YU45787B - Postupak za dobijanje 3-(supstituisanih)propenilaminotiazolil-cefalosporanski kiselina i njihovih estara - Google Patents
Postupak za dobijanje 3-(supstituisanih)propenilaminotiazolil-cefalosporanski kiselina i njihovih estaraInfo
- Publication number
- YU45787B YU45787B YU110086A YU110086A YU45787B YU 45787 B YU45787 B YU 45787B YU 110086 A YU110086 A YU 110086A YU 110086 A YU110086 A YU 110086A YU 45787 B YU45787 B YU 45787B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- compound
- group
- hydrogen
- defined above
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 4
- 150000007513 acids Chemical class 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- -1 acetoxymethyl Chemical group 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 abstract 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012430 organic reaction media Substances 0.000 abstract 1
- 238000006552 photochemical reaction Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
POSTUPAK ZA DOBIJANJE 3-(SUPSTITUISANIH)PROPENILAMINOTIAZOLIL-CEFALOSPORANSKI KISELINA I NJIHOVIH ESTARA, formule: u kojima je R1 vodonik ili amino-zascitna grupa kao sto je tricil; R2 je vodonik, C1-4 alkil, C2-4 alkenil, C2-4 alkinil ili C3-6 cikloalkil grupa, cikloalkilalkil grupa sa 3-6 ugljenikovih atoma u prstenu i ukupno 4-10 ugljenikovih atoma, ili C2-4 alkanoil grupa; R3 je vodonik, C1-3 alkil ili C2-3 alkanoiloksi; i R4 je vodonik ili estarska grupa koja podleze fizioloskoj hidrolizi, kao sto je acetoksimetil, 1-acetoksietil, pivaloiloksimetil, 5-metil-2-okso-1,3-dioksolen-4-ilmetil, 1-(etoksikarboniloksi)etil ili 4-gliciloksi-benzoiloksimetil, naznacen time, sto jedinjenje formule: u kojoj R5 predstavlja grupu formule: gde je R1' amino zastitna grupa kao sto je tricil; R2a je hidroksi-zastitna grupa kao sto je tricil, hloroacetil, formil, trihloroetoksikarbonil, terc-butoksikarbonil ili karbobenziloksi, ili ima jedno od znacenja dato za R2, osim vodonika; i R4' je karboksi-zastitna grupa kao sto je difenilmetil, reaguje sa aldehidom formule: R3CH2CHO u kojoj je R3 kao sto je definisano gore, u inertnom organskom reakcionom medijumu kao sto je dihlorometan, N,N'-dimetilformamid, izopropanol ili smesa ovih rastvaraca, po potrebi u prisustvu litijum hlorida, litijum bromida ili litijum jodida, na temperaturi od oko 0 do 25 C, tako da se dobija jedinjenje formule: u kojoj su R3, R5 i R4', kao sto je definisano gore; sto se, kada R5 predstavlja grupu formule (XVI), vrsi njena selektivna hidroliza u prisustvu kiseline kao sto je HCl, na sobnoj temperaturi, nakon cega se, po potrebi, 3-(Z)-izomer dobijenog 7-amino intermedijera prevodi u 3-(E)-izomer fotohemijskom reakcijom, u rastvaracu kao sto je metanol i u prisustvu senzibilizatora kao sto je benzofenon, na sobnoj temperaturi, i zatim se 7-amino intermedijer aciluje sa jedinjenjem formule: ili njegovim aktiviranim derivatom kao sto je anhidrid ili hlorid, u rastvaracu kao sto je dihlorometan i na temperaturi od oko -10 C do sobne, da bi se dobilo jedinjenje formule: pri cemu su R3, R1', R2a i R4' kao sto je definisano gore; sto se u jedinjenju formule (XIX) uklanjaju zastitne grupe R1, R2a i R4' reakcijom sa kiselinom, kao sto je trifluorosircetna kiselina, po potrebi u prisustvu anizola, i sto se, po potrebi, vrsi odvajanje 3-(Z)- i 3-(E)-izomera, da bi se dobilo jedinjenje formule: u kojoj su R1, R2 i R3 kao sto je definisano gore; i sto, po potrebi, alkalnometalna ili amonijumova so jedinjenja formule (Ia) reaguje sa halogenidom formule: R4b-X u kojoj X predstavlja hloro, bromo ili jodo, a R4b je estarska grupa koja podleze fizioloskoj hidrolizi, kao sto je acetoksimetil, 1-acetoksietil, pivaloiloksimetil, 5-metil-2-okso-1,3-dioksolen-4-ilmetil, 1-(etoksikarboniloksi)etil ili 4-gliciloksibenzoiloksimetil, da bi se dobio estar formule: u kojoj R4 ima znacenje kao sto je definisano gore, razlicito od vodonika.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/748,359 US4708955A (en) | 1985-06-24 | 1985-06-24 | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU110086A YU110086A (en) | 1987-10-31 |
| YU45787B true YU45787B (sh) | 1992-07-20 |
Family
ID=25009129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU110086A YU45787B (sh) | 1985-06-24 | 1986-06-24 | Postupak za dobijanje 3-(supstituisanih)propenilaminotiazolil-cefalosporanski kiselina i njihovih estara |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US4708955A (sh) |
| JP (1) | JPS62491A (sh) |
| KR (1) | KR930007416B1 (sh) |
| AR (1) | AR244233A1 (sh) |
| AT (1) | AT390956B (sh) |
| AU (1) | AU593557B2 (sh) |
| BE (1) | BE904983A (sh) |
| CA (1) | CA1279868C (sh) |
| CS (1) | CS258142B2 (sh) |
| CY (1) | CY1618A (sh) |
| DD (1) | DD246112A5 (sh) |
| DE (1) | DE3620995A1 (sh) |
| DK (1) | DK295386A (sh) |
| EG (1) | EG17868A (sh) |
| ES (1) | ES8800680A1 (sh) |
| FI (1) | FI85487C (sh) |
| FR (1) | FR2583757B1 (sh) |
| GB (1) | GB2178032B (sh) |
| GR (1) | GR861611B (sh) |
| HK (1) | HK106091A (sh) |
| HU (1) | HU199484B (sh) |
| IE (1) | IE59123B1 (sh) |
| IL (1) | IL79181A0 (sh) |
| IT (1) | IT1221767B (sh) |
| LU (1) | LU86488A1 (sh) |
| MY (1) | MY102073A (sh) |
| NL (1) | NL8601645A (sh) |
| NZ (1) | NZ216614A (sh) |
| OA (1) | OA08349A (sh) |
| PH (2) | PH21206A (sh) |
| PT (1) | PT82836B (sh) |
| SE (1) | SE500218C2 (sh) |
| SG (1) | SG91691G (sh) |
| SU (1) | SU1428204A3 (sh) |
| YU (1) | YU45787B (sh) |
| ZA (1) | ZA864297B (sh) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4874856A (en) * | 1985-06-24 | 1989-10-17 | Bristol-Myers Company | 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof |
| GB8519606D0 (en) * | 1985-08-05 | 1985-09-11 | Fujisawa Pharmaceutical Co | 3 7-d substituted-3-cephem compounds |
| US4870168A (en) * | 1987-02-26 | 1989-09-26 | Bristol-Myers Company | 3-Unsaturated alkyl cephems from 3-triflyl cephems |
| FR2622585B1 (fr) * | 1987-11-03 | 1991-04-19 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 3 un radical vinyle substitue, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
| US4935508A (en) * | 1988-08-23 | 1990-06-19 | Bristol-Myers Company | Process for cephem prodrug esters |
| US5143911A (en) * | 1990-08-23 | 1992-09-01 | Bristol-Myers Squibb Company | Antibiotic c-3 di-hydroxyphenyl substituted cephalosporin compounds, compositions and method of use thereof |
| JP2825655B2 (ja) * | 1992-02-05 | 1998-11-18 | バイオケミ・ゲゼルシヤフト・エム・ベー・ハー | ３−セフェム−４−カルボン酸誘導体の精製方法 |
| JPH07173168A (ja) * | 1993-07-14 | 1995-07-11 | Sumitomo Chem Co Ltd | セフェム系化合物、その製法、およびそれのセフェム系抗生物質製造への利用 |
| KR100408430B1 (ko) * | 2001-04-18 | 2003-12-06 | 한미약품 주식회사 | 3-(ｚ)-프로페닐 세펨 화합물의 선택적인 제조 방법 |
| US7544797B2 (en) * | 2003-10-30 | 2009-06-09 | Cj Cheiljedang Corporation | Processes for the preparation of cephem derivatives |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917778A (en) * | 1968-04-13 | 1975-11-04 | Tdk Electronics Co Ltd | Method for slip casting soft ferromagnetic ferrites |
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| US4065620A (en) * | 1971-06-14 | 1977-12-27 | Eli Lilly And Company | 3-(Substituted) vinyl cephalosporins |
| FR2345153A1 (fr) * | 1976-03-25 | 1977-10-21 | Roussel Uclaf | Nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| US4464369A (en) * | 1977-03-14 | 1984-08-07 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-cephem-4-carboxylic acid derivatives and pharmaceutical compositions |
| FR2457296A1 (fr) * | 1979-05-23 | 1980-12-19 | Rhone Poulenc Ind | Nouveaux derives de vinyl-3 cephalosporines et leur preparation |
| CA1145744A (fr) * | 1979-05-23 | 1983-05-03 | Daniel Farge | Thiovinyl-3 cephalosporines, leur preparation et les compositions qui les contiennent |
| FR2457297A1 (fr) * | 1979-05-23 | 1980-12-19 | Rhone Poulenc Ind | Nouvelles vinyl-3 cephalosporines, et leur preparation |
| US4409214A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| FR2494276A2 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles vinyl-3 cephalosporines, et leur preparation |
| FR2494280A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouveaux derives de la cephalosporine et leur preparation |
| FR2494275A2 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouveaux derives de vinyl-3 cephalosporines et leur preparation |
| IE53429B1 (en) * | 1981-08-03 | 1988-11-09 | Fujisawa Pharmaceutical Co | New cephem compounds and processes for preparation thereof |
| DK162718C (da) * | 1982-09-30 | 1992-05-11 | Fujisawa Pharmaceutical Co | Analogifremgangsmaade til fremstilling af 7-substitueret-3-vinyl-3-cephemforbindelser |
| GB8323034D0 (en) * | 1983-08-26 | 1983-09-28 | Fujisawo Pharmaceutical Co Ltd | 7-substituted-3-vinyl-3-cephem compounds |
| US4520022A (en) * | 1983-01-28 | 1985-05-28 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
| CA1276929C (en) * | 1984-04-09 | 1990-11-27 | Masahisa Oka | Cephalosporin antibacterial agents |
| GB8411954D0 (en) * | 1984-05-10 | 1984-06-13 | Glaxo Group Ltd | Cephalosporin antibiotics |
| FR2580652B1 (fr) * | 1985-04-22 | 1989-01-06 | Bristol Myers Co | Acide 7-amino-3-propenylcephalosporanique et ses esters |
-
1985
- 1985-06-24 US US06/748,359 patent/US4708955A/en not_active Expired - Fee Related
-
1986
- 1986-06-09 ZA ZA864297A patent/ZA864297B/xx unknown
- 1986-06-17 CA CA000511752A patent/CA1279868C/en not_active Expired - Fee Related
- 1986-06-18 AU AU58821/86A patent/AU593557B2/en not_active Ceased
- 1986-06-19 FI FI862642A patent/FI85487C/fi not_active IP Right Cessation
- 1986-06-20 GR GR861611A patent/GR861611B/el unknown
- 1986-06-20 NZ NZ216614A patent/NZ216614A/xx unknown
- 1986-06-20 IL IL79181A patent/IL79181A0/xx not_active IP Right Cessation
- 1986-06-23 CS CS864624A patent/CS258142B2/cs unknown
- 1986-06-23 ES ES556465A patent/ES8800680A1/es not_active Expired
- 1986-06-23 HU HU862625A patent/HU199484B/hu not_active IP Right Cessation
- 1986-06-23 DE DE19863620995 patent/DE3620995A1/de not_active Ceased
- 1986-06-23 SE SE8602780A patent/SE500218C2/sv unknown
- 1986-06-23 FR FR8609019A patent/FR2583757B1/fr not_active Expired
- 1986-06-23 BE BE0/216826A patent/BE904983A/fr not_active IP Right Cessation
- 1986-06-23 SU SU864027736A patent/SU1428204A3/ru active
- 1986-06-23 IE IE167086A patent/IE59123B1/en not_active IP Right Cessation
- 1986-06-23 DK DK295386A patent/DK295386A/da not_active Application Discontinuation
- 1986-06-23 PH PH33929A patent/PH21206A/en unknown
- 1986-06-23 GB GB8615253A patent/GB2178032B/en not_active Expired
- 1986-06-24 NL NL8601645A patent/NL8601645A/xx not_active Application Discontinuation
- 1986-06-24 AR AR86304352A patent/AR244233A1/es active
- 1986-06-24 IT IT20894/86A patent/IT1221767B/it active
- 1986-06-24 DD DD86291615A patent/DD246112A5/de not_active IP Right Cessation
- 1986-06-24 LU LU86488A patent/LU86488A1/fr unknown
- 1986-06-24 AT AT0171986A patent/AT390956B/de not_active IP Right Cessation
- 1986-06-24 EG EG383/86A patent/EG17868A/xx active
- 1986-06-24 OA OA58884A patent/OA08349A/xx unknown
- 1986-06-24 PT PT82836A patent/PT82836B/pt not_active IP Right Cessation
- 1986-06-24 JP JP61148005A patent/JPS62491A/ja active Pending
- 1986-06-24 KR KR1019860005028A patent/KR930007416B1/ko not_active IP Right Cessation
- 1986-06-24 YU YU110086A patent/YU45787B/sh unknown
- 1986-11-21 PH PH34510A patent/PH21879A/en unknown
-
1987
- 1987-09-29 MY MYPI87002189A patent/MY102073A/en unknown
-
1991
- 1991-11-01 SG SG916/91A patent/SG91691G/en unknown
- 1991-12-23 HK HK1060/91A patent/HK106091A/xx unknown
-
1992
- 1992-07-10 CY CY1618A patent/CY1618A/xx unknown
Also Published As
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