EP1027335A1 - Ortho-hydroxypyridinone als eisenchelatbildner und antioxidantmittel - Google Patents
Ortho-hydroxypyridinone als eisenchelatbildner und antioxidantmittelInfo
- Publication number
- EP1027335A1 EP1027335A1 EP98950227A EP98950227A EP1027335A1 EP 1027335 A1 EP1027335 A1 EP 1027335A1 EP 98950227 A EP98950227 A EP 98950227A EP 98950227 A EP98950227 A EP 98950227A EP 1027335 A1 EP1027335 A1 EP 1027335A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound according
- alkyl
- methyl
- hydroxy
- butyl
- 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.)
- Withdrawn
Links
- 239000003963 antioxidant agent Substances 0.000 title claims description 28
- 239000000797 iron chelating agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 180
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 67
- 230000036542 oxidative stress Effects 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 42
- 230000003078 antioxidant effect Effects 0.000 claims description 26
- 235000006708 antioxidants Nutrition 0.000 claims description 26
- 208000006011 Stroke Diseases 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 230000004792 oxidative damage Effects 0.000 claims description 16
- 210000003169 central nervous system Anatomy 0.000 claims description 10
- -1 hydroxy-substituted phenyl ring Chemical group 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
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- 102000004190 Enzymes Human genes 0.000 claims description 4
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- 102000019197 Superoxide Dismutase Human genes 0.000 claims description 4
- 108010012715 Superoxide dismutase Proteins 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 208000020431 spinal cord injury Diseases 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000003244 pro-oxidative effect Effects 0.000 claims 2
- MXBCYQUALCBQIJ-RYVPXURESA-N (8s,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1CC[C@@H]2[C@H]3C(=C)C[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 MXBCYQUALCBQIJ-RYVPXURESA-N 0.000 claims 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims 1
- 241000223109 Trypanosoma cruzi Species 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
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- 230000000654 trypanocidal effect Effects 0.000 claims 1
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 229910052681 coesite Inorganic materials 0.000 description 12
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- 239000000377 silicon dioxide Substances 0.000 description 12
- 229910052682 stishovite Inorganic materials 0.000 description 12
- 229910052905 tridymite Inorganic materials 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
- 210000004556 brain Anatomy 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 230000003859 lipid peroxidation Effects 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000003855 balanced salt solution Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
- 230000000324 neuroprotective effect Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- LQDVCPYRCOKNMV-UHFFFAOYSA-N 2-methyl-3-phenylmethoxypyran-4-one Chemical compound O1C=CC(=O)C(OCC=2C=CC=CC=2)=C1C LQDVCPYRCOKNMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- TZXKOCQBRNJULO-UHFFFAOYSA-N Ferriprox Chemical compound CC1=C(O)C(=O)C=CN1C TZXKOCQBRNJULO-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
- LKIMDXQLHFCXQF-UHFFFAOYSA-N 3-methoxy-1h-pyridin-2-one Chemical compound COC1=CC=CN=C1O LKIMDXQLHFCXQF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 3
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
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- YMXJIXXBIBPHGM-UHFFFAOYSA-N 2-methyl-3-phenylmethoxy-1-[2-(2,3,5-trimethyl-4-phenylmethoxyphenoxy)ethyl]pyridin-4-one Chemical compound CC=1C(C)=C(OCC=2C=CC=CC=2)C(C)=CC=1OCCN(C=1C)C=CC(=O)C=1OCC1=CC=CC=C1 YMXJIXXBIBPHGM-UHFFFAOYSA-N 0.000 description 2
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- FJDLQLIRZFKEKJ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanamide Chemical compound CC(C)(C)C1=CC(CCC(N)=O)=CC(C(C)(C)C)=C1O FJDLQLIRZFKEKJ-UHFFFAOYSA-N 0.000 description 2
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- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 201000002498 viral encephalitis Diseases 0.000 description 1
- 201000010044 viral meningitis Diseases 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9723078 | 1997-10-31 | ||
| GBGB9723078.3A GB9723078D0 (en) | 1997-10-31 | 1997-10-31 | Chemical compounds |
| PCT/GB1998/003244 WO1999023075A1 (en) | 1997-10-31 | 1998-10-30 | Ortho-hydroxypyridinone derivatives as iron chelating and antioxidant agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1027335A1 true EP1027335A1 (de) | 2000-08-16 |
Family
ID=10821419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP98950227A Withdrawn EP1027335A1 (de) | 1997-10-31 | 1998-10-30 | Ortho-hydroxypyridinone als eisenchelatbildner und antioxidantmittel |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1027335A1 (de) |
| JP (1) | JP2001521924A (de) |
| AU (1) | AU9638098A (de) |
| GB (1) | GB9723078D0 (de) |
| WO (1) | WO1999023075A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111170936A (zh) * | 2020-01-19 | 2020-05-19 | 杭州泽德医药科技有限公司 | 3,4-二羟基-n-(1’-苄基-2’-羟乙基)-2-甲基吡啶氯化物及制备和应用 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1006108A1 (de) * | 1998-12-01 | 2000-06-07 | Cerebrus Pharmaceuticals Limited | 3-Hydroxy-2(1H)-pyridinon- oder 3-hydroxy-4(1H)-pyridinon- Derivate verwendbar als reaktive Sauerstoffspezies-Fänger (ROS) |
| EP1006112A1 (de) * | 1998-12-01 | 2000-06-07 | Cerebrus Pharmaceuticals Limited | 3-Hydroxy-2(1H)-pyridinon- oder 3-hydroxy-4(1H)-pyridinon- Derivate verwendbar als reaktive Sauerstoffspezies-Fänger (ROS) |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| CA2469435A1 (en) | 2001-12-21 | 2003-07-24 | X-Ceptor Therapeutics, Inc. | Modulators of lxr |
| ATE373644T1 (de) | 2002-02-05 | 2007-10-15 | Bristol Myers Squibb Co | N-substituierte 3-hydroxy-4-pyridinone und diese enthaltende pharmazeutika |
| EP1565185A4 (de) | 2002-11-07 | 2011-01-05 | Technion Res & Dev Foundation | Neuroprotektive eisenchelatoren und pharmazeutische zusammensetzungen damit |
| CA2789474A1 (en) | 2010-03-04 | 2011-09-09 | Merck Sharp & Dohme Corp. | Inhibitors of catechol o-methyl transferase and their use in the treatment of psychotic disorders |
| CN110407741B (zh) * | 2018-04-26 | 2023-03-21 | 启元生物(杭州)有限公司 | 一种抗炎化合物及其制备和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8308055D0 (en) * | 1983-03-24 | 1983-05-05 | Hider R C | Pharmaceutical compositions |
| US5336482A (en) * | 1991-12-05 | 1994-08-09 | The Du Pont Merck Pharmaceutical Company | Technetium-99m complexes with N-substituted 3-hydroxy-4-pyridinones |
| US5624901A (en) * | 1994-04-15 | 1997-04-29 | The Regents Of The University Of California | 3-hydroxy-2(1H)-pyridinone chelating agents |
| DE59611243D1 (de) * | 1995-09-29 | 2005-08-11 | Novartis Ag | Hydroxypyridinone |
| GB9625638D0 (en) * | 1996-12-10 | 1997-01-29 | Cenes Ltd | Therapeutic antioxidants for alzheimer's diease |
-
1997
- 1997-10-31 GB GBGB9723078.3A patent/GB9723078D0/en not_active Ceased
-
1998
- 1998-10-30 EP EP98950227A patent/EP1027335A1/de not_active Withdrawn
- 1998-10-30 AU AU96380/98A patent/AU9638098A/en not_active Abandoned
- 1998-10-30 JP JP2000518950A patent/JP2001521924A/ja not_active Withdrawn
- 1998-10-30 WO PCT/GB1998/003244 patent/WO1999023075A1/en not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9923075A1 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111170936A (zh) * | 2020-01-19 | 2020-05-19 | 杭州泽德医药科技有限公司 | 3,4-二羟基-n-(1’-苄基-2’-羟乙基)-2-甲基吡啶氯化物及制备和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9723078D0 (en) | 1998-01-07 |
| JP2001521924A (ja) | 2001-11-13 |
| AU9638098A (en) | 1999-05-24 |
| WO1999023075A1 (en) | 1999-05-14 |
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