FI71319C - Foerfarande foer framstaellning av terapeutiskt anvaendbart vicaminsackarinat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbart vicaminsackarinat Download PDFInfo
- Publication number
- FI71319C FI71319C FI812602A FI812602A FI71319C FI 71319 C FI71319 C FI 71319C FI 812602 A FI812602 A FI 812602A FI 812602 A FI812602 A FI 812602A FI 71319 C FI71319 C FI 71319C
- Authority
- FI
- Finland
- Prior art keywords
- vincamine
- saccharinate
- reacted
- solution
- saccharin
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title 2
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 claims abstract description 91
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229960002726 vincamine Drugs 0.000 claims abstract description 44
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 19
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 12
- 229940081974 saccharin Drugs 0.000 claims description 10
- 235000019204 saccharin Nutrition 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- RXPRRQLKFXBCSJ-LLQWEQGGSA-N ac1l3o7e Chemical compound C1=CC=C2C(CCN3CCC4)=C5C3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-LLQWEQGGSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- -1 alkali metal saccharinate Chemical class 0.000 claims description 3
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- HEKURBKACCBNEJ-UHFFFAOYSA-M potassium;1,1-dioxo-1,2-benzothiazol-2-id-3-one Chemical compound [K+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 HEKURBKACCBNEJ-UHFFFAOYSA-M 0.000 claims description 2
- 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 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- KHZGWDJDORKMJQ-OILCKBBASA-N vincamine tartrate Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 KHZGWDJDORKMJQ-OILCKBBASA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- BDWFYHUDXIDTIU-UHFFFAOYSA-N ethanol;propane-1,2,3-triol Chemical compound CCO.OCC(O)CO BDWFYHUDXIDTIU-UHFFFAOYSA-N 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002585 base Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- OXLXSOPFNVKUMU-UHFFFAOYSA-N 1,4-dioctoxy-1,4-dioxobutane-2-sulfonic acid Chemical class CCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCC OXLXSOPFNVKUMU-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 208000002381 Brain Hypoxia Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 241000863486 Vinca minor Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 201000007201 aphasia Diseases 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3031953 | 1980-08-25 | ||
| DE3031953 | 1980-08-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI812602L FI812602L (fi) | 1982-02-26 |
| FI71319B FI71319B (fi) | 1986-09-09 |
| FI71319C true FI71319C (fi) | 1986-12-19 |
Family
ID=6110316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI812602A FI71319C (fi) | 1980-08-25 | 1981-08-24 | Foerfarande foer framstaellning av terapeutiskt anvaendbart vicaminsackarinat |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4362730A (xx) |
| EP (1) | EP0046506B1 (xx) |
| JP (1) | JPS5775982A (xx) |
| KR (1) | KR840000702B1 (xx) |
| AT (1) | ATE7698T1 (xx) |
| DE (1) | DE3163875D1 (xx) |
| DK (1) | DK151806C (xx) |
| FI (1) | FI71319C (xx) |
| GR (1) | GR75738B (xx) |
| HU (1) | HU187626B (xx) |
| IE (1) | IE51568B1 (xx) |
| YU (1) | YU42246B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4460560A (en) * | 1982-06-18 | 1984-07-17 | University Of Southern California | Drug delivery by polymeric carriers |
| CH663789A5 (it) * | 1985-08-27 | 1988-01-15 | Arysearch Arylan Ag | Procedimento per la produzione del sale 2-chetoglutarato di vincamina. |
| ES2097703B1 (es) * | 1995-04-12 | 1997-12-01 | Decox S L | Una nueva composicion estimulante de la actividad cerebral basada en alcaloides de nucleo de eburnamenina, y sus metodos de preparacion. |
| JP2003508430A (ja) * | 1999-08-31 | 2003-03-04 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | トラマドールサッカリナートを含有する徐放性投薬形 |
| DE10109763A1 (de) * | 2001-02-28 | 2002-09-05 | Gruenenthal Gmbh | Pharmazeutische Salze |
| US20050176790A1 (en) * | 2001-02-28 | 2005-08-11 | Johannes Bartholomaus | Pharmaceutical salts |
| DE10130504B4 (de) | 2001-06-25 | 2005-02-03 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Xanthin- und Phenazon-Acesulfam-H-Komplexe mit verbessertem Geschmack, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CA2709219A1 (en) * | 2007-12-12 | 2009-06-18 | Ultimorphix Technologies B.V. | Solid forms of tenofovir disoproxil |
| US7935817B2 (en) * | 2008-03-31 | 2011-05-03 | Apotex Pharmachem Inc. | Salt form and cocrystals of adefovir dipivoxil and processes for preparation thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2134714A (en) * | 1936-11-25 | 1938-11-01 | Jacob A Glassman | Saccharine-aspirin tablet |
| US2538645A (en) * | 1948-10-18 | 1951-01-16 | William F Hamilton | Vasoconstrictor compounds of saccharin and pharmaceutical compositions produced therefrom |
| FR2193586A1 (en) * | 1972-07-31 | 1974-02-22 | Centre Etd Ind Pharma | Vincamine dioctyl sulphosuccinate for medical use - for humans and animals as a cerebral and coronary vasodilator, with no bitter taste |
| FR2193587A1 (en) * | 1972-07-31 | 1974-02-22 | Centre Etd Ind Pharma | Vincamine lauryl sulphate compsns - for humans and animals, as a cerebral and coronary vasodilator, without bitter taste |
| ES430063A1 (es) * | 1974-09-14 | 1976-10-01 | Corbera Gubern | Procedimiento para la obtencion de una sal del acido alfa- cetoglutarico. |
| JPS5840529B2 (ja) * | 1975-09-29 | 1983-09-06 | 明治製菓株式会社 | ケイコウヨウセイザイノセイホウ |
| GB1549501A (en) * | 1976-06-03 | 1979-08-08 | Mora E | Adducts of vincamine and apovincamine |
-
1981
- 1981-07-16 US US06/283,706 patent/US4362730A/en not_active Expired - Fee Related
- 1981-07-17 DE DE8181105633T patent/DE3163875D1/de not_active Expired
- 1981-07-17 AT AT81105633T patent/ATE7698T1/de active
- 1981-07-17 EP EP81105633A patent/EP0046506B1/de not_active Expired
- 1981-08-19 GR GR65818A patent/GR75738B/el unknown
- 1981-08-20 YU YU2016/81A patent/YU42246B/xx unknown
- 1981-08-24 FI FI812602A patent/FI71319C/fi not_active IP Right Cessation
- 1981-08-24 IE IE1933/81A patent/IE51568B1/en unknown
- 1981-08-24 KR KR1019810003087A patent/KR840000702B1/ko active
- 1981-08-24 HU HU812452A patent/HU187626B/hu not_active IP Right Cessation
- 1981-08-24 DK DK373181A patent/DK151806C/da not_active IP Right Cessation
- 1981-08-24 JP JP56132555A patent/JPS5775982A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI71319B (fi) | 1986-09-09 |
| JPS5775982A (en) | 1982-05-12 |
| YU42246B (en) | 1988-06-30 |
| FI812602L (fi) | 1982-02-26 |
| DK373181A (da) | 1982-02-26 |
| JPS6230994B2 (xx) | 1987-07-06 |
| HU187626B (en) | 1986-02-28 |
| GR75738B (xx) | 1984-08-02 |
| DK151806B (da) | 1988-01-04 |
| DE3163875D1 (en) | 1984-07-05 |
| IE51568B1 (en) | 1987-01-21 |
| YU201681A (en) | 1984-02-29 |
| US4362730A (en) | 1982-12-07 |
| ATE7698T1 (de) | 1984-06-15 |
| KR830006286A (ko) | 1983-09-20 |
| KR840000702B1 (ko) | 1984-05-21 |
| IE811933L (en) | 1982-02-25 |
| EP0046506B1 (de) | 1984-05-30 |
| EP0046506A1 (de) | 1982-03-03 |
| DK151806C (da) | 1988-06-06 |
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