CH661046A5 - Derives de benzodioxinopyrrole et procedes de preparation. - Google Patents
Derives de benzodioxinopyrrole et procedes de preparation. Download PDFInfo
- Publication number
- CH661046A5 CH661046A5 CH5771/83A CH577183A CH661046A5 CH 661046 A5 CH661046 A5 CH 661046A5 CH 5771/83 A CH5771/83 A CH 5771/83A CH 577183 A CH577183 A CH 577183A CH 661046 A5 CH661046 A5 CH 661046A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- trans
- general formula
- solution
- tetrahydro
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 8
- CEOQGBDEHVSEQC-UHFFFAOYSA-N 1h-[1,4]benzodioxino[2,3-b]pyrrole Chemical class O1C2=CC=CC=C2OC2=C1NC=C2 CEOQGBDEHVSEQC-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 95
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- HZMSWIUTALULPV-UWVGGRQHSA-N (3as,9as)-2,3,3a,9a-tetrahydro-1h-[1,4]benzodioxino[2,3-c]pyrrole Chemical compound C1=CC=C2O[C@H]3CNC[C@@H]3OC2=C1 HZMSWIUTALULPV-UWVGGRQHSA-N 0.000 claims description 7
- 125000005002 aryl methyl group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000000935 antidepressant agent Substances 0.000 claims description 6
- 229940005513 antidepressants Drugs 0.000 claims description 6
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- 230000001430 anti-depressive effect Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
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- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- TYUHPIMUSJSGLB-QWRGUYRKSA-N (3as,9as)-2-methyl-1,3,3a,9a-tetrahydro-[1,4]benzodioxino[2,3-c]pyrrole Chemical compound O1C2=CC=CC=C2O[C@@H]2[C@@H]1CN(C)C2 TYUHPIMUSJSGLB-QWRGUYRKSA-N 0.000 claims description 2
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
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- 239000010452 phosphate Substances 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 68
- 239000000203 mixture Substances 0.000 description 60
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- 239000007787 solid Substances 0.000 description 28
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
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- 239000003054 catalyst Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- -1 racemates Chemical class 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
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- 239000003921 oil Substances 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
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- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
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- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
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- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
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- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- OPSXVXRECQNWRM-UHFFFAOYSA-N 2,3,3a,9a-tetrahydro-1h-[1,4]benzodioxino[3,2-b]pyrrole Chemical class O1C2=CC=CC=C2OC2C1CCN2 OPSXVXRECQNWRM-UHFFFAOYSA-N 0.000 description 3
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
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- 230000008713 feedback mechanism Effects 0.000 description 2
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- 238000007918 intramuscular administration Methods 0.000 description 2
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8230379 | 1982-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH661046A5 true CH661046A5 (fr) | 1987-06-30 |
Family
ID=10533819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5771/83A CH661046A5 (fr) | 1982-10-25 | 1983-10-25 | Derives de benzodioxinopyrrole et procedes de preparation. |
Country Status (18)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8410459D0 (en) * | 1984-04-24 | 1984-05-31 | Glaxo Group Ltd | Chemical compounds |
| DE3579189D1 (de) * | 1984-04-24 | 1990-09-20 | Glaxo Group Ltd | Heterocyclische aminoverbindungen. |
| GB8526210D0 (en) * | 1985-10-23 | 1985-11-27 | Glaxo Group Ltd | Chemical compounds |
| US4769367A (en) * | 1984-04-24 | 1988-09-06 | Glaxo Group Limited | Heterocyclic amino compounds |
| GB8526209D0 (en) * | 1985-10-23 | 1985-11-27 | Glaxo Group Ltd | Chemical process |
| US5225431A (en) * | 1987-10-23 | 1993-07-06 | Burroughs Wellcome Co. | Therapeutic substituted indole compounds and compositions thereof |
| GB8828032D0 (en) * | 1988-12-01 | 1989-01-05 | Glaxo Group Ltd | Medicaments |
| DE10107243A1 (de) * | 2001-02-16 | 2002-08-22 | Bayer Ag | Benzodioxinopyrrole, deren Herstellung und Verwendung |
| US8099200B2 (en) | 2005-09-30 | 2012-01-17 | Coombs Joshua D | Vehicle interface based on the weight distribution of a user |
| US20070074922A1 (en) * | 2005-09-30 | 2007-04-05 | Coombs Joshua D | Vehicle interface based on a shift of the torso of a user |
| US20070074921A1 (en) * | 2005-09-30 | 2007-04-05 | Coombs Joshua D | Vehicle interface based on a shift of the appendages of a user |
| US20090076686A1 (en) * | 2005-09-30 | 2009-03-19 | Jeffrey Schox | Vehicle interface to communicate a safety alert mode command |
| US20070078569A1 (en) * | 2005-09-30 | 2007-04-05 | Jeffrey Schox | Vehicle interface to communicate a safety alert mode command |
-
1983
- 1983-10-24 IL IL70034A patent/IL70034A0/xx unknown
- 1983-10-25 US US06/545,191 patent/US4496579A/en not_active Expired - Fee Related
- 1983-10-25 SE SE8305866A patent/SE8305866L/xx not_active Application Discontinuation
- 1983-10-25 BE BE0/211766A patent/BE898072A/fr not_active IP Right Cessation
- 1983-10-25 GB GB08328468A patent/GB2129795B/en not_active Expired
- 1983-10-25 FI FI833887A patent/FI833887A7/fi not_active Application Discontinuation
- 1983-10-25 NL NL8303673A patent/NL8303673A/nl not_active Application Discontinuation
- 1983-10-25 IT IT8349214A patent/IT1212893B/it active
- 1983-10-25 LU LU85059A patent/LU85059A1/fr unknown
- 1983-10-25 FR FR8316989A patent/FR2534921B1/fr not_active Expired
- 1983-10-25 GR GR72780A patent/GR79405B/el unknown
- 1983-10-25 KR KR1019830005035A patent/KR840006486A/ko not_active Withdrawn
- 1983-10-25 DE DE19833338753 patent/DE3338753A1/de not_active Ceased
- 1983-10-25 ZA ZA837921A patent/ZA837921B/xx unknown
- 1983-10-25 ES ES526738A patent/ES526738A0/es active Granted
- 1983-10-25 JP JP58199871A patent/JPS5998086A/ja active Pending
- 1983-10-25 CH CH5771/83A patent/CH661046A5/fr not_active IP Right Cessation
- 1983-10-25 AU AU20552/83A patent/AU2055283A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| FI833887A7 (fi) | 1984-04-26 |
| FR2534921A1 (fr) | 1984-04-27 |
| SE8305866D0 (sv) | 1983-10-25 |
| IT1212893B (it) | 1989-11-30 |
| JPS5998086A (ja) | 1984-06-06 |
| ES8504200A1 (es) | 1985-04-16 |
| BE898072A (fr) | 1984-04-25 |
| FR2534921B1 (fr) | 1987-01-16 |
| GB2129795B (en) | 1986-02-12 |
| IL70034A0 (en) | 1984-01-31 |
| LU85059A1 (fr) | 1985-06-19 |
| GR79405B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-10-22 |
| KR840006486A (ko) | 1984-11-30 |
| ES526738A0 (es) | 1985-04-16 |
| ZA837921B (en) | 1985-04-24 |
| NL8303673A (nl) | 1984-05-16 |
| SE8305866L (sv) | 1984-04-26 |
| AU2055283A (en) | 1984-05-03 |
| IT8349214A0 (it) | 1983-10-25 |
| FI833887A0 (fi) | 1983-10-25 |
| GB2129795A (en) | 1984-05-23 |
| GB8328468D0 (en) | 1983-11-23 |
| US4496579A (en) | 1985-01-29 |
| DE3338753A1 (de) | 1984-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |