DD156973A5 - Verfahren zur herstellung von 8 alpha-substituierten 6-methyl-10 alpha-h-ergolinen - Google Patents

Verfahren zur herstellung von 8 alpha-substituierten 6-methyl-10 alpha-h-ergolinen Download PDF

Info

Publication number: DD156973A5
Authority: DD; German Democratic Republic
Prior art keywords: alpha; substituted; methyl; ergolines; aniline
Prior art date: 1980-01-16

Application number

DD81226887A

Other languages

German (de)

English (en)

Inventor

Gerhard Sauer

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-01-16

Filing date

1981-01-08

Publication date

1982-10-06

1981-01-08 Application filed by Schering Ag filed Critical Schering Ag

1982-10-06 Publication of DD156973A5 publication Critical patent/DD156973A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 11
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 10
150000004982 aromatic amines Chemical class 0.000 claims abstract description 6
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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
229910052783 alkali metal Inorganic materials 0.000 claims abstract 2
150000001340 alkali metals Chemical class 0.000 claims abstract 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 2
239000001257 hydrogen Substances 0.000 claims abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
229910017464 nitrogen compound Inorganic materials 0.000 claims description 4
150000002830 nitrogen compounds Chemical class 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract description 6
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 abstract description 4
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract description 3
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 abstract description 3
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract description 3
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract description 3
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 description 2
FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 abstract description 2
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 abstract 1
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
125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000000203 mixture Substances 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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 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
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000011541 reaction mixture 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
UUYMPWWTAQZUQB-IINYFYTJSA-N (6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carbohydrazide Chemical compound C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(=O)NN)=C3C2=CNC3=C1 UUYMPWWTAQZUQB-IINYFYTJSA-N 0.000 description 1
GENAHGKEFJLNJB-IINYFYTJSA-N (6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-IINYFYTJSA-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
ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-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
WNRGWPVJGDABME-UHFFFAOYSA-N 3,5-Dimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1 WNRGWPVJGDABME-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
-1 6-methylergoline-8oL-methanol Chemical compound 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
BIXJFIJYBLJTMK-ZUZCIYMTSA-N [(6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC(C2=C[C@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-ZUZCIYMTSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229960003587 lisuride Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 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
210000003462 vein Anatomy 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)

DD81226887A 1980-01-16 1981-01-08 Verfahren zur herstellung von 8 alpha-substituierten 6-methyl-10 alpha-h-ergolinen DD156973A5 (de)

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
DD156973A5 true DD156973A5 (de)	1982-10-06

Family

ID=6092409

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81226887A DD156973A5 (de)	1980-01-16	1981-01-08	Verfahren zur herstellung von 8 alpha-substituierten 6-methyl-10 alpha-h-ergolinen

Country Status (12)

Country	Link
US (1)	US4417051A (cs)
EP (1)	EP0032684B1 (cs)
JP (1)	JPH0631232B2 (cs)
AT (1)	ATE16592T1 (cs)
CS (1)	CS231955B2 (cs)
DD (1)	DD156973A5 (cs)
DE (2)	DE3001752A1 (cs)
DK (1)	DK163995C (cs)
HU (1)	HU183285B (cs)
RO (1)	RO81385A (cs)
SU (1)	SU971101A3 (cs)
YU (1)	YU42111B (cs)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
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
BR0210915A (pt) *	2001-06-08	2004-06-08	Sod Conseils Rech Applic	Análogos quiméricos de 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)

* Cited by examiner, † Cited by third party
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
US3901893A (en) *	1970-05-18	1975-08-26	Richter Gedeon Vegyeszet	New dihydro-lysergic acid derivative
SE396753B (sv) *	1970-05-18	1977-10-03	Richter Gedeon Vegyeszet	Analogiforfarande for framstellning av en forening tillhorande dihydrolysergsyraserien
CH573937A5 (cs) *	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 DE DE8181100110T patent/DE3172932D1/de not_active Expired
- 1981-01-09 RO RO81103102A patent/RO81385A/ro unknown
- 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 HU HU8189A patent/HU183285B/hu not_active IP Right Cessation
- 1981-01-15 YU YU81/81A patent/YU42111B/xx unknown
- 1981-05-12 US US06/262,872 patent/US4417051A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
SU971101A3 (ru)	1982-10-30
DE3001752A1 (de)	1981-07-30
US4417051A (en)	1983-11-22
DK11981A (da)	1981-07-17
DE3172932D1 (en)	1986-01-02
JPH0631232B2 (ja)	1994-04-27
ATE16592T1 (de)	1985-12-15
DK163995C (da)	1992-10-12
YU42111B (en)	1988-04-30
HU183285B (en)	1984-04-28
EP0032684B1 (de)	1985-11-21
RO81385B (ro)	1983-06-30
JPS56100782A (en)	1981-08-12
DK163995B (da)	1992-04-27
EP0032684A1 (de)	1981-07-29
YU8181A (en)	1983-10-31
RO81385A (ro)	1983-07-07
CS231955B2 (en)	1985-01-16

Legal Events

Date	Code	Title	Description
1995-12-21	ENJ	Ceased due to non-payment of renewal fee

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