AT392904B - Verfahren zur herstellung einer zur oralen verabreichung von etoposid bestimmten weichgelantinekapsel - Google Patents
Verfahren zur herstellung einer zur oralen verabreichung von etoposid bestimmten weichgelantinekapsel Download PDFInfo
- Publication number
- AT392904B AT392904B AT819/85A AT81985A AT392904B AT 392904 B AT392904 B AT 392904B AT 819/85 A AT819/85 A AT 819/85A AT 81985 A AT81985 A AT 81985A AT 392904 B AT392904 B AT 392904B
- Authority
- AT
- Austria
- Prior art keywords
- etoposide
- weight
- acid
- water
- solution
- Prior art date
Links
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 title claims description 47
- 229960005420 etoposide Drugs 0.000 title claims description 44
- 239000002775 capsule Substances 0.000 title description 17
- 238000004519 manufacturing process Methods 0.000 title description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 claims description 17
- WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 claims description 17
- 235000019441 ethanol Nutrition 0.000 claims description 13
- 239000007903 gelatin capsule Substances 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 43
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229960004106 citric acid Drugs 0.000 description 9
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003613 bile acid Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 230000037406 food intake Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960004543 anhydrous citric acid Drugs 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 210000003736 gastrointestinal content Anatomy 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 description 1
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003005 anticarcinogenic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
- 229960001091 chenodeoxycholic acid Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079920 digestives acid preparations Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229960002972 glutethimide Drugs 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000015205 orange juice Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
- 229960001237 podophyllotoxin Drugs 0.000 description 1
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical group [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
-
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59114484A | 1984-03-19 | 1984-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA81985A ATA81985A (de) | 1990-12-15 |
| AT392904B true AT392904B (de) | 1991-07-10 |
Family
ID=24365235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT819/85A AT392904B (de) | 1984-03-19 | 1985-03-19 | Verfahren zur herstellung einer zur oralen verabreichung von etoposid bestimmten weichgelantinekapsel |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS60209516A (OSRAM) |
| KR (1) | KR850006136A (OSRAM) |
| AT (1) | AT392904B (OSRAM) |
| AU (1) | AU571308B2 (OSRAM) |
| BE (1) | BE901963A (OSRAM) |
| CA (1) | CA1238578A (OSRAM) |
| CH (1) | CH662731A5 (OSRAM) |
| DE (1) | DE3509741A1 (OSRAM) |
| DK (1) | DK164535C (OSRAM) |
| EG (1) | EG17521A (OSRAM) |
| ES (1) | ES8702140A1 (OSRAM) |
| FI (1) | FI84023C (OSRAM) |
| FR (1) | FR2561104B1 (OSRAM) |
| GB (1) | GB2155789B (OSRAM) |
| GR (1) | GR850688B (OSRAM) |
| IE (1) | IE58340B1 (OSRAM) |
| IL (1) | IL74615A (OSRAM) |
| IT (1) | IT1187640B (OSRAM) |
| LU (1) | LU85812A1 (OSRAM) |
| MY (1) | MY101916A (OSRAM) |
| NL (1) | NL8500739A (OSRAM) |
| NO (1) | NO170569C (OSRAM) |
| NZ (1) | NZ211078A (OSRAM) |
| OA (1) | OA07968A (OSRAM) |
| PT (1) | PT80131B (OSRAM) |
| SE (1) | SE8501312L (OSRAM) |
| YU (1) | YU45243B (OSRAM) |
| ZA (1) | ZA851935B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60239418A (ja) * | 1984-05-15 | 1985-11-28 | Nippon Kayaku Co Ltd | エトポシド軟カプセル製剤 |
| JPS61189230A (ja) * | 1985-02-19 | 1986-08-22 | Nippon Kayaku Co Ltd | エトポシド製剤 |
| DE3629386A1 (de) * | 1986-08-29 | 1988-03-03 | Scherer Gmbh R P | Gelatinekapseln und verfahren zu ihrer herstellung |
| US4927638A (en) * | 1986-10-08 | 1990-05-22 | Bristol-Myers Company | Etoposide solutions |
| US5154930A (en) * | 1987-03-05 | 1992-10-13 | The Liposome Company, Inc. | Pharmacological agent-lipid solution preparation |
| US5376381A (en) * | 1988-02-25 | 1994-12-27 | The Liposome Company, Inc. | Integrity protected gelatin |
| JP2000247911A (ja) * | 1999-02-26 | 2000-09-12 | Hisamitsu Pharmaceut Co Inc | 大腸用吸収促進剤 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2452785A1 (de) * | 1974-11-07 | 1976-05-13 | Universal Oil Prod Co | Verfahren zum betrieb einer verbrennungsmaschine |
| CH580255A5 (OSRAM) * | 1974-06-04 | 1976-09-30 | Calinter Sa | |
| DE2700085A1 (de) * | 1976-07-13 | 1978-01-26 | Lipha | Arzneimittel |
| JPS5350316A (en) * | 1976-10-14 | 1978-05-08 | Takeda Chem Ind Ltd | Drug composition for oral administration |
| DE2809543A1 (de) * | 1978-03-06 | 1979-09-13 | Werner Henke | Verfahren und vorrichtung zum neutralisieren von gasen bei oel- und gasbohrungen |
| FR2410504B1 (OSRAM) * | 1977-12-05 | 1980-08-22 | Air Liquide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60239418A (ja) * | 1984-05-15 | 1985-11-28 | Nippon Kayaku Co Ltd | エトポシド軟カプセル製剤 |
-
1985
- 1985-02-08 NZ NZ211078A patent/NZ211078A/en unknown
- 1985-02-20 AU AU38975/85A patent/AU571308B2/en not_active Ceased
- 1985-03-05 FR FR8503221A patent/FR2561104B1/fr not_active Expired
- 1985-03-14 NL NL8500739A patent/NL8500739A/nl not_active Application Discontinuation
- 1985-03-14 ZA ZA851935A patent/ZA851935B/xx unknown
- 1985-03-14 IT IT19897/85A patent/IT1187640B/it active
- 1985-03-15 YU YU420/85A patent/YU45243B/xx unknown
- 1985-03-15 IL IL74615A patent/IL74615A/xx unknown
- 1985-03-15 FI FI851040A patent/FI84023C/fi not_active IP Right Cessation
- 1985-03-15 NO NO851022A patent/NO170569C/no unknown
- 1985-03-15 IE IE68685A patent/IE58340B1/en not_active IP Right Cessation
- 1985-03-16 EG EG164/85A patent/EG17521A/xx active
- 1985-03-18 DE DE19853509741 patent/DE3509741A1/de not_active Withdrawn
- 1985-03-18 SE SE8501312A patent/SE8501312L/ not_active Application Discontinuation
- 1985-03-18 PT PT80131A patent/PT80131B/pt not_active IP Right Cessation
- 1985-03-18 KR KR1019850001736A patent/KR850006136A/ko not_active Ceased
- 1985-03-18 ES ES541370A patent/ES8702140A1/es not_active Expired
- 1985-03-18 GB GB08506943A patent/GB2155789B/en not_active Expired
- 1985-03-18 BE BE0/214666A patent/BE901963A/fr not_active IP Right Cessation
- 1985-03-18 JP JP60054088A patent/JPS60209516A/ja active Pending
- 1985-03-18 DK DK122285A patent/DK164535C/da not_active IP Right Cessation
- 1985-03-18 CA CA000476750A patent/CA1238578A/en not_active Expired
- 1985-03-18 LU LU85812A patent/LU85812A1/fr unknown
- 1985-03-19 GR GR850688A patent/GR850688B/el unknown
- 1985-03-19 CH CH1223/85A patent/CH662731A5/de not_active IP Right Cessation
- 1985-03-19 AT AT819/85A patent/AT392904B/de not_active IP Right Cessation
- 1985-03-19 OA OA58543A patent/OA07968A/xx unknown
-
1987
- 1987-09-29 MY MYPI87002211A patent/MY101916A/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH580255A5 (OSRAM) * | 1974-06-04 | 1976-09-30 | Calinter Sa | |
| DE2452785A1 (de) * | 1974-11-07 | 1976-05-13 | Universal Oil Prod Co | Verfahren zum betrieb einer verbrennungsmaschine |
| DE2700085A1 (de) * | 1976-07-13 | 1978-01-26 | Lipha | Arzneimittel |
| JPS5350316A (en) * | 1976-10-14 | 1978-05-08 | Takeda Chem Ind Ltd | Drug composition for oral administration |
| FR2410504B1 (OSRAM) * | 1977-12-05 | 1980-08-22 | Air Liquide | |
| DE2809543A1 (de) * | 1978-03-06 | 1979-09-13 | Werner Henke | Verfahren und vorrichtung zum neutralisieren von gasen bei oel- und gasbohrungen |
Non-Patent Citations (5)
| Title |
|---|
| CANCER 40, 633-637, 1977, M. HAUSEN ET AL. * |
| CANCER CHEMOTHERAPY AND PHARMACOLOGY 7, 81-85, 1982 * |
| CANCER TREATMENT REPORTS 60, 943-945, 1976, N.J. NISSEN ET AL. * |
| CANCER TREATMENT REPORTS 63, 485-487, 1979, M.E. LAN ET AL. * |
| F. CAVALLI HANDBUCH DER KOSMETIKA UND RIECHSTOFFE, H.JANISTYN, 3.AUFL. HEIDELBERG, HÜTHIG, VERLAG, 1978, S. 405 * |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| ELJ | Ceased due to non-payment of the annual fee | ||
| REN | Ceased due to non-payment of the annual fee |