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- Withdrawn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) | EP3332766A1 (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=) |
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| WO2007100652A2 (en) | 2006-02-22 | 2007-09-07 | Edison Pharmaceuticals, Inc. | Side chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| EA038941B1 (ru) | 2007-11-06 | 2021-11-12 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | ПРОИЗВОДНЫЕ 4-(п-ХИНОНИЛ)-2-ГИДРОКСИБУТАНАМИДА ДЛЯ ЛЕЧЕНИЯ МИТОХОНДРИАЛЬНЫХ ЗАБОЛЕВАНИЙ |
| US8952071B2 (en) * | 2008-01-08 | 2015-02-10 | Edison Pharmaceuticals, Inc. | (Het)aryl-p-quinone derivatives for treatment of mitochondrial diseases |
| WO2009111576A2 (en) | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| JP5798481B2 (ja) * | 2008-06-25 | 2015-10-21 | 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 | 酸化ストレス疾患を治療するための２−ヘテロシクリルアミノアルキル−（ｐ−キノン）誘導体 |
| MX363223B (es) | 2008-09-10 | 2019-03-15 | Bioelectron Tech Corp | Tratamiento de trastornos generalizados del desarrollo con terapeuticos con actividad redox. |
| 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 |
| ES2553557T3 (es) | 2008-10-28 | 2015-12-10 | Edison Pharmaceuticals, Inc. | Proceso para la producción de alfa-tocotrienol y derivados |
| CA2777479C (en) | 2009-04-28 | 2017-10-17 | Ptc Therapeutics, Inc. | Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones |
| NO2470168T3 (https=) * | 2009-08-26 | 2018-06-30 | ||
| US20110172312A1 (en) * | 2009-12-31 | 2011-07-14 | Miller Guy M | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| EP2642991A1 (en) | 2010-11-22 | 2013-10-02 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Therapeutical method for the treatment of the leber optic |
| WO2012174286A1 (en) * | 2011-06-14 | 2012-12-20 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| ES2795798T3 (es) * | 2011-07-06 | 2020-11-24 | Ptc Therapeutics Inc | Tratamiento de aciduria metilmalónica, aciduria isovalérica, y otras acidurias orgánicas con tocotrienol quinonas |
| EP2734512B1 (en) | 2011-07-19 | 2019-11-20 | Bioelectron Technology Corporation | Methods for selective oxidation of alpha tocotrienol in the presence of non-alpha tocotrienols |
| JP6238977B2 (ja) | 2012-06-29 | 2017-11-29 | ラオフ・レキク | 視神経症または先天性視神経萎縮を治療するためのアンギオテンシン変換酵素阻害薬 |
| CA2883882A1 (en) | 2012-09-07 | 2014-03-13 | Ptc Therapeutics, Inc. | Benzoquinone derivatives for treating oxidative stress disorders |
| 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 |
| WO2015103577A1 (en) * | 2014-01-06 | 2015-07-09 | Stealth Peptides International, Inc. | Methods and compositions for preventing or treating dominant optic atrophy |
| DK3233786T3 (da) | 2014-12-16 | 2022-05-09 | Ptc Therapeutics Inc | Polymorfe og amorfe former af (r)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6- dioxocyclohexa-1,4-dienyl)butanamid |
| US11337980B2 (en) | 2015-06-05 | 2022-05-24 | Fundació Hospital Universitari Vall D'hebron-Institut De Recerca | Treatment of mitochondrial diseases |
| WO2017106786A1 (en) | 2015-12-16 | 2017-06-22 | Bioelectron Technology Corporation | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| US10703701B2 (en) | 2015-12-17 | 2020-07-07 | Ptc Therapeutics, Inc. | Fluoroalkyl, fluoroalkoxy, 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 |
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-
2010
- 2010-04-27 CA CA2777479A patent/CA2777479C/en not_active Expired - Fee Related
- 2010-04-27 JP JP2012508609A patent/JP2012525399A/ja not_active Withdrawn
- 2010-04-27 ES ES10715650.7T patent/ES2662051T3/es active Active
- 2010-04-27 MX MX2011011309A patent/MX336800B/es active IP Right Grant
- 2010-04-27 PL PL10715650T patent/PL2424495T3/pl unknown
- 2010-04-27 DK DK10715650.7T patent/DK2424495T3/en active
- 2010-04-27 NO NO10715650A patent/NO2424495T3/no unknown
- 2010-04-27 PT PT107156507T patent/PT2424495T/pt unknown
- 2010-04-27 SI SI201031630T patent/SI2424495T1/en unknown
- 2010-04-27 US US12/768,565 patent/US20100273894A1/en not_active Abandoned
- 2010-04-27 EP EP18151731.9A patent/EP3332766A1/en not_active Withdrawn
- 2010-04-27 WO PCT/US2010/032624 patent/WO2010126911A1/en not_active Ceased
- 2010-04-27 HU HUE10715650A patent/HUE037574T2/hu unknown
- 2010-04-27 EP EP10715650.7A patent/EP2424495B1/en not_active Not-in-force
- 2010-04-27 EA EA201101575A patent/EA031126B1/ru not_active IP Right Cessation
- 2010-04-27 BR BRPI1013376A patent/BRPI1013376A8/pt not_active Application Discontinuation
-
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
-
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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