NO302120B1 - Kjemisk luminescerende 3-(substituerte adamant 2'-yliden)-1,2-dioksetaner - Google Patents
Kjemisk luminescerende 3-(substituerte adamant 2'-yliden)-1,2-dioksetaner Download PDFInfo
- Publication number
- NO302120B1 NO302120B1 NO921682A NO921682A NO302120B1 NO 302120 B1 NO302120 B1 NO 302120B1 NO 921682 A NO921682 A NO 921682A NO 921682 A NO921682 A NO 921682A NO 302120 B1 NO302120 B1 NO 302120B1
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- NO
- Norway
- Prior art keywords
- dioxetane
- amppd
- group
- compound according
- disodium
- Prior art date
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- -1 dioxetane compound Chemical class 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 24
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims description 20
- 229910019142 PO4 Inorganic materials 0.000 claims description 19
- 239000010452 phosphate Substances 0.000 claims description 19
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical group [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 16
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- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- SUYVUBYJARFZHO-RRKCRQDMSA-N dATP Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 SUYVUBYJARFZHO-RRKCRQDMSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000030609 dephosphorylation Effects 0.000 description 1
- 238000006209 dephosphorylation reaction Methods 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 239000005546 dideoxynucleotide Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- FUWPUSBPIRKOCW-UHFFFAOYSA-N dioxetane;phenol Chemical compound C1COO1.OC1=CC=CC=C1 FUWPUSBPIRKOCW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 230000009483 enzymatic pathway Effects 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- YQOKLYTXVFAUCW-UHFFFAOYSA-N guanidine;isothiocyanic acid Chemical compound N=C=S.NC(N)=N YQOKLYTXVFAUCW-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910001385 heavy metal Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical class CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229940028885 interleukin-4 Drugs 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000004530 micro-emulsion 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
- 238000007899 nucleic acid hybridization Methods 0.000 description 1
- 108010028584 nucleotidase Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000007124 photooxygenation reaction Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 125000005547 pivalate group Chemical group 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108010043671 prostatic acid phosphatase Proteins 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical compound N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 1
- YJWSBMQTQRNKPO-UHFFFAOYSA-M sodium;dodecyl sulfite Chemical compound [Na+].CCCCCCCCCCCCOS([O-])=O YJWSBMQTQRNKPO-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- NTBHQWQOMYCCJI-UHFFFAOYSA-N triethyl(trioxidanyl)silane Chemical compound CC[Si](CC)(CC)OOO NTBHQWQOMYCCJI-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000004148 unit process Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1788—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
- C07F9/65512—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Luminescent Compositions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Fats And Perfumes (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Polyethers (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polyesters Or Polycarbonates (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/574,787 US5220005A (en) | 1986-07-24 | 1990-08-30 | Substituted adamantyl dioxetanes |
| US07/574,786 US5112960A (en) | 1989-07-17 | 1990-08-30 | Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes |
| PCT/US1991/006096 WO1992004341A1 (en) | 1990-08-30 | 1991-08-30 | Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO921682L NO921682L (no) | 1992-04-29 |
| NO921682D0 NO921682D0 (no) | 1992-04-29 |
| NO302120B1 true NO302120B1 (no) | 1998-01-26 |
Family
ID=27076500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO921682A NO302120B1 (no) | 1990-08-30 | 1992-04-29 | Kjemisk luminescerende 3-(substituerte adamant 2'-yliden)-1,2-dioksetaner |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0497972B1 (de) |
| JP (1) | JP2552413B2 (de) |
| AT (1) | ATE174914T1 (de) |
| AU (1) | AU656927B2 (de) |
| BR (1) | BR9105888A (de) |
| CA (1) | CA2069957C (de) |
| DE (1) | DE69130668T2 (de) |
| DK (1) | DK0497972T3 (de) |
| ES (1) | ES2128326T3 (de) |
| FI (1) | FI102751B (de) |
| NO (1) | NO302120B1 (de) |
| OA (1) | OA09659A (de) |
| WO (1) | WO1992004341A1 (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5538847A (en) * | 1989-07-17 | 1996-07-23 | Tropix, Inc. | Chemiluminescent 1,2-dioxetanes |
| US5582980A (en) * | 1989-07-17 | 1996-12-10 | Tropix, Inc. | Chemiluminescent 1,2-dioxetanes |
| US6022964A (en) | 1989-07-17 | 2000-02-08 | Tropix, Inc. | Chemiluminescent 1,2-dioxetanes |
| US5783381A (en) * | 1995-10-19 | 1998-07-21 | Tropix, Inc. | Chemiluminescent 1,2-dioxetanes |
| US6068979A (en) * | 1998-04-22 | 2000-05-30 | Lumigen, Inc. | Simplified sequential chemiluminescent detection |
| AU781255B2 (en) * | 1998-12-15 | 2005-05-12 | Applied Biosystems, Llc | Multiple enzyme assays |
| EP1185710A2 (de) * | 1999-04-16 | 2002-03-13 | Zymetx, Inc. | Verfahren zum nachweis von viren, das viralisch-codierte enzymen und chemilumineszentsubstraten verwendet |
| JP4434015B2 (ja) * | 2002-06-24 | 2010-03-17 | 富士レビオ株式会社 | 化学発光増強剤 |
| EP2285979B2 (de) | 2008-05-27 | 2020-02-19 | Dako Denmark A/S | Hybridisierungszusammensetzungen und -verfahren |
| US9303287B2 (en) | 2009-02-26 | 2016-04-05 | Dako Denmark A/S | Compositions and methods for RNA hybridization applications |
| EP2761028A1 (de) | 2011-09-30 | 2014-08-06 | Dako Denmark A/S | Hybridisierungszusammensetzungen und -verfahren mit formamid |
| EP2768974B1 (de) | 2011-10-21 | 2017-07-19 | Dako Denmark A/S | Hybridisierungszusammensetzungen und -verfahren |
| DE102016119810A1 (de) | 2016-10-18 | 2018-04-19 | Hamilton Bonaduz Ag | Schichten zum Nachweis von Sauerstoff |
| CN113203728B (zh) * | 2021-03-19 | 2022-07-19 | 四川轻化工大学 | 一种臭氧检测装置及其检测方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983779A (en) * | 1986-07-17 | 1991-01-08 | The Board Of Governors Of Wayne State University | Process for the preparation of vinyl ethers |
-
1991
- 1991-08-30 AT AT91919701T patent/ATE174914T1/de not_active IP Right Cessation
- 1991-08-30 DE DE69130668T patent/DE69130668T2/de not_active Expired - Lifetime
- 1991-08-30 JP JP3518245A patent/JP2552413B2/ja not_active Expired - Lifetime
- 1991-08-30 ES ES91919701T patent/ES2128326T3/es not_active Expired - Lifetime
- 1991-08-30 AU AU88714/91A patent/AU656927B2/en not_active Expired
- 1991-08-30 EP EP91919701A patent/EP0497972B1/de not_active Expired - Lifetime
- 1991-08-30 DK DK91919701T patent/DK0497972T3/da active
- 1991-08-30 BR BR919105888A patent/BR9105888A/pt unknown
- 1991-08-30 CA CA002069957A patent/CA2069957C/en not_active Expired - Lifetime
- 1991-08-30 WO PCT/US1991/006096 patent/WO1992004341A1/en active IP Right Grant
-
1992
- 1992-04-20 OA OA60193A patent/OA09659A/en unknown
- 1992-04-29 NO NO921682A patent/NO302120B1/no not_active IP Right Cessation
- 1992-04-29 FI FI921925A patent/FI102751B/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| BR9105888A (pt) | 1992-11-10 |
| WO1992004341A1 (en) | 1992-03-19 |
| JP2552413B2 (ja) | 1996-11-13 |
| JPH05503714A (ja) | 1993-06-17 |
| NO921682L (no) | 1992-04-29 |
| FI102751B1 (fi) | 1999-02-15 |
| OA09659A (en) | 1993-05-15 |
| AU656927B2 (en) | 1995-02-23 |
| DK0497972T3 (da) | 1999-08-23 |
| CA2069957A1 (en) | 1992-03-01 |
| ES2128326T3 (es) | 1999-05-16 |
| DE69130668T2 (de) | 1999-05-20 |
| FI102751B (fi) | 1999-02-15 |
| EP0497972B1 (de) | 1998-12-23 |
| CA2069957C (en) | 2000-07-18 |
| DE69130668D1 (de) | 1999-02-04 |
| EP0497972A1 (de) | 1992-08-12 |
| FI921925A0 (fi) | 1992-04-29 |
| ATE174914T1 (de) | 1999-01-15 |
| FI921925A (fi) | 1992-04-29 |
| NO921682D0 (no) | 1992-04-29 |
| AU8871491A (en) | 1992-03-30 |
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