JP2016521748A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016521748A5 JP2016521748A5 JP2016519582A JP2016519582A JP2016521748A5 JP 2016521748 A5 JP2016521748 A5 JP 2016521748A5 JP 2016519582 A JP2016519582 A JP 2016519582A JP 2016519582 A JP2016519582 A JP 2016519582A JP 2016521748 A5 JP2016521748 A5 JP 2016521748A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- producing
- reaction
- cleavage
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 30
- 238000000034 method Methods 0.000 claims 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 5
- 238000003776 cleavage reaction Methods 0.000 claims 5
- 230000007017 scission Effects 0.000 claims 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 4
- 229910052744 lithium Inorganic materials 0.000 claims 4
- 238000006600 Stobbe condensation reaction Methods 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims 2
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims 2
- 235000012141 vanillin Nutrition 0.000 claims 2
- WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical group BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- 238000012746 preparative thin layer chromatography Methods 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims 1
- IOTJTTYNETYJNK-KYJUHHDHSA-N COc(cc(C[C@@H](CO)[C@@H](Cc(cc1OC)ccc1OCc1ccccc1)CO)cc1)c1OCc1ccccc1 Chemical compound COc(cc(C[C@@H](CO)[C@@H](Cc(cc1OC)ccc1OCc1ccccc1)CO)cc1)c1OCc1ccccc1 IOTJTTYNETYJNK-KYJUHHDHSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361833258P | 2013-06-10 | 2013-06-10 | |
| US61/833,258 | 2013-06-10 | ||
| PCT/US2014/041636 WO2014200964A1 (en) | 2013-06-10 | 2014-06-10 | Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018072178A Division JP6513853B2 (ja) | 2013-06-10 | 2018-04-04 | （ｓ，ｓ）−セコイソラリシレジノールジグルコシド及び（ｒ，ｒ）−セコイソラリシレジノールジグルコシドの製造 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016521748A JP2016521748A (ja) | 2016-07-25 |
| JP2016521748A5 true JP2016521748A5 (enExample) | 2017-07-20 |
| JP6321788B2 JP6321788B2 (ja) | 2018-05-09 |
Family
ID=52022698
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016519582A Expired - Fee Related JP6321788B2 (ja) | 2013-06-10 | 2014-06-10 | （ｓ，ｓ）−セコイソラリシレジノールジグルコシド及び（ｒ，ｒ）−セコイソラリシレジノールジグルコシドの製造 |
| JP2018072178A Expired - Fee Related JP6513853B2 (ja) | 2013-06-10 | 2018-04-04 | （ｓ，ｓ）−セコイソラリシレジノールジグルコシド及び（ｒ，ｒ）−セコイソラリシレジノールジグルコシドの製造 |
| JP2019074548A Active JP6785335B2 (ja) | 2013-06-10 | 2019-04-10 | （ｓ，ｓ）−セコイソラリシレジノールジグルコシド及び（ｒ，ｒ）−セコイソラリシレジノールジグルコシドの製造 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018072178A Expired - Fee Related JP6513853B2 (ja) | 2013-06-10 | 2018-04-04 | （ｓ，ｓ）−セコイソラリシレジノールジグルコシド及び（ｒ，ｒ）−セコイソラリシレジノールジグルコシドの製造 |
| JP2019074548A Active JP6785335B2 (ja) | 2013-06-10 | 2019-04-10 | （ｓ，ｓ）−セコイソラリシレジノールジグルコシド及び（ｒ，ｒ）−セコイソラリシレジノールジグルコシドの製造 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US10030040B2 (enExample) |
| EP (2) | EP3488697A1 (enExample) |
| JP (3) | JP6321788B2 (enExample) |
| KR (1) | KR102270124B1 (enExample) |
| CN (2) | CN107955046A (enExample) |
| AU (1) | AU2014278362B2 (enExample) |
| CA (1) | CA2920346A1 (enExample) |
| CY (1) | CY1120759T1 (enExample) |
| DK (1) | DK3007557T3 (enExample) |
| ES (1) | ES2691845T3 (enExample) |
| HR (1) | HRP20181663T1 (enExample) |
| HU (1) | HUE040022T2 (enExample) |
| IL (2) | IL243029B (enExample) |
| LT (1) | LT3007557T (enExample) |
| PL (1) | PL3007557T3 (enExample) |
| PT (1) | PT3007557T (enExample) |
| RS (1) | RS57846B1 (enExample) |
| SI (1) | SI3007557T1 (enExample) |
| SM (1) | SMT201800575T1 (enExample) |
| TR (1) | TR201815423T4 (enExample) |
| WO (1) | WO2014200964A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR201815423T4 (tr) * | 2013-06-10 | 2018-11-21 | Scripps Research Inst | (s,s)-sekoi̇zolari̇si̇resi̇nol di̇glukozi̇d ve (r,r)-sekoi̇zolari̇si̇resi̇nol di̇glukozi̇d'i̇n hazirlanmasi. |
| US11197876B2 (en) | 2014-05-30 | 2021-12-14 | The Trusiees Of The University Of Pennsylvania | Effects of LGM2605 on a primate model of asthma |
| KR20170010019A (ko) * | 2014-05-30 | 2017-01-25 | 더 트러스티스 오브 더 유니버시티 오브 펜실베니아 | 방사선 및 화학적 손상으로부터 보호하기 위한 세코이솔라리시레시놀 디글루코사이드(ｓｄｇ) 및 관련 화합물의 용도 |
| US20170258821A1 (en) | 2014-05-30 | 2017-09-14 | The Trustees Of The University Of Pennsylvania | USE OF SECOISOLARICIRESINOL DIGLUCOSIDES (SDGs) AND RELATED COMPOUNDS FOR PROTECTION AGAINST RADIATION AND CHEMICAL DAMAGE |
| US20180243327A1 (en) * | 2015-09-01 | 2018-08-30 | The Trustees Of The University Of Pennsylvania | USE OF SECOISOLARICIRESINOL DIGLUCOSIDES (SDGs) AND RELATED COMPOUNDS FOR PROTECTION AGAINST RADIATION DAMAGE |
| WO2017214039A1 (en) | 2016-06-07 | 2017-12-14 | University Of Pennsylvania | Compositions and methods for protecting organs from ischemia/reperfusion injury associated with transplantation |
| BR112019026102A2 (pt) * | 2017-06-12 | 2020-06-30 | Lignamed, Llc | processos para preparação de um composto e de uma mistura de compostos |
| CN110283218A (zh) * | 2019-06-24 | 2019-09-27 | 暨南大学 | 提高木酚素油溶性的改性方法 |
| CN111233944B (zh) * | 2020-03-25 | 2023-02-28 | 宝鸡市辰光生物科技有限公司 | 一种同时制备分离四种木脂素类成分的高效液相方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3065925B2 (ja) * | 1996-01-30 | 2000-07-17 | 日清製油株式会社 | 活性酸素種消去剤及び退色防止剤 |
| KR20010042996A (ko) * | 1998-04-24 | 2001-05-25 | 시몬스메어 래리 엠. | 재조합 세코이솔라리시레시놀 탈수소효소, 및 사용방법 |
| FI110868B (fi) * | 2001-01-22 | 2003-04-15 | Maa Ja Elintarviketalouden Tut | Menetelmä sekoisolarisiresinolidiglykosidin (SDG) eristämiseksi ja puhdistamiseksi pellavansiemenistä |
| US20030060420A1 (en) * | 2001-09-14 | 2003-03-27 | Rick Heintzman | Process for extraction and stabilization of phytoestrogens from flaxseed and product therefrom |
| WO2003084974A1 (en) * | 2002-04-02 | 2003-10-16 | Wiley Organics, Inc. | A process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed |
| JP2006347978A (ja) * | 2005-06-17 | 2006-12-28 | Nippon Flour Mills Co Ltd | 抗肥満剤及びこれを含む食品並びにペットフード |
| JP2007308469A (ja) * | 2005-11-11 | 2007-11-29 | Nippon Flour Mills Co Ltd | リグナンを有効成分とする男性用抗肥満剤 |
| CN100395253C (zh) * | 2006-05-12 | 2008-06-18 | 中国科学院山西煤炭化学研究所 | 一种由亚麻籽制备开环异落叶松树脂酚二葡萄糖苷的方法 |
| CN101117641B (zh) | 2007-07-27 | 2011-05-11 | 大连医诺生物有限公司 | 开环异落叶松树脂酚二葡萄糖苷的制备方法 |
| JP2010057367A (ja) * | 2008-09-01 | 2010-03-18 | Nitto Boseki Co Ltd | 魚肉の褐変防止剤および褐変防止方法 |
| CN102050848A (zh) * | 2009-11-01 | 2011-05-11 | 桂林莱茵生物科技股份有限公司 | 一种亚麻木酚素的制备方法 |
| ES2362065B1 (es) * | 2009-12-15 | 2012-05-18 | Consejo Superior De Investigaciones Cient�?Ficas (Csic) | Compuestos con actividad antiinflamatoria. |
| CA2808746A1 (en) | 2010-08-20 | 2012-02-23 | Federation Des Producteurs Acericoles Du Quebec | Sugar plant derived by-products and methods of production thereof |
| CN102558252A (zh) * | 2010-12-31 | 2012-07-11 | 西安天一生物技术有限公司 | 一种亚麻木酚素的生产工艺 |
| TR201815423T4 (tr) * | 2013-06-10 | 2018-11-21 | Scripps Research Inst | (s,s)-sekoi̇zolari̇si̇resi̇nol di̇glukozi̇d ve (r,r)-sekoi̇zolari̇si̇resi̇nol di̇glukozi̇d'i̇n hazirlanmasi. |
-
2014
- 2014-06-10 TR TR2018/15423T patent/TR201815423T4/tr unknown
- 2014-06-10 US US14/897,181 patent/US10030040B2/en active Active
- 2014-06-10 CN CN201711326022.7A patent/CN107955046A/zh active Pending
- 2014-06-10 HU HUE14811683A patent/HUE040022T2/hu unknown
- 2014-06-10 CA CA2920346A patent/CA2920346A1/en not_active Abandoned
- 2014-06-10 DK DK14811683.3T patent/DK3007557T3/en active
- 2014-06-10 HR HRP20181663TT patent/HRP20181663T1/hr unknown
- 2014-06-10 KR KR1020167000483A patent/KR102270124B1/ko active Active
- 2014-06-10 SI SI201430924T patent/SI3007557T1/sl unknown
- 2014-06-10 RS RS20181236A patent/RS57846B1/sr unknown
- 2014-06-10 JP JP2016519582A patent/JP6321788B2/ja not_active Expired - Fee Related
- 2014-06-10 EP EP18183923.4A patent/EP3488697A1/en not_active Withdrawn
- 2014-06-10 ES ES14811683.3T patent/ES2691845T3/es active Active
- 2014-06-10 EP EP14811683.3A patent/EP3007557B1/en active Active
- 2014-06-10 CN CN201480041131.2A patent/CN105705018B/zh active Active
- 2014-06-10 AU AU2014278362A patent/AU2014278362B2/en not_active Ceased
- 2014-06-10 WO PCT/US2014/041636 patent/WO2014200964A1/en not_active Ceased
- 2014-06-10 SM SM20180575T patent/SMT201800575T1/it unknown
- 2014-06-10 PL PL14811683T patent/PL3007557T3/pl unknown
- 2014-06-10 LT LTEP14811683.3T patent/LT3007557T/lt unknown
- 2014-06-10 PT PT14811683T patent/PT3007557T/pt unknown
-
2015
- 2015-12-10 IL IL243029A patent/IL243029B/en active IP Right Grant
-
2018
- 2018-04-04 JP JP2018072178A patent/JP6513853B2/ja not_active Expired - Fee Related
- 2018-07-23 US US16/042,866 patent/US10870670B2/en active Active
- 2018-10-16 CY CY181101054T patent/CY1120759T1/el unknown
-
2019
- 2019-04-10 JP JP2019074548A patent/JP6785335B2/ja active Active
- 2019-09-24 IL IL26962219A patent/IL269622A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016521748A5 (enExample) | ||
| JP2016153424A5 (enExample) | ||
| JP2011527560A5 (enExample) | ||
| JP2011236247A5 (enExample) | ||
| JP2019048806A5 (enExample) | ||
| EA201070700A1 (ru) | Способы получения циклоалкилкарбоксамидопиридинбензойных кислот | |
| JP2014528463A5 (enExample) | ||
| JP2012506425A5 (enExample) | ||
| JP2012521377A5 (enExample) | ||
| JP2014512451A5 (enExample) | ||
| JP2009185041A5 (enExample) | ||
| JP2013005803A5 (enExample) | ||
| JP2009525279A5 (enExample) | ||
| RU2015103694A (ru) | Способы синтеза спиро-оксиндольных соединений | |
| AR088524A1 (es) | Composicion descongelante, proceso de preparacion, conjunto de parte y uso | |
| JP2015129106A5 (enExample) | ||
| JP2014028813A5 (enExample) | ||
| JP2017505801A5 (enExample) | ||
| JP2013508091A5 (enExample) | ||
| JP2016540036A5 (enExample) | ||
| ES2505065T1 (es) | Procedimiento de preparación de alcoxifenol y alcoxihidroxibenzaldehído | |
| JP2019508387A5 (enExample) | ||
| JP2010205731A5 (enExample) | ||
| JP2010536929A5 (enExample) | ||
| JP2013100237A5 (enExample) |