CS231955B2 - Manufacturing process of 8 alfa-substituted 6-methyl-ergolines - Google Patents
Manufacturing process of 8 alfa-substituted 6-methyl-ergolines Download PDFInfo
- Publication number
- CS231955B2 CS231955B2 CS8171A CS7181A CS231955B2 CS 231955 B2 CS231955 B2 CS 231955B2 CS 8171 A CS8171 A CS 8171A CS 7181 A CS7181 A CS 7181A CS 231955 B2 CS231955 B2 CS 231955B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- substituted
- ergolines
- alpha
- 8alpha
- Prior art date
Links
- NNDATQSUZGLGQT-BXUZGUMPSA-N 6-methylergoline Chemical class C1=CC([C@H]2CCCN([C@@H]2C2)C)=C3C2=CNC3=C1 NNDATQSUZGLGQT-BXUZGUMPSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 8
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 claims abstract description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims abstract description 4
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims abstract description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229940067157 phenylhydrazine Drugs 0.000 claims abstract description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- AHFZNJIKXMBLTJ-CQSZACIVSA-N (6ar)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline Chemical class C1=CC(C2=CCCN([C@@H]2C2)C)=C3C2=CNC3=C1 AHFZNJIKXMBLTJ-CQSZACIVSA-N 0.000 claims abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- WNRGWPVJGDABME-UHFFFAOYSA-N 3,5-Dimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1 WNRGWPVJGDABME-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 abstract description 6
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 abstract description 4
- FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 abstract description 2
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical group O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 abstract 1
- WVVOBOZHTQJXPB-UHFFFAOYSA-N N-anilino-N-nitronitramide Chemical compound [N+](=O)([O-])N(NC1=CC=CC=C1)[N+](=O)[O-] WVVOBOZHTQJXPB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 5
- -1 8alpha-substituted 9,10-didehydro-6-methyl-ergolines Chemical class 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- GENAHGKEFJLNJB-IINYFYTJSA-N Erginine Natural products C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-IINYFYTJSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- VUEGRGTYEAPQFU-CYBMUJFWSA-N (6ar)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline Chemical class C1=CC(C2=CCCN[C@@H]2C2)=C3C2=CNC3=C1 VUEGRGTYEAPQFU-CYBMUJFWSA-N 0.000 description 2
- ORBSYPFBZQJNJE-ZKYQVNSYSA-N (6ar,9s,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ORBSYPFBZQJNJE-ZKYQVNSYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229960004558 terguride Drugs 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VAYOSLLFUXYJDT-KBXCAEBGSA-N (6ar,9s)-n,n-diethyl-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-KBXCAEBGSA-N 0.000 description 1
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 1
- TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- SORAZNWVQFKAFD-IBIFCFAISA-N 3-[(6ar,9s,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea;(z)-but-2-enedioic acid Chemical group OC(=O)\C=C/C(O)=O.C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 SORAZNWVQFKAFD-IBIFCFAISA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- JOAHPSVPXZTVEP-YXJHDRRASA-N Terguride Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-YXJHDRRASA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229960003587 lisuride Drugs 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
- C07D457/06—Lysergic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803001752 DE3001752A1 (de) | 1980-01-16 | 1980-01-16 | Verfahren zur herstellung von 8(alpha)-substituierten 6-methylergolinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS231955B2 true CS231955B2 (en) | 1985-01-16 |
Family
ID=6092409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS8171A CS231955B2 (en) | 1980-01-16 | 1981-01-05 | Manufacturing process of 8 alfa-substituted 6-methyl-ergolines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4417051A (ro) |
| EP (1) | EP0032684B1 (ro) |
| JP (1) | JPH0631232B2 (ro) |
| AT (1) | ATE16592T1 (ro) |
| CS (1) | CS231955B2 (ro) |
| DD (1) | DD156973A5 (ro) |
| DE (2) | DE3001752A1 (ro) |
| DK (1) | DK163995C (ro) |
| HU (1) | HU183285B (ro) |
| RO (1) | RO81385A (ro) |
| SU (1) | SU971101A3 (ro) |
| YU (1) | YU42111B (ro) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH644606A5 (de) * | 1980-09-23 | 1984-08-15 | Sandoz Ag | Verfahren zur isomerisierung von 9,10-dihydrolysergsaeurederivaten. |
| DE3101535A1 (de) * | 1981-01-14 | 1982-08-12 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue (2-halogen-ergolinyl)-n'.n'-diethyl-harnstoffderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel |
| US4526892A (en) * | 1981-03-03 | 1985-07-02 | Farmitalia Carlo Erba, S.P.A. | Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas |
| DE3216870A1 (de) * | 1982-05-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pharmazeutische zubereitungen mit zytostatischer wirkung |
| PH21123A (en) * | 1983-04-28 | 1987-07-27 | Erba Farmitalia | Ergoline derivatives |
| DE3445784A1 (de) * | 1984-12-13 | 1986-06-26 | Schering AG, Berlin und Bergkamen, 1000 Berlin | Verfahren zur herstellung von ergolin-derivaten |
| DE3533675A1 (de) * | 1985-09-19 | 1987-03-26 | Schering Ag | Neue 12- und 13-brom-ergolinderivate |
| HU196598B (en) * | 1986-04-25 | 1988-12-28 | Richter Gedeon Vegyeszet | Process for producing 1- and/or 8-substituted 2-halogenated ergoline derivatives and pharmaceutics comprising such compounds |
| DE3623438C2 (de) * | 1986-07-10 | 1998-04-09 | Schering Ag | In 2-Stellung mit radioaktivem Iod markierte Ergolinylharnstoffderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Diagnostika |
| US5242678A (en) * | 1986-07-10 | 1993-09-07 | Schering Aktiengesellschaft | BR*-diagnostics for monoamine receptors |
| PT1401863E (pt) * | 2001-06-08 | 2009-07-23 | Ipsen Pharma | Análogos quiméricos da somatostatina-dopamina |
| JP4835153B2 (ja) * | 2005-12-22 | 2011-12-14 | 富士電機リテイルシステムズ株式会社 | 自動販売機の商品送出装置 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH386439A (de) * | 1961-01-31 | 1965-01-15 | Sandoz Ag | Verfahren zur Herstellung von neuen Dihydrolysergsäure-Derivaten |
| CH477447A (de) * | 1962-07-13 | 1969-08-31 | Farmaceutici Italia | Verfahren zur Herstellung neuer Derivate von Dihydro-D-lysergsäure- und 1-Methyl-dihydro-D-lysergsäure-a-hydroxyäthylamid |
| ES290275A2 (es) * | 1962-07-26 | 1964-03-01 | Farm Italia | Procedimiento para preparar nuevos compuestos de la 6-metil y la 1,6-dimetil-er-golina ii |
| CH507248A (de) * | 1967-03-16 | 1971-05-15 | Spofa Vereinigte Pharma Werke | Verfahren zur Herstellung von D-6-Methylergolin(I)ylessigsäure |
| SE396753B (sv) * | 1970-05-18 | 1977-10-03 | Richter Gedeon Vegyeszet | Analogiforfarande for framstellning av en forening tillhorande dihydrolysergsyraserien |
| US3901893A (en) * | 1970-05-18 | 1975-08-26 | Richter Gedeon Vegyeszet | New dihydro-lysergic acid derivative |
| CH573937A5 (ro) * | 1971-08-05 | 1976-03-31 | Spofa Vereinigte Pharma Werke | |
| US3968111A (en) * | 1974-12-06 | 1976-07-06 | Eli Lilly And Company | 8,8-Disubstituted-6-methylergolines and related compounds |
-
1980
- 1980-01-16 DE DE19803001752 patent/DE3001752A1/de not_active Withdrawn
- 1980-11-14 SU SU803003654A patent/SU971101A3/ru active
-
1981
- 1981-01-05 CS CS8171A patent/CS231955B2/cs unknown
- 1981-01-08 DD DD81226887A patent/DD156973A5/de not_active IP Right Cessation
- 1981-01-09 RO RO81103102A patent/RO81385A/ro unknown
- 1981-01-09 DE DE8181100110T patent/DE3172932D1/de not_active Expired
- 1981-01-09 AT AT81100110T patent/ATE16592T1/de not_active IP Right Cessation
- 1981-01-09 EP EP81100110A patent/EP0032684B1/de not_active Expired
- 1981-01-13 DK DK011981A patent/DK163995C/da not_active IP Right Cessation
- 1981-01-14 JP JP56003299A patent/JPH0631232B2/ja not_active Expired - Lifetime
- 1981-01-15 YU YU81/81A patent/YU42111B/xx unknown
- 1981-01-15 HU HU8189A patent/HU183285B/hu not_active IP Right Cessation
- 1981-05-12 US US06/262,872 patent/US4417051A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| YU42111B (en) | 1988-04-30 |
| RO81385A (ro) | 1983-07-07 |
| RO81385B (ro) | 1983-06-30 |
| DE3172932D1 (en) | 1986-01-02 |
| HU183285B (en) | 1984-04-28 |
| SU971101A3 (ru) | 1982-10-30 |
| JPS56100782A (en) | 1981-08-12 |
| EP0032684A1 (de) | 1981-07-29 |
| EP0032684B1 (de) | 1985-11-21 |
| DK11981A (da) | 1981-07-17 |
| DK163995C (da) | 1992-10-12 |
| ATE16592T1 (de) | 1985-12-15 |
| DD156973A5 (de) | 1982-10-06 |
| DK163995B (da) | 1992-04-27 |
| DE3001752A1 (de) | 1981-07-30 |
| YU8181A (en) | 1983-10-31 |
| JPH0631232B2 (ja) | 1994-04-27 |
| US4417051A (en) | 1983-11-22 |
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