LT6013B - Ypatingai gryno dihidrokvercetino gamybos būdas - Google Patents

Ypatingai gryno dihidrokvercetino gamybos būdas Download PDF

Info

Publication number: LT6013B
Authority: LT; Lithuania
Prior art keywords: eluate; product; dihydroquercetin; sorbent; solution
Prior art date: 2012-05-18

Application number

LT2012035A

Other languages

English (en)

Lithuanian (lt)

Other versions

LT2012035A (lt

Inventor

Natalia Kiseliova

Yury Garipov

Sergey Ponkratov

Viačeslavas MASLOVAS

Original Assignee

Uab "Rokiå Kio Pragiedruliai"

Priority date (The priority date 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 date listed.)

2012-05-18

Filing date

2012-05-18

Publication date

2014-03-25

2012-05-18 Application filed by Uab "Rokiå Kio Pragiedruliai" filed Critical Uab "Rokiå Kio Pragiedruliai"

2012-05-18 Priority to LT2012035A priority Critical patent/LT6013B/lt

2012-11-21 Priority to PCT/LT2012/000008 priority patent/WO2013172693A1/fr

2012-11-21 Priority to EP12806719.6A priority patent/EP2850069A1/fr

2013-11-25 Publication of LT2012035A publication Critical patent/LT2012035A/lt

2014-03-25 Publication of LT6013B publication Critical patent/LT6013B/lt

Links

CXQWRCVTCMQVQX-LSDHHAIUSA-N (+)-taxifolin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-LSDHHAIUSA-N 0.000 title abstract description 32
XCGZWJIXHMSSQC-UHFFFAOYSA-N dihydroquercetin Natural products OC1=CC2OC(=C(O)C(=O)C2C(O)=C1)c1ccc(O)c(O)c1 XCGZWJIXHMSSQC-UHFFFAOYSA-N 0.000 title abstract description 12
238000004519 manufacturing process Methods 0.000 title abstract description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
238000000034 method Methods 0.000 claims abstract description 28
239000002594 sorbent Substances 0.000 claims abstract description 22
239000000243 solution Substances 0.000 claims abstract description 20
239000007864 aqueous solution Substances 0.000 claims abstract description 9
238000002425 crystallisation Methods 0.000 claims abstract description 6
230000008025 crystallization Effects 0.000 claims abstract description 6
238000004949 mass spectrometry Methods 0.000 claims abstract description 5
238000004587 chromatography analysis Methods 0.000 claims abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
235000019441 ethanol Nutrition 0.000 claims description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
239000002245 particle Substances 0.000 claims description 8
239000011148 porous material Substances 0.000 claims description 8
238000004108 freeze drying Methods 0.000 claims description 6
230000014759 maintenance of location Effects 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
230000002441 reversible effect Effects 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
239000000047 product Substances 0.000 abstract description 33
238000001914 filtration Methods 0.000 abstract description 8
238000013375 chromatographic separation Methods 0.000 abstract description 6
239000002994 raw material Substances 0.000 abstract description 5
238000002955 isolation Methods 0.000 abstract description 3
239000002537 cosmetic Substances 0.000 abstract description 2
238000004090 dissolution Methods 0.000 abstract description 2
235000013305 food Nutrition 0.000 abstract description 2
239000013589 supplement Substances 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 4
230000003078 antioxidant effect Effects 0.000 description 4
239000011121 hardwood Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000012986 modification Methods 0.000 description 4
230000004048 modification Effects 0.000 description 4
PADQINQHPQKXNL-LSDHHAIUSA-N (+)-dihydrokaempferol Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C=C1 PADQINQHPQKXNL-LSDHHAIUSA-N 0.000 description 3
FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
RTIXKCRFFJGDFG-UHFFFAOYSA-N Chrysin Natural products C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
FGUBFGWYEYFGRK-HNNXBMFYSA-N Pinocembrin Natural products Cc1cc(C)c2C(=O)C[C@H](Oc2c1)c3ccccc3 FGUBFGWYEYFGRK-HNNXBMFYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
UIDUJXXQMGYOIN-UHFFFAOYSA-N aromadendrin Natural products CC1(C)C2C1CCC(C)C1C2C(C)CC1 UIDUJXXQMGYOIN-UHFFFAOYSA-N 0.000 description 3
238000007872 degassing Methods 0.000 description 3
KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 3
RAYJUFCFJUVJBB-UHFFFAOYSA-N dihydrokaempferol Natural products OC1Oc2c(O)cc(O)cc2C(=O)C1c3ccc(O)cc3 RAYJUFCFJUVJBB-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229930003935 flavonoid Natural products 0.000 description 3
-1 flavonoid compounds Chemical class 0.000 description 3
235000017173 flavonoids Nutrition 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 3
WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 description 3
229940117954 naringenin Drugs 0.000 description 3
235000007625 naringenin Nutrition 0.000 description 3
URFCJEUYXNAHFI-ZDUSSCGKSA-N pinocembrin Chemical compound C1([C@@H]2CC(=O)C3=C(O)C=C(C=C3O2)O)=CC=CC=C1 URFCJEUYXNAHFI-ZDUSSCGKSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229960001285 quercetin Drugs 0.000 description 3
IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 2
HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
235000005875 quercetin Nutrition 0.000 description 2
JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 description 1
238000007445 Chromatographic isolation Methods 0.000 description 1
229920001991 Proanthocyanidin Polymers 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229940093797 bioflavonoids Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229920002770 condensed tannin Polymers 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000003809 water extraction Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Steroid Compounds (AREA)

LT2012035A 2012-05-18 2012-05-18 Ypatingai gryno dihidrokvercetino gamybos būdas LT6013B (lt)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
LT2012035A LT6013B (lt)	2012-05-18	2012-05-18	Ypatingai gryno dihidrokvercetino gamybos būdas
PCT/LT2012/000008 WO2013172693A1 (fr)	2012-05-18	2012-11-21	Procédé de préparation de dihydroquercétine de pureté élevée
EP12806719.6A EP2850069A1 (fr)	2012-05-18	2012-11-21	Procédé de préparation de dihydroquercétine de pureté élevée

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LT2012035A LT6013B (lt)	2012-05-18	2012-05-18	Ypatingai gryno dihidrokvercetino gamybos būdas

Publications (2)

Publication Number	Publication Date
LT2012035A LT2012035A (lt)	2013-11-25
LT6013B true LT6013B (lt)	2014-03-25

Family

ID=47436155

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LT2012035A LT6013B (lt)	2012-05-18	2012-05-18	Ypatingai gryno dihidrokvercetino gamybos būdas

Country Status (3)

Country	Link
EP (1)	EP2850069A1 (fr)
LT (1)	LT6013B (fr)
WO (1)	WO2013172693A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108623548B (zh) *	2018-05-02	2022-05-06	齐齐哈尔大学	一种分离花生壳中手型圣草酚的方法及其应用
CN113214210B (zh) *	2021-05-10	2022-03-04	合肥立方制药股份有限公司	一种二氢槲皮素的制备方法
CN113185485B (zh)	2021-05-10	2022-03-04	合肥立方制药股份有限公司	一种二氢槲皮素的半合成方法
CN114774490B (zh) *	2022-04-19	2025-01-28	沈阳市丽晨生物医药科技有限公司	用于抗癌抗氧化抗心脑血管疾病的二氢槲皮素制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2000797C1 (ru)	1992-05-26	1993-10-15	Отдел химии древесины Иркутского института органической химии СО РАН	Способ выделени дигидрокверцетина
RU2038094C1 (ru)	1994-02-08	1995-06-27	Товарищество с ограниченной ответственностью "Инкор"	Способ получения дигидрокверцетина
RU2114631C1 (ru)	1997-07-22	1998-07-10	Нонна Арсеньевна Тюкавкина	Способ выделения дигидрокверцетина
RU2186097C1 (ru)	2001-07-06	2002-07-27	Общество с ограниченной ответственностью "Сибларекс"	Состав биофлавоноидного комплекса сибел для пищевых и парфюмерных изделий и способ получения биофлавоноидного комплекса сибел для пищевых и парфюмерных изделий
US7132296B2 (en)	2002-02-15	2006-11-07	Medical Products Manufacturing, Llc	Method for assaying the antioxidant capacity of a sample

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5912363A (en)	1997-08-29	1999-06-15	Interhealth Nutraceuticals	Method for extraction of proanthocyanidins from plant material

2012
- 2012-05-18 LT LT2012035A patent/LT6013B/lt not_active IP Right Cessation
- 2012-11-21 EP EP12806719.6A patent/EP2850069A1/fr not_active Withdrawn
- 2012-11-21 WO PCT/LT2012/000008 patent/WO2013172693A1/fr not_active Ceased

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2000797C1 (ru)	1992-05-26	1993-10-15	Отдел химии древесины Иркутского института органической химии СО РАН	Способ выделени дигидрокверцетина
RU2038094C1 (ru)	1994-02-08	1995-06-27	Товарищество с ограниченной ответственностью "Инкор"	Способ получения дигидрокверцетина
RU2114631C1 (ru)	1997-07-22	1998-07-10	Нонна Арсеньевна Тюкавкина	Способ выделения дигидрокверцетина
RU2186097C1 (ru)	2001-07-06	2002-07-27	Общество с ограниченной ответственностью "Сибларекс"	Состав биофлавоноидного комплекса сибел для пищевых и парфюмерных изделий и способ получения биофлавоноидного комплекса сибел для пищевых и парфюмерных изделий
US7132296B2 (en)	2002-02-15	2006-11-07	Medical Products Manufacturing, Llc	Method for assaying the antioxidant capacity of a sample

Also Published As

Publication number	Publication date
WO2013172693A1 (fr)	2013-11-21
LT2012035A (lt)	2013-11-25
EP2850069A1 (fr)	2015-03-25

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Wang et al.	2014	Determination of phenolic acids and flavonoids in raw propolis by silica-supported ionic liquid-based matrix solid phase dispersion extraction high performance liquid chromatography-diode array detection
Liu et al.	2012	Extraction and characterization of proanthocyanidins from grape seeds
JP2009035550A (ja)	2009-02-19	プロアントシアニジンの豊富な抽出物、及び関連する調製方法
EP2212004B1 (fr)	2015-05-13	Procédé de récupération de composés bioactifs
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US6264853B1 (en)	2001-07-24	Complex containing lignan, phenolic and aliphatic substances from flax and process for preparing
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LT6013B (lt)	2014-03-25	Ypatingai gryno dihidrokvercetino gamybos būdas
CN105601606B (zh)	2017-11-21	一种制备高纯度没食子儿茶素没食子酸酯gcg的方法
US20130237712A1 (en)	2013-09-12	Method for isolating flavonoid dihydroquercetin (taxifolin) from conifer wood species
RU2593014C2 (ru)	2016-07-27	Способ производства проантоцианидиновой полимерной композиции
JP2010260823A (ja)	2010-11-18	プロアントシアニジンの分離精製方法
CN112175028B (zh)	2021-09-21	一种分离制备飞燕草素-3-o-(6-o-对香豆酰)葡萄糖苷的方法
RU2308267C1 (ru)	2007-10-20	Способ выделения биологически активных изомеров дигидрокверцетина
RU2349331C1 (ru)	2009-03-20	Способ получения дигидрокверцетина
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CN106187975B (zh)	2018-02-13	一种提高米糠酚类物质生物活性的制备及纯化方法
RU2114631C1 (ru)	1998-07-10	Способ выделения дигидрокверцетина
Li et al.	2019	Evaluation of the Antioxidative and Anti-inflammatory Effects of the Extract of Ribes mandshuricum (Maxim.) Kom. Leaves.
CN105646429B (zh)	2018-06-19	一种制备高纯度儿茶素没食子酸酯cg的方法
JPS63267774A (ja)	1988-11-04	プロアントシアニジンの製造法
CN102617535B (zh)	2014-08-20	从杨梅叶中提取原飞燕草素的方法
RU2317093C1 (ru)	2008-02-20	Способ выделения биологически активных изомеров дигидрокверцетина
CN112300233B (zh)	2021-12-07	一种芍药素-3-o-(6-o-对香豆酰)葡萄糖苷-5-葡萄糖苷的分离制备方法
CN112321655B (zh)	2021-12-07	一种分离制备矮牵牛素-3-o-(6-o-对香豆酰)葡萄糖苷的方法

Legal Events

Date	Code	Title	Description
2013-11-25	BB1A	Patent application published	Effective date: 20131125
2014-03-25	FG9A	Patent granted	Effective date: 20140325
2017-12-11	MM9A	Lapsed patents	Effective date: 20170518