CS214691B2 - Method of making the vindesine - Google Patents
Method of making the vindesine Download PDFInfo
- Publication number
- CS214691B2 CS214691B2 CS80235A CS23580A CS214691B2 CS 214691 B2 CS214691 B2 CS 214691B2 CS 80235 A CS80235 A CS 80235A CS 23580 A CS23580 A CS 23580A CS 214691 B2 CS214691 B2 CS 214691B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- vindesine
- triphenylphosphine
- solution
- tetrahydrofuran
- vlb
- Prior art date
Links
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229960004355 vindesine Drugs 0.000 title claims abstract description 34
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003637 basic solution Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- RVCKCEDKBVEEHL-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzyl alcohol Chemical compound OCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl RVCKCEDKBVEEHL-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- -1 acyl iminophosphorane Chemical compound 0.000 abstract description 2
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 10
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 8
- 150000001540 azides Chemical class 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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 Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229960004528 vincristine Drugs 0.000 description 2
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 2
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 2
- LVAFECUUEHXVBF-UHFFFAOYSA-N (+)-Velbanamine Natural products C1C(CC)(O)CC(CC2)CN1CCC1=C2NC2=CC=CC=C12 LVAFECUUEHXVBF-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 240000001829 Catharanthus roseus Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 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
- WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LHUZAYREVYDAGJ-UHFFFAOYSA-N dichloromethane;ethyl acetate;methanol Chemical compound OC.ClCCl.CCOC(C)=O LHUZAYREVYDAGJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 201000000966 lung oat cell carcinoma Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940005654 nitrite ion Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000174 oncolytic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WTLOGKMDQWEFOK-UHFFFAOYSA-N oxolane;triphenylphosphane Chemical compound C1CCOC1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WTLOGKMDQWEFOK-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000000649 small cell carcinoma Diseases 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 101150020850 velB gene Proteins 0.000 description 1
- KGKWFGPHYYEERW-UHFFFAOYSA-N velbanamine Chemical compound C1CC2(C(C3)C(O)=O)N(C(=O)OC)C4=CC=CC=C4C22C4C31CCCN4CC2 KGKWFGPHYYEERW-UHFFFAOYSA-N 0.000 description 1
- CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/003,442 US4210584A (en) | 1979-01-15 | 1979-01-15 | Vindesine synthesis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214691B2 true CS214691B2 (en) | 1982-05-28 |
Family
ID=21705894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS80235A CS214691B2 (en) | 1979-01-15 | 1980-01-10 | Method of making the vindesine |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4210584A (ko) |
| EP (1) | EP0014053B1 (ko) |
| JP (1) | JPS5598195A (ko) |
| KR (1) | KR830002840B1 (ko) |
| AR (1) | AR223694A1 (ko) |
| AT (1) | AT371127B (ko) |
| AU (1) | AU5452280A (ko) |
| BE (1) | BE881078A (ko) |
| BG (1) | BG33295A3 (ko) |
| CA (1) | CA1148945A (ko) |
| CH (1) | CH645383A5 (ko) |
| CS (1) | CS214691B2 (ko) |
| DD (1) | DD148779A5 (ko) |
| DE (1) | DE3065852D1 (ko) |
| DK (1) | DK148961C (ko) |
| ES (2) | ES487682A0 (ko) |
| FI (1) | FI800071A (ko) |
| FR (1) | FR2446290A1 (ko) |
| GB (1) | GB2040934B (ko) |
| GR (1) | GR72464B (ko) |
| HU (1) | HU182083B (ko) |
| IE (1) | IE49376B1 (ko) |
| IL (1) | IL59119A (ko) |
| IT (1) | IT1140506B (ko) |
| LU (1) | LU82079A1 (ko) |
| MY (1) | MY8500570A (ko) |
| NZ (1) | NZ192574A (ko) |
| PH (1) | PH15343A (ko) |
| PL (1) | PL124350B1 (ko) |
| PT (1) | PT70681A (ko) |
| RO (1) | RO77532A (ko) |
| SU (1) | SU906381A3 (ko) |
| YU (1) | YU5680A (ko) |
| ZA (1) | ZA80157B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60112895A (ja) * | 1983-11-24 | 1985-06-19 | Nippon Oil & Fats Co Ltd | 金属圧延用潤滑油 |
| FR2651348B1 (ko) * | 1989-08-04 | 1993-01-22 | Adir | |
| TW258739B (ko) * | 1992-04-04 | 1995-10-01 | Hoechst Ag | |
| EP1235598A2 (en) * | 1999-11-12 | 2002-09-04 | Angiotech Pharmaceuticals, Inc. | Compositions of a combination of radioactive therapy and cell-cycle inhibitors |
| WO2004060346A2 (en) | 2002-12-30 | 2004-07-22 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
| CN106831826B (zh) * | 2016-12-31 | 2018-07-06 | 广州白云山汉方现代药业有限公司 | 一种从长春花中制备长春地辛的方法 |
| CN106831827B (zh) * | 2016-12-31 | 2019-03-29 | 广州白云山汉方现代药业有限公司 | 一种长春地辛的分离纯化方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756235A (en) * | 1954-08-27 | 1956-07-24 | Lilly Co Eli | Method of producing lysergic acid amide |
-
1979
- 1979-01-15 US US06/003,442 patent/US4210584A/en not_active Expired - Lifetime
-
1980
- 1980-01-10 FI FI800071A patent/FI800071A/fi not_active Application Discontinuation
- 1980-01-10 CA CA000343455A patent/CA1148945A/en not_active Expired
- 1980-01-10 GB GB8000870A patent/GB2040934B/en not_active Expired
- 1980-01-10 NZ NZ192574A patent/NZ192574A/xx unknown
- 1980-01-10 ZA ZA00800157A patent/ZA80157B/xx unknown
- 1980-01-10 EP EP80300095A patent/EP0014053B1/en not_active Expired
- 1980-01-10 PT PT70681A patent/PT70681A/pt unknown
- 1980-01-10 AU AU54522/80A patent/AU5452280A/en not_active Abandoned
- 1980-01-10 CS CS80235A patent/CS214691B2/cs unknown
- 1980-01-10 YU YU00056/80A patent/YU5680A/xx unknown
- 1980-01-10 BE BE1/9677A patent/BE881078A/fr not_active IP Right Cessation
- 1980-01-10 DE DE8080300095T patent/DE3065852D1/de not_active Expired
- 1980-01-10 FR FR8000466A patent/FR2446290A1/fr active Granted
- 1980-01-10 GR GR60929A patent/GR72464B/el unknown
- 1980-01-11 HU HU8052A patent/HU182083B/hu not_active IP Right Cessation
- 1980-01-11 JP JP250480A patent/JPS5598195A/ja active Granted
- 1980-01-11 AT AT0014080A patent/AT371127B/de not_active IP Right Cessation
- 1980-01-13 IL IL59119A patent/IL59119A/xx unknown
- 1980-01-14 PL PL1980221359A patent/PL124350B1/pl unknown
- 1980-01-14 DK DK14780A patent/DK148961C/da not_active IP Right Cessation
- 1980-01-14 IE IE60/80A patent/IE49376B1/en unknown
- 1980-01-14 PH PH23506A patent/PH15343A/en unknown
- 1980-01-14 AR AR279615A patent/AR223694A1/es active
- 1980-01-14 IT IT19210/80A patent/IT1140506B/it active
- 1980-01-14 ES ES487682A patent/ES487682A0/es active Granted
- 1980-01-14 LU LU82079A patent/LU82079A1/fr unknown
- 1980-01-14 CH CH28780A patent/CH645383A5/fr not_active IP Right Cessation
- 1980-01-14 BG BG046233A patent/BG33295A3/xx unknown
- 1980-01-14 SU SU802872553A patent/SU906381A3/ru active
- 1980-01-15 ES ES487726A patent/ES8101612A1/es not_active Expired
- 1980-01-15 DD DD80218466A patent/DD148779A5/de unknown
- 1980-01-15 RO RO8099874A patent/RO77532A/ro unknown
- 1980-01-15 KR KR1019800000134A patent/KR830002840B1/ko active
-
1985
- 1985-12-30 MY MY570/85A patent/MY8500570A/xx unknown
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