CA2717741C - Treatment of hearing and balance impairments with redox-active therapeutics - Google Patents
Treatment of hearing and balance impairments with redox-active therapeutics Download PDFInfo
- Publication number
- CA2717741C CA2717741C CA2717741A CA2717741A CA2717741C CA 2717741 C CA2717741 C CA 2717741C CA 2717741 A CA2717741 A CA 2717741A CA 2717741 A CA2717741 A CA 2717741A CA 2717741 C CA2717741 C CA 2717741C
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- Prior art keywords
- alkyl
- hydroxy
- methyl
- composition
- redox
- Prior art date
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- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 claims abstract description 412
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 272
- 230000002970 ototoxic effect Effects 0.000 claims abstract description 50
- 231100000199 ototoxic Toxicity 0.000 claims abstract description 48
- 241000124008 Mammalia Species 0.000 claims abstract description 10
- 230000003961 neuronal insult Effects 0.000 claims abstract description 8
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- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 145
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 87
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 77
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 68
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- 125000003118 aryl group Chemical group 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 60
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 40
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
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- 229910052736 halogen Inorganic materials 0.000 claims description 37
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- 229910052740 iodine Inorganic materials 0.000 claims description 30
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
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- 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 22
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- 235000019150 γ-tocotrienol Nutrition 0.000 claims description 22
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 20
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- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 17
- 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 16
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims description 16
- 230000006870 function Effects 0.000 claims description 16
- 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 16
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- 125000001424 substituent group Chemical group 0.000 claims description 15
- 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 14
- 229940064063 alpha tocotrienol Drugs 0.000 claims description 14
- 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 14
- 239000000126 substance Substances 0.000 claims description 14
- 230000003405 preventing effect Effects 0.000 claims description 13
- 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 13
- 239000011730 α-tocotrienol Substances 0.000 claims description 13
- 235000019145 α-tocotrienol Nutrition 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 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 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 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 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004151 quinonyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 206010011903 Deafness traumatic Diseases 0.000 claims description 10
- 208000002946 Noise-Induced Hearing Loss Diseases 0.000 claims description 10
- 229940034982 antineoplastic agent Drugs 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 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 8
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- 235000010382 gamma-tocopherol Nutrition 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- 239000011590 β-tocopherol Substances 0.000 claims description 8
- 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 8
- 239000002478 γ-tocopherol Substances 0.000 claims description 8
- 208000009205 Tinnitus Diseases 0.000 claims description 7
- 229960004135 idebenone Drugs 0.000 claims description 7
- JGPMMRGNQUBGND-UHFFFAOYSA-N idebenone Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O JGPMMRGNQUBGND-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 231100000886 tinnitus Toxicity 0.000 claims description 7
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 6
- 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 6
- 229930003427 Vitamin E Natural products 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 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 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- QIXDHVDGPXBRRD-UHFFFAOYSA-N 2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 claims description 4
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 27
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- LZBJQFBCLCRSIF-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-3-[4-(trifluoromethyl)phenyl]cyclohexa-2,5-diene-1,4-dione Chemical compound 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 9
- 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 9
- BXRSDZYHNKBTCJ-UHFFFAOYSA-N 2-hydroxy-n-(3-imidazol-1-ylpropyl)-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCCCN2C=NC=C2)=C1C BXRSDZYHNKBTCJ-UHFFFAOYSA-N 0.000 claims 9
- FWJVBYKJYRZAGV-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound CN(C)CCCNC(=O)C(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O FWJVBYKJYRZAGV-UHFFFAOYSA-N 0.000 claims 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 8
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 8
- QVIPRTNEYGUELS-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2C=CC(Cl)=CC=2)=C1CCC(C)(C)O QVIPRTNEYGUELS-UHFFFAOYSA-N 0.000 claims 8
- SFNNDQVZSABNTF-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(3-hydroxy-3-methylbutyl)-3,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(CCC(C)(C)O)C(=O)C(C=2C=CC(Cl)=CC=2)=C1C SFNNDQVZSABNTF-UHFFFAOYSA-N 0.000 claims 8
- YQWBZLQPLUEHID-UHFFFAOYSA-N 2-[3-hydroxy-3-methyl-4-(4-methylpiperazin-1-yl)-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound C1CN(C)CCN1C(=O)C(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O YQWBZLQPLUEHID-UHFFFAOYSA-N 0.000 claims 8
- 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 compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCC(O)CC2)=C1C HHCFBRMRTMTSHY-UHFFFAOYSA-N 0.000 claims 8
- 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 8
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 7
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 4
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- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- FJQDVUOFSWABTE-UHFFFAOYSA-N 2,3,5-trimethyl-6-(3-methylnon-2-enyl)cyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCC(C)=CCC1=C(C)C(=O)C(C)=C(C)C1=O FJQDVUOFSWABTE-UHFFFAOYSA-N 0.000 claims 3
- ZJFCPSCICSOWQP-UHFFFAOYSA-N 2,3-dimethyl-5,6-bis(3-methylbutyl)cyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)CCC1=C(CCC(C)C)C(=O)C(C)=C(C)C1=O ZJFCPSCICSOWQP-UHFFFAOYSA-N 0.000 claims 3
- JEAWXYCNVHEFAV-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2OC3=CC=CC=C3C=2)=C1CCC(C)(C)O JEAWXYCNVHEFAV-UHFFFAOYSA-N 0.000 claims 3
- MPAODSFYZAQWFP-UHFFFAOYSA-N 2-(3-chloro-15-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(O)(C)CCCC(C)CCCC(C)CCCC(C)(Cl)CCC1=C(C)C(=O)C(C)=C(C)C1=O MPAODSFYZAQWFP-UHFFFAOYSA-N 0.000 claims 3
- FRFMRBMRVXWHSC-UHFFFAOYSA-N 2-(3-hydroxy-3-methyl-4-oxo-4-piperazin-1-ylbutyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCNCC2)=C1C FRFMRBMRVXWHSC-UHFFFAOYSA-N 0.000 claims 3
- IAFSJZOBPHUUAJ-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-3-(4-methoxyphenyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(OC)=CC=C1C1=C(CCC(C)(C)O)C(=O)C(C)=C(C)C1=O IAFSJZOBPHUUAJ-UHFFFAOYSA-N 0.000 claims 3
- NOIGJVXSHVUSLY-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-3-(2-phenylethyl)cyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(C)O)=C1CCC1=CC=CC=C1 NOIGJVXSHVUSLY-UHFFFAOYSA-N 0.000 claims 3
- JLONLOLEKLDJSC-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-3-(3-methylbut-2-enyl)cyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)=CCC1=C(CCC(C)(C)O)C(=O)C(C)=C(C)C1=O JLONLOLEKLDJSC-UHFFFAOYSA-N 0.000 claims 3
- RMPBGNMYHDNLMV-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-3-(3-phenylpropyl)cyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(C)O)=C1CCCC1=CC=CC=C1 RMPBGNMYHDNLMV-UHFFFAOYSA-N 0.000 claims 3
- PSAVQCQBOXFMJH-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-3-[3-(trifluoromethyl)phenyl]cyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2C=C(C=CC=2)C(F)(F)F)=C1CCC(C)(C)O PSAVQCQBOXFMJH-UHFFFAOYSA-N 0.000 claims 3
- MFUIECZNXBDUON-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-5,6-dimethyl-3-naphthalen-2-ylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2C=C3C=CC=CC3=CC=2)=C1CCC(C)(C)O MFUIECZNXBDUON-UHFFFAOYSA-N 0.000 claims 3
- JHQIXMCFXKLVLD-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutyl)-6-(4-methoxyphenyl)-3,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(OC)=CC=C1C1=C(C)C(=O)C(C)=C(CCC(C)(C)O)C1=O JHQIXMCFXKLVLD-UHFFFAOYSA-N 0.000 claims 3
- JXVUFWRGFVHAJA-UHFFFAOYSA-N 2-(4-ethylphenyl)-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound C1=CC(CC)=CC=C1C1=C(CCC(C)(C)O)C(=O)C(C)=C(C)C1=O JXVUFWRGFVHAJA-UHFFFAOYSA-N 0.000 claims 3
- PFCMMFVHMXNJOT-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2C=CC(F)=CC=2)=C1CCC(C)(C)O PFCMMFVHMXNJOT-UHFFFAOYSA-N 0.000 claims 3
- IUDXSCGIQPHNGU-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-(3-hydroxy-3-methylbutyl)-3,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(CCC(C)(C)O)C(=O)C(C=2C=CC(F)=CC=2)=C1C IUDXSCGIQPHNGU-UHFFFAOYSA-N 0.000 claims 3
- RWGCFWBUCIJFOF-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2C=CC(=CC=2)C(C)(C)C)=C1CCC(C)(C)O RWGCFWBUCIJFOF-UHFFFAOYSA-N 0.000 claims 3
- CSLDAUWGMJKZBW-UHFFFAOYSA-N 2-(6-chloro-3-methylhex-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound ClCCCC(C)=CCC1=C(C)C(=O)C(C)=C(C)C1=O CSLDAUWGMJKZBW-UHFFFAOYSA-N 0.000 claims 3
- ZZSLCHDPUBHPEN-UHFFFAOYSA-N 2-(6-iodo-3-methylhex-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound ICCCC(C)=CCC1=C(C)C(=O)C(C)=C(C)C1=O ZZSLCHDPUBHPEN-UHFFFAOYSA-N 0.000 claims 3
- WSFVCVLKAWXEOT-UHFFFAOYSA-N 2-(7-chloro-3-methylhept-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound ClCCCCC(C)=CCC1=C(C)C(=O)C(C)=C(C)C1=O WSFVCVLKAWXEOT-UHFFFAOYSA-N 0.000 claims 3
- WHTAEUOQSUPCAE-UHFFFAOYSA-N 2-(7-hydroxy-3-methylhept-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound OCCCCC(C)=CCC1=C(C)C(=O)C(C)=C(C)C1=O WHTAEUOQSUPCAE-UHFFFAOYSA-N 0.000 claims 3
- ZVUWULZKPPTQIJ-UHFFFAOYSA-N 2-[4-(4-benzoylpiperazin-1-yl)-3-hydroxy-3-methyl-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCN(CC2)C(=O)C=2C=CC=CC=2)=C1C ZVUWULZKPPTQIJ-UHFFFAOYSA-N 0.000 claims 3
- NZTUDHWGKIMDSD-UHFFFAOYSA-N 2-[4-(4-benzylpiperazin-1-yl)-3-hydroxy-3-methyl-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCN(CC=3C=CC=CC=3)CC2)=C1C NZTUDHWGKIMDSD-UHFFFAOYSA-N 0.000 claims 3
- VDQYQSWPEIJUKH-UHFFFAOYSA-N 2-[4-(4-fluoropiperidin-1-yl)-3-hydroxy-3-methyl-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCC(F)CC2)=C1C VDQYQSWPEIJUKH-UHFFFAOYSA-N 0.000 claims 3
- ULGYWTCJJIMCGB-UHFFFAOYSA-N 2-benzyl-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CC=2C=CC=CC=2)=C1CCC(C)(C)O ULGYWTCJJIMCGB-UHFFFAOYSA-N 0.000 claims 3
- AWDQBDGPVYTAEH-UHFFFAOYSA-N 2-heptadec-8-enyl-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCC=CCCCCCCCC1=C(C)C(=O)C(C)=C(C)C1=O AWDQBDGPVYTAEH-UHFFFAOYSA-N 0.000 claims 3
- KEXIPVHYDKTMQY-UHFFFAOYSA-N 2-heptadeca-8,11-dienyl-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCC=CCC=CCCCCCCCC1=C(C)C(=O)C(C)=C(C)C1=O KEXIPVHYDKTMQY-UHFFFAOYSA-N 0.000 claims 3
- HCIBENMRSHGAGP-UHFFFAOYSA-N 2-heptadeca-8,11-dienyl-6-methyl-3,5-di(propan-2-yl)cyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCC=CCC=CCCCCCCCC1=C(C(C)C)C(=O)C(C(C)C)=C(C)C1=O HCIBENMRSHGAGP-UHFFFAOYSA-N 0.000 claims 3
- GVEZIVXAVIQWDD-UHFFFAOYSA-N 2-heptyl-6-methyl-3,5-di(propan-2-yl)cyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCC1=C(C(C)C)C(=O)C(C(C)C)=C(C)C1=O GVEZIVXAVIQWDD-UHFFFAOYSA-N 0.000 claims 3
- WCMYLQAULKZTFA-UHFFFAOYSA-N 2-hexyl-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCC1=C(C)C(=O)C(C)=C(C)C1=O WCMYLQAULKZTFA-UHFFFAOYSA-N 0.000 claims 3
- WPNCZUXRTXNUOT-UHFFFAOYSA-N 2-hydroxy-2-methyl-n-(3-morpholin-4-ylpropyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCCCN2CCOCC2)=C1C WPNCZUXRTXNUOT-UHFFFAOYSA-N 0.000 claims 3
- WPGQBIUQNUJYCQ-UHFFFAOYSA-N 2-hydroxy-2-methyl-n-(pyridin-2-ylmethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCC=2N=CC=CC=2)=C1C WPGQBIUQNUJYCQ-UHFFFAOYSA-N 0.000 claims 3
- BUGSNVNVEDKWKS-UHFFFAOYSA-N 2-hydroxy-n,n-bis(2-hydroxyethyl)-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(=O)N(CCO)CCO)=C(C)C1=O BUGSNVNVEDKWKS-UHFFFAOYSA-N 0.000 claims 3
- HNDAUTXEFVPLLV-UHFFFAOYSA-N 2-hydroxy-n-(1-hydroxypropan-2-yl)-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound OCC(C)NC(=O)C(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O HNDAUTXEFVPLLV-UHFFFAOYSA-N 0.000 claims 3
- JJRHJDUELSYTPF-UHFFFAOYSA-N 2-hydroxy-n-(2-hydroxyethyl)-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(=O)NCCO)=C(C)C1=O JJRHJDUELSYTPF-UHFFFAOYSA-N 0.000 claims 3
- NXMYNEGBZPZYEA-UHFFFAOYSA-N 2-hydroxy-n-(4-methoxyphenyl)-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O NXMYNEGBZPZYEA-UHFFFAOYSA-N 0.000 claims 3
- BRGNSBSIUIKKLP-UHFFFAOYSA-N 2-hydroxy-n-(5-hydroxypentyl)-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(=O)NCCCCCO)=C(C)C1=O BRGNSBSIUIKKLP-UHFFFAOYSA-N 0.000 claims 3
- LDKUKIDKPWSTMD-UHFFFAOYSA-N 2-hydroxy-n-(6-hydroxyhexyl)-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(=O)NCCCCCCO)=C(C)C1=O LDKUKIDKPWSTMD-UHFFFAOYSA-N 0.000 claims 3
- DCGQEWREDCYBSF-UHFFFAOYSA-N 2-hydroxy-n-[2-(2-hydroxyethoxy)ethyl]-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(=O)NCCOCCO)=C(C)C1=O DCGQEWREDCYBSF-UHFFFAOYSA-N 0.000 claims 3
- OQLUSMGVSCTTCH-UHFFFAOYSA-N 2-hydroxy-n-[2-(4-hydroxyphenyl)ethyl]-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCCC=2C=CC(O)=CC=2)=C1C OQLUSMGVSCTTCH-UHFFFAOYSA-N 0.000 claims 3
- WNHDOSYCCBVXSE-UHFFFAOYSA-N 2-tert-butyl-3-hexyl-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCC1=C(C(C)(C)C)C(=O)C(C)=C(C)C1=O WNHDOSYCCBVXSE-UHFFFAOYSA-N 0.000 claims 3
- CTKXDWAMMHGHAM-UHFFFAOYSA-N 2-tert-butyl-5,6-dimethyl-3-(3-methylnon-2-enyl)cyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCC(C)=CCC1=C(C(C)(C)C)C(=O)C(C)=C(C)C1=O CTKXDWAMMHGHAM-UHFFFAOYSA-N 0.000 claims 3
- OWQTXCMOCSSDQW-UHFFFAOYSA-N 5-methyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hept-5-enenitrile Chemical compound N#CCCCC(C)=CCC1=C(C)C(=O)C(C)=C(C)C1=O OWQTXCMOCSSDQW-UHFFFAOYSA-N 0.000 claims 3
- GYZJOOCNMNYKKK-UHFFFAOYSA-N methyl 2-[[2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoyl]amino]acetate Chemical compound COC(=O)CNC(=O)C(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O GYZJOOCNMNYKKK-UHFFFAOYSA-N 0.000 claims 3
- GIIDGFCEFSGWNY-UHFFFAOYSA-N n-(4-fluorophenyl)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NC=2C=CC(F)=CC=2)=C1C GIIDGFCEFSGWNY-UHFFFAOYSA-N 0.000 claims 3
- GRZJNXJCZCOAGZ-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCC2CC2)=C1C GRZJNXJCZCOAGZ-UHFFFAOYSA-N 0.000 claims 3
- QKZHIBPZCVEKFB-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCC=2C(=CC=CC=2)Cl)=C1C QKZHIBPZCVEKFB-UHFFFAOYSA-N 0.000 claims 3
- GFMGXDDVNMJFIZ-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCC=2C(=CC=CC=2)F)=C1C GFMGXDDVNMJFIZ-UHFFFAOYSA-N 0.000 claims 3
- YMPHFBXCNFBPOG-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCC=2C=C(Cl)C=CC=2)=C1C YMPHFBXCNFBPOG-UHFFFAOYSA-N 0.000 claims 3
- DGVXIDYBGYDEIQ-UHFFFAOYSA-N n-[(3-fluorophenyl)methyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCC=2C=C(F)C=CC=2)=C1C DGVXIDYBGYDEIQ-UHFFFAOYSA-N 0.000 claims 3
- BMKCLCWWONHASE-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCCC=2C(=CC=CC=2)Cl)=C1C BMKCLCWWONHASE-UHFFFAOYSA-N 0.000 claims 3
- SZVXSTCDIBNHEG-UHFFFAOYSA-N n-[2-(2-fluorophenyl)ethyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCCC=2C(=CC=CC=2)F)=C1C SZVXSTCDIBNHEG-UHFFFAOYSA-N 0.000 claims 3
- DXVQBHLMNJCQNF-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCCC=2C=CC(F)=CC=2)=C1C DXVQBHLMNJCQNF-UHFFFAOYSA-N 0.000 claims 3
- OBNGFMRSGTXFDM-UHFFFAOYSA-N n-benzyl-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCC=2C=CC=CC=2)=C1C OBNGFMRSGTXFDM-UHFFFAOYSA-N 0.000 claims 3
- ACDTVRFBXMLONS-UHFFFAOYSA-N n-cyclopropyl-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NC2CC2)=C1C ACDTVRFBXMLONS-UHFFFAOYSA-N 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- MIIHLXMZDBRTSM-UHFFFAOYSA-N tert-butyl 4-[2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoyl]piperazine-1-carboxylate Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1C MIIHLXMZDBRTSM-UHFFFAOYSA-N 0.000 claims 3
- QHXAJKMPZGFJRM-UHFFFAOYSA-N 2,3,5-trimethyl-6-octylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCCCCCCC1=C(C)C(=O)C(C)=C(C)C1=O QHXAJKMPZGFJRM-UHFFFAOYSA-N 0.000 claims 2
- KZOAPCGXYGZPFL-UHFFFAOYSA-N 2-(15-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC(O)(C)CCCC(C)CCCC(C)CCCC(C)CCC1=C(C)C(=O)C(C)=C(C)C1=O KZOAPCGXYGZPFL-UHFFFAOYSA-N 0.000 claims 2
- KSEDDPPMVSBWER-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-6-(3-hydroxy-3-methylbutyl)-3,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(CCC(C)(C)O)C(=O)C(C=2C=C(F)C(F)=CC=2)=C1C KSEDDPPMVSBWER-UHFFFAOYSA-N 0.000 claims 2
- AWKZKODRAUUWJR-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2C=C(F)C=CC=2)=C1CCC(C)(C)O AWKZKODRAUUWJR-UHFFFAOYSA-N 0.000 claims 2
- DHYJSHILHSHPHP-UHFFFAOYSA-N 2-(3-hydroxy-3-methyl-4-oxo-4-piperidin-1-ylbutyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCCCC2)=C1C DHYJSHILHSHPHP-UHFFFAOYSA-N 0.000 claims 2
- PKKYIQAXOSTPRF-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-3-(3-hydroxy-3-methylbutyl)-5,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1CCC(C)(C)O PKKYIQAXOSTPRF-UHFFFAOYSA-N 0.000 claims 2
- RUSBHGNKLCOSHQ-UHFFFAOYSA-N 2-[4-(4,4-difluoropiperidin-1-yl)-3-hydroxy-3-methyl-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCC(F)(F)CC2)=C1C RUSBHGNKLCOSHQ-UHFFFAOYSA-N 0.000 claims 2
- IBQDEFFOOZANGJ-UHFFFAOYSA-N 2-[4-(azepan-1-yl)-3-hydroxy-3-methyl-4-oxobutyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)N2CCCCCC2)=C1C IBQDEFFOOZANGJ-UHFFFAOYSA-N 0.000 claims 2
- OBDPZTIURVLZSL-UHFFFAOYSA-N 2-hydroxy-2-methyl-n-(2-phenylethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound O=C1C(C)=C(C)C(=O)C(CCC(C)(O)C(=O)NCCC=2C=CC=CC=2)=C1C OBDPZTIURVLZSL-UHFFFAOYSA-N 0.000 claims 2
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- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
- 210000003273 vestibular nerve Anatomy 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
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- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 229950001272 viomycin Drugs 0.000 description 1
- GXFAIFRPOKBQRV-GHXCTMGLSA-N viomycin Chemical compound N1C(=O)\C(=C\NC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)C[C@@H](N)CCCN)CNC(=O)[C@@H]1[C@@H]1NC(=N)N[C@@H](O)C1 GXFAIFRPOKBQRV-GHXCTMGLSA-N 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- 235000013343 vitamin Nutrition 0.000 description 1
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- 239000011719 vitamin A Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6833008P | 2008-03-05 | 2008-03-05 | |
| US61/068,330 | 2008-03-05 | ||
| US19119808P | 2008-09-05 | 2008-09-05 | |
| US61/191,198 | 2008-09-05 | ||
| PCT/US2009/035996 WO2009111543A2 (en) | 2008-03-05 | 2009-03-04 | Treatment of hearing and balance impairments with redox-active therapeutics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2717741A1 CA2717741A1 (en) | 2009-09-11 |
| CA2717741C true CA2717741C (en) | 2018-04-03 |
Family
ID=41056624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2717741A Expired - Fee Related CA2717741C (en) | 2008-03-05 | 2009-03-04 | Treatment of hearing and balance impairments with redox-active therapeutics |
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) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050065099A1 (en) | 2003-09-19 | 2005-03-24 | Gail Walkinshaw | Treatment of mitochondrial diseases |
| 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 |
| EA019675B1 (ru) | 2006-02-22 | 2014-05-30 | Эдисон Фармасьютикалз, Инк. | Редокс-активные терапевтические средства для лечения митохондриальных заболеваний и модуляции биомаркера коэнзима q |
| SI2220030T1 (sl) | 2007-11-06 | 2016-04-29 | Edison Pharmaceuticals, Inc. | Derivati 4-(p-kuinonil)-2-hidroksibutanamida za zdravljenje mitohondrijskih bolezni |
| WO2009089224A1 (en) * | 2008-01-08 | 2009-07-16 | Edison Pharmaceuticals, Inc. | (HET) ARYL-p-QUINONE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES |
| US8716527B2 (en) | 2008-03-05 | 2014-05-06 | Edison Pharmaceuticals, Inc. | 2-substituted-p-quinone derivatives for treatment of oxidative stress diseases |
| US8716486B2 (en) * | 2008-06-25 | 2014-05-06 | Edison Pharmaceuticals, Inc. | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
| BRPI0918139B1 (pt) | 2008-09-10 | 2024-04-30 | Ptc Therapeutics, Inc | Composição, alimento medicinal ou funcional, suplemento alimentar ou dietético para tratamento de distúrbios de desenvolvimento pervasivos com terapêuticos redox-ativos |
| 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 |
| CA2974482C (en) | 2008-10-28 | 2019-10-29 | Bioelectron Technology Corporation | High purity alpha tocotrienol quinone and processes for preparing same |
| EP2424495B1 (en) | 2009-04-28 | 2018-01-17 | Bioelectron Technology Corporation | Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones |
| PL2470168T3 (pl) * | 2009-08-26 | 2018-06-29 | Bioelectron Technology Corporation | Sposoby zapobiegania i leczenia niedokrwienia mózgu |
| EP2519232A1 (en) * | 2009-12-31 | 2012-11-07 | Edison Pharmaceuticals, Inc. | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| US20130116336A1 (en) * | 2010-04-06 | 2013-05-09 | William D. Shrader | Treatment of ataxia telangiectasia |
| EP2720689A4 (en) | 2011-06-14 | 2014-11-26 | Edison Pharmaceuticals Inc | CATECHOL DERIVATIVES FOR THE TREATMENT OF DISEASES ASSOCIATED WITH OXIDATIVE STRESS |
| 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 |
| CA2883879A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| 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 |
| 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 |
| EP3284055B1 (en) | 2015-04-16 | 2020-08-19 | Honeywell International Inc. | Multi-sensor input analysis for improved safety |
| EP4553065A3 (en) * | 2015-10-08 | 2025-08-27 | Khondrion Ip B.V. | Novel compounds for treating mitochondrial disease |
| 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 |
| 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 |
| CA3116866A1 (en) | 2018-10-17 | 2020-04-23 | Ptc Therapeutics, Inc. | 2,3,5-trimethyl-6-nonylcyclohexa-2,5-diene-1,4-dione for suppressing and treating .alpha.-synucleinopathies, tauopathies, and other disorders |
| 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 |
| CN118175991A (zh) | 2021-07-08 | 2024-06-11 | Ptc医疗公司 | 包含2,3,5-三甲基-6-壬基环己-2,5-二烯-1,4-二酮的药物组合物 |
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| 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 |
| EP0643775B1 (en) * | 1992-05-28 | 2004-07-21 | Centre For Molecular Biology And Medicine, | Quinone derivatives for enhancing cellular bioenergy |
| 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 |
| ES2209118T3 (es) * | 1997-02-12 | 2004-06-16 | Mse Pharmazeutika Gmbh | Empleo de 2,3-dimetoxi-5-metil-6-decaprenil-1,4-benzoquinona en el tratamiento del zumbido de oidos. |
| US6228891B1 (en) * | 1997-02-12 | 2001-05-08 | Mse Pharmazeutika Gmbh | Use of 2,3-dimethoxy-5-methyl-6-decaprenyl-1,4-benzoquinone |
| 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 |
| EP1351912A2 (en) * | 2000-12-21 | 2003-10-15 | Cancer Research Ventures Limited | Substituted stilbenes, their reactions and anticancer activity |
| 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 |
| 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 |
| US20070021497A1 (en) * | 2005-07-11 | 2007-01-25 | The Fruitful Yield | Vitamin e compositions |
| DK1933821T3 (da) | 2005-09-15 | 2020-10-26 | Ptc Therapeutics Inc | Halevarianter af redox-aktive terapeutika til behandling af mitokondriesygdomme og andre tilstande og modulation af energibiomarkører |
| EA019675B1 (ru) | 2006-02-22 | 2014-05-30 | Эдисон Фармасьютикалз, Инк. | Редокс-активные терапевтические средства для лечения митохондриальных заболеваний и модуляции биомаркера коэнзима q |
| US7786100B2 (en) * | 2006-03-20 | 2010-08-31 | The Regents Of The University Of Michigan | Composition and method of treating hearing loss |
| SI2220030T1 (sl) * | 2007-11-06 | 2016-04-29 | Edison Pharmaceuticals, Inc. | Derivati 4-(p-kuinonil)-2-hidroksibutanamida za zdravljenje mitohondrijskih bolezni |
| WO2009089224A1 (en) * | 2008-01-08 | 2009-07-16 | Edison Pharmaceuticals, Inc. | (HET) ARYL-p-QUINONE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES |
| US8716527B2 (en) * | 2008-03-05 | 2014-05-06 | Edison Pharmaceuticals, Inc. | 2-substituted-p-quinone derivatives for treatment of oxidative stress diseases |
-
2009
- 2009-03-04 US US12/919,004 patent/US20110046156A1/en not_active Abandoned
- 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 WO PCT/US2009/035996 patent/WO2009111543A2/en not_active Ceased
- 2009-03-04 CA CA2717741A patent/CA2717741C/en not_active Expired - Fee Related
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| US20110046156A1 (en) | 2011-02-24 |
| JP6131200B2 (ja) | 2017-05-17 |
| WO2009111543A3 (en) | 2009-12-30 |
| JP2015205938A (ja) | 2015-11-19 |
| JP2014077019A (ja) | 2014-05-01 |
| EP2262519A4 (en) | 2011-03-23 |
| US20140249160A1 (en) | 2014-09-04 |
| US20180200248A1 (en) | 2018-07-19 |
| EP2262519A2 (en) | 2010-12-22 |
| JP2017193590A (ja) | 2017-10-26 |
| WO2009111543A2 (en) | 2009-09-11 |
| CA2717741A1 (en) | 2009-09-11 |
| JP2011513420A (ja) | 2011-04-28 |
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