FI68807C - Foerfarande foer framstaellning av nya som depressionslaekemedel anvaendbara trans-4-fenyl-1,2,3,4-tetrahydro-1-naftalenaminderivat - Google Patents
Foerfarande foer framstaellning av nya som depressionslaekemedel anvaendbara trans-4-fenyl-1,2,3,4-tetrahydro-1-naftalenaminderivat Download PDFInfo
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- FI68807C FI68807C FI803399A FI803399A FI68807C FI 68807 C FI68807 C FI 68807C FI 803399 A FI803399 A FI 803399A FI 803399 A FI803399 A FI 803399A FI 68807 C FI68807 C FI 68807C
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- trans
- formula
- tetrahydro
- hydrogen
- acid
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- XPLZAZCGEUUFJL-UHFFFAOYSA-N n-benzyl-3-[2-(pyridine-4-carbonyl)hydrazinyl]propanamide;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C[NH2+]C(=O)CCNNC(=O)C1=CC=NC=C1 XPLZAZCGEUUFJL-UHFFFAOYSA-N 0.000 description 1
- IWNASFAWDLBFQQ-UHFFFAOYSA-N n-methyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C12=CC=CC=C2C(=NC)CCC1C1=CC=CC(C(F)(F)F)=C1 IWNASFAWDLBFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000008183 oral pharmaceutical preparation Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- IOXDAYKKVHAKSX-UHFFFAOYSA-N phenyl-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 IOXDAYKKVHAKSX-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002731 protein assay Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 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
- 230000007704 transition Effects 0.000 description 1
- 230000018405 transmission of nerve impulse Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (3)
1. Förfarande för framställning av nya, som depression s läkemedel användbara trans-4-fenyl-1,2,3,4-tetrahydro-5 1-naftalenaminderivat, vilka är trans-isomera baser med formeIn I, _ PlR2 - Wl Y X väri R.| är väte eller en normal alkyl med 1-3 kolatomer, R2 15 är en normal alkyl med 1-3 kolatomer, X och Y är vardera väte, fluor, klor, brom, trifluormetyl eller en alkoxi med 1-3 kolatomer, varvid ätminstone nägondera av X och Y är annat än väte, och W är väte, klor eller en alkoxi med 1-3 kolatomer, samt för framställning av deras farmaceutiskt 20 godtagbara syraadditionssalter, kännetecknat därav, att a) en förening med formeln II 25 (II) Y^^ X 30 väri X och Y anger väte, fluor, klor, brom eller trifluormetyl sä, att ätminstone den ena av X och Y anger annat än väte, och W anger samma som ovan, kondenseras i närvaro av en syrakatalysator med en amin med formeln
35 HNR1R2 44 68807 väri R.j och R2 anger sanana som ovan, för erhällande av, dä R1 är väte, en förening med formeln III (iii) Y X eller, da R^ är en normal alkyl, en förening med formeln IV 10 iPlR2 W--|l (IV) Y X och den erhällna föreningen med formeln III eller IV redu-ceras för erhällande av en blandning av cis- och trans-iso-mera baser med formeln I; eller 20 b) en förening med formeln V X (V) 25 ill väri R^, R2, X, Y och W anger samma som i formel I, hyde-ras för erhällande av en blandning av cis- och trans-iso-30 mera baser med formeln I; en (IS)(IR)-racemisk trans-isomer bas med formeln I, eller ett farmaceutiskt godtagbart syraadditionssalt därav, se-paras frän blandningen som erhällits i skede a) eller ske-de b);
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9023779A | 1979-11-01 | 1979-11-01 | |
US9023779 | 1979-11-01 | ||
US06/184,447 US4556676A (en) | 1979-11-01 | 1980-09-05 | Antidepressant derivatives of trans-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
US18444780 | 1980-09-05 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI803399L FI803399L (fi) | 1981-05-02 |
FI68807B FI68807B (fi) | 1985-07-31 |
FI68807C true FI68807C (fi) | 1985-11-11 |
Family
ID=26782055
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI803399A FI68807C (fi) | 1979-11-01 | 1980-10-30 | Foerfarande foer framstaellning av nya som depressionslaekemedel anvaendbara trans-4-fenyl-1,2,3,4-tetrahydro-1-naftalenaminderivat |
Country Status (18)
Country | Link |
---|---|
US (1) | US4556676A (sv) |
EP (1) | EP0028901B1 (sv) |
KR (1) | KR840002021B1 (sv) |
AR (2) | AR225196A1 (sv) |
AT (1) | ATE2667T1 (sv) |
AU (1) | AU517842B2 (sv) |
CA (1) | CA1130816A (sv) |
DE (1) | DE3062226D1 (sv) |
DK (1) | DK149308C (sv) |
ES (2) | ES8201948A1 (sv) |
FI (1) | FI68807C (sv) |
GR (1) | GR70782B (sv) |
IE (1) | IE50396B1 (sv) |
IL (1) | IL61376A (sv) |
NO (1) | NO149102C (sv) |
PH (1) | PH15468A (sv) |
PT (1) | PT72005B (sv) |
YU (2) | YU41744B (sv) |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8004002L (sv) * | 1980-05-29 | 1981-11-30 | Arvidsson Folke Lars Erik | Terapeutiskt anvendbara tetralinderivat |
US4866208A (en) * | 1981-12-21 | 1989-09-12 | The Dow Chemical Company | Meta-phenylene diamine derivatives |
US4777288A (en) * | 1987-06-11 | 1988-10-11 | Pfizer Inc. | Process for preparing a 4,4-diphenylbutanoic acid derivative |
US4839104A (en) * | 1987-06-11 | 1989-06-13 | Pfizer, Inc. | Process for preparing sertraline intermediates |
FR2623802B1 (fr) * | 1987-11-26 | 1990-05-04 | Lucien Laboratoires | Derives d'amino-4 trifluoromethyl-1 tetralines. leur preparation et leur application en therapeutique |
FR2642065B1 (fr) * | 1989-01-24 | 1991-05-24 | Lipha | Derives d'acides benzocycloalcenyl dihydroxy alcanoiques, procede de preparation et medicaments les contenant |
FR2665443B1 (fr) * | 1990-08-03 | 1992-11-06 | Lucien Laboratoires | Derives d'amino-4-methyl-1-tetralines, leur preparation et leur application en therapeutique. |
US5082970A (en) * | 1991-03-06 | 1992-01-21 | Pfizer Inc. | Process for recycling amine isomer |
GB9114948D0 (en) * | 1991-07-11 | 1991-08-28 | Pfizer Ltd | Process for preparing sertraline intermediates |
US5196607A (en) * | 1992-02-14 | 1993-03-23 | Pfizer Inc. | Process for preparing ketone enantiomer |
US5248699A (en) * | 1992-08-13 | 1993-09-28 | Pfizer Inc. | Sertraline polymorph |
US5466880A (en) * | 1992-09-15 | 1995-11-14 | Pfizer Inc. | Process for preparing ketone enantiomer |
EP0697894A4 (en) * | 1993-03-31 | 1996-05-01 | Univ Pennsylvania | DOPAMINE D-3 AND SEROTONIN (5-HT 1A) RECEPTOR LIGANDS AND IMAGING AGENTS |
ES2108484T3 (es) * | 1993-11-30 | 1997-12-16 | Pfizer | Procedimiento para la preparacion de una tetralona asimetrica. |
US6410794B1 (en) | 1994-12-16 | 2002-06-25 | Uop Llc | Process for preparation of pharmaceutically desired chiral tetralone from tetralones |
US6455736B1 (en) | 1994-12-16 | 2002-09-24 | Uop Llc | Process for preparation of pharmaceutically desired sertraline and sertraline analogs |
HU222341B1 (hu) * | 1996-12-18 | 2003-06-28 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás sertralin előállítására és az eljárásban alkalmazott intermedier |
IN182588B (sv) | 1998-05-12 | 1999-05-08 | Sun Pharmaceutical Ind Ltd | |
IN187170B (sv) | 2000-01-04 | 2002-02-23 | Sun Pharmaceutical Ind Ltd | |
DE10006411C2 (de) * | 2000-02-14 | 2002-03-07 | Huf Huelsbeck & Fuerst Gmbh | Elektronischer Zündanlaßschalter für Kraftfahrzeuge und Reserveschlüssel zur Betätigung desselben |
DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
US6482440B2 (en) | 2000-09-21 | 2002-11-19 | Phase 2 Discovery, Inc. | Long acting antidepressant microparticles |
US6723878B2 (en) | 2001-06-15 | 2004-04-20 | Orion Corporation Fermion | Method for preparing sertraline |
US8134029B2 (en) | 2002-09-16 | 2012-03-13 | Sunovion Pharmaceuticals Inc. | Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine |
US20040087661A1 (en) * | 2002-09-16 | 2004-05-06 | Sepracor, Inc. | Treatment of CNS disorders with trans 4-3(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-napthalenamine |
MXPA05002700A (es) | 2002-09-16 | 2005-09-08 | Sepracor Inc | Tratamiento de trastornos del sistema nervioso central con trans 4-(3,4-diclorofenil)-1,2,3,4-tetrahidro-1-naftalenamina y su formamida. |
DE10334188B4 (de) * | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
DE10334187A1 (de) * | 2003-07-26 | 2005-03-03 | Schwarz Pharma Ag | Substituierte 2-Aminotetraline zur Behandlung von Depressionen |
US20060014838A1 (en) * | 2004-07-14 | 2006-01-19 | Sudhakar Valluri | Process for converting trans-sertraline to cis-sertraline |
CA2614282A1 (en) | 2005-07-06 | 2007-01-11 | Sepracor Inc. | Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders |
WO2007115185A2 (en) * | 2006-03-31 | 2007-10-11 | Sepracor Inc. | Preparation of chiral amides and amines |
US20070282007A1 (en) * | 2006-05-31 | 2007-12-06 | Sepracor Inc. | TREATMENT OF PAIN DISORDERS WITH trans 4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENAMINE AND ITS FORMAMIDE |
EP2029517A2 (en) * | 2006-06-13 | 2009-03-04 | Ramot at Tel-Aviv University Ltd. | Antiproliferative compounds, compositions and methods of use |
EP1987815A1 (en) * | 2007-05-04 | 2008-11-05 | Schwarz Pharma Ag | Oronasopharyngeally deliverable pharmaceutical compositions of dopamine agonists for the prevention and/or treatment of restless limb disorders |
US20100081713A1 (en) * | 2008-03-19 | 2010-04-01 | CombinatoRx, (Singapore) Pte. Ltd. | Compositions and methods for treating viral infections |
US10076503B2 (en) * | 2014-05-13 | 2018-09-18 | Sunovion Pharmaceuticals Inc. | Dosage of dasotraline and method for treatment of ADHD |
EP3142999A4 (en) * | 2014-05-13 | 2017-12-27 | Sunovion Pharmaceuticals Inc. | Methods and compositions of dasotraline for treatment of adhd |
WO2016046669A2 (en) * | 2014-09-27 | 2016-03-31 | Mohan M Alapati | Compositions and methods for the treatment of depression and neurological diseases |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB793853A (en) * | 1954-09-15 | 1958-04-23 | Schering Ag | Manufacture of new 3-amino-indanes |
DE1098511B (de) * | 1959-11-21 | 1961-02-02 | Schering Ag | Verfahren zur Abtrennung von analgetisch wirksamen d-1-Phenyl-3-dimethylaminoindan |
US3704323A (en) * | 1969-12-23 | 1972-11-28 | Squibb & Sons Inc | Indane derivatives |
GB1420472A (en) * | 1972-09-27 | 1976-01-07 | Pfizer | Aminophenyltetralin compounds |
US4029731A (en) * | 1974-11-06 | 1977-06-14 | Pfizer Inc. | Aminophenyltetralin compounds |
US4045488A (en) * | 1974-11-06 | 1977-08-30 | Pfizer Inc. | Aminophenyltetralin compounds |
-
1980
- 1980-09-05 US US06/184,447 patent/US4556676A/en not_active Expired - Lifetime
- 1980-10-28 AT AT80303810T patent/ATE2667T1/de not_active IP Right Cessation
- 1980-10-28 EP EP80303810A patent/EP0028901B1/en not_active Expired
- 1980-10-28 DE DE8080303810T patent/DE3062226D1/de not_active Expired
- 1980-10-29 PH PH24786A patent/PH15468A/en unknown
- 1980-10-30 FI FI803399A patent/FI68807C/fi not_active IP Right Cessation
- 1980-10-30 CA CA363,571A patent/CA1130816A/en not_active Expired
- 1980-10-30 GR GR63248A patent/GR70782B/el unknown
- 1980-10-30 AR AR283061A patent/AR225196A1/es active
- 1980-10-30 YU YU2774/80A patent/YU41744B/xx unknown
- 1980-10-30 IL IL61376A patent/IL61376A/xx unknown
- 1980-10-31 IE IE2260/80A patent/IE50396B1/en not_active IP Right Cessation
- 1980-10-31 KR KR1019800004175A patent/KR840002021B1/ko active
- 1980-10-31 ES ES496441A patent/ES8201948A1/es not_active Expired
- 1980-10-31 DK DK462480A patent/DK149308C/da not_active IP Right Cessation
- 1980-10-31 NO NO803259A patent/NO149102C/no unknown
- 1980-10-31 PT PT72005A patent/PT72005B/pt unknown
- 1980-10-31 AU AU63898/80A patent/AU517842B2/en not_active Expired
-
1981
- 1981-10-06 AR AR286998A patent/AR229106A1/es active
- 1981-11-05 ES ES506893A patent/ES506893A0/es active Granted
-
1983
- 1983-01-07 YU YU33/83A patent/YU42066B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
AR229106A1 (es) | 1983-06-15 |
EP0028901A1 (en) | 1981-05-20 |
DE3062226D1 (en) | 1983-04-07 |
AR225196A1 (es) | 1982-02-26 |
NO149102B (no) | 1983-11-07 |
ES8207120A1 (es) | 1982-09-01 |
IL61376A (en) | 1983-10-31 |
FI68807B (fi) | 1985-07-31 |
IE802260L (en) | 1981-05-01 |
US4556676A (en) | 1985-12-03 |
PT72005B (en) | 1981-08-31 |
YU3383A (en) | 1983-09-30 |
PH15468A (en) | 1983-01-24 |
ES496441A0 (es) | 1982-01-16 |
GR70782B (sv) | 1983-03-23 |
YU277480A (en) | 1983-09-30 |
YU41744B (en) | 1987-12-31 |
IE50396B1 (en) | 1986-04-16 |
ES506893A0 (es) | 1982-09-01 |
FI803399L (fi) | 1981-05-02 |
CA1130816A (en) | 1982-08-31 |
YU42066B (en) | 1988-04-30 |
ATE2667T1 (de) | 1983-03-15 |
EP0028901B1 (en) | 1983-03-02 |
AU517842B2 (en) | 1981-08-27 |
DK149308B (da) | 1986-04-28 |
PT72005A (en) | 1980-11-01 |
KR830004201A (ko) | 1983-07-06 |
DK462480A (da) | 1981-05-02 |
KR840002021B1 (ko) | 1984-11-05 |
NO803259L (no) | 1981-05-04 |
IL61376A0 (en) | 1980-12-31 |
DK149308C (da) | 1986-12-08 |
NO149102C (no) | 1984-02-15 |
AU6389880A (en) | 1981-05-07 |
ES8201948A1 (es) | 1982-01-16 |
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