DK2654455T3 - Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere - Google Patents
Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere Download PDFInfo
- Publication number
- DK2654455T3 DK2654455T3 DK11819164.2T DK11819164T DK2654455T3 DK 2654455 T3 DK2654455 T3 DK 2654455T3 DK 11819164 T DK11819164 T DK 11819164T DK 2654455 T3 DK2654455 T3 DK 2654455T3
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- Prior art keywords
- nitrooxy
- formula
- organic molecule
- methane
- cyclic
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 235000021135 plant-based food Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000003753 real-time PCR Methods 0.000 description 1
- 238000009418 renovation Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000003757 reverse transcription PCR Methods 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- PWYYWQHXAPXYMF-UHFFFAOYSA-N strontium(2+) Chemical compound [Sr+2] PWYYWQHXAPXYMF-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ZUUZGQPEQORUEV-UHFFFAOYSA-N tetrahydrate;hydrochloride Chemical compound O.O.O.O.Cl ZUUZGQPEQORUEV-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
- 239000011652 vitamin K3 Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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- A—HUMAN NECESSITIES
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
- C07C207/02—Compounds containing nitroso groups bound to a carbon skeleton the carbon skeleton not being further substituted
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
- C07C207/04—Compounds containing nitroso groups bound to a carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
- C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/70—Nitro radicals
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- C07D493/04—Ortho-condensed systems
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Claims (18)
1. Anvendelse af mindst et organisk molekyle, der er substitueret i en hvilken som helst position med mindst en nitrooxygruppe, eller et salt deraf, som defineret af formlen (I)
hvor Y er et organisk molekyle med følgende sammensætning: CaHbOdNeSg, hvor a ligger på mellem 1 og 25, b ligger på mellem 2 og 51, d ligger på mellem 0 og 8, e ligger på mellem 0 og 5, g ligger på mellem 0 og 3, som en aktiv forbindelse i dyrefoder for at reducere dannelsen af methan, som fremkommer ved drøvtyggeres fordøjelsesaktiviteter, hvor nitrooxyalkansyre, og/eller derivater deraf, som defineret af formlen (II) er udelukket,
hvor u ligger på mellem 0 og 23, og hvor carbonkæden, hvis u + 0, er en lineær, cyklisk eller forgrenet lineær eller cyklisk alifatisk carbonkæde, som kan være mono- eller polyumættet og på en hvilken som helst isomerform, Z uafhængigt er O, NH eller N-R3, hvor Z-Rl-, hvis RI + H, betegner en ester eller et sekundært amidderivat, RI uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 10 carbonatomer, R2 uafhængigt er hydrogen eller en mættet lige eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 23 carbonatomer, og R3 uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som
indeholder 1 til 10 carbonatomer.
2. Anvendelse ifølge krav 1, hvor a ligger på mellem 1 og 10, b ligger på mellem 2 og 21, d ligger på mellem 0 og 6, e ligger på mellem 0 og 3, g ligger på mellem 0 og 1.
3. Anvendelse ifølge krav 1, hvor det mindst ene organiske molekyle
med formlen (I) er en forbindelse med formlen (III), hvor n ligger på mellem 0 og 12, fortrinsvis på mellem 0 og 6, og hvor carbonkæden, hvis n + 0, er en lineær, cyklisk eller forgrenet alifatisk carbonkæde, som kan være ikke-substitueret eller substitueret med op til tre hydroxy-, alkoxy-, amino-, alkylamino-, dialkylamino- eller nitrooxygrupper, eller en mono- eller polyumættet alkenyl- eller alkynylcarbonkæde på en hvilken som helst isomerform, R4 uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 12, fortrinsvis 1 til 6 carbonatomer. X er hydrogen, R5, R5=n, -OR5, -OCOR5, -NR5R6, -ONO2, -COOR5, -CONR5R6, -NHSO2R5 eller -SO2NHR5, R5 og R6 uafhængigt er hydrogen, lige, forgrenet eller cyklisk Cl-C12-alkylkæde, der kan være ikke-substitueret eller substitueret med op til tre hydroxy-, alkoxy-, amino-, alkylamino-, dialkylamino- eller nitrooxygrupper, mono- eller polyumættet alkenyl- eller alkynylcarbonkæde på en hvilken som helst isomerform.
4. Anvendelse ifølge et hvilket som helst af kravene 1 til 3, hvor det mindst ene organiske molekyle med formlen (I), eller et salt deraf, er valgt blandt 3-nitrooxypropanol, racemat-4-phenylbutan-l,2-diyldinitrat, 2-(hydroxymethyl)-2-
(nitrooxymethyl)-1,3-propandiol, N-ethyl-3-nitrooxy- propionsulfonylamid, 5-nitrooxy-pentannitril, 5-nitrooxy- pentan, 3-nitrooxy-propylpropionat, 1,3-bis-nitrooxypropan, 1,4-bis-nitrooxybutan, 1,5-bis-nitrooxypentan, 3-nitrooxy-propylbenzoat, 3-nitrooxy-propylhexanoat, 3-nitrooxy-propyl- 5-nitrooxy-hexanoat, benzylnitrat, isosorbid-dinitrat og N-[2-(nitrooxy)ethyl]-3-pyridincarboxamid, 2-nitro-5- nitrooxymethyl-furan og bis-(2-nitrooxyethyl)ether .
5. Anvendelse ifølge et hvilket som helst af kravene 1 til 4, hvor det mindst ene organiske molekyle med formlen (I), eller et salt deraf, er valgt blandt 3-nitrooxypropanol, 5-nitrooxy-pentannitril, 5-nitrooxy-pentan, 3-nitrooxy- propylpropionat, 1,3-bis-nitrooxypropan, 1,4-bis- nitrooxybutan, 1,5-bis-nitrooxypentan, 3-nitrooxy- propylbenzoat, 3-nitrooxy-propylhexanoat, 3-nitrooxy-propyl-5-nitrooxy-hexanoat, isosorbid-dinitrat og N-[2-(nitrooxy)ethyl]-3-pyridincarboxamid og bis-(2- nitrooxyethyl) ether.
6. Anvendelse ifølge et hvilket som helst af kravene 1 til 5, hvor det mindst ene organiske molekyle med formlen (I) er en blanding af 3-nitrooxypropanol og 1,3-bis-nitrooxypropan.
7. Anvendelse ifølge et hvilket som helst af kravene 1 til 6, hvor det mindst ene organiske molekyle med formlen (I), eller et salt deraf, kombineres med mindst et yderligere aktivt stof, der er valgt fra gruppen bestående af diallyldisulfid, hvidløgsolie, allylisothiocyanat, deoxycholsyre, chenodeoxycholsyre og derivater deraf.
8. Anvendelse ifølge et hvilket som helst af kravene 1 til 7, hvor det drøvtyggende dyr er valgt fra gruppen bestående af: kvæg, geder, får, giraffer, amerikanske bisoner, europæiske bisoner, yakokser, vandbøfler, hjorte, kameler, alpakaer, lamaer, gnuer, antiloper, gaffelbukke og nilgaiantiloper.
9. Anvendelse ifølge et hvilket som helst af kravene 1 til 8, hvor methanproduktionen hos drøvtyggere beregnet i liter pr. kilogram tørstofindtag reduceres med mindst 10 % ved måling i metaboliske kamre.
10. Anvendelse ifølge et hvilket som helst af kravene 1 til 9, hvor mængden af den mindst ene aktive forbindelse som defineret i formlen (I), der indgives til det drøvtyggende dyr, er fra 1 mg til 10 g pr. kg foder.
11. Fodersammensætning eller foderadditiv til drøvtyggere, der omfatter mindst et organisk molekyle med formlen (I) ifølge et hvilket som helst af kravene 2 til 6.
12. Fodersammensætning eller foderadditiv til drøvtyggere ifølge krav 11, der endvidere omfatter en ingrediens valgt fra gruppen bestående af calciumcarbonater, elektrolytter, proteiner, bønnekager, hvede, stivelse, solsikkekager, majs, kød- og benmel, aminosyrer, animalsk fedt, vitaminer og spormineraler.
13. Sammensætning ifølge krav 11, som er en mineralforblanding, en vitaminforblanding eller en forblanding, der indbefatter vitaminer og mineraler, eller en bolus.
14. Fremgangsmåde til reducering af produktionen af methan, som fremkommer ved drøvtyggeres fordøjelsesaktiviteter, hvilken fremgangsmåde omfatter oral indgivelse til dyret af en tilstrækkelig mængde af mindst et organisk molekyle, som er substitueret i en hvilken som helst position med mindst en nitrooxygruppe, eller et salt deraf, som defineret af formlen
forme! (!) hvor Y er et organisk molekyle med følgende sammensætning: CaHbOdNeSg, hvor a ligger på mellem 1 og 25,
b ligger på mellem 2 og 51, d ligger på mellem 0 og 8, e ligger på mellem 0 og 5, g ligger på mellem 0 og 3, hvor nitrooxyalkansyre, og/eller derivat deraf, som defineret af formlen (II) er udelukket,
forme! (I!) hvor u ligger på mellem 0 og 23, og hvor carbonkæden, hvis u + 0, er en lineær, cyklisk eller forgrenet lineær eller cyklisk alifatisk carbonkæde, som kan være mono- eller polyumættet og på en hvilken som helst isomerform, Z uafhængigt er O, NH eller N-R3, hvor Z-Rl, hvis RI + H, betegner en ester eller et sekundært amidderivat, RI uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 10 carbonatomer, R2 uafhængigt er hydrogen eller en mættet lige eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 23 carbonatomer, og R3 uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 10 carbonatomer.
15. Fremgangsmåde ifølge krav 14, hvor det mindst ene organiske molekyle indgives til dyret i kombination med mindst et yderligere aktivt stof, der er valgt fra gruppen bestående af diallyldisulfid, hvidløgsolie, allylisothiocyanat, deoxycholsyre, chenodeoxycholsyre og derivater deraf.
16. Fremgangsmåde ifølge krav 14 eller 15, hvor det drøvtyggende dyr er valgt fra gruppen bestående af: kvæg, geder, får, giraffer, amerikanske bisoner, europæiske bisoner, yakokser, vandbøfler, hjorte, kameler, alpakaer, lamaer, gnuer, antiloper, gaffelbukke og nilgaiantiloper.
17. Fremgangsmåde ifølge et hvilket som helst af kravene 14 til 16, hvor mængden af det mindst ene organiske molekyle som defineret i formlen (I), der indgives til det drøvtyggende dyr, er fra 1 mg til 10 g pr. kg foder.
18. Fremgangsmåde ifølge et hvilket som helst af kravene 14 til 17, hvor methanproduktionen hos drøvtyggere beregnet i liter pr. kilogram tørstofindtag reduceres med mindst 10 % ved måling i metaboliske kamre.
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EP10195857 | 2010-12-20 | ||
EP11178994 | 2011-08-26 | ||
PCT/EP2011/072707 WO2012084629A1 (en) | 2010-12-20 | 2011-12-20 | Use of nitrooxy organic molecules in feed for reducing methane emission in ruminants, and/or to improve ruminant performance |
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DK2654455T3 true DK2654455T3 (da) | 2019-02-18 |
Family
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DK11819164.2T DK2654455T3 (da) | 2010-12-20 | 2011-12-20 | Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere |
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US (2) | US9266814B2 (da) |
EP (1) | EP2654455B1 (da) |
JP (1) | JP5984189B2 (da) |
KR (1) | KR101927553B1 (da) |
CN (1) | CN103260424B (da) |
AU (1) | AU2011347802B2 (da) |
BR (1) | BR112013015569B1 (da) |
DK (1) | DK2654455T3 (da) |
ES (1) | ES2707876T3 (da) |
NZ (1) | NZ610031A (da) |
PL (1) | PL2654455T3 (da) |
RU (1) | RU2578485C2 (da) |
WO (1) | WO2012084629A1 (da) |
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- 2011-12-20 WO PCT/EP2011/072707 patent/WO2012084629A1/en active Application Filing
- 2011-12-20 US US13/996,026 patent/US9266814B2/en active Active
- 2011-12-20 KR KR1020137015688A patent/KR101927553B1/ko active IP Right Grant
- 2011-12-20 DK DK11819164.2T patent/DK2654455T3/da active
- 2011-12-20 JP JP2013543741A patent/JP5984189B2/ja active Active
- 2011-12-20 CN CN201180061610.7A patent/CN103260424B/zh active Active
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- 2011-12-20 BR BR112013015569-8A patent/BR112013015569B1/pt active IP Right Grant
- 2011-12-20 ES ES11819164T patent/ES2707876T3/es active Active
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US20140147529A1 (en) | 2014-05-29 |
CN103260424B (zh) | 2016-05-11 |
BR112013015569B1 (pt) | 2020-03-03 |
US9266814B2 (en) | 2016-02-23 |
PL2654455T3 (pl) | 2019-05-31 |
KR101927553B1 (ko) | 2018-12-10 |
CN103260424A (zh) | 2013-08-21 |
BR112013015569A2 (pt) | 2016-07-19 |
ES2707876T3 (es) | 2019-04-05 |
JP5984189B2 (ja) | 2016-09-06 |
US9902685B2 (en) | 2018-02-27 |
AU2011347802B2 (en) | 2015-05-07 |
AU2011347802A8 (en) | 2013-06-06 |
NZ610031A (en) | 2015-01-30 |
RU2578485C2 (ru) | 2016-03-27 |
AU2011347802A1 (en) | 2013-05-09 |
RU2013133968A (ru) | 2015-01-27 |
EP2654455A1 (en) | 2013-10-30 |
EP2654455B1 (en) | 2018-10-24 |
WO2012084629A1 (en) | 2012-06-28 |
US20150376113A1 (en) | 2015-12-31 |
JP2013545485A (ja) | 2013-12-26 |
KR20130126642A (ko) | 2013-11-20 |
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