DK142813B - Analogifremgangsmåde til fremstilling af 1-thiazolinyl- og 1-thiazinyl-benzimidazolestere. - Google Patents
Analogifremgangsmåde til fremstilling af 1-thiazolinyl- og 1-thiazinyl-benzimidazolestere. Download PDFInfo
- Publication number
- DK142813B DK142813B DK386276AA DK386276A DK142813B DK 142813 B DK142813 B DK 142813B DK 386276A A DK386276A A DK 386276AA DK 386276 A DK386276 A DK 386276A DK 142813 B DK142813 B DK 142813B
- Authority
- DK
- Denmark
- Prior art keywords
- benzimidazole
- amino
- give
- thiazolinyl
- carbon atoms
- Prior art date
Links
- -1 1-thiazolinyl Chemical group 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 6
- OYOQQMBCCJDDIQ-UHFFFAOYSA-N 3-(benzimidazol-1-yl)-2h-thiazine Chemical class N1SC=CC=C1N1C2=CC=CC=C2N=C1 OYOQQMBCCJDDIQ-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000000840 anti-viral effect Effects 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
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- 238000004458 analytical method Methods 0.000 description 14
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
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- 125000002769 thiazolinyl group Chemical group 0.000 description 8
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 150000001556 benzimidazoles Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 125000004301 thiazolin-2-yl group Chemical group [H]C1([H])SC(*)=NC1([H])[H] 0.000 description 7
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 231100001228 moderately toxic Toxicity 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SYAIBOZYDSNSJG-UHFFFAOYSA-N propan-2-yl 4-chloro-3-nitrobenzoate Chemical compound CC(C)OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 SYAIBOZYDSNSJG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- ZKAWOKCRIUUHMI-UHFFFAOYSA-N tert-butyl 2-amino-3-(4,5-dihydro-1,3-thiazol-2-yl)benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OC(C)(C)C)=CC=C2N=C(N)N1C1=NCCS1 ZKAWOKCRIUUHMI-UHFFFAOYSA-N 0.000 description 1
- PSXWMTJULZJDAI-UHFFFAOYSA-N tert-butyl 3,4-diaminobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(N)C(N)=C1 PSXWMTJULZJDAI-UHFFFAOYSA-N 0.000 description 1
- SETXXIKWSUYINZ-UHFFFAOYSA-N tert-butyl 3,4-dinitrobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 SETXXIKWSUYINZ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63320375 | 1975-11-19 | ||
| US05/633,203 US4008243A (en) | 1975-11-19 | 1975-11-19 | Antiviral thiazolinyl or thiazinyl benzimidazole esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK386276A DK386276A (en, 2012) | 1977-05-20 |
| DK142813B true DK142813B (da) | 1981-02-02 |
| DK142813C DK142813C (en, 2012) | 1981-09-21 |
Family
ID=24538665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK386276AA DK142813B (da) | 1975-11-19 | 1976-08-26 | Analogifremgangsmåde til fremstilling af 1-thiazolinyl- og 1-thiazinyl-benzimidazolestere. |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4008243A (en, 2012) |
| JP (1) | JPS5265269A (en, 2012) |
| AR (1) | AR218228A1 (en, 2012) |
| AT (1) | AT358029B (en, 2012) |
| AU (1) | AU498521B2 (en, 2012) |
| BE (1) | BE845643A (en, 2012) |
| BG (1) | BG27550A3 (en, 2012) |
| CA (1) | CA1059510A (en, 2012) |
| CH (1) | CH623052A5 (en, 2012) |
| CS (1) | CS199280B2 (en, 2012) |
| DD (1) | DD128675A5 (en, 2012) |
| DE (1) | DE2638552A1 (en, 2012) |
| DK (1) | DK142813B (en, 2012) |
| ES (2) | ES451020A1 (en, 2012) |
| FR (1) | FR2332011A1 (en, 2012) |
| GB (1) | GB1561481A (en, 2012) |
| GR (1) | GR61722B (en, 2012) |
| HU (1) | HU172633B (en, 2012) |
| IE (1) | IE43618B1 (en, 2012) |
| IL (1) | IL50294A (en, 2012) |
| MX (1) | MX4067E (en, 2012) |
| NL (1) | NL7609415A (en, 2012) |
| NZ (1) | NZ181788A (en, 2012) |
| PH (1) | PH13615A (en, 2012) |
| PL (2) | PL105486B1 (en, 2012) |
| PT (1) | PT65488B (en, 2012) |
| RO (1) | RO72653A (en, 2012) |
| SU (1) | SU721003A3 (en, 2012) |
| YU (1) | YU203576A (en, 2012) |
| ZA (1) | ZA765143B (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1076582A (en) * | 1975-10-28 | 1980-04-29 | Charles J. Paget | Antiviral thiazolinyl or thiazinyl ketobenzimidazoles |
| US4293558A (en) * | 1975-10-28 | 1981-10-06 | Eli Lilly And Company | Antiviral thiazolinyl benzimidazoles and derivatives |
| US4191832A (en) * | 1979-03-12 | 1980-03-04 | Eli Lilly And Company | Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles |
| US4338315A (en) * | 1979-11-14 | 1982-07-06 | Eli Lilly And Company | Antiviral method employing thiazinyl benzimidazole derivatives |
| US4401817A (en) * | 1981-04-20 | 1983-08-30 | Eli Lilly And Company | Carbonyl-substituted 1-sulfonylbenzimidazoles |
| 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 |
| 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 |
| US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
| US5508594A (en) * | 1994-06-10 | 1996-04-16 | Westinghouse Electric Corp | Electric vehicle chassis controller |
| US6358971B1 (en) | 1998-05-20 | 2002-03-19 | Eli Lilly And Company | Anti-viral compounds |
| WO2008021338A2 (en) * | 2006-08-15 | 2008-02-21 | Wyeth | Tricyclic oxazolidone derivatives useful as pr modulators |
| TW200815428A (en) * | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
| US7649007B2 (en) * | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| US20080045560A1 (en) * | 2006-08-15 | 2008-02-21 | Wyeth | Pyrrolidine and related derivatives useful as PR modulators |
| US7652018B2 (en) * | 2006-08-15 | 2010-01-26 | Wyeth Llc | Imidazolidin-2-one derivatives useful as PR modulators |
| US7538107B2 (en) | 2006-08-15 | 2009-05-26 | Wyeth | Oxazinan-2-one derivatives useful as PR modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3749717A (en) * | 1971-05-04 | 1973-07-31 | Squibb & Sons Inc | Thiazolinyl and thiazinyl derivatives of benzimidazoles |
| US3825537A (en) * | 1972-02-28 | 1974-07-23 | Squibb & Sons Inc | 1-thiazolin-2-yl(or thiazin-2-yl)-2-aminobenzimidazoles and derivatives thereof |
| US3833574A (en) * | 1972-07-31 | 1974-09-03 | Squibb & Sons Inc | Benzimidazolinone compounds |
-
1975
- 1975-11-19 US US05/633,203 patent/US4008243A/en not_active Expired - Lifetime
-
1976
- 1976-08-17 PT PT65488A patent/PT65488B/pt unknown
- 1976-08-17 NZ NZ181788A patent/NZ181788A/xx unknown
- 1976-08-17 GR GR51490A patent/GR61722B/el unknown
- 1976-08-17 MX MX763669U patent/MX4067E/es unknown
- 1976-08-18 HU HU76EI00000693A patent/HU172633B/hu unknown
- 1976-08-18 IL IL50294A patent/IL50294A/xx unknown
- 1976-08-19 AU AU16984/76A patent/AU498521B2/en not_active Expired
- 1976-08-19 YU YU02035/76A patent/YU203576A/xx unknown
- 1976-08-19 AR AR264379A patent/AR218228A1/es active
- 1976-08-19 CA CA259,393A patent/CA1059510A/en not_active Expired
- 1976-08-20 PH PH18822A patent/PH13615A/en unknown
- 1976-08-24 CS CS765494A patent/CS199280B2/cs unknown
- 1976-08-24 NL NL7609415A patent/NL7609415A/xx not_active Application Discontinuation
- 1976-08-24 IE IE1883/76A patent/IE43618B1/en unknown
- 1976-08-24 GB GB35092/76A patent/GB1561481A/en not_active Expired
- 1976-08-25 RO RO7687361A patent/RO72653A/ro unknown
- 1976-08-26 DE DE19762638552 patent/DE2638552A1/de not_active Withdrawn
- 1976-08-26 DK DK386276AA patent/DK142813B/da not_active IP Right Cessation
- 1976-08-26 SU SU762390302A patent/SU721003A3/ru active
- 1976-08-26 CH CH1085676A patent/CH623052A5/de not_active IP Right Cessation
- 1976-08-26 ES ES451020A patent/ES451020A1/es not_active Expired
- 1976-08-26 BG BG034082A patent/BG27550A3/xx unknown
- 1976-08-26 AT AT636576A patent/AT358029B/de not_active IP Right Cessation
- 1976-08-27 BE BE1007588A patent/BE845643A/xx not_active IP Right Cessation
- 1976-08-27 DD DD7600194504A patent/DD128675A5/xx unknown
- 1976-08-27 FR FR7626028A patent/FR2332011A1/fr active Granted
- 1976-08-27 ZA ZA00765143A patent/ZA765143B/xx unknown
- 1976-09-14 PL PL1976192395A patent/PL105486B1/pl unknown
- 1976-09-14 PL PL1976210940A patent/PL110781B1/pl unknown
- 1976-11-17 JP JP51139043A patent/JPS5265269A/ja active Pending
-
1977
- 1977-08-16 ES ES461632A patent/ES461632A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |