NO823213L - Fremgangsmaate for fremstilling av antranilsyreestere - Google Patents
Fremgangsmaate for fremstilling av antranilsyreestereInfo
- Publication number
- NO823213L NO823213L NO823213A NO823213A NO823213L NO 823213 L NO823213 L NO 823213L NO 823213 A NO823213 A NO 823213A NO 823213 A NO823213 A NO 823213A NO 823213 L NO823213 L NO 823213L
- Authority
- NO
- Norway
- Prior art keywords
- anthranilic acid
- quinolyl
- acid esters
- antranic
- procedure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title description 2
- 239000002253 acid Substances 0.000 title 1
- -1 2-oxo-3-oxolanyl Chemical group 0.000 claims description 8
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LFJJGHGXHXXDFT-UHFFFAOYSA-N 3-bromooxolan-2-one Chemical compound BrC1CCOC1=O LFJJGHGXHXXDFT-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- QBYPVSPDWKEXRG-UHFFFAOYSA-N 2-[[7-(trifluoromethyl)quinolin-4-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(C(F)(F)F)=CC=C12 QBYPVSPDWKEXRG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- OPDLOBUOCJOSPW-UHFFFAOYSA-M sodium;2-[[7-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1NC1=CC=NC2=CC(C(F)(F)F)=CC=C12 OPDLOBUOCJOSPW-UHFFFAOYSA-M 0.000 description 2
- HTKGKUISLUERQX-UHFFFAOYSA-N 2-[(7-chloroquinolin-4-yl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 HTKGKUISLUERQX-UHFFFAOYSA-N 0.000 description 1
- RGUIKQRAZCQMBM-UHFFFAOYSA-N 2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 RGUIKQRAZCQMBM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N gamma-butyrolactone Natural products O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LENZMLNHBQIMIB-UHFFFAOYSA-M sodium;2-[(7-chloroquinolin-4-yl)amino]benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 LENZMLNHBQIMIB-UHFFFAOYSA-M 0.000 description 1
- LDSANFGHCWNGRP-UHFFFAOYSA-M sodium;2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 LDSANFGHCWNGRP-UHFFFAOYSA-M 0.000 description 1
- HCKKSLZDSNNSTL-UHFFFAOYSA-M sodium;2-aminobenzoate Chemical compound [Na+].NC1=CC=CC=C1C([O-])=O HCKKSLZDSNNSTL-UHFFFAOYSA-M 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Quinoline Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Foreliggende oppfinnelse . vedrører en fremgangsmåte for fremstilling av antranilsyreestere med den generelle formel I
hvori n er 0,1 eller 2,
den ene av og R2representerer et kloratom eller en trifluormetyl-gruppe og den- annen representerer et hydrogenatom, og R representerer en 2-okso-3-oksolanyl - eller 2-okso-3-oksazolidinyl-gruppe, og det særegne ved fremgangs-måten i henhold til oppfinnelsen er at et salt av en N-(7- eller 8-substituert-4- kinolyl-.antranilsyre med den generelle formel II
hvori og R2har den ovennevnte betydning og X representerer et alkalimetall, reageres med et halogenderivat med den generelle form III
hvori n og R har den ovennevnte betydning.
Disse trekk ved oppfinnelsen fremgår av patentkravet.
Forbindelsene fremstilt i samsvar med oppfinnelsen er blitt funnet og fremviser gode analgetiske og antiinflammatoriske egenskaper.
Det N-(7- eller 8-substituerte-4- kinolyl-antranilsyresalt er foretrukket natriumsaltet (II, X = Na) mens halogenet i formel (III) vanligvis er klor eller brom.
Kondenseringen gjennomføres foretrukket i nærvær av et inert organiske løsningsmiddel som f.eks. dimetylformamid. Reaksjonskomponentene anvendes vanligvis i ekvimolare for-hold og temperaturen er fra 30-150°C.
Forbindelsene kan kombineres i farmasøytiske preparater. Sammen med farmasøytisk tålbare fortynningsmidlér eller bærere.
De aktive forbindelser fremviser gode analgetiske og antiinflammatoriske egenskaper med liten giftighet. Verdiene for LD,-q , bestemt i mus både i.p<p>g per os, er større enn henholdsvis 1000 og 3000 mg/kg. Dette gjelder for alle de testede forbindelser.
De analgetiske virkninger (ED^Q) bestemt i mus med smerte-testen i henhold (Sigmund et al., Proe. Soc. Exp.- Biol. Med. 95, 729, 1957); ble funnet å være mellom 6 og 18 mg/kg. ED,, ^-verdiene for den antiinf lammatoriske aktivitet ble
funnet å være mellom 20 og 30 mg/kg.
De følgende eksempler illustrerer oppfinnelsen.
EKSEMPEL 1
En blanding bestående av 6,4 g N-(7-klor-4- k inolyl) antranilsyre-natriumsalt og 3,28 g 3-brom-oksolan-2-on i 40 ml dimetylformamid ble oppvarmet under omrøring ved 40 til 45°C i 5 timer. Ved avsluttet reaksjon ble den således oppnådde oppløsnings filtrert og helt ut i 250 ml vann. Det uthelte faststoff ble samlet på et filter og behandlet med omtrent 100 ml kloroform. Hele.blandingen ble filtrert på nytt og ved tilsetning av petroleter ble N-(7-klor-4- kinolyl-antranilsyre- T -butyrolactonesteren oppnådd. Produktet ble isolert og krystallisert fra isopropanol i utbytte 4 g med Smp 155-157°C.
EKSEMPEL 2
En blanding bestående av 12,8 g N-(7-klor-4- kinolyl)-antranilsyre-natriumsalt, 6,64 g 90% 3- (jS -kloretyl-oksa-zolidin-2-on og 80 ml dimetylformamid ble oppvarmet under omrøring ved 120°C i 5 timer. Ved avsluttet reaksjon ble blandingen avkjølt, filtrert og løsningsmidlet av-drevet i vakuum. Til resten ble tilsatt 80 ml eter og det således oppnådde faststoff ble samlet på filteret og renset ved kromatografering på en silikagel-kolonne under anvendelse av etylacetat og elueringsmiddel. Det ønskede produkt ble krystallisert fra isopropanol til å gi 11, 2 g N-(7-klor-4- kinolyl)-antranilsyre J3 - (2-okso-3-oksazolidinyl(-etylester som smeltet ved 122-124°C.
EKSEMPEL 3
En blanding bestående av 10,62 g N-(8-trifluormetyl-4-.kinolyl)-antranilsyre-natriumsalt, 4,98 g 90% 3-(J9 — kloretyl)-oksazolidin-2-on og 60 ml dimetylformamid ble oppvarmet under omrøring ved 120°C i 5 timer. Ved av sluttet reaksjon ble blandingen avkjølt, filtrert og helt ut i 300 ml vann. Råproduktet ble ektrahert med etylacetat, løsningsmidlet ble avdampet, og resten krystallisert fra etanol til å gi 6 g N-(8-trifluormetyl-4- kinolyl)-antranilsyre $) - (2-okso-3-oksazolidinyl) -retylester som smeltet ved 158-160°C.
EKSEMPEL 4
En blanding bestående av 10,62 g N-(8-trifluormetyl-4-kinolyl)-antranilsyre-natriumsalt og 4,92 3-brom-oksølan-2- on i 60 ml dimetylformamid ble oppvarmet under omrøring ved 80°c i 5 timer. Ved avsluttet reaksjon ble den således oppnådde oppløsning avkjølt, filtrert og helt ut i 300 ml vann. Det oppnådde rå faststoff ble estrahert med etylacetat. Løsningsmiddel ble avdestillert og resten krystallisert til å gi 7 g N-(8-trifluormetyl-4- kiholyl)-antranilsyre- y -butyrolactonester med smeltepunkt 168-169°C.
EKSEMPEL 5
En blanding omfattende 10,62 g N-(7-trifluormetyl-4-kinolyl)-antranilsyre-natriumsalt, 4,98 g 90%
3- (J3 -kloretyl)-oksazolidin-2-on og 60 ml dimetylformamid ble oppvarmet under omrøring ved 120°C i 5 timer. Ved avsluttet reaksjon ble blandingen avkjølet, uoppløselig natriumklorid ble frafiltrert og løsningsmidlet ble avdampet under vakuum. Resten ble behandlet med 200 ml vann og faststoffet samlet ved filtrering, krystallisert fra metyldiklorid/pretroleter. 8,7 g N- (-7-tri£luormetyl-4-kinolyl)-antranilsyre B -(2^okso-3-oksazolidinyl)-etyl-ester som smeltet ved 124-125°c ble oppnådd.
EKSEMPEL 6
En blanding omfattende 10,62:g N-(7-trifluormetyl-4-kinolyl)-antranilsyre-natriumsalt, 3,24 ml 3-brom-oksolan-2-on og 60 ml dimetylformamid ble oppvarmet under om-
røring ved 80°c i 5 timer. Ved avsluttet reaksjon blé
blandingen avkjølt, uoppløselig natriumbromid ble fr.a-filtrert og løsningsmidlet ble avdampet under vakuum.
Resten ble behandlet med 200 ml vann, faststoffet ble samlet og krystallisert fra etanol til å gi 7,7 g N-(7-trifluormetyl-4-quinolyl)-antranilsyre Y~ butyrolakton-ester som smeltet ved 183-184°c.
Claims (1)
- Fremgangsmåte for fremstilling av antranilsyreestere med den generelle formel.Ihvori n er 0, 1 eller 2, er av eller R2representerer et kloratom eller en trifluormetyl-gruppe og den annen representerer et hydrogenatom, og R representerer en 2-okso-^3-oksolanyl eller 2-okso-3-oksazolidinyl-gruppe,karakterisert vedat et salt av en N-(7- eller 8-substituert-4- kinolyl)-antranilsyre med den generelle formel IIhvori og R2nar den ovennevnte betydning og X representerer et alkalimefcall, reageres med et halogenderivat med den generelle formel IIIhvori n og R har den ovennevnte betydning.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8129473 | 1981-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO823213L true NO823213L (no) | 1983-04-05 |
Family
ID=10524829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO823213A NO823213L (no) | 1981-09-30 | 1982-09-23 | Fremgangsmaate for fremstilling av antranilsyreestere |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4507308A (no) |
| EP (1) | EP0076600A1 (no) |
| JP (1) | JPS5959664A (no) |
| AU (1) | AU549754B2 (no) |
| CA (1) | CA1193259A (no) |
| DE (1) | DE3236096A1 (no) |
| DK (1) | DK408782A (no) |
| ES (1) | ES516059A0 (no) |
| FI (1) | FI823294L (no) |
| GB (1) | GB2106516B (no) |
| GR (1) | GR77656B (no) |
| IL (1) | IL66752A0 (no) |
| IT (1) | IT1157325B (no) |
| NL (1) | NL8203785A (no) |
| NO (1) | NO823213L (no) |
| NZ (1) | NZ201938A (no) |
| PT (1) | PT75595B (no) |
| SE (1) | SE8205523L (no) |
| SG (1) | SG59485G (no) |
| YU (1) | YU192782A (no) |
| ZA (1) | ZA826291B (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1193598A (en) * | 1982-05-06 | 1985-09-17 | Rafael Foguet | 2-amino-benzoic acid derivatives and processes for their production |
| FR2873695A1 (fr) * | 2004-07-30 | 2006-02-03 | Palumed Sa | Molecules hybrides qa ou q est une aminoquinoleine et a est un antibiotique ou un inhibiteur de resistance), leur synthese et leurs utilisations en tant qu'agent antibacterien |
| BRPI0514381A (pt) * | 2004-07-30 | 2008-06-10 | Palumed Sa | compostos hìbridos de aminoquinolina-antibiótico, composições farmacêuticas, método de preparação e uso destes |
| FR2874922A1 (fr) * | 2004-07-30 | 2006-03-10 | Palumed Sa | Molecules hybrides qa ou q est une aminoquinoleine et a est un residu antibiotique, leur synthese et leurs utilisations en tant qu'agent antibacterien |
| IT201600132467A1 (it) | 2017-01-04 | 2018-07-04 | H2Boat | Turboespansore a strato limite e macchina a ciclo inverso provvista di tale turboespansore |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA731646A (en) * | 1962-05-08 | 1966-04-05 | Roussel-Uclaf | 4-(2'(.beta.-MORPHOLYLETHOXYCARBONYL) PHENYLAMINE) 7-CHLORO QUINOLEINE ET SES SELS, AINSI QUE LEUR PROCEDE DE PREPARATION |
| FR6103M (no) * | 1967-02-22 | 1968-06-10 | ||
| FR6195M (no) * | 1967-04-11 | 1968-07-22 | ||
| FR7870M (no) * | 1968-11-08 | 1970-04-27 | ||
| US3637710A (en) * | 1969-05-26 | 1972-01-25 | Geigy Chem Corp | 4-(phenylimino)-1 4-dihydroquinoline derivatives |
| US3764603A (en) * | 1972-04-13 | 1973-10-09 | Abbott Lab | 2-hydroxy-2-carboxyethyl-n-(7- or 8-chloro-4-quinolinyl)anthranilate |
| GB1573186A (en) * | 1977-09-14 | 1980-08-20 | Wyeth John & Brother Ltd | 4-aminoquinoline derivatives |
-
1982
- 1982-08-26 YU YU01927/82A patent/YU192782A/xx unknown
- 1982-08-27 ZA ZA826291A patent/ZA826291B/xx unknown
- 1982-09-09 IL IL66752A patent/IL66752A0/xx unknown
- 1982-09-14 DK DK408782A patent/DK408782A/da not_active Application Discontinuation
- 1982-09-16 NZ NZ201938A patent/NZ201938A/en unknown
- 1982-09-22 PT PT75595A patent/PT75595B/pt unknown
- 1982-09-23 GB GB08227203A patent/GB2106516B/en not_active Expired
- 1982-09-23 NO NO823213A patent/NO823213L/no unknown
- 1982-09-23 EP EP82305009A patent/EP0076600A1/en not_active Withdrawn
- 1982-09-24 FI FI823294A patent/FI823294L/fi not_active Application Discontinuation
- 1982-09-24 JP JP57167465A patent/JPS5959664A/ja active Pending
- 1982-09-28 US US06/426,229 patent/US4507308A/en not_active Expired - Fee Related
- 1982-09-28 GR GR69382A patent/GR77656B/el unknown
- 1982-09-28 SE SE8205523A patent/SE8205523L/xx not_active Application Discontinuation
- 1982-09-29 NL NL8203785A patent/NL8203785A/nl not_active Application Discontinuation
- 1982-09-29 ES ES516059A patent/ES516059A0/es active Granted
- 1982-09-29 DE DE19823236096 patent/DE3236096A1/de not_active Withdrawn
- 1982-09-29 CA CA000412422A patent/CA1193259A/en not_active Expired
- 1982-09-29 IT IT23493/82A patent/IT1157325B/it active
- 1982-09-29 AU AU88839/82A patent/AU549754B2/en not_active Ceased
-
1985
- 1985-08-05 SG SG594/85A patent/SG59485G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2106516A (en) | 1983-04-13 |
| CA1193259A (en) | 1985-09-10 |
| PT75595A (fr) | 1982-10-01 |
| FI823294A0 (fi) | 1982-09-24 |
| GB2106516B (en) | 1985-03-27 |
| ZA826291B (en) | 1983-07-27 |
| NL8203785A (nl) | 1983-04-18 |
| DE3236096A1 (de) | 1983-04-07 |
| FI823294L (fi) | 1983-03-31 |
| SE8205523L (sv) | 1983-03-31 |
| US4507308A (en) | 1985-03-26 |
| JPS5959664A (ja) | 1984-04-05 |
| YU192782A (en) | 1985-04-30 |
| IT1157325B (it) | 1987-02-11 |
| ES8308854A1 (es) | 1983-10-01 |
| DK408782A (da) | 1983-03-31 |
| SG59485G (en) | 1986-08-01 |
| IL66752A0 (en) | 1982-12-31 |
| GR77656B (no) | 1984-09-25 |
| EP0076600A1 (en) | 1983-04-13 |
| SE8205523D0 (sv) | 1982-09-28 |
| AU549754B2 (en) | 1986-02-13 |
| PT75595B (fr) | 1984-12-10 |
| NZ201938A (en) | 1985-04-30 |
| AU8883982A (en) | 1983-04-14 |
| ES516059A0 (es) | 1983-10-01 |
| IT8223493A0 (it) | 1982-09-29 |
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