SU730301A3 - Способ получени замещенных 1-сульфонилбензимидазолов - Google Patents
Способ получени замещенных 1-сульфонилбензимидазолов Download PDFInfo
- Publication number
- SU730301A3 SU730301A3 SU782647712A SU2647712A SU730301A3 SU 730301 A3 SU730301 A3 SU 730301A3 SU 782647712 A SU782647712 A SU 782647712A SU 2647712 A SU2647712 A SU 2647712A SU 730301 A3 SU730301 A3 SU 730301A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- sulfonylbenzimidazoles
- alkyl
- preparing substituted
- dithiolan
- methanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 4
- -1 1, 3-dithiolan-2-yl Chemical group 0.000 claims description 3
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 claims description 2
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
трехфтористого бора при комнатной температуре, и реакцию ведут 2ч. Выпавший осадок промывают холодным метанолом и получают 65 мг циклического тиоацетал 1-диметиламиносульфонил-2-амино-5 (6)-(дитиолан-2-ил)-бензимидазола . Промывные воды и фильтраты соедин ют и смешивают с 20 мл насыщенного раствора карбоната натри . Водный раствор экстрагируют этилацетатом. Экстракт промывают насыщенным раствором хлористого натри и сушат над сульфатом магни , Этилацетат отгон ют досуха в вакууме. Твердый остаток обрабатывают метанолом и нерастворимый в метаноле осадок собирают. Выход 155 мг. Метанольный фильтрат выпаривают досуха в вакууме и получаот еще 55 мг целевого продукта, м/е 344.
Пример 2. 1-диметиламиносульфонил-2-амино-5 (6)-(1,5-дитиола-2-ил )-бензимидазол.
220 мг (0,6 ммол ) 1-диметиламиносульфонил-2-амино-5 (6)-формилбензимидазола , 2 мл метанола, 0,15 мл (1,6 ммол ) 1,3-пропандитиола и 0,75 мл эфирата трехфтористого бора смешивают при комнатной температуре К смеси прибавл ют примерно 6 мл диэтилового эфира, провод т реакцию 2 ч. Реакционную смесь разбавл ют до объема 12 мл диэтиловым эфиром и выпаривают осадок, центрифугируют И верхний слой жидкости декантируют Осадок суспендируют в диэтиловом эфире и смесь снова центрифугируют. Верхний слой жидкости декантируют и твердый продукт сушат в вакууме. .Выход 224 мг (75%) циклического тиоацетал , 1-диметиламиносульфонил-2-амино-5 (6)-(1,5-дитиолан-2-ил)-бензимидазола , т/е. 358.
Claims (1)
- Формула изобретениСпособ получени замещенных 1-сульфонилбензимидазолов общей формулы(I)5 где R обозначает С, -Сц-алкил илиNRgRq-группу, в которой R И Нц,.независимо друг от друга, обозначают С| -Сз-алкил; Rj, обозначает 1,,3-дитиолан-2-ил или 1,З-дитиен-2-ил, наход щийс в положени х 5 или 6 бензиьлидазольного кольца, отличающийс тем, что соединение общей формулыв которой R имеет значени , указанные 30 выше, подвергают взаимодействию с этандитиолом или 1,3-пропандитиолом в присутствии эфирата трифторида бора в среде органического растворител , с последующим выделением целевого 35 продукта.Источники информации, прин тые во внимание при экспертизе 1. Fieser L.F. 3 .Am Chem Бос., Preparation of Ethylenethioketals 1954, 76, 1945,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60841575A | 1975-08-28 | 1975-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU730301A3 true SU730301A3 (ru) | 1980-04-25 |
Family
ID=24436401
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762390305A SU691089A3 (ru) | 1975-08-28 | 1976-08-26 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772524545A SU730300A3 (ru) | 1975-08-28 | 1977-09-27 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772525453A SU685151A3 (ru) | 1975-08-28 | 1977-09-28 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772527447A SU679140A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772526201A SU884570A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU782647712A SU730301A3 (ru) | 1975-08-28 | 1978-08-16 | Способ получени замещенных 1-сульфонилбензимидазолов |
| SU782654600A SU727142A3 (ru) | 1975-08-28 | 1978-08-31 | Способ получени замещенных 1-сульфонилбензимидазолов |
| SU782676704A SU919593A3 (ru) | 1975-08-28 | 1978-10-23 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU782676705A SU784767A3 (ru) | 1975-08-28 | 1978-10-24 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
Family Applications Before (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762390305A SU691089A3 (ru) | 1975-08-28 | 1976-08-26 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772524545A SU730300A3 (ru) | 1975-08-28 | 1977-09-27 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772525453A SU685151A3 (ru) | 1975-08-28 | 1977-09-28 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772527447A SU679140A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772526201A SU884570A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782654600A SU727142A3 (ru) | 1975-08-28 | 1978-08-31 | Способ получени замещенных 1-сульфонилбензимидазолов |
| SU782676704A SU919593A3 (ru) | 1975-08-28 | 1978-10-23 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU782676705A SU784767A3 (ru) | 1975-08-28 | 1978-10-24 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4118742A (ru) |
| JP (4) | JPS5633392B2 (ru) |
| AR (4) | AR219284A1 (ru) |
| AT (1) | AT360005B (ru) |
| AU (1) | AU502756B2 (ru) |
| BE (1) | BE845641A (ru) |
| BG (1) | BG27548A3 (ru) |
| CA (1) | CA1064501A (ru) |
| CH (8) | CH626612A5 (ru) |
| DD (1) | DD126518A5 (ru) |
| DE (1) | DE2638551A1 (ru) |
| DK (1) | DK154764C (ru) |
| ES (5) | ES451018A1 (ru) |
| FR (1) | FR2321883A1 (ru) |
| GB (1) | GB1562812A (ru) |
| GR (1) | GR61627B (ru) |
| HU (1) | HU173988B (ru) |
| IE (1) | IE43531B1 (ru) |
| IL (1) | IL50292A (ru) |
| MX (1) | MX3654E (ru) |
| NL (1) | NL7609414A (ru) |
| NZ (1) | NZ181789A (ru) |
| PL (4) | PL110145B1 (ru) |
| PT (1) | PT65486B (ru) |
| RO (5) | RO72313A (ru) |
| SU (9) | SU691089A3 (ru) |
| YU (2) | YU203476A (ru) |
| ZA (1) | ZA765142B (ru) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191832A (en) * | 1979-03-12 | 1980-03-04 | Eli Lilly And Company | Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles |
| CA1178889A (en) * | 1980-08-28 | 1984-12-04 | Kenneth S. Su | Intranasal formulation |
| FR2521141A1 (fr) * | 1982-02-09 | 1983-08-12 | Rhone Poulenc Agrochimie | Nouveaux derives du cyano-2 benzimidazole, leur preparation et leur utilisation comme fongicides |
| US4463181A (en) * | 1982-04-08 | 1984-07-31 | Eli Lilly And Company | Process for removing sulfonyl groups from benzimidazole isomers |
| US4434288A (en) * | 1982-04-08 | 1984-02-28 | Eli Lilly And Company | Preparation of substituted 1-thiazinyl or 1-thiazolyl-2-aminobenzimidazoles |
| US4420479A (en) * | 1982-04-08 | 1983-12-13 | Eli Lilly And Company | Olefinic benzimidazoles, formulations, and antiviral methods |
| IL68297A (en) * | 1982-04-08 | 1986-09-30 | Lilly Co Eli | Process for removing 1-sulfonyl groups from 2-amino-5(6)-substituted benzimidazoles |
| US4483986A (en) * | 1982-05-03 | 1984-11-20 | Eli Lilly And Company | 4-Nitrobenzophenone compounds |
| US4629811A (en) * | 1982-05-03 | 1986-12-16 | Eli Lilly And Company | 3-sulfonylamino-4-aminobenzophenone derivatives |
| US4645861A (en) * | 1982-05-03 | 1987-02-24 | Eli Lilly And Company | 3-sulfonylamino-4-amino phenyl acyl derivatives |
| US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
| US4501921A (en) * | 1982-11-18 | 1985-02-26 | Eli Lilly And Company | Synthesis of alkylidene intermediates |
| US4435418A (en) * | 1982-12-13 | 1984-03-06 | Smithkline Beckman Corporation | 5-Phenylethenylbenzimidazoles |
| JPS62196293U (ru) * | 1986-06-03 | 1987-12-14 | ||
| CA1339133C (en) * | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms |
| JPS6410894A (en) * | 1987-06-30 | 1989-01-13 | Nitto Koji Kk | Burying propulsion correcting method and device for propulsive pipe for burying hume pipe |
| US5545653A (en) * | 1995-06-07 | 1996-08-13 | Eli Lilly And Company | Anti-viral compounds |
| AU7715198A (en) * | 1997-06-04 | 1998-12-21 | Eli Lilly And Company | Anti-viral compounds |
| US6358971B1 (en) | 1998-05-20 | 2002-03-19 | Eli Lilly And Company | Anti-viral compounds |
| US7470723B2 (en) * | 2003-03-05 | 2008-12-30 | Celgene Corporation | Diphenylethylene compounds and uses thereof |
| US8287843B2 (en) * | 2003-06-23 | 2012-10-16 | Colgate-Palmolive Company | Antiplaque oral care compositions |
| SG144809A1 (en) * | 2007-01-11 | 2008-08-28 | Millipore U K Ltd | Benzimidazole compounds and their use as chromatographic ligands |
| CN118084937A (zh) | 2018-08-21 | 2024-05-28 | 杏林制药株式会社 | 双环杂芳族环衍生物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1170737A (en) * | 1964-05-27 | 1969-11-12 | Fisons Pest Control Ltd | Substituted Benzimadazoles and their use as Acaricides |
| US3682952A (en) * | 1964-08-04 | 1972-08-08 | Smith Kline French Lab | 5(6)-n-butyl-2-carbomethoxy-benzimidazole |
| DE2034643A1 (de) * | 1970-03-06 | 1971-09-16 | Deutsche Akademie der Wissenschaften zu Berlin, χ 1199 Berlin | Verfahren zur Herstellung von virustatisch wirksamen p-N-Methylnitrosaminophenyl-Verbindungen |
| BE795098A (fr) * | 1972-02-09 | 1973-08-07 | Bayer Ag | Nouveaux 1-aminosulfonyl-2-amino-benzimidazoles, leur procede de preparation et leur application comme fongicides |
| BE795099A (fr) * | 1972-02-09 | 1973-08-07 | Bayer Ag | Nouvelles 1-acyl-3-aminosulfonyl-2-imino-benzimidazolines, leur procede de preparation et leur application comme fongicides |
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1976
- 1976-08-17 PT PT65486A patent/PT65486B/pt unknown
- 1976-08-17 GR GR51488A patent/GR61627B/el unknown
- 1976-08-17 NZ NZ181789A patent/NZ181789A/xx unknown
- 1976-08-17 MX MX763667U patent/MX3654E/es unknown
- 1976-08-18 HU HU76EI694A patent/HU173988B/hu unknown
- 1976-08-18 IL IL50292A patent/IL50292A/xx unknown
- 1976-08-19 YU YU02034/76A patent/YU203476A/xx unknown
- 1976-08-19 CA CA259,487A patent/CA1064501A/en not_active Expired
- 1976-08-19 AR AR264377A patent/AR219284A1/es active
- 1976-08-19 AU AU16982/76A patent/AU502756B2/en not_active Expired
- 1976-08-24 NL NL7609414A patent/NL7609414A/xx not_active Application Discontinuation
- 1976-08-24 IE IE1884/76A patent/IE43531B1/en not_active IP Right Cessation
- 1976-08-24 GB GB35153/76A patent/GB1562812A/en not_active Expired
- 1976-08-25 RO RO7687359A patent/RO72313A/ro unknown
- 1976-08-25 RO RO7698737A patent/RO78125A/ro unknown
- 1976-08-25 JP JP10219076A patent/JPS5633392B2/ja not_active Expired
- 1976-08-25 RO RO7698736A patent/RO78124A/ro unknown
- 1976-08-25 RO RO7698734A patent/RO78122A/ro unknown
- 1976-08-25 RO RO7698735A patent/RO78123A/ro unknown
- 1976-08-26 PL PL1976209627A patent/PL110145B1/pl unknown
- 1976-08-26 PL PL1976218028A patent/PL112910B1/pl unknown
- 1976-08-26 SU SU762390305A patent/SU691089A3/ru active
- 1976-08-26 PL PL1976209626A patent/PL115117B1/pl unknown
- 1976-08-26 DK DK386076A patent/DK154764C/da not_active IP Right Cessation
- 1976-08-26 ES ES451018A patent/ES451018A1/es not_active Expired
- 1976-08-26 DE DE19762638551 patent/DE2638551A1/de active Granted
- 1976-08-26 PL PL1976192018A patent/PL106947B1/pl unknown
- 1976-08-26 BG BG034083A patent/BG27548A3/xx unknown
- 1976-08-26 AT AT636376A patent/AT360005B/de not_active IP Right Cessation
- 1976-08-26 CH CH1085476A patent/CH626612A5/de not_active IP Right Cessation
- 1976-08-27 BE BE1007586A patent/BE845641A/xx not_active IP Right Cessation
- 1976-08-27 DD DD194505A patent/DD126518A5/xx unknown
- 1976-08-27 FR FR7626026A patent/FR2321883A1/fr active Granted
- 1976-08-27 ZA ZA00765142A patent/ZA765142B/xx unknown
- 1976-12-15 US US05/750,991 patent/US4118742A/en not_active Expired - Lifetime
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1977
- 1977-02-14 YU YU00390/77A patent/YU39077A/xx unknown
- 1977-08-16 ES ES461641A patent/ES461641A1/es not_active Expired
- 1977-08-16 ES ES461644A patent/ES461644A1/es not_active Expired
- 1977-08-16 AR AR268810A patent/AR221037A1/es active
- 1977-08-16 ES ES461643A patent/ES461643A1/es not_active Expired
- 1977-08-16 ES ES461642A patent/ES461642A1/es not_active Expired
- 1977-09-27 SU SU772524545A patent/SU730300A3/ru active
- 1977-09-28 SU SU772525453A patent/SU685151A3/ru active
- 1977-09-29 SU SU772527447A patent/SU679140A3/ru active
- 1977-09-29 SU SU772526201A patent/SU884570A3/ru active
-
1978
- 1978-06-15 AR AR272626A patent/AR220344A1/es active
- 1978-06-15 AR AR272625A patent/AR221701A1/es active
- 1978-08-16 SU SU782647712A patent/SU730301A3/ru active
- 1978-08-31 SU SU782654600A patent/SU727142A3/ru active
- 1978-10-23 SU SU782676704A patent/SU919593A3/ru active
- 1978-10-24 SU SU782676705A patent/SU784767A3/ru active
-
1980
- 1980-06-30 CH CH502780A patent/CH627748A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502980A patent/CH628035A5/de not_active IP Right Cessation
- 1980-06-30 CH CH503080A patent/CH627753A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502880A patent/CH627455A5/de not_active IP Right Cessation
- 1980-07-03 CH CH513681A patent/CH630376A5/de not_active IP Right Cessation
- 1980-07-03 CH CH513781A patent/CH630917A5/de not_active IP Right Cessation
- 1980-11-26 JP JP55167905A patent/JPS57112389A/ja active Pending
- 1980-11-26 JP JP55167907A patent/JPS591712B2/ja not_active Expired
- 1980-11-26 JP JP55167906A patent/JPS5823876B2/ja not_active Expired
-
1981
- 1981-08-10 CH CH513881A patent/CH631447A5/de not_active IP Right Cessation
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