FI68518C - Foerfarande foer framstaellning av natriumamoxicillin-preparat - Google Patents
Foerfarande foer framstaellning av natriumamoxicillin-preparat Download PDFInfo
- Publication number
- FI68518C FI68518C FI793049A FI793049A FI68518C FI 68518 C FI68518 C FI 68518C FI 793049 A FI793049 A FI 793049A FI 793049 A FI793049 A FI 793049A FI 68518 C FI68518 C FI 68518C
- Authority
- FI
- Finland
- Prior art keywords
- solution
- sodium
- drying
- amoxicillin
- freeze
- Prior art date
Links
- BYHDFCISJXIVBV-YWUHCJSESA-M amoxicillin sodium Chemical compound [Na+].C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)=CC=C(O)C=C1 BYHDFCISJXIVBV-YWUHCJSESA-M 0.000 title description 2
- 235000013399 edible fruits Nutrition 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 66
- 238000002360 preparation method Methods 0.000 claims description 46
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 40
- 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 description 33
- 229910052708 sodium Inorganic materials 0.000 claims description 33
- 239000011734 sodium Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- 238000004108 freeze drying Methods 0.000 claims description 24
- 229960003022 amoxicillin Drugs 0.000 claims description 23
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 23
- 238000007710 freezing Methods 0.000 claims description 16
- 230000008014 freezing Effects 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 229960004920 amoxicillin trihydrate Drugs 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000011049 filling Methods 0.000 claims description 5
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000011146 sterile filtration Methods 0.000 claims description 3
- 229960002793 amoxicillin sodium Drugs 0.000 claims description 2
- ILVPFTMKCHREDJ-UHFFFAOYSA-N methyl 5-amino-2-fluorobenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1F ILVPFTMKCHREDJ-UHFFFAOYSA-N 0.000 claims description 2
- 101100506443 Danio rerio helt gene Proteins 0.000 claims 1
- 101100506445 Mus musculus Helt gene Proteins 0.000 claims 1
- MQXQVCLAUDMCEF-CWLIKTDRSA-N amoxicillin trihydrate Chemical compound O.O.O.C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 MQXQVCLAUDMCEF-CWLIKTDRSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 67
- 238000001035 drying Methods 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000007864 aqueous solution Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007857 degradation product Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000723 ampicillin Drugs 0.000 description 4
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229930182555 Penicillin Natural products 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- -1 ampicillin Chemical class 0.000 description 2
- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical compound [Na+].C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)=CC=CC=C1 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940083555 sodium cephalothin Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960001931 ampicillin sodium Drugs 0.000 description 1
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019448 polyvinylpyrrolidone-vinyl acetate copolymer Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K31/33—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
-
- 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
- A61K47/02—Inorganic compounds
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7809986A NL7809986A (nl) | 1978-10-03 | 1978-10-03 | Werkwijze voor het bereiden van natrium amoxicilline geschikt voor injectiepreparaten, alsmede deze verbin- ding bevattende gedoseerde injectiepreparaten en de bereiding ervan. |
| NL7809986 | 1978-10-03 | ||
| NL7900021A NL7900021A (nl) | 1979-01-03 | 1979-01-03 | Werkwijze voor het bereiden van natriumamoxicilline geschikt voor injectiepreparaten, alsmede deze verbin- ding bevattende gedoseerde injectiepreparaten en de be- reiding ervan. |
| NL7900021 | 1979-01-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI793049A7 FI793049A7 (fi) | 1980-04-04 |
| FI68518B FI68518B (fi) | 1985-06-28 |
| FI68518C true FI68518C (fi) | 1985-10-10 |
Family
ID=26645454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI793049A FI68518C (fi) | 1978-10-03 | 1979-10-02 | Foerfarande foer framstaellning av natriumamoxicillin-preparat |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4607029A (de) |
| EP (1) | EP0009845B2 (de) |
| DE (1) | DE2963947D1 (de) |
| DK (1) | DK157660C (de) |
| ES (1) | ES484698A1 (de) |
| FI (1) | FI68518C (de) |
| FR (1) | FR2437835A1 (de) |
| GR (1) | GR71663B (de) |
| IE (1) | IE48953B1 (de) |
| LU (1) | LU81753A1 (de) |
| NO (1) | NO155009C (de) |
| PT (1) | PT70225A (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8002636A (nl) * | 1980-05-08 | 1981-12-01 | Gist Brocades Nv | Solvaat van amoxicilline, werkwijze ter bereiding hiervan en werkwijze ter bereiding van injectiepreparaten uit dit solvaat. |
| CA1209477A (en) * | 1981-03-26 | 1986-08-12 | Bruce E. Haeger | Composition of matter comprising a lyophilized preparation of a penicillin derivative |
| ES8502863A1 (es) * | 1982-09-10 | 1985-02-01 | Glaxo Group Ltd | Un procedimiento para la produccion de un recipiente hermeticamente cerrado que contiene al menos un antibiotico de beta-lactama. |
| GB8919172D0 (en) * | 1989-08-23 | 1989-10-04 | Univ Nottingham | Useful composition |
| EP1838287B1 (de) * | 2005-01-07 | 2012-05-23 | Sandoz Ag | Verfahren zur granulatherstellung mit amoxicillin |
| CN104689302B (zh) * | 2015-02-05 | 2017-06-23 | 通化东宝药业股份有限公司 | 一种地特胰岛素注射液的制备方法及其制备的地特胰岛素注射液 |
| CN113577317A (zh) * | 2021-07-30 | 2021-11-02 | 华北制药集团先泰药业有限公司 | 一种无菌阿莫西林的制备方法 |
| CN116396307A (zh) * | 2023-04-04 | 2023-07-07 | 内蒙古联邦动保药品有限公司 | 一种阿莫西林钠的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969524A (en) * | 1974-08-13 | 1976-07-13 | Hoffmann-La Roche Inc. | Stable amoxicillin dosage form |
| US4024244A (en) * | 1974-09-18 | 1977-05-17 | Beecham Group Limited | Amoxicillin derivatives |
| GB1463563A (en) * | 1974-10-10 | 1977-02-02 | Beecham Group Ltd | Pharmaceutical compositions |
-
1979
- 1979-09-25 PT PT70225A patent/PT70225A/pt unknown
- 1979-09-27 DE DE7979200545T patent/DE2963947D1/de not_active Expired
- 1979-09-27 EP EP79200545A patent/EP0009845B2/de not_active Expired
- 1979-10-02 GR GR60166A patent/GR71663B/el unknown
- 1979-10-02 NO NO793164A patent/NO155009C/no unknown
- 1979-10-02 DK DK413279A patent/DK157660C/da not_active IP Right Cessation
- 1979-10-02 FI FI793049A patent/FI68518C/fi not_active IP Right Cessation
- 1979-10-02 IE IE1875/79A patent/IE48953B1/en not_active IP Right Cessation
- 1979-10-03 FR FR7924654A patent/FR2437835A1/fr active Granted
- 1979-10-03 LU LU81753A patent/LU81753A1/fr unknown
- 1979-10-03 ES ES484698A patent/ES484698A1/es not_active Expired
-
1985
- 1985-04-23 US US06/726,027 patent/US4607029A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO155009C (no) | 1987-01-28 |
| IE48953B1 (en) | 1985-06-26 |
| US4607029A (en) | 1986-08-19 |
| DK157660B (da) | 1990-02-05 |
| EP0009845B1 (de) | 1982-10-27 |
| DK413279A (da) | 1980-04-04 |
| DK157660C (da) | 1990-07-09 |
| NO155009B (no) | 1986-10-20 |
| EP0009845B2 (de) | 1987-11-11 |
| FR2437835A1 (fr) | 1980-04-30 |
| EP0009845A1 (de) | 1980-04-16 |
| LU81753A1 (fr) | 1980-01-24 |
| NO793164L (no) | 1980-04-09 |
| ES484698A1 (es) | 1980-06-16 |
| FR2437835B1 (de) | 1983-03-18 |
| FI68518B (fi) | 1985-06-28 |
| IE791875L (en) | 1980-04-03 |
| FI793049A7 (fi) | 1980-04-04 |
| PT70225A (en) | 1979-10-01 |
| GR71663B (de) | 1983-06-20 |
| DE2963947D1 (en) | 1982-12-02 |
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