FI120261B - PNA-syntes under användning av gentemot svaga syror labila aminoskyddsgrupper - Google Patents
PNA-syntes under användning av gentemot svaga syror labila aminoskyddsgrupper Download PDFInfo
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- FI120261B FI120261B FI951130A FI951130A FI120261B FI 120261 B FI120261 B FI 120261B FI 951130 A FI951130 A FI 951130A FI 951130 A FI951130 A FI 951130A FI 120261 B FI120261 B FI 120261B
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- XUZLXCQFXTZASF-UHFFFAOYSA-N nitro(phenyl)methanol Chemical compound [O-][N+](=O)C(O)C1=CC=CC=C1 XUZLXCQFXTZASF-UHFFFAOYSA-N 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- RXNXLAHQOVLMIE-UHFFFAOYSA-N phenyl 10-methylacridin-10-ium-9-carboxylate Chemical compound C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)OC1=CC=CC=C1 RXNXLAHQOVLMIE-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002213 purine nucleotide Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 230000010837 receptor-mediated endocytosis Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 125000006853 reporter group Chemical group 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
- FMHHVULEAZTJMA-UHFFFAOYSA-N trioxsalen Chemical compound CC1=CC(=O)OC2=C1C=C1C=C(C)OC1=C2C FMHHVULEAZTJMA-UHFFFAOYSA-N 0.000 description 1
- 229960000850 trioxysalen Drugs 0.000 description 1
- 229930003231 vitamin Chemical group 0.000 description 1
- 239000011782 vitamin Chemical group 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
- C07K14/003—Peptide-nucleic acids (PNAs)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Gastroenterology & Hepatology (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (2)
1. Förfarande för framställning av PNA-oligomerer med formel I: B I (!) K’-(A)k-(Xln-(Q),-Q'’ 5 väri B/X är B c.g c - o MH-(CM,),~CH,-N-(CU, ) ,-CO 8 ( C H j ) , HH-CH-CO-NH-CHj-CO 8 (CH,)f HH-CH-CHj-CHj-CHj-CO B ( C H , ) , NH-CH,-CO~N~CH,-CO 8 i CU , C ' 0 I nh-ch,-ch2-ch-ch2-co o ? —CH NH-CMj-CH,-Nn/X-.C0 8 (ch,), . eller NH-CHj-CO-Nv^^do 31 γ» „ (CR,) -CO Γ '''Y _ (eH2>f NH-(CH2)g varvid f = 1 - 4; och g = 0 - 3; R° är väte, Ci-ig-alkanoyl, Ci-is-alkoxikarbonyl, C3-8-cykloalkanoyl, C7_i5-aroyl, C3-i3~heteroaroyl eller en grupp, 5 som gynnar intracellular upptagning av oligomeren; eller som i samband med hybridisationen samverkar med en mälnuklein-syra; A är en aminosyrarest; k är ett heltal 0 - 10;
10 Q är en aminosyrarest; 1 är ett heltal 0 - 10; B är en inom nukleotidkemin vanlig naturlig nukleo-bas eller icke-naturlig nukleobas eller en förläkemedels-form av dessa, eller ocksä en basersättningsförening;
15 Q° är hydroxi, NH2 eller NHR", väri R" är Ci-i8- alkyl, C2-i8-aminoalkyl eller C2_i8-hydroxialkyl; och n är ett heltal 1 - 50; vilket förfarande är kännetecknat av att a) tili en polymerbärare med formel II: 20 L-[polymer] (II) som är försedd med en ankargrupp L, som innehäller latent resten Q°, antingen kopplas först med ett för fast- 25 fassyntes vanligt förfarande aminosyror (Q'), vilkas sido-kedjor eventuellt är skyddade b) eventuellt avspjälks en i förhällande tili svaga syror labil skyddsgrupp PG med en lämplig reagens, c) upprepas stegen a och b (1-1) ganger, och 32 d) till den härvid som mellanprodukt uppkomna fore-ningen med formel III: (Q ' ) l-L-[polymer] (III) 5 väri L definieras sasom ovan, Q' är en aminosyra Q, vars eventuellt närvarande sidokedjefunktioner är skyddade, och 1 är ett heltal 0 - 10, eller direkt till polymerbäraren enligt formel II kopplas en förening med formel IV:
10 PG-X -OH (IV) ff B' väri PG är en i förhallande till svaga syror labil aminoskyddsgrupp och B'/X är en strukturdel enligt vad som definierats i formel I med en nukleobas, vars exocykliska 15 amino- eller hydroxifunktion är skyddad, varvid B' är en inom nukleotidkemin vanlig naturlig nukleobas eller icke-naturlig nukleobas, eller en förläkemedels-form av dessa, eller ocksä en basersättningsförening, vilkas exocykliska amino- eller hydroxigrupper eventuellt är 20 skyddade med lämpliga kända skyddsgrupper, genom att använda inom peptidkemin vanliga kopp-lingsreagenser, e) en tillfällig, i förhallande till svaga syror labil skyddsgrupp PG avspjälks genom användning av en lämp- 25 lig reagens, f) stegen d och e upprepas (n-1) ganger, g) med ett för fastfassyntes vanligt förfarande kopplas ytterligare aminosyror (A’) , vilkas sidokedjor eventuellt är skyddade, 30 h) en i förhallande tili svaga syror labil skydds grupp PG avspjälks genom användning av en lämplig reagens, i) stegen g och h upprepas (k—1) ganger, j) i det fallet att R° inte är väte, tillsätts res-ten R° med ett vanligt förfarande, 33 k) frän den som mellanprodukt erhallna föreningen enligt formel Ia: B I <!a) R ° " ( A ' )i(“( X I n — ( 0 ' ) | - L - (polymeeri 1 väri R°, k, B'/X, n, Q' och 1 definieras säsom 5 ovan, A' betecknar en aminosyra A, vars sidokedja eventu-ellt är skyddad, och L är en ankargrupp, föreningen enligt formel I avspjälks genom använd-ning av avspjälkningsreagensen frän polymerbäraren, varvid samtidigt eller även härnäst bortspjälks skyddsgrupper som 10 eventuellt förekommer i nukleobasernas exocykliska amino- eller hydroxifunktion och i aminosyrornas sidokedjor.
2. Förfarande enligt patentkrav 1 för framställning av PNA-oligomerer med formel I, kännetecknat av att A är en aminosyrarest frän gruppen glycin, leucin, 15 histidin, fenylalanin, cystein, lycin, arginin, asparaginsy- ra, glutaminsyra, prolin, tetrahydroisokinolin-3-karboxylsy-ra, oktahydroindol-2-karboxylsyra och N-(2-aminoetyl)glycin; k är ett heltal 0 - 6; Q är en aminosyrarest frän gruppen glycin, leucin, 20 histidin, fenylalanin, cystein, lycin, arginin, asparaginsy- ra, glutaminsyra, prolin, tetrahydroisokinolin-3-karboxylsy-ra, oktahydroindol-2-karboxylsyra och N-(2-aminoetyl)glycin; 1 är ett heltal 0 - 6; B är en naturlig nukleobas frän gruppen adenin, cy-25 tosin, guanin, tyrnin och uracil eller en icke-naturlig nukleobas frän gruppen purin, 2,β-diaminopyrin, 7-deaza-ade-nin, 7-deazaguanin, N4N4-etanocytosin, N6N6-etano-2,6-diami-nopurin, 5-metylcytosin, 5-C3-6-alkinyluracil, 5-C3_6-alki-nylcytosin, 5-fluoruracil eller pseudoisocytosin, 2-hydro-30 xi-5-metyl-4-triazolopyrimidin eller en förläkemedelsform av dessa, eller imidazol, nitroimidazol och triazol; och n är ett heltal 4-35.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4408531A DE4408531A1 (de) | 1994-03-14 | 1994-03-14 | PNA-Synthese unter Verwendung einer gegen schwache Säuren labilen Amino-Schutzgruppe |
| DE4408531 | 1994-03-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI951130A0 FI951130A0 (sv) | 1995-03-10 |
| FI951130A FI951130A (sv) | 1995-09-15 |
| FI120261B true FI120261B (sv) | 2009-08-31 |
Family
ID=6512696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI951130A FI120261B (sv) | 1994-03-14 | 1995-03-10 | PNA-syntes under användning av gentemot svaga syror labila aminoskyddsgrupper |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6046306A (sv) |
| EP (1) | EP0672700B1 (sv) |
| JP (1) | JP4098837B2 (sv) |
| AT (1) | ATE180805T1 (sv) |
| AU (1) | AU695931B2 (sv) |
| CA (1) | CA2144477C (sv) |
| DE (2) | DE4408531A1 (sv) |
| DK (1) | DK0672700T3 (sv) |
| ES (1) | ES2132450T3 (sv) |
| FI (1) | FI120261B (sv) |
| GR (1) | GR3030883T3 (sv) |
| NO (1) | NO321034B1 (sv) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7825215B1 (en) * | 1993-04-26 | 2010-11-02 | Peter E. Nielsen | Substituted nucleic acid mimics |
| US6133444A (en) * | 1993-12-22 | 2000-10-17 | Perseptive Biosystems, Inc. | Synthons for the synthesis and deprotection of peptide nucleic acids under mild conditions |
| US6150510A (en) | 1995-11-06 | 2000-11-21 | Aventis Pharma Deutschland Gmbh | Modified oligonucleotides, their preparation and their use |
| DE4438918A1 (de) * | 1994-11-04 | 1996-05-09 | Hoechst Ag | Modifizierte Oligonukleotide, deren Herstellung sowie deren Verwendung |
| JP2001518054A (ja) * | 1995-06-07 | 2001-10-09 | パーセプティブ バイオシステムズ，インコーポレーテッド | Ｐｎａ−ｄｎａキメラと、このキメラ合成用のｐｎａシントン |
| US20050042647A1 (en) * | 1996-06-06 | 2005-02-24 | Baker Brenda F. | Phosphorous-linked oligomeric compounds and their use in gene modulation |
| US20050032068A1 (en) * | 2002-11-05 | 2005-02-10 | Prakash Thazha P. | Sugar and backbone-surrogate-containing oligomeric compounds and compositions for use in gene modulation |
| US7812149B2 (en) | 1996-06-06 | 2010-10-12 | Isis Pharmaceuticals, Inc. | 2′-Fluoro substituted oligomeric compounds and compositions for use in gene modulations |
| US9096636B2 (en) * | 1996-06-06 | 2015-08-04 | Isis Pharmaceuticals, Inc. | Chimeric oligomeric compounds and their use in gene modulation |
| US20040171030A1 (en) * | 1996-06-06 | 2004-09-02 | Baker Brenda F. | Oligomeric compounds having modified bases for binding to cytosine and uracil or thymine and their use in gene modulation |
| US5898031A (en) | 1996-06-06 | 1999-04-27 | Isis Pharmaceuticals, Inc. | Oligoribonucleotides for cleaving RNA |
| US20050118605A9 (en) * | 1996-06-06 | 2005-06-02 | Baker Brenda F. | Oligomeric compounds having modified bases for binding to adenine and guanine and their use in gene modulation |
| US20040266706A1 (en) * | 2002-11-05 | 2004-12-30 | Muthiah Manoharan | Cross-linked oligomeric compounds and their use in gene modulation |
| US6331618B1 (en) * | 1999-05-13 | 2001-12-18 | Pe Corporation (Ny) | Compositions of solvents and high concentrations of nucleic acid analogs |
| DE10019136A1 (de) * | 2000-04-18 | 2001-10-31 | Aventis Pharma Gmbh | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
| DE10019135A1 (de) * | 2000-04-18 | 2001-10-31 | Aventis Pharma Gmbh | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
| US9150606B2 (en) * | 2002-11-05 | 2015-10-06 | Isis Pharmaceuticals, Inc. | Compositions comprising alternating 2'-modified nucleosides for use in gene modulation |
| US9150605B2 (en) * | 2002-11-05 | 2015-10-06 | Isis Pharmaceuticals, Inc. | Compositions comprising alternating 2′-modified nucleosides for use in gene modulation |
| WO2004044132A2 (en) * | 2002-11-05 | 2004-05-27 | Isis Pharmaceuticals, Inc. | Modified oligonucleotides for use in rna interference |
| CA2504694C (en) * | 2002-11-05 | 2013-10-01 | Isis Pharmaceuticals, Inc. | Polycyclic sugar surrogate-containing oligomeric compounds and compositions for use in gene modulation |
| US8569474B2 (en) | 2004-03-09 | 2013-10-29 | Isis Pharmaceuticals, Inc. | Double stranded constructs comprising one or more short strands hybridized to a longer strand |
| US8394947B2 (en) | 2004-06-03 | 2013-03-12 | Isis Pharmaceuticals, Inc. | Positionally modified siRNA constructs |
| JP2008501693A (ja) * | 2004-06-03 | 2008-01-24 | アイシス ファーマシューティカルズ、インク． | 遺伝子調節で使用するための個別に調節された鎖を有する二本鎖組成物 |
| US7884086B2 (en) | 2004-09-08 | 2011-02-08 | Isis Pharmaceuticals, Inc. | Conjugates for use in hepatocyte free uptake assays |
| PT1966130E (pt) | 2005-12-23 | 2014-01-30 | Zealand Pharma As | Compostos miméticos de lisina modificados |
| DK2468724T3 (en) | 2006-12-21 | 2016-02-22 | Zealand Pharma As | Synthesis of pyrrolidine compounds |
| DK3618847T3 (da) | 2017-05-05 | 2021-05-25 | Boston Medical Ct Corp | GAP-junction-modulatorer af intercellulær kommunikation og deres anvendelse til behandling af diabetisk øjensygdom |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5015733A (en) * | 1983-12-20 | 1991-05-14 | California Institute Of Technology | Nucleosides possessing blocked aliphatic amino groups |
| US5367066A (en) * | 1984-10-16 | 1994-11-22 | Chiron Corporation | Oligonucleotides with selectably cleavable and/or abasic sites |
| DE4016596A1 (de) * | 1990-05-23 | 1991-11-28 | Hoechst Ag | Ein neues kupplungsreagenz fuer die peptidsynthese |
| DK51092D0 (da) * | 1991-05-24 | 1992-04-15 | Ole Buchardt | Oligonucleotid-analoge betegnet pna, monomere synthoner og fremgangsmaade til fremstilling deraf samt anvendelser deraf |
| MX9207334A (es) * | 1991-12-18 | 1993-08-01 | Glaxo Inc | Acidos nucleicos peptidicos y formulacion farma- ceutica que los contiene |
-
1994
- 1994-03-14 DE DE4408531A patent/DE4408531A1/de not_active Withdrawn
-
1995
- 1995-03-08 AT AT95103318T patent/ATE180805T1/de active
- 1995-03-08 ES ES95103318T patent/ES2132450T3/es not_active Expired - Lifetime
- 1995-03-08 DE DE59506063T patent/DE59506063D1/de not_active Expired - Lifetime
- 1995-03-08 DK DK95103318T patent/DK0672700T3/da active
- 1995-03-08 EP EP95103318A patent/EP0672700B1/de not_active Expired - Lifetime
- 1995-03-10 FI FI951130A patent/FI120261B/sv not_active IP Right Cessation
- 1995-03-10 AU AU14801/95A patent/AU695931B2/en not_active Ceased
- 1995-03-13 NO NO19950957A patent/NO321034B1/no not_active IP Right Cessation
- 1995-03-13 CA CA002144477A patent/CA2144477C/en not_active Expired - Fee Related
- 1995-03-14 JP JP05464295A patent/JP4098837B2/ja not_active Expired - Fee Related
-
1997
- 1997-09-11 US US08/927,178 patent/US6046306A/en not_active Expired - Lifetime
-
1999
- 1999-07-30 GR GR990401964T patent/GR3030883T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0672700B1 (de) | 1999-06-02 |
| AU1480195A (en) | 1995-09-21 |
| FI951130A (sv) | 1995-09-15 |
| NO950957L (no) | 1995-09-15 |
| NO950957D0 (no) | 1995-03-13 |
| JP4098837B2 (ja) | 2008-06-11 |
| US6046306A (en) | 2000-04-04 |
| DE4408531A1 (de) | 1995-09-28 |
| DK0672700T3 (da) | 1999-11-29 |
| AU695931B2 (en) | 1998-08-27 |
| ATE180805T1 (de) | 1999-06-15 |
| JPH07285989A (ja) | 1995-10-31 |
| EP0672700A1 (de) | 1995-09-20 |
| GR3030883T3 (en) | 1999-11-30 |
| FI951130A0 (sv) | 1995-03-10 |
| NO321034B1 (no) | 2006-03-06 |
| ES2132450T3 (es) | 1999-08-16 |
| CA2144477C (en) | 2007-09-18 |
| CA2144477A1 (en) | 1995-09-15 |
| DE59506063D1 (de) | 1999-07-08 |
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