HRP20221360T1 - Proizvodnja nezasićenih masnih alkohola i nezasićenih masnih acil-acetata uz pomoć kvasca - Google Patents
Proizvodnja nezasićenih masnih alkohola i nezasićenih masnih acil-acetata uz pomoć kvasca Download PDFInfo
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- HRP20221360T1 HRP20221360T1 HRP20221360TT HRP20221360T HRP20221360T1 HR P20221360 T1 HRP20221360 T1 HR P20221360T1 HR P20221360T T HRP20221360T T HR P20221360TT HR P20221360 T HRP20221360 T HR P20221360T HR P20221360 T1 HRP20221360 T1 HR P20221360T1
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- yeast cell
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- unsaturated fatty
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- fatty alcohol
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- 150000002191 fatty alcohols Chemical class 0.000 title claims 13
- 240000004808 Saccharomyces cerevisiae Species 0.000 title claims 6
- -1 fatty acyl acetates Chemical class 0.000 title claims 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 210000005253 yeast cell Anatomy 0.000 claims 27
- 102000005970 fatty acyl-CoA reductase Human genes 0.000 claims 15
- 108090001018 hexadecanal dehydrogenase (acylating) Proteins 0.000 claims 15
- 230000035772 mutation Effects 0.000 claims 10
- 150000002185 fatty acyl-CoAs Chemical class 0.000 claims 9
- 102000005421 acetyltransferase Human genes 0.000 claims 7
- 108020002494 acetyltransferase Proteins 0.000 claims 7
- 108010087894 Fatty acid desaturases Proteins 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 102100034543 Fatty acid desaturase 3 Human genes 0.000 claims 4
- 102000005488 Thioesterase Human genes 0.000 claims 4
- 241000235015 Yarrowia lipolytica Species 0.000 claims 4
- DUAFKXOFBZQTQE-QSGBVPJFSA-N myristoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 DUAFKXOFBZQTQE-QSGBVPJFSA-N 0.000 claims 4
- 108020002982 thioesterase Proteins 0.000 claims 4
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims 3
- 101150078221 fas2 gene Proteins 0.000 claims 3
- 150000002190 fatty acyls Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 241000255601 Drosophila melanogaster Species 0.000 claims 2
- 102000009114 Fatty acid desaturases Human genes 0.000 claims 2
- 102100022366 Fatty acyl-CoA reductase 1 Human genes 0.000 claims 2
- 241001149698 Lipomyces Species 0.000 claims 2
- 241000223252 Rhodotorula Species 0.000 claims 2
- 241000235070 Saccharomyces Species 0.000 claims 2
- 241000235013 Yarrowia Species 0.000 claims 2
- 150000002399 hexadecanoyl-CoAs Chemical class 0.000 claims 2
- MNBKLUUYKPBKDU-BBECNAHFSA-N palmitoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MNBKLUUYKPBKDU-BBECNAHFSA-N 0.000 claims 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 1
- 102100022089 Acyl-[acyl-carrier-protein] hydrolase Human genes 0.000 claims 1
- 241000143517 Bicyclus anynana Species 0.000 claims 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
- 241000723346 Cinnamomum camphora Species 0.000 claims 1
- 241001527609 Cryptococcus Species 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- 108010039731 Fatty Acid Synthases Proteins 0.000 claims 1
- 241001147381 Helicoverpa armigera Species 0.000 claims 1
- 241000510199 Helicoverpa assulta Species 0.000 claims 1
- 241001515776 Heliothis subflexa Species 0.000 claims 1
- 241000235649 Kluyveromyces Species 0.000 claims 1
- 235000014663 Kluyveromyces fragilis Nutrition 0.000 claims 1
- 241000235058 Komagataella pastoris Species 0.000 claims 1
- 241001149691 Lipomyces starkeyi Species 0.000 claims 1
- 241001443590 Naganishia albida Species 0.000 claims 1
- 241000235648 Pichia Species 0.000 claims 1
- 241000223253 Rhodotorula glutinis Species 0.000 claims 1
- 241000221523 Rhodotorula toruloides Species 0.000 claims 1
- 244000253911 Saccharomyces fragilis Species 0.000 claims 1
- 235000018368 Saccharomyces fragilis Nutrition 0.000 claims 1
- 241001634922 Tausonia pullulans Species 0.000 claims 1
- 241000223230 Trichosporon Species 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229940031154 kluyveromyces marxianus Drugs 0.000 claims 1
- 239000003016 pheromone Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
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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
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
-
- 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
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/16—Yeasts; Culture media therefor
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- 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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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/001—Oxidoreductases (1.) acting on the CH-CH group of donors (1.3)
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- 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.)
- C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y103/00—Oxidoreductases acting on the CH-CH group of donors (1.3)
- C12Y103/01—Oxidoreductases acting on the CH-CH group of donors (1.3) with NAD+ or NADP+ as acceptor (1.3.1)
- C12Y103/01086—Crotonyl-CoA reductase (1.3.1.86)
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
- C12Y114/19—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with oxidation of a pair of donors resulting in the reduction of molecular oxygen to two molecules of water (1.14.19)
- C12Y114/19001—Stearoyl-CoA 9-desaturase (1.14.19.1), i.e. DELTA9-desaturase
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Virology (AREA)
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Claims (12)
1. Stanica kvasca, koja može proizvoditi nezasićeni masni alkohol i izborno acetat nezasićenog masnog alkohola, gdje navedena stanica kvasca eksprimira:
i) najmanje jednu heterolognu desaturazu masnog acil-CoA, koja može uvoditi najmanje jednu dvostruku vezu u masni acil-CoA koji ima duljinu ugljičnog lanca od 14, pri čemu je navedena desaturaza Δ9 desaturaza, koja je najmanje 80 % homologna Δ9 desaturazi iz vinske mušice Drosophila melanogaster, kao što je iznijeto u SEQ ID NO: 10 i ima veću specifičnost prema tetradekanoil-CoA nego prema heksadekanoil-CoA; i
ii) najmanje jednu heterolognu reduktazu masnog acila-CoA (FAR) (EC 1.2.1.84), koja može pretvarati barem dio navedenog nezasićenog masnog acil-CoA u nezasićeni masni alkohol, izborno pri čemu FAR ima veću specifičnost prema nezasićenom tetradekanoil-CoA nego prema nezasićenom heksadekanoil-CoA; i
iii) izborno acetil-transferazu (EC 2.3.1.84), koja može pretvarati barem dio navedenog nezasićenog masnog alkohola u acetat nezasićenog masnog alkohola.
2. Stanica kvasca u skladu s patentnim zahtjevom 1, pri čemu se reduktaza masnog acila-CoA (FAR) bira između:
i) FAR koji je najmanje 80 % homologan FAR iz moljca Helicoverpa armigera, kao što je iznijeto u SEQ ID NO: 25 ili SEQ ID NO: 27;
ii) FAR koji je najmanje 80 % homologan FAR iz moljca Helicoverpa assulta, kao što je iznijeto u SEQ ID NO: 29 ili SEQ ID NO: 31;
iii) FAR koji je najmanje 80 % homologan FAR iz moljca Heliothis subflexa, kao što je iznijeto u SEQ ID NO: 33 ili SEQ ID NO: 35; i
iv) FAR koji je najmanje 80 % homologan FAR iz leptira Bicyclus anynana, kao što je iznijeto u SEQ ID NO: 45.
3. Stanica kvasca u skladu s bilo kojim od prethodnih patentnih zahtjeva, pri čemu je acetil-transferaza heterologna acetil-transferaza koju eksprimira navedena stanica kvasca ili nativna acetil-transferaza koju hipereksprimira navedena stanica kvasca, gdje je po mogućnosti acetil-transferaza najmanje 75 % homologna acetil-transferazi Atf1 iz kvasca Saccharomyces cerevisiae, kao što je iznijeto u SEQ ID NO: 21.
4. Stanica kvasca u skladu s bilo kojim od prethodnih patentnih zahtjeva, pri čemu kvasac pripada rodu kojeg se bira između rodova Saccharomyces, Pichia, Yarrowia, Kluyveromyces, Candida, Rhodotorula, Rhodosporidium, Cryptococcus, Trichosporon i Lipomyces, po mogućnosti rodu Saccharomyces ili Yarrowia, gdje po mogućnosti kvasac pripada vrsti koju se bira između vrsta Saccharomyces cerevisiae, Pichia pastoris, Kluyveromyces marxianus, Cryptococcus albidus, Lipomyces lipofera, Lipomyces starkeyi, Rhodosporidium toruloides, Rhodotorula glutinis, Trichosporon pullulan i Yarrowia lipolytica, gdje je po mogućnosti stanica kvasca stanica kvasca Saccharomyces cerevisiae ili stanica kvasca Yarrowia lipolytica, gdje je najpoželjnije stanica kvasca stanica kvasca Yarrowia lipolytica.
5. Stanica kvasca u skladu s bilo kojim od prethodnih patentnih zahtjeva, pri čemu stanica kvasca dodatno eksprimira ili hipereksprimira tioesterazu, gdje je po mogućnosti tioesteraza najmanje 60 % homologna tioesterazi iz kamforovca Cinnamomum camphora, kao što je iznijeto u SEQ ID NO: 40, ili tioesterazi iz bakterije Escherichia coli, kao što je iznijeto u SEQ ID NO: 42.
6. Stanica kvasca u skladu s bilo kojim od prethodnih patentnih zahtjeva, pri čemu stanica kvasca dodatno eksprimira varijantu sintaze masnog acila koja ima modificiranu keton-sintaznu domenu, zbog čega stanica kvasca sintetizira veći udio C14 masnih acil-CoA nego stanica kvasca koja eksprimira nativnu masni acil-sintazu u istim uvjetima.
7. Stanica kvasca u skladu s patentnim zahtjevom 6, pri čemu je stanica kvasca stanica kvasca Yarrowia lipolytica, te pri čemu je varijanta sintaze masnog acila sintaza masne kiseline koja sadrži mutaciju u genu FAS2, kao što je iznijeto u SEQ ID NO: 71, po mogućnosti pri čemu je mutacija u genu FAS2 mutacija na položaju 1220, 1217 ili 1226 u genu FAS2, kao što je iznijeto u SEQ ID NO: 71, poput mutacije I1220F, mutacije I1220Y, mutacije I1220H i/ili mutacije M1217F, mutacije M1217W, mutacije M1217Y ili mutacije M1217H.
8. Postupak proizvodnje nezasićenog masnog alkohola i izborno acetata nezasićenog masnog alkohola u stanici kvasca, gdje se navedeni postupak sastoji od koraka osiguravanja stanice kvasca i inkubiranja navedene stanice kvasca u mediju, pri čemu stanica kvasca eksprimira:
i) najmanje jednu heterolognu desaturazu masnog acil-CoA, koja može uvoditi najmanje jednu dvostruku vezu u masni acil-CoA koji ima duljinu ugljičnog lanca od 14, pri čemu je navedena desaturaza Δ9 desaturaza, koja je najmanje 80% homologna Δ9 desaturazi iz vinske mušice Drosophila melanogaster, kao što je iznijeto u SEQ ID NO: 10 i ima veću specifičnost prema tetradekanoil-CoA nego prema heksadekanoil-CoA, zbog čega pretvara barem dio navedenog masnog acil-CoA u nezasićeni masni acil-CoA; i
ii) najmanje jednu heterolognu reduktazu masnog acila-CoA (EC 1.2.1.84), koja može pretvarati barem dio navedenog nezasićenog masnog acil-CoA u nezasićeni masni alkohol, izborno pri čemu FAR ima veću specifičnost prema nezasićenom tetradekanoil-CoA nego prema nezasićenom heksadekanoil-CoA, zbog čega proizvodi navedeni nezasićeni masni alkohol; i
iii) izborno acetil-transferazu (EC 2.3.1.84), koja može pretvarati barem dio navedenog nezasićenog masnog alkohola u acetat nezasićenog masnog alkohola, zbog čega proizvodi navedeni acetat nezasićenog masnog alkohola.
9. Postupak u skladu s patentnim zahtjevom 8, pri čemu je stanica kvasca u skladu s bilo kojim od patentnih zahtjeva 1 do 7.
10. Postupak u skladu s bilo kojim od patentnih zahtjeva 8 do 9, pri čemu se postupkom dobiva nezasićeni masni alkohol koji ima duljinu lanca od 14 s titrom od najmanje 1 mg/l, primjerice najmanje 1,5 mg/l, primjerice najmanje 5 mg/l, primjerice najmanje 10 mg/l, primjerice najmanje 25 mg/l, primjerice najmanje 50 mg/l, primjerice najmanje 100 mg/l, primjerice najmanje 250 mg/l, primjerice najmanje 500 mg/l, primjerice najmanje 750 mg/l, primjerice najmanje 1 g/l, primjerice najmanje 2 g/l, primjerice najmanje 3 g/l, primjerice najmanje 4 g/l, primjerice najmanje 5 g/l, ili više.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva 8 do 10, koji dodatno uključuje korak prikupljanja navedenog nezasićenog masnog alkohola i/ili acetata nezasićenog masnog alkohola i izborno dodatno uključuje korak formuliranja prikupljenog nezasićenog masnog alkohola i/ili acetata nezasićenog masnog alkohola u feromonski pripravak.
12. Komplet dijelova koji sadrži stanicu kvasca u skladu s bilo kojim od patentnih zahtjeva 1 do 7 i upute o uporabi.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16204783 | 2016-12-16 | ||
EP17825466.0A EP3555269B1 (en) | 2016-12-16 | 2017-12-15 | Production of desaturated fatty alcohols and desaturated fatty acyl acetates in yeast |
PCT/EP2017/083030 WO2018109167A1 (en) | 2016-12-16 | 2017-12-15 | Production of desaturated fatty alcohols and desaturated fatty acyl acetates in yeast |
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HRP20221360T1 true HRP20221360T1 (hr) | 2023-01-06 |
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HRP20221360TT HRP20221360T1 (hr) | 2016-12-16 | 2017-12-15 | Proizvodnja nezasićenih masnih alkohola i nezasićenih masnih acil-acetata uz pomoć kvasca |
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US (2) | US11434506B2 (hr) |
EP (2) | EP3555269B1 (hr) |
CN (1) | CN110291193B (hr) |
BR (1) | BR112019012276B1 (hr) |
DE (1) | DE17825466T1 (hr) |
DK (1) | DK3555269T3 (hr) |
ES (1) | ES2930358T3 (hr) |
HR (1) | HRP20221360T1 (hr) |
HU (1) | HUE060726T2 (hr) |
MX (2) | MX2019007048A (hr) |
PL (1) | PL3555269T3 (hr) |
RS (1) | RS63726B1 (hr) |
WO (1) | WO2018109167A1 (hr) |
ZA (1) | ZA201903482B (hr) |
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EP3868890A1 (en) | 2015-11-18 | 2021-08-25 | Provivi, Inc. | Microorganisms for the production of insect pheromones and related compounds |
JP7216018B2 (ja) | 2017-05-17 | 2023-01-31 | プロヴィヴィ インコーポレイテッド | 昆虫フェロモンの生成のための微生物及び関連する化合物 |
IL292002B2 (en) | 2019-10-22 | 2023-10-01 | Biophero Aps | Improved methods for the production, recovery and secretion of hydrophobic compounds in culture |
WO2021119548A1 (en) * | 2019-12-11 | 2021-06-17 | Provivi, Inc. | Biosynthesis of insect pheromones and precursors thereof |
IL293960A (en) * | 2019-12-20 | 2022-08-01 | Biophero Aps | Yeast cells and methods for the production of e10,e8-dodecadienyl coenzyme a, codelmon and its derivatives |
EP4337781A1 (en) | 2021-05-10 | 2024-03-20 | FMC Agricultural Solutions A/S | Improved methods and cells for increasing enzyme activity and production of insect pheromones |
CA3222768A1 (en) * | 2021-07-02 | 2023-01-05 | Carina HOLKENBRINK | Methods and yeast cells for production of desaturated compounds |
EP4363562A1 (en) | 2021-07-02 | 2024-05-08 | FMC Agricultural Solutions A/S | Methods and yeast cells for production of desaturated compounds |
MX2024001309A (es) | 2021-08-06 | 2024-05-17 | Fmc Agricultural Solutions As | Metodo para producir aldehidos grasos y derivados de los mismos. |
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2017
- 2017-12-15 CN CN201780086433.5A patent/CN110291193B/zh active Active
- 2017-12-15 DE DE17825466.0T patent/DE17825466T1/de active Pending
- 2017-12-15 RS RS20221038A patent/RS63726B1/sr unknown
- 2017-12-15 BR BR112019012276-1A patent/BR112019012276B1/pt active IP Right Grant
- 2017-12-15 DK DK17825466.0T patent/DK3555269T3/da active
- 2017-12-15 HU HUE17825466A patent/HUE060726T2/hu unknown
- 2017-12-15 US US16/468,784 patent/US11434506B2/en active Active
- 2017-12-15 EP EP17825466.0A patent/EP3555269B1/en active Active
- 2017-12-15 MX MX2019007048A patent/MX2019007048A/es unknown
- 2017-12-15 EP EP22192750.2A patent/EP4159850A1/en active Pending
- 2017-12-15 HR HRP20221360TT patent/HRP20221360T1/hr unknown
- 2017-12-15 WO PCT/EP2017/083030 patent/WO2018109167A1/en unknown
- 2017-12-15 PL PL17825466.0T patent/PL3555269T3/pl unknown
- 2017-12-15 ES ES17825466T patent/ES2930358T3/es active Active
-
2019
- 2019-05-30 ZA ZA2019/03482A patent/ZA201903482B/en unknown
- 2019-06-14 MX MX2022015233A patent/MX2022015233A/es unknown
-
2022
- 2022-07-26 US US17/815,059 patent/US20230135852A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
DK3555269T3 (da) | 2022-11-28 |
ES2930358T3 (es) | 2022-12-09 |
WO2018109167A1 (en) | 2018-06-21 |
EP3555269A1 (en) | 2019-10-23 |
ZA201903482B (en) | 2022-12-21 |
US20230135852A1 (en) | 2023-05-04 |
BR112019012276B1 (pt) | 2022-08-02 |
BR112019012276A2 (pt) | 2019-11-26 |
EP3555269B1 (en) | 2022-08-31 |
CN110291193B (zh) | 2024-03-08 |
MX2022015233A (es) | 2023-01-11 |
PL3555269T3 (pl) | 2022-12-19 |
US20200102582A1 (en) | 2020-04-02 |
CN110291193A (zh) | 2019-09-27 |
EP4159850A1 (en) | 2023-04-05 |
HUE060726T2 (hu) | 2023-04-28 |
US11434506B2 (en) | 2022-09-06 |
DE17825466T1 (de) | 2019-12-12 |
RS63726B1 (sr) | 2022-12-30 |
MX2019007048A (es) | 2019-08-01 |
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