JP2011509298A5 - - Google Patents
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- JP2011509298A5 JP2011509298A5 JP2010542313A JP2010542313A JP2011509298A5 JP 2011509298 A5 JP2011509298 A5 JP 2011509298A5 JP 2010542313 A JP2010542313 A JP 2010542313A JP 2010542313 A JP2010542313 A JP 2010542313A JP 2011509298 A5 JP2011509298 A5 JP 2011509298A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- stereoisomer
- halogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 131
- 229910052736 halogen Chemical group 0.000 claims description 106
- 150000002367 halogens Chemical group 0.000 claims description 106
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 78
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 56
- 125000000623 heterocyclic group Chemical group 0.000 claims description 52
- 239000000090 biomarker Substances 0.000 claims description 44
- 230000007812 deficiency Effects 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 208000012268 mitochondrial disease Diseases 0.000 claims description 34
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 28
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 208000024412 Friedreich ataxia Diseases 0.000 claims description 20
- 208000032087 Hereditary Leber Optic Atrophy Diseases 0.000 claims description 20
- 201000000639 Leber hereditary optic neuropathy Diseases 0.000 claims description 20
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 150000003573 thiols Chemical class 0.000 claims description 16
- 230000002708 enhancing effect Effects 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 12
- 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 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 208000014644 Brain disease Diseases 0.000 claims description 10
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims description 10
- 102000015782 Electron Transport Complex III Human genes 0.000 claims description 10
- 108010024882 Electron Transport Complex III Proteins 0.000 claims description 10
- 208000032274 Encephalopathy Diseases 0.000 claims description 10
- 208000023105 Huntington disease Diseases 0.000 claims description 10
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims description 10
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims description 10
- 206010033799 Paralysis Diseases 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 10
- 208000012202 Pervasive developmental disease Diseases 0.000 claims description 10
- 208000029560 autism spectrum disease Diseases 0.000 claims description 10
- 230000001684 chronic effect Effects 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 10
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims description 10
- 210000003205 muscle Anatomy 0.000 claims description 10
- 201000006938 muscular dystrophy Diseases 0.000 claims description 10
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims description 10
- 208000021090 palsy Diseases 0.000 claims description 10
- 230000000750 progressive effect Effects 0.000 claims description 10
- 208000011580 syndromic disease Diseases 0.000 claims description 10
- 102000018832 Cytochromes Human genes 0.000 claims description 8
- 108010052832 Cytochromes Proteins 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 108010016626 Dipeptides Proteins 0.000 claims description 6
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 6
- 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 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 210000002381 plasma Anatomy 0.000 claims description 6
- 230000002861 ventricular Effects 0.000 claims description 6
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 4
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 4
- 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 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 230000029142 excretion Effects 0.000 claims description 2
- 230000036284 oxygen consumption Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229950007002 phosphocreatine Drugs 0.000 claims description 2
- 239000003642 reactive oxygen metabolite Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 40
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- -1 of claim 1 Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 40
- 0 CC(C)(CCc1c(*)c(*)c(C)c(*)c1O)O Chemical compound CC(C)(CCc1c(*)c(*)c(C)c(*)c1O)O 0.000 description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 2
- 125000004151 quinonyl group Chemical group 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1038708P | 2008-01-08 | 2008-01-08 | |
| US1040908P | 2008-01-08 | 2008-01-08 | |
| US61/010,387 | 2008-01-08 | ||
| US61/010,409 | 2008-01-08 | ||
| PCT/US2009/030229 WO2009089224A1 (en) | 2008-01-08 | 2009-01-06 | (HET) ARYL-p-QUINONE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013268441A Division JP2014058569A (ja) | 2008-01-08 | 2013-12-26 | ミトコンドリア病の処置のための（ヘテロ）アリール−ｐ−キノン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509298A JP2011509298A (ja) | 2011-03-24 |
| JP2011509298A5 true JP2011509298A5 (enExample) | 2013-02-28 |
| JP5649454B2 JP5649454B2 (ja) | 2015-01-07 |
Family
ID=40853439
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010542313A Expired - Fee Related JP5649454B2 (ja) | 2008-01-08 | 2009-01-06 | ミトコンドリア病の処置のための（ヘテロ）アリール−ｐ−キノン誘導体 |
| JP2013268441A Withdrawn JP2014058569A (ja) | 2008-01-08 | 2013-12-26 | ミトコンドリア病の処置のための（ヘテロ）アリール−ｐ−キノン誘導体 |
| JP2015236261A Withdrawn JP2016034979A (ja) | 2008-01-08 | 2015-12-03 | ミトコンドリア病の処置のための（ヘテロ）アリール−ｐ−キノン誘導体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013268441A Withdrawn JP2014058569A (ja) | 2008-01-08 | 2013-12-26 | ミトコンドリア病の処置のための（ヘテロ）アリール−ｐ−キノン誘導体 |
| JP2015236261A Withdrawn JP2016034979A (ja) | 2008-01-08 | 2015-12-03 | ミトコンドリア病の処置のための（ヘテロ）アリール−ｐ−キノン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8952071B2 (enExample) |
| EP (1) | EP2237664A4 (enExample) |
| JP (3) | JP5649454B2 (enExample) |
| CA (1) | CA2708961C (enExample) |
| EA (1) | EA023618B1 (enExample) |
| WO (1) | WO2009089224A1 (enExample) |
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| EP1986636B1 (en) | 2006-02-22 | 2013-04-24 | Edison Pharmaceuticals, Inc. | Phenol and 1,4-benzoquinone derivatives for use in the treatment of mitochondrial diseases |
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| EP2262508B1 (en) | 2008-03-05 | 2018-10-03 | BioElectron Technology Corporation | SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| CA2717741C (en) * | 2008-03-05 | 2018-04-03 | Edison Pharmaceuticals, Inc. | Treatment of hearing and balance impairments with redox-active therapeutics |
| CA2729227C (en) | 2008-06-25 | 2018-05-22 | Andrew W. Hinman | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
| MX363223B (es) | 2008-09-10 | 2019-03-15 | Bioelectron Tech Corp | Tratamiento de trastornos generalizados del desarrollo con terapeuticos con actividad redox. |
| CA2740773A1 (en) | 2008-10-14 | 2010-04-22 | Edison Pharmaceuticals, Inc. | Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells |
| ES2553557T3 (es) | 2008-10-28 | 2015-12-10 | Edison Pharmaceuticals, Inc. | Proceso para la producción de alfa-tocotrienol y derivados |
| PL2424495T3 (pl) | 2009-04-28 | 2018-06-29 | Bioelectron Technology Corporation | Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu |
| HUE037592T2 (hu) * | 2009-08-26 | 2018-09-28 | Bioelectron Tech Corp | Eljárások cerebrális ischemia megelõzésére és kezelésére |
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| KR102110175B1 (ko) | 2011-04-26 | 2020-05-13 | 레트로토프 인코포레이티드 | Ｐｕｆａ 산화와 관련된 장애 |
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| EP3943081A1 (en) | 2014-03-13 | 2022-01-26 | Retrotope, Inc. | Optic neuropathy treatment and reduction of steroid- induced oxidative stress with stabilized polyunsaturated substances |
| PL3233786T3 (pl) | 2014-12-16 | 2022-06-13 | Ptc Therapeutics, Inc. | Polimorficzne i amorficzne postacie (r)-2-hydroksy-2-metylo-4-(2,4,5-trimetylo-3,6-dioksocykloheksa-1,4-dienylo)butanoamidu |
| EP3390377A1 (en) | 2015-12-16 | 2018-10-24 | BioElectron Technology Corporation | 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 |
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| PL2424495T3 (pl) * | 2009-04-28 | 2018-06-29 | Bioelectron Technology Corporation | Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu |
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-
2009
- 2009-01-06 EP EP09700856.9A patent/EP2237664A4/en not_active Withdrawn
- 2009-01-06 US US12/811,694 patent/US8952071B2/en not_active Expired - Fee Related
- 2009-01-06 CA CA2708961A patent/CA2708961C/en not_active Expired - Fee Related
- 2009-01-06 EA EA201001119A patent/EA023618B1/ru not_active IP Right Cessation
- 2009-01-06 JP JP2010542313A patent/JP5649454B2/ja not_active Expired - Fee Related
- 2009-01-06 WO PCT/US2009/030229 patent/WO2009089224A1/en not_active Ceased
-
2013
- 2013-12-26 JP JP2013268441A patent/JP2014058569A/ja not_active Withdrawn
-
2014
- 2014-12-30 US US14/586,516 patent/US9486435B2/en not_active Expired - Fee Related
-
2015
- 2015-12-03 JP JP2015236261A patent/JP2016034979A/ja not_active Withdrawn
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