NO824232L - Fremgangsmaate for fremstilling av acebutolol - Google Patents
Fremgangsmaate for fremstilling av acebutololInfo
- Publication number
- NO824232L NO824232L NO824232A NO824232A NO824232L NO 824232 L NO824232 L NO 824232L NO 824232 A NO824232 A NO 824232A NO 824232 A NO824232 A NO 824232A NO 824232 L NO824232 L NO 824232L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- dioxalanyl
- isopropylamino
- propanol
- butyramidophenoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 title description 10
- 229960002122 acebutolol Drugs 0.000 title description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- MFGKLROXINRXIU-UHFFFAOYSA-N n-[3-acetyl-4-(oxiran-2-ylmethoxy)phenyl]butanamide Chemical compound CC(=O)C1=CC(NC(=O)CCC)=CC=C1OCC1OC1 MFGKLROXINRXIU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229960002415 trichloroethylene Drugs 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- CFPKVTKDDGALCR-UHFFFAOYSA-N 4-(phenoxymethyl)-1,3,2-dioxathiolane 2-oxide Chemical compound O1S(=O)OCC1COC1=CC=CC=C1 CFPKVTKDDGALCR-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 229960003830 acebutolol hydrochloride Drugs 0.000 description 1
- KTUFKADDDORSSI-UHFFFAOYSA-N acebutolol hydrochloride Chemical compound Cl.CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 KTUFKADDDORSSI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FGWZEOPEZISTTR-UHFFFAOYSA-N n-(3-acetyl-4-hydroxyphenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(O)C(C(C)=O)=C1 FGWZEOPEZISTTR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Denne oppfinnelse angår en fremgangsmåte for fremstilling av acebutolol eller l-isopropylamino-3-(2-acetyl-4-butyramido-fenoksy)-2-propanol (I).
Acebutolol er et kjent terapeutisk middel.
Britisk patent 1,247.384 beskriver en fremgangsmåte for fremstilling av acebutolol hvor 3-(2-acetyl-4-butyramido-fenoksy)-1,2-propylenoksyd (II)
omsettes med isopropylamin.
Japansk publisert patentansøkning 57-2246 (referert i Chem. Abstr. 97: 5962) beskriver en fremgangsmåte for fremstilling av l-isopropylamino-3-(2-allylfenoksy)-, 1-isopropyl-amino-3-fenoksy- eller l-isopropylamino-3-(2-allyloksyfenoksy)-2-propanol, hvor det passende 4-fenoksymetyl-1,3,2-dioksatiolan-2-oksyd (III)
omsettes med isopropylamin.
Generelle metoder for fremstilling av l-isopropylamino-3-aryloksy-2-propanoler er beskrevet f.eks. i Kemisk Tidskrift, 1976, nr. 10, 48 og i Kemia-Kemi, 1978, nr. 5, 186.
Spesielle modifikasjoner for fremstilling av acebutolol er også beskrevet i de finske ålment tilgjengelige patent-ansøkninger 803226 og 803227,
Det er nu funnet at acebutolol kan fremstilles ved at 4-((2-(l-metyl-2,5-dioksalanyl)-4-butyramidofenoksy)metyl)- 1,3,2-dioksatiolan-2-oksyd (IV)
omsettes med isopropylamin, og den oppnådde l-isopropylamino-3-(2-(l-metyl-2,5-dioksalany1)-4-butyramidofenoksy)-2-propanol behandles med mineralsyre. Forbindelsen med formel IV er ny. Den kan fremstilles ved at 3-(2-(l-metyl-2,5-dioksalanyl)-4-butyramido-fenoksy)-1,2-propandiol (V)
omsettes med tionylklorid. Omsetningen utføres fortrinnsvis i et inert oppløsningsmiddel ved normal eller redusert temperatur i nærvær av et tertiært amin.
Forbindelsen med formel V er også ny. Den fremstilles fortrinnsvis ved ketalisering av 2-acetyl-4-butyramidofenol til 2-(l-metyl-2,5-dioksalanyl)-4-butyramidofenol og omsetning av denne med glycidol i nærvær av en basekatalysator.
Omsetningen av forbindelsen med formel IV med isopropylamin utføres ved oppvarmning av dem i et egnet organisk oppløsnings-middel, fortrinnsvis i acetonitril.
Behandling av mellomproduktet l-isopropylamino-3-(2-(l-metyl-2,5-dioksalanyl)-4-butyramidofenoksy)-2-propanol foretas fortrinnsvis i aceton og med saltsyre. Således oppnås lett acebutolol som hydrokloridsaltet søm er den ønskede form for farmasøytiske formål.
De uønskede bireaksjoner er hovedproblemene med den kjente metode ifølge britisk patent 1.247.384. Særlig når forbindelse II fremstilles fra den tilsvarende fenol og epiklorhydrin, reagerer fenolen også med sluttproduktet II. Omsetningen av forbindelse II med isopropylamin fører dessuten lett til den tilsvarende isomere 1-propanol. Det totale utbytte ved fremgangsmåten er forholdsvis lavt, og de nødvendige rensninger gjør fremgangsmåten enda mer uøkonomisk.
Fremgangsmåten ifølge publisert japansk patentansøkning 57-2246 er ikke uten videre anvendelig for fremstilling av acebutolol, fordi 4-((2-acetyl-4-butyramidofenoksy)metyl)-1,3,2-d.ioksatiolan-2-oksyd ikke kan oppnås ved de foreslåtte fremgangsmåter.
Utbyttet ved fremgangsmåten ifølge oppfinnelsen er høyt,
og bare ubetydelige mengder av uønskede biprodukter dannes. Dette gjør at fremgangsmåten også er egnet for industriell fremstilling.
Eksempel
a) 3-(2-(l-metyl-2,5-dioksalan-2-yl)-4-butyramidofenoksy)-1,2-propandiol (V)
En oppløsning av 4,5 g (0,06 mol) glycidol i 60 ml 1,1,2-trikloretylen settes langsomt under nitrogen til en kokende oppløsning av 13,3 g (0,05 mol) av 2-(l-metyl-2,5-dioksalanyl)-4-butyramidofenol og en katalytisk mengde natrium-metoksy i 60 ml 1,1,2-trikloretylen. Blandingen tilbakeløps-behandles under nitrogen i 24 timer. Oppløsningsmidlet avdampes i vakuum. 17,0 g (100%) av detønskede produkt oppnås: H<1->NMR (CDC13): 6 = 0,97 (3H t), 1,70 (2H sext), 1,72 (3H s), 2,30 (2H t), 3,50-4,20 (11H m), 6,90 (1H d), 7,50-7,72 (2H m), 9,10 (1H s).
b) 4-((2-(2-metyl-l,3-dioksalan-2-yl)-4-butyramidofenoksy)-metyl)-1,3,2-dioksatiolan-2-oksyd (IV)
En oppløsning av 4,4 ml tionylklorid i 6 ml diklormetan settes til en oppløsning av 17 g (0,06 mol) av forbindelse V og 6,1 g (0,06 mol) av. trietylamin i 60 ml diklormetan ved 0°C. Blandingen omrøres i 15 minutter ved 0-5°C, vaskes med 0,1N saltsyre og vann og tørres med Na2S04, Oppløsningen inndampes til tørrhet i vakuum. 20,7 g (93%) av det ønskede produkt oppnås: H<1->NMR: 0,97 (3H t), 1,70 (3H s), 1,75 (2H sext), 2,30 (2H t), 3,55-4,80 (8H m), 5,20 (1H qu), 6,80 (1H d), 7,40 - 7,65 (1H s).
c) l-isopropylamino-3-(2-acetyl-4-butyramidofenoksy)-2-propanol (I)
19,3 g (0,05 mol) av forbindelse IV og 30 ml isopropylamin i 100 ml acetonitril tilbakeløpsbehandles i 20 timer. Opp-løsningsmidlene fjernes under redusert trykk, og aceton settes til residuet. Blandingen filtreres, og 0,04 mol konsentrert saltsyre tilsettes, 16,4 g (88%) acebutolol-hydroklorid oppnås
(sirup. 141-143°C)
Claims (7)
1. Fremgangsmåte for fremstilling av l-isopropylamino-3-(2-acetyl-4-butyramidofenoksy)-2-propanol med formelen
eller salter derav,
karakterisert ved at 4-((2-(l-metyl-2,5-dioksalany1)-4-butyramidofenoksy)metyl)-1,3,2-dioksatiolan-2-oksyd med formelen
omsettes med isopropylamin, og derefter behandles den oppnådde l-isopropylamino-3-(2-(l-metyl-2,5-dioksalanyl)-4-butyramido-fenoksy)-2-propanol med mineralsyre, og eventuelt omdannes det oppnådde salt til den frie base.
2. Fremgangsmåte ifølge krav 1, karakterisert ved at omsetningen utføres i et organisk oppløsningsmiddel.
ri
3. Fremgangsmåte ifølge _kr$v 2 f/ karakterisert ved at |det som orgjanisk oppløsningsmiddel anvendesj acetonitril.
4/ Fremgangsmåte ifølge krav , 2', karakterisert ved at 4-( (2-(l-metyl-2,5-dioksalanyl)-4-butyramido-fenoksy)-mety1)-1,3,2-dioksatiolan-2-oksyd tilbakeløpsbehandles med isopropylamin i aceton i ca. 20 timer.
5. Fremgangsmåte ifølge et av kravene 1 til "4, karakterisert ved at det som mineralsyre anvendes saltsyre.
6 . Fremgangsmåte ifølge et av kravene 1 til 5^, karakterisert ved at behandlingen av l-isopropylamino-3-(2-(l-metyl-2,5-dioksalanyl)-4-butyramido-fenoksy)-2-propanol med mineralsyre foretas i aceton.
7. l-isopropylamino-3-(2-(l-metyl-2,5-dioksalanyl)-4-butyramidofenoksy)-2-propanol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI814053 | 1981-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO824232L true NO824232L (no) | 1983-06-20 |
Family
ID=8514961
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO824232A NO824232L (no) | 1981-12-17 | 1982-12-16 | Fremgangsmaate for fremstilling av acebutolol |
| NO824233A NO155619C (no) | 1981-12-17 | 1982-12-16 | Fremgangsmaate for fremstilling av metoprolol. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO824233A NO155619C (no) | 1981-12-17 | 1982-12-16 | Fremgangsmaate for fremstilling av metoprolol. |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS58159449A (no) |
| KR (1) | KR840002768A (no) |
| CA (1) | CA1198125A (no) |
| DK (2) | DK156567C (no) |
| HU (1) | HU186649B (no) |
| NO (2) | NO824232L (no) |
| SE (2) | SE452612B (no) |
| SU (1) | SU1170968A3 (no) |
| YU (2) | YU275882A (no) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56152461A (en) * | 1980-04-30 | 1981-11-26 | Ota Seiyaku Kk | Preparation of indole derivative |
-
1982
- 1982-12-06 KR KR1019820005450A patent/KR840002768A/ko unknown
- 1982-12-07 DK DK542082A patent/DK156567C/da not_active IP Right Cessation
- 1982-12-07 DK DK541982A patent/DK541982A/da not_active Application Discontinuation
- 1982-12-14 YU YU02758/82A patent/YU275882A/xx unknown
- 1982-12-14 YU YU02759/82A patent/YU275982A/xx unknown
- 1982-12-15 SU SU823523098A patent/SU1170968A3/ru active
- 1982-12-16 NO NO824232A patent/NO824232L/no unknown
- 1982-12-16 CA CA000417934A patent/CA1198125A/en not_active Expired
- 1982-12-16 HU HU824069A patent/HU186649B/hu not_active IP Right Cessation
- 1982-12-16 SE SE8207199A patent/SE452612B/sv not_active IP Right Cessation
- 1982-12-16 JP JP57221058A patent/JPS58159449A/ja active Pending
- 1982-12-16 JP JP57221057A patent/JPS58159446A/ja active Pending
- 1982-12-16 SE SE8207198A patent/SE8207198L/xx not_active Application Discontinuation
- 1982-12-16 NO NO824233A patent/NO155619C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK156567C (da) | 1990-03-05 |
| JPS58159446A (ja) | 1983-09-21 |
| KR840002768A (ko) | 1984-07-16 |
| YU275882A (en) | 1985-03-20 |
| SE8207199D0 (sv) | 1982-12-16 |
| SE8207198L (sv) | 1983-06-18 |
| CA1198125A (en) | 1985-12-17 |
| NO824233L (no) | 1983-06-20 |
| NO155619C (no) | 1987-04-29 |
| HU186649B (en) | 1985-08-28 |
| YU275982A (en) | 1985-03-20 |
| DK156567B (da) | 1989-09-11 |
| JPS58159449A (ja) | 1983-09-21 |
| SE8207198D0 (sv) | 1982-12-16 |
| NO155619B (no) | 1987-01-19 |
| SE8207199L (sv) | 1983-06-18 |
| SE452612B (sv) | 1987-12-07 |
| DK541982A (da) | 1983-06-18 |
| SU1170968A3 (ru) | 1985-07-30 |
| DK542082A (da) | 1983-06-18 |
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