CA1142084A - Process for thermally stabilising and improving the dimensional stability of soft gelatin capsules containing the pharmaceutical active principal in the shell - Google Patents
Process for thermally stabilising and improving the dimensional stability of soft gelatin capsules containing the pharmaceutical active principal in the shellInfo
- Publication number
- CA1142084A CA1142084A CA000344841A CA344841A CA1142084A CA 1142084 A CA1142084 A CA 1142084A CA 000344841 A CA000344841 A CA 000344841A CA 344841 A CA344841 A CA 344841A CA 1142084 A CA1142084 A CA 1142084A
- Authority
- CA
- Canada
- Prior art keywords
- gelatin capsules
- soft gelatin
- capsules
- spraying
- film
- 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
Links
- 239000007903 gelatin capsule Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 10
- 230000003019 stabilising effect Effects 0.000 title abstract description 4
- 239000002775 capsule Substances 0.000 claims abstract description 24
- 239000007888 film coating Substances 0.000 claims abstract description 19
- 238000009501 film coating Methods 0.000 claims abstract description 19
- 238000000576 coating method Methods 0.000 claims description 10
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 4
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000009495 sugar coating Methods 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 10
- 229920000642 polymer Polymers 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 238000005507 spraying Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000004922 lacquer Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 108010010803 Gelatin Proteins 0.000 description 16
- 239000008273 gelatin Substances 0.000 description 16
- 229920000159 gelatin Polymers 0.000 description 16
- 235000019322 gelatine Nutrition 0.000 description 16
- 235000011852 gelatine desserts Nutrition 0.000 description 16
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229960004063 propylene glycol Drugs 0.000 description 9
- 235000013772 propylene glycol Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229920002494 Zein Polymers 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000005019 zein Substances 0.000 description 4
- 229940093612 zein Drugs 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003091 Methocel™ Polymers 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 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 description 2
- 229920003148 Eudragit® E polymer Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229960003260 chlorhexidine Drugs 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- KOWWOODYPWDWOJ-LVBPXUMQSA-N elatine Chemical compound C([C@]12CN(C3[C@@]45OCO[C@]44[C@H]6[C@@H](OC)[C@@H]([C@H](C4)OC)C[C@H]6[C@@]3([C@@H]1[C@@H]5OC)[C@@H](OC)CC2)CC)OC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O KOWWOODYPWDWOJ-LVBPXUMQSA-N 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000003605 opacifier Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- DSEKYWAQQVUQTP-UHFFFAOYSA-N Cerin Natural products CC12CCC3(C)C4CC(C)(C)CCC4(C)CCC3(C)C2CCC2(C)C1CC(O)C(=O)C2C DSEKYWAQQVUQTP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 229920003083 Kollidon® VA64 Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229920003072 Plasdone™ povidone Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4891—Coated capsules; Multilayered drug free capsule shells
Landscapes
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2903778.3 | 1979-02-01 | ||
| DE2903778A DE2903778C2 (de) | 1979-02-01 | 1979-02-01 | Verwendung von Hydroxypropylmethylcellulose zum Überziehen von den pharmazeutischen Wirkstoff in der Hülle enthaltenden Weichgelatine-Buccalkapseln |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1142084A true CA1142084A (en) | 1983-03-01 |
Family
ID=6061893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000344841A Expired CA1142084A (en) | 1979-02-01 | 1980-01-31 | Process for thermally stabilising and improving the dimensional stability of soft gelatin capsules containing the pharmaceutical active principal in the shell |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS55104212A (de) |
| AR (1) | AR223202A1 (de) |
| AT (1) | AT372607B (de) |
| AU (1) | AU5488780A (de) |
| BE (1) | BE881462A (de) |
| CA (1) | CA1142084A (de) |
| CS (1) | CS222299B2 (de) |
| DD (1) | DD148584A5 (de) |
| DE (1) | DE2903778C2 (de) |
| DK (1) | DK42880A (de) |
| FR (1) | FR2447720A1 (de) |
| GB (1) | GB2043442A (de) |
| GR (1) | GR70084B (de) |
| HU (1) | HU183053B (de) |
| IL (1) | IL59137A (de) |
| IT (1) | IT8067057A0 (de) |
| NL (1) | NL8000634A (de) |
| PT (1) | PT70706A (de) |
| SE (1) | SE8000467L (de) |
| ZA (1) | ZA80382B (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5595762A (en) * | 1992-11-30 | 1997-01-21 | Laboratoires Virbac | Stabilized pulverulent active agents, compositions containing them, process for obtaining them and their applications |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5953410A (ja) * | 1982-09-20 | 1984-03-28 | Fujisawa Pharmaceut Co Ltd | 新型ソフトカプセル剤 |
| CH666405A5 (de) * | 1985-06-24 | 1988-07-29 | Ciba Geigy Ag | Feste, haltbare darreichungsformen mit elastischem filmueberzug. |
| US5068110A (en) * | 1987-09-29 | 1991-11-26 | Warner-Lambert Company | Stabilization of enteric coated dosage form |
| JPH02205A (ja) * | 1987-11-09 | 1990-01-05 | Taisho Pharmaceut Co Ltd | 香料含有ソフトカプセル用コーティング剤 |
| 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 |
| CN117677379A (zh) * | 2021-07-06 | 2024-03-08 | R·P·谢勒技术有限公司 | 软胶囊 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE695234C (de) * | 1937-10-30 | 1940-08-20 | Schering Ag | Verfahren zum Schutz von in fester, kristalliner Fersplittern |
| CH476499A (de) * | 1964-12-31 | 1969-08-15 | Ciba Geigy | Mischung zum Überziehen von Rektal-Kapseln |
| DE1617671C3 (de) * | 1967-03-07 | 1980-07-03 | A. Nattermann & Cie Gmbh, 5000 Koeln | Weichgelatine-Kapseln mit erhöhter Wärmestabilität |
| DE1767425B2 (de) * | 1968-05-09 | 1973-05-17 | R P Scherer GmbH, 6930 Eberbach | Verfahren zur herstellung von magensaftresistenten gelatinekapseln |
| BE757715A (fr) * | 1969-10-21 | 1971-04-20 | Ciba Geigy | Revetement pour capsules en gelatine et procede pour leur preparation |
-
1979
- 1979-02-01 DE DE2903778A patent/DE2903778C2/de not_active Expired
-
1980
- 1980-01-15 AT AT0019280A patent/AT372607B/de not_active IP Right Cessation
- 1980-01-16 IL IL59137A patent/IL59137A/xx unknown
- 1980-01-16 IT IT8067057A patent/IT8067057A0/it unknown
- 1980-01-17 PT PT70706A patent/PT70706A/de unknown
- 1980-01-21 SE SE8000467A patent/SE8000467L/ not_active Application Discontinuation
- 1980-01-21 GR GR60993A patent/GR70084B/el unknown
- 1980-01-23 DD DD80218609A patent/DD148584A5/de unknown
- 1980-01-23 ZA ZA00800382A patent/ZA80382B/xx unknown
- 1980-01-23 AU AU54887/80A patent/AU5488780A/en not_active Abandoned
- 1980-01-24 AR AR279725A patent/AR223202A1/es active
- 1980-01-25 JP JP769480A patent/JPS55104212A/ja active Pending
- 1980-01-25 GB GB8002576A patent/GB2043442A/en not_active Withdrawn
- 1980-01-28 FR FR8001763A patent/FR2447720A1/fr not_active Withdrawn
- 1980-01-28 CS CS80585A patent/CS222299B2/cs unknown
- 1980-01-28 HU HU80177A patent/HU183053B/hu unknown
- 1980-01-31 DK DK42880A patent/DK42880A/da not_active Application Discontinuation
- 1980-01-31 BE BE0/199196A patent/BE881462A/fr not_active IP Right Cessation
- 1980-01-31 NL NL8000634A patent/NL8000634A/nl not_active Application Discontinuation
- 1980-01-31 CA CA000344841A patent/CA1142084A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5595762A (en) * | 1992-11-30 | 1997-01-21 | Laboratoires Virbac | Stabilized pulverulent active agents, compositions containing them, process for obtaining them and their applications |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA80382B (en) | 1981-01-28 |
| ATA19280A (de) | 1983-03-15 |
| JPS55104212A (en) | 1980-08-09 |
| FR2447720A1 (fr) | 1980-08-29 |
| AT372607B (de) | 1983-10-25 |
| DD148584A5 (de) | 1981-06-03 |
| IL59137A (en) | 1983-10-31 |
| GR70084B (de) | 1982-07-30 |
| HU183053B (en) | 1984-04-28 |
| GB2043442A (en) | 1980-10-08 |
| DK42880A (da) | 1980-08-02 |
| PT70706A (de) | 1980-02-01 |
| SE8000467L (sv) | 1980-08-02 |
| DE2903778A1 (de) | 1980-08-07 |
| CS222299B2 (en) | 1983-06-24 |
| BE881462A (fr) | 1980-05-16 |
| DE2903778C2 (de) | 1982-06-03 |
| AU5488780A (en) | 1980-08-07 |
| NL8000634A (nl) | 1980-08-05 |
| IT8067057A0 (it) | 1980-01-16 |
| AR223202A1 (es) | 1981-07-31 |
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Effective date: 20000301 |