FI62086C - Foerfarande foer framstaellning av bronkosekreterolytiska 5,11-dihydro-5h-pyrido(2,3-b)(1,5)bensodiazepin-5-oner - Google Patents
Foerfarande foer framstaellning av bronkosekreterolytiska 5,11-dihydro-5h-pyrido(2,3-b)(1,5)bensodiazepin-5-oner Download PDFInfo
- Publication number
- FI62086C FI62086C FI772772A FI772772A FI62086C FI 62086 C FI62086 C FI 62086C FI 772772 A FI772772 A FI 772772A FI 772772 A FI772772 A FI 772772A FI 62086 C FI62086 C FI 62086C
- Authority
- FI
- Finland
- Prior art keywords
- pyrido
- dihydro
- benzodiazepin
- group
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- -1 pyrrolidino, piperidino, hexamethyleneimino, morpholino Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 21
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
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- 239000002253 acid Substances 0.000 claims description 4
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- CJHKJXZMFZKGHI-UHFFFAOYSA-N 1h-pyrido[2,3-i][1,2]benzodiazepine Chemical class N1N=CC=CC2=CC=C(N=CC=C3)C3=C12 CJHKJXZMFZKGHI-UHFFFAOYSA-N 0.000 claims 1
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- QCDYMKKLCBKXRR-UHFFFAOYSA-N 2-methyl-6,11-dihydropyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound N1C2=CC=CC=C2NC(=O)C2=CC=C(C)N=C12 QCDYMKKLCBKXRR-UHFFFAOYSA-N 0.000 description 1
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 1
- KCBCBDAJCCQJIS-UHFFFAOYSA-N 3-(diethylamino)propyl 2,6,8,9-tetramethyl-5-oxopyrido[3,2-c][1,5]benzodiazepine-11-carboxylate Chemical compound C(C)N(CCCOC(=O)N1C2=C(C(N(C3=C1C=C(C(=C3)C)C)C)=O)C=CC(=N2)C)CC KCBCBDAJCCQJIS-UHFFFAOYSA-N 0.000 description 1
- VTWZICMJJJQLKT-UHFFFAOYSA-N 3-(dimethylamino)propyl 4-methylbenzenesulfonate Chemical compound CN(C)CCCOS(=O)(=O)C1=CC=C(C)C=C1 VTWZICMJJJQLKT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RXYQHVMJQFHKDX-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine Chemical compound CC(C)N(C(C)C)CCCCl RXYQHVMJQFHKDX-UHFFFAOYSA-N 0.000 description 1
- UUNYBOOZTYTWLD-UHFFFAOYSA-N 3-chloro-n-ethyl-n-propan-2-ylpropan-1-amine Chemical compound CCN(C(C)C)CCCCl UUNYBOOZTYTWLD-UHFFFAOYSA-N 0.000 description 1
- XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- SFRAVXBSPHJEBZ-UHFFFAOYSA-N 6,11-dihydropyrido[3,2-c][1,5]benzodiazepin-5-one Chemical compound O=C1NC2=CC=CC=C2NC2=NC=CC=C12 SFRAVXBSPHJEBZ-UHFFFAOYSA-N 0.000 description 1
- LWMJTHXOVXAPKT-UHFFFAOYSA-N 6h-cinnolin-5-one Chemical compound N1=CC=C2C(=O)CC=CC2=N1 LWMJTHXOVXAPKT-UHFFFAOYSA-N 0.000 description 1
- URDCJWRYTVXAMN-UHFFFAOYSA-N C1=CC(=O)C2=C(C=NC=C2)N=C1 Chemical compound C1=CC(=O)C2=C(C=NC=C2)N=C1 URDCJWRYTVXAMN-UHFFFAOYSA-N 0.000 description 1
- GRYUTCQLUWJFBC-UHFFFAOYSA-N CCC1=NC2=C(C=C1)C(=O)N(C3=C(N2CCCN(CC)CC)C=C(C(=C3)CC)CC)CC Chemical compound CCC1=NC2=C(C=C1)C(=O)N(C3=C(N2CCCN(CC)CC)C=C(C(=C3)CC)CC)CC GRYUTCQLUWJFBC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZGLDQGIONSGJCN-UHFFFAOYSA-N diazepin-5-one Chemical compound O=C1C=CN=NC=C1 ZGLDQGIONSGJCN-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- GTNGRRLCBNNJHB-UHFFFAOYSA-N n-benzyl-3-chloro-n-ethylpropan-1-amine Chemical compound ClCCCN(CC)CC1=CC=CC=C1 GTNGRRLCBNNJHB-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2644121 | 1976-09-30 | ||
| DE19762644121 DE2644121A1 (de) | 1976-09-30 | 1976-09-30 | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772772A7 FI772772A7 (fi) | 1978-03-31 |
| FI62086B FI62086B (fi) | 1982-07-30 |
| FI62086C true FI62086C (fi) | 1982-11-10 |
Family
ID=5989298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772772A FI62086C (fi) | 1976-09-30 | 1977-09-20 | Foerfarande foer framstaellning av bronkosekreterolytiska 5,11-dihydro-5h-pyrido(2,3-b)(1,5)bensodiazepin-5-oner |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4167570A (cs) |
| JP (1) | JPS5344595A (cs) |
| AT (1) | AT355580B (cs) |
| AU (1) | AU512831B2 (cs) |
| BE (1) | BE859213A (cs) |
| BG (1) | BG28066A3 (cs) |
| CA (1) | CA1084049A (cs) |
| CH (3) | CH637955A5 (cs) |
| CS (1) | CS196388B2 (cs) |
| DD (1) | DD134351A5 (cs) |
| DE (1) | DE2644121A1 (cs) |
| DK (1) | DK143752C (cs) |
| ES (3) | ES462746A1 (cs) |
| FI (1) | FI62086C (cs) |
| FR (1) | FR2372164A1 (cs) |
| GB (1) | GB1538366A (cs) |
| GR (1) | GR64050B (cs) |
| HU (1) | HU179802B (cs) |
| IE (1) | IE45702B1 (cs) |
| IL (1) | IL53026A (cs) |
| LU (1) | LU78192A1 (cs) |
| NL (1) | NL7710646A (cs) |
| NO (1) | NO146776C (cs) |
| NZ (1) | NZ185302A (cs) |
| PH (1) | PH14714A (cs) |
| PL (1) | PL104866B1 (cs) |
| PT (1) | PT67097B (cs) |
| SE (1) | SE425740B (cs) |
| SU (2) | SU786900A3 (cs) |
| YU (1) | YU231277A (cs) |
| ZA (1) | ZA775816B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5695597U (cs) * | 1979-12-18 | 1981-07-29 | ||
| DE3204401A1 (de) * | 1982-02-09 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4749788A (en) * | 1987-04-13 | 1988-06-07 | A. H. Robins Company, Incorporated | Process for the preparation of aryl-pyrido(1,4) benzodiazepines |
| DE69031845T2 (de) * | 1989-04-20 | 1998-05-07 | Boehringer Ingelheim Pharma | 6,11-Dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one und Thione und ihre Verwendung für die Vorbeugung oder Behandlung von AIDS |
| US6048857A (en) * | 1989-10-17 | 2000-04-11 | Ellinwood, Jr.; Everett H. | Dosing method of administering medicaments via inhalation administration |
| FR2850654A1 (fr) * | 2003-02-03 | 2004-08-06 | Servier Lab | Nouveaux derives d'azepines tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2424811C3 (de) * | 1974-05-22 | 1981-08-20 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| PL60440Y1 (en) * | 1999-01-26 | 2004-05-31 | Pil I Narzedzi Wapienica Sa Fa | Double-sided hacksaw blade |
| PL60439Y1 (en) * | 1999-09-03 | 2004-05-31 | Zdt Komag Sp Z Oo | Regenerated scraper of a chain-type scraper conveyor |
-
1976
- 1976-09-30 DE DE19762644121 patent/DE2644121A1/de not_active Withdrawn
-
1977
- 1977-08-29 AT AT622077A patent/AT355580B/de active
- 1977-09-20 FI FI772772A patent/FI62086C/fi not_active IP Right Cessation
- 1977-09-20 BG BG037376A patent/BG28066A3/xx unknown
- 1977-09-22 AU AU29038/77A patent/AU512831B2/en not_active Expired
- 1977-09-26 DD DD77201205A patent/DD134351A5/xx unknown
- 1977-09-27 SU SU772524544A patent/SU786900A3/ru active
- 1977-09-27 CH CH1180077A patent/CH637955A5/de not_active IP Right Cessation
- 1977-09-27 CS CS776253A patent/CS196388B2/cs unknown
- 1977-09-28 CA CA287,654A patent/CA1084049A/en not_active Expired
- 1977-09-28 YU YU02312/77A patent/YU231277A/xx unknown
- 1977-09-28 LU LU78192A patent/LU78192A1/xx unknown
- 1977-09-28 HU HU77TO1063A patent/HU179802B/hu unknown
- 1977-09-28 US US05/837,578 patent/US4167570A/en not_active Expired - Lifetime
- 1977-09-28 DK DK428377A patent/DK143752C/da not_active IP Right Cessation
- 1977-09-29 IE IE1994/77A patent/IE45702B1/en unknown
- 1977-09-29 GB GB40555/77A patent/GB1538366A/en not_active Expired
- 1977-09-29 PH PH20285A patent/PH14714A/en unknown
- 1977-09-29 ZA ZA00775816A patent/ZA775816B/xx unknown
- 1977-09-29 NL NL7710646A patent/NL7710646A/xx not_active Application Discontinuation
- 1977-09-29 PL PL1977201133A patent/PL104866B1/xx unknown
- 1977-09-29 NZ NZ185302A patent/NZ185302A/xx unknown
- 1977-09-29 NO NO773344A patent/NO146776C/no unknown
- 1977-09-29 ES ES462746A patent/ES462746A1/es not_active Expired
- 1977-09-29 JP JP11730977A patent/JPS5344595A/ja active Pending
- 1977-09-29 IL IL53026A patent/IL53026A/xx unknown
- 1977-09-29 GR GR54460A patent/GR64050B/el unknown
- 1977-09-29 PT PT67097A patent/PT67097B/pt unknown
- 1977-09-29 BE BE181322A patent/BE859213A/xx unknown
- 1977-09-30 SE SE7710993A patent/SE425740B/xx unknown
- 1977-09-30 FR FR7729530A patent/FR2372164A1/fr active Granted
-
1978
- 1978-04-06 ES ES468585A patent/ES468585A1/es not_active Expired
- 1978-04-06 ES ES468586A patent/ES468586A1/es not_active Expired
- 1978-06-09 SU SU782624299A patent/SU722486A3/ru active
-
1982
- 1982-05-13 CH CH298682A patent/CH637957A5/de not_active IP Right Cessation
- 1982-05-13 CH CH298782A patent/CH637958A5/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DR. KARL THOMAE GESELLSCHAFT MIT |