NO150482B - INTERMEDIATES FOR THE PREPARATION OF THERAPEUTIC ACTIVE ANTHRAKINON DERIVATIVES - Google Patents
INTERMEDIATES FOR THE PREPARATION OF THERAPEUTIC ACTIVE ANTHRAKINON DERIVATIVES Download PDFInfo
- Publication number
- NO150482B NO150482B NO820290A NO820290A NO150482B NO 150482 B NO150482 B NO 150482B NO 820290 A NO820290 A NO 820290A NO 820290 A NO820290 A NO 820290A NO 150482 B NO150482 B NO 150482B
- Authority
- NO
- Norway
- Prior art keywords
- derivatives
- intermediates
- preparation
- anthrakinon
- therapeutic active
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229960001156 mitoxantrone Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QJQPINQAQJTYMH-UHFFFAOYSA-N 5,8,9,10-tetrahydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound O=C1CCC(=O)C2=C1C(O)=C1C(O)=CC=C(O)C1=C2O QJQPINQAQJTYMH-UHFFFAOYSA-N 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
- C08G59/623—Aminophenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (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)
- Pyridine Compounds (AREA)
Description
Denne oppfinnelse angår nye forbindelser som kan anvendes som mellomprodukter for fremstilling av terapeutisk aktive forbindelser med den følgende formel: This invention relates to new compounds that can be used as intermediates for the production of therapeutically active compounds with the following formula:
de tautomere former og de farmalcologisk godtagbare syreaddisjonssalter derav, hvor A-B er CH=CH eller CI^-CI^, og Z er hydrogen eller hydroksy. the tautomeric forms and the pharmacologically acceptable acid addition salts thereof, where A-B is CH=CH or CI^-CI^, and Z is hydrogen or hydroxy.
Forbindelsene ifølge oppfinnelsen har den følgende The compounds according to the invention have the following
formel: formula:
de tautomere former og de farmakologisk godtagbare syre-addis jonssalter derav, hvor A-B og Z er som ovenfor. Forbindelsene med formel I omdannes til forbindelsene med the tautomeric forms and the pharmacologically acceptable acid addition salts thereof, where A-B and Z are as above. The compounds of formula I are converted to the compounds with
formel II ved omsetning med vandig-etanolisk HC1 ved 40-80°C formula II by reaction with aqueous-ethanolic HCl at 40-80°C
i 1-6 timer. for 1-6 hours.
Typiske forbindelser ifølge oppfinnelsen er de følgende: 1,4-bis[2-(1,3-oksazolidin-l-yl)etylamino]-5,8-dihydroksy-antrakinon, leuko-base og tautomer derav; Typical compounds according to the invention are the following: 1,4-bis[2-(1,3-oxazolidin-1-yl)ethylamino]-5,8-dihydroxy-anthraquinone, leuco-base and tautomers thereof;
1,4-bis[2-(tetrahydro-1,3-oksazin-l-yl)etylamino]-5,8-dihydroksy-antrakinon, leuko-base og tautomer derav; 1,4-bis[2-(tetrahydro-1,3-oxazin-1-yl)ethylamino]-5,8-dihydroxyanthraquinone, leuco-base and tautomers thereof;
1,4-bis[2-(1,3-oksazolidin-2-on-l-yl)etylamino]-5,8-dihydroksy-antrakinon, leuko-base og tautomer derav; eller 1,4-bis[2-(tetrahydro-1,3-oksazin-2-on-l-yl)etylamino]-5,8-dihydroksy- 1,4-bis[2-(1,3-oxazolidin-2-on-1-yl)ethylamino]-5,8-dihydroxy-anthraquinone, leuco-base and tautomers thereof; or 1,4-bis[2-(tetrahydro-1,3-oxazin-2-on-1-yl)ethylamino]-5,8-dihydroxy-
antrakinon, leuko-basen og tautomeren derav; anthraquinone, the leuco-base and its tautomer;
og farmasøytisk godtagbare syreaddisjonssalter derav. and pharmaceutically acceptable acid addition salts thereof.
Det følgende eksemple illustrerer fremstilling av en forbindelse ifølge oppfinnelsen. The following example illustrates the preparation of a compound according to the invention.
Eksempel Example
1, 4- bis [ 2- ( 1, 3- oksazolidin- l- yl) etylamino]- 5, 8- dihydroksy-antrakinon 1,4-bis[2-(1,3-oxazolidin-1-yl)ethylamino]-5,8-dihydroxyanthraquinone
En blanding av 12,5 g 2-(2-aminoetylamino)-etanol, 9,7 g 37,1% formaldehyd og 150 ml benzen oppvarmes under tilbakeløps-kjøling under anvendelse av en Dean-Stark felle for å fjerne vann. Oppvarmning fortsettes inntil ikke mer vann kommer over og derefter i ytterligere en time. Blandingen inndampes derefter til en sirup inneholdende 2-(1,3-oksazolidin-1-yl)-etylamin. Til denne settes 40 ml avluftet N,N,N',N'-tetrametyl-etylendiamin og 10,97 g leuko-1,4,5,8-tetrahydroksyantrakinon. Denne blanding omrøres under nitrogen i et oljebad som holdes ved 50-55°C i 5 timer. Blandingen avkjøles i flere timer og filtreres. Det resulterende, faste, stoff suspenderes påny i 120 ml N,N,N<1>,N'-tetrametyletylendiamin og oppvarmes i et dampbad under tilbakeløpskjøling mens luft bobles gjennom i 12 timer. Blandingen avkjøles, og produktet oppsamles for å A mixture of 12.5 g of 2-(2-aminoethylamino)-ethanol, 9.7 g of 37.1% formaldehyde and 150 ml of benzene is heated under reflux using a Dean-Stark trap to remove water. Heating is continued until no more water comes over and then for another hour. The mixture is then evaporated to a syrup containing 2-(1,3-oxazolidin-1-yl)-ethylamine. To this is added 40 ml of deaerated N,N,N',N'-tetramethylethylenediamine and 10.97 g of leuco-1,4,5,8-tetrahydroxyanthraquinone. This mixture is stirred under nitrogen in an oil bath which is kept at 50-55°C for 5 hours. The mixture is cooled for several hours and filtered. The resulting solid is resuspended in 120 ml of N,N,N<1>,N'-tetramethylethylenediamine and heated on a steam bath under reflux while air is bubbled through for 12 hours. The mixture is cooled, and the product is collected to
gi 10 g blåsvart produkt, sm.p. 203-204°C. give 10 g of blue-black product, m.p. 203-204°C.
Claims (1)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82487277A | 1977-08-15 | 1977-08-15 | |
| US87317478A | 1978-01-30 | 1978-01-30 | |
| US87304178A | 1978-01-30 | 1978-01-30 | |
| US87304078A | 1978-01-30 | 1978-01-30 | |
| US05/903,292 US4138415A (en) | 1978-05-05 | 1978-05-05 | 1,4-Bis(aminoalkylamino)-anthraquinones and leuco derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO820290L NO820290L (en) | 1979-02-16 |
| NO150482B true NO150482B (en) | 1984-07-16 |
| NO150482C NO150482C (en) | 1984-10-24 |
Family
ID=27542240
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782756A NO148777C (en) | 1977-08-15 | 1978-08-14 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE ANTHRAKINON DERIVATIVES |
| NO820290A NO150482C (en) | 1977-08-15 | 1982-02-01 | INTERMEDIATES FOR THE PREPARATION OF THERAPEUTIC ACTIVE ANTHRAKINON DERIVATIVES |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782756A NO148777C (en) | 1977-08-15 | 1978-08-14 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE ANTHRAKINON DERIVATIVES |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS6463556A (en) |
| AR (1) | AR225884A1 (en) |
| AT (1) | AT359484B (en) |
| AU (1) | AU527103B2 (en) |
| BE (1) | BE869688A (en) |
| CH (1) | CH644840A5 (en) |
| DD (1) | DD139256A5 (en) |
| DE (1) | DE2835661A1 (en) |
| DK (1) | DK158836C (en) |
| FI (1) | FI70882C (en) |
| FR (1) | FR2400504A1 (en) |
| GB (1) | GB2004293B (en) |
| GR (1) | GR74415B (en) |
| IE (1) | IE47253B1 (en) |
| IL (1) | IL55218A (en) |
| IT (1) | IT1107773B (en) |
| NL (1) | NL188981C (en) |
| NO (2) | NO148777C (en) |
| NZ (1) | NZ187989A (en) |
| PL (1) | PL122586B1 (en) |
| PT (1) | PT68420A (en) |
| SE (1) | SE445996B (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275009A (en) * | 1979-05-29 | 1981-06-23 | American Cyanamid Company | 1-(Aminoalkylamino)-5,8-dihydroxy-4-substituted-anthraquinones |
| US4275010A (en) * | 1979-10-24 | 1981-06-23 | American Cyanamid Company | 5,8-Dihydroxy-1,4-bis(guanidinylamino)anthraquinones |
| US4296030A (en) * | 1980-04-09 | 1981-10-20 | American Cyanamid Company | Metal chelates of 1,4-bis(substituted-amino-5,8-dihydroxy-anthraquinones |
| US4278605A (en) * | 1980-06-30 | 1981-07-14 | American Cyanamid Company | Heteroalkylenebisanthraquinones |
| EP0052853A1 (en) * | 1980-11-24 | 1982-06-02 | Hoechst Aktiengesellschaft | Bis-aminomethyl-anthraquinone derivatives, process for their manufacture, compositions containing them and their use |
| EP0083683A1 (en) * | 1981-10-26 | 1983-07-20 | American Cyanamid Company | Method of preparing 1,4-bis(substituted-amino)-5,8-dihydroxyanthraquinones and pharmaceutical compositions containing them |
| ATE48942T1 (en) * | 1984-02-27 | 1990-01-15 | American Cyanamid Co | USE OF 1,4 BI-SUBSTITUTED ANTHRACHINONES FOR THE MANUFACTURE OF IMMUNOSUPPRESSIVES. |
| EP0182135A3 (en) * | 1984-11-19 | 1987-08-05 | American Cyanamid Company | Novel bis-(substituted amino) anthraquinones |
| US5436243A (en) * | 1993-11-17 | 1995-07-25 | Research Triangle Institute Duke University | Aminoanthraquinone derivatives to combat multidrug resistance |
| GB9815910D0 (en) * | 1998-07-21 | 1998-09-23 | Btg Int Ltd | Synthetic method |
| ATE423767T1 (en) * | 2003-12-23 | 2009-03-15 | Somanta Ltd | ANTHRAQUINONE DERIVATIVES AS AN AGAINST CANCER |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| AU2009329872B2 (en) | 2008-12-23 | 2016-07-07 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| AR074897A1 (en) | 2008-12-23 | 2011-02-23 | Pharmasset Inc | NUCLEOSID PHOSPHORAMIDATES |
| KR20110098849A (en) | 2008-12-23 | 2011-09-01 | 파마셋 인코포레이티드 | Nucleoside analogs |
| TW201139457A (en) | 2010-03-31 | 2011-11-16 | Pharmasset Inc | Stereoselective synthesis of phosphorus containing actives |
| DE102012203981A1 (en) * | 2012-03-14 | 2013-09-19 | Henkel Ag & Co. Kgaa | Agent for dyeing and / or delustering keratin-containing fibers containing novel 1,4-diaminoanthraquinone dyes |
| GB201214169D0 (en) | 2012-08-08 | 2012-09-19 | Biostatus Ltd | New compounds and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1422016A (en) * | 1962-10-29 | 1965-12-24 | Oreal | New anthraquinone dyes and their application to hair dye |
| GB1157506A (en) * | 1965-09-10 | 1969-07-09 | Ilford Ltd | Anthraquinone Dye Colour Couplers and their use in Colour Photographic Materials |
| US3700398A (en) * | 1970-07-27 | 1972-10-24 | Du Pont | Process for dyeing acid-modified nylon fibers |
| US3646072A (en) * | 1970-07-27 | 1972-02-29 | Du Pont | Turquoise biscationic anthraquinone dyes |
| US4051155A (en) * | 1975-12-15 | 1977-09-27 | Allied Chemical Corporation | Anthraquinone dyes |
-
1978
- 1978-07-19 SE SE7807987A patent/SE445996B/en not_active IP Right Cessation
- 1978-07-26 IL IL55218A patent/IL55218A/en active IP Right Grant
- 1978-07-27 NZ NZ187989A patent/NZ187989A/en unknown
- 1978-08-03 AR AR273195A patent/AR225884A1/en active
- 1978-08-07 GR GR56957A patent/GR74415B/el unknown
- 1978-08-09 AU AU38776/78A patent/AU527103B2/en not_active Expired
- 1978-08-09 FR FR7823503A patent/FR2400504A1/en active Granted
- 1978-08-11 BE BE78189842A patent/BE869688A/en not_active IP Right Cessation
- 1978-08-11 IE IE1636/78A patent/IE47253B1/en not_active IP Right Cessation
- 1978-08-14 IT IT50730/78A patent/IT1107773B/en active
- 1978-08-14 NO NO782756A patent/NO148777C/en unknown
- 1978-08-14 AT AT590678A patent/AT359484B/en not_active IP Right Cessation
- 1978-08-14 DE DE19782835661 patent/DE2835661A1/en active Granted
- 1978-08-14 PT PT68420A patent/PT68420A/en unknown
- 1978-08-14 CH CH862778A patent/CH644840A5/en not_active IP Right Cessation
- 1978-08-14 DK DK358678A patent/DK158836C/en not_active IP Right Cessation
- 1978-08-15 FI FI782481A patent/FI70882C/en not_active IP Right Cessation
- 1978-08-15 GB GB7833365A patent/GB2004293B/en not_active Expired
- 1978-08-15 DD DD78207292A patent/DD139256A5/en unknown
- 1978-08-15 NL NLAANVRAGE7808475,A patent/NL188981C/en not_active IP Right Cessation
- 1978-08-15 PL PL1978209065A patent/PL122586B1/en unknown
-
1982
- 1982-02-01 NO NO820290A patent/NO150482C/en unknown
-
1987
- 1987-12-16 JP JP62316353A patent/JPS6463556A/en active Granted
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