JP2007500192A5 - - Google Patents
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- JP2007500192A5 JP2007500192A5 JP2006521968A JP2006521968A JP2007500192A5 JP 2007500192 A5 JP2007500192 A5 JP 2007500192A5 JP 2006521968 A JP2006521968 A JP 2006521968A JP 2006521968 A JP2006521968 A JP 2006521968A JP 2007500192 A5 JP2007500192 A5 JP 2007500192A5
- Authority
- JP
- Japan
- Prior art keywords
- polymersome
- coumarin
- poly
- agent
- radioactive
- 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.)
- Pending
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- 229920000575 polymersome Polymers 0.000 claims description 165
- 230000002285 radioactive effect Effects 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 38
- 238000009739 binding Methods 0.000 claims description 32
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 28
- -1 hexaphylline Chemical compound 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 24
- 150000004032 porphyrins Chemical group 0.000 claims description 24
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 22
- 239000012528 membrane Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 14
- 229920001223 polyethylene glycol Polymers 0.000 claims description 13
- 210000004027 cell Anatomy 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- 238000001727 in vivo Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 102000004169 proteins and genes Human genes 0.000 claims description 6
- 108090000623 proteins and genes Proteins 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 5
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 238000003384 imaging method Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 150000003904 phospholipids Chemical class 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 210000001519 tissue Anatomy 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 239000012620 biological material Substances 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 62
- 150000001875 compounds Chemical class 0.000 claims 38
- 229920001477 hydrophilic polymer Polymers 0.000 claims 38
- 229920000469 amphiphilic block copolymer Polymers 0.000 claims 37
- 229920001600 hydrophobic polymer Polymers 0.000 claims 28
- 239000012216 imaging agent Substances 0.000 claims 26
- 239000008194 pharmaceutical composition Substances 0.000 claims 23
- 241000894007 species Species 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 17
- 239000000178 monomer Substances 0.000 claims 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 11
- 239000000990 laser dye Substances 0.000 claims 11
- 108090000765 processed proteins & peptides Proteins 0.000 claims 11
- 230000002209 hydrophobic effect Effects 0.000 claims 10
- 229920000747 poly(lactic acid) Polymers 0.000 claims 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 9
- 239000002777 nucleoside Substances 0.000 claims 9
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 9
- 102000005962 receptors Human genes 0.000 claims 9
- 108020003175 receptors Proteins 0.000 claims 9
- 239000000975 dye Substances 0.000 claims 8
- 239000004215 Carbon black (E152) Substances 0.000 claims 7
- 229930195733 hydrocarbon Natural products 0.000 claims 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 7
- 230000003595 spectral effect Effects 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 125000005282 allenyl group Chemical group 0.000 claims 6
- 150000001720 carbohydrates Chemical class 0.000 claims 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 6
- 229920001610 polycaprolactone Polymers 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000002430 hydrocarbons Chemical group 0.000 claims 5
- 150000002632 lipids Chemical class 0.000 claims 5
- KMVYGTIPJNGNRD-GKAPJAKFSA-N (2s)-2-amino-3-benzylbutanedioic acid Chemical compound OC(=O)[C@@H](N)C(C(O)=O)CC1=CC=CC=C1 KMVYGTIPJNGNRD-GKAPJAKFSA-N 0.000 claims 4
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 claims 4
- HMSMOZAIMDNRBW-UHFFFAOYSA-N 100572-96-1 Chemical group C1=CC2=NC1=CC=C(N1)C=CC1=C(N1)C=CC1=CC=C1C=CC2=N1 HMSMOZAIMDNRBW-UHFFFAOYSA-N 0.000 claims 4
- 108010003118 Bacteriochlorophylls Proteins 0.000 claims 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 239000004793 Polystyrene Substances 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- DSJXIQQMORJERS-AGGZHOMASA-M bacteriochlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC([C@H](CC)[C@H]3C)=[N+]4C3=CC3=C(C(C)=O)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 DSJXIQQMORJERS-AGGZHOMASA-M 0.000 claims 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 4
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 claims 4
- 229930002875 chlorophyll Natural products 0.000 claims 4
- 235000019804 chlorophyll Nutrition 0.000 claims 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 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 229940127089 cytotoxic agent Drugs 0.000 claims 4
- 239000002254 cytotoxic agent Substances 0.000 claims 4
- 231100000599 cytotoxic agent Toxicity 0.000 claims 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims 4
- MOFVSTNWEDAEEK-UHFFFAOYSA-M indocyanine green Chemical compound [Na+].[O-]S(=O)(=O)CCCCN1C2=CC=C3C=CC=CC3=C2C(C)(C)C1=CC=CC=CC=CC1=[N+](CCCCS([O-])(=O)=O)C2=CC=C(C=CC=C3)C3=C2C1(C)C MOFVSTNWEDAEEK-UHFFFAOYSA-M 0.000 claims 4
- 238000004020 luminiscence type Methods 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- 150000002894 organic compounds Chemical class 0.000 claims 4
- 230000002165 photosensitisation Effects 0.000 claims 4
- 239000003504 photosensitizing agent Substances 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- 229920000933 poly (ε-caprolactam) Polymers 0.000 claims 4
- 229920001451 polypropylene glycol Polymers 0.000 claims 4
- 229920002223 polystyrene Polymers 0.000 claims 4
- 238000002600 positron emission tomography Methods 0.000 claims 4
- COFLCBMDHTVQRA-UHFFFAOYSA-N sapphyrin Chemical compound N1C(C=2NC(C=C3N=C(C=C4NC(=C5)C=C4)C=C3)=CC=2)=CC=C1C=C1C=CC5=N1 COFLCBMDHTVQRA-UHFFFAOYSA-N 0.000 claims 4
- 238000002560 therapeutic procedure Methods 0.000 claims 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 4
- QVHVXEVQPNDOFD-UHFFFAOYSA-M (2e)-1,1,3-trimethyl-2-[(2e)-7-(1,1,3-trimethylbenzo[e]indol-3-ium-2-yl)hepta-2,4,6-trienylidene]benzo[e]indole;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC2=CC=CC=C2C(C2(C)C)=C1N(C)\C2=C\C=C\C=C\C=C\C1=[N+](C)C2=CC=C(C=CC=C3)C3=C2C1(C)C QVHVXEVQPNDOFD-UHFFFAOYSA-M 0.000 claims 3
- NHQOULZCPKJYMM-UHFFFAOYSA-M (2e)-1,3,3-trimethyl-2-[(2e)-7-(1,3,3-trimethylindol-1-ium-2-yl)hepta-2,4,6-trienylidene]indole;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC1(C)C2=CC=CC=C2N(C)C1=CC=CC=CC=CC1=[N+](C)C2=CC=CC=C2C1(C)C NHQOULZCPKJYMM-UHFFFAOYSA-M 0.000 claims 3
- UANMYOBKUNUUTR-UHFFFAOYSA-M (2z)-1,3,3-trimethyl-2-[(2e)-5-(1,3,3-trimethylindol-1-ium-2-yl)penta-2,4-dienylidene]indole;iodide Chemical compound [I-].CC1(C)C2=CC=CC=C2N(C)C1=CC=CC=CC1=[N+](C)C2=CC=CC=C2C1(C)C UANMYOBKUNUUTR-UHFFFAOYSA-M 0.000 claims 3
- JKXWXYURKUEZHV-UHFFFAOYSA-M (2z)-1,3,3-trimethyl-2-[(2e)-7-(1,3,3-trimethylindol-1-ium-2-yl)hepta-2,4,6-trienylidene]indole;iodide Chemical compound [I-].CC1(C)C2=CC=CC=C2N(C)C1=CC=CC=CC=CC1=[N+](C)C2=CC=CC=C2C1(C)C JKXWXYURKUEZHV-UHFFFAOYSA-M 0.000 claims 3
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims 3
- VFNKZQNIXUFLBC-UHFFFAOYSA-N 2',7'-dichlorofluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(O)C=C1OC1=C2C=C(Cl)C(O)=C1 VFNKZQNIXUFLBC-UHFFFAOYSA-N 0.000 claims 3
- JNGRENQDBKMCCR-UHFFFAOYSA-N 2-(3-amino-6-iminoxanthen-9-yl)benzoic acid;hydrochloride Chemical compound [Cl-].C=12C=CC(=[NH2+])C=C2OC2=CC(N)=CC=C2C=1C1=CC=CC=C1C(O)=O JNGRENQDBKMCCR-UHFFFAOYSA-N 0.000 claims 3
- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 claims 3
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims 3
- PZTQNUMZYIQRGY-UHFFFAOYSA-N 4-methyl-6,7,8,9-tetrahydropyrano[3,2-g]quinolin-2-one Chemical compound C1=C2NCCCC2=CC2=C1OC(=O)C=C2C PZTQNUMZYIQRGY-UHFFFAOYSA-N 0.000 claims 3
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 claims 3
- RIUSGHALMCFISX-UHFFFAOYSA-N 7-(dimethylamino)-2,3-dihydro-1h-cyclopenta[c]chromen-4-one Chemical compound O=C1OC2=CC(N(C)C)=CC=C2C2=C1CCC2 RIUSGHALMCFISX-UHFFFAOYSA-N 0.000 claims 3
- QZXAEJGHNXJTSE-UHFFFAOYSA-N 7-(ethylamino)-4,6-dimethylchromen-2-one Chemical compound O1C(=O)C=C(C)C2=C1C=C(NCC)C(C)=C2 QZXAEJGHNXJTSE-UHFFFAOYSA-N 0.000 claims 3
- NRZJOTSUPLCYDJ-UHFFFAOYSA-N 7-(ethylamino)-6-methyl-4-(trifluoromethyl)chromen-2-one Chemical compound O1C(=O)C=C(C(F)(F)F)C2=C1C=C(NCC)C(C)=C2 NRZJOTSUPLCYDJ-UHFFFAOYSA-N 0.000 claims 3
- JBNOVHJXQSHGRL-UHFFFAOYSA-N 7-amino-4-(trifluoromethyl)coumarin Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N)=CC=C21 JBNOVHJXQSHGRL-UHFFFAOYSA-N 0.000 claims 3
- MJXYFLJHTUSJGU-UHFFFAOYSA-N 7-amino-4-methyl-1h-quinolin-2-one Chemical compound NC1=CC=C2C(C)=CC(=O)NC2=C1 MJXYFLJHTUSJGU-UHFFFAOYSA-N 0.000 claims 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 3
- CLDZYSUDOQXJOU-UHFFFAOYSA-M C5-oxacyanine Chemical compound [I-].O1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2O1 CLDZYSUDOQXJOU-UHFFFAOYSA-M 0.000 claims 3
- 239000004971 Cross linker Substances 0.000 claims 3
- 108010021625 Immunoglobulin Fragments Proteins 0.000 claims 3
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims 3
- 108091093037 Peptide nucleic acid Proteins 0.000 claims 3
- IEBFEMIXXHIISM-YZOUKVLTSA-N Rosarin Chemical compound O[C@@H]1[C@@H](O)[C@H](CO)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC\C=C\C=2C=CC=CC=2)O1 IEBFEMIXXHIISM-YZOUKVLTSA-N 0.000 claims 3
- IEBFEMIXXHIISM-XZDFAHJYSA-N Rosarin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO[C@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O2)O1 IEBFEMIXXHIISM-XZDFAHJYSA-N 0.000 claims 3
- GOVKLKKLYMXKNS-ZCSGCDBXSA-N [3-hexadecanoyloxy-2-[7-[2-[4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-1-tritioethoxy]heptanoyloxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound C1=CC(CC([3H])OCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C)=CC=C1C1(C(F)(F)F)N=N1 GOVKLKKLYMXKNS-ZCSGCDBXSA-N 0.000 claims 3
- OUAWJLNOTQAOHL-UHFFFAOYSA-N [9-(diethylamino)benzo[a]phenoxazin-5-ylidene]azanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=[NH2+])C2=C1 OUAWJLNOTQAOHL-UHFFFAOYSA-N 0.000 claims 3
- WOUDGKCAYZSDQC-UHFFFAOYSA-N [9-(dimethylamino)-10-methylbenzo[a]phenoxazin-5-ylidene]azanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.O1C2=CC(=[NH2+])C3=CC=CC=C3C2=NC2=C1C=C(N(C)C)C(C)=C2 WOUDGKCAYZSDQC-UHFFFAOYSA-N 0.000 claims 3
- 239000000298 carbocyanine Substances 0.000 claims 3
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 claims 3
- 229960000956 coumarin Drugs 0.000 claims 3
- 235000001671 coumarin Nutrition 0.000 claims 3
- LLSRPENMALNOFW-UHFFFAOYSA-N coumarin 106 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C2=C1CCC2 LLSRPENMALNOFW-UHFFFAOYSA-N 0.000 claims 3
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 claims 3
- KDTAEYOYAZPLIC-UHFFFAOYSA-N coumarin 152 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N(C)C)=CC=C21 KDTAEYOYAZPLIC-UHFFFAOYSA-N 0.000 claims 3
- VSSSHNJONFTXHS-UHFFFAOYSA-N coumarin 153 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C=C1C(F)(F)F VSSSHNJONFTXHS-UHFFFAOYSA-N 0.000 claims 3
- JRUYYVYCSJCVMP-UHFFFAOYSA-N coumarin 30 Chemical compound C1=CC=C2N(C)C(C=3C4=CC=C(C=C4OC(=O)C=3)N(CC)CC)=NC2=C1 JRUYYVYCSJCVMP-UHFFFAOYSA-N 0.000 claims 3
- JBPCDMSEJVCNGV-UHFFFAOYSA-N coumarin 334 Chemical compound C1CCC2=C(OC(C(C(=O)C)=C3)=O)C3=CC3=C2N1CCC3 JBPCDMSEJVCNGV-UHFFFAOYSA-N 0.000 claims 3
- LGDDFMCJIHJNMK-UHFFFAOYSA-N coumarin 337 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C(C#N)=C1 LGDDFMCJIHJNMK-UHFFFAOYSA-N 0.000 claims 3
- KCDCNGXPPGQERR-UHFFFAOYSA-N coumarin 343 Chemical compound C1CCC2=C(OC(C(C(=O)O)=C3)=O)C3=CC3=C2N1CCC3 KCDCNGXPPGQERR-UHFFFAOYSA-N 0.000 claims 3
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 claims 3
- XHXMPURWMSJENN-UHFFFAOYSA-N coumarin 480 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C=C1C XHXMPURWMSJENN-UHFFFAOYSA-N 0.000 claims 3
- GZTMNDOZYLMFQE-UHFFFAOYSA-N coumarin 500 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(NCC)=CC=C21 GZTMNDOZYLMFQE-UHFFFAOYSA-N 0.000 claims 3
- VMJKUPWQKZFFCX-UHFFFAOYSA-N coumarin 504 Chemical compound C1CCC2=C(OC(C(C(=O)OCC)=C3)=O)C3=CC3=C2N1CCC3 VMJKUPWQKZFFCX-UHFFFAOYSA-N 0.000 claims 3
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 claims 3
- CEJANLKHJMMNQB-UHFFFAOYSA-M cryptocyanin Chemical compound [I-].C12=CC=CC=C2N(CC)C=CC1=CC=CC1=CC=[N+](CC)C2=CC=CC=C12 CEJANLKHJMMNQB-UHFFFAOYSA-M 0.000 claims 3
- SBOSGIJGEHWBKV-UHFFFAOYSA-L dioctyltin(2+);dichloride Chemical compound CCCCCCCC[Sn](Cl)(Cl)CCCCCCCC SBOSGIJGEHWBKV-UHFFFAOYSA-L 0.000 claims 3
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
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- 2004-07-26 CA CA002533637A patent/CA2533637A1/en not_active Abandoned
- 2004-07-26 EP EP04786113A patent/EP1659938A4/en not_active Withdrawn
- 2004-07-26 AU AU2004264877A patent/AU2004264877B2/en not_active Expired
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