JP2015533794A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015533794A5 JP2015533794A5 JP2015531266A JP2015531266A JP2015533794A5 JP 2015533794 A5 JP2015533794 A5 JP 2015533794A5 JP 2015531266 A JP2015531266 A JP 2015531266A JP 2015531266 A JP2015531266 A JP 2015531266A JP 2015533794 A5 JP2015533794 A5 JP 2015533794A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dione
- compound
- dien
- deficiency
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 66
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 208000013200 Stress disease Diseases 0.000 claims description 28
- 230000036542 oxidative stress Effects 0.000 claims description 28
- -1 2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000000090 biomarker Substances 0.000 claims description 10
- 230000007812 deficiency Effects 0.000 claims description 10
- 208000012268 mitochondrial disease Diseases 0.000 claims description 10
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims description 7
- 208000006011 Stroke Diseases 0.000 claims description 7
- 208000001992 Autosomal Dominant Optic Atrophy Diseases 0.000 claims description 6
- 208000024412 Friedreich ataxia Diseases 0.000 claims description 6
- 208000014413 Maternally-inherited diabetes and deafness Diseases 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 208000029560 autism spectrum disease Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 208000014644 Brain disease Diseases 0.000 claims description 5
- 208000032274 Encephalopathy Diseases 0.000 claims description 5
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims description 5
- 208000002780 macular degeneration Diseases 0.000 claims description 5
- WMKDFHJGEGZOQZ-UHFFFAOYSA-N 13-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)trideca-5,8-dienenitrile Chemical compound CC1=C(C)C(=O)C(CCCCC=CCC=CCCCC#N)=C(C)C1=O WMKDFHJGEGZOQZ-UHFFFAOYSA-N 0.000 claims description 4
- SRZOVFGPTNSKBA-UHFFFAOYSA-N 13-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)trideca-5,8-dienoic acid Chemical compound CC1=C(C)C(=O)C(CCCCC=CCC=CCCCC(O)=O)=C(C)C1=O SRZOVFGPTNSKBA-UHFFFAOYSA-N 0.000 claims description 4
- WZDMDZDQIITTBR-UHFFFAOYSA-N 2-(10-hydroxydeca-5,8-dienyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C(CCCCC=CCC=CCO)=C(C)C1=O WZDMDZDQIITTBR-UHFFFAOYSA-N 0.000 claims description 4
- WAXIFTIATZBGGS-UHFFFAOYSA-N 2-(10-hydroxydeca-5,8-dienyl)-3-methylnaphthalene-1,4-dione Chemical compound CC1=C(CCCCC=CCC=CCO)C(=O)c2ccccc2C1=O WAXIFTIATZBGGS-UHFFFAOYSA-N 0.000 claims description 4
- DUSWGTOWKNQCKJ-UHFFFAOYSA-N 2-(12-hydroxydodeca-5,8-dienyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C(CCCCC=CCC=CCCCO)=C(C)C1=O DUSWGTOWKNQCKJ-UHFFFAOYSA-N 0.000 claims description 4
- 208000031229 Cardiomyopathies Diseases 0.000 claims description 4
- 206010058892 Carnitine deficiency Diseases 0.000 claims description 4
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims description 4
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims description 4
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims description 4
- 206010061323 Optic neuropathy Diseases 0.000 claims description 4
- 208000012202 Pervasive developmental disease Diseases 0.000 claims description 4
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- WDEABJKSGGRCQA-UHFFFAOYSA-N docebenone Chemical group CC1=C(C)C(=O)C(CCCCC#CCCCC#CCO)=C(C)C1=O WDEABJKSGGRCQA-UHFFFAOYSA-N 0.000 claims description 4
- 230000004064 dysfunction Effects 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 208000028867 ischemia Diseases 0.000 claims description 4
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims description 4
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims description 4
- 230000002438 mitochondrial effect Effects 0.000 claims description 4
- 208000020911 optic nerve disease Diseases 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims description 4
- 201000010866 very long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000020706 Autistic disease Diseases 0.000 claims description 3
- 206010011878 Deafness Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000035719 Maculopathy Diseases 0.000 claims description 3
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010061481 Renal injury Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 208000012130 acyl-CoA dehydrogenase deficiency Diseases 0.000 claims description 3
- 231100000895 deafness Toxicity 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 206010016256 fatigue Diseases 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 208000016354 hearing loss disease Diseases 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 208000003918 Acute Kidney Tubular Necrosis Diseases 0.000 claims description 2
- 208000036640 Asperger disease Diseases 0.000 claims description 2
- 201000006062 Asperger syndrome Diseases 0.000 claims description 2
- 206010003591 Ataxia Diseases 0.000 claims description 2
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- 108700005857 Carnitine palmitoyl transferase 1A deficiency Proteins 0.000 claims description 2
- 208000005359 Carnitine palmitoyl transferase 1A deficiency Diseases 0.000 claims description 2
- 108700005858 Carnitine palmitoyl transferase 2 deficiency Proteins 0.000 claims description 2
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims description 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 2
- 206010010904 Convulsion Diseases 0.000 claims description 2
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims description 2
- 101710088194 Dehydrogenase Proteins 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims description 2
- 201000010374 Down Syndrome Diseases 0.000 claims description 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 101000804964 Homo sapiens DNA polymerase subunit gamma-1 Proteins 0.000 claims description 2
- 101001083553 Homo sapiens Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Proteins 0.000 claims description 2
- 101000841267 Homo sapiens Long chain 3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 claims description 2
- 101000595929 Homo sapiens POLG alternative reading frame Proteins 0.000 claims description 2
- 102100030358 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Human genes 0.000 claims description 2
- 208000026350 Inborn Genetic disease Diseases 0.000 claims description 2
- 102100029107 Long chain 3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 claims description 2
- 108010027062 Long-Chain Acyl-CoA Dehydrogenase Proteins 0.000 claims description 2
- 102000018653 Long-Chain Acyl-CoA Dehydrogenase Human genes 0.000 claims description 2
- 102100021644 Long-chain specific acyl-CoA dehydrogenase, mitochondrial Human genes 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- 206010059521 Methylmalonic aciduria Diseases 0.000 claims description 2
- 206010059396 Mitochondrial DNA depletion Diseases 0.000 claims description 2
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
- 206010028289 Muscle atrophy Diseases 0.000 claims description 2
- 208000021642 Muscular disease Diseases 0.000 claims description 2
- 201000009623 Myopathy Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 102100035196 POLG alternative reading frame Human genes 0.000 claims description 2
- 206010033799 Paralysis Diseases 0.000 claims description 2
- 208000013234 Pearson syndrome Diseases 0.000 claims description 2
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims description 2
- 206010038540 Renal tubular necrosis Diseases 0.000 claims description 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 2
- 208000006289 Rett Syndrome Diseases 0.000 claims description 2
- 208000036353 Rett disease Diseases 0.000 claims description 2
- 208000002903 Thalassemia Diseases 0.000 claims description 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 2
- 208000016620 Tourette disease Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
- 208000004622 abetalipoproteinemia Diseases 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 201000004010 carnitine palmitoyltransferase I deficiency Diseases 0.000 claims description 2
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000035110 classic form autosomal dominant optic atrophy Diseases 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 208000016361 genetic disease Diseases 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 208000006443 lactic acidosis Diseases 0.000 claims description 2
- 208000036546 leukodystrophy Diseases 0.000 claims description 2
- 201000003694 methylmalonic acidemia Diseases 0.000 claims description 2
- 208000005264 motor neuron disease Diseases 0.000 claims description 2
- 210000003205 muscle Anatomy 0.000 claims description 2
- 230000020763 muscle atrophy Effects 0.000 claims description 2
- 201000000585 muscular atrophy Diseases 0.000 claims description 2
- 230000035772 mutation Effects 0.000 claims description 2
- 201000001119 neuropathy Diseases 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 208000021090 palsy Diseases 0.000 claims description 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 2
- 230000035806 respiratory chain Effects 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 208000024825 childhood disintegrative disease Diseases 0.000 claims 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
- 208000019932 Aciduria Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 206010047513 Vision blurred Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 229960004203 carnitine Drugs 0.000 claims 1
- ASARMUCNOOHMLO-WLORSUFZSA-L cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2s)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O ASARMUCNOOHMLO-WLORSUFZSA-L 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 208000034737 hemoglobinopathy Diseases 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 208000018337 inherited hemoglobinopathy Diseases 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 230000010410 reperfusion Effects 0.000 claims 1
- 208000032253 retinal ischemia Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
- 238000003556 assay Methods 0.000 description 6
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 6
- 235000017471 coenzyme Q10 Nutrition 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 210000002381 plasma Anatomy 0.000 description 5
- 230000002861 ventricular Effects 0.000 description 5
- 102000018832 Cytochromes Human genes 0.000 description 4
- 108010052832 Cytochromes Proteins 0.000 description 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 4
- 235000018417 cysteine Nutrition 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 4
- 108010024636 Glutathione Proteins 0.000 description 3
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 3
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 108010053070 Glutathione Disulfide Proteins 0.000 description 2
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 description 2
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- YPZRWBKMTBYPTK-BJDJZHNGSA-N glutathione disulfide Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(=O)NCC(O)=O)CSSC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O YPZRWBKMTBYPTK-BJDJZHNGSA-N 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- 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 2
- YPZRWBKMTBYPTK-UHFFFAOYSA-N oxidized gamma-L-glutamyl-L-cysteinylglycine Natural products OC(=O)C(N)CCC(=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(O)=O YPZRWBKMTBYPTK-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- HWKRAUXFMLQKLS-UHFFFAOYSA-N 2-oxidanylidenepropanoic acid Chemical compound CC(=O)C(O)=O.CC(=O)C(O)=O HWKRAUXFMLQKLS-UHFFFAOYSA-N 0.000 description 1
- KVZLHPXEUGJPAH-UHFFFAOYSA-N 2-oxidanylpropanoic acid Chemical compound CC(O)C(O)=O.CC(O)C(O)=O KVZLHPXEUGJPAH-UHFFFAOYSA-N 0.000 description 1
- HCAJQHYUCKICQH-VPENINKCSA-N 8-Oxo-7,8-dihydro-2'-deoxyguanosine Chemical compound C1=2NC(N)=NC(=O)C=2NC(=O)N1[C@H]1C[C@H](O)[C@@H](CO)O1 HCAJQHYUCKICQH-VPENINKCSA-N 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
- 208000023434 Alpers-Huttenlocher syndrome Diseases 0.000 description 1
- 206010011903 Deafness traumatic Diseases 0.000 description 1
- 102000015782 Electron Transport Complex III Human genes 0.000 description 1
- 108010024882 Electron Transport Complex III Proteins 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000208822 Lactuca Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 208000026072 Motor neurone disease Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 208000002946 Noise-Induced Hearing Loss Diseases 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- 206010057430 Retinal injury Diseases 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 230000007950 acidosis Effects 0.000 description 1
- 208000026545 acidosis disease Diseases 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 208000038015 macular disease Diseases 0.000 description 1
- 201000007998 methylmalonic aciduria and homocystinuria type cblC Diseases 0.000 description 1
- 201000011540 mitochondrial DNA depletion syndrome 4a Diseases 0.000 description 1
- 201000003645 multiple acyl-CoA dehydrogenase deficiency Diseases 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 229950007002 phosphocreatine Drugs 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 208000029257 vision disease Diseases 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261698431P | 2012-09-07 | 2012-09-07 | |
| US61/698,431 | 2012-09-07 | ||
| US201361792797P | 2013-03-15 | 2013-03-15 | |
| US61/792,797 | 2013-03-15 | ||
| PCT/US2013/058637 WO2014039917A1 (en) | 2012-09-07 | 2013-09-06 | Benzoquinone derivatives for treating oxidative stress disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015533794A JP2015533794A (ja) | 2015-11-26 |
| JP2015533794A5 true JP2015533794A5 (https=) | 2016-10-27 |
Family
ID=49170942
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015531266A Ceased JP2015533794A (ja) | 2012-09-07 | 2013-09-06 | 酸化ストレス障害を処置するためのベンゾキノン誘導体 |
| JP2015531249A Expired - Fee Related JP6393684B2 (ja) | 2012-09-07 | 2013-09-06 | 個体のレドックス状態の調節において使用するためのキノン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015531249A Expired - Fee Related JP6393684B2 (ja) | 2012-09-07 | 2013-09-06 | 個体のレドックス状態の調節において使用するためのキノン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US20150216820A1 (https=) |
| EP (2) | EP2892516A1 (https=) |
| JP (2) | JP2015533794A (https=) |
| CA (2) | CA2883879A1 (https=) |
| HK (1) | HK1211872A1 (https=) |
| WO (2) | WO2014039917A1 (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP2344142B1 (en) | 2008-09-10 | 2024-06-26 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| 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 |
| WO2012174286A1 (en) | 2011-06-14 | 2012-12-20 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| 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 |
| CA2883879A1 (en) * | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| US10189830B2 (en) | 2013-03-15 | 2019-01-29 | Bioelectron Technology Corporation | Alkyl-heteroaryl substituted quinone derivatives for treatment of oxidative stress disorders |
| 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 |
| AU2014273891A1 (en) | 2013-05-31 | 2015-12-24 | Bioelectron Technology Corporation | Carboxylic acid derivatives for treatment of oxidative stress disorders |
| WO2015183963A2 (en) * | 2014-05-28 | 2015-12-03 | Stealth Peptides International, Inc. | Therapeutic compositions including redox-active parabenzoquinones and uses thereof |
| 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 |
| WO2017087795A1 (en) | 2015-11-19 | 2017-05-26 | Concert Pharmaceuticals, Inc. | Deuterated epi-743 |
| 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 |
| JP2019501974A (ja) * | 2016-01-12 | 2019-01-24 | バイオエレクトロン テクノロジー コーポレイション | チオスルフェートレベルを増加させるためのまたは硫化水素レベルを低下させるためのトコフェロールキノン誘導体およびトコトリエノールキノン誘導体 |
| US10707531B1 (en) | 2016-09-27 | 2020-07-07 | New Dominion Enterprises Inc. | All-inorganic solvents for electrolytes |
| 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 |
| WO2018129411A1 (en) | 2017-01-06 | 2018-07-12 | Bioelectron Technology Corporation | Aryl- and heteroaryl-resorufin derivatives for treatment of oxidative stress disorders and liver and kidney disorders |
| 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 |
| WO2020252414A1 (en) | 2019-06-13 | 2020-12-17 | Ptc Therapeutics, Inc. | Naphthoquinone derivatives for treatment of oxidative stress disorders |
| CN114746430B (zh) | 2019-10-04 | 2026-01-30 | 康德生物医疗有限公司 | 治疗线粒体异常疾病的伐替苯醌的醌-、氢醌-和萘醌-类似物 |
| US12037350B2 (en) | 2020-04-03 | 2024-07-16 | Stealth Biotherapeutics Inc. | Compositions and methods for the prevention and/or treatment of mitochondrial disease, including Friedreich's ataxia |
| KR20230043923A (ko) * | 2020-08-07 | 2023-03-31 | 다이호야쿠힌고교 가부시키가이샤 | 신규 시클로알케논 화합물 또는 그의 염 |
| 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 |
| US20250312360A1 (en) * | 2022-05-13 | 2025-10-09 | Virginia Tech Intellectual Properties, Inc. | Mitochondrial antioxidant treatment for cask-linked neurodevelopmental disorders |
| WO2024259130A1 (en) * | 2023-06-16 | 2024-12-19 | Ptc Therapeutics, Inc. | Methods for increasing vatiquinone plasma exposure with food |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5621021B2 (https=) | 1973-12-19 | 1981-05-16 | ||
| DE3060165D1 (en) | 1979-03-08 | 1982-03-11 | Hoffmann La Roche | Process for the stereospecific preparation of compounds of the vitamin k1- and k2-series, as well as new starting materials for the process |
| JPS5640651A (en) | 1979-09-12 | 1981-04-16 | Takeda Chem Ind Ltd | Quinone compound and its preparation |
| JPS57109739A (en) * | 1980-12-27 | 1982-07-08 | Takeda Chem Ind Ltd | Quinone compound and its preparation |
| US4393075A (en) | 1980-04-14 | 1983-07-12 | Takeda Chemical Industries, Ltd. | Quinone compounds and their use in suppressing the production of SRS-A in mammals |
| JPS5910541A (ja) * | 1982-07-09 | 1984-01-20 | Takeda Chem Ind Ltd | キノン化合物 |
| DE3362008D1 (en) | 1982-07-09 | 1986-03-13 | Takeda Chemical Industries Ltd | Quinone compounds, their production and use |
| JPS6143132A (ja) * | 1984-08-06 | 1986-03-01 | Takeda Chem Ind Ltd | キノン誘導体,その製造法およびそれを含んでなる医薬組成物 |
| JPS62294636A (ja) | 1986-05-21 | 1987-12-22 | Eisai Co Ltd | 2−メチル−1,4−ナフトキノンの製造法 |
| IE904264A1 (en) | 1989-11-28 | 1991-06-05 | Nippon Catalytic Chem Ind | Process for preparation of 2-substituted-1,4-naphthoquinone |
| JPH06312950A (ja) | 1993-03-01 | 1994-11-08 | Eezai Kagaku Kk | キノン誘導体の製造法および中間体 |
| US5318993A (en) | 1993-04-16 | 1994-06-07 | Bristol-Myers Squibb Company | Antihyperlipidemic benzoquinones |
| CA2117412A1 (en) | 1993-07-26 | 1995-01-27 | Eisai Co., Ltd. | Preparation process of naphthoquinone derivative and intermediate for the preparation thereof |
| EP0750496A1 (en) | 1994-03-14 | 1997-01-02 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | Use of lipoxygenase inhibitors as anti-cancer therapeutic and intervention agents |
| US5637741A (en) | 1994-09-27 | 1997-06-10 | Kuraray Co., Ltd. | Process for producing 2-methyl-1,4-naphthoquinone |
| KR0178456B1 (ko) | 1996-04-25 | 1999-05-15 | 김흥기 | 2-메틸-1,4-나프토퀴논(비타민 k3)의 제조방법 |
| CA2272971C (en) * | 1998-10-29 | 2008-01-15 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Quinone derivatives for treating or preventing diseases associated with iron overload |
| US7034054B2 (en) | 2000-12-15 | 2006-04-25 | Galileo Pharmaceuticals, Inc. | Methods for the prevention and treatment of cerebral ischemia using non-alpha tocopherols |
| WO2002056823A2 (en) * | 2001-01-18 | 2002-07-25 | Arnold Hoffman | Redox therapy for tumors |
| US6579994B2 (en) | 2001-03-29 | 2003-06-17 | Council Of Scientific And Industrial Research | Process for preparation of 2-Methyl-1,4-naphthoquinone |
| GB0117326D0 (en) | 2001-07-16 | 2001-09-05 | Univ Aberdeen | Napthoquinone-type inhibitors of protein aggregation |
| NZ513547A (en) | 2001-08-13 | 2002-09-27 | Antipodean Biotechnology Ltd | Synthesis of triphenylphosphonium quinols (e.g. mitoquinol) and/or quinones (e.g. mitoquinone) |
| JP2003226639A (ja) | 2002-01-31 | 2003-08-12 | Hisamitsu Pharmaceut Co Inc | 神経成長因子活性増強剤としてのビタミンk類を含む医薬組成物およびその使用 |
| DE60211875T2 (de) | 2002-07-01 | 2006-10-26 | Santhera Pharmaceuticals (Schweiz) Ag | Screeningverfahren und Verbindungen zur Behandlung von Friedreich ataxia |
| JP4599292B2 (ja) | 2002-10-30 | 2010-12-15 | 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 | 物理的−化学的特性に基づく治療用化合物の同定 |
| US20040087527A1 (en) | 2002-10-31 | 2004-05-06 | Day Brian J. | Methods for treatment of thiol-containing compound deficient conditions |
| WO2005033092A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | Chroman derivatives |
| 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 |
| CA2622523C (en) | 2005-09-15 | 2014-02-18 | Edison Pharmaceuticals, Inc. | Tail variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| RU2318500C2 (ru) | 2005-10-18 | 2008-03-10 | Общество С Ограниченной Ответственностью "Митотехнология" | Способ воздействия на организм путем адресной доставки биологически активных веществ в митохондрии, фармацевтическая композиция для его осуществления и соединение, применяемое для этой цели |
| 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 |
| CN101139272A (zh) | 2006-09-08 | 2008-03-12 | 南京莱因医药科技有限公司 | 维生素k2的合成方法 |
| CA2606658A1 (en) * | 2006-10-13 | 2008-04-13 | Mike Tyers | Compositions and methods for treating neurological disorders or damage |
| KR20080047959A (ko) | 2006-11-27 | 2008-05-30 | 주식회사 엠디바이오알파 | 비만, 당뇨, 대사성 질환, 퇴행성 질환 및 미토콘드리아이상 질환의 치료 또는 예방을 위한 나프토퀴논계 약제조성물 |
| 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 |
| EP2262519A4 (en) | 2008-03-05 | 2011-03-23 | Edison Pharmaceuticals Inc | TREATMENT OF HEARING AND BALANCING DISORDERS WITH REDOXACTIVE THERAPEUTICS |
| 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 |
| JP2012525397A (ja) | 2009-04-28 | 2012-10-22 | 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 | 眼科疾患を治療するためのトコトリエノールキノンの製剤 |
| PL2424495T3 (pl) | 2009-04-28 | 2018-06-29 | Bioelectron Technology Corporation | Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu |
| DK2470168T3 (en) * | 2009-08-26 | 2018-05-07 | Bioelectron Tech Corp | PROCEDURES FOR PREVENTION AND TREATMENT OF CEREBRAL ISCAM |
| WO2011041452A2 (en) * | 2009-10-01 | 2011-04-07 | Ampere Life Sciences, Inc. | Mouse model for identifying compounds for the treatment of oxidative stress |
| US20110172312A1 (en) | 2009-12-31 | 2011-07-14 | Miller Guy M | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| SG184787A1 (en) * | 2010-03-09 | 2012-11-29 | Edison Pharmaceuticals Inc | Synthesis of alpha-tocopherolquinone derivatives, and methods of using the same |
| CA2797581A1 (en) * | 2010-04-27 | 2011-11-03 | Edison Pharmaceuticals, Inc. | Formulations of quinones for the treatment of ophthalmic diseases |
| EP2601168A4 (en) | 2010-08-06 | 2013-12-04 | Ampere Life Sciences Inc | TREATMENT OF MITOCHONDRIAL DISEASES BY VITAMIN K |
| EA201300215A1 (ru) | 2010-08-06 | 2013-07-30 | Эдисон Фармасьютикалз, Инк. | Лечение митохондриальных болезней нафтохинонами |
| DK2605769T3 (en) * | 2010-08-16 | 2016-10-24 | Santhera Pharmaceuticals (Schweiz) Ag | Benzoquinonderivater for the treatment of mitochondrial diseases of the eye |
| WO2012170773A1 (en) | 2011-06-08 | 2012-12-13 | Edison Pharmaceuticals, Inc. | Adjunctive therapy for the treatment of mitochondrial disorders with quinones and naphthoquinones |
| WO2012174286A1 (en) | 2011-06-14 | 2012-12-20 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| US20150057363A1 (en) | 2011-07-06 | 2015-02-26 | Guy M. Miller | Treatment of methylmalonic aciduria, isovaleric aciduria, and other organic acidurias with tocotrienol quinones |
| 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 |
| CN103841969A (zh) | 2011-08-04 | 2014-06-04 | 美国卫生和人力服务部 | 经由药物介导的对类二十烷酸平衡的操作治疗和预防微生物介导的疾病 |
| JP5076021B1 (ja) | 2011-11-17 | 2012-11-21 | 株式会社東芝 | 電子機器、電子機器の制御方法、電子機器の制御プログラム |
| CA2883879A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| US9296712B2 (en) | 2013-03-15 | 2016-03-29 | Edison Pharmaceuticals, Inc. | 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 |
| US10189830B2 (en) | 2013-03-15 | 2019-01-29 | Bioelectron Technology Corporation | Alkyl-heteroaryl substituted quinone 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 |
| US20140275045A1 (en) | 2013-03-15 | 2014-09-18 | Edison Pharmaceuticals, Inc. | Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders |
| AU2014273891A1 (en) | 2013-05-31 | 2015-12-24 | Bioelectron Technology Corporation | Carboxylic acid derivatives for treatment of oxidative stress disorders |
-
2013
- 2013-09-06 CA CA2883879A patent/CA2883879A1/en not_active Abandoned
- 2013-09-06 CA CA2883882A patent/CA2883882A1/en not_active Abandoned
- 2013-09-06 US US14/426,130 patent/US20150216820A1/en not_active Abandoned
- 2013-09-06 US US14/426,135 patent/US9629815B2/en not_active Expired - Fee Related
- 2013-09-06 EP EP13765880.3A patent/EP2892516A1/en not_active Withdrawn
- 2013-09-06 WO PCT/US2013/058637 patent/WO2014039917A1/en not_active Ceased
- 2013-09-06 JP JP2015531266A patent/JP2015533794A/ja not_active Ceased
- 2013-09-06 EP EP13762705.5A patent/EP2892515A1/en not_active Withdrawn
- 2013-09-06 JP JP2015531249A patent/JP6393684B2/ja not_active Expired - Fee Related
- 2013-09-06 HK HK16100029.7A patent/HK1211872A1/xx unknown
- 2013-09-06 WO PCT/US2013/058568 patent/WO2014039862A1/en not_active Ceased
-
2017
- 2017-04-10 US US15/483,933 patent/US20170209393A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015533794A5 (https=) | ||
| JP2016515526A5 (https=) | ||
| JP2016520621A5 (https=) | ||
| JP2016515527A5 (https=) | ||
| JP2016514697A5 (https=) | ||
| AU2008242827B2 (en) | Pharmaceutical formulations containing lipoic acid derivatives | |
| US9629815B2 (en) | Benzoquinone derivatives for treating oxidative stress disorders | |
| US10981855B2 (en) | Fluoroalkyl, fluoroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders | |
| JP2015527400A5 (https=) | ||
| US11685757B2 (en) | Pharmaceutical co-crystal composition and use thereof | |
| US9296712B2 (en) | Resorufin derivatives for treatment of oxidative stress disorders | |
| JP2013541502A5 (https=) | ||
| RU2017124714A (ru) | Полиморфные и аморфные (r)-2-гидрокси-2-метил-4-(2,4,5-триметил-3,6-диоксоциклогекса-1,4-диенил)бутанамида | |
| JP2011525926A5 (https=) | ||
| JP2013224330A (ja) | ミトコンドリア病および他の症状の処置のためのレドックス活性化治療の側鎖変異体およびエネルギーバイオマーカーの調節 | |
| JP2009541269A5 (https=) | ||
| EA024993B1 (ru) | Этинильные производные в качестве модуляторов метаботропного глутаматного рецептора | |
| CA2988992A1 (en) | Pharmaceutical composition of carboplatin based co-crystals and use thereof | |
| JPWO2020014504A5 (https=) | ||
| EP0331061A1 (de) | Substituierte Hydrazone und diese enthaltende Fungizide | |
| US20140194478A1 (en) | Compositions for treatment of cancer |