JP2016521748A5 - - Google Patents
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- 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
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- JP
- Japan
- Prior art keywords
- compound
- formula
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- reaction
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- 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.)
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- 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 (cg-RX-API-DMAC7.html) | 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)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6321788B2 (ja) | 2013-06-10 | 2018-05-09 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | （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 |
| US11197876B2 (en) | 2014-05-30 | 2021-12-14 | The Trusiees Of The University Of Pennsylvania | Effects of LGM2605 on a primate model of asthma |
| MA39899A (fr) * | 2014-05-30 | 2021-05-26 | Univ Pennsylvania | Utilisation de sécoïsolaricirésinol diglucosides (sdg) et composés associés pour la protection contre le rayonnement et les dommages chimiques |
| 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 |
| CN108697748A (zh) * | 2015-09-01 | 2018-10-23 | 宾夕法尼亚大学理事会 | 开环异落叶松树脂酚二葡萄糖苷(sdg)及相关化合物用于防止辐射损伤的用途 |
| WO2017214039A1 (en) | 2016-06-07 | 2017-12-14 | University Of Pennsylvania | Compositions and methods for protecting organs from ischemia/reperfusion injury associated with transplantation |
| CA3065386A1 (en) * | 2017-06-12 | 2018-12-20 | Lignamed, Llc | Process for the preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside |
| 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 |
| EP1071754A4 (en) * | 1998-04-24 | 2001-08-29 | Univ Washington | Recombinant secoisolariciresinol dehydrogenase, and methods of use |
| 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 |
| AU2003233473A1 (en) * | 2002-04-02 | 2003-10-20 | 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. |
| WO2012021983A1 (en) * | 2010-08-20 | 2012-02-23 | Fédération Des Producteurs Acéricoles Du Québec | 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 |
| JP6321788B2 (ja) | 2013-06-10 | 2018-05-09 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | （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 |
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2014
- 2014-06-10 JP JP2016519582A patent/JP6321788B2/ja not_active Expired - Fee Related
- 2014-06-10 EP EP14811683.3A patent/EP3007557B1/en active Active
- 2014-06-10 ES ES14811683.3T patent/ES2691845T3/es active Active
- 2014-06-10 WO PCT/US2014/041636 patent/WO2014200964A1/en not_active Ceased
- 2014-06-10 KR KR1020167000483A patent/KR102270124B1/ko active Active
- 2014-06-10 CN CN201711326022.7A patent/CN107955046A/zh active Pending
- 2014-06-10 DK DK14811683.3T patent/DK3007557T3/en active
- 2014-06-10 LT LTEP14811683.3T patent/LT3007557T/lt unknown
- 2014-06-10 TR TR2018/15423T patent/TR201815423T4/tr unknown
- 2014-06-10 HU HUE14811683A patent/HUE040022T2/hu unknown
- 2014-06-10 RS RS20181236A patent/RS57846B1/sr unknown
- 2014-06-10 SM SM20180575T patent/SMT201800575T1/it unknown
- 2014-06-10 CA CA2920346A patent/CA2920346A1/en not_active Abandoned
- 2014-06-10 AU AU2014278362A patent/AU2014278362B2/en not_active Ceased
- 2014-06-10 EP EP18183923.4A patent/EP3488697A1/en not_active Withdrawn
- 2014-06-10 SI SI201430924T patent/SI3007557T1/sl unknown
- 2014-06-10 PL PL14811683T patent/PL3007557T3/pl unknown
- 2014-06-10 US US14/897,181 patent/US10030040B2/en active Active
- 2014-06-10 HR HRP20181663TT patent/HRP20181663T1/hr unknown
- 2014-06-10 CN CN201480041131.2A patent/CN105705018B/zh active Active
- 2014-06-10 PT PT14811683T patent/PT3007557T/pt unknown
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2015
- 2015-12-10 IL IL243029A patent/IL243029B/en active IP Right Grant
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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
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2019
- 2019-04-10 JP JP2019074548A patent/JP6785335B2/ja active Active
- 2019-09-24 IL IL26962219A patent/IL269622A/en unknown