SE463263B - Foerfarande foer framstaellning av kristallin cefuroxim-1-acetoxietylester - Google Patents
Foerfarande foer framstaellning av kristallin cefuroxim-1-acetoxietylesterInfo
- Publication number
- SE463263B SE463263B SE8403897A SE8403897A SE463263B SE 463263 B SE463263 B SE 463263B SE 8403897 A SE8403897 A SE 8403897A SE 8403897 A SE8403897 A SE 8403897A SE 463263 B SE463263 B SE 463263B
- Authority
- SE
- Sweden
- Prior art keywords
- cefuroxime
- crystalline
- minutes
- stirred
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 49
- KEJCWVGMRLCZQQ-YJBYXUATSA-N Cefuroxime axetil Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(=O)OC(C)OC(C)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 KEJCWVGMRLCZQQ-YJBYXUATSA-N 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229960002620 cefuroxime axetil Drugs 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- URDOHUPGIOGTKV-JTBFTWTJSA-M Cefuroxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 URDOHUPGIOGTKV-JTBFTWTJSA-M 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960001668 cefuroxime Drugs 0.000 description 6
- JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- -1 1-acetoxyethyl group Chemical group 0.000 description 5
- IIASCQBFNHWZBE-UHFFFAOYSA-N 1-bromoethyl acetate Chemical compound CC(Br)OC(C)=O IIASCQBFNHWZBE-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 239000003344 environmental pollutant Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 231100000719 pollutant Toxicity 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 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
- C07D501/24—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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero 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
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838320521A GB8320521D0 (en) | 1983-07-29 | 1983-07-29 | Chemical process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8403897D0 SE8403897D0 (sv) | 1984-07-27 |
| SE8403897L SE8403897L (sv) | 1985-01-30 |
| SE463263B true SE463263B (sv) | 1990-10-29 |
Family
ID=10546505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8403897A SE463263B (sv) | 1983-07-29 | 1984-07-27 | Foerfarande foer framstaellning av kristallin cefuroxim-1-acetoxietylester |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPH0613526B2 (de) |
| KR (1) | KR910008377B1 (de) |
| AT (1) | AT392470B (de) |
| AU (2) | AU582121B2 (de) |
| BE (1) | BE900241A (de) |
| CA (1) | CA1265511A (de) |
| CH (1) | CH662121A5 (de) |
| DE (1) | DE3427828A1 (de) |
| DK (1) | DK165505C (de) |
| ES (1) | ES534695A0 (de) |
| FI (1) | FI76808C (de) |
| FR (1) | FR2549837B1 (de) |
| GB (2) | GB8320521D0 (de) |
| IE (1) | IE57726B1 (de) |
| IL (1) | IL72536A (de) |
| NL (1) | NL8402372A (de) |
| NO (1) | NO167292C (de) |
| NZ (1) | NZ209046A (de) |
| PT (1) | PT78985B (de) |
| SE (1) | SE463263B (de) |
| ZA (1) | ZA845830B (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8400024D0 (en) * | 1984-01-03 | 1984-02-08 | Glaxo Group Ltd | Cephalosporin antibiotics |
| GB8524001D0 (en) * | 1985-09-30 | 1985-11-06 | Glaxo Group Ltd | Pharmaceutical composition |
| US5063224A (en) * | 1990-07-09 | 1991-11-05 | Eli Lilly And Company | R-cefuroxime axetil |
| IT1277426B1 (it) * | 1995-08-03 | 1997-11-10 | Acs Dobfar Spa | Forma cristallina biodisponibile del cefuroxima axetil |
| CN1111537C (zh) * | 1997-05-15 | 2003-06-18 | 第一制糖株式会社 | 高纯晶形头孢呋辛1－乙酰氧乙酯的制备方法 |
| KR100228264B1 (ko) * | 1997-08-02 | 1999-11-01 | 김선진 | 결정형 세푸록심 악세틸의 제조방법 |
| CA2209868C (en) * | 1997-08-15 | 2001-08-14 | Bernard Charles Sherman | Pharmaceutical compositions comprising cefuroxime axetil |
| IN186539B (de) * | 1997-09-29 | 2001-09-29 | Ranbaxy Lab Ltd | |
| ES2171056T3 (es) * | 1998-02-20 | 2002-08-16 | Fako Ilaclari A S | Procedimiento para la fabricacion de cefuroxima axetil cristalina soluble. |
| IN190849B (de) | 2000-07-17 | 2003-08-23 | Ranbaxy Lab Ltd | |
| AT411996B (de) | 2000-09-11 | 2004-08-26 | Sandoz Ag | Verfahren zur herstellung von cefuroxim in der form seines n-butylammoniumsalzes |
| ITMI20011763A1 (it) * | 2001-08-10 | 2003-02-10 | Antibioticos Spa | Processo di preparazione di cefuroxime axelite ad elevata purezza |
| ITMI20011925A1 (it) * | 2001-09-14 | 2003-03-14 | Antibioticos Spa | Metodo applicabile su scala industriale per la preparazione di cefuroxime axetile cristallino |
| TWI328006B (en) * | 2003-12-26 | 2010-08-01 | Nissan Chemical Ind Ltd | Crystal form of quinoline compound and process for its production |
| CN100448879C (zh) * | 2004-07-22 | 2009-01-07 | 北京化工大学 | 一种无定型头孢呋辛酯的制备方法 |
| DE102005019458A1 (de) * | 2005-04-25 | 2006-10-26 | Grünenthal GmbH | Darreichungsform mit verbesserter Freisetzung von Cefuroximaxetil |
| CN118561870A (zh) * | 2024-05-15 | 2024-08-30 | 广东立国制药有限公司 | 一种制备头孢呋辛酸的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1094545A (en) * | 1976-02-16 | 1981-01-27 | Michael Gregson | Cephalosporin antibiotics |
| GB1571683A (en) * | 1976-02-16 | 1980-07-16 | Glaxo Operations Ltd | Ester derivatives of cefuroxime |
| GB1598568A (en) * | 1977-04-19 | 1981-09-23 | Glaxo Lab Ltd | Esters of(6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-2-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid |
| JPS577485A (en) * | 1980-06-13 | 1982-01-14 | Takeda Chem Ind Ltd | Cephalosporin |
| YU44680B (en) * | 1982-07-30 | 1990-12-31 | Glaxo Lab Ltd | Process for obtaining very pure amorphous form of cephuroxim axetile |
| GB8400024D0 (en) * | 1984-01-03 | 1984-02-08 | Glaxo Group Ltd | Cephalosporin antibiotics |
-
1983
- 1983-07-29 GB GB838320521A patent/GB8320521D0/en active Pending
-
1984
- 1984-07-27 ES ES534695A patent/ES534695A0/es active Granted
- 1984-07-27 IE IE1938/84A patent/IE57726B1/en not_active IP Right Cessation
- 1984-07-27 AU AU31256/84A patent/AU582121B2/en not_active Ceased
- 1984-07-27 DK DK366684A patent/DK165505C/da not_active IP Right Cessation
- 1984-07-27 CA CA000459929A patent/CA1265511A/en not_active Expired - Fee Related
- 1984-07-27 NL NL8402372A patent/NL8402372A/nl not_active Application Discontinuation
- 1984-07-27 GB GB08419202A patent/GB2145409B/en not_active Expired
- 1984-07-27 ZA ZA845830A patent/ZA845830B/xx unknown
- 1984-07-27 PT PT78985A patent/PT78985B/pt unknown
- 1984-07-27 BE BE0/213398A patent/BE900241A/fr not_active IP Right Cessation
- 1984-07-27 FR FR8412011A patent/FR2549837B1/fr not_active Expired
- 1984-07-27 JP JP59155694A patent/JPH0613526B2/ja not_active Expired - Lifetime
- 1984-07-27 FI FI843011A patent/FI76808C/fi not_active IP Right Cessation
- 1984-07-27 CH CH3672/84A patent/CH662121A5/de not_active IP Right Cessation
- 1984-07-27 NO NO843055A patent/NO167292C/no not_active IP Right Cessation
- 1984-07-27 DE DE19843427828 patent/DE3427828A1/de not_active Ceased
- 1984-07-27 KR KR1019840004465A patent/KR910008377B1/ko not_active Expired
- 1984-07-27 SE SE8403897A patent/SE463263B/sv not_active IP Right Cessation
- 1984-07-27 AT AT2444/84A patent/AT392470B/de not_active IP Right Cessation
- 1984-07-29 IL IL72536A patent/IL72536A/xx not_active IP Right Cessation
- 1984-07-30 NZ NZ209046A patent/NZ209046A/en unknown
-
1989
- 1989-06-16 AU AU36601/89A patent/AU634965B2/en not_active Ceased
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