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.)
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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 (enExample) | 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 (enExample) |
| EP (1) | EP2262519A4 (enExample) |
| JP (4) | JP2011513420A (enExample) |
| CA (1) | CA2717741C (enExample) |
| WO (1) | WO2009111543A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005033092A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | Chroman derivatives |
| EA035619B1 (ru) * | 2005-06-01 | 2020-07-16 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Композиции для использования в способе лечения митохондриальных нарушений |
| 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 |
| PL2220030T3 (pl) | 2007-11-06 | 2016-07-29 | Bioelectron Tech Corp | Pochodne 4-(p-chinonylo)-2-hydroksybutanamidu do leczenia chorób mitochondrialnych |
| EP2237664A4 (en) | 2008-01-08 | 2013-05-22 | Edison Pharmaceuticals Inc | (HET) ARYL-p-CHINONE DERIVATIVES FOR THE TREATMENT OF OCHONDRIAL DISEASES |
| WO2009111576A2 (en) | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| EP2303824B1 (en) * | 2008-06-25 | 2015-03-25 | 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 |
| 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 |
| WO2010051277A1 (en) * | 2008-10-28 | 2010-05-06 | Edison Pharmaceuticals, Inc. | Process for the production of alpha-tocotrienol and derivatives |
| 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 (enExample) * | 2009-08-26 | 2018-06-30 | ||
| CA2797644A1 (en) * | 2009-12-31 | 2011-07-07 | Edison Pharmaceuticals, Inc. | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| EA201201374A1 (ru) * | 2010-04-06 | 2013-04-30 | Эдисон Фармасьютикалз, Инк. | Лечение атаксии-телеангиэктазии |
| US9464016B2 (en) | 2011-06-14 | 2016-10-11 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| CA2842486C (en) | 2011-07-19 | 2022-09-06 | Edison Pharmaceuticals, Inc. | Methods for oxidation of alpha tocotrienol in the presence of non-alpha tocotrienols |
| 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 |
| JP2016515526A (ja) | 2013-03-15 | 2016-05-30 | 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 | 酸化ストレス障害の処置のためのアルキル−ヘテロアリール置換されたキノン誘導体 |
| 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 |
| EP2982382A1 (en) | 2014-08-04 | 2016-02-10 | Sensorion | Compounds for preventing ototoxicity |
| HUE058877T2 (hu) * | 2014-12-16 | 2022-09-28 | Ptc Therapeutics Inc | (R)-2-hidroxi-2-metil-4-(2,4,5-trimetil-3,6-dioxociklohexa-1,4-dienil)butánamid polimorf és amorf alakjai |
| US10388137B2 (en) | 2015-04-16 | 2019-08-20 | Honeywell International Inc. | Multi-sensor input analysis for improved safety |
| ES3033538T3 (en) * | 2015-10-08 | 2025-08-05 | Khondrion Ip B V | Novel compounds for treating mitochondrial disease |
| JP7117241B2 (ja) | 2015-12-16 | 2022-08-12 | ピーティーシー セラピューティクス， インコーポレイテッド | 混合されたトコール組成物からアルファ－トコトリエノールを富化するための改良された方法 |
| EP3389646A1 (en) | 2015-12-17 | 2018-10-24 | BioElectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| KR101785455B1 (ko) * | 2016-03-16 | 2017-11-20 | 전남대학교산학협력단 | 귀리 추출물을 유효성분으로 포함하는 난청의 예방 또는 치료용 약제학적 조성물 |
| 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 |
| HUE066196T2 (hu) | 2018-10-17 | 2024-07-28 | Ptc Therapeutics Inc | 2,3,5-trimetil-6-nonilciklohexa-2,5-dién-1,4-dion alfa-szinukleinopátiák, tauopátiák és egyéb rendellenességek szuppresszálására és kezelésére |
| KR102177610B1 (ko) * | 2019-03-28 | 2020-11-11 | 단국대학교 천안캠퍼스 산학협력단 | 청각세포와의 공배양을 이용한 배아줄기세포의 내이 세포로의 분화 방법 |
| JP7531808B2 (ja) * | 2020-11-04 | 2024-08-13 | 国立大学法人 東京大学 | 騒音性難聴の予防剤 |
| EP4366700A1 (en) | 2021-07-08 | 2024-05-15 | PTC Therapeutics, Inc. | Pharmaceutical compositions comprising 2,3,5-trimethyl-6-nonylcyclohexa-2,5-diene-1,4-dione |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1040908A (en) | 1910-09-06 | 1912-10-08 | George E Dunton | Composition of matter for use in removing grease, &c., from the molds used in the art of electrotyping. |
| US1038708A (en) | 1911-11-01 | 1912-09-17 | Hipolit Zielinski | Wrench. |
| JPS5938203B2 (ja) * | 1976-04-26 | 1984-09-14 | エーザイ株式会社 | 補酵素ｑを主成分とする脳循環障害治療剤 |
| US4637402A (en) | 1980-04-28 | 1987-01-20 | Adelman Roger A | Method for quantitatively measuring a hearing defect |
| US5059591B1 (en) | 1983-05-26 | 2000-04-25 | Liposome Co Inc | Drug preparations of reduced toxicity |
| US5546956A (en) | 1992-04-04 | 1996-08-20 | Medical Research Council | Testing hearing |
| WO1993024650A1 (en) * | 1992-05-28 | 1993-12-09 | Monash University | Therapeutic compositions |
| US5421818A (en) | 1993-10-18 | 1995-06-06 | Inner Ear Medical Delivery Systems, Inc. | Multi-functional inner ear treatment and diagnostic system |
| DE4402380A1 (de) | 1994-01-27 | 1995-08-03 | Hans Peter Prof Dr Med Zenner | Implantierbares Dosiersystem |
| EP1398026B1 (de) * | 1997-02-12 | 2006-06-21 | MSE Pharmazeutika GmbH | Verwendung von 2,3-Dimethoxy-5-methyl-6-decaprenyl-1,4-benzochinon in der Behandlung von Inkontinenz |
| WO1998035658A2 (de) * | 1997-02-12 | 1998-08-20 | Mse Pharmazeutika Gmbh | Verwendung von 2,3-dimethoxy-5-methyl-6-decaprenyl-1,4-benzochinon |
| FR2783519B1 (fr) * | 1998-09-23 | 2003-01-24 | Sod Conseils Rech Applic | Nouveaux derives d'amidines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
| US6120484A (en) | 1999-02-17 | 2000-09-19 | Silverstein; Herbert | Otological implant for delivery of medicament and method of using same |
| US7220784B2 (en) * | 2000-12-21 | 2007-05-22 | John Anthony Hadfield | Substituted stilbenes and their reactions |
| US7700134B2 (en) * | 2002-01-17 | 2010-04-20 | The Regents Of The University Of Michigan | Prevention of cisplatin induced deafness |
| US20030229333A1 (en) | 2002-02-22 | 2003-12-11 | Control Delivery Systems, Inc. | Methods for treating otic disorders |
| EP1454627A1 (en) * | 2003-03-06 | 2004-09-08 | MyoContract Ltd. | Alpha-Keto carbonyl calpain inhibitors |
| US20040204471A1 (en) * | 2003-03-20 | 2004-10-14 | Pharmacia Corporation | Treatment and prevention of otic disorders with Cox-2 inhibitors alone or in combination with otic agents |
| JP2008503579A (ja) * | 2004-06-21 | 2008-02-07 | ハッチソン メディファーマ エンタープライジズ リミテッド | 癌の化学療法 |
| EA035619B1 (ru) * | 2005-06-01 | 2020-07-16 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Композиции для использования в способе лечения митохондриальных нарушений |
| US20070021497A1 (en) * | 2005-07-11 | 2007-01-25 | The Fruitful Yield | Vitamin e compositions |
| JP2009508867A (ja) * | 2005-09-15 | 2009-03-05 | 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関連した様態の治療ならびにエネルギーバイオマーカーの調節のための酸化還元活性治療剤のテイル改変体 |
| 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 |
| US7786100B2 (en) * | 2006-03-20 | 2010-08-31 | The Regents Of The University Of Michigan | Composition and method of treating hearing loss |
| PL2220030T3 (pl) * | 2007-11-06 | 2016-07-29 | Bioelectron Tech Corp | Pochodne 4-(p-chinonylo)-2-hydroksybutanamidu do leczenia chorób mitochondrialnych |
| EP2237664A4 (en) * | 2008-01-08 | 2013-05-22 | Edison Pharmaceuticals Inc | (HET) ARYL-p-CHINONE DERIVATIVES FOR THE TREATMENT OF OCHONDRIAL DISEASES |
| WO2009111576A2 (en) * | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
-
2009
- 2009-03-04 EP EP09718285A patent/EP2262519A4/en not_active Withdrawn
- 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 WO PCT/US2009/035996 patent/WO2009111543A2/en not_active Ceased
-
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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