FI85474C - Foerfarande foer framstaellning av terapeutiskt anvaendbara -karbolin-3-oxadiazolylderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara -karbolin-3-oxadiazolylderivat. Download PDFInfo
- Publication number
- FI85474C FI85474C FI851931A FI851931A FI85474C FI 85474 C FI85474 C FI 85474C FI 851931 A FI851931 A FI 851931A FI 851931 A FI851931 A FI 851931A FI 85474 C FI85474 C FI 85474C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- ch2och3
- same
- defined above
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- -1 isopropoxy, cyclobutyloxy Chemical group 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 3
- 230000000506 psychotropic effect Effects 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ARCSBFATIFHVTF-UHFFFAOYSA-N 3-ethyl-1,2,4-oxadiazole Chemical compound CCC=1N=CON=1 ARCSBFATIFHVTF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960002200 flunitrazepam Drugs 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000004300 GABA-A Receptors Human genes 0.000 description 3
- 108090000839 GABA-A Receptors Proteins 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 210000004129 prosencephalon Anatomy 0.000 description 3
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 3
- FBAOVPVVMDOHPK-UHFFFAOYSA-N 2-(1h-imidazol-2-ylsulfinyl)-1h-imidazole Chemical compound N=1C=CNC=1S(=O)C1=NC=CN1 FBAOVPVVMDOHPK-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
- BIEJGCQUCUJKMA-UHFFFAOYSA-N 4-(methoxymethyl)-5-phenylmethoxy-9h-pyrido[3,4-b]indole-3-carboxylic acid Chemical compound C=12C=3C(COC)=C(C(O)=O)N=CC=3NC2=CC=CC=1OCC1=CC=CC=C1 BIEJGCQUCUJKMA-UHFFFAOYSA-N 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 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
- 241000124008 Mammalia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000258 cyclohexylethoxy group Chemical group [H]C([H])(O*)C([H])([H])C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical compound CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Toxicology (AREA)
- Anesthesiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK240084 | 1984-05-15 | ||
| DK2400/84A DK240084D0 (da) | 1984-05-15 | 1984-05-15 | New beta-carboline-3-oxadiazolyl derivatives |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI851931A0 FI851931A0 (fi) | 1985-05-15 |
| FI851931L FI851931L (fi) | 1985-11-16 |
| FI85474B FI85474B (fi) | 1992-01-15 |
| FI85474C true FI85474C (fi) | 1992-04-27 |
Family
ID=8112111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI851931A FI85474C (fi) | 1984-05-15 | 1985-05-15 | Foerfarande foer framstaellning av terapeutiskt anvaendbara -karbolin-3-oxadiazolylderivat. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4645773A (en, 2012) |
| EP (1) | EP0161574B1 (en, 2012) |
| JP (1) | JPH08825B2 (en, 2012) |
| AT (1) | ATE51622T1 (en, 2012) |
| AU (1) | AU581434B2 (en, 2012) |
| DE (1) | DE3576955D1 (en, 2012) |
| DK (1) | DK240084D0 (en, 2012) |
| ES (2) | ES8703150A1 (en, 2012) |
| FI (1) | FI85474C (en, 2012) |
| GR (1) | GR851145B (en, 2012) |
| HU (1) | HU195507B (en, 2012) |
| IE (1) | IE58115B1 (en, 2012) |
| IL (1) | IL75115A (en, 2012) |
| NO (1) | NO161564C (en, 2012) |
| ZA (1) | ZA853719B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ194747A (en) * | 1979-08-29 | 1988-11-29 | Schering Ag | 9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives |
| DE3535928A1 (de) * | 1985-10-04 | 1987-04-09 | Schering Ag | Tetrahydro-(beta)-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3540653A1 (de) * | 1985-11-13 | 1987-05-14 | Schering Ag | Neue 3-oxadiazol- und 3-carbonsaeure-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel |
| DE3545776A1 (de) * | 1985-12-20 | 1987-06-25 | Schering Ag | 5-aminoalkyl-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel |
| DE3608089A1 (de) * | 1986-03-08 | 1987-09-10 | Schering Ag | Heteroaryl-oxy-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel |
| IL87563A (en) * | 1987-08-28 | 1993-08-18 | Schering Ag | Isoxazole-b-carboline derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5543519A (en) * | 1991-06-15 | 1996-08-06 | Schering Aktiengesellschaft | 3-aryl or 3-hetaryl-β-carbolines, their production and use in pharmaceutical agents |
| DE4120109A1 (de) * | 1991-06-15 | 1992-12-17 | Schering Ag | 3-aryl- oder 3-hetaryl-(beta)-carboline, deren herstellung und verwendung in arzneimitteln |
| DE4130933A1 (de) * | 1991-09-13 | 1993-03-18 | Schering Ag | Neue (beta)-carbolinderivate, deren herstellung und verwendung in arzneimitteln |
| DE60234057D1 (de) | 2001-07-25 | 2009-11-26 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| JP2010503710A (ja) | 2006-09-18 | 2010-02-04 | ラプトール ファーマシューティカル インコーポレイテッド | 受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置 |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| MX2011011833A (es) | 2009-05-06 | 2012-01-27 | Lab Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de partículas de fosfato de calcio-agente activo y métodos para utilizar las mismas. |
| FR2953838B1 (fr) * | 2009-12-10 | 2012-02-24 | Sanofi Aventis | Derives de 9h-beta-carboline (ou 9h-pyridino[3,4-b]indole) trisubstitues, leur preparation et leur utilisation therapeutique |
| FR2953837B1 (fr) * | 2009-12-10 | 2012-03-09 | Sanofi Aventis | Derives 9h-pyridino[3,4-b]indole disubstitues, leur preparation et leur utilisation therapeutique |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| KR102449360B1 (ko) * | 2017-06-02 | 2022-10-04 | 삼성전기주식회사 | 적층 세라믹 커패시터 및 그 실장 기판 |
| US11485734B2 (en) | 2018-10-02 | 2022-11-01 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2C (5-HT2C) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57123180A (en) * | 1980-12-17 | 1982-07-31 | Schering Ag | 3-substituted beta-carboline, manufacture and psychotropic drug containing same |
| DE3240511A1 (de) * | 1982-10-29 | 1984-05-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur herstellung von ss-carbolinderivaten |
| DE3240513A1 (de) * | 1982-10-29 | 1984-05-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Indolderivate, verfahren zu ihrer herstellung und deren verwendung zur weiterverarbeitung |
| DE3335323A1 (de) * | 1983-09-27 | 1985-04-04 | Schering AG, 1000 Berlin und 4709 Bergkamen | Substituierte ss-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
-
1984
- 1984-05-15 DK DK2400/84A patent/DK240084D0/da not_active Application Discontinuation
-
1985
- 1985-04-30 AT AT85105258T patent/ATE51622T1/de not_active IP Right Cessation
- 1985-04-30 DE DE8585105258T patent/DE3576955D1/de not_active Expired - Lifetime
- 1985-04-30 EP EP85105258A patent/EP0161574B1/en not_active Expired - Lifetime
- 1985-05-07 IL IL75115A patent/IL75115A/xx not_active IP Right Cessation
- 1985-05-13 GR GR851145A patent/GR851145B/el unknown
- 1985-05-13 AU AU42412/85A patent/AU581434B2/en not_active Ceased
- 1985-05-14 HU HU851818A patent/HU195507B/hu not_active IP Right Cessation
- 1985-05-14 NO NO851932A patent/NO161564C/no unknown
- 1985-05-14 ES ES543153A patent/ES8703150A1/es not_active Expired
- 1985-05-15 JP JP60101661A patent/JPH08825B2/ja not_active Expired - Lifetime
- 1985-05-15 IE IE120585A patent/IE58115B1/en not_active IP Right Cessation
- 1985-05-15 US US06/734,219 patent/US4645773A/en not_active Expired - Fee Related
- 1985-05-15 ZA ZA853719A patent/ZA853719B/xx unknown
- 1985-05-15 FI FI851931A patent/FI85474C/fi not_active IP Right Cessation
-
1986
- 1986-01-28 ES ES551337A patent/ES8704492A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0161574A2 (en) | 1985-11-21 |
| AU4241285A (en) | 1985-11-21 |
| ES551337A0 (es) | 1987-04-16 |
| ATE51622T1 (de) | 1990-04-15 |
| ES543153A0 (es) | 1987-02-16 |
| NO161564B (no) | 1989-05-22 |
| ES8703150A1 (es) | 1987-02-16 |
| HUT37794A (en) | 1986-02-28 |
| FI85474B (fi) | 1992-01-15 |
| ES8704492A1 (es) | 1987-04-16 |
| US4645773A (en) | 1987-02-24 |
| JPH08825B2 (ja) | 1996-01-10 |
| DK240084D0 (da) | 1984-05-15 |
| EP0161574B1 (en) | 1990-04-04 |
| GR851145B (en, 2012) | 1985-11-25 |
| NO161564C (no) | 1989-08-30 |
| IE851205L (en) | 1985-11-15 |
| IL75115A (en) | 1989-07-31 |
| JPS6140283A (ja) | 1986-02-26 |
| FI851931A0 (fi) | 1985-05-15 |
| ZA853719B (en) | 1986-01-29 |
| IL75115A0 (en) | 1985-09-29 |
| EP0161574A3 (en) | 1987-03-25 |
| FI851931L (fi) | 1985-11-16 |
| DE3576955D1 (de) | 1990-05-10 |
| NO851932L (no) | 1985-11-18 |
| AU581434B2 (en) | 1989-02-23 |
| IE58115B1 (en) | 1993-07-14 |
| HU195507B (en) | 1988-05-30 |
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