GB2043442A - Film-coated pharmaceutical gelatine capsules - Google Patents
Film-coated pharmaceutical gelatine capsules Download PDFInfo
- Publication number
- GB2043442A GB2043442A GB8002576A GB8002576A GB2043442A GB 2043442 A GB2043442 A GB 2043442A GB 8002576 A GB8002576 A GB 8002576A GB 8002576 A GB8002576 A GB 8002576A GB 2043442 A GB2043442 A GB 2043442A
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- GB
- United Kingdom
- Prior art keywords
- film
- capsules
- soft gelatin
- spraying
- soluble
- Prior art date
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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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4891—Coated capsules; Multilayered drug free capsule shells
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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)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
Abstract
The thermal and dimensional stability of soft gelatin capsules containing a pharmaceutically active agent incorporated in the gelatin is improved by coating the capsules with a film coating of a film-forming polymer which is soluble or swellable in water and soluble in organic solvents, e.g. cellulose esters, cellulose ethers, polyvinyl pyrrolidone, acrylate/methacrylate co-polymers, polyethylene glycols, and zein. The capsules have a small air bubble as the core, and are usually for chewing or sucking to provide a prolonged local oral release of the active agent. The film coating may be applied by spraying on a solution of the polymer in organic solvent, and then drying the coating.
Description
SPECIFICATION
A process for thermally stabilising and improving the dimensional stability of soft gelatin capsules containing the pharmaceutical active principle in the shell
This invention relates to a process for thermally stabilising and improving the dimensional stability of soft gelatin capsules containing the pharmaceutical active principle in the shell.
Gelatin capsules have long proved to be a safe form of administration for medicaments of various kinds. Their advantages lie in their uniform quality and in their uniform properties in regard to shape, size and stability.
A distinction is normally drawn between hard gelatin capsules and soft gelatin capsules. The differences lie on the one hand in the type of gelatin used and on the other hand in the filling with the active principle. Thus, in the production of hard gelatin capsules, an empty capsule is initially prepared and subsequently filled with the active principle by special capsule filling machines during production of the medicament. The capsule is then closed again. In general, hard gelatin capsules are made solely of pure gelatin which may contain small quantitites of dyes and/or opacifiers. The gelatin used for hard gelatin does not normally contain a plasticiser.
By contrast, in the production of soft capsules, the actual medicament is prepared in a single operation, in other words the capsule shell is formed and filled in a single operation. The gelatin used for producing soft gelatin capsules contains relatively large quantities of plasticisers, for example glycerin and/or sorbitol. On account of the relatively high moisture content of the soft gelatin capsule shell, preservatives also have to be added. If necessary, dyes and opacifiers may be added. With soft gelatin capsules, it is possible in particular to administer decompositionsensitive or liquid active principles, such as vitamins, oily active principles, etc., in individually dosed stable form.
The production and use of hard and soft gelatin capsules is described for example in "The
Theory and Practice of Industrial Pharmacy" Lea and Febiger, Philadelphia, 1976, pages 389 to 420. Soft gelatin capsules are also described for example in German Offenlegungsschrift No.
2,520,338. The gelatin capsule is formed for example from a gelatin mass which has been plasticised with 8 to 15% by weight of glycerine and 12.5 to 15% by weight of sorbitol.
Soft gelatin capsules have recently been marketed which, in contrast to normal hard gelatin capsules and soft gelatin capsules, contain the active principle in the gelatin shell itself rather than in the interior of the capsule. In this special type of soft gelatin capsules, therefore, the active ingredients are incorporated in the gelatin gel and the capsules have a small air core which imparts a certain flexibility to the moulding. The gelatin mass used for this purpose has substantially the same composition as the gelatin mass used for the production of normal soft gelatin capsules. The composition of the gelatin mass is generally selected in such a way that, when chewed or sucked, the capsule uniformly releases the active principle over a periodsof about 1 5 minutes.Accordingly, this formulation is particularly suitable for medicaments which are intended to be perlingually or buccally resorbed (for example cardiac glycosides, steroids, etc.). In addition, they may be used for oral hygiene, as cosmetics and as throat disinfectants.
By virtue of its high mechanical strength, the moulding does not undergo any undesirable premature disintegration. In contrast to normal soft gelatin capsules and hard gelatin capsules which have not been subjected to an after-treatment to retard disintegration, the dissolution times are significantly longer. . However, the advantages of these soft gelatin capsules are offset by the following disadvantages:
1. On account of the high plasticiser content required, the capsules are highly hygroscopic.
The result of this is that, in bulk, the capsules stick together after a short time to form a semisolid to solid block. Similarly, in so-called push-through packs, the capsules take up moisture and soften.
2. The very low thermal stability of the soft gelatin capsules also leads to considerable problems with regard to transport and filling. Even at temperatures as low as 40"C, the soft gelatin capsule begins to change shape irreversibly, becoming increasingly more tacky in the procless. At a temperature of 50"C, the soft gelatin capsule melts completely. It should not be exposed even briefly to temperatures of this order.
Because of the above-mentioned disadvantages, therefore, soft gelatin capsules of the type in question are not yet totally satisfactory.
It is an object of the present invention to overcome or reduce the above-mentioned disadvantages of conventional soft gelatin capsules containing the active principle in the shell and, in particular, to provide soft gelatin capsules which have a good mechanical and thermal stability.
According to the present invention there is provided a process for thermally stabilising and improving the dimensional stability of soft gelatin capsules containing the pharmaceutical active principle in the shell, in which the capsules are provided with a film coating of a film-forming polymer which is soluble or swellable in water and soluble in organic solvents.
Suitable film-forming polymers which are soluble or swellable in water and soluble in solvents are, for example, pharmaceutically acceptable cellulose esters, cellulose ethers and/or polyvinyl pyrrolidone. Other suitable film-forming polymers or copolymers which satisfy the abovementioned requirements are, for example esters of acrylates and methacrylates, polyethylene glycols and proteins, such as zein (the main protein from the gluten of maize).
Specific examples of some suitable substances are given in the following Table:
Composition of materials for the film-coating process:
Trademark of the
Chemical description commercial product
Hydroxypropyl cellulose, molecular Klucel weight 50,000 to 1,250,000
Hydroxypropyl methyl cellulose, mixed Pharmacoat, methofas P, cellulose ether containing 1 9 to 30% methocel E of methoxyl and 3 to 12% of hydroxy Premium, Viscontran propyl groups
Methyl cellulose, methyl content 25 Methocel, tylose, to 30%, average degree of viscontran polymerisation 200 to 1000
Polyvinyl pyrrolidone, molecular Kollidon, plasdone weight 10,000 to 360,000
Vinyl pyrrolidone/vinyl acetate Kollidon VA 64 copolymer 60::40 molecular weight 40,000 to 90,000
Copolymers of dimethyl aminometh- Eudragit E acrylic acid and neutral methacrylic acid ester, soluble in the acid range
Ethyl acrylate/methyl methacryiate Eudragit E 30D copolymer 70:30
Polyethylene glycol, molecular Polyglycol, polywax weight 6000 to 20,000
Zein, protein molecular weight 35,000 to approximately 40,000
More information on these materials and on the production of corresponding film coatings may be found for example in "The Theory and Practice of Industrial Pharmacy" Lea and
Febiger, Philadelphia, 1976, pages 368 et seq.
It is highly surprising that film formers which are highly soluble in water and which are unsuitable for example for protection against moisture are capable as a film coating of significantly improving mechanical strength without unfavourably lengthening the disolution time of the capsules (cf. Comparison Example 1). The dimensional stability of the soft gelatin capsules is significantly improved by the coatings applied in accordance with the invention (cf.
Comparison Example 2).
The film coating is applied in the usual way, as described for example in the above-mentioned literature reference. The film coating is preferably applied by spraying on a lacquer solution either in a fluidised bed or in a sugarcoating drum.
The film former is preferably applied in an average quantity of from 0.9 to 3.3 mg/cm2, in particular from 1.1 to 2.2 mg/cm2. The film thickness obtained in this way amounts to between 8 and 30 itm and preferably to between 10 and 20 jim.
In a particular embodiment of the invention the coating is produced for example by initially preparing a lacquer solution having the following composition: film former 2 to 4 % polish 0.2 to 0.5% plasticiser 0.4 to 0.8% solvent 94.8 to 97.4%
Suitable polishes are, for example, polyethylene, for example having a molecular weight of 20,000, beeswax, Carnauba wax and solid paraffin. Examples of suitable plasticisers are 1,2propane diol, diethyl phthalate, dibutyl phthalate, glycerine and sorbitol. Suitable solvents are organic solvents for example mixtures of ethanol and methylene chloride (for example in a ratio by volume of 2: 3), methanol, trichloroethylene, carbon tetrachloride and isopropanol.
Other substances such as, for example, dyes or flavour correctants, such as sweeteners and flavours, may be added as required to the film-coating mixture so that the corresponding additives are incorporated in the film coating.
The lacquer solution thus obtained is then applied to the soft gelatin capsules at elevated temperature, for example 30"C, either in a fluidised bed or in a sugarcoating drum, followed by drying at an air temperature of for example 50"C.
The film coating thus produced shows good adhesion to the capsule, is transparent where clear film solutions are used, so that it does not affect the appearance of the capsule, and shows high strength.
The advantageous properties of soft gelatin capsules are retained and the disadvantages referred to earlier on are substantially eliminated.
The coated capsules: 1. Are less sensitive to moisture.
2. Do not stick together in storage containers, even after prolonged storage.
3. Are temperature-resistant. Even at 70"C, the capsules retain their shape and do not stick together. Accordingly, full stability testing is possible.
4. May be packaged without difficulty. Both the above-mentioned packs, i.e. cans (for bulk) and push-through packs are possible.
5. Solubility, elasticity and dissolution of the capsule in the mouth remain unaffected.
The invention is illustrated by the following Examples.
Example 1
A film coating for soft gelatin capsules is prepared from the following constituents: hydroxypropyl methyl cellulose (viscosity in 2% aqueous solution approximately 20 to 28 cps) 3g polyethylene glycol, molecular weight 20,000 0.3 g 1,2-propane diol 0.6 g solvent mixture consisting of 2 parts of ethanol and 3 parts of methylene chloride 96.1 g
Preparation of the lacquer solution:
The hydroxy propyl methyl cellulose and polyethylene glycol are successively dissolved in the solvent mixture. The 1,2-propane diol is then added to the solution with stirring.
Spraying:
2.5 Kg of plasticised gelatin cores made of a gelatin mass plasticized with 8 to 1 5% by weight of glycerine and 12.5 to 15% by weight of sorbitol are continuously sprayed with a total of 1.35 kg of lacquer solution under a spraying pressure of 2 atmospheres gauge, at a spraying speed of 80 to 100 g/minute and a spraying temperature of 30"C in a smooth fluidised-bed coater of the WSLD 5 type with nozzles of 0.8 mm in diameter. On completion of spraying, the coatings are dried for 4 minutes at 50"C.
Example 2
A film coating for soft gelatin capsules is prepared from the following constituents: hydroxypropyl cellulose, molecular weight approximately 100,000 3 g polyethylene glycol, molecular weight 20,000 0.2 g 1 ,2-propane diol 0.4 g solvent mixture consisting of parts of ethanol and 3 parts of methylene chloride 96.4 g
Preparation of the lacquer solution:
The hydroxypropyl cellulose and polyethylene glycol are successively dissolved in the solvent mixture. 1,2-propane diol is added to the slution with stirring.
Spraying:
2.5 Kg of gelatin cores as used in Example 1 are continuously sprayed with a total of 1.35 kg of lacquer solution under a spraying pressure of 2 atmospheres gauge, at a spraying speed of 80 to 100 g/minute and a spraying temperature of 30"C in a smooth fluidised bed coater of the WSLD 5 type with 0.8 mm diameter nozzles. On completion of spraying, the coatings are dried for 4 minutes at 50"C.
Example 3
A film for soft gelatin capsules is prepared from the following constituents: highly etherified methyl cellulose (viscosity in 2% aqueous solution approximately 220 cps) 3.0 g polyethylene glycol, molecular weight 20,000 0.2 g
1,2-propane diol 0.4 g solvent mixture consisting of 2 parts of ethanol and 3 parts of methylene chloride 96.4 g
Preparation of the lacquer solution:
The highly etherified methyl cellulose and polyethylene glycol are successively dissolved in the solvent mixture. 1,2-propane diol is added to the solution with stirring.
Spraying:
2.5 Kg of gelatin cores as used in Example 1 are continuously sprayed with a total of 1.35 kg of lacquer solution under a spraying pressure of 2 atmospheres gauge, at a spraying speed of 80 to 100 g/minute and a spraying temperature of 30"C in a smooth fluidised bed coater of the WSLD 5 type with 0.8 mm diameter nozzles. On completion of spraying, the coatings are dried for 4 minutes at 50"C.
Example 4
Film coating for soft gelatin capsules consisting of: methyl hydroxyethyl cellulose, molecular weight approximately 100,000 3.0 g polyethylene glycol, molecular weight 20,000 0.2 g 1,2-propane diol 0.4 g solvent mixture consisting of 2 parts of ethanol and 3 parts of methylene chloride 96.4 g
Preparation of the lacquer solution:
The methyl hydroxyethyl cellulose and polyethylene glycol are successively dissolved in the solvent mixture. 1 ,2-propane diol is added to the solution with stirring.
Spraying:
2.5 Kg of gelatin cores as used in Example 1 are continuously sprayed with a total of 1.35 kg of lacquer solution under a spraying pressure of 2 atmospheres gauge, at a spraying speed of 80 to 100 g/minute and at a spraying temperature of 30"C in a smooth fluidised bed coater of the WSLD 5 type with 0.8 mm diameter nozzles. On completion of spraying, the coatings are dried for 4 minutes at 50"C.
Example 5
A coloured film coating for soft gelatin capsules is prepared from the following constituents: polyvinyl pyrrolidone, molecular weight approximately 40,000 5.0 g polyethylene glycol, molecularweight 20,000 0.5 g
Cochenillerot A 0.05 g methylene chloride 40.0 g ethanol, denatured 54.5 g
Preparation of the lacquer solution:
The polyvinyl pyrrolidone, polyethylene glycol and Cochenillerot are successively dissolved in the solvent mixture. 1,2-propane diol is added to the solution with stirring.
Spraying:
2.5 Kg of gelatin cores as used in Example 1 are continuously sprayed with a total of 1.35 kg of lacquer solution under a spraying pressure of 2 atmospheres gauge, at a spraying speed of 80 to 100 g/minute and at a spraying temperature of 30"C in a smooth fluidised-bed coater of the WSLD 5 type with 0.8 mm diameter nozzles. On completion of spraying, the coatings are dried for 4 minutes at 50"C.
Example 6
A film coating for soft gelatin capsules containing a sweetener is prepared from the following constituents: polyvinyl pyrrolidone, molecularweight approximately 40,000 4.5 g
Zein 0.5 9 polyethylene glycol, molecularweight 20,000 0.5 g saccharin sodium 0.005 g methylene chloride 40.0 g ethanol, denatured 54.5 g
Preparation of the lacquer solution:
The polyvinyl pyrrolidone, zein, saccharin and polyethylene glycol are successively dissolved in the solvent mixture. 1,2-propane diol is added to the solution with stirring.
Spraying:
2.5 Kg of gelatin cores as used in Example 1 are continuously sprayed with a total of 1.35 kg of lacquer solution under a spraying pressure of 2 atmospheres gauge, at a spraying speed of 80 to 100 g/minute and at a spraying temperature of 30"C in a smooth fluidised-bed coater of the WSLD 5 type with 0.8 mm diameter nozzles. On completion of spraying, the coatings are dried for 4 minutes at 50"C.
Example 7
A film coating for soft gelatin capsules containing favour correctants is prepared from the following constituents: polyvinyl pyrrolidone, molecular 3.0 g weight approximately 40,000 ethyl cellulose 2.0 g silicone oil AK 350 0.5 g menthol DAB 7 0.005 g methylene chloride 40.0 g ethanol, denatured 54.5 g
Preparation of the lacquer solution:
The ethyl cellulose, polyvinyl pyrrolidone, menthol and polyethylene glycol are successively dissolved in the solvent mixture. The silicone oil is added to the solution with stirring.
Spraying:
2.5 Kg of gelatin cores as used in Example are continuously sprayed with a total of 1.35 kg of lacquer solution under a spraying pressure of 2 atmospheres gauge, at a spraying speed of from 80 to 100 g/minute and at a spraying temperature of 30"C in a smooth fluidised-bed coater of the WSLD 5 type with 0.8 mm diameter nozzles. On completion of spraying, the coatings are dried for 4 minutes at 50"C.
Comparison Example 1
To compare the solution times, capsules without a film coating, and soft gelatin capsules provided with a film coating in accordance with Example 1, are tested in water at 37"C in an
Erweka distintegration tester (cf. "Deutsches Arzneibuch", 7th Edition, 1968, Kommentar,
Wissenschaftliche Verlagsgesellschaft mbH Stuttgart, Govi Verlag GmbH, Frankfurt, Pages 75/96). The results are set out in Table I.
TABLE I
Dissolution time in minutes of capsules
Test No. with a film coating without a film coating 1 25 22 2 24 22 3 26 23
Comparison Example 2
To determine the dimensional stability of treated and untreated soft gelatin capsules, untreated soft gelatin capsules containing active principle and soft gelatin capsules containing active principle which had been film-coated in accordance with the invention were stored for 24 hours at 60"C. The tests were carried out with soft gelatin capsules which contained on the one hand an active principle extract (Solubifix) for treating respiratory catarrh, bronchitis, coughs, smoker's cough, influenza infections etc. and, on the other hand, chlorohexidine digluconate.
The results obtained are set out in Table II.
TABLE II
No. of Shape Slightly Seriously
Preparation capsules tested unchanged deformed deformed
Chewing capsules containing an anti-tussive active principle extract (a) uncoated 100 - ~ 100 (b) film-coated 100 100 capsules containing chlorohexidine digluconate (a) uncoated 100 - - 100 (b) film-coated 100 98 2
Example 8
A film coating for soft gelatin capsules was prepared from the following constituents: methocel E 5 premium 2.3 g methocel E 1 5 premium 2.3 g glycerine 0.9 g polyethylene glycol, molecular 0.45 g weight 20,000 ethanol, denatured 56.5 g water, demineralised 37.5 g
Preparation of the lacquer solution:
The ethanol and water were introduced initially, the polyethylene glycol dissolved in the solvent mixture so formed and the methocel E 5 and methocel E 1 5 introduced with stirring in lump-free form and dissolved. The glycerine was then added, followed by stirring for 5 minutes.
Spraying:
11.9 Kg of gelatin cores used according to Example 1 are continuously sprayed with a total of 2.816 kg of lacquer solution having the above composition under a spraying pressure of 4 atmospheres gauge, at a spraying speed of 100 g of lacquer solution per minute and at a spraying temperature of 35 to 40"C in a smooth fluidized bed coater of the WSLD 10 type with 1.2 mm diameter nozzles. On completion of spraying the coatings are dried for 4 minutes at 38 to 43"C.
Claims (9)
1. A process for thermally stabilising and improving the dimensional stability of soft gelatin capsules containing the pharmaceutical active principle in the shell, in which the capsules are provided with a film coating of a film-forming polymer which is soluble or swellable in water and soluble in organic solvents.
2. A process as claimed in claim 1 in which a cellulose ester or ether is used as the filmforming polymer.
3. A process as claimed in claim 2 in which hydroxy propyl methyl cellulose, hydroxy propyl cellulose, highly etherified methyl cellulose and/or methyl hydroxy ethyl cellulose is used as the film-forming polymer.
4. A process as claimed in claim 1 in which polyvinyl pyrrolidone is used as the film-forming polymer.
5. A process as claimed in claim 1, in which copolymers of modified acrylic acid/methacrylic acid esters are used as the film-forming polymer.
6. A process as claimed in any of claims 1 to 5, in which the film coating is applied by the use of a fluidised bed or sugarcoating drum.
7. A process as claimed in claim 1 substantially as herein described with reference to the
Examples.
8. A soft gelatin capsule containing the pharmaceutical active principle in the shell and provided with a film coating of a film forming polymer which is soluble or swellable in water and soluble in solvents.
9. A capsule as claimed in claim 8 substantially as herein described with reference to the
Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2903778A DE2903778C2 (en) | 1979-02-01 | 1979-02-01 | Use of hydroxypropylmethylcellulose for coating soft gelatine buccal capsules containing the pharmaceutical active substance in the shell |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2043442A true GB2043442A (en) | 1980-10-08 |
Family
ID=6061893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8002576A Withdrawn GB2043442A (en) | 1979-02-01 | 1980-01-25 | Film-coated pharmaceutical gelatine capsules |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS55104212A (en) |
| AR (1) | AR223202A1 (en) |
| AT (1) | AT372607B (en) |
| AU (1) | AU5488780A (en) |
| BE (1) | BE881462A (en) |
| CA (1) | CA1142084A (en) |
| CS (1) | CS222299B2 (en) |
| DD (1) | DD148584A5 (en) |
| DE (1) | DE2903778C2 (en) |
| DK (1) | DK42880A (en) |
| FR (1) | FR2447720A1 (en) |
| GB (1) | GB2043442A (en) |
| GR (1) | GR70084B (en) |
| HU (1) | HU183053B (en) |
| IL (1) | IL59137A (en) |
| IT (1) | IT8067057A0 (en) |
| NL (1) | NL8000634A (en) |
| PT (1) | PT70706A (en) |
| SE (1) | SE8000467L (en) |
| ZA (1) | ZA80382B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068110A (en) * | 1987-09-29 | 1991-11-26 | Warner-Lambert Company | Stabilization of enteric coated dosage form |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5953410A (en) * | 1982-09-20 | 1984-03-28 | Fujisawa Pharmaceut Co Ltd | Novel soft capsule agent |
| CH666405A5 (en) * | 1985-06-24 | 1988-07-29 | Ciba Geigy Ag | SOLID, DURABLE PHARMACEUTICAL FORMS WITH ELASTIC FILM COVER. |
| JPH02205A (en) * | 1987-11-09 | 1990-01-05 | Taisho Pharmaceut Co Ltd | Perfume-containing coating agent for soft capsule |
| FR2698560B1 (en) * | 1992-11-30 | 1995-02-03 | Virbac Laboratoires | Stabilized powdery active ingredients, compositions containing them, process for obtaining them and their applications. |
| US6030641A (en) * | 1997-06-03 | 2000-02-29 | Uni Colloid Kabushiki Kaisha | Sustained release capsule and method for preparing the same |
| US20070053972A1 (en) * | 2005-09-08 | 2007-03-08 | Cadbury Adams Usa Llc. | Gelatin capsules containing actives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE695234C (en) * | 1937-10-30 | 1940-08-20 | Schering Ag | Process for the protection of solid, crystalline fragments |
| CH476499A (en) * | 1964-12-31 | 1969-08-15 | Ciba Geigy | Mixture for coating rectal capsules |
| DE1617671C3 (en) * | 1967-03-07 | 1980-07-03 | A. Nattermann & Cie Gmbh, 5000 Koeln | Soft gelatine capsules with increased thermal stability |
| DE1767425B2 (en) * | 1968-05-09 | 1973-05-17 | R P Scherer GmbH, 6930 Eberbach | PROCESS FOR THE MANUFACTURING OF GELATIN CAPSULES RESISTANT TO MAGIC JUICE |
| BE757715A (en) * | 1969-10-21 | 1971-04-20 | Ciba Geigy | COATING FOR GELATIN CAPSULES AND PROCESS FOR THEIR PREPARATION |
-
1979
- 1979-02-01 DE DE2903778A patent/DE2903778C2/en not_active Expired
-
1980
- 1980-01-15 AT AT0019280A patent/AT372607B/en not_active IP Right Cessation
- 1980-01-16 IL IL59137A patent/IL59137A/en unknown
- 1980-01-16 IT IT8067057A patent/IT8067057A0/en unknown
- 1980-01-17 PT PT70706A patent/PT70706A/en unknown
- 1980-01-21 GR GR60993A patent/GR70084B/el unknown
- 1980-01-21 SE SE8000467A patent/SE8000467L/en not_active Application Discontinuation
- 1980-01-23 AU AU54887/80A patent/AU5488780A/en not_active Abandoned
- 1980-01-23 ZA ZA00800382A patent/ZA80382B/en unknown
- 1980-01-23 DD DD80218609A patent/DD148584A5/en unknown
- 1980-01-24 AR AR279725A patent/AR223202A1/en active
- 1980-01-25 JP JP769480A patent/JPS55104212A/en active Pending
- 1980-01-25 GB GB8002576A patent/GB2043442A/en not_active Withdrawn
- 1980-01-28 CS CS80585A patent/CS222299B2/en unknown
- 1980-01-28 FR FR8001763A patent/FR2447720A1/en not_active Withdrawn
- 1980-01-28 HU HU80177A patent/HU183053B/en unknown
- 1980-01-31 NL NL8000634A patent/NL8000634A/en not_active Application Discontinuation
- 1980-01-31 BE BE0/199196A patent/BE881462A/en not_active IP Right Cessation
- 1980-01-31 CA CA000344841A patent/CA1142084A/en not_active Expired
- 1980-01-31 DK DK42880A patent/DK42880A/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068110A (en) * | 1987-09-29 | 1991-11-26 | Warner-Lambert Company | Stabilization of enteric coated dosage form |
Also Published As
| Publication number | Publication date |
|---|---|
| HU183053B (en) | 1984-04-28 |
| DE2903778A1 (en) | 1980-08-07 |
| BE881462A (en) | 1980-05-16 |
| FR2447720A1 (en) | 1980-08-29 |
| DE2903778C2 (en) | 1982-06-03 |
| CS222299B2 (en) | 1983-06-24 |
| DD148584A5 (en) | 1981-06-03 |
| IL59137A (en) | 1983-10-31 |
| NL8000634A (en) | 1980-08-05 |
| ZA80382B (en) | 1981-01-28 |
| DK42880A (en) | 1980-08-02 |
| CA1142084A (en) | 1983-03-01 |
| PT70706A (en) | 1980-02-01 |
| AT372607B (en) | 1983-10-25 |
| IT8067057A0 (en) | 1980-01-16 |
| SE8000467L (en) | 1980-08-02 |
| AR223202A1 (en) | 1981-07-31 |
| GR70084B (en) | 1982-07-30 |
| ATA19280A (en) | 1983-03-15 |
| AU5488780A (en) | 1980-08-07 |
| JPS55104212A (en) | 1980-08-09 |
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