YU46059B - Postupak za dobijanje anhidropenicilinskog intermedijera - Google Patents
Postupak za dobijanje anhidropenicilinskog intermedijeraInfo
- Publication number
- YU46059B YU46059B YU134487A YU134487A YU46059B YU 46059 B YU46059 B YU 46059B YU 134487 A YU134487 A YU 134487A YU 134487 A YU134487 A YU 134487A YU 46059 B YU46059 B YU 46059B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- compound
- zinc
- temperature
- tetrahydrofuran
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 4
- 239000011701 zinc Substances 0.000 abstract 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229910001297 Zn alloy Inorganic materials 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- -1 chloro iodo Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 abstract 1
- 229910001316 Ag alloy Inorganic materials 0.000 abstract 1
- 229910000497 Amalgam Inorganic materials 0.000 abstract 1
- 229910000881 Cu alloy Inorganic materials 0.000 abstract 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 abstract 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 125000001979 organolithium group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 abstract 1
- 229910000083 tin tetrahydride Inorganic materials 0.000 abstract 1
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 abstract 1
- 150000003751 zinc Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/86—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
POSTUPAK ZA DOBIJANJE ANHIDROPENICILINSKOG INTERMEDIJERA formule: u kojoj R' predstavlja vodonik ili hidroksi-zastitnu grupu, kao sto je voluminozna triorganosilil grupa, naznacen time, sto 6,6-disupstituisani anhidropenicilin formule: u kojoj su X i Y svaki nezavisno hloro, bromo, jodo ili fenilseleno, reaguje sa reagensom koji je odabran od Grinjarovog reagensa formule R1MgX ili organolitijumovog reagensa formule R1Li, gde R1 predstavlja C1-4 alkil ili fenil, a X je kao sto je definisano gore, u anhidrovanom organskom rastvaracu kao sto je metilen hlorid, hloroform, tetrahidrofuran, dietil etar, toluol, dioksan, dimetoksietan ili njihove smese, na temperaturi od oko 0 do -78 C, nakon cega se, pod istim uslovima, vrsi adicija acet-aldehida tako da se dobija iskljucivo cis-izomer jedinjenja formule: u kojoj je X kao sto je definisano gore; sto se jedinjenje formule (IIa) podvrgava redukciji sa redukcionim sredstvom kao sto je legura cink/srebro, legura cink/bakar, kalaj jodid, kalaj hidrid, amalgam cinka, cink ili cink aktiviran kiselinom, ili se redukcija vrsi katalitickom hidrogenacijom, u inertnom rastvaracu kao sto je tetrahidrofuran, dietil etar, metanol, etanol, izopropanol, sircetna kiselina ili smese navedenih rastvaraca, na temperaturi od oko -45 C do sobne temperature, tako da se dobija jedinjenje formule (III) u kojoj R' predstavlja vodonik; i sto se, po potrebi, jedinjenje formule (III) u kojoj R' predstavlja vodonik sililuje u inertnom organskom rastvaracu kao sto je metilen hlorid, tetrahidrofuran, dioksan, dietoksimetan, hloroform ili dietil etar, u prisustvu organske baze kao sto je piridin, 2,6-lutidin, imidazol ili trietilamin i na temperaturi od oko -40 do +5 C, da bi se dobilo jedinjenje formule (III) u kojoj R' predstavlja hidroksi-zastitnu grupu kao sto je definisano gore.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU134487A YU46059B (sh) | 1984-04-06 | 1987-07-17 | Postupak za dobijanje anhidropenicilinskog intermedijera |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/597,765 US4596677A (en) | 1984-04-06 | 1984-04-06 | Anhydropenicillin intermediates |
| YU57185A YU45918B (sh) | 1984-04-06 | 1985-04-05 | Postupak za dobijanje anhidropenicilinskog intermedijera |
| YU134487A YU46059B (sh) | 1984-04-06 | 1987-07-17 | Postupak za dobijanje anhidropenicilinskog intermedijera |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU134487A YU134487A (en) | 1988-02-29 |
| YU46059B true YU46059B (sh) | 1992-12-21 |
Family
ID=24392838
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU57185A YU45918B (sh) | 1984-04-06 | 1985-04-05 | Postupak za dobijanje anhidropenicilinskog intermedijera |
| YU134487A YU46059B (sh) | 1984-04-06 | 1987-07-17 | Postupak za dobijanje anhidropenicilinskog intermedijera |
| YU134587A YU46060B (sh) | 1984-04-06 | 1987-07-17 | Postupak za dobijanje anhidropenicilinskog intermedijera |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU57185A YU45918B (sh) | 1984-04-06 | 1985-04-05 | Postupak za dobijanje anhidropenicilinskog intermedijera |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU134587A YU46060B (sh) | 1984-04-06 | 1987-07-17 | Postupak za dobijanje anhidropenicilinskog intermedijera |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US4596677A (sh) |
| JP (2) | JPS6117586A (sh) |
| KR (1) | KR920006919B1 (sh) |
| AR (1) | AR241139A1 (sh) |
| AT (1) | AT388556B (sh) |
| AU (1) | AU580043B2 (sh) |
| BE (1) | BE902133A (sh) |
| CA (1) | CA1261318A (sh) |
| CH (1) | CH665420A5 (sh) |
| CS (1) | CS253724B2 (sh) |
| CY (1) | CY1572A (sh) |
| DD (1) | DD232132A5 (sh) |
| DE (1) | DE3512250A1 (sh) |
| DK (1) | DK156085A (sh) |
| ES (1) | ES8702422A1 (sh) |
| FI (1) | FI86852C (sh) |
| FR (1) | FR2562541B1 (sh) |
| GB (1) | GB2156814B (sh) |
| GR (1) | GR850879B (sh) |
| HK (1) | HK106090A (sh) |
| HU (2) | HU193959B (sh) |
| IE (1) | IE58409B1 (sh) |
| IL (1) | IL74799A (sh) |
| IT (1) | IT1190351B (sh) |
| LU (1) | LU85841A1 (sh) |
| NL (1) | NL8500986A (sh) |
| NO (2) | NO164902C (sh) |
| NZ (1) | NZ211457A (sh) |
| OA (1) | OA07984A (sh) |
| PT (1) | PT80235B (sh) |
| SE (3) | SE466201B (sh) |
| SG (1) | SG91090G (sh) |
| SU (2) | SU1400504A3 (sh) |
| YU (3) | YU45918B (sh) |
| ZA (1) | ZA852237B (sh) |
| ZW (1) | ZW5585A1 (sh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU601180B2 (en) * | 1986-04-30 | 1990-09-06 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Process for preparing 4-acetoxy-3-hydroxyethylazetidin -2- one derivatives |
| US4876338A (en) * | 1986-07-21 | 1989-10-24 | Schering Corporation | Synthesis of azetidinones using CuCl |
| US4948885A (en) * | 1986-07-21 | 1990-08-14 | Schering-Plough Corp. | Synthesis of azetidinones |
| US5053502A (en) * | 1986-07-21 | 1991-10-01 | Schering Corporation | Anhydro penicillin derivatives |
| US4767853A (en) * | 1986-07-21 | 1988-08-30 | Schering Corporation | Synthesis of 1-(allyloxycarbonyl)-methyl-3-(hydroxyethyl)-4-beta-naphthoxythiocarbonylthio-2-azetidinones and hydroxy protected analogs thereof |
| US5075438A (en) * | 1986-07-21 | 1991-12-24 | Schering Corporation | Synthesis of azetidinones |
| EP0290385B1 (de) * | 1987-05-04 | 1992-10-21 | Ciba-Geigy Ag | Neues Verfahren zur Herstellung von 4-Acyloxy-3-hydroxyethyl-azetidinonen |
| US5274188A (en) * | 1987-05-04 | 1993-12-28 | Ciba-Geigy Corporation | Process for the manufacture of 4-acyloxy-3-hydroxyethyl-azetidinones |
| US4876365A (en) * | 1988-12-05 | 1989-10-24 | Schering Corporation | Intermediate compounds for preparing penems and carbapenems |
| ES2336677T3 (es) * | 2003-09-03 | 2010-04-15 | Otsuka Chemical Co., Ltd. | Proceso de produccion de compuestos de acido penicilanico. |
| JP5300713B2 (ja) * | 2007-03-09 | 2013-09-25 | 大塚化学株式会社 | ６−ヒドロキシエチルペナム化合物の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3311638A (en) * | 1961-08-16 | 1967-03-28 | Bristol Myers Co | Anhydropenicillins |
| US3950352A (en) * | 1972-04-10 | 1976-04-13 | Queen's University | 2,2-Dimethyl-3R-carboxy-6S-phenyl(or phenoxy)acetamido-1-oxa-4-aza-5R-bicyclo[3,2,0]heptan-7-one and processes for their production |
| SE449103B (sv) * | 1979-03-05 | 1987-04-06 | Pfizer | Sett att framstella penicillansyra-1,1-dioxid samt estrar derav |
| US4356120A (en) * | 1979-07-23 | 1982-10-26 | Merck & Co., Inc. | 3-(1-Hydroxyethyl)-4-(but-2-ene)-azetidin-2-one and derivatives |
| US4468351A (en) * | 1983-06-06 | 1984-08-28 | Pfizer Inc. | Process for debromination of dibromopenicillanic acid and derivatives |
-
1984
- 1984-04-06 US US06/597,765 patent/US4596677A/en not_active Expired - Fee Related
-
1985
- 1985-03-15 NZ NZ211457A patent/NZ211457A/xx unknown
- 1985-03-22 FR FR8504289A patent/FR2562541B1/fr not_active Expired
- 1985-03-22 CA CA000477210A patent/CA1261318A/en not_active Expired
- 1985-03-25 ZA ZA852237A patent/ZA852237B/xx unknown
- 1985-03-25 ZW ZW55/85A patent/ZW5585A1/xx unknown
- 1985-03-25 AR AR299861A patent/AR241139A1/es active
- 1985-04-01 NO NO851310A patent/NO164902C/no unknown
- 1985-04-02 FI FI851324A patent/FI86852C/fi not_active IP Right Cessation
- 1985-04-02 ES ES541866A patent/ES8702422A1/es not_active Expired
- 1985-04-02 DD DD85274771A patent/DD232132A5/de not_active IP Right Cessation
- 1985-04-03 IL IL74799A patent/IL74799A/xx unknown
- 1985-04-03 DK DK156085A patent/DK156085A/da not_active IP Right Cessation
- 1985-04-03 NL NL8500986A patent/NL8500986A/nl not_active Application Discontinuation
- 1985-04-03 SE SE8501679A patent/SE466201B/sv not_active IP Right Cessation
- 1985-04-03 DE DE19853512250 patent/DE3512250A1/de not_active Ceased
- 1985-04-04 CS CS852529A patent/CS253724B2/cs unknown
- 1985-04-04 OA OA58560A patent/OA07984A/xx unknown
- 1985-04-04 AU AU40864/85A patent/AU580043B2/en not_active Ceased
- 1985-04-04 GB GB08508847A patent/GB2156814B/en not_active Expired
- 1985-04-04 JP JP60071880A patent/JPS6117586A/ja active Granted
- 1985-04-04 IE IE86785A patent/IE58409B1/en not_active IP Right Cessation
- 1985-04-04 PT PT80235A patent/PT80235B/pt not_active IP Right Cessation
- 1985-04-04 CH CH1496/85A patent/CH665420A5/de not_active IP Right Cessation
- 1985-04-04 KR KR1019850002256A patent/KR920006919B1/ko not_active IP Right Cessation
- 1985-04-05 HU HU851289A patent/HU193959B/hu not_active IP Right Cessation
- 1985-04-05 IT IT20246/85A patent/IT1190351B/it active
- 1985-04-05 HU HU86107A patent/HU194250B/hu not_active IP Right Cessation
- 1985-04-05 BE BE0/214802A patent/BE902133A/fr not_active IP Right Cessation
- 1985-04-05 LU LU85841A patent/LU85841A1/fr unknown
- 1985-04-05 YU YU57185A patent/YU45918B/sh unknown
- 1985-04-05 SU SU853873602A patent/SU1400504A3/ru active
- 1985-04-05 AT AT0104285A patent/AT388556B/de not_active IP Right Cessation
- 1985-04-08 GR GR850879A patent/GR850879B/el unknown
- 1985-10-04 JP JP60221720A patent/JPS61171485A/ja active Granted
-
1986
- 1986-01-13 US US06/818,145 patent/US4639335A/en not_active Expired - Fee Related
- 1986-01-30 NO NO86860326A patent/NO166132C/no unknown
- 1986-06-13 SU SU864027635A patent/SU1435154A3/ru active
-
1987
- 1987-07-17 YU YU134487A patent/YU46059B/sh unknown
- 1987-07-17 YU YU134587A patent/YU46060B/sh unknown
-
1990
- 1990-03-06 SE SE9000790A patent/SE9000790L/xx not_active Application Discontinuation
- 1990-03-06 SE SE9000791A patent/SE9000791L/xx not_active Application Discontinuation
- 1990-11-09 SG SG910/90A patent/SG91090G/en unknown
- 1990-12-13 HK HK1060/90A patent/HK106090A/xx unknown
-
1991
- 1991-12-20 CY CY1572A patent/CY1572A/xx unknown
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