ES2254142T3 - Porfirinas sustituidas y su uso terapeutico. - Google Patents
Porfirinas sustituidas y su uso terapeutico.Info
- Publication number
- ES2254142T3 ES2254142T3 ES00905776T ES00905776T ES2254142T3 ES 2254142 T3 ES2254142 T3 ES 2254142T3 ES 00905776 T ES00905776 T ES 00905776T ES 00905776 T ES00905776 T ES 00905776T ES 2254142 T3 ES2254142 T3 ES 2254142T3
- Authority
- ES
- Spain
- Prior art keywords
- same
- manganese
- mmol
- porphyrin
- disease
- 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
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 238000000034 method Methods 0.000 claims abstract description 54
- 239000007800 oxidant agent Substances 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims description 51
- 239000002184 metal Substances 0.000 claims description 51
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 210000004072 lung Anatomy 0.000 claims description 14
- 239000011572 manganese Substances 0.000 claims description 14
- 230000001988 toxicity Effects 0.000 claims description 14
- 231100000419 toxicity Toxicity 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 208000027866 inflammatory disease Diseases 0.000 claims description 11
- 230000006378 damage Effects 0.000 claims description 9
- 229910052748 manganese Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 230000015556 catabolic process Effects 0.000 claims description 7
- 238000006731 degradation reaction Methods 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 230000010410 reperfusion Effects 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 230000001575 pathological effect Effects 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 230000007654 ischemic lesion Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 208000027418 Wounds and injury Diseases 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims 5
- 239000010941 cobalt Substances 0.000 claims 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 5
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 4
- 206010008190 Cerebrovascular accident Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 208000027775 Bronchopulmonary disease Diseases 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 35
- 230000008569 process Effects 0.000 abstract description 9
- 230000035790 physiological processes and functions Effects 0.000 abstract description 3
- 230000001413 cellular effect Effects 0.000 abstract description 2
- 230000009054 pathological process Effects 0.000 abstract description 2
- 208000037273 Pathologic Processes Diseases 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 141
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 description 118
- 150000004032 porphyrins Chemical class 0.000 description 111
- -1 porphyrin compounds Chemical class 0.000 description 74
- 239000007787 solid Substances 0.000 description 59
- 239000011541 reaction mixture Substances 0.000 description 56
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 40
- 238000000746 purification Methods 0.000 description 36
- 238000004440 column chromatography Methods 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 25
- 238000001556 precipitation Methods 0.000 description 24
- 238000010828 elution Methods 0.000 description 21
- PBTPREHATAFBEN-UHFFFAOYSA-N dipyrromethane Chemical compound C=1C=CNC=1CC1=CC=CN1 PBTPREHATAFBEN-UHFFFAOYSA-N 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 18
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 18
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000002867 manganese chloride Nutrition 0.000 description 18
- 239000011565 manganese chloride Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 102000019197 Superoxide Dismutase Human genes 0.000 description 13
- 108010012715 Superoxide dismutase Proteins 0.000 description 13
- 235000019260 propionic acid Nutrition 0.000 description 13
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000008186 active pharmaceutical agent Substances 0.000 description 12
- 239000011888 foil Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000003859 lipid peroxidation Effects 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 102100033220 Xanthine oxidase Human genes 0.000 description 7
- 108010093894 Xanthine oxidase Proteins 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- 230000003902 lesion Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- CMFNMSMUKZHDEY-UHFFFAOYSA-N peroxynitrous acid Chemical compound OON=O CMFNMSMUKZHDEY-UHFFFAOYSA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- KHRJEZPKYNUHAU-UHFFFAOYSA-N CN1C(=NC=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 Chemical compound CN1C(=NC=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 KHRJEZPKYNUHAU-UHFFFAOYSA-N 0.000 description 6
- 102100027186 Extracellular superoxide dismutase [Cu-Zn] Human genes 0.000 description 6
- 108700001268 Extracellular superoxide dismutase [Cu-Zn] Proteins 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 6
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 6
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- KARHMOBVMXGXPO-UHFFFAOYSA-N 2-(4-fluorophenyl)-10,20-bis(1-methylimidazol-2-yl)-21,23-dihydroporphyrin Chemical compound FC1=CC=C(C=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C(=C1C=CC(N1)=CC=1C=CC(N=1)=C2C=1N(C=CN=1)C)C=1N(C=CN=1)C KARHMOBVMXGXPO-UHFFFAOYSA-N 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 102000016938 Catalase Human genes 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- SWWLZNGXLXLMDY-UHFFFAOYSA-N S1C=NC=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 Chemical compound S1C=NC=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 SWWLZNGXLXLMDY-UHFFFAOYSA-N 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- FMHWYMHGJPPYBA-UHFFFAOYSA-N methyl 4-[10,20-bis(1-methylimidazol-2-yl)-21,23-dihydroporphyrin-2-yl]benzoate Chemical compound C(=O)(OC)C1=CC=C(C=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C(=C1C=CC(N1)=CC=1C=CC(N=1)=C2C=1N(C=CN=1)C)C=1N(C=CN=1)C FMHWYMHGJPPYBA-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 230000036542 oxidative stress Effects 0.000 description 5
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 4
- HHXNRYSICGWSGM-UHFFFAOYSA-N C(=O)(OCC)C1=C2NC(=C1)C=C1C=CC(=N1)C(=C1C=CC(N1)=CC=1C=CC(N=1)=C2C=1N(C=CN=1)C)C=1N(C=CN=1)C Chemical compound C(=O)(OCC)C1=C2NC(=C1)C=C1C=CC(=N1)C(=C1C=CC(N1)=CC=1C=CC(N=1)=C2C=1N(C=CN=1)C)C=1N(C=CN=1)C HHXNRYSICGWSGM-UHFFFAOYSA-N 0.000 description 4
- ARUBEJCOTMXILU-UHFFFAOYSA-N C(C)N1C=NC=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 Chemical compound C(C)N1C=NC=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 ARUBEJCOTMXILU-UHFFFAOYSA-N 0.000 description 4
- CDJOADRCQXWYPP-UHFFFAOYSA-N CN1C(=NC(=C1C)C)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 Chemical compound CN1C(=NC(=C1C)C)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 CDJOADRCQXWYPP-UHFFFAOYSA-N 0.000 description 4
- VSEGTUFWNYFLQQ-UHFFFAOYSA-N CN1C(=NN=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 Chemical compound CN1C(=NN=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 VSEGTUFWNYFLQQ-UHFFFAOYSA-N 0.000 description 4
- GLBJTYREBOXGAX-UHFFFAOYSA-N CN1N=CC(=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 Chemical compound CN1N=CC(=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 GLBJTYREBOXGAX-UHFFFAOYSA-N 0.000 description 4
- YCZZNOHAGMXOKH-UHFFFAOYSA-O C[N+]1=C(N(C=C1)C)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 Chemical compound C[N+]1=C(N(C=C1)C)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 YCZZNOHAGMXOKH-UHFFFAOYSA-O 0.000 description 4
- 108010053835 Catalase Proteins 0.000 description 4
- 206010012289 Dementia Diseases 0.000 description 4
- KQPNIFKNMIRVQP-UHFFFAOYSA-N FC(F)(F)C1=C2NC(=C1)C=C1C=CC(=N1)C(=C1C=CC(N1)=CC=1C=CC(N1)=C2C=2NC=CN2)C=2NC=CN2 Chemical compound FC(F)(F)C1=C2NC(=C1)C=C1C=CC(=N1)C(=C1C=CC(N1)=CC=1C=CC(N1)=C2C=2NC=CN2)C=2NC=CN2 KQPNIFKNMIRVQP-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 4
- 102000003992 Peroxidases Human genes 0.000 description 4
- NWKIDGMBPZLHAX-UHFFFAOYSA-N S1C(=NC=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 Chemical compound S1C(=NC=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 NWKIDGMBPZLHAX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 3
- ZXRLWHGLEJGMNO-UHFFFAOYSA-N 1,3-thiazole-5-carbaldehyde Chemical compound O=CC1=CN=CS1 ZXRLWHGLEJGMNO-UHFFFAOYSA-N 0.000 description 3
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 3
- 241000173529 Aconitum napellus Species 0.000 description 3
- GPQHGQLTIYGCEL-UHFFFAOYSA-O CCN1C=C[N+](CC)=C1C1=CC2=CC([N]3)=CC=C3C=C(C=C3)NC3=CC([N]3)=CC=C3C=C1N2 Chemical compound CCN1C=C[N+](CC)=C1C1=CC2=CC([N]3)=CC=C3C=C(C=C3)NC3=CC([N]3)=CC=C3C=C1N2 GPQHGQLTIYGCEL-UHFFFAOYSA-O 0.000 description 3
- VWMFGKJSCDSXBM-UHFFFAOYSA-N CN1C=NC=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 Chemical compound CN1C=NC=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2 VWMFGKJSCDSXBM-UHFFFAOYSA-N 0.000 description 3
- HPKKKFSHXWPQEW-UHFFFAOYSA-N C[N+]1=CN(C=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2)C Chemical compound C[N+]1=CN(C=C1C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2)C HPKKKFSHXWPQEW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 238000011097 chromatography purification Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 230000015654 memory Effects 0.000 description 3
- 238000006213 oxygenation reaction Methods 0.000 description 3
- 230000008506 pathogenesis Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 238000006236 Dondoni homologation reaction Methods 0.000 description 2
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 108700020962 Peroxidase Proteins 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 229940023019 aconite Drugs 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 229940072107 ascorbate Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 206010006475 bronchopulmonary dysplasia Diseases 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000001086 cytosolic effect Effects 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 231100000318 excitotoxic Toxicity 0.000 description 2
- 230000003492 excitotoxic effect Effects 0.000 description 2
- 210000003722 extracellular fluid Anatomy 0.000 description 2
- 210000002744 extracellular matrix Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000007787 long-term memory Effects 0.000 description 2
- 210000004962 mammalian cell Anatomy 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 2
- 108040007629 peroxidase activity proteins Proteins 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 208000019553 vascular disease Diseases 0.000 description 2
- 229940075420 xanthine Drugs 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 description 1
- RTPPLWUJHUAFLS-UHFFFAOYSA-N 1,4,5-trimethylimidazole-2-carbaldehyde Chemical compound CC=1N=C(C=O)N(C)C=1C RTPPLWUJHUAFLS-UHFFFAOYSA-N 0.000 description 1
- JINZWCUGPDJTNB-UHFFFAOYSA-N 1-ethylimidazole-2-carbaldehyde Chemical compound CCN1C=CN=C1C=O JINZWCUGPDJTNB-UHFFFAOYSA-N 0.000 description 1
- UEBFLTZXUXZPJO-UHFFFAOYSA-N 1-methylimidazole-2-carbaldehyde Chemical compound CN1C=CN=C1C=O UEBFLTZXUXZPJO-UHFFFAOYSA-N 0.000 description 1
- MYFZXSOYJVWTBL-UHFFFAOYSA-N 1-methylpyrazole-4-carbaldehyde Chemical compound CN1C=C(C=O)C=N1 MYFZXSOYJVWTBL-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- BNYKZFOZWZMEJD-UHFFFAOYSA-N 3-methylimidazole-4-carbaldehyde Chemical compound CN1C=NC=C1C=O BNYKZFOZWZMEJD-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- ANXPFHNBZJORKW-UHFFFAOYSA-N 4-methyl-3h-1,2,4-triazole-2-carbaldehyde Chemical compound CN1CN(C=O)N=C1 ANXPFHNBZJORKW-UHFFFAOYSA-N 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- FODIZZXWLNCFBV-UHFFFAOYSA-N C=1C=CNC=1.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound C=1C=CNC=1.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 FODIZZXWLNCFBV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 208000031229 Cardiomyopathies Diseases 0.000 description 1
- 108030002440 Catalase peroxidases Proteins 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 229910002535 CuZn Inorganic materials 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010058314 Dysplasia Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- 102000006587 Glutathione peroxidase Human genes 0.000 description 1
- 108700016172 Glutathione peroxidases Proteins 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 206010058490 Hyperoxia Diseases 0.000 description 1
- 208000020358 Learning disease Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 208000029578 Muscle disease Diseases 0.000 description 1
- 208000029549 Muscle injury Diseases 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 201000009623 Myopathy Diseases 0.000 description 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 241000282520 Papio Species 0.000 description 1
- 241001504519 Papio ursinus Species 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 206010036600 Premature labour Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 1
- 208000006193 Pulmonary infarction Diseases 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 206010049771 Shock haemorrhagic Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 230000009603 aerobic growth Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 0.000 description 1
- 230000011382 collagen catabolic process Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 210000003618 cortical neuron Anatomy 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
- 239000006071 cream Substances 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 208000012059 diaphragm disease Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005206 flow analysis Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000006481 glucose medium Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 230000000222 hyperoxic effect Effects 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- VYLLNBWSIBGKPW-UHFFFAOYSA-O iron(3+);5,10,15,20-tetrakis(1-methylpyridin-1-ium-4-yl)-21,22-dihydroporphyrin Chemical compound [Fe+3].C1=C[N+](C)=CC=C1C(C=1C=CC(N=1)=C(C=1C=C[N+](C)=CC=1)C1=CC=C(N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(N1)=C1C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 VYLLNBWSIBGKPW-UHFFFAOYSA-O 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 201000003723 learning disability Diseases 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 229940126707 lipid peroxidation inhibitor Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000011360 lung alveolus development Effects 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 229940118019 malondialdehyde Drugs 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AKZFRMNXBLFDNN-UHFFFAOYSA-K meso-tetrakis(n-methyl-4-pyridyl)porphine tetrakis(p-toluenesulfonate) Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1.C1=C[N+](C)=CC=C1C(C=1C=CC(N=1)=C(C=1C=C[N+](C)=CC=1)C1=CC=C(N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(N1)=C1C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 AKZFRMNXBLFDNN-UHFFFAOYSA-K 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 210000003061 neural cell Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 201000008312 primary pulmonary hypertension Diseases 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000002731 protein assay Methods 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 230000007575 pulmonary infarction Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- MYFATKRONKHHQL-UHFFFAOYSA-N rhodamine 123 Chemical compound [Cl-].COC(=O)C1=CC=CC=C1C1=C2C=CC(=[NH2+])C=C2OC2=CC(N)=CC=C21 MYFATKRONKHHQL-UHFFFAOYSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 208000037905 systemic hypertension Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000006442 vascular tone Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/409—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Toxicology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11701099P | 1999-01-25 | 1999-01-25 | |
| US117010P | 1999-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2254142T3 true ES2254142T3 (es) | 2006-06-16 |
Family
ID=22370524
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00905776T Expired - Lifetime ES2254142T3 (es) | 1999-01-25 | 2000-01-25 | Porfirinas sustituidas y su uso terapeutico. |
| ES05014279T Expired - Lifetime ES2385486T3 (es) | 1999-01-25 | 2000-01-25 | Porfirinas sustituidas y su uso terapéutico |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05014279T Expired - Lifetime ES2385486T3 (es) | 1999-01-25 | 2000-01-25 | Porfirinas sustituidas y su uso terapéutico |
Country Status (17)
| Country | Link |
|---|---|
| US (7) | US6544975B1 (enExample) |
| EP (3) | EP1616869B1 (enExample) |
| JP (1) | JP4501128B2 (enExample) |
| KR (1) | KR100753184B1 (enExample) |
| CN (1) | CN1156478C (enExample) |
| AT (2) | ATE552260T1 (enExample) |
| AU (1) | AU779283B2 (enExample) |
| BR (1) | BR0007720B1 (enExample) |
| CA (1) | CA2359116C (enExample) |
| DE (1) | DE60024588T2 (enExample) |
| DK (2) | DK1155019T3 (enExample) |
| ES (2) | ES2254142T3 (enExample) |
| IL (3) | IL144503A0 (enExample) |
| MX (1) | MXPA01007451A (enExample) |
| NZ (1) | NZ513164A (enExample) |
| WO (1) | WO2000043395A1 (enExample) |
| ZA (1) | ZA200106107B (enExample) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6127356A (en) | 1993-10-15 | 2000-10-03 | Duke University | Oxidant scavengers |
| US5747026A (en) * | 1993-10-15 | 1998-05-05 | University Of Alabama At Birmingham Research Foundation | Antioxidants |
| EP1045851B1 (en) | 1997-11-03 | 2003-04-23 | Duke University | Substituted porphyrins |
| CA2329751C (en) | 1998-04-24 | 2010-10-12 | Duke University | Substituted porphyrins |
| EP1616869B1 (en) | 1999-01-25 | 2012-04-04 | National Jewish Health | Substituted porphyrins and their therapeutic use |
| FR2806911B1 (fr) * | 2000-03-28 | 2003-01-10 | Univ Rene Descartes | Utilisation de mimetiques de la sod dans le traitement d'insuffisances hepatocellulaires |
| US20030069281A1 (en) * | 2000-06-14 | 2003-04-10 | Irwin Fridovich | Tetrapyrroles |
| CA2436245C (en) | 2001-01-19 | 2013-04-23 | National Jewish Medical And Research Center | Medicament for protection in radiotherapy |
| PT1389617E (pt) * | 2001-04-27 | 2007-04-30 | Zenyaku Kogyo Kk | Composto heterocíclico e agente antitumoral contendo o mesmo como igrediente activo |
| WO2002098431A1 (en) * | 2001-06-01 | 2002-12-12 | National Jewish Medical And Research Center | Oxidant scavengers for treatment of diabetes or use in transplantation or induction of immune tolerance |
| US20030086916A1 (en) * | 2001-10-12 | 2003-05-08 | Goligorsky Michael S. | Use of peroxynitrite scavengers or peroxynitrite formation inhibitors that do not diminish nitric oxide synthesis or activity to reverse or prevent premature vascular senescence |
| EP1513537A4 (en) * | 2002-06-07 | 2006-09-06 | Univ Duke | Substituted porphyrins |
| US20040127479A1 (en) * | 2002-08-27 | 2004-07-01 | Merck Patent Gmbh | Peroxynitrite rearrangement catalysts |
| EP1581212A4 (en) * | 2002-12-06 | 2008-11-05 | Alcon Inc | SUPEROXIDE DISMUTASE IMITATIONS FOR THE TREATMENT OF EYE DISORDERS AND DISEASES |
| 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 |
| EP1452175A1 (en) * | 2003-02-28 | 2004-09-01 | Medesis Pharma S.A. | Manganese based organometallic complexes, pharmaceutical compositions and dietetic products |
| US20080161255A1 (en) * | 2003-05-29 | 2008-07-03 | Michael Brownlee | Use of Parp Inhibitors for Prevention and Treatment of Diabetic and Insulin Resistance Complications |
| US7299082B2 (en) | 2003-10-31 | 2007-11-20 | Abbott Diabetes Care, Inc. | Method of calibrating an analyte-measurement device, and associated methods, devices and systems |
| US7699964B2 (en) | 2004-02-09 | 2010-04-20 | Abbott Diabetes Care Inc. | Membrane suitable for use in an analyte sensor, analyte sensor, and associated method |
| WO2005077269A1 (en) | 2004-02-09 | 2005-08-25 | Duke University | Substituted porphyrins |
| US8165651B2 (en) | 2004-02-09 | 2012-04-24 | Abbott Diabetes Care Inc. | Analyte sensor, and associated system and method employing a catalytic agent |
| EA010834B1 (ru) * | 2004-03-29 | 2008-12-30 | Инотек Фармасьютикалз Корпорейшн | Пиридилзамещённые порфириновые соединения и способы их применения |
| 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 |
| WO2006037050A2 (en) * | 2004-09-24 | 2006-04-06 | Metaphore Pharmaceuticals, Inc. | Methods for treating congestive heart failure |
| GB0424294D0 (en) * | 2004-11-03 | 2004-12-01 | Elam T Ltd | Buffer layer |
| US7582751B2 (en) * | 2005-07-29 | 2009-09-01 | North Carolina State University | Methods and intermediates for the synthesis of porphyrins |
| US7501508B2 (en) * | 2005-07-29 | 2009-03-10 | North Caroline State University | Methods and intermediates for the synthesis of porphyrins |
| US7885698B2 (en) * | 2006-02-28 | 2011-02-08 | Abbott Diabetes Care Inc. | Method and system for providing continuous calibration of implantable analyte sensors |
| WO2008070579A2 (en) * | 2006-12-01 | 2008-06-12 | Loma Linda University Medical Center | Inhibition of brain enzymes involved in cerebral amyloid angiopathy and macular degeneration |
| US20080289053A1 (en) * | 2007-05-15 | 2008-11-20 | The Regents Of The University Of California | Methods and systems for identifying modulators of longevity |
| WO2009004339A2 (en) * | 2007-07-03 | 2009-01-08 | Imperial Innovations Limited | Compositions and methods relating to manipulation of the myeloid immune compartment during respiratory infection |
| US8791099B2 (en) * | 2007-08-28 | 2014-07-29 | Technion Research And Development Foundation Ltd. | Transition metal complexes of corroles for preventing cardiovascular diseases or disorders |
| US8598150B1 (en) | 2008-04-02 | 2013-12-03 | Jonathan R. Brestoff | Composition and method for affecting obesity and related conditions |
| US8987245B2 (en) | 2008-04-02 | 2015-03-24 | Jonathan R. Brestoff Parker | Composition and method for affecting obesity and related conditions |
| ES2464728T3 (es) | 2008-05-23 | 2014-06-03 | National Jewish Health | Compuestos para su uso en el tratamiento de lesiones asociadas con la exposición a una especie química alquilante |
| US20120065181A1 (en) * | 2009-05-26 | 2012-03-15 | Warner David S | Method of providing neuroprotection using substituted porphyrins |
| WO2011028935A2 (en) * | 2009-09-02 | 2011-03-10 | The Regents Of The University Of Colorado | Methods of treating mitochondrial disorders using metalloporhyrins |
| HUE029083T2 (en) * | 2010-10-06 | 2017-02-28 | Aeolus Sciences Inc | Treatment of neurodegenerative diseases with porphyrin |
| WO2012105483A1 (ja) * | 2011-01-31 | 2012-08-09 | 国立大学法人宇都宮大学 | ポルフィリン型骨格を有する化合物の金属錯体の製造方法 |
| WO2013130150A2 (en) | 2011-12-02 | 2013-09-06 | The Regents Of The University Of Colorado, A Body Corporate | Metalloporphyrin neurological treatments |
| CN102775415B (zh) * | 2012-07-10 | 2014-10-22 | 西北大学 | 一种卟啉的合成方法 |
| US20140085895A1 (en) * | 2012-08-16 | 2014-03-27 | Thomas Frawley | LED Bracket Apparatus for High-Output LED Lighting Systems |
| EP3797798B1 (en) | 2013-03-14 | 2022-09-28 | Profusa, Inc. | Oxygen sensors |
| US20160113940A1 (en) | 2013-09-03 | 2016-04-28 | Biomimetix J.V., Llc | Methods of treating biofilms |
| CN105899514A (zh) * | 2013-11-22 | 2016-08-24 | 风神科学公司 | 卟啉化合物的合成和配制 |
| EP3089666B1 (en) | 2013-12-31 | 2020-08-19 | Abbott Diabetes Care Inc. | Self-powered analyte sensor and devices using the same |
| US10064871B2 (en) | 2014-01-22 | 2018-09-04 | Biomimetix Jv, Llc | Methods of treating skin disorders |
| US10080759B2 (en) | 2014-01-22 | 2018-09-25 | Duke University | Methods of treating pruritus |
| AT516549B1 (de) * | 2014-11-20 | 2017-05-15 | Wenatex Forschung - Entw - Produktion Gmbh | Antimikrobielles Mittel zum biociden Ausrüsten von Polymeren |
| EP3365349B1 (en) | 2015-08-18 | 2022-06-15 | University of Pittsburgh- Of the Commonwealth System of Higher Education | Viologen-functionalized porphyrins for reducing biofouling on surfaces |
| KR20190098211A (ko) * | 2016-12-20 | 2019-08-21 | 듀크 유니버시티 | 치환 포르피린 약학적 화합물 및 조성물의 제조 방법 |
| WO2018119204A1 (en) * | 2016-12-21 | 2018-06-28 | Profusa, Inc. | Polymerizable near-ir dyes |
| WO2020006248A1 (en) | 2018-06-27 | 2020-01-02 | Soya Gamsey | Near-ir glucose sensors |
| CN110028514B (zh) * | 2019-05-30 | 2021-07-02 | 湖南科技大学 | 5,10,15,20-四芳基-2,3-咪唑稠合-21-碳叶绿素化合物及制备方法 |
| EP3983486A1 (en) | 2019-06-14 | 2022-04-20 | Universidade de Coimbra | Small cationic ortho-5,15-di-heteroaryl-porphyrins derivatives and their applications in photoinactivation of microorganisms |
| US12201649B2 (en) | 2021-11-12 | 2025-01-21 | Villanova University | Pharmaceutical composition comprising oxidizable biphenol and manganese porphyrin, and method of using the same |
| CN116284017B (zh) * | 2023-03-27 | 2024-03-22 | 中国科学院青岛生物能源与过程研究所 | 一种利用仿酶高效催化氧化制备酰胺化合物的方法 |
Family Cites Families (123)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US437221A (en) * | 1890-09-30 | Circular-saw-smithing machine | ||
| US2951799A (en) | 1957-11-13 | 1960-09-06 | Monsanto Chemicals | Photoxidation processes using heterocyclic photosensitizers |
| JPS5641611B2 (enExample) * | 1973-04-19 | 1981-09-29 | ||
| DE3464252D1 (en) | 1983-06-03 | 1987-07-23 | Hoffmann La Roche | Labelled molecules for fluorescence immunoassays and processes and intermediates for their preparation |
| US4829984A (en) * | 1983-12-15 | 1989-05-16 | Gordon Robert T | Method for the improvement of transplantation techniques and for the preservation of tissue |
| US4963367A (en) | 1984-04-27 | 1990-10-16 | Medaphore, Inc. | Drug delivery compositions and methods |
| US5087438A (en) * | 1984-07-03 | 1992-02-11 | Gordon Robert T | Method for affecting intracellular and extracellular electric and magnetic dipoles |
| US4911920A (en) * | 1986-07-30 | 1990-03-27 | Alcon Laboratories, Inc. | Sustained release, comfort formulation for glaucoma therapy |
| GB8429845D0 (en) | 1984-11-26 | 1985-01-03 | Efamol Ltd | Porphyrins & cancer treatment |
| US4758422A (en) | 1985-01-04 | 1988-07-19 | Salutar Inc. | Ferrioxamine paramagnetic contrast agents for MR imaging |
| US4657902A (en) | 1985-03-25 | 1987-04-14 | The Rockefeller University | Therapeutic use of tin mesoporphyrin |
| JPS63500175A (ja) | 1985-05-22 | 1988-01-21 | リポソ−ム テクノロジ−，インコ−ポレイテツド | リポソ−ム吸入法および吸入システム |
| DK402785D0 (da) | 1985-09-03 | 1985-09-03 | Syn Tek Ab | Fremgangsmaade til fremstilling af et enzym |
| US5248603A (en) | 1985-09-03 | 1993-09-28 | Symbicom Aktiebolag | Superoxide dismutase |
| FR2588189B1 (fr) * | 1985-10-03 | 1988-12-02 | Merck Sharp & Dohme | Composition pharmaceutique de type a transition de phase liquide-gel |
| US4866054A (en) * | 1986-05-13 | 1989-09-12 | Chai-Tech Corporation | Antioxidant metallo-organic treatment of inflammation |
| US4746735A (en) | 1986-11-21 | 1988-05-24 | The Dow Chemical Company | Regiospecific aryl nitration of meso-substituted tetraarylporphyrins |
| US5162231A (en) | 1989-10-25 | 1992-11-10 | Cole Dean A | Method of using 5,10,15,20-tetrakis(carboxyphenyl)porphine for detecting cancers of the lung |
| DE3854872D1 (de) | 1987-03-14 | 1996-02-22 | Boehringer Ingelheim Int | Humane Mangan-Superoxiddismutase (hMn-SOD) |
| DE3800973C2 (de) * | 1987-03-25 | 1992-03-19 | Degussa Ag, 6000 Frankfurt, De | Oxowolfram(v)-porphyrin-komplexe wo(p)x |
| US5223538A (en) | 1987-03-31 | 1993-06-29 | Duke University | Superoxide dismutase mimic |
| US5227405A (en) | 1987-03-31 | 1993-07-13 | Duke University | Superoxide dismutase mimic |
| US4892941A (en) | 1987-04-17 | 1990-01-09 | Dolphin David H | Porphyrins |
| US4851403A (en) | 1987-04-21 | 1989-07-25 | Johnson Matthey, Inc. | Radiation sensitizers |
| US4885114A (en) | 1987-04-22 | 1989-12-05 | Barnes Engineering Co. | Metallized tetra((meso)-5-methyl-2-thiophene)porphines, platinum (5-bromo octaethylporphine) and optical filters containing same |
| US5051337A (en) | 1987-06-10 | 1991-09-24 | Director-General Of Agency Of Industrial Science And Technology | Optical recording material |
| DE3805697A1 (de) * | 1988-02-24 | 1989-09-07 | Bayer Ag | Verfahren zur herstellung von p-hydroxy-benzaldehyden |
| GB8805849D0 (en) | 1988-03-11 | 1988-04-13 | Efamol Holdings | Porphyrins & cancer treatment |
| US5162519A (en) | 1988-03-11 | 1992-11-10 | Efamol Holdings Plc | Porphyrins and cancer treatment |
| DE3809671A1 (de) | 1988-03-18 | 1989-09-28 | Schering Ag | Porphyrin-komplexverbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| US5284647A (en) | 1988-03-18 | 1994-02-08 | Schering Aktiengesellschaft | Mesotetraphenylporphyrin complex compounds, process for their production and pharmaceutical agents containing them |
| US5109016A (en) * | 1988-05-23 | 1992-04-28 | Georgia State University Foundation, Inc. | Method for inhibiting infection or replication of human immunodeficiency virus with porphyrin and phthalocyanine antiviral compositions |
| US5192788A (en) * | 1988-05-23 | 1993-03-09 | Georgia State University Foundation, Inc. | Porphyrin antiviral compositions |
| FR2632187B1 (fr) * | 1988-06-02 | 1990-09-14 | Centre Nat Rech Scient | Derives de metalloporphyrines, leur preparation, leur application en therapeutique et leur utilisation pour la preparation de molecules hybrides |
| US5171680A (en) | 1988-06-14 | 1992-12-15 | Chiron Corporation | Superoxide dismutase analogs having novel binding properties |
| JPH0746212B2 (ja) | 1988-12-03 | 1995-05-17 | 工業技術院長 | 異方性ｌｂ膜の製造法 |
| JPH02213088A (ja) * | 1989-02-13 | 1990-08-24 | Nec Corp | 有機薄膜ｅｌ素子及びその製造方法 |
| WO1990010694A1 (fr) | 1989-03-06 | 1990-09-20 | Suntory Limited | Nouvelle superoxyde dismutase |
| DK455789D0 (da) | 1989-09-15 | 1989-09-15 | Symbicom Ab | Polypeptid |
| US5010073A (en) * | 1989-10-05 | 1991-04-23 | The Rockefeller University | Use of liposomes as carriers for metalloporphyrins |
| EP0424033A3 (en) | 1989-10-19 | 1991-07-31 | Pola Chemical Industries Inc | External skin preparation |
| US5236915A (en) | 1990-05-31 | 1993-08-17 | Health Research, Inc. | Meso poly(4-sulfonatophenyl) porphines as MRI image enhancing agents |
| EP0462836A3 (en) | 1990-06-20 | 1992-08-26 | Mitsui Toatsu Chemicals, Inc. | Recombinant vector plasmid capable of expressing human manganese superoxide dismutase, and process of producing this enzyme |
| US5417111A (en) * | 1990-08-17 | 1995-05-23 | Analog Devices, Inc. | Monolithic chip containing integrated circuitry and suspended microstructure |
| US5217966A (en) | 1990-09-13 | 1993-06-08 | The Regents Of The University Of California | Synthetic drug molecules that mimic metalloenzymes |
| US5202317A (en) | 1990-09-13 | 1993-04-13 | The Regents Of The University Of California | Synthetic drug molecules that mimic metalloenzymes |
| WO1992007935A1 (en) | 1990-11-01 | 1992-05-14 | The Scripps Research Institute | Glycosaminoglycan-targeted fusion proteins, their design, construction and compositions |
| WO1992008482A1 (en) | 1990-11-14 | 1992-05-29 | Uab Research Foundation | Compositions for reducing oxidative injury |
| US5192757A (en) * | 1990-12-20 | 1993-03-09 | Glaxo Inc. | Cobalt porphyrins |
| DE69212850T2 (de) * | 1991-01-15 | 1997-03-06 | Alcon Lab Inc | Verwendung von Karrageenan in topischen ophthalmologischen Zusammensetzungen |
| GB9103991D0 (en) | 1991-02-26 | 1991-04-10 | Nat Res Dev | Molecular electronic devices |
| US5212162A (en) * | 1991-03-27 | 1993-05-18 | Alcon Laboratories, Inc. | Use of combinations gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions |
| FR2676738B1 (fr) | 1991-05-22 | 1995-05-05 | Ir2M | Nouveau derive organique de metal de transition a structure porphyrinique, composition therapeutique le contenant, en particulier a activite hypoglycemiante. |
| CA2072934C (en) * | 1991-07-19 | 2007-08-28 | Karl William Aston | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| DE69224839T2 (de) | 1991-07-19 | 1998-10-08 | Monsanto Co | Mangan-Komplexe mit Stickstoff enthaltenden makrozyklischen Liganden, wirksam als Superoxiddismutasekatalysatoren. |
| US5262532A (en) | 1991-07-22 | 1993-11-16 | E.R. Squibb & Sons, Inc. | Paramagnetic metalloporphyrins as contrast agents for magnetic resonance imaging |
| US5212300A (en) | 1991-09-12 | 1993-05-18 | Sun Company, Inc. (R&M) | Cyano- and polycyanometallo-porphyrins as catalysts for alkane oxidation |
| US5976551A (en) * | 1991-11-15 | 1999-11-02 | Institut Pasteur And Institut Nationale De La Sante Et De La Recherche Medicale | Altered major histocompatibility complex (MHC) determinant and method of using the determinant |
| US5599924A (en) | 1992-08-14 | 1997-02-04 | Trustees Of The University Of Pennsylvania | Electron-deficient porphyrins and processes and intermediates for preparing same |
| US5371199B1 (en) | 1992-08-14 | 1995-12-26 | Univ Pennsylvania | Substituted porphyrins porphyrin-containing polymers and synthetic methods therefor |
| US5493017A (en) | 1992-08-14 | 1996-02-20 | The Trustees Of The University Of Pennsylvania | Ring-metalated porphyrins |
| ES2157221T3 (es) | 1992-09-03 | 2001-08-16 | Univ California | Composiciones metaloporfirinicas. |
| US5403834A (en) * | 1992-12-07 | 1995-04-04 | Eukarion, Inc. | Synthetic catalytic free radical scavengers useful as antioxidants for prevention and therapy of disease |
| US5834509A (en) * | 1992-12-07 | 1998-11-10 | Eukarion, Inc. | Synthetic catalytic free radical scavengers useful as antioxidants for prevention and therapy of disease |
| US5696109A (en) | 1992-12-07 | 1997-12-09 | Eukarion, Inc. | Synthetic catalytic free radical scavengers useful as antioxidants for prevention and therapy of disease |
| US6204259B1 (en) * | 1993-01-14 | 2001-03-20 | Monsanto Company | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| DE4305523A1 (de) | 1993-02-17 | 1994-08-18 | Diagnostikforschung Inst | Meso-Tetraphenylporphyrin-Komplexverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| US5428037A (en) | 1993-04-09 | 1995-06-27 | Syntex Pharmaceuticals, Ltd. | Heterocyclic derivatives in the treatment of Ischaemia and related diseases |
| JP3273082B2 (ja) | 1993-06-18 | 2002-04-08 | 三和電気工業株式会社 | 光コネクタ用スリ−ブホルダ |
| JPH0743337A (ja) * | 1993-07-30 | 1995-02-14 | Toppan Printing Co Ltd | マンガンポルフィリン錯体を感応物質とする陰イオン選択性電極 |
| US6417182B1 (en) * | 1993-08-25 | 2002-07-09 | Anormed Inc. | Pharmaceutical compositions comprising metal complexes |
| US5747026A (en) | 1993-10-15 | 1998-05-05 | University Of Alabama At Birmingham Research Foundation | Antioxidants |
| US6127356A (en) | 1993-10-15 | 2000-10-03 | Duke University | Oxidant scavengers |
| US5994339A (en) | 1993-10-15 | 1999-11-30 | University Of Alabama At Birmingham Research Foundation | Oxidant scavengers |
| US5488145A (en) | 1993-12-23 | 1996-01-30 | Oklahoma Medical Research Foundation | 2,4-disulfonyl phenyl butyl nitrone, its salts, and their use as pharmaceutical free radical traps |
| US5608054A (en) | 1993-12-29 | 1997-03-04 | Sun Company, Inc. (R&M) | Porphyrins and metal complexes thereof having haloalkyl side chains |
| US5405369A (en) * | 1994-01-25 | 1995-04-11 | Medical College Of Ohio | Photochemical ablation of gastro-intestinal tissue for augmentation of an organ |
| US5604199A (en) * | 1994-03-29 | 1997-02-18 | The Nemours Foundation | Method of treating fibrosis in skeletal muscle tissue |
| CZ323496A3 (en) * | 1994-05-13 | 1997-10-15 | Monsanto Co | Pharmaceutical composition containing a catalyst of peroxy nitrite decomposition |
| US6245758B1 (en) * | 1994-05-13 | 2001-06-12 | Michael K. Stern | Methods of use for peroxynitrite decomposition catalysts, pharmaceutical compositions therefor |
| US5563132A (en) * | 1994-06-21 | 1996-10-08 | Bodaness; Richard S. | Two-step cancer treatment method |
| AU3758695A (en) | 1994-09-20 | 1996-04-09 | Duke University | Oxidoreductase activity of manganic porphyrins |
| CA2132690A1 (en) | 1994-09-22 | 1996-03-23 | Dean Willis | Control and modulation of inflammatory response in humans in need of such control and modulation |
| US6013241A (en) * | 1995-01-23 | 2000-01-11 | Schering Aktiengesellschaft | Use of porphyrin-complex or expanded porphyrin-complex compounds as an infarction localization diagnosticum |
| EP0831891B1 (en) * | 1995-06-07 | 2005-10-19 | Duke University | Oxidant scavengers |
| CA2229781A1 (en) | 1995-08-17 | 1997-02-27 | Monsanto Company | Methods of diagnostic image analysis using bioconjugates of metal complexes of nitrogen-containing macrocyclic ligands |
| US5976498A (en) * | 1995-08-17 | 1999-11-02 | Neumann; William L. | Methods of diagnostic image analysis using metal complexes of nitrogen-containing macrocyclic ligands |
| CA2229799A1 (en) | 1995-08-17 | 1997-02-27 | Monsanto Company | Bioconjugates of manganese complexes and their application as catalysts |
| US5648523A (en) * | 1995-10-26 | 1997-07-15 | Chiang Long Y | Fullerene derivatives as free-radical scavengers |
| US5948771A (en) * | 1996-01-31 | 1999-09-07 | The Trustees Of Columbia University In The City Of New York | Method for treating heart failure using tetrapyrroles and metallotetrapyrroles |
| JP2000507929A (ja) | 1996-03-13 | 2000-06-27 | モンサント カンパニー | ジスムタチンスーパーオキシドの触媒として有効な窒素含有大環状化合物配位子を持つ鉄錯体 |
| WO1997033877A1 (en) | 1996-03-13 | 1997-09-18 | Monsanto Company | Bioconjugates of manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| JPH1062350A (ja) * | 1996-08-14 | 1998-03-06 | Ebara Corp | ガス反応性色素を用いたガス検知方法及びガス検知装置 |
| US5756492A (en) * | 1996-09-09 | 1998-05-26 | Sangstat Medical Corporation | Graft survival prolongation with porphyrins |
| AU6650198A (en) | 1997-02-05 | 1998-08-25 | Board Of Regents, The University Of Texas System | Porphyrin compounds as telomerase inhibitors |
| US6214817B1 (en) * | 1997-06-20 | 2001-04-10 | Monsanto Company | Substituted pyridino pentaazamacrocyle complexes having superoxide dismutase activity |
| US6180620B1 (en) | 1997-06-20 | 2001-01-30 | G.D. Searle & Co. | Analgesic methods using synthetic catalysts for the dismutation of superoxide radicals |
| GB9716446D0 (en) | 1997-08-05 | 1997-10-08 | Agrevo Uk Ltd | Fungicides |
| JP3564962B2 (ja) * | 1997-08-26 | 2004-09-15 | 松下電器産業株式会社 | 光記録媒体及びその光記録再生方法 |
| ATE292112T1 (de) | 1997-08-26 | 2005-04-15 | Kumiai Chemical Industry Co | Biarylalkylencarbaminsäurederivate als bakteriozide in landwirtschaft und gartenbau |
| EP1045851B1 (en) * | 1997-11-03 | 2003-04-23 | Duke University | Substituted porphyrins |
| CA2329751C (en) * | 1998-04-24 | 2010-10-12 | Duke University | Substituted porphyrins |
| CA2337756A1 (en) | 1998-07-23 | 2000-02-03 | Otto F. Schall | Libraries of polyhydroxamates and their analogs |
| WO2000023568A2 (en) | 1998-10-06 | 2000-04-27 | Albert Einstein College Of Medicine Of Yeshiva University | Methods and compositions for decreasing mitochondrial overproduction of reactive oxygen species in cells |
| EP1616869B1 (en) * | 1999-01-25 | 2012-04-04 | National Jewish Health | Substituted porphyrins and their therapeutic use |
| DE60037768T2 (de) | 1999-05-27 | 2009-01-15 | Pharmacia Corp.(N.D.Ges.D.Staates Delaware) | Biomaterialien, modifiziert mit Superoxid-Dismutase Imitatoren |
| US6448239B1 (en) | 1999-06-03 | 2002-09-10 | Trustees Of Princeton University | Peroxynitrite decomposition catalysts and methods of use thereof |
| US6608050B2 (en) * | 1999-07-20 | 2003-08-19 | Pharmacia & Upjohn Company | Lyophilizate of lipid complex of water insoluble porphyrins |
| AU1087401A (en) | 1999-10-13 | 2001-04-23 | Uab Research Foundation | Metalloporphyrin treatment of neurologic disease |
| AU771600B2 (en) * | 1999-11-30 | 2004-03-25 | Photochemical Co., Ltd. | Nitroimidazole-supporting porphyrin complex |
| JP3383839B2 (ja) * | 2000-03-13 | 2003-03-10 | 奈良先端科学技術大学院大学長 | 新規なメルカプト置換イミダゾリルポルフィリン金属錯体単量体及びこれを繰り返し単位として有する重合体並びにこれらの製造方法 |
| US6624187B1 (en) * | 2000-06-12 | 2003-09-23 | Health Research, Inc. | Long wave length absorbing bacteriochlorin alkyl ether analogs |
| EP1320532A1 (en) | 2000-06-14 | 2003-06-25 | Duke University | Tetrapyrroles |
| US6403788B1 (en) * | 2000-07-11 | 2002-06-11 | Eukarion, Inc. | Non-genotoxic metalloporphyrins as synthetic catalytic scavengers of reactive oxygen species |
| US6573258B2 (en) * | 2000-09-27 | 2003-06-03 | Frontier Scientific, Inc. | Photodynamic porphyrin antimicrobial agents |
| CA2436245C (en) * | 2001-01-19 | 2013-04-23 | National Jewish Medical And Research Center | Medicament for protection in radiotherapy |
| WO2002078670A1 (en) | 2001-03-02 | 2002-10-10 | Neuron Therapeutics, Inc. | Neuroprotectants formulations and methods |
| AU2002344234B2 (en) | 2001-05-31 | 2007-11-08 | Miravant Pharmaceuticals, Inc. | Metallotetrapyrrolic photosensitizing agents for use in photodynamic therapy |
| US6566517B2 (en) * | 2001-06-06 | 2003-05-20 | Brookhaven Science Associates, Llc | Metalloporphyrins and their uses as imageable tumor-targeting agents for radiation therapy |
| DE10240343A1 (de) | 2002-08-27 | 2004-03-11 | Schering Ag | Peroxynitrit-Umlagerungskatalysatoren |
| WO2005077269A1 (en) | 2004-02-09 | 2005-08-25 | Duke University | Substituted porphyrins |
| JP2008538586A (ja) | 2005-04-21 | 2008-10-30 | グレン エー． ゴールドスタイン， | 酸化ストレスに関連する疾患および病気の処置のためのｎ−アセチルシステインアミド（ｎａｃアミド） |
| WO2011028935A2 (en) | 2009-09-02 | 2011-03-10 | The Regents Of The University Of Colorado | Methods of treating mitochondrial disorders using metalloporhyrins |
-
2000
- 2000-01-25 EP EP05014279A patent/EP1616869B1/en not_active Expired - Lifetime
- 2000-01-25 JP JP2000594811A patent/JP4501128B2/ja not_active Expired - Fee Related
- 2000-01-25 US US09/490,537 patent/US6544975B1/en not_active Expired - Lifetime
- 2000-01-25 BR BRPI0007720-8B1A patent/BR0007720B1/pt not_active IP Right Cessation
- 2000-01-25 NZ NZ513164A patent/NZ513164A/xx not_active IP Right Cessation
- 2000-01-25 EP EP00905776A patent/EP1155019B1/en not_active Expired - Lifetime
- 2000-01-25 DK DK00905776T patent/DK1155019T3/da active
- 2000-01-25 IL IL14450300A patent/IL144503A0/xx active IP Right Grant
- 2000-01-25 AT AT05014279T patent/ATE552260T1/de active
- 2000-01-25 AT AT00905776T patent/ATE312103T1/de not_active IP Right Cessation
- 2000-01-25 CN CNB008054584A patent/CN1156478C/zh not_active Expired - Fee Related
- 2000-01-25 DK DK05014279.3T patent/DK1616869T3/da active
- 2000-01-25 ES ES00905776T patent/ES2254142T3/es not_active Expired - Lifetime
- 2000-01-25 ES ES05014279T patent/ES2385486T3/es not_active Expired - Lifetime
- 2000-01-25 KR KR1020017009367A patent/KR100753184B1/ko not_active Expired - Fee Related
- 2000-01-25 MX MXPA01007451A patent/MXPA01007451A/es active IP Right Grant
- 2000-01-25 AU AU27407/00A patent/AU779283B2/en not_active Ceased
- 2000-01-25 CA CA002359116A patent/CA2359116C/en not_active Expired - Fee Related
- 2000-01-25 EP EP10011098A patent/EP2295435A1/en not_active Withdrawn
- 2000-01-25 DE DE60024588T patent/DE60024588T2/de not_active Expired - Lifetime
- 2000-01-25 WO PCT/US2000/002062 patent/WO2000043395A1/en not_active Ceased
-
2001
- 2001-07-23 IL IL144503A patent/IL144503A/en not_active IP Right Cessation
- 2001-07-25 ZA ZA200106107A patent/ZA200106107B/xx unknown
-
2003
- 2003-01-23 US US10/349,171 patent/US7189707B2/en not_active Expired - Fee Related
-
2006
- 2006-06-16 US US11/424,662 patent/US7820644B2/en not_active Expired - Fee Related
-
2007
- 2007-06-14 IL IL183953A patent/IL183953A/en not_active IP Right Cessation
-
2010
- 2010-09-17 US US12/885,198 patent/US8217026B2/en not_active Expired - Fee Related
-
2012
- 2012-04-26 US US13/457,232 patent/US8546562B2/en not_active Expired - Fee Related
-
2013
- 2013-09-05 US US14/019,295 patent/US8946202B2/en not_active Expired - Fee Related
-
2014
- 2014-12-18 US US14/575,694 patent/US9289434B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2254142T3 (es) | Porfirinas sustituidas y su uso terapeutico. | |
| ES2257858T3 (es) | Porfirinas sustituidas. | |
| ES2198767T3 (es) | Porfirinas sustituidas. | |
| ES2244793T3 (es) | Analogos no centrosimetricos de ftalocianina sustituidos por metales, su preparacion y su utilizacion en terapia fotodinamica y diagnostico in vivo. | |
| JPH06505475A (ja) | 光力学的療法に直接利用するか、または光力学的療法に適切な光活性色素の合成中間体として利用するポルフィセン誘導体 | |
| KR101164138B1 (ko) | 광역학 치료용 수용성 나노구조체 | |
| HK1083626B (en) | Substituted porphyrins and their therapeutic use |