US2991226A - Long-acting wax-like talc pillage of penicillin - Google Patents
Long-acting wax-like talc pillage of penicillin Download PDFInfo
- Publication number
- US2991226A US2991226A US712833A US71283358A US2991226A US 2991226 A US2991226 A US 2991226A US 712833 A US712833 A US 712833A US 71283358 A US71283358 A US 71283358A US 2991226 A US2991226 A US 2991226A
- Authority
- US
- United States
- Prior art keywords
- penicillin
- core
- layer
- soluble
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
-
- 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
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
Definitions
- the present invention relates to a solid oral penicillin tablet adapted to provide a prolonged therapeutic blood level for a period of time of up to about twelve hours.
- This tablet provides an initial high therapeutic blood level of penicillin which decreases rapidly within six to seven hours, and therefore does not provide any worth-while sustained therapeutic blood level of penicillin.
- the central core is adapted for slow.
- disintegration in the intestinal tract thereby providing a sustained blood level of penicillin and comprises a Watersoluble penicillin salt, a hydrophobic agent, a hydrophilic agent, a hydrophilic fibrous material, and a waterlin salt.
- a barrier layer to separate the penicillin salt of the core and subsequent incompatible materials
- an enteric coating to separate the penicillin salt of the core and subsequent incompatible materials
- a further barrier layer to separate the penicillin salt of the core and subsequent incompatible materials
- a bonding layer to facilitate the adhesion of the penicil lin
- a penicillin layer containing a water-soluble penicil- If a more pharmaceutically elegant tablet is desired, the iollowinglayers are added: a further barrier layer; a smoothing layer; and finally a finishing layer which provides an-attractive appearance.
- the central compressed core is obtained by the compression on a tablet-making machine of an intimate mixture of a water-soluble penicillin salt, a hydrophobic agent, a hydrophilic agent, a hydrophilic fibrous material and a water-insoluble binder.
- the central core is thus specially designed to produce a prolonged release of penicillin in the intestinal tract by the counter-balancing actions of the hydrophobic and hydrophilic agents which I nesium stearates or palmitates and solid hydrogenated swelling properties.
- penicillin salts used are preferably water-soluble; salts, for example, potassium, sodium, calcium and ammonium salts of penicillin G or V (phenoxymethyl penicillin acid).
- the amount of penicillin salt which can be incorporated into the core has been found to be about 400,000 international units, but a higher amount could be used with the limiting factor being the practical size'j of the finished tablet.
- penicillin may be between 50,000 and 200,000 interna tional units. Ifdesired, part of the penicillin may be: replaced by a sulfa drug, for example, sul-fadiazine, sulfamerazine and others and mixtures thereof.
- hydrophobic agent there may be men-,
- alkaline earth metal stearates' or palmitates for example, aluminum, calcium and magvegetable fats, for example, hydrogenated castor oil and.
- a hydrophobic. agent is used in an amount of 0.5 to 5.0 percent by.
- hydrophilic agent there is selected one which has As an example of suitable hydro-f philic agents having swelling properties, there may be mentioned carboxymethyl cellulose and salts thereof,
- the hydrophilic agent is used in an amount of 0.5 to 5.0 percent by weight.
- hydrophilic fibrous material that may be used, there may be mentioned purified cellulose having an average particle size of from 30 to 50 microns, which is available commercially under the, trademark Solkaffioc. manufactured by the Brown Company, Berlin, New Hampshire, U.S.A. Also suitable would be ground citrus pulp having a particle size smaller than 1,000 microns. amount of from 2 to 10 percent by weight.
- This fibrous material is used in an.
- a non-aqueous solution of a water-insoluble binder for example, ethyl cellulose, polyvinyl acetate, polyvinyl chloride, cellulose acetate or zein and formed into granules by standard methods used in the art.
- the granules are dried to a moisture content of not higher than 0.5 percent by weight, blended with the hydrophobic agent and the balance of the hydrophilic agent and the hydrophilic fibrous material, and then compressed in a low humidity atmosphere to form the compressed core of the tablet of the present invention.
- This penicillin core is then transferred to a standard coating pan for further treatment using methods known in the art.
- a barrier layer which separates the penicillin salt in the core from any incompatible material which will be used in subsequent coatings.
- This barrier layer is essentially a water-soluble, solid, wax-like polymeric material which is compatible with penicillin and to which is preferably added an inert filler.
- a suitable water-soluble wax-like polymeric material there may be mentioned polyethylene glycols having a molecular weight of from 1500 to 6000, and the corresponding mixed polymers of ethylene and propylene glycols.
- the barrier layer is applied from a dispersion in a solvent in which the penicillin salts are insoluble, for example, carbon tetrachloride.
- enteric coating which will protect the core from attack in the stomach but permit disintegration in the intestinal tract.
- enteric coating material there may be used any of those well known in the art, for example, cellulose acetate phthalate, medicinal shellac, or polyvinyl acetate phthalate having an acetyl content of from 4 to 15% and a phthalyl content of from 40 to 70%.
- This second barrier layer which is added a grossing agent comprises a water-soluble, solid, wax-like polymeric material, similar to the one used in the first barrier layer and a film-forming material, for example, polyvinyl pyrrolidone and an inert grossing agent, for example, talc.
- This second barrier and grossing layer is applied from an alcoholic dispersion.
- the second barrier and grossing layer can be replaced by a barrier layer made up essentially of sugar grossing applied from an aqueous medium.
- a bonding layer consisting of a mixture of a solid wax-like polymeric material and a filmforming polymer, for example, polyvinyl pyrrolidone, which is applied in an alcoholic solvent.
- the bonding layer can consist of a mixture of sucrose and a film-forming material, for example, polyvinyl pyrrolidone applied from an aqueous alcoholic solution.
- the bonding layer has adhesive properties to provide a base for subsequent layers.
- a penicillin layer made up essentially of a penicillin salt which is applied from a nonaqueous suspension which may contain an alkaline buffer and an inert filler, for example, talc.
- a barrier layer as above
- a grossing layer as above
- a finishing layer which is essentially a film coating made up of a solid, wax-like polymeric material, for example, polyethylene glycols, a film-forming polymer, for example, polyvinyl acetate, polyvinyl acetate phthalate, having a phthalyl content of from 40 to 70 percent and an acetyl content of from 4 to 15 percent, a finely divided silica, talc and may include colouring and flavouring agents.
- FIGURE 1 is an enlarged side elevation of the improved tablet of the present invention
- FIGURE 2 is a view similar to FIGURE 1 but partially sectioned to show the various layers and coatings surrounding the compressed core of a preferred tablet of the present invention
- FIGURE 3 is a graph showing the penicillin blood levels obtained with a single tablet of the present invention.
- the tablet 10 comprises a central compressed penicillin core 12 which is adapted for sustained release of the penicillin in the intestinal tract.
- a water dispersible barrier coat 14 surrounds the core 12 to prevent the solvents used in applying the enteric coating 16 from leaching the penicillin present in the core 12.
- the barrier coat 14 also serves to separate the penicillin present in the core 12 from any subsequent coatings with which it may be incompatible.
- an enteric coating 16 which protects the penicillin core 12 from attack by gastric secretions.
- a further barrier and grossing coat 18 This second barrier coating is present to separate the enteric coating 16 from the penicillin layer 22 and also serves as a grossing coat to round out the tablet.
- a bonding coat 20 to provide adhesion for the penicillin layer 22, which is present to provide initial blood levels on ingestion of the tablet.
- a further barrier coat 24 Over the penicillin layer 22 is a further barrier coat 24 then a smoothing layer 26 and finally a finishing coat 28 which provides a smooth outer surface of pleasing apperance.
- the above powders are blended together and then mixed with 240 ml. of a 10 percent ethyl cellulose solution in denatured ethyl alcohol. This mixture is granulated by methods known in the art and to the dried granules a blend of the following powders is added.
- This mixture is compressed to form 1500 cores, each Weighing approximately 0.4 gm. and containing 400,000 international units of penicillin.
- COATING STEP #1 (BARRIER LAYER) The tablets are coated with 200 ml. of a mixture containing:
- Carbon tetrachloride q.s. to 200 ml.
- This mixture is applied in 20 applications of 10 ml. and serves to completely seal in the penicillin of the core tablet.
- talc as a dusting powder to prevent the tablets sticking together after each application.
- This layer provides acid resistant properties to protect the tablet from attack by gastric secretions, during passage through the stomach.
- COATING STEP #3 (BARRIER AND eRossrNo LAYER) The tablets are coated with 300' ml. of a mixture containing:
- Talc gm 110.0 Polyethylene glycol (M.W. 6000) "gm..- 67.5 Isopropyl myristate ml 4.2 Amorphous silica (3-5 microns) gm 6.6 Polyvinyl pyrrolidone gm 5.4
- the mixture is applied in 30 portions of ml. each. This layer provides a barrier between the enteric layer and subsequent layers and also rounds out the edges of the tablets.
- the tablets are then coated with a mixture containing:
- Potassium penicillin G gm-.. 112.5 Magnesium stearate gm 7.5 Talc gm 15.0 Calcium carbonate gm 12.0 Isopropyl myristate ml 7.5 Methylene chloride ml 135 Denatured alcohol ml 90 This mixture is applied in 12 ml. portions with thorough drying between each application. The total amount applied is suflicient to provide 100,000 units of penicillin per tablet.
- COATING STEP #7 (GROSSING LAYER) The tablets are coated with 300 ml. of the same mixture used in step #3. Thirty applications of 10 ml. are used.
- COATING STEP #8 (FINISHING LAYER) The tablets are coated with 200 ml. of a mixture containing:
- Polyethylene glycol (M.W. 6000) gm 48.3 Stearic acid gm 0.08 Isopropyl myristate ml 3.0 Polyvinyl acetate phthalate gm 3.9 Amorphous silica (3-5 microns) gm 4.8 Talc gm 20.0 Saccharin insoluble gm 0.06 D. and C. Yellow #11 gm 0.5
- Penicillin blood levels in units per ml. of serum following a single oral dose of 500,000 units 'of potassium penicillin G in the form of a specially coatedtablet are shown in Table II.
- the above powders are blended together in a suitable mixer and then treated with 11,000 ml. of a 10% solution of ethyl cellulose in denatured alcohol to form granules by standard methods used in the art.
- the granules are dried to reduce the moisture content to less than 0.5% and are then blended with the following mixture:
- Purified fibrous cellulose (30-50 microns) 640 Sodium carboxymethyl cellulose (high viscosity 32 0. Magnesium stearate 360 COATING STEP #1 BARRmn LAYER) The tablets are coated with 8000 ml. of a mixture containing:
- Polyethylene glycol (M.W. 6000) gm 2000 Isopropyl myn'state ml 280 Amorphous silica (3-5 microns) gn1 200 Talc gm 3150 Carbon tetrachloride, q.s. to 8000 ml.
- This mixture is applied in 12 portions in the customary manner to form a water-dispersible layer which seals in the penicillin of the core tablets.
- COATING STEP #2 (ENTERIC LAYER) COATING STEP #3 (BARRIER AND GROSSING LAYER)
- the tablets are coated with 900 ml. of a 15% aqueous solution of gelatin and then with 10,000 ml. of a mixture containing:
- This mixture is applied in 20 portions and serves to isolate the enteric layer from subsequent coatings and also rounds out the edges of the tablets.
- COATING STEP #4 (BONDING LAYER) The tablets are coated with 2500 ml. of a solution containing:
- COATING STEP #6 (BARRIER. LAYER) The tablets are coated with 8000 ml. of the same mixture used in step #1 to seal in the penicillin oi the previous layer.
- Polyethylene glycol M.W. 6000
- Polyvinyl pyrrolidone gm 1440
- Amophous silica 3-5 microns
- "gm..- 144 Talc gm” 2160 Isopropyl myristate ml 144 Denatured alcohol ml 2100 Carbon tetrachloride, q.s. to 6000 ml.
- This mixture is applied in 12 portions and provides further smoothing of the tablet surface.
- COATING STEP #8 (FINISHING LAYER) The tablets are coated with 7500 ml. of a mixture containing:
- This mixture is applied in 30 portions and then the tablets are heated to 50 C. while rolling in the coating pan. This provides a smooth hard finish of attractive appearance and pleasant taste.
- a prolonged action medicinal penicillin tablet comprising a core of compressed coated granules, said granules comprised of a major amount of a water-soluble penicillin salt, a hydrophilic fibrous material, a hydrophilic agent having swelling properties and a water-insoluble binder, said granules having been coated with a mixture of dry solids comprising a hydrophilic fibrous material, a hydrophilic agent having swelling properties and a solid hydrophobic agent selected from the group consisting of alkaline earth metal salts of stearic and palmitic acids and solid hydrogenated vegetable fats, and the coated granules having then been compressed, said core being surrounded by a first barrier layer of a mixture of a major amount of talc with readily water-soluble wax-like materials selected from the group consisting of polyethylene glycols having a molecular weight of "from 1500 to 6000 and the corresponding mixed polymers of ethylene and propylene glycols, and an enteric coating surrounding said first barrier layer, and an outer layer
- a tablet according to claim 1 having a barrier and grossing layer surrounding said enteric layer and a bonding layer surrounding said last-mentioned barrier and grossing layer, the outer penicillin layer surrounding said last-mentioned bonding layer.
- a tablet according to claim 5 wherein the readily water-soluble material in said bonding layer is water-sol- 10 uble wax-like polyethylene glycols having a molecular weight of from 1500 to 6000.
- a tablet according to claim 1 having a second barrier layer surrounding said outer penicillin layer.
- said second barrier layer comprises a mixture of talc and a readily water-soluble wax-like material selected from the group consisting of polyethylene glycols having a molecular weight of from 1500 to 6000, and the corresponding mixed polymers of ethylene and propylene glycols.
- a tablet according to claim 9 wherein the readily Water-soluble Wax-like material in said second barrier layer is polyethylene glycols having a molecular weight of from 1500 to 6000.
- a tablet according to claim 9 having a smoothing layer covering said second barrier layer and a finishing layer surrounding said smoothing layer, said finishing layer forming the exposed surface of the tablet.
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- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL109170D NL109170C (pt) | 1958-02-03 | ||
NL235736D NL235736A (pt) | 1958-02-03 | ||
US712833A US2991226A (en) | 1958-02-03 | 1958-02-03 | Long-acting wax-like talc pillage of penicillin |
DEF27628A DE1093050B (de) | 1958-02-03 | 1959-02-03 | Verfahren zur Herstellung einer Penicillintablette mit verlaengerter Wirkung |
BE587587A BE587587A (fr) | 1958-02-03 | 1960-02-12 | Tablettes de pénicilline à activite prolongée |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US712833A US2991226A (en) | 1958-02-03 | 1958-02-03 | Long-acting wax-like talc pillage of penicillin |
Publications (1)
Publication Number | Publication Date |
---|---|
US2991226A true US2991226A (en) | 1961-07-04 |
Family
ID=24863741
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US712833A Expired - Lifetime US2991226A (en) | 1958-02-03 | 1958-02-03 | Long-acting wax-like talc pillage of penicillin |
Country Status (4)
Country | Link |
---|---|
US (1) | US2991226A (pt) |
BE (1) | BE587587A (pt) |
DE (1) | DE1093050B (pt) |
NL (2) | NL109170C (pt) |
Cited By (45)
Publication number | Priority date | Publication date | Assignee | Title |
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US3048526A (en) * | 1958-08-04 | 1962-08-07 | Wander Company | Medicinal tablet |
US3074852A (en) * | 1960-06-06 | 1963-01-22 | American Home Prod | Pharmaceuticals with delayed release |
US3096248A (en) * | 1959-04-06 | 1963-07-02 | Rexall Drug & Chemical Company | Method of making an encapsulated tablet |
US3097144A (en) * | 1960-10-14 | 1963-07-09 | Upjohn Co | Heat-cured, polymeric, medicinal dosage film coatings containing a polyvinylpyrrolidone copolymer, polyethenoid acid, and polyethylene glycol |
US3102845A (en) * | 1960-11-18 | 1963-09-03 | Mcneilab Inc | Pharmaceutical tablet |
US3121044A (en) * | 1960-10-06 | 1964-02-11 | Beecham Res Lab | Three-layer compressed penicillin tablet |
US3131123A (en) * | 1959-03-13 | 1964-04-28 | Lab Francais De Therapeutique | Enteric tablets and manufacture thereof |
US3132075A (en) * | 1960-10-17 | 1964-05-05 | Upjohn Co | Solid medicinal dosage forms coated with hydroxyethylcellulose and hydrolyzed styrene-maleic anhydride copolymer |
US3133863A (en) * | 1961-03-10 | 1964-05-19 | Strong Cobb Arner Inc | Sustained release therapeutic tablet compositions comprising organic solvent-gelled gums |
US3136695A (en) * | 1961-03-10 | 1964-06-09 | Strong Cobb Arner Inc | Anhydrous thixotropic gel sustained release therapeutic compositions and method of preparation |
US3149041A (en) * | 1962-04-09 | 1964-09-15 | Dow Chemical Co | Thin film coating for tablets and the like and method of coating |
US3179600A (en) * | 1960-03-10 | 1965-04-20 | Ncr Co | Minute color-forming capsules and record material provided with such |
US3205135A (en) * | 1961-07-05 | 1965-09-07 | Lphivens Kemiske Fabrik Ved A | Combining penicillinase-sensitive penicillins with fusidic acid for use against penicillinase-producing bacteria |
US3247064A (en) * | 1962-03-30 | 1966-04-19 | Shionogi & Co | Multivitamin tablet stabilized with porous silica |
US3256153A (en) * | 1963-02-08 | 1966-06-14 | Smith Kline French Lab | Method of stabilizing wax-fat coating materials and product thereof |
US3331696A (en) * | 1962-01-20 | 1967-07-18 | Boehringer & Soehne Gmbh | Dragee coating composition |
US3362881A (en) * | 1963-07-15 | 1968-01-09 | Boehringer Sohn Ingelheim | Sustained release tablet and method of manufacturing same |
US3371015A (en) * | 1962-06-28 | 1968-02-27 | Haessle Ab | Pharmaceutical core compositions with thin rapidly disintegrating coatings |
US3383283A (en) * | 1964-01-24 | 1968-05-14 | Merck & Co Inc | Medicinal pellets coated with overlapping porous fatty acid leaflet layers |
US3393155A (en) * | 1964-02-28 | 1968-07-16 | Degussa | Predominantly aqueous compositions in a fluffy powdery form approximating powdered solids behavior and process for forming same |
US3395213A (en) * | 1963-01-16 | 1968-07-30 | Boehringer & Soehne Gmbh | Sugar- and polyethylene glycol-coated dragees, nonsticking together, or to dragee-making kettles |
US3420931A (en) * | 1964-04-23 | 1969-01-07 | Merck Ag E | Pharmaceutical dragee |
US3437728A (en) * | 1964-06-15 | 1969-04-08 | Diwag Chemische Fabriken Gmbh | Protracted release pharmaceutical compositions |
US3456049A (en) * | 1965-05-25 | 1969-07-15 | Ciba Geigy Corp | Gradual-release tablet |
US3485914A (en) * | 1966-07-05 | 1969-12-23 | Chem & Pharm Patent Hold Ltd | Process for the production of a pharmaceutical antibiotic preparation having delayed therapeutic action and the composition prepared according to such process |
US3499959A (en) * | 1966-07-05 | 1970-03-10 | Chem & Pharm Patent Hold Ltd | Therapeutic tetracycline preparation having delayed therapeutic action and processes for the production of said preparation |
US4248858A (en) * | 1979-08-09 | 1981-02-03 | American Home Products Corporation | Sustained release pharmaceutical compositions |
US4248856A (en) * | 1979-07-10 | 1981-02-03 | American Home Products Corporation | Sustained release pharmaceutical compositions |
US4248857A (en) * | 1979-08-09 | 1981-02-03 | American Home Products Corporation | Sustained release pharmaceutical compositions |
FR2462911A1 (fr) * | 1979-08-16 | 1981-02-20 | Sandoz Sa | Nouvelles compositions pharmaceutiques solides, sous forme de doses unitaires, a enrobage enterique a base d'un sel hydrosoluble de la cellulose partiellement estirifiee par un acide dicarboxylique |
US4309406A (en) * | 1979-07-10 | 1982-01-05 | American Home Products Corporation | Sustained release pharmaceutical compositions |
US4309404A (en) * | 1979-08-09 | 1982-01-05 | American Home Products Corporation | Sustained release pharmaceutical compositions |
US4309405A (en) * | 1979-08-09 | 1982-01-05 | American Home Products Corporation | Sustained release pharmaceutical compositions |
US4432966A (en) * | 1979-12-10 | 1984-02-21 | Roussel-Uclaf | Compressed tablets for disintegration in the colon comprising an active ingredient containing nucleus coated with a first layer containing microcrystalline cellulose which is coated with an enteric organic polymer coating |
WO1985003436A1 (en) * | 1984-02-10 | 1985-08-15 | A/S Alfred Benzon | Diffusion coated multiple-units dosage form |
US4609542A (en) * | 1978-12-22 | 1986-09-02 | Elan Corporation, P.L.C. | New pharmaceutical forms for administration of medicaments by oral route, with programmed release |
US4713248A (en) * | 1984-02-10 | 1987-12-15 | A/S Alfred Benzon | Diffusion coated multiple-units dosage form |
US4775536A (en) * | 1986-02-24 | 1988-10-04 | Bristol-Myers Company | Enteric coated tablet and process for making |
US4789548A (en) * | 1986-04-24 | 1988-12-06 | Tisdale John W | Medication and method for treating heartworms in dogs |
US4810500A (en) * | 1986-04-24 | 1989-03-07 | Tisdale John W | Medication and method for treating heartworms in dogs |
US4994279A (en) * | 1988-02-03 | 1991-02-19 | Eisai Co., Ltd. | Multi-layer granule |
WO2001037813A2 (de) * | 1999-11-24 | 2001-05-31 | Lts Lohmann Therapie-Systeme Ag | Mehrschichtige zubereitung zur gesteuerten, pulsartigen abgabe von wirkstoffen |
US20060153918A1 (en) * | 2004-07-26 | 2006-07-13 | Lerner E I | Dosage forms with an enterically coated core tablet |
US7556802B1 (en) * | 1999-06-25 | 2009-07-07 | Basf Se | Polymer-coated, granulated enzyme-containing feed additives and method for the production thereof |
WO2013130785A3 (en) * | 2012-03-01 | 2013-10-24 | Bristol-Myers Squibb Company | Extended release pharmaceutical formulations of water-soluble active pharmaceutical ingredients and methods for making the same |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3217071A1 (de) * | 1982-05-06 | 1983-11-10 | Rüdiger Dr. 6365 Rosbach Gröning | Arzneimittel fuer die perorale applikation mit verbesserter biologischer verfuegbarkeit der wirkstoffe |
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GB756900A (en) * | 1954-06-02 | 1956-09-12 | Lilly Co Eli | Improvements in or relating to composite enteric-coated tablets |
GB792545A (en) * | 1955-07-27 | 1958-03-26 | Novo Terapeutisk Labor As | Manufacture of antibiotic preparations having a protracted effect |
-
0
- NL NL235736D patent/NL235736A/xx unknown
- NL NL109170D patent/NL109170C/xx active
-
1958
- 1958-02-03 US US712833A patent/US2991226A/en not_active Expired - Lifetime
-
1959
- 1959-02-03 DE DEF27628A patent/DE1093050B/de active Pending
-
1960
- 1960-02-12 BE BE587587A patent/BE587587A/fr unknown
Patent Citations (6)
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US2076112A (en) * | 1930-01-30 | 1937-04-06 | Sweets Lab Inc | Masticable material |
GB669782A (en) * | 1948-10-30 | 1952-04-09 | Strong Cobb And Company Inc | Improved pellets for pharmaceutical use |
US2540253A (en) * | 1949-02-08 | 1951-02-06 | Merck & Co Inc | Granulation process |
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Cited By (49)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3048526A (en) * | 1958-08-04 | 1962-08-07 | Wander Company | Medicinal tablet |
US3131123A (en) * | 1959-03-13 | 1964-04-28 | Lab Francais De Therapeutique | Enteric tablets and manufacture thereof |
US3096248A (en) * | 1959-04-06 | 1963-07-02 | Rexall Drug & Chemical Company | Method of making an encapsulated tablet |
US3179600A (en) * | 1960-03-10 | 1965-04-20 | Ncr Co | Minute color-forming capsules and record material provided with such |
US3074852A (en) * | 1960-06-06 | 1963-01-22 | American Home Prod | Pharmaceuticals with delayed release |
US3121044A (en) * | 1960-10-06 | 1964-02-11 | Beecham Res Lab | Three-layer compressed penicillin tablet |
US3097144A (en) * | 1960-10-14 | 1963-07-09 | Upjohn Co | Heat-cured, polymeric, medicinal dosage film coatings containing a polyvinylpyrrolidone copolymer, polyethenoid acid, and polyethylene glycol |
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Also Published As
Publication number | Publication date |
---|---|
NL109170C (pt) | |
NL235736A (pt) | |
DE1093050B (de) | 1960-11-17 |
BE587587A (fr) | 1960-05-30 |
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