JP2003532634A5 - - Google Patents
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- JP2003532634A5 JP2003532634A5 JP2001549649A JP2001549649A JP2003532634A5 JP 2003532634 A5 JP2003532634 A5 JP 2003532634A5 JP 2001549649 A JP2001549649 A JP 2001549649A JP 2001549649 A JP2001549649 A JP 2001549649A JP 2003532634 A5 JP2003532634 A5 JP 2003532634A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- alkyl
- amyloidosis
- substituted
- 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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- -1 2,3-dihydroxybenzoyl Chemical group 0.000 claims 85
- QIGMCZARMNNIKC-PNHWDRBUSA-N methyl (1R,4S,7S,11S)-4-hydroxy-2-oxa-10-azatricyclo[5.3.1.04,11]undeca-5,8-diene-8-carboxylate Chemical compound COC(=O)C1=CN[C@@H]2OC[C@@]3(O)[C@@H]2[C@@H]1C=C3 QIGMCZARMNNIKC-PNHWDRBUSA-N 0.000 claims 50
- 206010002022 amyloidosis Diseases 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 32
- 239000002253 acid Substances 0.000 claims 31
- 125000003545 alkoxy group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 30
- 125000005843 halogen group Chemical group 0.000 claims 29
- 125000001424 substituent group Chemical group 0.000 claims 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 15
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 14
- 230000002452 interceptive effect Effects 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims 12
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims 12
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N quercetagetin Chemical compound C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 10
- DANYIYRPLHHOCZ-UHFFFAOYSA-N 5,7-dihydroxy-4'-methoxyflavone Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 DANYIYRPLHHOCZ-UHFFFAOYSA-N 0.000 claims 10
- YFVNYAXYZNDLIY-UHFFFAOYSA-N 7-hydroxy-3-(3,4,5-trihydroxyphenyl)chromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC=C2C1=CC(O)=C(O)C(O)=C1 YFVNYAXYZNDLIY-UHFFFAOYSA-N 0.000 claims 10
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims 10
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 10
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- RTIXKCRFFJGDFG-UHFFFAOYSA-N chrysin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 0.000 claims 10
- ZZBWSNKBZKPGAK-UHFFFAOYSA-N chrysophanol-9-anthrone Chemical compound C1=CC=C2CC3=CC(C)=CC(O)=C3C(=O)C2=C1O ZZBWSNKBZKPGAK-UHFFFAOYSA-N 0.000 claims 10
- VEVZSMAEJFVWIL-UHFFFAOYSA-O cyanidin cation Chemical compound [O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC=C(O)C(O)=C1 VEVZSMAEJFVWIL-UHFFFAOYSA-O 0.000 claims 10
- VCCRNZQBSJXYJD-UHFFFAOYSA-N galangin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=CC=C1 VCCRNZQBSJXYJD-UHFFFAOYSA-N 0.000 claims 10
- XOXYHGOIRWABTC-UHFFFAOYSA-N gentisin Chemical compound C1=C(O)C=C2C(=O)C3=C(O)C=C(OC)C=C3OC2=C1 XOXYHGOIRWABTC-UHFFFAOYSA-N 0.000 claims 10
- HLUCICHZHWJHLL-UHFFFAOYSA-N hematein Chemical compound C12=CC=C(O)C(O)=C2OCC2(O)C1=C1C=C(O)C(=O)C=C1C2 HLUCICHZHWJHLL-UHFFFAOYSA-N 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 claims 10
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 claims 10
- BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 claims 10
- WDGFFVCWBZVLCE-UHFFFAOYSA-N purpurogallin Chemical compound C1=CC=C(O)C(=O)C2=C1C=C(O)C(O)=C2O WDGFFVCWBZVLCE-UHFFFAOYSA-N 0.000 claims 10
- JVXZRQGOGOXCEC-UHFFFAOYSA-N scutellarein Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C(O)=C(O)C=C2O1 JVXZRQGOGOXCEC-UHFFFAOYSA-N 0.000 claims 10
- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 claims 9
- 235000008714 apigenin Nutrition 0.000 claims 9
- XADJWCRESPGUTB-UHFFFAOYSA-N apigenin Natural products C1=CC(O)=CC=C1C1=CC(=O)C2=CC(O)=C(O)C=C2O1 XADJWCRESPGUTB-UHFFFAOYSA-N 0.000 claims 9
- 229940117893 apigenin Drugs 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- 102000003802 alpha-Synuclein Human genes 0.000 claims 8
- 108090000185 alpha-Synuclein Proteins 0.000 claims 8
- 230000015572 biosynthetic process Effects 0.000 claims 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 7
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 7
- 208000024827 Alzheimer disease Diseases 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims 6
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims 6
- KICYRZIVKKYRFS-UHFFFAOYSA-N 2-(3,5-dihydroxyphenyl)benzene-1,3,5-triol Chemical compound OC1=CC(O)=CC(C=2C(=CC(O)=CC=2O)O)=C1 KICYRZIVKKYRFS-UHFFFAOYSA-N 0.000 claims 6
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 claims 6
- 239000001263 FEMA 3042 Substances 0.000 claims 6
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims 6
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 claims 6
- 235000015523 tannic acid Nutrition 0.000 claims 6
- 229920002258 tannic acid Polymers 0.000 claims 6
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims 6
- 229940033123 tannic acid Drugs 0.000 claims 6
- SBZWTSHAFILOTE-SOUVJXGZSA-N (2R,3S,4S)-leucocyanidin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3[C@H](O)[C@@H]2O)=CC=C(O)C(O)=C1 SBZWTSHAFILOTE-SOUVJXGZSA-N 0.000 claims 5
- QXWYKJLNLSIPIN-YUMQZZPRSA-N (2s,3s)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate Chemical compound [O-]C(=O)[C@@H]([NH3+])[C@@H](O)C1=CC=C(O)C(O)=C1 QXWYKJLNLSIPIN-YUMQZZPRSA-N 0.000 claims 5
- FAMUIRDLAWWMCQ-AQFAATAFSA-N (4s,4as,5as,6s,12ar)-n-[[4-[n-(diaminomethylidene)carbamimidoyl]piperazin-1-yl]methyl]-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound OC([C@@]1(O)C(=O)C=2[C@@H]([C@](C3=CC=CC(O)=C3C=2O)(C)O)C[C@H]1[C@@H](C1=O)N(C)C)=C1C(=O)NCN1CCN(C(=N)N=C(N)N)CC1 FAMUIRDLAWWMCQ-AQFAATAFSA-N 0.000 claims 5
- NWPIUETWDSWOKV-ZUOHIMJMSA-N (7s,9r,10r)-7,10-bis[[(2s,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy]-9-ethyl-4,6,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O([C@H]1C[C@]([C@@H](C2=C(O)C=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)O[C@@H]1O[C@@H](C)[C@@H](O)[C@H](C1)N(C)C)(O)CC)[C@H]1C[C@H](N(C)C)[C@H](O)[C@H](C)O1 NWPIUETWDSWOKV-ZUOHIMJMSA-N 0.000 claims 5
- NJLAGDPRCAPJIF-MHSJTTIKSA-N (8S)-1',3',9-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-1,4',5',8',9'-pentone Chemical compound COc1cc(=O)c2c(c1=O)c(=O)c1=C(O)[C@]3(CCc4cc5cc(\C=C\C=C\C)[nH]c(=O)c5c(O)c34)C(O)=c1c2=O NJLAGDPRCAPJIF-MHSJTTIKSA-N 0.000 claims 5
- XZSUEVFAMOKROK-UHFFFAOYSA-N 1,2-dihydroxy-3-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(O)C([N+]([O-])=O)=C2 XZSUEVFAMOKROK-UHFFFAOYSA-N 0.000 claims 5
- TWJSDJTWVVOXRT-UHFFFAOYSA-N 1-ethyl-5-oxopyrrolidine-3-carboxamide Chemical compound CCN1CC(C(N)=O)CC1=O TWJSDJTWVVOXRT-UHFFFAOYSA-N 0.000 claims 5
- HEFYRPDDQCAYRU-UHFFFAOYSA-N 2-[(6-carboxy-2,3,4-trihydroxyphenyl)methyl]-3,4,5-trihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1CC1=C(O)C(O)=C(O)C=C1C(O)=O HEFYRPDDQCAYRU-UHFFFAOYSA-N 0.000 claims 5
- NYCXYKOXLNBYID-UHFFFAOYSA-N 5,7-Dihydroxychromone Natural products O1C=CC(=O)C=2C1=CC(O)=CC=2O NYCXYKOXLNBYID-UHFFFAOYSA-N 0.000 claims 5
- GGMCFLXPZMBJMV-NPVWYNPDSA-N 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical compound C1=C(O)C(OC)=CC=C1C1=C(OC)C(=O)C2=C(O)C(OC)=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=C2O1 GGMCFLXPZMBJMV-NPVWYNPDSA-N 0.000 claims 5
- DNRFNICCPHGYAX-UHFFFAOYSA-N 6-ethyl-2,3,5,7,8-pentahydroxynaphthalene-1,4-dione Chemical compound O=C1C(O)=C(O)C(=O)C2=C(O)C(CC)=C(O)C(O)=C21 DNRFNICCPHGYAX-UHFFFAOYSA-N 0.000 claims 5
- ATEFPOUAMCWAQS-UHFFFAOYSA-N 7,8-dihydroxycoumarin Chemical compound C1=CC(=O)OC2=C(O)C(O)=CC=C21 ATEFPOUAMCWAQS-UHFFFAOYSA-N 0.000 claims 5
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 5
- VTIKDEXOEJDMJP-UHFFFAOYSA-N Actinorhodine Natural products CC1OC(CC(=O)O)CC2=C1C(=O)c3c(O)c(cc(O)c3C2=O)c4cc(O)c5C(=O)C6=C(C(C)OC(CC(=O)O)C6)C(=O)c5c4O VTIKDEXOEJDMJP-UHFFFAOYSA-N 0.000 claims 5
- FXNFHKRTJBSTCS-UHFFFAOYSA-N Baicalein Natural products C=1C(=O)C=2C(O)=C(O)C(O)=CC=2OC=1C1=CC=CC=C1 FXNFHKRTJBSTCS-UHFFFAOYSA-N 0.000 claims 5
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 5
- VWDXGKUTGQJJHJ-UHFFFAOYSA-N Catenarin Natural products C1=C(O)C=C2C(=O)C3=C(O)C(C)=CC(O)=C3C(=O)C2=C1O VWDXGKUTGQJJHJ-UHFFFAOYSA-N 0.000 claims 5
- GGMCFLXPZMBJMV-UHFFFAOYSA-N Centaurein Natural products C1=C(O)C(OC)=CC=C1C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC3C(C(O)C(O)C(CO)O3)O)C=C2O1 GGMCFLXPZMBJMV-UHFFFAOYSA-N 0.000 claims 5
- RDFLLVCQYHQOBU-GPGGJFNDSA-O Cyanin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@H](CO)O1)c1c(-c2cc(O)c(O)cc2)[o+]c2c(c(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O3)cc(O)c2)c1 RDFLLVCQYHQOBU-GPGGJFNDSA-O 0.000 claims 5
- AVGPOAXYRRIZMM-UHFFFAOYSA-N D-Apiose Natural products OCC(O)(CO)C(O)C=O AVGPOAXYRRIZMM-UHFFFAOYSA-N 0.000 claims 5
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims 5
- ASNHGEVAWNWCRQ-LJJLCWGRSA-N D-apiofuranose Chemical compound OC[C@@]1(O)COC(O)[C@@H]1O ASNHGEVAWNWCRQ-LJJLCWGRSA-N 0.000 claims 5
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N D-apiofuranose Natural products OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 claims 5
- GCPYCNBGGPHOBD-UHFFFAOYSA-N Delphinidin Natural products OC1=Cc2c(O)cc(O)cc2OC1=C3C=C(O)C(=O)C(=C3)O GCPYCNBGGPHOBD-UHFFFAOYSA-N 0.000 claims 5
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 claims 5
- 239000010282 Emodin Substances 0.000 claims 5
- RBLJKYCRSCQLRP-UHFFFAOYSA-N Emodin-dianthron Natural products O=C1C2=CC(C)=CC(O)=C2C(=O)C2=C1CC(=O)C=C2O RBLJKYCRSCQLRP-UHFFFAOYSA-N 0.000 claims 5
- RAVDMGKYJQVXDU-UHFFFAOYSA-N Ergoflavine Natural products OC1C(C)CC(C2(O)C(=O)C3=C4O)OC(=O)C12OC3=CC=C4C(C(O)=C1C(=O)C23O)=CC=C1OC31C(=O)OC2CC(C)C1O RAVDMGKYJQVXDU-UHFFFAOYSA-N 0.000 claims 5
- CRSFLLTWRCYNNX-UHFFFAOYSA-N Fraxin Natural products OC=1C(OC)=CC=2C=CC(=O)OC=2C=1OC1OC(CO)C(O)C(O)C1O CRSFLLTWRCYNNX-UHFFFAOYSA-N 0.000 claims 5
- FNUPUYFWZXZMIE-UHFFFAOYSA-N Fustin Natural products O1C2=CC(O)=CC=C2C(=O)C(O)C1C1=CC=C(O)C(O)=C1 FNUPUYFWZXZMIE-UHFFFAOYSA-N 0.000 claims 5
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2000
- 2000-12-26 US US09/748,748 patent/US20010047032A1/en not_active Abandoned
- 2000-12-28 AU AU26121/01A patent/AU2612101A/en not_active Abandoned
- 2000-12-28 CA CA2392709A patent/CA2392709C/en not_active Expired - Lifetime
- 2000-12-28 EP EP00989636A patent/EP1244435B9/en not_active Expired - Lifetime
- 2000-12-28 JP JP2001549649A patent/JP4370072B2/ja not_active Expired - Fee Related
- 2000-12-28 ES ES00989636T patent/ES2295078T3/es not_active Expired - Lifetime
- 2000-12-28 WO PCT/US2000/035715 patent/WO2001049281A2/en not_active Ceased
- 2000-12-28 DK DK00989636T patent/DK1244435T5/da active
- 2000-12-28 CA CA2686468A patent/CA2686468C/en not_active Expired - Lifetime
- 2000-12-28 DE DE60037139A patent/DE60037139D1/de not_active Expired - Lifetime
- 2000-12-28 DE DE60037139T patent/DE60037139T4/de not_active Expired - Lifetime
- 2000-12-28 AT AT00989636T patent/ATE378043T1/de active
-
2004
- 2004-01-21 US US10/762,444 patent/US20040152760A1/en not_active Abandoned
-
2007
- 2007-02-23 US US11/710,228 patent/US20070191330A1/en not_active Abandoned
-
2008
- 2008-08-12 JP JP2008207956A patent/JP5366473B2/ja not_active Expired - Fee Related
-
2010
- 2010-09-21 US US12/886,735 patent/US20110065657A1/en not_active Abandoned
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