IL97276A - Process for the preparation of (2r,3r)-cis-beta-phenylglycidic acid - Google Patents
Process for the preparation of (2r,3r)-cis-beta-phenylglycidic acidInfo
- Publication number
- IL97276A IL97276A IL9727691A IL9727691A IL97276A IL 97276 A IL97276 A IL 97276A IL 9727691 A IL9727691 A IL 9727691A IL 9727691 A IL9727691 A IL 9727691A IL 97276 A IL97276 A IL 97276A
- Authority
- IL
- Israel
- Prior art keywords
- des
- melange
- les
- cis
- avec
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title abstract description 4
- 230000008569 process Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 49
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 28
- 238000001914 filtration Methods 0.000 claims description 10
- 230000009471 action Effects 0.000 claims description 7
- 229940123237 Taxane Drugs 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 238000001556 precipitation Methods 0.000 abstract description 4
- 229930012538 Paclitaxel Natural products 0.000 abstract description 3
- 229960001592 paclitaxel Drugs 0.000 abstract description 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 13
- 239000011591 potassium Substances 0.000 description 13
- 229910052700 potassium Inorganic materials 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 6
- 229940089960 chloroacetate Drugs 0.000 description 6
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 101100135641 Caenorhabditis elegans par-3 gene Proteins 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- 241001644893 Entandrophragma utile Species 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 101150062821 chlP gene Proteins 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings 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
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings 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
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings 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 of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9002098A FR2658513B1 (fr) | 1990-02-21 | 1990-02-21 | Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r). |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL97276A0 IL97276A0 (en) | 1992-05-25 |
| IL97276A true IL97276A (en) | 1995-03-30 |
Family
ID=9393961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9727691A IL97276A (en) | 1990-02-21 | 1991-02-19 | Process for the preparation of (2r,3r)-cis-beta-phenylglycidic acid |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5256803A (de) |
| EP (1) | EP0515541B1 (de) |
| JP (1) | JP3012325B2 (de) |
| KR (1) | KR100190559B1 (de) |
| AT (1) | ATE104970T1 (de) |
| AU (1) | AU647088B2 (de) |
| CA (1) | CA2071979C (de) |
| CZ (1) | CZ279594B6 (de) |
| DE (1) | DE69101836T2 (de) |
| DK (1) | DK0515541T3 (de) |
| ES (1) | ES2063499T3 (de) |
| FI (1) | FI113766B (de) |
| FR (1) | FR2658513B1 (de) |
| HU (1) | HU207856B (de) |
| IE (1) | IE65338B1 (de) |
| IL (1) | IL97276A (de) |
| NO (1) | NO179836C (de) |
| NZ (1) | NZ237173A (de) |
| PT (1) | PT96848B (de) |
| RU (1) | RU2056414C1 (de) |
| SK (1) | SK278331B6 (de) |
| WO (1) | WO1991013066A2 (de) |
| YU (1) | YU48670B (de) |
| ZA (1) | ZA911280B (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3140093A (en) * | 1991-11-22 | 1993-06-15 | University Of Mississippi, The | Synthesis and optical resolution of the taxol side chain and related compounds |
| DK0639186T3 (da) * | 1992-04-17 | 1999-12-13 | Abbott Lab | Taxolderivater |
| FR2691460B1 (fr) * | 1992-05-21 | 1994-07-22 | Rhone Poulenc Rorer Sa | Nouveaux derives du taxane, leur preparation et les compositions qui les contiennent. |
| IL107950A (en) | 1992-12-15 | 2001-04-30 | Upjohn Co | 7β, 8β - METHANO-TAXOLS, THEIR PREPARATION AND ANTINEOPLASTIC PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| US5646176A (en) | 1992-12-24 | 1997-07-08 | Bristol-Myers Squibb Company | Phosphonooxymethyl ethers of taxane derivatives |
| ATE253563T1 (de) * | 1993-02-05 | 2003-11-15 | Bryn Mawr College | Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten |
| US5684175A (en) * | 1993-02-05 | 1997-11-04 | Napro Biotherapeutics, Inc. | C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor |
| DE69433146T2 (de) * | 1993-06-11 | 2004-06-09 | Pharmacia & Upjohn Co., Kalamazoo | Delta 6,7-Taxol Derivate antineoplastische Verbindungen und diese enthaltende pharmazeutische Zusammenstellungen |
| IL127598A (en) * | 1994-01-28 | 2003-04-10 | Upjohn Co | Process for preparing isotaxol analogs |
| EP0821679B1 (de) * | 1995-04-20 | 2001-07-11 | Chirotech Technology Limited | Asymmetrische epoxide, ihre synthese und ihre verwendung |
| US5675025A (en) * | 1995-06-07 | 1997-10-07 | Napro Biotherapeutics, Inc. | Paclitaxel synthesis from precursor compounds and methods of producing the same |
| FR2740451B1 (fr) * | 1995-10-27 | 1998-01-16 | Seripharm | Nouveaux intermediaires pour l'hemisynthese de taxanes, leurs procedes de preparation et leur utilisation dans la synthese generale des taxanes |
| US5688977A (en) * | 1996-02-29 | 1997-11-18 | Napro Biotherapeutics, Inc. | Method for docetaxel synthesis |
| US6228955B1 (en) | 1996-04-19 | 2001-05-08 | Chirotech Technology, Ltd. | Asymmetric epoxides, their synthesis and use |
| US5750737A (en) * | 1996-09-25 | 1998-05-12 | Sisti; Nicholas J. | Method for paclitaxel synthesis |
| FR2776292B1 (fr) * | 1998-03-20 | 2004-09-10 | Oncopharm | Cephalotaxanes porteurs de chaine laterale et leur procede de synthese |
| US6479679B1 (en) | 2001-04-25 | 2002-11-12 | Napro Biotherapeutics, Inc. | Two-step conversion of protected taxane ester to paclitaxel |
| US6452025B1 (en) | 2001-04-25 | 2002-09-17 | Napro Biotherapeutics, Inc. | Three-step conversion of protected taxane ester to paclitaxel |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3901915A (en) * | 1973-10-10 | 1975-08-26 | Hoffmann La Roche | Optical resolution of organic carboxylic acids |
| JPS56110683A (en) * | 1980-02-07 | 1981-09-01 | Taisho Pharmaceut Co Ltd | Preparation of optical active epoxysuccinate |
| JPS6013775A (ja) * | 1983-07-05 | 1985-01-24 | Sawai Seiyaku Kk | 光学活性３−（ｐ−アルコキシフエニル）グリシツド酸アルカリ金属塩の製造法 |
| JPS61145174A (ja) * | 1984-12-20 | 1986-07-02 | Nippon Chemiphar Co Ltd | 新規な光学活性エポキシプロピオン酸エステル誘導体の製造法 |
| FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2601676B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Procede de preparation du taxol et du desacetyl-10 taxol |
| JPH01226881A (ja) * | 1988-03-04 | 1989-09-11 | Tanabe Seiyaku Co Ltd | 光学活性３−フェニルグリシッド酸エステル類化合物の製法 |
| FR2629819B1 (fr) * | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
| FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| US4885375A (en) * | 1988-05-18 | 1989-12-05 | Marion Laboratories, Inc. | Resolution of 3-(4-methoxyphenyl)glycidic acid with in situ conversion to alkyl esters |
| DE3906953A1 (de) * | 1989-03-04 | 1990-09-20 | Byk Gulden Lomberg Chem Fab | Verfahren zur herstellung optisch reiner oxirancarbonsaeuren |
| CA2023645C (fr) * | 1989-08-23 | 2002-03-26 | Jean-Noel Denis | Procede pour la preparation enantioselective de derives de la phenylisoserine |
| IT1240651B (it) * | 1990-05-17 | 1993-12-17 | Zambon Spa | Processo per la risoluzione di derivati glicidici |
| CA2088355A1 (en) * | 1990-08-01 | 1992-02-02 | Alvydas Alfonsas Jarmas | Process and intermediate for the preparation of 2-hydroxy-3-sulfido-3-phenyl propanoic acids |
-
1990
- 1990-02-21 FR FR9002098A patent/FR2658513B1/fr not_active Expired - Fee Related
-
1991
- 1991-02-19 IL IL9727691A patent/IL97276A/en not_active IP Right Cessation
- 1991-02-20 CZ CS91439A patent/CZ279594B6/cs not_active IP Right Cessation
- 1991-02-20 IE IE58791A patent/IE65338B1/en not_active IP Right Cessation
- 1991-02-20 DE DE69101836T patent/DE69101836T2/de not_active Expired - Lifetime
- 1991-02-20 US US07/920,509 patent/US5256803A/en not_active Expired - Lifetime
- 1991-02-20 EP EP91905073A patent/EP0515541B1/de not_active Expired - Lifetime
- 1991-02-20 ES ES91905073T patent/ES2063499T3/es not_active Expired - Lifetime
- 1991-02-20 AU AU73461/91A patent/AU647088B2/en not_active Expired
- 1991-02-20 RU SU915053046A patent/RU2056414C1/ru active
- 1991-02-20 AT AT9191905073T patent/ATE104970T1/de not_active IP Right Cessation
- 1991-02-20 HU HU922668A patent/HU207856B/hu unknown
- 1991-02-20 WO PCT/FR1991/000133 patent/WO1991013066A2/fr not_active Ceased
- 1991-02-20 YU YU30291A patent/YU48670B/sh unknown
- 1991-02-20 CA CA002071979A patent/CA2071979C/fr not_active Expired - Lifetime
- 1991-02-20 JP JP3505197A patent/JP3012325B2/ja not_active Expired - Lifetime
- 1991-02-20 NZ NZ237173A patent/NZ237173A/xx unknown
- 1991-02-20 SK SK439-91A patent/SK278331B6/sk not_active IP Right Cessation
- 1991-02-20 DK DK91905073.2T patent/DK0515541T3/da active
- 1991-02-21 ZA ZA911280A patent/ZA911280B/xx unknown
- 1991-02-21 PT PT96848A patent/PT96848B/pt not_active IP Right Cessation
-
1992
- 1992-08-17 FI FI923680A patent/FI113766B/fi active
- 1992-08-18 NO NO923225A patent/NO179836C/no not_active IP Right Cessation
- 1992-08-20 KR KR1019920701997A patent/KR100190559B1/ko not_active Expired - Lifetime
Also Published As
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