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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- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 7
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- 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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- 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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- 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
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- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims description 2
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- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims description 2
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- 108010024882 Electron Transport Complex III Proteins 0.000 claims description 2
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- 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
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- 206010059521 Methylmalonic aciduria Diseases 0.000 claims description 2
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- 208000004622 abetalipoproteinemia Diseases 0.000 claims description 2
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- 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
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- 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
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- 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
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- 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
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- 208000024412 Friedreich ataxia Diseases 0.000 claims 2
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- 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
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- 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
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- 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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- 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
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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 (enExample) | 2019-01-31 |
| JP6810692B2 JP6810692B2 (ja) | 2021-01-06 |
Family
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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 (enExample) |
| EP (2) | EP3233786B1 (enExample) |
| JP (4) | JP6810692B2 (enExample) |
| KR (1) | KR102626895B1 (enExample) |
| CN (2) | CN107531616B (enExample) |
| AU (3) | AU2015364640B2 (enExample) |
| BR (1) | BR112017012988B1 (enExample) |
| CA (1) | CA2971252C (enExample) |
| DK (1) | DK3233786T3 (enExample) |
| ES (1) | ES2912585T3 (enExample) |
| HU (1) | HUE058877T2 (enExample) |
| IL (1) | IL252953A0 (enExample) |
| MX (2) | MX385049B (enExample) |
| NZ (1) | NZ733528A (enExample) |
| PL (1) | PL3233786T3 (enExample) |
| PT (1) | PT3233786T (enExample) |
| RU (1) | RU2770091C2 (enExample) |
| SG (2) | SG11201704968XA (enExample) |
| SI (1) | SI3233786T1 (enExample) |
| WO (1) | WO2016100579A1 (enExample) |
| ZA (1) | ZA201704639B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2564843B1 (en) | 2005-06-01 | 2018-12-26 | Bioelectron Technology Corporation | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| DK2220030T3 (en) | 2007-11-06 | 2016-04-11 | Edison Pharmaceuticals Inc | 4- (P-QUINONYL) -2-HYDROXYBUTANAMIDDERIVATER TO TREAT mitochondrial |
| ES2553557T3 (es) | 2008-10-28 | 2015-12-10 | Edison Pharmaceuticals, Inc. | Proceso para la producción de alfa-tocotrienol y derivados |
| 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 |
| PL3233786T3 (pl) | 2014-12-16 | 2022-06-13 | Ptc Therapeutics, Inc. | Polimorficzne i amorficzne postacie (r)-2-hydroksy-2-metylo-4-(2,4,5-trimetylo-3,6-dioksocykloheksa-1,4-dienylo)butanoamidu |
| 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 |
| 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 |
| BR112021007153A2 (pt) | 2018-10-17 | 2021-07-20 | Ptc Therapeutics, Inc. | 2,3,5-trimetil-6-nonilcicloexa-2,5-dieno-1,4-diona para a supressão e tratamento de a-sinucleinopatias, tauopatias e outros distúrbios |
| 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 |
| CN115066420B (zh) * | 2020-02-21 | 2024-12-10 | Ptc医疗公司 | 光学拆分的Trolox中间体和其制造方法 |
| WO2023283466A1 (en) | 2021-07-08 | 2023-01-12 | Ptc Therapeutics, Inc. | Pharmaceutical compositions comprising 2,3,5-trimethyl-6-nonylcyclohexa-2,5-diene-1,4-dione |
| JPWO2024058099A1 (enExample) | 2022-09-12 | 2024-03-21 | ||
| IL319633A (en) * | 2022-09-30 | 2025-05-01 | Ptc Therapeutics Inc | Oxygen 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 |
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