JP2011513420A5 - - Google Patents
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- JP2011513420A5 JP2011513420A5 JP2010549844A JP2010549844A JP2011513420A5 JP 2011513420 A5 JP2011513420 A5 JP 2011513420A5 JP 2010549844 A JP2010549844 A JP 2010549844A JP 2010549844 A JP2010549844 A JP 2010549844A JP 2011513420 A5 JP2011513420 A5 JP 2011513420A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- haloalkyl
- formula
- hydroxy
- 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- Withdrawn
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- 239000000203 mixture Substances 0.000 claims description 64
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 46
- 239000003814 drug Substances 0.000 claims description 45
- 229940124597 therapeutic agent Drugs 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 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 24
- 230000004064 dysfunction Effects 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 230000001225 therapeutic effect Effects 0.000 claims description 18
- 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 16
- 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 16
- 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 16
- 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 16
- 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 16
- 239000011723 β-tocotrienol Substances 0.000 claims description 16
- 235000019151 β-tocotrienol Nutrition 0.000 claims description 16
- 239000011722 γ-tocotrienol Substances 0.000 claims description 16
- 235000019150 γ-tocotrienol Nutrition 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 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 15
- 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 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 231100000199 ototoxic Toxicity 0.000 claims description 12
- 230000002970 ototoxic effect Effects 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 229940064063 alpha tocotrienol Drugs 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- LZBJQFBCLCRSIF-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-3-[4-(trifluoromethyl)phenyl]cyclohexa-2,5-diene-1,4-dione Chemical group O=C1C(C)=C(C)C(=O)C(C=2C=CC(=CC=2)C(F)(F)F)=C1CCC(C)(C)O LZBJQFBCLCRSIF-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 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 8
- 239000011730 α-tocotrienol Substances 0.000 claims description 8
- 235000019145 α-tocotrienol Nutrition 0.000 claims description 8
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 claims description 8
- -1 N, N′-disubstituted piperazine Chemical class 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- LOWAFOSZWAXVPN-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-3,5-dimethyl-6-[4-(trifluoromethyl)phenyl]cyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(CCC(C)(C)O)C(=O)C(C=2C=CC(=CC=2)C(F)(F)F)=C1C LOWAFOSZWAXVPN-UHFFFAOYSA-N 0.000 claims description 4
- LTVDFSLWFKLJDQ-IEOSBIPESA-N 2-[(3r,7r,11r)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@](C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-IEOSBIPESA-N 0.000 claims description 4
- HHCFBRMRTMTSHY-UHFFFAOYSA-N 2-[3-hydroxy-4-(4-hydroxypiperidin-1-yl)-3-methyl-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical group O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCC(O)CC2)=C1C HHCFBRMRTMTSHY-UHFFFAOYSA-N 0.000 claims description 4
- WMKSYSBVGRPFNM-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)-3-hydroxy-3-methyl-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound C1CN(C(=O)C)CCN1C(=O)C(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O WMKSYSBVGRPFNM-UHFFFAOYSA-N 0.000 claims description 4
- BAANPNDZFYBQIB-UHFFFAOYSA-N 2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound CC1=C(C)C(=O)C(CCC(C)(O)C(N)=O)=C(C)C1=O BAANPNDZFYBQIB-UHFFFAOYSA-N 0.000 claims description 4
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 4
- LTVDFSLWFKLJDQ-DKGMKSHISA-N alpha-Tocopherolquinone Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-DKGMKSHISA-N 0.000 claims description 4
- 229940066595 beta tocopherol Drugs 0.000 claims description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
- 229960004316 cisplatin Drugs 0.000 claims description 4
- 235000010382 gamma-tocopherol Nutrition 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- GNUWFWUNTMBWKG-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound CN(C)CCNC(=O)C(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O GNUWFWUNTMBWKG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000004151 quinonyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 239000011590 β-tocopherol Substances 0.000 claims description 4
- 235000007680 β-tocopherol Nutrition 0.000 claims description 4
- 239000002478 γ-tocopherol Substances 0.000 claims description 4
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 claims description 4
- 229940034982 antineoplastic agent Drugs 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 208000016354 hearing loss disease Diseases 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 2
- 206010011878 Deafness Diseases 0.000 claims description 2
- 206010011903 Deafness traumatic Diseases 0.000 claims description 2
- 208000002946 Noise-Induced Hearing Loss Diseases 0.000 claims description 2
- 208000009205 Tinnitus Diseases 0.000 claims description 2
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 229940030606 diuretics Drugs 0.000 claims description 2
- 230000010370 hearing loss Effects 0.000 claims description 2
- 231100000888 hearing loss Toxicity 0.000 claims description 2
- 229960004135 idebenone Drugs 0.000 claims description 2
- JGPMMRGNQUBGND-UHFFFAOYSA-N idebenone Chemical group COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O JGPMMRGNQUBGND-UHFFFAOYSA-N 0.000 claims description 2
- 230000003961 neuronal insult Effects 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 229960000948 quinine Drugs 0.000 claims description 2
- 150000003873 salicylate salts Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 231100000886 tinnitus Toxicity 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 125000000255 β-tocotrienol group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 29
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 0 CC(CCCC*)CCC(C(C(C1=C*1)=C1)=O)=C(*)C1=O Chemical compound CC(CCCC*)CCC(C(C(C1=C*1)=C1)=O)=C(*)C1=O 0.000 description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6833008P | 2008-03-05 | 2008-03-05 | |
| US19119808P | 2008-09-05 | 2008-09-05 | |
| PCT/US2009/035996 WO2009111543A2 (en) | 2008-03-05 | 2009-03-04 | Treatment of hearing and balance impairments with redox-active therapeutics |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014016459A Division JP6131200B2 (ja) | 2008-03-05 | 2014-01-31 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011513420A JP2011513420A (ja) | 2011-04-28 |
| JP2011513420A5 true JP2011513420A5 (OSRAM) | 2013-04-04 |
Family
ID=41056624
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010549844A Withdrawn JP2011513420A (ja) | 2008-03-05 | 2009-03-04 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
| JP2014016459A Active JP6131200B2 (ja) | 2008-03-05 | 2014-01-31 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
| JP2015160272A Withdrawn JP2015205938A (ja) | 2008-03-05 | 2015-08-17 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
| JP2017151442A Pending JP2017193590A (ja) | 2008-03-05 | 2017-08-04 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014016459A Active JP6131200B2 (ja) | 2008-03-05 | 2014-01-31 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
| JP2015160272A Withdrawn JP2015205938A (ja) | 2008-03-05 | 2015-08-17 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
| JP2017151442A Pending JP2017193590A (ja) | 2008-03-05 | 2017-08-04 | レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置 |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US20110046156A1 (OSRAM) |
| EP (1) | EP2262519A4 (OSRAM) |
| JP (4) | JP2011513420A (OSRAM) |
| CA (1) | CA2717741C (OSRAM) |
| WO (1) | WO2009111543A2 (OSRAM) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2583087C (en) | 2003-09-19 | 2012-07-10 | Galileo Pharmaceuticals, Inc. | Chroman derivatives |
| WO2006130775A2 (en) * | 2005-06-01 | 2006-12-07 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomakers |
| JP5374162B2 (ja) | 2006-02-22 | 2013-12-25 | 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 | 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 |
| EP3456707B1 (en) | 2007-11-06 | 2020-04-15 | PTC Therapeutics, 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 |
| CA2717734A1 (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 |
| EP3827815B1 (en) | 2008-09-10 | 2023-09-06 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| WO2010045220A1 (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 |
| TR201819154T4 (tr) * | 2008-10-28 | 2019-01-21 | Bioelectron Tech Corp | Alfa-tokotrienol kuinone ve ara ürünlerini içeren bileşim. |
| WO2010126911A1 (en) | 2009-04-28 | 2010-11-04 | Edison Pharmaceuticals, Inc. | Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones |
| CA2772294C (en) * | 2009-08-26 | 2018-08-21 | Guy M. Miller | Methods for the prevention and treatment of cerebral ischemia |
| EP2519232A1 (en) * | 2009-12-31 | 2012-11-07 | Edison Pharmaceuticals, Inc. | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| JP2013523816A (ja) * | 2010-04-06 | 2013-06-17 | 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 | 毛細血管拡張性運動失調症の治療 |
| US9464016B2 (en) | 2011-06-14 | 2016-10-11 | 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 |
| CA2883882A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Benzoquinone derivatives for treating oxidative stress disorders |
| EP2970158B1 (en) | 2013-03-15 | 2019-02-20 | 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 |
| 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 |
| EP2982382A1 (en) | 2014-08-04 | 2016-02-10 | Sensorion | Compounds for preventing ototoxicity |
| EP3233786B1 (en) | 2014-12-16 | 2022-03-16 | 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 |
| CN107690664B (zh) | 2015-04-16 | 2023-04-04 | 霍尼韦尔国际公司 | 用于改进的安全性的多传感器输入分析 |
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-
2009
- 2009-03-04 WO PCT/US2009/035996 patent/WO2009111543A2/en not_active Ceased
- 2009-03-04 JP JP2010549844A patent/JP2011513420A/ja not_active Withdrawn
- 2009-03-04 US US12/919,004 patent/US20110046156A1/en not_active Abandoned
- 2009-03-04 CA CA2717741A patent/CA2717741C/en not_active Expired - Fee Related
- 2009-03-04 EP EP09718285A patent/EP2262519A4/en not_active Withdrawn
-
2014
- 2014-01-31 JP JP2014016459A patent/JP6131200B2/ja active Active
- 2014-02-06 US US14/174,753 patent/US20140249160A1/en not_active Abandoned
-
2015
- 2015-08-17 JP JP2015160272A patent/JP2015205938A/ja not_active Withdrawn
-
2017
- 2017-08-04 JP JP2017151442A patent/JP2017193590A/ja active Pending
- 2017-12-20 US US15/849,550 patent/US20180200248A1/en not_active Abandoned
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