ES8801305A1 - Procedimiento para preparar peptidos difluorcetonicos - Google Patents
Procedimiento para preparar peptidos difluorcetonicosInfo
- Publication number
- ES8801305A1 ES8801305A1 ES555826A ES555826A ES8801305A1 ES 8801305 A1 ES8801305 A1 ES 8801305A1 ES 555826 A ES555826 A ES 555826A ES 555826 A ES555826 A ES 555826A ES 8801305 A1 ES8801305 A1 ES 8801305A1
- Authority
- ES
- Spain
- Prior art keywords
- difluorketonic
- peptides
- formulas
- mixture
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 abstract 1
- 201000008482 osteoarthritis Diseases 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07C271/16—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 singly-bound oxygen atoms
-
- 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
- C07C271/18—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 doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
METODO DE PREPARAR PEPTIDOS DIFLUORCETONICOS. CONSISTE EN OXIDAR UN ALCOHOL DE FORMULAS (IV), (V) O (VI) POR REACCION CON UN AGENTE DE OXIDACION TAL COMO UNA MEZCLA DE CLORURO DE OXALILO, DIMETIL SULFOXIDO Y UNA AMINA TERCIARIA; UNA MEZCLA DE ANHIDRIDO ACETICO Y DIMETIL SULF''OIDO; COMPLEJO DE TRIOXIDO DE CROMO PIRIDINA; O 1,1,1-TRIACETOXI-2,1-BENZOXIDO-3(3H)-ONA; Y A TEMPERATURA ENTRE 0 Y 35JC, PARA OBTENER PEPTIDOS DIFLUORCETONICOS DE FORMULAS (I), (II) O (III), DONDE R1 ES UN GRUPO ALQUILO DE C 1 A 5; R2 ES UN GRUPO ALQUILO DE C 1 A 6, ALQUILO DE C 1 A 10 Y OTROS; R3 ES UN GRUPO ALQUILO DE C 1 A 12 Y OTROS; R4 ES H Y METILO; Y RA ES CH3 Y OTROS. TIENEN APLICACIONES FARMACEUTICAS PARA TRATAR ARTRITIS REUMATOIDE, OSTEOARTRITIS Y OTRAS ENFERMEDADES.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858514436A GB8514436D0 (en) | 1985-06-07 | 1985-06-07 | Selected difluoro derivatives |
| GB858514440A GB8514440D0 (en) | 1985-06-07 | 1985-06-07 | Difluoro ketone tripeptide derivatives |
| GB858514438A GB8514438D0 (en) | 1985-06-07 | 1985-06-07 | Selected difluoro ketone dipeptide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES555826A0 ES555826A0 (es) | 1987-12-16 |
| ES8801305A1 true ES8801305A1 (es) | 1987-12-16 |
Family
ID=27262698
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES555826A Expired ES8801305A1 (es) | 1985-06-07 | 1986-06-06 | Procedimiento para preparar peptidos difluorcetonicos |
| ES557733A Expired ES8802619A1 (es) | 1985-06-07 | 1987-09-16 | Procedimiento para preparar peptidos difluorcetonicos |
| ES557735A Expired ES8802321A1 (es) | 1985-06-07 | 1987-09-16 | Procedimiento para preparar peptidos difluorcetonicos |
| ES557734A Expired ES8900051A1 (es) | 1985-06-07 | 1987-09-16 | Procedimiento para preparar peptidos difluorcetonicos |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES557733A Expired ES8802619A1 (es) | 1985-06-07 | 1987-09-16 | Procedimiento para preparar peptidos difluorcetonicos |
| ES557735A Expired ES8802321A1 (es) | 1985-06-07 | 1987-09-16 | Procedimiento para preparar peptidos difluorcetonicos |
| ES557734A Expired ES8900051A1 (es) | 1985-06-07 | 1987-09-16 | Procedimiento para preparar peptidos difluorcetonicos |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4880780A (es) |
| EP (1) | EP0204571B1 (es) |
| JP (1) | JPH07116159B2 (es) |
| AT (1) | ATE71934T1 (es) |
| AU (1) | AU594683B2 (es) |
| DE (1) | DE3683541D1 (es) |
| DK (1) | DK267686A (es) |
| ES (4) | ES8801305A1 (es) |
| FI (1) | FI86859C (es) |
| GR (1) | GR861488B (es) |
| HU (1) | HU208438B (es) |
| IE (1) | IE59146B1 (es) |
| IL (1) | IL79049A0 (es) |
| NO (1) | NO170585C (es) |
| NZ (1) | NZ216437A (es) |
| PT (1) | PT82724B (es) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8600263D0 (en) * | 1985-01-22 | 1986-02-12 | Ici America Inc | Peptide derivatives |
| US5496927A (en) * | 1985-02-04 | 1996-03-05 | Merrell Pharmaceuticals Inc. | Peptidase inhibitors |
| GB8613703D0 (en) * | 1986-06-05 | 1986-07-09 | Ici America Inc | Difluoro peptide compounds |
| GB8711748D0 (en) * | 1986-06-05 | 1987-06-24 | Ici America Inc | Difluoro keto compounds |
| GB8809316D0 (en) * | 1987-05-11 | 1988-05-25 | Ici America Inc | Heterocyclic ketones |
| EP0371179A1 (en) * | 1988-10-28 | 1990-06-06 | Merrell Dow Pharmaceuticals Inc. | Novel analogs of peptidase substrates |
| EP0369391A3 (en) * | 1988-11-15 | 1991-09-25 | Boehringer Ingelheim Pharmaceuticals Inc. | N-substituted amides |
| GB8910547D0 (en) * | 1989-05-08 | 1989-06-21 | Ici America Inc | Substituted ketones |
| US5221665A (en) * | 1989-10-27 | 1993-06-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | N-substituted amides |
| US5391705A (en) * | 1991-03-15 | 1995-02-21 | Merrell Dow Pharmaceuticals Inc. | Polyfluorinated tripeptide thrombin inhibitors |
| ATE181925T1 (de) * | 1991-05-23 | 1999-07-15 | Merrell Pharma Inc | Hemmstoffe für kathepsin-g und elastase zur verhütung von bindegewebsabbau |
| US5478811A (en) * | 1991-08-22 | 1995-12-26 | Merrell Dow Pharmaceuticals Inc. | Orally-active elastase inhibitors |
| US5714470A (en) | 1991-08-22 | 1998-02-03 | Merrell Pharmaceuticals, Inc. | Orally-active elastase inhibitors |
| US5486529A (en) * | 1992-04-16 | 1996-01-23 | Zeneca Limited | Certain pyridyl ketones for treating diseases involving leukocyte elastase |
| IL108031A0 (en) * | 1992-12-22 | 1994-04-12 | Procter & Gamble | Difluoro pentapeptide derivatives and pharmaceutical compositions containing them |
| HU221197B1 (en) * | 1994-06-02 | 2002-08-28 | Aventis Pharma Inc | Elastase inhibitor tripeptides and pharmaceutical compositions comprising thereof |
| ES2161293T3 (es) * | 1994-06-02 | 2001-12-01 | Merrell Pharma Inc | Derivados de enol acilados como profarmacos de inhibidores de la elastasa. |
| DK0763055T3 (da) * | 1994-06-02 | 2000-05-08 | Merrell Pharma Inc | Perflouralkylketon-inhibitorer af elastase og fremgangsmåde til fremstilling deraf |
| US6069232A (en) * | 1995-10-02 | 2000-05-30 | Hoechst Marion Roussel, Inc. | Polyfluoroalkyl tryptophan tripeptide thrombin inhibitors |
| US5948886A (en) * | 1996-11-20 | 1999-09-07 | Hoechst Marion Roussel, Inc. | Acylated enol derivatives of α-ketoesters and α-ketoamides |
| US6172044B1 (en) | 1995-12-01 | 2001-01-09 | Aventis Pharmaceuticals Inc. | Acylated enol derivative of α-ketoesters and α-ketoamides |
| US6673784B1 (en) | 1996-03-19 | 2004-01-06 | G. D. Searle & Co. | Electrophilic ketones for the treatment of herpesvirus infections |
| US5739354A (en) * | 1996-03-26 | 1998-04-14 | Hoechst Marion Roussel, Inc. | Process for the preparation of N-methyl-D-phenylalanyl-N- 1- 3- (aminoiminomethyl)amino!propyl!-3,3-difluoro-2-oxohexyl!-L-prolinamide |
| CZ298749B6 (cs) | 1996-10-18 | 2008-01-16 | Vertex Pharmaceuticals Incorporated | Inhibitory serinových proteáz a farmaceutické prostředky s jejich obsahem |
| SV2003000617A (es) * | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| PE20050374A1 (es) | 2003-09-05 | 2005-05-30 | Vertex Pharma | Inhibidores de proteasas de serina, en particular proteasa ns3-ns4a del vhc |
| US7964624B1 (en) | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| CA2643688A1 (en) | 2006-02-27 | 2007-08-30 | Vertex Pharmaceuticals Incorporated | Co-crystals and pharmaceutical compositions comprising the same |
| WO2007109080A2 (en) * | 2006-03-16 | 2007-09-27 | Vertex Pharmaceuticals Incorporated | Deuterated hepatitis c protease inhibitors |
| CN101534824A (zh) * | 2006-11-17 | 2009-09-16 | 艾博特公司 | 作为化学活素受体拮抗剂的氨基吡咯烷 |
| WO2008106058A2 (en) | 2007-02-27 | 2008-09-04 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| GEP20125645B (en) | 2007-02-27 | 2012-09-25 | Vertex Pharma | Co-crystals and pharmaceutical compositions comprising the same |
| WO2009032198A1 (en) | 2007-08-30 | 2009-03-12 | Vertex Pharmaceuticals Incorporated | Co-crystals and pharmaceutical compositions comprising the same |
| US8623358B2 (en) | 2009-08-29 | 2014-01-07 | Abbvie Inc. | Therapeutic DLL4 binding proteins |
| EP2542582A4 (en) | 2010-03-02 | 2013-12-04 | Abbvie Inc | THERAPEUTIC PROTEINS LINKING TO DLL4 |
| US8735546B2 (en) | 2010-08-03 | 2014-05-27 | Abbvie Inc. | Dual variable domain immunoglobulins and uses thereof |
| AU2013337775B2 (en) | 2012-11-01 | 2017-03-30 | Abbvie Inc. | Anti-VEGF/DLL4 dual variable domain immunoglobulins and uses thereof |
| US10093733B2 (en) | 2014-12-11 | 2018-10-09 | Abbvie Inc. | LRP-8 binding dual variable domain immunoglobulin proteins |
| CN107531653B (zh) * | 2015-05-11 | 2021-10-19 | 豪夫迈·罗氏有限公司 | 新的二氟酮酰胺衍生物 |
| TW201710286A (zh) | 2015-06-15 | 2017-03-16 | 艾伯維有限公司 | 抗vegf、pdgf及/或其受體之結合蛋白 |
| EP3994148A1 (en) | 2019-07-01 | 2022-05-11 | Basf Se | Peptide acetals for stabilising enzymes |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787249A (fr) | 1971-08-05 | 1973-02-05 | Squibb & Sons Inc | Derives amino d'acides pyrazolopyridine carboxyliques, leurs esters et les sels de ces composes, ainsi que leurs procedes de preparation |
| US3935280A (en) | 1975-01-10 | 1976-01-27 | Aldrich-Boranes, Inc. | Reduction of amino acids in the presence of boron trifluoride |
| US4277395A (en) * | 1980-06-16 | 1981-07-07 | Richardson-Merrell Inc. | Novel enzyme inhibitors |
| EP0124317B1 (en) | 1983-04-27 | 1990-04-11 | Ici Americas Inc. | Proline derivatives |
| US4518528A (en) * | 1983-05-19 | 1985-05-21 | Rasnick David W | α Amino fluoro ketones |
| GB8600263D0 (en) * | 1985-01-22 | 1986-02-12 | Ici America Inc | Peptide derivatives |
-
1986
- 1986-06-05 EP EP86304296A patent/EP0204571B1/en not_active Expired - Lifetime
- 1986-06-05 DE DE8686304296T patent/DE3683541D1/de not_active Expired - Fee Related
- 1986-06-05 AT AT86304296T patent/ATE71934T1/de not_active IP Right Cessation
- 1986-06-06 ES ES555826A patent/ES8801305A1/es not_active Expired
- 1986-06-06 AU AU58454/86A patent/AU594683B2/en not_active Ceased
- 1986-06-06 IE IE151386A patent/IE59146B1/en not_active IP Right Cessation
- 1986-06-06 DK DK267686A patent/DK267686A/da not_active Application Discontinuation
- 1986-06-06 HU HU862393A patent/HU208438B/hu not_active IP Right Cessation
- 1986-06-06 PT PT82724A patent/PT82724B/pt not_active IP Right Cessation
- 1986-06-06 JP JP61130457A patent/JPH07116159B2/ja not_active Expired - Fee Related
- 1986-06-06 IL IL79049A patent/IL79049A0/xx unknown
- 1986-06-06 GR GR861488A patent/GR861488B/el unknown
- 1986-06-06 NZ NZ216437A patent/NZ216437A/xx unknown
- 1986-06-06 FI FI862434A patent/FI86859C/fi not_active IP Right Cessation
- 1986-06-06 NO NO862269A patent/NO170585C/no unknown
-
1987
- 1987-06-04 US US07/058,079 patent/US4880780A/en not_active Expired - Lifetime
- 1987-09-16 ES ES557733A patent/ES8802619A1/es not_active Expired
- 1987-09-16 ES ES557735A patent/ES8802321A1/es not_active Expired
- 1987-09-16 ES ES557734A patent/ES8900051A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07116159B2 (ja) | 1995-12-13 |
| ES8900051A1 (es) | 1988-11-16 |
| NZ216437A (en) | 1990-06-26 |
| ES555826A0 (es) | 1987-12-16 |
| IE59146B1 (en) | 1994-01-12 |
| ES557734A0 (es) | 1988-11-16 |
| NO862269D0 (no) | 1986-06-06 |
| AU5845486A (en) | 1986-12-18 |
| DK267686A (da) | 1986-12-08 |
| ES8802321A1 (es) | 1988-05-01 |
| JPS6253951A (ja) | 1987-03-09 |
| FI86859B (fi) | 1992-07-15 |
| EP0204571A2 (en) | 1986-12-10 |
| DK267686D0 (da) | 1986-06-06 |
| AU594683B2 (en) | 1990-03-15 |
| GR861488B (en) | 1986-09-05 |
| US4880780A (en) | 1989-11-14 |
| NO862269L (no) | 1986-12-08 |
| EP0204571A3 (en) | 1988-09-21 |
| IE861513L (en) | 1986-12-07 |
| PT82724A (en) | 1986-07-01 |
| ES557733A0 (es) | 1988-09-01 |
| FI862434A7 (fi) | 1986-12-08 |
| ATE71934T1 (de) | 1992-02-15 |
| FI86859C (fi) | 1992-10-26 |
| NO170585B (no) | 1992-07-27 |
| ES557735A0 (es) | 1988-05-01 |
| HU208438B (en) | 1993-10-28 |
| FI862434A0 (fi) | 1986-06-06 |
| PT82724B (pt) | 1988-12-15 |
| IL79049A0 (en) | 1986-09-30 |
| DE3683541D1 (de) | 1992-03-05 |
| ES8802619A1 (es) | 1988-09-01 |
| NO170585C (no) | 1992-11-04 |
| EP0204571B1 (en) | 1992-01-22 |
| HUT40811A (en) | 1987-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20001102 |