JP2018500326A5 - - Google Patents
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- JP2018500326A5 JP2018500326A5 JP2017532088A JP2017532088A JP2018500326A5 JP 2018500326 A5 JP2018500326 A5 JP 2018500326A5 JP 2017532088 A JP2017532088 A JP 2017532088A JP 2017532088 A JP2017532088 A JP 2017532088A JP 2018500326 A5 JP2018500326 A5 JP 2018500326A5
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- 239000000203 mixture Substances 0.000 claims description 122
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 35
- -1 2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl Chemical group 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 21
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 20
- 208000013200 Stress disease Diseases 0.000 claims description 17
- 230000036542 oxidative stress Effects 0.000 claims description 17
- 238000002411 thermogravimetry Methods 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
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- 208000006011 Stroke Diseases 0.000 claims description 7
- 230000007812 deficiency Effects 0.000 claims description 7
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 7
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- 231100000888 hearing loss Toxicity 0.000 claims description 7
- 208000016354 hearing loss disease Diseases 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- 208000023105 Huntington disease Diseases 0.000 claims description 6
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims description 6
- 239000000090 biomarker Substances 0.000 claims description 6
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 6
- 208000001992 Autosomal Dominant Optic Atrophy Diseases 0.000 claims description 5
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- 238000004128 high performance liquid chromatography Methods 0.000 claims description 5
- 208000020911 optic nerve disease Diseases 0.000 claims description 5
- 208000031229 Cardiomyopathies Diseases 0.000 claims description 4
- 206010058892 Carnitine deficiency Diseases 0.000 claims description 4
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims description 4
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims description 4
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims description 4
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims description 4
- 208000014844 Mitochondrial neurogastrointestinal encephalomyopathy Diseases 0.000 claims description 4
- 206010065271 Mitochondrial neurogastrointestinal encephalopathy Diseases 0.000 claims description 4
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims description 4
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- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims description 4
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims description 4
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- 108700005857 Carnitine palmitoyl transferase 1A deficiency Proteins 0.000 claims description 2
- 208000005359 Carnitine palmitoyl transferase 1A deficiency Diseases 0.000 claims description 2
- 108700005858 Carnitine palmitoyl transferase 2 deficiency Proteins 0.000 claims description 2
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims description 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 2
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- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims description 2
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- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims description 2
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims description 2
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- 102000015782 Electron Transport Complex III Human genes 0.000 claims description 2
- 108010024882 Electron Transport Complex III Proteins 0.000 claims description 2
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- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 208000018565 Hemochromatosis Diseases 0.000 claims description 2
- 101000804964 Homo sapiens DNA polymerase subunit gamma-1 Proteins 0.000 claims description 2
- 101001083553 Homo sapiens Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Proteins 0.000 claims description 2
- 101000841267 Homo sapiens Long chain 3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 claims description 2
- 101000595929 Homo sapiens POLG alternative reading frame Proteins 0.000 claims description 2
- 102100030358 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Human genes 0.000 claims description 2
- 208000026350 Inborn Genetic disease Diseases 0.000 claims description 2
- 208000025069 Juvenile Huntington disease Diseases 0.000 claims description 2
- 102100029107 Long chain 3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 claims description 2
- 108010027062 Long-Chain Acyl-CoA Dehydrogenase Proteins 0.000 claims description 2
- 102000018653 Long-Chain Acyl-CoA Dehydrogenase Human genes 0.000 claims description 2
- 102100021644 Long-chain specific acyl-CoA dehydrogenase, mitochondrial Human genes 0.000 claims description 2
- 208000035719 Maculopathy Diseases 0.000 claims description 2
- 206010059521 Methylmalonic aciduria Diseases 0.000 claims description 2
- 206010059396 Mitochondrial DNA depletion Diseases 0.000 claims description 2
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- 102100035196 POLG alternative reading frame Human genes 0.000 claims description 2
- 208000013234 Pearson syndrome Diseases 0.000 claims description 2
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- 208000002903 Thalassemia Diseases 0.000 claims description 2
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- 208000004622 abetalipoproteinemia Diseases 0.000 claims description 2
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- 230000001919 adrenal effect Effects 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 201000004010 carnitine palmitoyltransferase I deficiency Diseases 0.000 claims description 2
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
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- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 208000006443 lactic acidosis Diseases 0.000 claims description 2
- 201000003694 methylmalonic acidemia Diseases 0.000 claims description 2
- 201000007998 methylmalonic aciduria and homocystinuria type cblC Diseases 0.000 claims description 2
- 208000005264 motor neuron disease Diseases 0.000 claims description 2
- 201000003645 multiple acyl-CoA dehydrogenase deficiency Diseases 0.000 claims description 2
- 230000035772 mutation Effects 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 231100000572 poisoning Toxicity 0.000 claims description 2
- 230000000607 poisoning effect Effects 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 2
- 230000035806 respiratory chain Effects 0.000 claims description 2
- 208000001392 short chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- 208000002320 spinal muscular atrophy Diseases 0.000 claims description 2
- 230000009529 traumatic brain injury Effects 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 208000029257 vision disease Diseases 0.000 claims description 2
- 230000004393 visual impairment Effects 0.000 claims description 2
- 208000024412 Friedreich ataxia Diseases 0.000 claims 2
- 208000021642 Muscular disease Diseases 0.000 claims 2
- 201000009623 Myopathy Diseases 0.000 claims 2
- 208000024825 childhood disintegrative disease Diseases 0.000 claims 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 claims 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 101000603761 Homo sapiens Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidase Proteins 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 102100038551 Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidase Human genes 0.000 claims 1
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 229960004203 carnitine Drugs 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
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- 230000008018 melting Effects 0.000 claims 1
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- 208000021090 palsy Diseases 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
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- 210000000278 spinal cord Anatomy 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 32
- 238000001757 thermogravimetry curve Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 7
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XYFMDAJSEGGDKR-UHFFFAOYSA-N 2,3,5-trimethylcyclohexane-1,4-dione Chemical compound CC1CC(=O)C(C)C(C)C1=O XYFMDAJSEGGDKR-UHFFFAOYSA-N 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
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- 206010011903 Deafness traumatic Diseases 0.000 description 1
- 208000001145 Metabolic Syndrome Diseases 0.000 description 1
- 208000001089 Multiple system atrophy Diseases 0.000 description 1
- RHSWDAWJROMVBG-UHFFFAOYSA-N N-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide Chemical compound C(CCC)(=O)NC1=C(C(C(=C(C1=O)C)C)=O)C RHSWDAWJROMVBG-UHFFFAOYSA-N 0.000 description 1
- 208000002946 Noise-Induced Hearing Loss Diseases 0.000 description 1
- 208000002009 Pyruvate Dehydrogenase Complex Deficiency Disease Diseases 0.000 description 1
- 208000032400 Retinal pigmentation Diseases 0.000 description 1
- 206010038933 Retinopathy of prematurity Diseases 0.000 description 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
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- 239000003053 toxin Substances 0.000 description 1
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- 108700012359 toxins Proteins 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462092743P | 2014-12-16 | 2014-12-16 | |
| US62/092,743 | 2014-12-16 | ||
| US201562133276P | 2015-03-13 | 2015-03-13 | |
| US62/133,276 | 2015-03-13 | ||
| PCT/US2015/066211 WO2016100579A1 (en) | 2014-12-16 | 2015-12-16 | Polymorphic and amorphous forms of (r)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020039715A Division JP7111759B2 (ja) | 2014-12-16 | 2020-03-09 | （ｒ）－２－ヒドロキシ－２－メチル－４－（２，４，５－トリメチル－３，６－ジオキソシクロヘキサ－１，４－ジエニル）ブタンアミドの多形性形態および非晶質形態 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018500326A JP2018500326A (ja) | 2018-01-11 |
| JP2018500326A5 true JP2018500326A5 (https=) | 2019-01-31 |
| JP6810692B2 JP6810692B2 (ja) | 2021-01-06 |
Family
ID=55071223
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017532088A Active JP6810692B2 (ja) | 2014-12-16 | 2015-12-16 | （ｒ）−２−ヒドロキシ−２−メチル−４−（２，４，５−トリメチル−３，６−ジオキソシクロヘキサ−１，４−ジエニル）ブタンアミドの多形性形態および非晶質形態 |
| JP2020039715A Active JP7111759B2 (ja) | 2014-12-16 | 2020-03-09 | （ｒ）－２－ヒドロキシ－２－メチル－４－（２，４，５－トリメチル－３，６－ジオキソシクロヘキサ－１，４－ジエニル）ブタンアミドの多形性形態および非晶質形態 |
| JP2021146086A Active JP7277061B2 (ja) | 2014-12-16 | 2021-09-08 | （ｒ）－２－ヒドロキシ－２－メチル－４－（２，４，５－トリメチル－３，６－ジオキソシクロヘキサ－１，４－ジエニル）ブタンアミドの多形性形態および非晶質形態 |
| JP2022094160A Active JP7541546B2 (ja) | 2014-12-16 | 2022-06-10 | （ｒ）－２－ヒドロキシ－２－メチル－４－（２，４，５－トリメチル－３，６－ジオキソシクロヘキサ－１，４－ジエニル）ブタンアミドの多形性形態および非晶質形態 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020039715A Active JP7111759B2 (ja) | 2014-12-16 | 2020-03-09 | （ｒ）－２－ヒドロキシ－２－メチル－４－（２，４，５－トリメチル－３，６－ジオキソシクロヘキサ－１，４－ジエニル）ブタンアミドの多形性形態および非晶質形態 |
| JP2021146086A Active JP7277061B2 (ja) | 2014-12-16 | 2021-09-08 | （ｒ）－２－ヒドロキシ－２－メチル－４－（２，４，５－トリメチル－３，６－ジオキソシクロヘキサ－１，４－ジエニル）ブタンアミドの多形性形態および非晶質形態 |
| JP2022094160A Active JP7541546B2 (ja) | 2014-12-16 | 2022-06-10 | （ｒ）－２－ヒドロキシ－２－メチル－４－（２，４，５－トリメチル－３，６－ジオキソシクロヘキサ－１，４－ジエニル）ブタンアミドの多形性形態および非晶質形態 |
Country Status (21)
| Country | Link |
|---|---|
| US (5) | US10251847B2 (https=) |
| EP (2) | EP3233786B1 (https=) |
| JP (4) | JP6810692B2 (https=) |
| KR (1) | KR102626895B1 (https=) |
| CN (2) | CN107531616B (https=) |
| AU (3) | AU2015364640B2 (https=) |
| BR (1) | BR112017012988B1 (https=) |
| CA (1) | CA2971252C (https=) |
| DK (1) | DK3233786T3 (https=) |
| ES (1) | ES2912585T3 (https=) |
| HU (1) | HUE058877T2 (https=) |
| IL (1) | IL252953A0 (https=) |
| MX (2) | MX385049B (https=) |
| NZ (1) | NZ733528A (https=) |
| PL (1) | PL3233786T3 (https=) |
| PT (1) | PT3233786T (https=) |
| RU (1) | RU2770091C2 (https=) |
| SG (2) | SG11201704968XA (https=) |
| SI (1) | SI3233786T1 (https=) |
| WO (1) | WO2016100579A1 (https=) |
| ZA (1) | ZA201704639B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2471530B1 (en) | 2005-06-01 | 2017-01-11 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| WO2009061744A2 (en) | 2007-11-06 | 2009-05-14 | Edison Pharmaceuticals, Inc. | 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| CA2741767C (en) | 2008-10-28 | 2017-09-12 | Ptc Therapeutics, Inc. | Process for the production of alpha-tocotrienol and derivatives |
| 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 |
| AU2015364640B2 (en) | 2014-12-16 | 2020-08-13 | Ptc Therapeutics, Inc. | Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
| EP3390377B1 (en) | 2015-12-16 | 2026-03-25 | PTC Therapeutics, Inc. | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| WO2017106803A1 (en) | 2015-12-17 | 2017-06-22 | Bioelectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| 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 |
| KR20210076956A (ko) | 2018-10-17 | 2021-06-24 | 피티씨 테라퓨틱스, 인크. | α-시누클레인병증, 타우병증 및 기타 장애를 억제 및 치료하기 위한 2,3,5-트리메틸-6-노닐사이클로헥사-2,5-디엔-1,4-디온 |
| TWI886158B (zh) | 2019-10-10 | 2025-06-11 | 加拿大商再諾製藥公司 | 選擇性鉀通道調節劑之固態晶型 |
| KR20220143897A (ko) * | 2020-02-21 | 2022-10-25 | 스미토모 파마 가부시키가이샤 | 광학 분할된 트롤록스 중간체 및 그 제조 방법 |
| PE20240893A1 (es) | 2021-07-08 | 2024-04-24 | Ptc Therapeutics Inc | Composiciones farmaceuticas que comprenden 2,3,5-trimetil-6-nonilciclohexa-2,5-dien-1,4-diona |
| EP4588473A1 (en) * | 2022-09-12 | 2025-07-23 | PTC Therapeutics, Inc. | Granules for suspension |
| EP4596530A1 (en) * | 2022-09-30 | 2025-08-06 | PTC Therapeutics, Inc. | Oxidative cleavage method of trolox amide |
| WO2025193975A1 (en) | 2024-03-13 | 2025-09-18 | Ptc Therapeutics, Inc. | Formulations for stabilizing dissolution of medicaments |
Family Cites Families (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4018799A (en) | 1973-11-19 | 1977-04-19 | Hoffmann-La Roche Inc. | Antioxidant chroman compounds |
| US4026907A (en) | 1973-11-19 | 1977-05-31 | Hoffmann-La Roche Inc. | Antioxidant chroman compounds |
| JPS5640651A (en) | 1979-09-12 | 1981-04-16 | Takeda Chem Ind Ltd | Quinone compound and its preparation |
| US5272180A (en) | 1987-07-29 | 1993-12-21 | Takeda Chemical Industries, Ltd. | Cell proliferation inhibitor |
| US5348973A (en) | 1990-10-09 | 1994-09-20 | Rhone-Poulenc Chimie | Resolution of hydroxychroman-2-carboxylic acid esters by enantiomeric hydrolysis |
| US6150402A (en) | 1994-08-15 | 2000-11-21 | Loma Linda University Medical Center | Natriuretic compounds |
| SK282144B6 (sk) | 1994-12-28 | 2001-11-06 | Janssen Pharmaceutica N. V. | Liečivo na terapeutické a profylaktické ošetrenie degeneratívnych chorôb vaskulárneho systému a nervovej sústavy, ktoré súvisia s oxidačným stresom |
| AU6709896A (en) | 1995-08-21 | 1997-03-12 | Takeda Chemical Industries Ltd. | Quinone compound, its production and use |
| US6232060B1 (en) | 1996-01-19 | 2001-05-15 | Galileo Laboratories, Inc. | Assay system for anti-stress agents |
| US5801159A (en) | 1996-02-23 | 1998-09-01 | Galileo Laboratories, Inc. | Method and composition for inhibiting cellular irreversible changes due to stress |
| DE69712888D1 (de) | 1996-07-11 | 2002-07-04 | Takeda Chemical Industries Ltd | ZUSAMMENSTELLUNGEN DIE beta-AMYLOID PROTEIN BEDINGTE ZYTOTOXIZITÄT VERHINDERN |
| US5821247A (en) | 1996-09-19 | 1998-10-13 | Japan Energy Corporation | Hydroquinone derivative and pharmaceutical use thereof |
| JP3093170B2 (ja) * | 1996-09-19 | 2000-10-03 | 株式会社ジャパンエナジー | ヒドロキノン誘導体及びその医薬用途 |
| JP3913329B2 (ja) * | 1997-09-11 | 2007-05-09 | 株式会社クラレ | （±）−クロマンカルボン酸の光学分割法 |
| 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 |
| WO2000078296A2 (en) | 1999-06-17 | 2000-12-28 | Basf Aktiengesellschaft | Tocotrienol and/or tocotrienol derivatives for the treatment or prophylaxis of glutamate- and/or calcium-induced disorders |
| US6426362B1 (en) | 1999-10-08 | 2002-07-30 | Galileo Laboratories, Inc. | Formulations of tocopherols and methods of making and using them |
| US6528042B1 (en) | 1999-10-08 | 2003-03-04 | Galileo Laboratories, Inc. | Compositions of flavonoids for use as cytoprotectants and methods of making and using them |
| WO2002012221A1 (en) | 2000-08-03 | 2002-02-14 | Kuraray Co., Ltd. | Method for optical resolution of (±)-6-hydroxy-2,5,7,8-tetramethylcoumarone-2-carboxylic acid |
| US7034054B2 (en) | 2000-12-15 | 2006-04-25 | Galileo Pharmaceuticals, Inc. | Methods for the prevention and treatment of cerebral ischemia using non-alpha tocopherols |
| WO2002047680A2 (en) | 2000-12-15 | 2002-06-20 | Galileo Laboratories, Inc. | Use of tocopherol, metabolites or derivatives thereof or flavonoid metabolites or derivatives thereof in the manufacture of a medicament for the treatment of tissue ischemia |
| US6608196B2 (en) | 2001-05-03 | 2003-08-19 | Galileo Pharmaceuticals, Inc. | Process for solid supported synthesis of pyruvate-derived compounds |
| NZ513547A (en) | 2001-08-13 | 2002-09-27 | Antipodean Biotechnology Ltd | Synthesis of triphenylphosphonium quinols (e.g. mitoquinol) and/or quinones (e.g. mitoquinone) |
| WO2003015494A2 (en) | 2001-08-21 | 2003-02-27 | Galileo Pharmaceuticals, Inc. | Tocopherol enriched compositions and amelioration of inflammatory symptoms |
| AU2002352726A1 (en) | 2001-11-15 | 2003-06-10 | Galileo Laboratories, Inc. | Formulations and methods for treatment or amelioration of inflammatory conditions |
| US6667330B2 (en) | 2002-01-31 | 2003-12-23 | Galileo Pharmaceuticals, Inc. | Furanone derivatives |
| US6653346B1 (en) | 2002-02-07 | 2003-11-25 | Galileo Pharmaceuticals, Inc. | Cytoprotective benzofuran derivatives |
| US7078541B2 (en) | 2002-02-07 | 2006-07-18 | Galileo Pharmaceuticals, Inc. | Benzofuran derivatives |
| GB0204232D0 (en) | 2002-02-22 | 2002-04-10 | Isis Innovation | Assay |
| DE60211875T2 (de) | 2002-07-01 | 2006-10-26 | Santhera Pharmaceuticals (Schweiz) Ag | Screeningverfahren und Verbindungen zur Behandlung von Friedreich ataxia |
| JP4599292B2 (ja) | 2002-10-30 | 2010-12-15 | 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 | 物理的−化学的特性に基づく治療用化合物の同定 |
| EP1454627A1 (en) | 2003-03-06 | 2004-09-08 | MyoContract Ltd. | Alpha-Keto carbonyl calpain inhibitors |
| WO2005033092A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | Chroman derivatives |
| US7393662B2 (en) | 2004-09-03 | 2008-07-01 | Centocor, Inc. | Human EPO mimetic hinge core mimetibodies, compositions, methods and uses |
| FR2875803B1 (fr) | 2004-09-24 | 2006-11-24 | Catalys Sarl | Preparation de composes phenol-amides a proprietes antioxydantes |
| EP2471530B1 (en) | 2005-06-01 | 2017-01-11 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| CA2622523C (en) | 2005-09-15 | 2014-02-18 | Edison Pharmaceuticals, Inc. | Tail variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| WO2007095630A2 (en) | 2006-02-15 | 2007-08-23 | The Regents Of The University Of California | New ubiquinone analogs and methods of use |
| US9278085B2 (en) | 2006-02-22 | 2016-03-08 | Edison Pharmaceuticals, Inc. | Side-chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| EP2088144B1 (en) * | 2006-10-26 | 2011-12-28 | Mitsubishi Gas Chemical Company, Inc. | Method of producing s-(-)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid |
| WO2008086025A2 (en) | 2007-01-10 | 2008-07-17 | Edison Pharmaceuticals, Inc. | Treatment of respiratory chain disorders using compounds having erythropoietin or thrombopoietin activity |
| WO2009061744A2 (en) * | 2007-11-06 | 2009-05-14 | Edison Pharmaceuticals, Inc. | 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| WO2009088572A2 (en) | 2008-01-07 | 2009-07-16 | Centocor, Inc. | Method of treating erythropoietin hyporesponsive anemias |
| EA023618B1 (ru) | 2008-01-08 | 2016-06-30 | Эдисон Фармасьютикалз, Инк. | Производные (гет)арил-п-хинона для лечения митохондриальных болезней |
| EP2262519A4 (en) | 2008-03-05 | 2011-03-23 | Edison Pharmaceuticals Inc | TREATMENT OF HEARING AND BALANCING DISORDERS WITH REDOXACTIVE THERAPEUTICS |
| WO2009111576A2 (en) | 2008-03-05 | 2009-09-11 | Edison Pharmaceuticals, Inc. | 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| CA2723621A1 (en) | 2008-05-15 | 2009-11-19 | Edison Pharmaceuticals, Inc | Treatment of hearing and balance impairments using compounds having erythropoietin activity |
| WO2009143268A2 (en) | 2008-05-22 | 2009-11-26 | Edison Pharmaceuticals, Inc. | Treatment of mitochondrial diseases with an erythropoietin mimetic |
| JP5266875B2 (ja) | 2008-05-23 | 2013-08-21 | 三菱瓦斯化学株式会社 | 有機カルボン酸エステルからの光学活性有機カルボン酸の製造方法 |
| WO2009158348A1 (en) | 2008-06-25 | 2009-12-30 | Edison Pharmaceuticals, Inc. | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
| WO2010005989A1 (en) | 2008-07-09 | 2010-01-14 | Edison Pharmaceuticals, Inc. | Dermatological compositions with anti-aging and skin even-toning properties |
| US20100029784A1 (en) | 2008-07-30 | 2010-02-04 | Hinman Andrew W | Naphthoquinone compositions with anti-aging, anti-inflammatory and skin even-toning properties |
| WO2010014758A1 (en) | 2008-07-30 | 2010-02-04 | Edison Pharmaceuticals, Inc. | Use of hydrogenated pyrido[4,3-b] indoles for the treatment of oxidative stress |
| EP2344142B1 (en) | 2008-09-10 | 2024-06-26 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| EP2362726B1 (en) | 2008-10-14 | 2018-08-08 | Bioelectron Technology Corporation | Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells |
| CA2741767C (en) | 2008-10-28 | 2017-09-12 | Ptc Therapeutics, Inc. | Process for the production of alpha-tocotrienol and derivatives |
| PL2424495T3 (pl) | 2009-04-28 | 2018-06-29 | Bioelectron Technology Corporation | Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu |
| JP2012525397A (ja) | 2009-04-28 | 2012-10-22 | 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 | 眼科疾患を治療するためのトコトリエノールキノンの製剤 |
| EP2424360A4 (en) | 2009-04-28 | 2012-10-03 | Ampere Life Sciences Inc | TOPICAL, PERIOCULAR OR INTRAOCULAR USE OF TOCOTRIENOLS FOR THE TREATMENT OF OPHTHALMIC DISEASES |
| EP2609921A1 (en) | 2009-06-25 | 2013-07-03 | Ampere Life Sciences, Inc. | Treatment of pervasive developmental disorders with tocotrienols or tocotrienol enriched extracts |
| DK2470168T3 (en) | 2009-08-26 | 2018-05-07 | Bioelectron Tech Corp | PROCEDURES FOR PREVENTION AND TREATMENT OF CEREBRAL ISCAM |
| WO2011041452A2 (en) | 2009-10-01 | 2011-04-07 | Ampere Life Sciences, Inc. | Mouse model for identifying compounds for the treatment of oxidative stress |
| US20110172312A1 (en) | 2009-12-31 | 2011-07-14 | Miller Guy M | Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones |
| US8464722B2 (en) | 2010-03-04 | 2013-06-18 | Medline Industries, Inc. | Folded telescopic equipment drape and method of folding and using the same |
| SG184787A1 (en) | 2010-03-09 | 2012-11-29 | Edison Pharmaceuticals Inc | Synthesis of alpha-tocopherolquinone derivatives, and methods of using the same |
| WO2011113018A1 (en) | 2010-03-12 | 2011-09-15 | Ampere Life Sciences, Inc. | Measurement and control of biological time |
| AU2011238525A1 (en) | 2010-04-06 | 2012-11-08 | Edison Pharmaceuticals, Inc. | Treatment of Ataxia Telangiectasia |
| CA2797581A1 (en) | 2010-04-27 | 2011-11-03 | Edison Pharmaceuticals, Inc. | Formulations of quinones for the treatment of ophthalmic diseases |
| US20120101169A1 (en) | 2010-07-14 | 2012-04-26 | Penwest Pharmaceuticals Co. | Methods of providing anticoagulation effects in subjects |
| EP2601168A4 (en) | 2010-08-06 | 2013-12-04 | Ampere Life Sciences Inc | TREATMENT OF MITOCHONDRIAL DISEASES BY VITAMIN K |
| EA201300215A1 (ru) | 2010-08-06 | 2013-07-30 | Эдисон Фармасьютикалз, Инк. | Лечение митохондриальных болезней нафтохинонами |
| WO2012068552A1 (en) | 2010-11-19 | 2012-05-24 | Edison Pharmaceuticals, Inc. | Methods for improving blood glucose control |
| WO2012154613A1 (en) | 2011-05-06 | 2012-11-15 | Edison Pharmaceuticals, Inc. | Improved process for the preparation of d-alpha-tocotrienol from natural extracts |
| WO2012170773A1 (en) | 2011-06-08 | 2012-12-13 | Edison Pharmaceuticals, Inc. | Adjunctive therapy for the treatment of mitochondrial disorders with quinones and naphthoquinones |
| WO2012174286A1 (en) | 2011-06-14 | 2012-12-20 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
| WO2013006736A1 (en) | 2011-07-06 | 2013-01-10 | Edison Pharmaceuticals, Inc | Treatment of leigh syndrome and leigh-like syndrome, including complications of sucla2 mutations, with tocotrienol quinones |
| US20150057363A1 (en) | 2011-07-06 | 2015-02-26 | Guy M. Miller | Treatment of methylmalonic aciduria, isovaleric aciduria, and other organic acidurias with tocotrienol quinones |
| JP2014520894A (ja) | 2011-07-19 | 2014-08-25 | エジソン ファーマシューティカルズ， インコーポレイテッド | 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法 |
| CA2883879A1 (en) | 2012-09-07 | 2014-03-13 | Edison Pharmaceuticals, Inc. | Quinone derivatives for use in the modulation of redox status of individuals |
| EA031098B1 (ru) | 2013-03-08 | 2018-11-30 | Юнилевер Н.В. | Соединения резорцина для дерматологического применения |
| US9296712B2 (en) | 2013-03-15 | 2016-03-29 | Edison Pharmaceuticals, Inc. | Resorufin derivatives for treatment of oxidative stress disorders |
| US20140275045A1 (en) | 2013-03-15 | 2014-09-18 | Edison Pharmaceuticals, Inc. | Phenazine-3-one and phenothiazine-3-one 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 |
| AU2014273891A1 (en) | 2013-05-31 | 2015-12-24 | Bioelectron Technology Corporation | Carboxylic acid derivatives for treatment of oxidative stress disorders |
| US20180002247A1 (en) | 2014-12-16 | 2018-01-04 | Bioelectron Technology Corporation | Methods for chiral resolution of trolox |
| AU2015364640B2 (en) | 2014-12-16 | 2020-08-13 | Ptc Therapeutics, Inc. | Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
| WO2016114860A1 (en) | 2015-01-12 | 2016-07-21 | Edison Pharmaceuticals, Inc. | Quinones for protection against radiation exposure |
| EP3390377B1 (en) | 2015-12-16 | 2026-03-25 | PTC Therapeutics, Inc. | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| WO2017106803A1 (en) | 2015-12-17 | 2017-06-22 | Bioelectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| WO2017123823A1 (en) | 2016-01-12 | 2017-07-20 | Bioelectron Technology Corporation | Alkyl-, acyl-, urea-, and aza-uracil sulfide:quinone oxidoreductase inhibitors |
| JP2019501974A (ja) | 2016-01-12 | 2019-01-24 | バイオエレクトロン テクノロジー コーポレイション | チオスルフェートレベルを増加させるためのまたは硫化水素レベルを低下させるためのトコフェロールキノン誘導体およびトコトリエノールキノン誘導体 |
| WO2018081644A1 (en) | 2016-10-28 | 2018-05-03 | Bioelectron Technology Corporation | Methods of analyzing p-hydroquinone levels and ratios |
| WO2018093957A1 (en) | 2016-11-15 | 2018-05-24 | Bioelectron Technology Corporation | 2-substituted amino-naphth[1,2-d]imidazol-5-one compounds or pharmaceutically acceptable salts thereof cross reference to related applications |
| 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 |
| WO2018129411A1 (en) | 2017-01-06 | 2018-07-12 | Bioelectron Technology Corporation | Aryl- and heteroaryl-resorufin derivatives for treatment of oxidative stress disorders and liver and kidney disorders |
| WO2018191732A1 (en) | 2017-04-14 | 2018-10-18 | Bioelectron Technology Corporation | Methods and compositions for treatment of inflammation and oxidative stress |
| US20180333389A1 (en) | 2017-04-14 | 2018-11-22 | Bioelectron Technology Corporation | Vitamin e compositions and methods of use therefor |
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