
FR2534139B1 (en) * | 1982-10-07 | 1986-08-29 | Laruelle Claude | NOVEL GALENIC FORM OF SULPIRIDE, METHOD FOR PREPARING SAME, AND MEDICINAL PRODUCT COMPRISING THIS NEW FORM |
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1983
- 1983-12-23 FR FR8320635A patent/FR2556964A1/en not_active Withdrawn
-
1984
- 1984-03-30 IS IS2900A patent/IS1364B6/en unknown
- 1984-04-02 IE IE817/84A patent/IE57164B1/en not_active IP Right Cessation
- 1984-04-04 EP EP84400661A patent/EP0147244A1/en not_active Withdrawn
- 1984-04-04 MA MA20309A patent/MA20088A1/en unknown
- 1984-04-05 DE DE19843412868 patent/DE3412868A1/en not_active Withdrawn
- 1984-04-05 BE BE1/10992A patent/BE899331A/en not_active IP Right Cessation
- 1984-04-05 CZ CS842629A patent/CZ262984A3/en unknown
- 1984-04-05 NZ NZ207753A patent/NZ207753A/en unknown
- 1984-04-05 ZA ZA842573A patent/ZA842573B/en unknown
- 1984-04-06 YU YU640/84A patent/YU44762B/en unknown
- 1984-04-06 AR AR296218A patent/AR231398A1/en active
- 1984-04-06 IT IT48001/84A patent/IT1177655B/en active
- 1984-04-06 FI FI841376A patent/FI82603C/en not_active IP Right Cessation
- 1984-04-06 PH PH30510A patent/PH21938A/en unknown
- 1984-04-06 IN IN242/MAS/84A patent/IN160415B/en unknown
- 1984-04-06 JP JP59069883A patent/JPS60139616A/en active Granted
- 1984-04-06 BG BG64985A patent/BG49707A3/en unknown
- 1984-04-06 SU SU843728542A patent/SU1478993A3/en active
- 1984-04-06 PT PT78382A patent/PT78382B/en not_active IP Right Cessation
- 1984-04-06 NO NO841367A patent/NO169575C/en unknown
- 1984-04-06 DD DD84261741A patent/DD220782A5/en not_active IP Right Cessation
- 1984-04-06 GR GR74337A patent/GR79584B/el unknown
- 1984-04-06 GB GB08408978A patent/GB2151920B/en not_active Expired
- 1984-04-06 PL PL1984247098A patent/PL144356B1/en unknown
- 1984-04-06 LU LU85290A patent/LU85290A1/en unknown
- 1984-04-06 CH CH1755/84A patent/CH659386A5/en not_active IP Right Cessation
- 1984-04-06 OA OA58273A patent/OA07700A/en unknown
- 1984-04-06 HU HU841362A patent/HU190924B/en not_active IP Right Cessation
- 1984-04-06 DK DK180784A patent/DK165729C/en not_active IP Right Cessation
- 1984-04-07 KR KR1019840001840A patent/KR910004570B1/en not_active IP Right Cessation
- 1984-04-07 RO RO84114201A patent/RO89437A/en unknown
- 1984-04-08 IL IL71470A patent/IL71470A/en unknown
- 1984-04-10 ZW ZW60/84A patent/ZW6084A1/en unknown
- 1984-04-16 MX MX84101994U patent/MX7715E/en unknown
- 1984-04-24 ZM ZM20/84A patent/ZM2084A1/en unknown
- 1984-05-03 ES ES532125A patent/ES532125A0/en active Granted
- 1984-05-31 AU AU28904/84A patent/AU569516B2/en not_active Ceased
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0164959A2 (en) * | 1984-06-04 | 1985-12-18 | Sterwin Ag. | Pharmaceutical composition in sustained release unit dose form and process for its preparation |
EP0164959A3 (en) * | 1984-06-04 | 1986-12-17 | Sterwin Ag. | Pharmaceutical composition in sustained release unit dose form and process for its preparation |
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