CA1236113A - Therapeutically useful 1-alkyl-2-aminotetralin derivatives - Google Patents
Therapeutically useful 1-alkyl-2-aminotetralin derivativesInfo
- Publication number
- CA1236113A CA1236113A CA000401881A CA401881A CA1236113A CA 1236113 A CA1236113 A CA 1236113A CA 000401881 A CA000401881 A CA 000401881A CA 401881 A CA401881 A CA 401881A CA 1236113 A CA1236113 A CA 1236113A
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- carbon atoms
- methyl
- formula
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- -1 7-hydroxy-1- methyl-2-(di-n-propyl-amino)-1,2,3,4-tetrahydronaphthalene Chemical compound 0.000 claims description 14
- 125000005336 allyloxy group Chemical group 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 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 claims description 9
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- ORYMAZZENFCTAE-CJNGLKHVSA-N (5r,6s)-6-(dipropylamino)-5-methyl-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2[C@@H](C)[C@@H](N(CCC)CCC)CCC2=C1O ORYMAZZENFCTAE-CJNGLKHVSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000002081 enamines Chemical class 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- ADVQBNGWEGSMGY-UHFFFAOYSA-N (5-methoxy-1-methyl-1,2,3,4-tetrahydronaphthalen-2-yl)-dipropylazanium;chloride Chemical compound Cl.C1=CC=C2C(C)C(N(CCC)CCC)CCC2=C1OC ADVQBNGWEGSMGY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
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- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 4
- ORYMAZZENFCTAE-UHFFFAOYSA-N 6-(dipropylamino)-5-methyl-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2C(C)C(N(CCC)CCC)CCC2=C1O ORYMAZZENFCTAE-UHFFFAOYSA-N 0.000 claims 3
- ADVQBNGWEGSMGY-CVLQQERVSA-N (1r,2s)-5-methoxy-1-methyl-n,n-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC=C2[C@@H](C)[C@@H](N(CCC)CCC)CCC2=C1OC ADVQBNGWEGSMGY-CVLQQERVSA-N 0.000 claims 2
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- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 13
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 17
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
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- IPHFEAMSIOVYCA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene;hydrochloride Chemical compound Cl.C1=CC=C2CCCCC2=C1 IPHFEAMSIOVYCA-UHFFFAOYSA-N 0.000 description 9
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8102908 | 1981-05-08 | ||
| SE8102908-4 | 1981-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1236113A true CA1236113A (en) | 1988-05-03 |
Family
ID=20343779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000401881A Expired CA1236113A (en) | 1981-05-08 | 1982-04-28 | Therapeutically useful 1-alkyl-2-aminotetralin derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4876284A (enExample) |
| EP (1) | EP0064964B1 (enExample) |
| JP (1) | JPS57192344A (enExample) |
| AT (1) | ATE8874T1 (enExample) |
| AU (2) | AU554206B2 (enExample) |
| CA (1) | CA1236113A (enExample) |
| DE (1) | DE3260529D1 (enExample) |
| DK (1) | DK164937C (enExample) |
| ES (4) | ES8306708A1 (enExample) |
| FI (1) | FI78067C (enExample) |
| GR (1) | GR77121B (enExample) |
| IE (1) | IE53143B1 (enExample) |
| IL (1) | IL65501A (enExample) |
| NO (1) | NO152902C (enExample) |
| NZ (1) | NZ200526A (enExample) |
| PH (2) | PH18065A (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL65501A (en) * | 1981-05-08 | 1986-04-29 | Astra Laekemedel Ab | 1-alkyl-2-aminotetralin derivatives,process for their preparation and pharmaceutical compositions containing them |
| US4657925A (en) * | 1984-08-13 | 1987-04-14 | Nelson Research & Development Co. | Method and compositions for reducing the intraocular pressure of mammals |
| US4743618A (en) * | 1983-01-03 | 1988-05-10 | Nelson Research & Development Co. | Substituted 2-aminotetralins |
| US4722933A (en) * | 1985-12-20 | 1988-02-02 | Nelson Research & Development Co. | Substituted 2-aminotetralins |
| GB2157950B (en) * | 1984-05-04 | 1988-11-02 | Nelson Res & Dev | Selective d-2 dopamine receptor agonist |
| AU573828B2 (en) * | 1984-05-17 | 1988-06-23 | E.R. Squibb & Sons, Inc. | Tetrahydronaphthalenols |
| DE3479314D1 (en) * | 1984-05-22 | 1989-09-14 | Nelson Res & Dev | Substituted 2-aminotetralins and processes for synthesis |
| DE3718317A1 (de) * | 1986-12-10 | 1988-06-16 | Bayer Ag | Substituierte basische 2-aminotetraline |
| US5091526A (en) * | 1988-07-29 | 1992-02-25 | Schering Corporation | Process for the enantiospecific synthesis of intermediates for hexahydro-benzo[d]-naphtho[2,1-b]azepines |
| WO1990001476A1 (en) * | 1988-07-29 | 1990-02-22 | Schering Corporation | A PROCESS FOR THE ENANTIOSPECIFIC SYNTHESIS OF INTERMEDIATES FOR HEXAHYDRO-BENZO[d]NAPHTHO[2,1-b]AZEPINES |
| CA1335106C (en) * | 1989-02-27 | 1995-04-04 | John Mehnert Schaus | Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes |
| SE8901889D0 (sv) * | 1989-05-26 | 1989-05-26 | Astra Ab | Novel 8-substituted-2-aminotetralines |
| JP2785879B2 (ja) * | 1989-05-31 | 1998-08-13 | ジ・アップジョン・カンパニー | 治療学的に有用な２―アミノテトラリン誘導体 |
| IT1232160B (it) * | 1989-07-31 | 1992-01-25 | Sigma Tau Ind Farmaceuti | 2-(n-acil)ammino-6,7-dimetossi tetraline, procedimento per la loro preparazione e composizioni farmaceutiche ad attivita' antiipertensiva che le contengono |
| CA2071897A1 (en) * | 1989-12-28 | 1991-06-29 | Richard A. Glennon | Sigma receptor ligands and the use thereof |
| EP0471515B1 (en) * | 1990-08-15 | 1997-03-05 | Eli Lilly And Company | Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes, 3-aminochromanes and 3-aminothiochromanes |
| CA2106197A1 (en) * | 1991-04-26 | 1992-10-27 | Montford F. Piercey | Method of treating/preventing substance abuse |
| AU676993B2 (en) * | 1991-06-27 | 1997-04-10 | Virginia Commonwealth University | Sigma receptor ligands and the use thereof |
| IT1251877B (it) * | 1991-09-26 | 1995-05-26 | Zambon Spa | Processo per la preparazione di 2-ammino-5,6 dimetossi-tetralina |
| EP0697894A4 (en) * | 1993-03-31 | 1996-05-01 | Univ Pennsylvania | DOPAMINE D-3 AND SEROTONIN (5-HT 1A) RECEPTOR LIGANDS AND IMAGING AGENTS |
| AU7177694A (en) * | 1993-06-23 | 1995-01-17 | Cambridge Neuroscience, Inc. | Sigma receptor ligands and the use thereof |
| GB9315566D0 (en) * | 1993-07-28 | 1993-09-08 | Smithkline Beecham Plc | Medicaments |
| DE69608551T2 (de) * | 1995-03-27 | 2001-01-18 | Smithkline Beecham P.L.C., Brentford | Bicyclische amin-derivate und ihre verwendung als antipsychotische wirkstoffe |
| US5646188A (en) * | 1995-07-05 | 1997-07-08 | Teva Pharmaceutical Industries, Ltd. | Polyamine derivatives of 1-aminoindan |
| NZ510988A (en) * | 1998-10-07 | 2005-01-28 | Ortho Mcneil Pharm Inc | N-aralkylaminotetralins useful as ligands for the neuropeptide Y5 receptor |
| AU2003241453A1 (en) | 2002-05-17 | 2003-12-02 | Janssen Pharmaceutica N.V. | Aminotetralin-derived urea modulators of vanilloid vr1 receptor |
| EP2098511A1 (en) | 2008-03-07 | 2009-09-09 | Solvias AG | Process for preparing compounds containing a hydronaphtalene structure with an unsymmetrically substituted benzene ring |
| DE102010020553A1 (de) | 2010-05-14 | 2011-11-17 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 8-Alkoxy-2-aminotetralin-Derivate und ihre Verwendung |
| PL2875003T3 (pl) | 2012-07-20 | 2017-05-31 | Bayer Pharma Aktiengesellschaft | Nowe kwasy 5-aminotetrahydrochinolino-2-karboksylowe i ich zastosowanie |
| JP6324956B2 (ja) | 2012-07-20 | 2018-05-16 | バイエル・ファルマ・アクティエンゲゼルシャフト | 置換アミノインダン−およびアミノテトラリンカルボン酸ならびにその使用 |
| TW202342034A (zh) | 2021-12-29 | 2023-11-01 | 德商拜耳廠股份有限公司 | 心肺病症之治療 |
| AU2022429647A1 (en) | 2021-12-29 | 2024-07-04 | Bayer Aktiengesellschaft | Process for preparing (5s)-{[2-(4-carboxyphenyl)ethyl] |2-(2-{|3-chloro-4'-(trifluoromethyl)biphenyl-4- yl]methoxy}phenyl)ethyl]aminol-5,6,7,8-tetrahydroquinoline-2-carboxylic acid and its crystalline forms for use as pharmaceutically active compound |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1017359A (en) * | 1972-07-03 | 1977-09-13 | Frederic P. Hauck | Substituted cyclic polymethylene phenols |
| JPS5124508B2 (enExample) * | 1972-08-14 | 1976-07-24 | ||
| DE2752659A1 (de) * | 1976-12-07 | 1978-06-08 | Sandoz Ag | Neue tetralinderivate, ihre herstellung und verwendung |
| EP0026848B1 (de) * | 1979-09-14 | 1983-05-04 | Sandoz Ag | Tetralinderivate, ihre Herstellung und Heilmittel, welche diese Verbindungen enthalten |
| AU7179781A (en) * | 1980-05-29 | 1981-12-21 | Astra Lakemedel Aktiebolag | Therapeutically useful tetralin derivatives |
| IL65501A (en) * | 1981-05-08 | 1986-04-29 | Astra Laekemedel Ab | 1-alkyl-2-aminotetralin derivatives,process for their preparation and pharmaceutical compositions containing them |
| FR2512814A1 (fr) * | 1981-09-16 | 1983-03-18 | Synthelabo | Derives d'amino-2 tetrahydro-1,2,3,4 naphtalene, leur preparation et leur application en therapeutique |
-
1982
- 1982-04-15 IL IL65501A patent/IL65501A/xx not_active IP Right Cessation
- 1982-04-28 CA CA000401881A patent/CA1236113A/en not_active Expired
- 1982-05-05 NZ NZ200526A patent/NZ200526A/en unknown
- 1982-05-05 AU AU83409/82A patent/AU554206B2/en not_active Ceased
- 1982-05-05 PH PH27236A patent/PH18065A/en unknown
- 1982-05-06 IE IE1076/82A patent/IE53143B1/en not_active IP Right Cessation
- 1982-05-06 FI FI821598A patent/FI78067C/fi not_active IP Right Cessation
- 1982-05-06 EP EP82850102A patent/EP0064964B1/en not_active Expired
- 1982-05-06 AT AT82850102T patent/ATE8874T1/de active
- 1982-05-06 DK DK202882A patent/DK164937C/da not_active IP Right Cessation
- 1982-05-06 DE DE8282850102T patent/DE3260529D1/de not_active Expired
- 1982-05-06 NO NO821494A patent/NO152902C/no unknown
- 1982-05-07 JP JP57075554A patent/JPS57192344A/ja active Granted
- 1982-05-07 GR GR68101A patent/GR77121B/el unknown
- 1982-05-07 ES ES511986A patent/ES8306708A1/es not_active Expired
-
1983
- 1983-02-08 ES ES519615A patent/ES519615A0/es active Granted
-
1984
- 1984-01-31 ES ES529311A patent/ES8506591A1/es not_active Expired
- 1984-03-19 AU AU25879/84A patent/AU572497B2/en not_active Ceased
- 1984-06-08 PH PH30792A patent/PH19585A/en unknown
- 1984-09-13 ES ES535882A patent/ES8602603A1/es not_active Expired
-
1988
- 1988-01-11 US US07/143,260 patent/US4876284A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |