JP2018500317A5 - - Google Patents
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- Publication number
- JP2018500317A5 JP2018500317A5 JP2017531893A JP2017531893A JP2018500317A5 JP 2018500317 A5 JP2018500317 A5 JP 2018500317A5 JP 2017531893 A JP2017531893 A JP 2017531893A JP 2017531893 A JP2017531893 A JP 2017531893A JP 2018500317 A5 JP2018500317 A5 JP 2018500317A5
- Authority
- JP
- Japan
- Prior art keywords
- trolox
- item
- salt
- resolving agent
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 claims description 93
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- GLEVLJDDWXEYCO-AWEZNQCLSA-N (2s)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound O1[C@](C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-AWEZNQCLSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 11
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 8
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical class O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 claims description 7
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims description 7
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- STVVMTBJNDTZBF-SECBINFHSA-N (2r)-2-amino-3-phenylpropan-1-ol Chemical compound OC[C@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-SECBINFHSA-N 0.000 claims description 4
- -1 Compound (S) -Trolox (1R, 2R)-(−)-Pseudoephedrine salt Chemical class 0.000 claims description 4
- STVVMTBJNDTZBF-VIFPVBQESA-N L-phenylalaninol Chemical compound OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims 1
- 229960003908 pseudoephedrine Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 208000013200 Stress disease Diseases 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 230000036542 oxidative stress Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWGRBVOPPLSCSI-SCZZXKLOSA-N (1r,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical group CN[C@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-SCZZXKLOSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical group CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical group CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000010992 reflux Methods 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/US2015/066208 WO2016100576A1 (en) | 2014-12-16 | 2015-12-16 | Methods for chiral resolution of trolox |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018500317A JP2018500317A (ja) | 2018-01-11 |
| JP2018500317A5 true JP2018500317A5 (enExample) | 2019-01-31 |
Family
ID=56684375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017531893A Withdrawn JP2018500317A (ja) | 2014-12-16 | 2015-12-16 | トロロックスのキラル分割のための方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20180002247A1 (enExample) |
| EP (1) | EP3233819A1 (enExample) |
| JP (1) | JP2018500317A (enExample) |
| WO (1) | WO2016100576A1 (enExample) |
Families Citing this family (12)
| 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 |
| WO2021097249A1 (en) * | 2019-11-14 | 2021-05-20 | Senseonics, Incorporated | Mediation of in vivo analyte signal degradation |
| 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 |
| JP7223738B2 (ja) | 2020-11-12 | 2023-02-16 | 株式会社アルバック | スパッタリング装置 |
| IL319633A (en) * | 2022-09-30 | 2025-05-01 | Ptc Therapeutics Inc | Oxygen cleavage method of trolox amide |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947473A (en) | 1972-12-22 | 1976-03-30 | Hoffman-La Roche Inc. | Antioxidant chroman compounds |
| US4026907A (en) | 1973-11-19 | 1977-05-31 | Hoffmann-La Roche Inc. | Antioxidant chroman compounds |
| US4003919A (en) | 1973-11-19 | 1977-01-18 | Hoffmann-La Roche Inc. | Antioxidant chroman compounds |
| US4018799A (en) * | 1973-11-19 | 1977-04-19 | Hoffmann-La Roche Inc. | Antioxidant chroman compounds |
| US5348973A (en) * | 1990-10-09 | 1994-09-20 | Rhone-Poulenc Chimie | Resolution of hydroxychroman-2-carboxylic acid esters by enantiomeric hydrolysis |
| 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 |
| 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 |
| 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 |
| 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 |
| DK2220030T3 (en) * | 2007-11-06 | 2016-04-11 | Edison Pharmaceuticals Inc | 4- (P-QUINONYL) -2-HYDROXYBUTANAMIDDERIVATER TO TREAT mitochondrial |
| 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 |
| JP5598330B2 (ja) | 2008-10-29 | 2014-10-01 | 三菱瓦斯化学株式会社 | 光学活性有機カルボン酸の製造方法 |
-
2015
- 2015-12-16 EP EP15820772.0A patent/EP3233819A1/en not_active Withdrawn
- 2015-12-16 WO PCT/US2015/066208 patent/WO2016100576A1/en not_active Ceased
- 2015-12-16 US US15/536,514 patent/US20180002247A1/en not_active Abandoned
- 2015-12-16 JP JP2017531893A patent/JP2018500317A/ja not_active Withdrawn
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