AR083589A1 - Un metodo para la produccion de acido-2,4-dihidroxibutirico - Google Patents
Un metodo para la produccion de acido-2,4-dihidroxibutiricoInfo
- Publication number
- AR083589A1 AR083589A1 ARP110103991A ARP110103991A AR083589A1 AR 083589 A1 AR083589 A1 AR 083589A1 AR P110103991 A ARP110103991 A AR P110103991A AR P110103991 A ARP110103991 A AR P110103991A AR 083589 A1 AR083589 A1 AR 083589A1
- Authority
- AR
- Argentina
- Prior art keywords
- malate
- dhb
- kinase
- semialdehyde
- dehydrogenase
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 229940049920 malate Drugs 0.000 abstract 8
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 7
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-Dihydroxybenzaldehyde Natural products OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 abstract 3
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 abstract 3
- 108091000080 Phosphotransferase Proteins 0.000 abstract 3
- 230000035772 mutation Effects 0.000 abstract 3
- 102000020233 phosphotransferase Human genes 0.000 abstract 3
- 101710138112 1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate dehydrogenase Proteins 0.000 abstract 2
- 244000005700 microbiome Species 0.000 abstract 2
- 230000001131 transforming effect Effects 0.000 abstract 2
- UFYGCFHQAXXBCF-UHFFFAOYSA-N 2,4-dihydroxybutanoic acid Chemical compound OCCC(O)C(O)=O UFYGCFHQAXXBCF-UHFFFAOYSA-N 0.000 abstract 1
- 101710088194 Dehydrogenase Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 102000001253 Protein Kinase Human genes 0.000 abstract 1
- 238000012258 culturing Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000013604 expression vector Substances 0.000 abstract 1
- 102000039446 nucleic acids Human genes 0.000 abstract 1
- 108020004707 nucleic acids Proteins 0.000 abstract 1
- 150000007523 nucleic acids Chemical class 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 108060006633 protein kinase Proteins 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
- C07F9/096—Compounds containing the structure P(=O)-O-C(=X)- (X = O, S, Se)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
- C12N15/52—Genes encoding for enzymes or proenzymes
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
- C12N15/70—Vectors or expression systems specially adapted for E. coli
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0008—Oxidoreductases (1.) acting on the aldehyde or oxo group of donors (1.2)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
- C12N9/1217—Phosphotransferases with a carboxyl group as acceptor (2.7.2)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y102/00—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2)
- C12Y102/01—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2) with NAD+ or NADP+ as acceptor (1.2.1)
- C12Y102/01011—Aspartate-semialdehyde dehydrogenase (1.2.1.11)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y102/00—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2)
- C12Y102/01—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2) with NAD+ or NADP+ as acceptor (1.2.1)
- C12Y102/01018—Malonate-semialdehyde dehydrogenase (acetylating) (1.2.1.18)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y207/00—Transferases transferring phosphorus-containing groups (2.7)
- C12Y207/02—Phosphotransferases with a carboxy group as acceptor (2.7.2)
- C12Y207/02004—Aspartate kinase (2.7.2.4)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y101/00—Oxidoreductases acting on the CH-OH group of donors (1.1)
- C12Y101/01—Oxidoreductases acting on the CH-OH group of donors (1.1) with NAD+ or NADP+ as acceptor (1.1.1)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Biophysics (AREA)
- Plant Pathology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
Un ácido nucleico que codifica una malato-cinasa tal como la divulgada, un vector de expresión, un microorganismo anfitrión.Reivindicación 1: Un método para producir ácido 2,4-dihidroxibutírico (2,4-DHB) que comprende lo siguiente: un primer paso que consiste en transformar malato en 4-fosfomalato mediante una malato-cinasa; un segundo paso que consiste en transformar 4-fosfo-malato en malato-4-semialdehído mediante una malatosemialdehído deshidrogenada; un tercer paso que consiste en transformar malato-4-semialdehído en 2,4-DHB mediante una DHB deshidrogenasa. Reivindicación 16: La malato-cinasa de acuerdo con la reivindicación 15 que se puede obtener mediante, al menos, una mutación de una enzima; dicha mutación o mutaciones mejoran la actividad y/o afinidad del sustrato del polipéptido mutado por malato. Reivindicación 47: Un proceso para producir 2,4-DHB que comprende el paso que consiste en cultivar un microorganismo anfitrión de acuerdo con una cualquiera de las reivindicaciones 42 a 46 que expresa una malato-cinasa, una malato-semialdehído deshidrogenasa y una DHB deshidrogenasa.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IBPCT/IB10/03153 | 2010-10-28 | ||
IBPCT/IB11/01559 | 2011-05-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR083589A1 true AR083589A1 (es) | 2013-03-06 |
Family
ID=45464014
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP110103991A AR083589A1 (es) | 2010-10-28 | 2011-10-28 | Un metodo para la produccion de acido-2,4-dihidroxibutirico |
Country Status (11)
Country | Link |
---|---|
US (2) | US9238829B2 (es) |
EP (1) | EP2633038B1 (es) |
JP (2) | JP6071887B2 (es) |
KR (1) | KR101990014B1 (es) |
CN (2) | CN105505892B (es) |
AR (1) | AR083589A1 (es) |
BR (1) | BR112013010268B1 (es) |
ES (1) | ES2631554T3 (es) |
RU (1) | RU2626531C2 (es) |
TW (1) | TWI626311B (es) |
WO (1) | WO2012056318A1 (es) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2633038B1 (en) * | 2010-10-28 | 2017-04-05 | Adisseo France S.A.S. | A method of production of 2,4-dihydrobutyric acid |
JP6342385B2 (ja) | 2012-04-26 | 2018-06-13 | アディッソ・フランス・エス.エー.エス.Adisseo France S.A.S. | 2,4−ジヒドロキシ酪酸を生成する方法 |
CN104685058B (zh) | 2012-06-04 | 2020-07-07 | 基因组股份公司 | 制造4-羟基丁酸酯、1,4-丁二醇和相关化合物的微生物和方法 |
JP6293746B2 (ja) | 2012-07-11 | 2018-03-14 | アディセオ・フランセ・エス・アー・エス | 2,4−ジヒドロキシ酪酸塩の調製のための方法 |
US9605283B2 (en) | 2012-07-11 | 2017-03-28 | Institut National Des Sciences Appliquées | Microorganism modified for the production of 1,3-propanediol |
CN102864196B (zh) * | 2012-10-09 | 2014-07-02 | 南京工业大学 | 一种二氢乳清酸酶法制备α-天冬氨酰小肽的方法 |
CN103773745B (zh) * | 2012-10-18 | 2018-03-23 | 中粮生物化学(安徽)股份有限公司 | 天冬氨酸激酶iii突变体及其宿主细胞和应用 |
JP2016165225A (ja) * | 2013-07-09 | 2016-09-15 | 味の素株式会社 | 有用物質の製造方法 |
CN107690482B (zh) | 2015-04-07 | 2022-11-29 | 代谢探索者公司 | 用于2,4-二羟基丁酸的优化生产的经修饰的微生物 |
ES2811337T3 (es) * | 2015-04-07 | 2021-03-11 | Metabolic Explorer Sa | Microorganismo modificado para la producción optimizada de 2,4-dihidroxibutirato con eflujo de 2,4- dihidroxibutirato aumentado |
CA2989434C (en) | 2015-06-25 | 2023-10-03 | Dynamic Food Ingredients Corporation | Method for the production of 2,4-dihydroxybutyric acid |
CN108624627B (zh) * | 2017-03-22 | 2021-07-30 | 中国科学院天津工业生物技术研究所 | 催化甲酸合成甲醛酶的制备及其应用 |
JPWO2021162099A1 (es) * | 2020-02-14 | 2021-08-19 | ||
CN112322597B (zh) * | 2020-11-23 | 2022-08-23 | 天津法莫西生物医药科技有限公司 | 一种羰基还原酶突变体及其应用 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07155184A (ja) * | 1993-12-08 | 1995-06-20 | Ajinomoto Co Inc | 発酵法によるl−リジンの製造法 |
JP4088982B2 (ja) | 1996-10-15 | 2008-05-21 | 味の素株式会社 | 発酵法によるl−アミノ酸の製造法 |
DE10014546A1 (de) * | 2000-03-23 | 2001-09-27 | Degussa | Für das dapC-Gen kodierende Nukleotidsequenzen und Verfahren zur Herstellung von L-Lysin |
CN101208427A (zh) * | 2003-05-30 | 2008-06-25 | 米克罗比亚股份有限公司 | 氨基酸制备的方法和组合物 |
RU2275424C2 (ru) * | 2003-12-05 | 2006-04-27 | Закрытое акционерное общество "Научно-исследовательский институт Аджиномото-Генетика" (ЗАО АГРИ) | Способ получения l-треонина с использованием бактерий, принадлежащих к роду escherichia |
DE102006017760A1 (de) * | 2006-03-24 | 2007-09-27 | Ufz-Umweltforschungszentrum Leipzig-Halle Gmbh | Verfahren zur enzymatischen Herstellung von 2-Hydroxy-2-methylcarbonsäuren |
KR100837842B1 (ko) * | 2006-08-10 | 2008-06-13 | 씨제이제일제당 (주) | 아스파테이트 세미알데히드 디하이드로게나아제 활성이증가된 l-쓰레오닌 생산 미생물 및 이를 이용한l-쓰레오닌 생산 방법 |
EP3214179B1 (en) * | 2007-03-16 | 2021-03-03 | Genomatica, Inc. | Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors |
BRPI0914521A2 (pt) * | 2008-10-27 | 2016-07-26 | Butamax Advanced Biofuels Llc | célula hospedeira microbiana recombinante, método de aumento da produção de isobutanol e método de produção de isobutanol |
EP2633038B1 (en) * | 2010-10-28 | 2017-04-05 | Adisseo France S.A.S. | A method of production of 2,4-dihydrobutyric acid |
-
2011
- 2011-10-27 EP EP11805587.0A patent/EP2633038B1/en active Active
- 2011-10-27 US US13/882,372 patent/US9238829B2/en active Active
- 2011-10-27 CN CN201610007101.0A patent/CN105505892B/zh active Active
- 2011-10-27 BR BR112013010268-3A patent/BR112013010268B1/pt active IP Right Grant
- 2011-10-27 WO PCT/IB2011/002870 patent/WO2012056318A1/en active Application Filing
- 2011-10-27 RU RU2013123481A patent/RU2626531C2/ru active
- 2011-10-27 ES ES11805587.0T patent/ES2631554T3/es active Active
- 2011-10-27 JP JP2013535529A patent/JP6071887B2/ja active Active
- 2011-10-27 KR KR1020137012492A patent/KR101990014B1/ko active IP Right Grant
- 2011-10-27 CN CN201180052237.9A patent/CN103270155B/zh active Active
- 2011-10-28 TW TW100139345A patent/TWI626311B/zh active
- 2011-10-28 AR ARP110103991A patent/AR083589A1/es active IP Right Grant
-
2015
- 2015-11-18 US US14/945,046 patent/US10358663B2/en active Active
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2016
- 2016-11-01 JP JP2016214205A patent/JP6345747B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
WO2012056318A1 (en) | 2012-05-03 |
JP6071887B2 (ja) | 2017-02-01 |
CN103270155B (zh) | 2016-02-10 |
JP2017070285A (ja) | 2017-04-13 |
RU2626531C2 (ru) | 2017-07-28 |
RU2013123481A (ru) | 2014-12-10 |
TWI626311B (zh) | 2018-06-11 |
EP2633038A1 (en) | 2013-09-04 |
TW201221648A (en) | 2012-06-01 |
US9238829B2 (en) | 2016-01-19 |
ES2631554T3 (es) | 2017-09-01 |
US20130273623A1 (en) | 2013-10-17 |
JP2013543727A (ja) | 2013-12-09 |
CN105505892A (zh) | 2016-04-20 |
CN105505892B (zh) | 2019-03-26 |
KR20140091463A (ko) | 2014-07-21 |
CN103270155A (zh) | 2013-08-28 |
KR101990014B1 (ko) | 2019-06-17 |
BR112013010268A2 (pt) | 2016-07-05 |
EP2633038B1 (en) | 2017-04-05 |
BR112013010268B1 (pt) | 2020-09-08 |
US10358663B2 (en) | 2019-07-23 |
US20160153013A1 (en) | 2016-06-02 |
JP6345747B2 (ja) | 2018-06-20 |
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