FI114632B - Uusi menetelmä 4-amino-5-hekseenihapon valmistamiseksi ja siinä tuotetut välituotteet - Google Patents
Uusi menetelmä 4-amino-5-hekseenihapon valmistamiseksi ja siinä tuotetut välituotteet Download PDFInfo
- Publication number
- FI114632B FI114632B FI925592A FI925592A FI114632B FI 114632 B FI114632 B FI 114632B FI 925592 A FI925592 A FI 925592A FI 925592 A FI925592 A FI 925592A FI 114632 B FI114632 B FI 114632B
- Authority
- FI
- Finland
- Prior art keywords
- ethyl
- hexenoate
- amino
- formyloxy
- hexenoic acid
- Prior art date
Links
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 9
- 239000000543 intermediate Substances 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 7
- DLPNYKZTMBRGLC-UHFFFAOYSA-N 2-hydroxybut-3-enyl formate Chemical compound C=CC(O)COC=O DLPNYKZTMBRGLC-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000004386 Erythritol Substances 0.000 claims description 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 4
- 229940009714 erythritol Drugs 0.000 claims description 4
- 235000019414 erythritol Nutrition 0.000 claims description 4
- NKTXPLUMJAFZLC-UHFFFAOYSA-N ethyl 4-[(2,2,2-trichloroacetyl)amino]hex-5-enoate Chemical compound CCOC(=O)CCC(C=C)NC(=O)C(Cl)(Cl)Cl NKTXPLUMJAFZLC-UHFFFAOYSA-N 0.000 claims description 4
- JLIXDVYXSMNNOY-UHFFFAOYSA-N ethyl 6-formyloxyhex-4-enoate Chemical compound CCOC(=O)CCC=CCOC=O JLIXDVYXSMNNOY-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- AGGDACKPJYQQTJ-UHFFFAOYSA-N ethyl 6-hydroxyhex-4-enoate Chemical compound CCOC(=O)CCC=CCO AGGDACKPJYQQTJ-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 238000006462 rearrangement reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 102100035923 4-aminobutyrate aminotransferase, mitochondrial Human genes 0.000 description 1
- 101710115046 4-aminobutyrate aminotransferase, mitochondrial Proteins 0.000 description 1
- ROFNJLCLYMMXCT-UHFFFAOYSA-N 4-aminohexanoic acid Chemical compound CCC(N)CCC(O)=O ROFNJLCLYMMXCT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 238000005617 Overman rearrangement reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- SIIVGPQREKVCOP-UHFFFAOYSA-N but-1-en-1-ol Chemical compound CCC=CO SIIVGPQREKVCOP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229940106773 sabril Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- 229960005318 vigabatrin Drugs 0.000 description 1
- -1 vinyl GABA Chemical compound 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/24—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
- C07C227/20—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP91403351A EP0546230A1 (en) | 1991-12-10 | 1991-12-10 | Novel process for preparing 4-amino-5-hexenoic acid |
| EP91403351 | 1991-12-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI925592A0 FI925592A0 (fi) | 1992-12-09 |
| FI925592A FI925592A (fi) | 1993-06-11 |
| FI114632B true FI114632B (fi) | 2004-11-30 |
Family
ID=8208648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI925592A FI114632B (fi) | 1991-12-10 | 1992-12-09 | Uusi menetelmä 4-amino-5-hekseenihapon valmistamiseksi ja siinä tuotetut välituotteet |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US5380936A (es) |
| EP (3) | EP0546230A1 (es) |
| JP (1) | JP3229408B2 (es) |
| KR (2) | KR100248550B1 (es) |
| AR (1) | AR247723A1 (es) |
| AT (2) | ATE151070T1 (es) |
| AU (1) | AU658699B2 (es) |
| CA (1) | CA2084109C (es) |
| DE (2) | DE69218736T2 (es) |
| DK (2) | DK0546906T3 (es) |
| ES (2) | ES2102482T3 (es) |
| FI (1) | FI114632B (es) |
| GR (2) | GR3023608T3 (es) |
| HU (2) | HU213374B (es) |
| IL (5) | IL116968A (es) |
| NO (1) | NO300731B1 (es) |
| NZ (1) | NZ245398A (es) |
| TW (1) | TW224086B (es) |
| ZA (1) | ZA929443B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009046452A (ja) | 2007-08-22 | 2009-03-05 | Erick M Carreira | ホスホルアミダイト配位子およびそれを用いたアリルアミンの製造方法 |
| US20100218571A1 (en) * | 2009-03-02 | 2010-09-02 | Todd Basche | Combination lock assemblies and methods for marking combination lock assemblies including distributions of consonants and vowels |
| WO2010101952A1 (en) * | 2009-03-02 | 2010-09-10 | Wordlock, Inc. | Combination lock assemblies and methods for making combination lock assemblies including random selection of characters |
| EP2537827B1 (en) | 2011-06-24 | 2014-06-11 | Targeon SAS | Process for preparing 4-amino-5-hexenoic acid from succinimide |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US31980A (en) * | 1861-04-09 | Duane hull | ||
| US3879448A (en) * | 1970-02-07 | 1975-04-22 | Takeda Chemical Industries Ltd | 4-hexenoic compounds |
| FR2085653B1 (es) * | 1970-04-30 | 1973-06-08 | Roussel Uclaf | |
| US3960927A (en) * | 1975-03-18 | 1976-06-01 | Richardson-Merrell Inc. | Olefinic derivatives of amino acids |
| USRE31980E (en) * | 1975-03-18 | 1985-09-03 | Merrell Toraude Et Compagnie | Olefinic derivatives of amino acids |
| US4039549A (en) * | 1975-03-18 | 1977-08-02 | Merrell Toraude Et Compagnie | Olefinic derivatives of amino acids |
| US4178463A (en) * | 1978-01-30 | 1979-12-11 | Merrell Toraude Et Compagnie | Process for making 4-aminohex-5-enoic acid |
| US4672140A (en) * | 1981-01-02 | 1987-06-09 | Monsanto Company | Acyloxyalkenoic acids and process therefor |
| US4692538A (en) * | 1982-04-14 | 1987-09-08 | Bristol-Myers Company | Trichloroethanimidic acid esters |
| GB2133002B (en) * | 1982-12-30 | 1986-01-29 | Merrell Toraude & Co | Process for preparing 4-amino-5-hexenoic acid |
| US4912232A (en) * | 1983-10-14 | 1990-03-27 | Dow Chemical Company | Preparation of N-hydrocarbylcarbonyl-5-(1-hydrocarbylcarbonyloxy)hydrocarbyl-pyrrolidin-2-one |
| DE3568771D1 (en) * | 1984-10-10 | 1989-04-20 | Givaudan & Cie Sa | Hexanoates, process for their preparation and perfumes and/or flavouring agents having a content of such compounds |
| EP0258183B1 (de) * | 1986-08-13 | 1993-03-17 | Ciba-Geigy Ag | Verfahren zur Herstellung von 5-Amino-4-hydroxyvaleriansäure-Derivaten |
| YU48319B (sh) * | 1988-08-01 | 1998-05-15 | Monsanto Company | Bezbednosni herbicidni derivati benzoeve kiseline |
| CA2028782C (en) * | 1989-11-07 | 2003-10-14 | Christian T. Goralski | Process for the production of vinyl-gaba |
| DE4010709A1 (de) * | 1990-04-03 | 1991-10-10 | Huels Chemische Werke Ag | Verfahren zur herstellung von 3-carboxamido-5-vinyl-2-pyrrolidon |
| JPH0692903A (ja) * | 1992-09-09 | 1994-04-05 | Yuki Gosei Kogyo Co Ltd | ５−ホルミルオキシ−３−ペンテン酸またはそのエステルおよびその製造法 |
-
1991
- 1991-12-10 EP EP91403351A patent/EP0546230A1/en not_active Withdrawn
-
1992
- 1992-11-30 CA CA002084109A patent/CA2084109C/en not_active Expired - Lifetime
- 1992-12-04 ZA ZA929443A patent/ZA929443B/xx unknown
- 1992-12-04 AU AU29886/92A patent/AU658699B2/en not_active Expired
- 1992-12-07 IL IL11696892A patent/IL116968A/en not_active IP Right Cessation
- 1992-12-07 EP EP92403296A patent/EP0546906B1/en not_active Expired - Lifetime
- 1992-12-07 IL IL11696792A patent/IL116967A/xx not_active IP Right Cessation
- 1992-12-07 DK DK92403296.4T patent/DK0546906T3/da active
- 1992-12-07 IL IL11696896A patent/IL116968A0/xx unknown
- 1992-12-07 DE DE69218736T patent/DE69218736T2/de not_active Expired - Lifetime
- 1992-12-07 DK DK96200414.9T patent/DK0718273T3/da active
- 1992-12-07 AT AT92403296T patent/ATE151070T1/de active
- 1992-12-07 AT AT96200414T patent/ATE163916T1/de active
- 1992-12-07 ES ES92403296T patent/ES2102482T3/es not_active Expired - Lifetime
- 1992-12-07 ES ES96200414T patent/ES2116130T3/es not_active Expired - Lifetime
- 1992-12-07 TW TW081109783A patent/TW224086B/zh not_active IP Right Cessation
- 1992-12-07 DE DE69224760T patent/DE69224760T2/de not_active Expired - Lifetime
- 1992-12-07 IL IL104013A patent/IL104013A/xx not_active IP Right Cessation
- 1992-12-07 JP JP35107892A patent/JP3229408B2/ja not_active Expired - Lifetime
- 1992-12-07 EP EP96200414A patent/EP0718273B1/en not_active Expired - Lifetime
- 1992-12-08 NZ NZ24539892A patent/NZ245398A/en unknown
- 1992-12-08 KR KR1019920023550A patent/KR100248550B1/ko not_active IP Right Cessation
- 1992-12-09 HU HU9203897A patent/HU213374B/hu unknown
- 1992-12-09 FI FI925592A patent/FI114632B/fi not_active IP Right Cessation
- 1992-12-09 HU HU9203897A patent/HU9203897D0/hu unknown
- 1992-12-09 AR AR92323844A patent/AR247723A1/es active
- 1992-12-09 NO NO924763A patent/NO300731B1/no not_active IP Right Cessation
-
1994
- 1994-01-19 US US08/184,762 patent/US5380936A/en not_active Expired - Lifetime
- 1994-07-22 US US08/279,620 patent/US5440065A/en not_active Expired - Lifetime
-
1995
- 1995-04-11 US US08/420,178 patent/US5473099A/en not_active Expired - Fee Related
- 1995-04-11 US US08/420,179 patent/US5512698A/en not_active Expired - Fee Related
-
1996
- 1996-01-30 IL IL11696796A patent/IL116967A0/xx unknown
-
1997
- 1997-05-30 GR GR970401252T patent/GR3023608T3/el unknown
-
1998
- 1998-04-03 GR GR980400706T patent/GR3026522T3/el unknown
-
1999
- 1999-08-30 KR KR1019990036254A patent/KR100249593B1/ko not_active IP Right Cessation
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