JP2002508428A5 - - Google Patents
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- JP2002508428A5 JP2002508428A5 JP2000539092A JP2000539092A JP2002508428A5 JP 2002508428 A5 JP2002508428 A5 JP 2002508428A5 JP 2000539092 A JP2000539092 A JP 2000539092A JP 2000539092 A JP2000539092 A JP 2000539092A JP 2002508428 A5 JP2002508428 A5 JP 2002508428A5
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- JP
- Japan
- Prior art keywords
- group
- compound
- amino
- alkyl
- hydrogen
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 21
- -1 succinimidyl ester Chemical class 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 13
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000012491 analyte Substances 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 150000001721 carbon Chemical class 0.000 description 6
- 150000007523 nucleic acids Chemical class 0.000 description 6
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 230000009870 specific binding Effects 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000001301 oxygen Chemical class 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Chemical class 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- 239000013077 target material Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000012163 sequencing technique Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- MEZJQXVOMGUAMP-UHFFFAOYSA-N 1-(2-methylnaphthalen-1-yl)pyrrole-2,5-dione Chemical compound CC1=CC=C2C=CC=CC2=C1N1C(=O)C=CC1=O MEZJQXVOMGUAMP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical class [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000005546 dideoxynucleotide Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002875 fluorescence polarization Methods 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 150000008300 phosphoramidites Chemical class 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 150000003461 sulfonyl halides Chemical class 0.000 description 2
- 239000011593 sulfur Chemical class 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical compound NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 108091008039 hormone receptors Proteins 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000007899 nucleic acid hybridization Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99221297A | 1997-12-17 | 1997-12-17 | |
| US08/992,212 | 1997-12-17 | ||
| PCT/US1998/026665 WO1999031181A1 (en) | 1997-12-17 | 1998-12-16 | Rigidized trimethine cyanine dyes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002508428A JP2002508428A (ja) | 2002-03-19 |
| JP2002508428A5 true JP2002508428A5 (https=) | 2012-02-02 |
| JP4927253B2 JP4927253B2 (ja) | 2012-05-09 |
Family
ID=25538049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000539092A Expired - Lifetime JP4927253B2 (ja) | 1997-12-17 | 1998-12-16 | 硬化トリメチンシアニン色素 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6686145B1 (https=) |
| EP (1) | EP1042407B1 (https=) |
| JP (1) | JP4927253B2 (https=) |
| AT (1) | ATE205515T1 (https=) |
| AU (1) | AU760598B2 (https=) |
| CA (1) | CA2314188C (https=) |
| DE (1) | DE69801682T2 (https=) |
| DK (1) | DK1042407T3 (https=) |
| ES (1) | ES2165711T3 (https=) |
| WO (1) | WO1999031181A1 (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6133445A (en) * | 1997-12-17 | 2000-10-17 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
| WO2004039894A2 (en) * | 2002-05-10 | 2004-05-13 | Carnegie Mellon University | Chiral indole intermediates and their fluorescent cyanine dyes containing functional groups |
| EP1196398A4 (en) * | 1999-07-06 | 2002-11-06 | Surromed Inc | BRIDGED FLUORESCENT DYES, THEIR PRODUCTION AND USE IN DETECTION METHODS |
| DE19937024A1 (de) * | 1999-08-05 | 2001-02-08 | Bayer Ag | Verwendung von Acylsulfonamido substituierten Polymethin-Farbstoffen als Fluoreszenz-Farbstoffe und/oder Marker |
| EP1223197B1 (en) | 2001-01-03 | 2012-08-08 | Visen Medical, Inc. | Symmetric, monofunctionalised polymethine dyes labelling reagents |
| EP1221465A1 (en) | 2001-01-03 | 2002-07-10 | Innosense S.r.l. | Symmetric, monofunctionalised polymethine dyes labelling reagents |
| EP1781675B1 (en) | 2004-08-13 | 2014-03-26 | Epoch Biosciences, Inc. | Phosphonate fluorescent dyes and conjugates |
| US7419511B2 (en) * | 2004-09-13 | 2008-09-02 | L'oreal, S.A. | Compositions comprising at least one substituted carbocyanin derivative, processes for treating keratin fibers using them, device therefor and uses thereof |
| US7427301B2 (en) | 2004-09-13 | 2008-09-23 | L'ORéAL S.A. | Composition comprising at least one substituted carbocyanin derivative, process for treating keratin fibers using it, device therefor and use thereof |
| US7425221B2 (en) | 2004-09-13 | 2008-09-16 | L'oreal S.A. | Composition comprising at least one substituted derivative of carbocyanine, method for treating keratin fibers using it, device and use |
| FR2875131B1 (fr) * | 2004-09-13 | 2007-09-28 | Oreal | Composition comprenant au moins un derive substitue de carbocyanine, procede de traitement des fibres keratiniques la mettant en oeuvre, dispositif et utilisation |
| EP1794237A2 (en) | 2004-09-30 | 2007-06-13 | GE Healthcare UK Limited | Fluorescent nucleotide analogues |
| US7282373B2 (en) | 2004-12-23 | 2007-10-16 | Rutgers, The State University Of New Jersey | Ultra-high specificity fluorescent labeling |
| US7381572B2 (en) | 2004-12-23 | 2008-06-03 | Rutgers, The State University Of New Jersey | Reagents and procedures for multi-label high-specificity labeling |
| EP1846754A4 (en) * | 2005-02-01 | 2008-10-08 | Sigma Aldrich Co | Detection of polyaminoacids via trimethylphenin staining |
| US7737281B2 (en) * | 2005-05-24 | 2010-06-15 | Enzo Life Sciences, Inc. C/O Enzo Biochem, Inc. | Purine based fluorescent dyes |
| US7569695B2 (en) * | 2005-05-24 | 2009-08-04 | Enzo Life Sciences, Inc. | Dyes for the detection or quantification of desirable target molecules |
| US8357801B2 (en) | 2005-05-24 | 2013-01-22 | Enzo Life Sciences, Inc. | Labeling of target molecules, identification of organelles and other applications, novel compositions, methods and kits |
| CN101296927A (zh) | 2005-09-02 | 2008-10-29 | Visen医药公司 | 生物相容的含n,n-二取代磺酰胺的荧光染料标记 |
| US7947256B2 (en) | 2005-09-02 | 2011-05-24 | Visen Medical, Inc. | Biocompatible fluorescent imaging agents |
| JP5416970B2 (ja) | 2005-09-02 | 2014-02-12 | ビセン メディカル， インコーポレイテッド | ニコチン酸及びピコリン酸誘導近赤外線蛍光団 |
| US7972789B2 (en) * | 2005-11-28 | 2011-07-05 | Dako Denmark A/S | Dye compounds |
| US9334281B2 (en) * | 2008-09-08 | 2016-05-10 | Enzo Life Sciences, Inc. | Fluorochromes for organelle tracing and multi-color imaging |
| US9250249B2 (en) | 2008-09-08 | 2016-02-02 | Enzo Biochem, Inc. | Autophagy and phospholipidosis pathway assays |
| AU2010219097A1 (en) | 2009-01-13 | 2011-08-04 | Glaxo Group Limited | Pyrimidinecarboxamide derivatives as inhibitors of SYK kinase |
| GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
| EP2831587B1 (en) | 2012-03-27 | 2018-05-16 | Ventana Medical Systems, Inc. | Signaling conjugates and methods of use |
| KR102502117B1 (ko) * | 2015-07-16 | 2023-02-22 | 에스에프씨 주식회사 | 염료 화합물 |
| EP3655408B1 (en) | 2017-08-24 | 2021-07-14 | The U.S.A. As Represented By The Secretary, Department Of Health And Human Services | Conformational restriction of cyanine fluorophores in far-red and near-ir range |
| KR102777649B1 (ko) * | 2017-11-23 | 2025-03-11 | 에스에프씨 주식회사 | 표지용 염료 및 이를 포함하는 표지용 키트 |
| KR102593166B1 (ko) * | 2017-11-23 | 2023-10-25 | 에스에프씨 주식회사 | 표지용 염료 및 이를 포함하는 표지용 키트 |
| AU2019300169A1 (en) | 2018-07-13 | 2021-01-28 | Quantum-Si Incorporated | Biconjugatable labels and methods of use |
| KR102682109B1 (ko) * | 2022-02-10 | 2024-07-05 | 에스에프씨 주식회사 | 신규한 화합물 및 이의 용도 |
| EP4665402A1 (en) | 2023-02-17 | 2025-12-24 | Danmarks Tekniske Universitet | Copolymer-drug conjugate for treatment of tumours |
| WO2025144711A1 (en) * | 2023-12-29 | 2025-07-03 | Illumina, Inc. | Tricyclic polymethine dyes for nucleic acid sequencing |
| CN119285524B (zh) * | 2024-10-11 | 2026-04-10 | 深圳大学 | 一种荧光染料化合物及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3753721A (en) | 1970-08-13 | 1973-08-21 | Eastman Kodak Co | Photographic materials |
| US3915715A (en) | 1970-08-13 | 1975-10-28 | Eastman Kodak Co | Silver halide photographic materials containing a high weight ratio of gold to sulfur sensitizers and a sensitizing methine dye |
| US3679427A (en) * | 1970-10-30 | 1972-07-25 | Eastman Kodak Co | Rigidized carbocyanine dyes and photographic emulsions |
| US3854956A (en) | 1970-10-30 | 1974-12-17 | Eastman Kodak Co | Dyestuffs and spectral sensitizers for silver halide |
| US3821233A (en) | 1970-10-30 | 1974-06-28 | Eastman Kodak Co | Rigidized carbocyanine dyes containing a pyrida-dipyridinium nucleus |
| US3864644A (en) * | 1971-03-22 | 1975-02-04 | Eastman Kodak Co | Dye lasers including rigidized carbocyanine dyes |
| CA985493A (en) * | 1971-03-22 | 1976-03-16 | Eastman Kodak Company | Dye lasers including rigidized carbocyanine dyes |
| US3904637A (en) | 1972-04-19 | 1975-09-09 | Eastman Kodak Co | 7'a'h,8'a'h-bisbenzothiazolo(3,2-a;-3',2'-a)pyrano (3,2-c;5,6-c'+9 dipyridinium compounds and related derivatives thereof |
| DE69624623T2 (de) | 1995-06-07 | 2003-07-24 | Carnegie Mellon University, Pittsburgh | Versteifte Monomethin-Cyaninfarbstoffe |
| US5658735A (en) | 1995-11-09 | 1997-08-19 | Biometric Imaging, Inc. | Cyclized fluorescent nucleic acid intercalating cyanine dyes and nucleic acid detection methods |
| US6133445A (en) | 1997-12-17 | 2000-10-17 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
-
1998
- 1998-12-16 ES ES98963218T patent/ES2165711T3/es not_active Expired - Lifetime
- 1998-12-16 EP EP98963218A patent/EP1042407B1/en not_active Expired - Lifetime
- 1998-12-16 DE DE69801682T patent/DE69801682T2/de not_active Expired - Lifetime
- 1998-12-16 AT AT98963218T patent/ATE205515T1/de active
- 1998-12-16 AU AU18288/99A patent/AU760598B2/en not_active Expired
- 1998-12-16 DK DK98963218T patent/DK1042407T3/da active
- 1998-12-16 CA CA002314188A patent/CA2314188C/en not_active Expired - Lifetime
- 1998-12-16 WO PCT/US1998/026665 patent/WO1999031181A1/en not_active Ceased
- 1998-12-16 US US09/581,679 patent/US6686145B1/en not_active Expired - Lifetime
- 1998-12-16 JP JP2000539092A patent/JP4927253B2/ja not_active Expired - Lifetime
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