DE69923859T2 - Porphyrin-Verbindungen, ihre Konjugate und Testmethoden basierend auf der Verwendung besagter Konjugate - Google Patents
Porphyrin-Verbindungen, ihre Konjugate und Testmethoden basierend auf der Verwendung besagter Konjugate Download PDFInfo
- Publication number
- DE69923859T2 DE69923859T2 DE69923859T DE69923859T DE69923859T2 DE 69923859 T2 DE69923859 T2 DE 69923859T2 DE 69923859 T DE69923859 T DE 69923859T DE 69923859 T DE69923859 T DE 69923859T DE 69923859 T2 DE69923859 T2 DE 69923859T2
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- Germany
- Prior art keywords
- compound
- group
- compound according
- solution
- coproporphyrin
- 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 - Lifetime
Links
- -1 Porphyrin compounds Chemical class 0.000 title description 28
- 238000010998 test method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 102000004169 proteins and genes Human genes 0.000 claims description 13
- 108090000623 proteins and genes Proteins 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 11
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 9
- 108020004707 nucleic acids Proteins 0.000 claims description 8
- 102000039446 nucleic acids Human genes 0.000 claims description 8
- 150000007523 nucleic acids Chemical class 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 7
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical group [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 7
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical group [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 6
- 108091034117 Oligonucleotide Proteins 0.000 claims description 5
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 5
- 229920001184 polypeptide Polymers 0.000 claims description 5
- 108091033319 polynucleotide Proteins 0.000 claims description 4
- 102000040430 polynucleotide Human genes 0.000 claims description 4
- 239000002157 polynucleotide Substances 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 150000004676 glycans Chemical class 0.000 claims description 3
- 239000003550 marker Substances 0.000 claims description 3
- 239000002773 nucleotide Substances 0.000 claims description 3
- 125000003729 nucleotide group Chemical group 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920001282 polysaccharide Polymers 0.000 claims description 3
- 239000005017 polysaccharide Substances 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 4
- 239000012634 fragment Substances 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000012491 analyte Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000002380 cytological effect Effects 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 55
- 238000002372 labelling Methods 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000003153 chemical reaction reagent Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 39
- 150000002148 esters Chemical class 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- 150000004032 porphyrins Chemical class 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000975 dye Substances 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 150000001718 carbodiimides Chemical class 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 238000003018 immunoassay Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000001994 activation Methods 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 125000006850 spacer group Chemical group 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000005119 centrifugation Methods 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- VORBHEGMEBOMMB-UHFFFAOYSA-N coproporphyrin i Chemical compound N1C(C=C2C(=C(CCC(O)=O)C(C=C3C(=C(CCC(O)=O)C(=C4)N3)C)=N2)C)=C(CCC(O)=O)C(C)=C1C=C1C(CCC(O)=O)=C(C)C4=N1 VORBHEGMEBOMMB-UHFFFAOYSA-N 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- VCQURUZYYSOUHP-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 2,2,2-trifluoroacetate Chemical compound FC1=C(F)C(F)=C(OC(=O)C(F)(F)F)C(F)=C1F VCQURUZYYSOUHP-UHFFFAOYSA-N 0.000 description 6
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 229940127573 compound 38 Drugs 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 4
- ZITKOZNFNXRJIX-UHFFFAOYSA-N 2-amino-n-[2-(4-aminophenyl)ethyl]acetamide Chemical compound NCC(=O)NCCC1=CC=C(N)C=C1 ZITKOZNFNXRJIX-UHFFFAOYSA-N 0.000 description 4
- LNPMZQXEPNWCMG-UHFFFAOYSA-N 4-(2-aminoethyl)aniline Chemical compound NCCC1=CC=C(N)C=C1 LNPMZQXEPNWCMG-UHFFFAOYSA-N 0.000 description 4
- 229940126657 Compound 17 Drugs 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 101150003085 Pdcl gene Proteins 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 4
- 150000002540 isothiocyanates Chemical class 0.000 description 4
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
- PLEQQUFEIPMIHA-UHFFFAOYSA-N 3-[8,12,18-tris(2-carboxyethyl)-3,7,13,17-tetramethyl-21,22-dihydroporphyrin-2-yl]propanoic acid Chemical compound N1C(C=C2C(=C(CCC(O)=O)C(=CC=3C(=C(C)C(=C4)N=3)CCC(O)=O)N2)C)=C(C)C(CCC(O)=O)=C1C=C1C(CCC(O)=O)=C(C)C4=N1 PLEQQUFEIPMIHA-UHFFFAOYSA-N 0.000 description 3
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- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 3
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- 125000003636 chemical group Chemical group 0.000 description 3
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
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- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 3
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- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
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- VDSJDIBBSGUGOE-UHFFFAOYSA-N [N]1C2=CC=C1C=C(N1)C=C(C(=O)O)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 Chemical compound [N]1C2=CC=C1C=C(N1)C=C(C(=O)O)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 VDSJDIBBSGUGOE-UHFFFAOYSA-N 0.000 description 1
- IXPCJOPIVIEBBA-UHFFFAOYSA-N [Pt+2].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical class [Pt+2].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 IXPCJOPIVIEBBA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002036 chloroform fraction Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000004163 cytometry Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
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- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 229940127121 immunoconjugate Drugs 0.000 description 1
- 238000012744 immunostaining Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical compound N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000000013 phosphorescence detection Methods 0.000 description 1
- 238000000241 photoluminescence detection Methods 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI982422A FI982422A0 (fi) | 1998-11-09 | 1998-11-09 | Porfyriiniyhdisteitä, niiden konjugaatit sekä määritysmenetelmiä pohjautuen näiden konjugaattien käyttöön |
| FI982422 | 1998-11-09 | ||
| PCT/FI1999/000898 WO2000027847A1 (en) | 1998-11-09 | 1999-10-27 | Porphyrin compounds, their conjugates and assay methods based on the use of said conjugates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69923859D1 DE69923859D1 (de) | 2005-03-31 |
| DE69923859T2 true DE69923859T2 (de) | 2006-04-13 |
Family
ID=8552872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69923859T Expired - Lifetime DE69923859T2 (de) | 1998-11-09 | 1999-10-27 | Porphyrin-Verbindungen, ihre Konjugate und Testmethoden basierend auf der Verwendung besagter Konjugate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6582930B1 (enExample) |
| EP (1) | EP1129092B1 (enExample) |
| JP (1) | JP4195200B2 (enExample) |
| DE (1) | DE69923859T2 (enExample) |
| FI (1) | FI982422A0 (enExample) |
| WO (1) | WO2000027847A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60131070T2 (de) | 2001-05-28 | 2008-08-07 | Kreatech Biotechnology B.V. | Ein Verfahren zur differentiellen Markierung mittels Platin-Komplexen |
| EP1265144B1 (en) * | 2001-06-08 | 2006-03-29 | Hewlett-Packard Company | Method and apparatus for providing remote support to a computer user |
| US20030119203A1 (en) | 2001-12-24 | 2003-06-26 | Kimberly-Clark Worldwide, Inc. | Lateral flow assay devices and methods for conducting assays |
| US8367013B2 (en) | 2001-12-24 | 2013-02-05 | Kimberly-Clark Worldwide, Inc. | Reading device, method, and system for conducting lateral flow assays |
| US7223534B2 (en) * | 2002-05-03 | 2007-05-29 | Kimberly-Clark Worldwide, Inc. | Diffraction-based diagnostic devices |
| US7118855B2 (en) | 2002-05-03 | 2006-10-10 | Kimberly-Clark Worldwide, Inc. | Diffraction-based diagnostic devices |
| US7223368B2 (en) * | 2002-05-03 | 2007-05-29 | Kimberly-Clark Worldwide, Inc. | Diffraction-based diagnostic devices |
| US7214530B2 (en) * | 2002-05-03 | 2007-05-08 | Kimberly-Clark Worldwide, Inc. | Biomolecule diagnostic devices and method for producing biomolecule diagnostic devices |
| US7485453B2 (en) | 2002-05-03 | 2009-02-03 | Kimberly-Clark Worldwide, Inc. | Diffraction-based diagnostic devices |
| US7771922B2 (en) * | 2002-05-03 | 2010-08-10 | Kimberly-Clark Worldwide, Inc. | Biomolecule diagnostic device |
| US7091049B2 (en) * | 2002-06-26 | 2006-08-15 | Kimberly-Clark Worldwide, Inc. | Enhanced diffraction-based biosensor devices |
| US7285424B2 (en) | 2002-08-27 | 2007-10-23 | Kimberly-Clark Worldwide, Inc. | Membrane-based assay devices |
| US7314763B2 (en) | 2002-08-27 | 2008-01-01 | Kimberly-Clark Worldwide, Inc. | Fluidics-based assay devices |
| US7432105B2 (en) | 2002-08-27 | 2008-10-07 | Kimberly-Clark Worldwide, Inc. | Self-calibration system for a magnetic binding assay |
| US7169550B2 (en) | 2002-09-26 | 2007-01-30 | Kimberly-Clark Worldwide, Inc. | Diffraction-based diagnostic devices |
| US7781172B2 (en) | 2003-11-21 | 2010-08-24 | Kimberly-Clark Worldwide, Inc. | Method for extending the dynamic detection range of assay devices |
| US7247500B2 (en) * | 2002-12-19 | 2007-07-24 | Kimberly-Clark Worldwide, Inc. | Reduction of the hook effect in membrane-based assay devices |
| GB2397067B (en) * | 2002-12-23 | 2005-05-11 | Destiny Pharma Ltd | Porphin & azaporphin derivatives with at least one cationic-nitrogen-containing meso-substituent for use in photodynamic therapy & in vitro sterilisation |
| US7138520B2 (en) | 2003-01-13 | 2006-11-21 | Massachusetts Institute Of Technology | Coordination complexes having tethered therapeutic agents and/or targeting moieties, and methods of making and using the same |
| WO2004079349A1 (en) * | 2003-03-07 | 2004-09-16 | Luxcel Biosciences Limited | An oxygen sensitive probe |
| US7851209B2 (en) | 2003-04-03 | 2010-12-14 | Kimberly-Clark Worldwide, Inc. | Reduction of the hook effect in assay devices |
| US20040197819A1 (en) | 2003-04-03 | 2004-10-07 | Kimberly-Clark Worldwide, Inc. | Assay devices that utilize hollow particles |
| EP1484682B1 (en) | 2003-06-02 | 2012-12-05 | Hewlett-Packard Development Company, L.P. | Method and apparatus for providing support for an electronic device |
| US7943395B2 (en) | 2003-11-21 | 2011-05-17 | Kimberly-Clark Worldwide, Inc. | Extension of the dynamic detection range of assay devices |
| US7713748B2 (en) | 2003-11-21 | 2010-05-11 | Kimberly-Clark Worldwide, Inc. | Method of reducing the sensitivity of assay devices |
| US20050112703A1 (en) | 2003-11-21 | 2005-05-26 | Kimberly-Clark Worldwide, Inc. | Membrane-based lateral flow assay devices that utilize phosphorescent detection |
| US7943089B2 (en) | 2003-12-19 | 2011-05-17 | Kimberly-Clark Worldwide, Inc. | Laminated assay devices |
| EP1716252A1 (en) * | 2004-02-19 | 2006-11-02 | University College Cork-National University of Ireland, Cork | Detection of biologically active compounds |
| US7486815B2 (en) * | 2004-02-20 | 2009-02-03 | Microsoft Corporation | Method and apparatus for scene learning and three-dimensional tracking using stereo video cameras |
| US7247375B2 (en) * | 2004-04-30 | 2007-07-24 | Kimberly-Clark Worldwide, Inc. | Polymeric matrices for the encapsulation of phosphorescent molecules for analytical applications |
| US20060019265A1 (en) * | 2004-04-30 | 2006-01-26 | Kimberly-Clark Worldwide, Inc. | Transmission-based luminescent detection systems |
| US7815854B2 (en) * | 2004-04-30 | 2010-10-19 | Kimberly-Clark Worldwide, Inc. | Electroluminescent illumination source for optical detection systems |
| US7796266B2 (en) * | 2004-04-30 | 2010-09-14 | Kimberly-Clark Worldwide, Inc. | Optical detection system using electromagnetic radiation to detect presence or quantity of analyte |
| GB2415372A (en) | 2004-06-23 | 2005-12-28 | Destiny Pharma Ltd | Non photodynamical or sonodynamical antimicrobial use of porphyrins and azaporphyrins containing at least one cationic-nitrogen-containing substituent |
| US7238301B2 (en) * | 2004-06-29 | 2007-07-03 | Kimberly-Clark Worldwide, Inc. | Cross-linked encapsulated phosphorescent molecules |
| US7094528B2 (en) * | 2004-06-30 | 2006-08-22 | Kimberly-Clark Worldwide, Inc. | Magnetic enzyme detection techniques |
| US7906276B2 (en) | 2004-06-30 | 2011-03-15 | Kimberly-Clark Worldwide, Inc. | Enzymatic detection techniques |
| US7521226B2 (en) | 2004-06-30 | 2009-04-21 | Kimberly-Clark Worldwide, Inc. | One-step enzymatic and amine detection technique |
| US7939342B2 (en) | 2005-03-30 | 2011-05-10 | Kimberly-Clark Worldwide, Inc. | Diagnostic test kits employing an internal calibration system |
| US7858384B2 (en) * | 2005-04-29 | 2010-12-28 | Kimberly-Clark Worldwide, Inc. | Flow control technique for assay devices |
| US7439079B2 (en) * | 2005-04-29 | 2008-10-21 | Kimberly-Clark Worldwide, Inc. | Assay devices having detection capabilities within the hook effect region |
| US7803319B2 (en) * | 2005-04-29 | 2010-09-28 | Kimberly-Clark Worldwide, Inc. | Metering technique for lateral flow assay devices |
| US7504235B2 (en) | 2005-08-31 | 2009-03-17 | Kimberly-Clark Worldwide, Inc. | Enzyme detection technique |
| US7829347B2 (en) * | 2005-08-31 | 2010-11-09 | Kimberly-Clark Worldwide, Inc. | Diagnostic test kits with improved detection accuracy |
| US20070141597A1 (en) * | 2005-10-25 | 2007-06-21 | Harmon H J | Biomimetic Biodetector of Toxins, Viruses, Bacteria, and Biological Factors |
| US7279136B2 (en) | 2005-12-13 | 2007-10-09 | Takeuchi James M | Metering technique for lateral flow assay devices |
| US7645583B2 (en) * | 2005-12-14 | 2010-01-12 | Kimberly-Clark Worldwide, Inc. | Identification of compounds for inhibiting complexation of C-reactive protein with fibronectin |
| US7745158B2 (en) | 2005-12-14 | 2010-06-29 | Kimberly-Clark Worldwide, Inc. | Detection of secreted aspartyl proteases from Candida species |
| US7618810B2 (en) * | 2005-12-14 | 2009-11-17 | Kimberly-Clark Worldwide, Inc. | Metering strip and method for lateral flow assay devices |
| US8758989B2 (en) * | 2006-04-06 | 2014-06-24 | Kimberly-Clark Worldwide, Inc. | Enzymatic detection techniques |
| US20080051646A1 (en) * | 2006-07-24 | 2008-02-28 | Papkovsky Dmitri B | Probe for cellular oxygen |
| US7897360B2 (en) | 2006-12-15 | 2011-03-01 | Kimberly-Clark Worldwide, Inc. | Enzyme detection techniques |
| US8535617B2 (en) * | 2007-11-30 | 2013-09-17 | Kimberly-Clark Worldwide, Inc. | Blood cell barrier for a lateral flow device |
| CN102707056B (zh) * | 2012-04-28 | 2015-01-28 | 广州鸿琪光学仪器科技有限公司 | 快速定量检测心肌肌酸激酶同工酶的免疫荧光试纸条组件及其制成的检测卡组件和制备方法 |
| CN102866251A (zh) * | 2012-06-19 | 2013-01-09 | 深圳市艾瑞生物科技有限公司 | 基于磷光发光技术的免疫荧光试纸条及其制备方法和应用 |
| WO2017139679A1 (en) | 2016-02-12 | 2017-08-17 | The Regents Of The University Of California | Systems and compositions for diagnosing pathogenic fungal infection and methods of using the same |
| WO2017165665A1 (en) | 2016-03-23 | 2017-09-28 | The General Hospital Corporation | Assays and methods for detecting udp-glucose |
| EP3607320A4 (en) | 2017-04-03 | 2021-04-21 | The Regents of the University of California | COMPOSITIONS AND METHODS OF DIAGNOSING Pancreatic Cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3827940A1 (de) * | 1988-08-13 | 1990-03-01 | Schering Ag | 13,17-propionsaeure- und propionsaeurederivat- substituierte porphyrin-komplexverbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE69418329D1 (de) * | 1994-10-07 | 1999-06-10 | Joanneum Research Forschungsge | Lumineszente Farbstoffe, aktive Elementen auf deren Grundlage und Messverfahren für die Sauerstoffkonzentration diese lumineszenten Farbstoffe benutzend |
| EP0811626B1 (en) * | 1996-06-04 | 2002-08-14 | Roche Diagnostics GmbH | Use of metallo-porphyrin conjugates for the detection of biological substances |
| DE69725851T2 (de) | 1996-07-22 | 2004-09-02 | Novartis Ag | Lichtempfindliche zusammensetzungen für sauerstoffoptroden |
-
1998
- 1998-11-09 FI FI982422A patent/FI982422A0/fi unknown
-
1999
- 1999-10-27 EP EP99954031A patent/EP1129092B1/en not_active Expired - Lifetime
- 1999-10-27 JP JP2000581025A patent/JP4195200B2/ja not_active Expired - Lifetime
- 1999-10-27 DE DE69923859T patent/DE69923859T2/de not_active Expired - Lifetime
- 1999-10-27 WO PCT/FI1999/000898 patent/WO2000027847A1/en not_active Ceased
-
2001
- 2001-04-20 US US09/807,866 patent/US6582930B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI982422A0 (fi) | 1998-11-09 |
| WO2000027847A1 (en) | 2000-05-18 |
| EP1129092A1 (en) | 2001-09-05 |
| DE69923859D1 (de) | 2005-03-31 |
| JP4195200B2 (ja) | 2008-12-10 |
| EP1129092B1 (en) | 2005-02-23 |
| JP2002529466A (ja) | 2002-09-10 |
| US6582930B1 (en) | 2003-06-24 |
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