JP2012506910A5 - - Google Patents
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- JP2012506910A5 JP2012506910A5 JP2011534678A JP2011534678A JP2012506910A5 JP 2012506910 A5 JP2012506910 A5 JP 2012506910A5 JP 2011534678 A JP2011534678 A JP 2011534678A JP 2011534678 A JP2011534678 A JP 2011534678A JP 2012506910 A5 JP2012506910 A5 JP 2012506910A5
- Authority
- JP
- Japan
- Prior art keywords
- tocotrienol
- extract
- item
- tocols
- optionally
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims description 66
- RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 claims description 41
- 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 41
- 235000019145 α-tocotrienol Nutrition 0.000 claims description 40
- 229940064063 alpha tocotrienol Drugs 0.000 claims description 37
- 239000011730 α-tocotrienol Substances 0.000 claims description 37
- 239000000284 extract Substances 0.000 claims description 20
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- 239000000741 silica gel Substances 0.000 claims description 17
- 229910002027 silica gel Inorganic materials 0.000 claims description 17
- 238000001914 filtration Methods 0.000 claims description 15
- DFUSDJMZWQVQSF-XLGIIRLISA-N (2r)-2-methyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol Chemical class OC1=CC=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 DFUSDJMZWQVQSF-XLGIIRLISA-N 0.000 claims description 14
- 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 12
- 239000000419 plant extract Substances 0.000 claims description 12
- 239000003638 chemical reducing agent Substances 0.000 claims description 11
- 238000007281 aminoalkylation reaction Methods 0.000 claims description 10
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 235000019482 Palm oil Nutrition 0.000 claims description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 229940087168 alpha tocopherol Drugs 0.000 claims description 8
- 239000002540 palm oil Substances 0.000 claims description 8
- 229920002866 paraformaldehyde Polymers 0.000 claims description 8
- 229960000984 tocofersolan Drugs 0.000 claims description 8
- 235000004835 α-tocopherol Nutrition 0.000 claims description 8
- 239000002076 α-tocopherol Substances 0.000 claims description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 240000007594 Oryza sativa Species 0.000 claims description 4
- 235000007164 Oryza sativa Nutrition 0.000 claims description 4
- 229910000085 borane Inorganic materials 0.000 claims description 4
- -1 cyclic amine Chemical class 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 235000009566 rice Nutrition 0.000 claims description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical group [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000003773 α-tocotrienols Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 229940069780 barley extract Drugs 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 2
- 235000013399 edible fruits Nutrition 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- 235000010384 tocopherol Nutrition 0.000 claims description 2
- 229960001295 tocopherol Drugs 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 239000011731 tocotrienol Substances 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000006557 surface reaction Methods 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19758508P | 2008-10-28 | 2008-10-28 | |
| US61/197,585 | 2008-10-28 | ||
| PCT/US2009/062212 WO2010051277A1 (en) | 2008-10-28 | 2009-10-27 | Process for the production of alpha-tocotrienol and derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014177733A Division JP6001025B2 (ja) | 2008-10-28 | 2014-09-02 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012506910A JP2012506910A (ja) | 2012-03-22 |
| JP2012506910A5 true JP2012506910A5 (enExample) | 2012-12-06 |
| JP5775459B2 JP5775459B2 (ja) | 2015-09-09 |
Family
ID=42118126
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011534678A Active JP5775459B2 (ja) | 2008-10-28 | 2009-10-27 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2014177733A Active JP6001025B2 (ja) | 2008-10-28 | 2014-09-02 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2015140302A Withdrawn JP2015187169A (ja) | 2008-10-28 | 2015-07-14 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2018108448A Active JP7181708B2 (ja) | 2008-10-28 | 2018-06-06 | α－トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2019008496A Withdrawn JP2019065041A (ja) | 2008-10-28 | 2019-01-22 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2021016310A Withdrawn JP2021066745A (ja) | 2008-10-28 | 2021-02-04 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2023057343A Withdrawn JP2023073469A (ja) | 2008-10-28 | 2023-03-31 | α－トコトリエノールおよび誘導体の産生のためのプロセス |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014177733A Active JP6001025B2 (ja) | 2008-10-28 | 2014-09-02 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2015140302A Withdrawn JP2015187169A (ja) | 2008-10-28 | 2015-07-14 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2018108448A Active JP7181708B2 (ja) | 2008-10-28 | 2018-06-06 | α－トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2019008496A Withdrawn JP2019065041A (ja) | 2008-10-28 | 2019-01-22 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2021016310A Withdrawn JP2021066745A (ja) | 2008-10-28 | 2021-02-04 | α−トコトリエノールおよび誘導体の産生のためのプロセス |
| JP2023057343A Withdrawn JP2023073469A (ja) | 2008-10-28 | 2023-03-31 | α－トコトリエノールおよび誘導体の産生のためのプロセス |
Country Status (17)
| Country | Link |
|---|---|
| US (6) | US8106223B2 (enExample) |
| EP (3) | EP3450431B1 (enExample) |
| JP (7) | JP5775459B2 (enExample) |
| CN (2) | CN102264730B (enExample) |
| BR (1) | BRPI0920414B1 (enExample) |
| CA (2) | CA2974482C (enExample) |
| DK (2) | DK2963006T3 (enExample) |
| EA (2) | EA201692046A1 (enExample) |
| ES (2) | ES2553557T3 (enExample) |
| HU (1) | HUE041714T2 (enExample) |
| MX (1) | MX2011004440A (enExample) |
| MY (2) | MY185183A (enExample) |
| PL (2) | PL2963006T3 (enExample) |
| PT (2) | PT2362875E (enExample) |
| SI (1) | SI2963006T1 (enExample) |
| TR (1) | TR201819154T4 (enExample) |
| WO (1) | WO2010051277A1 (enExample) |
Families Citing this family (36)
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| US7470798B2 (en) | 2003-09-19 | 2008-12-30 | Edison Pharmaceuticals, Inc. | 7,8-bicycloalkyl-chroman derivatives |
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| DK2220030T3 (en) | 2007-11-06 | 2016-04-11 | Edison Pharmaceuticals Inc | 4- (P-QUINONYL) -2-HYDROXYBUTANAMIDDERIVATER TO TREAT mitochondrial |
| EP2237664A4 (en) * | 2008-01-08 | 2013-05-22 | Edison Pharmaceuticals Inc | (HET) ARYL-p-CHINONE DERIVATIVES FOR THE TREATMENT OF OCHONDRIAL DISEASES |
| EP2262508B1 (en) | 2008-03-05 | 2018-10-03 | BioElectron Technology Corporation | SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES |
| CA2729227C (en) | 2008-06-25 | 2018-05-22 | Andrew W. Hinman | 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases |
| MX363223B (es) | 2008-09-10 | 2019-03-15 | Bioelectron Tech Corp | Tratamiento de trastornos generalizados del desarrollo con terapeuticos con actividad redox. |
| 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 |
| ES2553557T3 (es) | 2008-10-28 | 2015-12-10 | Edison Pharmaceuticals, Inc. | Proceso para la producción de alfa-tocotrienol y derivados |
| PL2424495T3 (pl) | 2009-04-28 | 2018-06-29 | Bioelectron Technology Corporation | Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu |
| HUE037592T2 (hu) * | 2009-08-26 | 2018-09-28 | Bioelectron Tech Corp | Eljárások cerebrális ischemia megelõzésére és kezelésére |
| WO2012154613A1 (en) * | 2011-05-06 | 2012-11-15 | Edison Pharmaceuticals, Inc. | Improved process for the preparation of d-alpha-tocotrienol from natural extracts |
| US9464016B2 (en) | 2011-06-14 | 2016-10-11 | Edison Pharmaceuticals, Inc. | Catechol derivatives for treatment of oxidative stress diseases |
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| US9868711B2 (en) | 2013-03-15 | 2018-01-16 | Bioelectron Technology Corporation | Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders |
| US9296712B2 (en) | 2013-03-15 | 2016-03-29 | Edison Pharmaceuticals, Inc. | Resorufin derivatives for treatment of oxidative stress disorders |
| EP2970158B1 (en) | 2013-03-15 | 2019-02-20 | BioElectron Technology Corporation | Alkyl-heteroaryl substituted quinone derivatives for treatment of oxidative stress disorders |
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| CN104262315A (zh) * | 2014-09-05 | 2015-01-07 | 宁波大红鹰生物工程股份有限公司 | 一种生育三烯酚的分离提纯方法 |
| 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 |
| JP2018502127A (ja) | 2015-01-12 | 2018-01-25 | バイオエレクトロン テクノロジー コーポレイション | 放射線被曝に対する防護のためのキノン |
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| 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 |
| WO2018191732A1 (en) | 2017-04-14 | 2018-10-18 | Bioelectron Technology Corporation | Methods and compositions for treatment of inflammation and oxidative stress |
| 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 |
| CA3156499A1 (en) | 2019-10-04 | 2021-04-08 | Stealth Biotherapeutics Inc. | CHINONE, HYDROCHINONE AND NAPHTOCHINONE ANALOGS OF VATIQUINONE FOR THE TREATMENT OF DISEASES WITH MITOCHONDRIAL DISORDERS |
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