DK162521B - Quinoxalinyloxyphenylderivater til anvendelse som mellemprodukter til fremstilling af herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater - Google Patents
Quinoxalinyloxyphenylderivater til anvendelse som mellemprodukter til fremstilling af herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater Download PDFInfo
- Publication number
- DK162521B DK162521B DK168589A DK168589A DK162521B DK 162521 B DK162521 B DK 162521B DK 168589 A DK168589 A DK 168589A DK 168589 A DK168589 A DK 168589A DK 162521 B DK162521 B DK 162521B
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- Denmark
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
- Quinoline Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
i
DK 162521 B
Den foreliggende opfindelse angår hidtil ukendte quinoxalinyl-oxyphenylderivater med den i kravet angivne almene formel VIII til anvendelse som mellemprodukter til fremstilling af herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater.
5 Ans.nr. 3068/80 angår hidtil ukendte herbicide quinoxalinyl-oxyphenoxyalkancarboxylsyrederivater med formlen t (°’* o
Byy^ f --Y--4 — X-C-(CH0) -w (*)
Mxv *2 I b v
E (0)1 V
eller et salt deraf, hvori A, B, D, E, J, D og V uafhængigt af hinanden er valgt af gruppen bestående af hydrogen, halogen, nitro, cyano, amino, C^-C^-alkylamino, di(C^-Cg-alkyl)-1° amino, C^-Cg-alkyl, C^-Cg-halogenalkyl, C2-Cg-alkenyl, C^-Cg-alkoxy, carboxy, (C^-Cg-alkoxy)carbonyl, carbamoyl, N- (Cj^-Cg-alkyl)carbamoyl, N,N-di (C^-Cg-alkyl)carbamoyl, R^· er valgt af gruppen bestående af hydrogen, C^-Cg-alkyl, 2 R er valgt af gruppen bestående af hydrogen, C^-Cg-alkyl,
N
15 W er valgt af gruppen bestående af -C-G, hvor G er valgt af gruppen bestående af C^-C^-alkoxy, C2-C10-alkenyloxy, Cg-C^-cykloalkoxy, Cg-C^-cykloalkoxy substitueret med en eller to C^-C^-alkylgrupper, phenoxy, phenylthlo, benzyloxy, benzylthio, gruppen C^-C^-alkoxy substitueret med en sub-20 stituent valgt af gruppen bestående af C^-Cg-alkoxy, amino, ammonium, N-(C^-Cg-alkyl)amino, N,N-di(C^-Cg-alkyl)amino og Ν,Ν,Ν-tri(C, -Cc-alkyl)ammonium, gruppen OM, hvor M er kat- 10 4 5 ionen af en uorganisk eller organisk base, gruppen -NR R ,
DK 162521 B
2 4 5 hvor R og R er valgt uafhængigt af hinanden af gruppen 4 5 bestående af hydrogen, C--C,-alkyl, eller R og R tilsammen β 6 6
danner en heterocyklisk ring, og gruppen -0-N=R , hvor R
er en C^-C^Q-alkylidengruppe, 5 X og Y er valgt uafhængigt af hinanden blandt oxygen og svovl, k og 1 er valgt uafhængigt af hinanden blandt 0 og 1, og n er 0, 1 eller 2.
Disse forbindelser adskiller sig fra kendte beslægtede for-10 bindeiser med herbicid virkning. For eksempel beskriver EP-ansøgning nr. 2800 phenoxypropionsyrederivater som herbicider, og DE nr. 2.640.730 beskriver heterocykliske phenylethere som herbicider. Disse sidstnævnte har imidlertid ringere herbicid virkning end forbindelserne ifølge 15 ans.nr. 3068/80. Endvidere beskriver DE nr. 2.640.730 heterocykliske phenylethere med herbicid virkning. Disse kendte forbindelser adskiller sig fra forbindelserne ifølge ans.nr. 3068/80 ved at have en 5-leddet ringstruktur, der giver forbindelserne helt andre fysiske og kemiske egenska-20 ber end quinoxalinylradikalet, således at man på denne baggrund ikke kan sige noget om egenskaberne af forbindelserne ifølge ans.nr. 3068/80.
Forbindelserne ifølge opfindelsen kan fremstilles som vist i nedenstående reaktionsskema ved kondensation af det ønske-25 de quinoxalinderivat med formlen V, hvori L er en bortgående gruppe (f.eks. alkylsulfonyl, chlor, brom eller jod), med den ønskede forbindelse med formlen VII.
DK 162521 B
3 A (0)k i ^ υ I — L hx— ---q-y .-VS? ^ (V) (VII) f (?’k ? r^X.
OLx x x>t~Q
C i: (i), J v (VIII)
Forbindelserne ifølge opfindelsen kan så anvendes som mellemprodukter til fremstilling af de herbicide forbindelser ifølge ans.nr. 3068/80 ved først eventuelt at blive dealky-leret til dannelse af forbindelser ifølge opfindelsen, hvori 5 Q er hydroxy eller mercapto, og derefter kondensation med en forbindelse med formlen R1
Hal - C - (CH_) - W.
i o 2 n R^
DK 162521 B
4
De ovennævnte kondensationsreaktioner udføres fortrinsvis i nærværelse af et alkalisk materiale og fortrinsvis i nærværelse af et opløsningsmiddel. Egnede alkaliske materialer indbefatter alkalimetal- og jordalkalimetalhydroxider og -carbo-5 nater såsom natriumhydroxid, kaliumhydroxid, natriumcarbonat og kaliumcarbonat. Egnede opløsningsmidler indbefatter ketoner som f.eks. acetone, methylethylketon og methylisobutyl-keton og dipolære, aprote opløsningsmidler som f.eks. dimethyl-formamid, dimethylacetamid, dimethylsulfoxid, N-methylpyrroli-10 don, hexamethylphosphoramid og sulfolan.
Reaktionsbetingelserne, som kræves for at bevirke kondensationsreaktionerne, varierer afhængende af karakteren af reaktionsdeltagerne og det anvendte opløsningsmiddel. I almindelighed lettes reaktionen ved tilførsel af varme, og i reglen 15 er en reaktionstemperatur i intervallet 40 - 150°C og en reaktionstid mellem 0,5 og 20 timer tilfredsstillende. Højere eller lavere reaktionstemperaturer og/eller kortere eller længere reaktionstider kan dog anvendes, hvis det ønskes.
Dealkyleringsreaktionen kan udføres under anvendelse af for-20 skellige reagenser, der er i og for sig kendt. For eksempel kan arylalkylethere spaltes under anvendelse af reagenser såsom pyridin-hydrochlorid, jodbrintesyre, brombrintesyre, natriumthioethoxid, dimethylformamid, acetyl-p-toluensulfonat, natrium- eller kaliumjodid i myresyre eller eddikesyre, 25 lithiumjodid i 2,4,6-collidin og bortribromid. Reaktionstider og reaktionsbetingelser varierer meget afhængende af det anvendte dealkyleringsmiddel og den ether, der skal spaltes.
De reaktionsbetingelser, som i almindelighed anvendes, når man benytter ovenstående "etherspaltningsreagenser", er velkendt 50 for fagfolk og kan tilpasses uden unødige forsøg for at bevirke etherspaltningsreaktionerne.
DK 162521 B
5 EKSEMPEL 1.
Fremstilling af forbindelse ifølge opfindelsen.
En opløsning af 4-mercaptophenol (10 mmol) i ethanol (10 ml) blev i én portion sat til en opløsning af natriumethoxid (10 mmol) i ethanol (30 ml). Efter om-5 røring af blandingen ved stuetemperatur i 15 minutter blev 10 mmol 2,6-dichlorquinoxalin tilsat, og blandingen blev omrørt i yderligere 30 minutter. Reaktionsblandingen blev fortyndet med 500 ml vand, og bundfaldet blev opsamlet ved filtrering og tørret til dannel-10 se af 4- (6-chlor-2-quinoxalinylthio) phenol, smeltepunkt 204°C.
EKSEMPEL A.
Fremstilling af herbicid forbindelse.
En blanding af thioether (1,0 g) fremstillet som be-15 skrevet i eks. 1 ovenfor, 0,6 g ethyl-2-brompropionat, 0,5 g kaliumcarbonat og 30 ml methylethylketon blev opvarmet under tilbagesvaling i 8 timer. Efter afkøling blev blandingen filtreret, og opløsningsmidlet blev fjernet ved destillation under reduceret tryk til dan-20 nelse af ethyl-2-[4-(6-chlor-2-quinoxalinylthio)phen= oxyjpropionat, smeltepunkt 110 - 115°C.
Den tillagte struktur blev bekræftet ved protonmagnetisk resonans-spektroskopi og masse-spektrometri.
Claims (1)
10 N,N-di (C^-Cg-alkyl)carbamoyl, X er valgt blandt oxygen og svovl, og k og 1 uafhængigt af hinanden er valgt blandt 0 og 1, og Q er valgt blandt hydroxy, mercapto, C^-Cg-alkoxy og C^-Cg-alkylthio.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPD961779 | 1979-07-17 | ||
AUPD961779 | 1979-07-17 | ||
AUPE309380 | 1980-04-11 | ||
AUPE309380 | 1980-04-11 |
Publications (4)
Publication Number | Publication Date |
---|---|
DK168589D0 DK168589D0 (da) | 1989-04-07 |
DK168589A DK168589A (da) | 1989-04-07 |
DK162521B true DK162521B (da) | 1991-11-11 |
DK162521C DK162521C (da) | 1992-03-30 |
Family
ID=25642316
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK306880A DK160426C (da) | 1979-07-17 | 1980-07-16 | Herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater, herbicidt middel og fremgangsmaade til alvorlig beskadigelse eller draebning af uoenskede planter eller til selektiv bekaempelse af vaeksten af enkimbladet ukrudt i tokimbladede afgroeder |
DK168489A DK168380B1 (da) | 1979-07-17 | 1989-04-07 | Halogensubstituerede quinoxalin-N-oxider til anvendelse som mellemprodukter til fremstilling af herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater |
DK168589A DK162521C (da) | 1979-07-17 | 1989-04-07 | Quinoxalinyloxyphenylderivater til anvendelse som mellemprodukter til fremstilling af herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK306880A DK160426C (da) | 1979-07-17 | 1980-07-16 | Herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater, herbicidt middel og fremgangsmaade til alvorlig beskadigelse eller draebning af uoenskede planter eller til selektiv bekaempelse af vaeksten af enkimbladet ukrudt i tokimbladede afgroeder |
DK168489A DK168380B1 (da) | 1979-07-17 | 1989-04-07 | Halogensubstituerede quinoxalin-N-oxider til anvendelse som mellemprodukter til fremstilling af herbicide quinoxalinyloxyphenoxyalkancarboxylsyrederivater |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP0023785B1 (da) |
JP (1) | JPH0613489B2 (da) |
AT (1) | ATE12495T1 (da) |
AU (1) | AU584309B2 (da) |
BR (1) | BR8004413A (da) |
CA (1) | CA1314549C (da) |
CS (1) | CS239908B2 (da) |
DE (1) | DE3070413D1 (da) |
DK (3) | DK160426C (da) |
ES (1) | ES8105985A1 (da) |
GR (1) | GR69684B (da) |
HU (1) | HU186299B (da) |
IE (1) | IE51142B1 (da) |
IL (1) | IL60506A (da) |
MY (1) | MY8700519A (da) |
NZ (1) | NZ194196A (da) |
PH (1) | PH16823A (da) |
PT (1) | PT71567A (da) |
SU (1) | SU1261564A3 (da) |
ZA (1) | ZA803928B (da) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
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US4803273A (en) * | 1979-07-17 | 1989-02-07 | Ici Australia Limited | 2-quinoxalinyloxy phenoxy compounds |
US4655819A (en) * | 1979-07-17 | 1987-04-07 | Ici Australia Limited | Quinoxalinyloxy phenoxy proprionic acid derivatives as selective herbicides |
JPS5651454A (en) * | 1979-10-01 | 1981-05-09 | Nissan Chem Ind Ltd | Hydroquinone derivative and its preparation |
CA1317299C (en) * | 1980-06-23 | 1993-05-04 | Maged Mohamed Fawzi | Quinoxalinyloxy ethers as selective weed control agents |
NZ197420A (en) * | 1980-07-01 | 1984-04-27 | Ici Australia Ltd | -(quinazolin-(2-or 4-)(oxy,ylthio or amino)phen(oxy or ylthio)alkanoic acid derivatives |
EP0048539B1 (en) * | 1980-07-01 | 1985-08-28 | Ici Australia Limited | Isoquinolyloxy(amino)phenoxyalkane carboxylic acid derivatives, process for their synthesis, herbicidal compositions containing them and their use as herbicides |
NZ197419A (en) * | 1980-07-01 | 1984-08-24 | Ici Australia Ltd | Omega-(cinnolin-(2 or 3-)yl(oxy,thio or amino)phen-(oxy or ylthio))alkanoic acid derivatives |
US5364831A (en) * | 1980-08-06 | 1994-11-15 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
DE3170423D1 (en) * | 1980-11-26 | 1985-06-13 | Hoffmann La Roche | Oxime esters, processes for their preparation, their use and compositions containing these esters |
NZ199342A (en) * | 1981-01-12 | 1985-08-16 | Ici Australia Ltd | Quinoxaline derivatives and herbicides |
US4391628A (en) * | 1981-02-16 | 1983-07-05 | Ciba-Geigy Corporation | 2-[4-(6-Haloquinoxalinyl-2-oxy)phenoxy]propionic acid esters |
JPS57163371A (en) * | 1981-04-01 | 1982-10-07 | Nissan Chem Ind Ltd | Preparation of hydroquinone derivative |
IL67463A (en) * | 1981-12-17 | 1985-12-31 | Du Pont | 2-alkoxyethoxyethyl 2-(4-(6-halo-2-quinoxy alinyloxy)phenoxy)propanoates and herbicidal compositions containing them |
US4528025A (en) * | 1982-10-25 | 1985-07-09 | Ppg Industries, Inc. | Herbicidally active quinoline or quinoxaline acetophenone oxime derivatives |
US4440930A (en) * | 1982-10-25 | 1984-04-03 | Ppg Industries, Inc. | Herbicidally active quinoline or quinoxaline acetophenone oxime derivatives |
US4464533A (en) * | 1982-11-08 | 1984-08-07 | Ppg Industries, Inc. | Herbicidally active quinoline or quinoxaline benzoate derivatives |
EP0113831A3 (de) * | 1982-12-17 | 1984-11-07 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Carbaminsäureester, Verfahren zu deren Herstellung und deren Verwendung |
ZA848416B (en) * | 1983-11-10 | 1986-06-25 | Dow Chemical Co | Fluorophenoxy compounds,herbicidal compositions and methods |
GB2171693A (en) * | 1985-03-01 | 1986-09-03 | Enrico Marotta | Quinoxaline derivatives useful for treatment and prophylaxis of swine dysentry and as animal growth promotants |
ZA862977B (en) * | 1985-05-02 | 1987-12-30 | Dow Chemical Co | Haloalkoxy anilide derivatives of 2-(4-heterocyclic oxyphenoxy)alkanoic acids and their use as herbicides |
JPS62190172A (ja) * | 1986-02-14 | 1987-08-20 | Teijin Ltd | フエノキシ脂肪族カルボン酸誘導体および除草剤 |
NZ224297A (en) * | 1987-04-20 | 1990-07-26 | Agro Kanesho Co Ltd | Phenoxypropionic acid ester derivatives and herbicidal compositions |
DE3883739T2 (de) * | 1988-01-06 | 1994-01-20 | Uniroyal Chem Co Inc | Herbizide Heterozyklisch-alkylen-Chinoxalinyloxyphenoxy Propansäureester. |
US5114464A (en) * | 1990-09-27 | 1992-05-19 | Uniroyal Chemical Company, Inc. | 4-quinoxalinyloxyphenoxyalkylinitrile herbicides |
WO1994013647A1 (en) * | 1992-12-15 | 1994-06-23 | The Du Pont Merck Pharmaceutical Company | (2-quinoxalinyloxy)phenoxypropanoic acids and related derivatives as anticancer agents |
JPH0712885U (ja) * | 1993-07-22 | 1995-03-03 | 田中産業株式会社 | 生籾収納袋における換気装置 |
AU721345B2 (en) * | 1996-06-03 | 2000-06-29 | Nissan Chemical Industries Ltd. | Processes for producing phenoxy propionic acid derivatives |
US6180632B1 (en) * | 1997-05-28 | 2001-01-30 | Aventis Pharmaceuticals Products Inc. | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
DE69812108T2 (de) | 1997-07-11 | 2003-10-09 | Nissan Chemical Industries, Ltd. | Pestizide zusammensetzung in form einer wässerigen suspension |
CN102718722B (zh) * | 2012-07-10 | 2016-02-17 | 南开大学 | 一种水油兼溶的新型芳氧苯氧羧酸酯类衍生物制备及应用研究 |
CN105712946A (zh) * | 2014-12-02 | 2016-06-29 | 沈阳中化农药化工研发有限公司 | 季铵盐类化合物及其应用 |
WO2024132001A1 (en) * | 2022-12-21 | 2024-06-27 | Charles University, Faculty Of Pharmacy In Hradec Kralove | Multitarget nuclear receptor ligands based on 2-(4-(quinolin-2-yloxy)phenoxy)propanoic acid and 2-(4-(quinoxalin-2-yloxy)phenoxy)propanoic acid for the treatment of metabolic and liver diseases |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2109005A1 (en) * | 1970-10-30 | 1972-05-26 | Ugine Kuhlmann | 4-(2-quinoxalyl)phenoxyacetic acids - diuretics and antiurics |
DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
CH650493A5 (en) * | 1977-12-24 | 1985-07-31 | Hoechst Ag | D-(+)-alpha-phenoxypropionic acid derivatives |
JPS6033389B2 (ja) * | 1979-02-22 | 1985-08-02 | 日産化学工業株式会社 | 複素環エ−テル系フェノシキ脂肪酸誘導体、その製造法および該誘導体を含有する除草剤 |
HU183173B (en) * | 1980-06-24 | 1984-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 6-hydrazono-pyrido-aracket-2,1-b-bracket closed-quinazolin-11-ones |
AU545426B2 (en) * | 1980-08-26 | 1985-07-11 | Ici Australia Limited | Process |
-
1980
- 1980-06-20 NZ NZ194196A patent/NZ194196A/xx unknown
- 1980-06-30 IE IE1374/80A patent/IE51142B1/en not_active IP Right Cessation
- 1980-06-30 ZA ZA00803928A patent/ZA803928B/xx unknown
- 1980-07-04 GR GR62372A patent/GR69684B/el unknown
- 1980-07-06 IL IL60506A patent/IL60506A/xx unknown
- 1980-07-11 CA CA000356027A patent/CA1314549C/en not_active Expired - Fee Related
- 1980-07-15 HU HU801762A patent/HU186299B/hu unknown
- 1980-07-16 DK DK306880A patent/DK160426C/da not_active IP Right Cessation
- 1980-07-16 CS CS805044A patent/CS239908B2/cs unknown
- 1980-07-16 PH PH24301A patent/PH16823A/en unknown
- 1980-07-16 SU SU2951003A patent/SU1261564A3/ru active
- 1980-07-16 ES ES493431A patent/ES8105985A1/es not_active Expired
- 1980-07-16 BR BR8004413A patent/BR8004413A/pt not_active IP Right Cessation
- 1980-07-17 PT PT71567A patent/PT71567A/pt unknown
- 1980-07-17 AT AT80302411T patent/ATE12495T1/de not_active IP Right Cessation
- 1980-07-17 DE DE8080302411T patent/DE3070413D1/de not_active Expired
- 1980-07-17 JP JP55096960A patent/JPH0613489B2/ja not_active Expired - Lifetime
- 1980-07-17 EP EP80302411A patent/EP0023785B1/en not_active Expired
-
1984
- 1984-08-31 AU AU32647/84A patent/AU584309B2/en not_active Expired
-
1987
- 1987-12-30 MY MY519/87A patent/MY8700519A/xx unknown
-
1989
- 1989-04-07 DK DK168489A patent/DK168380B1/da not_active IP Right Cessation
- 1989-04-07 DK DK168589A patent/DK162521C/da not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
PH16823A (en) | 1984-03-06 |
JPS5639077A (en) | 1981-04-14 |
PT71567A (en) | 1980-08-01 |
AU584309B2 (en) | 1989-05-25 |
DK168589D0 (da) | 1989-04-07 |
DK160426B (da) | 1991-03-11 |
DK168380B1 (da) | 1994-03-21 |
ZA803928B (en) | 1981-06-24 |
BR8004413A (pt) | 1981-01-27 |
IE801374L (en) | 1981-01-17 |
JPH0613489B2 (ja) | 1994-02-23 |
HU186299B (en) | 1985-07-29 |
EP0023785A2 (en) | 1981-02-11 |
ATE12495T1 (de) | 1985-04-15 |
IL60506A (en) | 1986-12-31 |
MY8700519A (en) | 1987-12-31 |
DK306880A (da) | 1981-01-18 |
EP0023785A3 (en) | 1981-04-29 |
AU3264784A (en) | 1984-12-20 |
DK168589A (da) | 1989-04-07 |
IL60506A0 (en) | 1980-09-16 |
SU1261564A3 (ru) | 1986-09-30 |
EP0023785B1 (en) | 1985-04-03 |
CS239908B2 (en) | 1986-01-16 |
DK162521C (da) | 1992-03-30 |
GR69684B (da) | 1982-07-08 |
CA1314549C (en) | 1993-03-16 |
NZ194196A (en) | 1983-07-15 |
DK168489A (da) | 1989-04-07 |
IE51142B1 (en) | 1986-10-15 |
DE3070413D1 (en) | 1985-05-09 |
ES493431A0 (es) | 1981-07-01 |
ES8105985A1 (es) | 1981-07-01 |
DK160426C (da) | 1991-08-19 |
DK168489D0 (da) | 1989-04-07 |
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