AU2003207750A2 - Furanone derivatives - Google Patents
Furanone derivatives Download PDFInfo
- Publication number
- AU2003207750A2 AU2003207750A2 AU2003207750A AU2003207750A AU2003207750A2 AU 2003207750 A2 AU2003207750 A2 AU 2003207750A2 AU 2003207750 A AU2003207750 A AU 2003207750A AU 2003207750 A AU2003207750 A AU 2003207750A AU 2003207750 A2 AU2003207750 A2 AU 2003207750A2
- Authority
- AU
- Australia
- Prior art keywords
- optionally substituted
- furan
- oxo
- hydroxy
- carboxylic acid
- 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.)
- Abandoned
Links
- 150000002241 furanones Chemical class 0.000 title description 24
- 150000001875 compounds Chemical class 0.000 claims description 203
- -1 carboxy, benzyl Chemical group 0.000 claims description 115
- 229910052739 hydrogen Inorganic materials 0.000 claims description 110
- 239000001257 hydrogen Substances 0.000 claims description 101
- 239000000203 mixture Substances 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 76
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 239000002253 acid Substances 0.000 claims description 55
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 52
- 238000002360 preparation method Methods 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000003107 substituted aryl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 43
- 125000004494 ethyl ester group Chemical group 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 29
- 208000006011 Stroke Diseases 0.000 claims description 25
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 25
- 208000024827 Alzheimer disease Diseases 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 150000001413 amino acids Chemical class 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 206010008118 cerebral infarction Diseases 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 201000006474 Brain Ischemia Diseases 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 230000004770 neurodegeneration Effects 0.000 claims description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 10
- 230000036542 oxidative stress Effects 0.000 claims description 10
- IUCPABAPTDGTHB-UHFFFAOYSA-N CCOC(=O)C1OCC=C1 Chemical compound CCOC(=O)C1OCC=C1 IUCPABAPTDGTHB-UHFFFAOYSA-N 0.000 claims description 9
- 208000010877 cognitive disease Diseases 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 230000003959 neuroinflammation Effects 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 206010039966 Senile dementia Diseases 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
- 238000006668 aldol addition reaction Methods 0.000 claims description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- WRBOXBHZDVBCMU-UHFFFAOYSA-N ethyl 4-hydroxy-5-oxo-3-pyrimidin-2-ylsulfanyl-2-(pyrimidin-2-ylsulfanylmethyl)furan-2-carboxylate Chemical compound O1C(=O)C(O)=C(SC=2N=CC=CN=2)C1(C(=O)OCC)CSC1=NC=CC=N1 WRBOXBHZDVBCMU-UHFFFAOYSA-N 0.000 claims description 7
- 239000002777 nucleoside Substances 0.000 claims description 7
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 206010019196 Head injury Diseases 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- INGLWCGDVIOXKB-UHFFFAOYSA-N ethyl 3-cyclohexylsulfanyl-2-(cyclohexylsulfanylmethyl)-4-hydroxy-5-oxofuran-2-carboxylate Chemical compound O1C(=O)C(O)=C(SC2CCCCC2)C1(C(=O)OCC)CSC1CCCCC1 INGLWCGDVIOXKB-UHFFFAOYSA-N 0.000 claims description 6
- URGFMOAOUINOOA-UHFFFAOYSA-N ethyl 4-hydroxy-5-oxo-3-pyridin-4-ylsulfanyl-2-(pyridin-4-ylsulfanylmethyl)furan-2-carboxylate Chemical compound O1C(=O)C(O)=C(SC=2C=CN=CC=2)C1(C(=O)OCC)CSC1=CC=NC=C1 URGFMOAOUINOOA-UHFFFAOYSA-N 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 208000020431 spinal cord injury Diseases 0.000 claims description 5
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 5
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- VAPFCXNITCQADH-UHFFFAOYSA-N ethyl 3-[(2,4-dichlorophenyl)methylsulfanyl]-2-[(2,4-dichlorophenyl)methylsulfanylmethyl]-4-hydroxy-5-oxofuran-2-carboxylate Chemical compound O1C(=O)C(O)=C(SCC=2C(=CC(Cl)=CC=2)Cl)C1(C(=O)OCC)CSCC1=CC=C(Cl)C=C1Cl VAPFCXNITCQADH-UHFFFAOYSA-N 0.000 claims description 4
- BLXZLGIMWIHPRH-UHFFFAOYSA-N ethyl 4-hydroxy-3-[(6-nitro-1,3-benzothiazol-2-yl)sulfanyl]-2-[(6-nitro-1,3-benzothiazol-2-yl)sulfanylmethyl]-5-oxofuran-2-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2SC(SC3=C(O)C(=O)OC3(CSC=3SC4=CC(=CC=C4N=3)[N+]([O-])=O)C(=O)OCC)=NC2=C1 BLXZLGIMWIHPRH-UHFFFAOYSA-N 0.000 claims description 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- OSJRVNJHZAZFKX-UHFFFAOYSA-N 2-[[2-ethoxycarbonyl-4-hydroxy-5-oxo-3-(2-sulfoethylsulfanyl)furan-2-yl]methylsulfanyl]ethanesulfonic acid Chemical compound OS(=O)(=O)CCSCC1(C(=O)OCC)OC(=O)C(O)=C1SCCS(O)(=O)=O OSJRVNJHZAZFKX-UHFFFAOYSA-N 0.000 claims description 3
- YPSWGUSGXNXBSE-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylsulfanyl)-2-(1h-benzimidazol-2-ylsulfanylmethyl)-4-hydroxy-5-oxofuran-2-carboxylic acid Chemical compound C1=CC=C2NC(SC3=C(O)C(=O)OC3(CSC=3NC4=CC=CC=C4N=3)C(=O)O)=NC2=C1 YPSWGUSGXNXBSE-UHFFFAOYSA-N 0.000 claims description 3
- RXSYKCDNJKPBQO-UHFFFAOYSA-N 4-(1h-benzimidazol-2-ylsulfanyl)-5-(1h-benzimidazol-2-ylsulfanylmethyl)-3-hydroxy-5-(hydroxymethyl)furan-2-one Chemical compound C1=CC=C2NC(SC3=C(O)C(=O)OC3(CSC=3NC4=CC=CC=C4N=3)CO)=NC2=C1 RXSYKCDNJKPBQO-UHFFFAOYSA-N 0.000 claims description 3
- 229910003827 NRaRb Inorganic materials 0.000 claims description 3
- MZNDOTCLCLWGGB-UHFFFAOYSA-N ethyl 4-hydroxy-3-[(4-methoxyphenyl)methylsulfanyl]-2-[(4-methoxyphenyl)methylsulfanylmethyl]-5-oxofuran-2-carboxylate Chemical compound O1C(=O)C(O)=C(SCC=2C=CC(OC)=CC=2)C1(C(=O)OCC)CSCC1=CC=C(OC)C=C1 MZNDOTCLCLWGGB-UHFFFAOYSA-N 0.000 claims description 3
- OPPBNXRIGPRBSJ-UHFFFAOYSA-N ethyl 4-hydroxy-3-methylsulfonyl-2-(methylsulfonylmethyl)-5-oxofuran-2-carboxylate Chemical compound CCOC(=O)C1(CS(C)(=O)=O)OC(=O)C(O)=C1S(C)(=O)=O OPPBNXRIGPRBSJ-UHFFFAOYSA-N 0.000 claims description 3
- UNZXPFPEPXSSKP-UHFFFAOYSA-N ethyl 4-hydroxy-5-oxo-3-[4-(trifluoromethyl)pyrimidin-2-yl]sulfanyl-2-[[4-(trifluoromethyl)pyrimidin-2-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(=O)C(O)=C(SC=2N=C(C=CN=2)C(F)(F)F)C1(C(=O)OCC)CSC1=NC=CC(C(F)(F)F)=N1 UNZXPFPEPXSSKP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 208000032253 retinal ischemia Diseases 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- XIZWKFJENMQBFI-UHFFFAOYSA-N 3,4-dihydro-2h-1,5-benzodithiepine Chemical compound S1CCCSC2=CC=CC=C21 XIZWKFJENMQBFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- IGNUHMNLSOZMNI-UHFFFAOYSA-N ethyl 3-[(5-chloro-1,3-benzothiazol-2-yl)sulfanyl]-2-[(5-chloro-1,3-benzothiazol-2-yl)sulfanylmethyl]-4-hydroxy-5-oxofuran-2-carboxylate Chemical compound ClC1=CC=C2SC(SC3=C(O)C(=O)OC3(CSC=3SC4=CC=C(Cl)C=C4N=3)C(=O)OCC)=NC2=C1 IGNUHMNLSOZMNI-UHFFFAOYSA-N 0.000 claims description 2
- UUNUYUXVMHGTCP-UHFFFAOYSA-N ethyl 4-hydroxy-5-oxo-3-(pyrrolidine-1-carbothioylsulfanyl)-2-(pyrrolidine-1-carbothioylsulfanylmethyl)furan-2-carboxylate Chemical compound O1C(=O)C(O)=C(SC(=S)N2CCCC2)C1(C(=O)OCC)CSC(=S)N1CCCC1 UUNUYUXVMHGTCP-UHFFFAOYSA-N 0.000 claims description 2
- UKHLNCZBYDCVBA-UHFFFAOYSA-N ethyl 4-hydroxy-5-oxo-3-[(5-phenyl-1h-1,2,4-triazol-3-yl)sulfanyl]-2-[(5-phenyl-1h-1,2,4-triazol-3-yl)sulfanylmethyl]furan-2-carboxylate Chemical compound O1C(=O)C(O)=C(SC=2NN=C(N=2)C=2C=CC=CC=2)C1(C(=O)OCC)CSC(NN=1)=NC=1C1=CC=CC=C1 UKHLNCZBYDCVBA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 5
- 230000001363 autoimmune Effects 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- VDYFNCSWVWRWDB-UHFFFAOYSA-N ethyl 4-hydroxy-5-oxo-3-[7-(trifluoromethyl)quinolin-4-yl]sulfanyl-2-[[7-(trifluoromethyl)quinolin-4-yl]sulfanylmethyl]furan-2-carboxylate Chemical compound FC(F)(F)C1=CC=C2C(SC3=C(O)C(=O)OC3(CSC=3C4=CC=C(C=C4N=CC=3)C(F)(F)F)C(=O)OCC)=CC=NC2=C1 VDYFNCSWVWRWDB-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 86
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- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
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- Biomedical Technology (AREA)
- Neurosurgery (AREA)
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- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
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- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35393902P | 2002-01-31 | 2002-01-31 | |
| US60/353,939 | 2002-01-31 | ||
| PCT/US2003/002766 WO2003064403A1 (en) | 2002-01-31 | 2003-01-30 | Furanone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003207750A2 true AU2003207750A2 (en) | 2003-09-02 |
Family
ID=27663268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003207750A Abandoned AU2003207750A2 (en) | 2002-01-31 | 2003-01-30 | Furanone derivatives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6667330B2 (https=) |
| EP (1) | EP1478634A4 (https=) |
| JP (1) | JP2006502963A (https=) |
| AU (1) | AU2003207750A2 (https=) |
| CA (1) | CA2474871A1 (https=) |
| MX (1) | MXPA04007292A (https=) |
| NZ (1) | NZ534305A (https=) |
| WO (1) | WO2003064403A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7985771B2 (en) * | 2002-01-31 | 2011-07-26 | Monsanto Technology Llc | Furanone derivatives |
| US20040156874A1 (en) * | 2003-02-11 | 2004-08-12 | Bradley Pharmaceuticals, Inc. | Urea- a topical anti-inflammatory |
| TW200600091A (en) * | 2004-05-21 | 2006-01-01 | Telik Inc | Sulfonylethyl phosphorodiamidates |
| EP2471530B1 (en) | 2005-06-01 | 2017-01-11 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| US9278085B2 (en) | 2006-02-22 | 2016-03-08 | Edison Pharmaceuticals, Inc. | Side-chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| WO2009061744A2 (en) | 2007-11-06 | 2009-05-14 | Edison Pharmaceuticals, Inc. | 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| EA023618B1 (ru) | 2008-01-08 | 2016-06-30 | Эдисон Фармасьютикалз, Инк. | Производные (гет)арил-п-хинона для лечения митохондриальных болезней |
| WO2009111576A2 (en) | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| WO2009158348A1 (en) | 2008-06-25 | 2009-12-30 | Edison Pharmaceuticals, Inc. | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
| EP2344142B1 (en) | 2008-09-10 | 2024-06-26 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| EP2362726B1 (en) | 2008-10-14 | 2018-08-08 | Bioelectron Technology Corporation | Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells |
| CA2741767C (en) | 2008-10-28 | 2017-09-12 | Ptc Therapeutics, Inc. | Process for the production of alpha-tocotrienol and derivatives |
| PL2424495T3 (pl) | 2009-04-28 | 2018-06-29 | Bioelectron Technology Corporation | Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu |
| JP2014520894A (ja) | 2011-07-19 | 2014-08-25 | エジソン ファーマシューティカルズ, インコーポレイテッド | 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法 |
| ES2660822T3 (es) * | 2012-09-21 | 2018-03-26 | Rhode Island Hospital | Inhibidores de beta-hidrolasa para tratamiento del cáncer |
| US9296712B2 (en) | 2013-03-15 | 2016-03-29 | Edison Pharmaceuticals, Inc. | Resorufin derivatives for treatment of oxidative stress disorders |
| US9670170B2 (en) | 2013-03-15 | 2017-06-06 | Bioelectron Technology Corporation | Resorufin derivatives for treatment of oxidative stress disorders |
| US9868711B2 (en) | 2013-03-15 | 2018-01-16 | Bioelectron Technology Corporation | Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders |
| AU2015364640B2 (en) | 2014-12-16 | 2020-08-13 | Ptc Therapeutics, Inc. | Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
| EP3390377B1 (en) | 2015-12-16 | 2026-03-25 | PTC Therapeutics, Inc. | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| WO2017106803A1 (en) | 2015-12-17 | 2017-06-22 | Bioelectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| JP2018083799A (ja) | 2016-11-15 | 2018-05-31 | バイオエレクトロン テクノロジー コーポレイション | 2−置換アミノ−ナフト[1,2−d]イミダゾール−5−オン化合物またはその製薬学上許容される塩 |
| KR20210076956A (ko) | 2018-10-17 | 2021-06-24 | 피티씨 테라퓨틱스, 인크. | α-시누클레인병증, 타우병증 및 기타 장애를 억제 및 치료하기 위한 2,3,5-트리메틸-6-노닐사이클로헥사-2,5-디엔-1,4-디온 |
| PE20240893A1 (es) | 2021-07-08 | 2024-04-24 | Ptc Therapeutics Inc | Composiciones farmaceuticas que comprenden 2,3,5-trimetil-6-nonilciclohexa-2,5-dien-1,4-diona |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4875564A (https=) | 1972-01-08 | 1973-10-11 | ||
| JPS4988862A (https=) | 1972-12-29 | 1974-08-24 | ||
| JPH06100445A (ja) | 1992-07-06 | 1994-04-12 | Banyu Pharmaceut Co Ltd | 抗腫瘍剤 |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5464865A (en) * | 1993-12-22 | 1995-11-07 | Ortho Pharmaceutical Corporation | 4-aryl- and 4-arylthio-5-hydroxy-2(5H)-furanones as inhibitors of phospholipase A2 |
| JPH07206841A (ja) | 1994-01-20 | 1995-08-08 | Sankyo Co Ltd | ブチロラクトンの製造法 |
| US6020343A (en) | 1995-10-13 | 2000-02-01 | Merck Frosst Canada, Inc. | (Methylsulfonyl)phenyl-2-(5H)-furanones as COX-2 inhibitors |
| US5756518A (en) * | 1996-04-02 | 1998-05-26 | Kowa Co., Ltd. | Phenylene derivatives |
| AU2077897A (en) * | 1996-04-10 | 1997-10-29 | Warner-Lambert Company | Nonpeptide endothelin antagonists with increased water solubility |
| US6005000A (en) * | 1996-08-22 | 1999-12-21 | Oxis International, Inc. | 5,5-Disubstituted-3, 4-dihydroxy-2(5H)-furanones and methods of use therefor |
| US6008243A (en) * | 1996-10-24 | 1999-12-28 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them, and their use |
| DZ3265A1 (fr) * | 1999-04-14 | 2000-10-19 | Pacific Corp | Derives de 4,5-diaryl-3(2h)-furanone comme inhibiteurs de cyclo-oxygenase-2 |
| US6576662B2 (en) * | 2000-05-05 | 2003-06-10 | Dr. Reddy's Laboratories Limited | Compounds having anticancer activity : process for their preparation and pharmaceutical compositions containing them |
-
2003
- 2003-01-28 US US10/354,474 patent/US6667330B2/en not_active Expired - Fee Related
- 2003-01-30 AU AU2003207750A patent/AU2003207750A2/en not_active Abandoned
- 2003-01-30 JP JP2003564026A patent/JP2006502963A/ja active Pending
- 2003-01-30 WO PCT/US2003/002766 patent/WO2003064403A1/en not_active Ceased
- 2003-01-30 CA CA002474871A patent/CA2474871A1/en not_active Abandoned
- 2003-01-30 EP EP03705988A patent/EP1478634A4/en not_active Withdrawn
- 2003-01-30 MX MXPA04007292A patent/MXPA04007292A/es unknown
- 2003-01-30 NZ NZ534305A patent/NZ534305A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6667330B2 (en) | 2003-12-23 |
| EP1478634A4 (en) | 2006-02-01 |
| MXPA04007292A (es) | 2005-12-12 |
| EP1478634A1 (en) | 2004-11-24 |
| CA2474871A1 (en) | 2003-08-07 |
| JP2006502963A (ja) | 2006-01-26 |
| US20030176361A1 (en) | 2003-09-18 |
| WO2003064403A1 (en) | 2003-08-07 |
| NZ534305A (en) | 2005-10-28 |
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| DA3 | Amendments made section 104 |
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