JP2012525399A5 - - Google Patents
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- JP2012525399A5 JP2012525399A5 JP2012508609A JP2012508609A JP2012525399A5 JP 2012525399 A5 JP2012525399 A5 JP 2012525399A5 JP 2012508609 A JP2012508609 A JP 2012508609A JP 2012508609 A JP2012508609 A JP 2012508609A JP 2012525399 A5 JP2012525399 A5 JP 2012525399A5
- Authority
- JP
- Japan
- Prior art keywords
- tocotrienol
- alpha
- pharmaceutical composition
- composition according
- hydroquinone
- 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- Withdrawn
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 36
- 208000032087 Hereditary Leber Optic Atrophy Diseases 0.000 claims description 24
- 201000000639 Leber hereditary optic neuropathy Diseases 0.000 claims description 24
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 22
- LNOVHERIIMJMDG-KTWAZNHYSA-N 2-[(6e,10e)-3-hydroxy-3,7,11,15-tetramethylhexadeca-6,10,14-trienyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LNOVHERIIMJMDG-KTWAZNHYSA-N 0.000 claims description 17
- 229930003802 tocotrienol Natural products 0.000 claims description 15
- 239000011731 tocotrienol Substances 0.000 claims description 15
- 235000019148 tocotrienols Nutrition 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 230000035772 mutation Effects 0.000 claims description 14
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 claims description 13
- RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 208000001799 Hereditary Optic Atrophies Diseases 0.000 claims description 8
- 229940064063 alpha tocotrienol Drugs 0.000 claims description 7
- RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 claims description 7
- 235000019145 α-tocotrienol Nutrition 0.000 claims description 7
- 239000011730 α-tocotrienol Substances 0.000 claims description 7
- OTXNTMVVOOBZCV-UHFFFAOYSA-N 2R-gamma-tocotrienol Natural products OC1=C(C)C(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-UHFFFAOYSA-N 0.000 claims description 6
- 210000003733 optic disk Anatomy 0.000 claims description 6
- FGYKUFVNYVMTAM-UHFFFAOYSA-N (R)-2,5,8-trimethyl-2-(4,8,12-trimethyl-trideca-3t,7t,11-trienyl)-chroman-6-ol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-UHFFFAOYSA-N 0.000 claims description 4
- 101150045559 Opa1 gene Proteins 0.000 claims description 4
- FGYKUFVNYVMTAM-YMCDKREISA-N beta-Tocotrienol Natural products Oc1c(C)c2c(c(C)c1)O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CC2 FGYKUFVNYVMTAM-YMCDKREISA-N 0.000 claims description 4
- FGYKUFVNYVMTAM-MUUNZHRXSA-N epsilon-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-MUUNZHRXSA-N 0.000 claims description 4
- OTXNTMVVOOBZCV-YMCDKREISA-N gamma-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CCc2c1 OTXNTMVVOOBZCV-YMCDKREISA-N 0.000 claims description 4
- 230000005787 mitochondrial ATP synthesis coupled electron transport Effects 0.000 claims description 4
- 208000001749 optic atrophy Diseases 0.000 claims description 4
- 235000019151 β-tocotrienol Nutrition 0.000 claims description 4
- 239000011723 β-tocotrienol Substances 0.000 claims description 4
- FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 claims description 4
- 235000019150 γ-tocotrienol Nutrition 0.000 claims description 4
- 239000011722 γ-tocotrienol Substances 0.000 claims description 4
- OTXNTMVVOOBZCV-WAZJVIJMSA-N γ-tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-WAZJVIJMSA-N 0.000 claims description 4
- 206010033546 Pallor Diseases 0.000 claims description 3
- 206010043189 Telangiectasia Diseases 0.000 claims description 3
- 230000004456 color vision Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000004064 dysfunction Effects 0.000 claims description 3
- 230000004438 eyesight Effects 0.000 claims description 3
- 230000004298 light response Effects 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 206010062198 microangiopathy Diseases 0.000 claims description 3
- 210000004126 nerve fiber Anatomy 0.000 claims description 3
- 210000002445 nipple Anatomy 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 230000001179 pupillary effect Effects 0.000 claims description 3
- 230000002207 retinal effect Effects 0.000 claims description 3
- 230000008961 swelling Effects 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- 208000009056 telangiectasis Diseases 0.000 claims description 3
- 230000004304 visual acuity Effects 0.000 claims description 3
- SFVAYPRWECRHTF-QRCIITMISA-N 2-[(6e,10e)-3-hydroxy-3,7,11,15-tetramethylhexadeca-6,10,14-trienyl]-6-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)CCC1=CC(=O)C=C(C)C1=O SFVAYPRWECRHTF-QRCIITMISA-N 0.000 claims description 2
- ODADKLYLWWCHNB-UHFFFAOYSA-N 2R-delta-tocotrienol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-UHFFFAOYSA-N 0.000 claims description 2
- 208000033707 Early-onset X-linked optic atrophy Diseases 0.000 claims description 2
- 101000722054 Homo sapiens Dynamin-like 120 kDa protein, mitochondrial Proteins 0.000 claims description 2
- 101000614988 Homo sapiens Mediator of RNA polymerase II transcription subunit 12 Proteins 0.000 claims description 2
- 101000640713 Homo sapiens Transmembrane protein 126A Proteins 0.000 claims description 2
- 102100021070 Mediator of RNA polymerase II transcription subunit 12 Human genes 0.000 claims description 2
- 102100033846 Transmembrane protein 126A Human genes 0.000 claims description 2
- BTNBMQIHCRIGOU-UHFFFAOYSA-N delta-tocotrienol Natural products CC(=CCCC(=CCCC(=CCCOC1(C)CCc2cc(O)cc(C)c2O1)C)C)C BTNBMQIHCRIGOU-UHFFFAOYSA-N 0.000 claims description 2
- 101150031431 opa gene Proteins 0.000 claims description 2
- 208000025019 optic atrophy 2 Diseases 0.000 claims description 2
- 208000009689 optic atrophy 4 Diseases 0.000 claims description 2
- 208000006042 optic atrophy 5 Diseases 0.000 claims description 2
- 208000006497 optic atrophy 6 Diseases 0.000 claims description 2
- 208000009606 optic atrophy 7 Diseases 0.000 claims description 2
- 210000001525 retina Anatomy 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 235000019144 δ-tocotrienol Nutrition 0.000 claims description 2
- 239000011729 δ-tocotrienol Substances 0.000 claims description 2
- ODADKLYLWWCHNB-LDYBVBFYSA-N δ-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-LDYBVBFYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 239000002775 capsule Substances 0.000 claims 1
- 210000001328 optic nerve Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 description 16
- 238000009472 formulation Methods 0.000 description 8
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 206010061323 Optic neuropathy Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 208000020911 optic nerve disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21479509P | 2009-04-28 | 2009-04-28 | |
| US61/214,795 | 2009-04-28 | ||
| US31873310P | 2010-03-29 | 2010-03-29 | |
| US61/318,733 | 2010-03-29 | ||
| PCT/US2010/032624 WO2010126911A1 (en) | 2009-04-28 | 2010-04-27 | Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014226669A Division JP2015028084A (ja) | 2009-04-28 | 2014-11-07 | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012525399A JP2012525399A (ja) | 2012-10-22 |
| JP2012525399A5 true JP2012525399A5 (https=) | 2013-07-11 |
Family
ID=42244195
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012508609A Withdrawn JP2012525399A (ja) | 2009-04-28 | 2010-04-27 | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
| JP2014226669A Withdrawn JP2015028084A (ja) | 2009-04-28 | 2014-11-07 | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
| JP2016183749A Pending JP2016216506A (ja) | 2009-04-28 | 2016-09-21 | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014226669A Withdrawn JP2015028084A (ja) | 2009-04-28 | 2014-11-07 | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
| JP2016183749A Pending JP2016216506A (ja) | 2009-04-28 | 2016-09-21 | トコトリエノールキノンを用いる、レーバー遺伝性視神経症および優性遺伝性視神経萎縮症の治療 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US20100273894A1 (https=) |
| EP (2) | EP2424495B1 (https=) |
| JP (3) | JP2012525399A (https=) |
| BR (1) | BRPI1013376A8 (https=) |
| CA (1) | CA2777479C (https=) |
| DK (1) | DK2424495T3 (https=) |
| EA (1) | EA031126B1 (https=) |
| ES (1) | ES2662051T3 (https=) |
| HU (1) | HUE037574T2 (https=) |
| MX (1) | MX336800B (https=) |
| NO (1) | NO2424495T3 (https=) |
| PL (1) | PL2424495T3 (https=) |
| PT (1) | PT2424495T (https=) |
| SI (1) | SI2424495T1 (https=) |
| WO (1) | WO2010126911A1 (https=) |
Families Citing this family (32)
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| 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 |
| 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 |
| DK2470168T3 (en) * | 2009-08-26 | 2018-05-07 | Bioelectron Tech Corp | PROCEDURES FOR PREVENTION AND TREATMENT OF CEREBRAL ISCAM |
| US20110172312A1 (en) * | 2009-12-31 | 2011-07-14 | Miller Guy M | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| US9114120B2 (en) | 2010-11-22 | 2015-08-25 | Sigma-Tau Industrie Farmaceutiche Riunite, S.P.A. | Therapeutical method for the treatment of the Leber optic neuropathy |
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| 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 |
| WO2014001889A1 (en) | 2012-06-29 | 2014-01-03 | Raouf Rekik | Angiotensin converting enzyme inhibitors for treating optic neuropathy or congenital optic atrophy |
| CA2883879A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| 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 |
| US9296712B2 (en) | 2013-03-15 | 2016-03-29 | Edison Pharmaceuticals, Inc. | Resorufin 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 |
| CA2936146A1 (en) * | 2014-01-06 | 2015-07-09 | Stealth Biotherapeutics Corp | Methods and compositions for preventing or treating dominant optic atrophy |
| 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 |
| BR112017025839A2 (en) * | 2015-06-05 | 2018-08-14 | Fundació Hospital Universitari Vall D'hebron - Institut De Recerca | treatment of mitochondrial diseases |
| 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 |
| CN112888419A (zh) * | 2018-10-11 | 2021-06-01 | 安布里亚制药公司 | 用于治疗和预防Leber遗传性视神经病变的组合物和方法 |
| RU2704013C1 (ru) * | 2019-04-18 | 2019-10-23 | ФГБНУ "НИИ глазных болезней" | Способ коррекции окислительного стресса при наследственной оптической нейропатии Лебера |
| CN112385783B (zh) | 2020-10-10 | 2022-07-05 | 南京农业大学 | 一种控制炭烤肉中多环芳烃含量的烤制方法 |
| WO2024259130A1 (en) * | 2023-06-16 | 2024-12-19 | Ptc Therapeutics, Inc. | Methods for increasing vatiquinone plasma exposure with food |
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-
2010
- 2010-04-27 PL PL10715650T patent/PL2424495T3/pl unknown
- 2010-04-27 WO PCT/US2010/032624 patent/WO2010126911A1/en not_active Ceased
- 2010-04-27 DK DK10715650.7T patent/DK2424495T3/en active
- 2010-04-27 CA CA2777479A patent/CA2777479C/en not_active Expired - Fee Related
- 2010-04-27 ES ES10715650.7T patent/ES2662051T3/es active Active
- 2010-04-27 EP EP10715650.7A patent/EP2424495B1/en not_active Not-in-force
- 2010-04-27 MX MX2011011309A patent/MX336800B/es active IP Right Grant
- 2010-04-27 US US12/768,565 patent/US20100273894A1/en not_active Abandoned
- 2010-04-27 PT PT107156507T patent/PT2424495T/pt unknown
- 2010-04-27 SI SI201031630T patent/SI2424495T1/en unknown
- 2010-04-27 EP EP18151731.9A patent/EP3332766A1/en not_active Withdrawn
- 2010-04-27 HU HUE10715650A patent/HUE037574T2/hu unknown
- 2010-04-27 BR BRPI1013376A patent/BRPI1013376A8/pt not_active Application Discontinuation
- 2010-04-27 EA EA201101575A patent/EA031126B1/ru not_active IP Right Cessation
- 2010-04-27 NO NO10715650A patent/NO2424495T3/no unknown
- 2010-04-27 JP JP2012508609A patent/JP2012525399A/ja not_active Withdrawn
-
2013
- 2013-04-09 US US13/859,592 patent/US9370496B2/en active Active
-
2014
- 2014-11-07 JP JP2014226669A patent/JP2015028084A/ja not_active Withdrawn
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2016
- 2016-06-09 US US15/178,423 patent/US10195161B2/en not_active Expired - Fee Related
- 2016-09-21 JP JP2016183749A patent/JP2016216506A/ja active Pending
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