RU2018101137A - Галоген-замещенные феноксифениламидины и их применение в качестве фунгицидов - Google Patents
Галоген-замещенные феноксифениламидины и их применение в качестве фунгицидов Download PDFInfo
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- RU2018101137A RU2018101137A RU2018101137A RU2018101137A RU2018101137A RU 2018101137 A RU2018101137 A RU 2018101137A RU 2018101137 A RU2018101137 A RU 2018101137A RU 2018101137 A RU2018101137 A RU 2018101137A RU 2018101137 A RU2018101137 A RU 2018101137A
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- phenoxyphenylamidine
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- 239000000417 fungicide Substances 0.000 title 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 244000005700 microbiome Species 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 claims 3
- GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical class NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000004970 halomethyl group Chemical group 0.000 claims 3
- FJLHLDBEZKTSOK-UHFFFAOYSA-N n-ethyl-n-methylformamide Chemical compound CCN(C)C=O FJLHLDBEZKTSOK-UHFFFAOYSA-N 0.000 claims 3
- 150000002905 orthoesters Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001409 amidines Chemical class 0.000 claims 2
- 150000001448 anilines Chemical class 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 230000009261 transgenic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical class [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 claims 1
- HEDRJSWPTSCHKP-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)peroxybenzene Chemical class [O-][N+](=O)C1=CC=CC=C1OOOC1=CC=CC=C1[N+]([O-])=O HEDRJSWPTSCHKP-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BSNAXLVEASCQEH-UHFFFAOYSA-N N'-[2-(difluoromethyl)-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide Chemical compound FC(C1=C(C=C(C(=C1)OC1=C(C=CC=C1)F)C)N=CN(C)CC)F BSNAXLVEASCQEH-UHFFFAOYSA-N 0.000 claims 1
- GVQSSVGUWFFCAV-UHFFFAOYSA-N N'-[2-bromo-4-(2-bromophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide Chemical compound BrC1=C(C=C(C(=C1)OC1=C(C=CC=C1)Br)C)N=CN(C)CC GVQSSVGUWFFCAV-UHFFFAOYSA-N 0.000 claims 1
- PVYDHJJIDIIWPB-UHFFFAOYSA-N N'-[2-bromo-4-(2-chlorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide Chemical compound BrC1=C(C=C(C(=C1)OC1=C(C=CC=C1)Cl)C)N=CN(C)CC PVYDHJJIDIIWPB-UHFFFAOYSA-N 0.000 claims 1
- IHTVXBHEUYKFGC-UHFFFAOYSA-N N'-[2-bromo-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide Chemical compound BrC1=C(C=C(C(=C1)OC1=C(C=CC=C1)F)C)N=CN(C)CC IHTVXBHEUYKFGC-UHFFFAOYSA-N 0.000 claims 1
- CPVTZGYSYCOCBU-UHFFFAOYSA-N N'-[2-chloro-4-(2-chlorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide Chemical compound ClC1=C(C=C(C(=C1)OC1=C(C=CC=C1)Cl)C)N=CN(C)CC CPVTZGYSYCOCBU-UHFFFAOYSA-N 0.000 claims 1
- SQCJYCIUZGDBPJ-UHFFFAOYSA-N N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide Chemical compound ClC1=C(C=C(C(=C1)OC1=C(C=CC=C1)F)C)N=CN(C)CC SQCJYCIUZGDBPJ-UHFFFAOYSA-N 0.000 claims 1
- FPDAZWSJQUNCKG-UHFFFAOYSA-N N'-[2-chloro-4-(2-iodophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide Chemical compound ClC1=C(C=C(C(=C1)OC1=C(C=CC=C1)I)C)N=CN(C)CC FPDAZWSJQUNCKG-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 claims 1
- 150000005181 nitrobenzenes Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
- A01C1/06—Coating or dressing seed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Soil Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Claims (73)
1. Феноксифениламидин общей формулы (I)
в которой
R1 выбирают из группы, состоящей из галогена и галометила;
R2 представляет собой метил;
R3 представляет собой галоген;
или его соли, N-оксиды, комплексные соединения металлов и его стереоизомеры.
2. Феноксифениламидин по п. 1, в котором
R1 выбирают из группы, состоящей из фтора, хлора, брома, дихлорметила, трихлорметила, фторметила, дифторметила и трифторметила;
R2 представляет собой метил;
R3 выбирают из группы, состоящей из брома, хлора и фтора.
3. Феноксифениламидин по п. 1, в котором
R1 выбирают из группы, состоящей из хлора, брома, дифторметила и трифторметила;
R2 представляет собой метил;
R3 представляет собой фтор и хлор.
4. Феноксифениламидин по любому из пп. 1-3, выбранный из группы, состоящей из N'-[2-хлор-4-(2-фторфенокси)-5-метилфенил]-N-этил-N-метилимидоформамида, N'-[2-(дифторметил)-4-(2-фторфенокси)-5-метилфенил]-N-этил-N-метилимидоформамида, N'-[2-бром-4-(2-фторфенокси)-5-метилфенил]-N-этил-N-метилимидоформамида, N'-[2-бром-4-(2-хлорфенокси)-5-метилфенил]-N-этил-N-метилимидоформамида, N'-[2-хлор-4-(2-хлорфенокси)-5-метилфенил]-N-этил-N-метилимидоформамида, N'-[2-хлор-4-(2-иодфенокси)-5-метилфенил]-N-этил-N-метилимидоформамида, N'-[2-бром-4-(2-бромфенокси)-5-метилфенил]-N-этил-N-метилимидоформамида.
5. Способ получения феноксифениламидина по любому из пп. 1-4, который включает по меньшей мере одну из следующих стадий (а)-(j):
(а) реакция нитробензольных производных формулы (III) с фенольными производными формулы (II) согласно реакционной схеме, показанной далее:
(b) реакция нитрофенольных производных формулы (V) с фенильными производными формулы (IV) согласно реакционной схеме, показанной далее:
(c) реакция анилинов формулы (VII) с фенолами (II) согласно реакционной схеме, показанной далее:
(d) реакция аминофенолов формулы (XII) с фенильными производными формулы (IV) согласно реакционной схеме, показанной далее:
(e) восстановление нитрофенокси простых эфиров формулы (VI) до аминофениловых простых эфиров формулы (VIII) согласно реакционной схеме, показанной далее:
(f) реакция аминофениловых простых эфиров формулы (VIII) с
(i) аминоацеталями формулы (XIII) или
(ii) с N-этил-N-метилформамидом формулы (XIV) или
(iv) с N-метилэтанамином формулы (XV) в присутствии сложных ортоэфиров формулы (XVI)
согласно реакционной схеме, показанной далее:
(g) реакция аминофенолов формулы (XII) с
(i) аминоацеталями формулы (XIII) или
(ii) с N-этил-N-метилформамидом формулы (XIV) или
(iv) с N-метилэтанамином формулы (XV) в присутствии сложных ортоэфиров формулы (XVI)
согласно реакционной схеме, показанной далее:
(h) реакция анилинов формулы (VII) с
(i) аминоацеталями формулы (XIII) или
(ii) с N-этил-N-метилформамидом формулы (XIV) или
(iii) с N-метилэтанамином формулы (XV) в присутствии сложных ортоэфиров формулы (XVI) согласно реакционной схеме, показанной далее:
(i) реакция амидинов формулы (XI) с фенольными производными формулы (II) согласно реакционной схеме, показанной далее:
(j) реакция амидинов формулы (XI) с фенильными производными формулы (IV) согласно реакционной схеме, показанной далее:
где в приведенных выше схемах
Z представляет собой уходящую группу;
R1-R3 имеют значения как в п. 1;
R6 и R7 независимо друг от друга выбираются из группы, состоящей из C1-12-алкильных, C2-12-алкенильных, С2-12-алкинильных или C5-18-арильных или С7-19-арилалкильных групп, и вместе с атомами, к которым они присоединены, могут образовывать пяти-, шести- или семи-членное кольцо;
R8-R10 независимо друг от друга выбираются из группы, состоящей из C1-12-алкильных, С2-12-алкенильных, С2-12-алкинильных или С5-18-арильных или С7-19-арилалкильных, С7-19-алкиларильных групп, и, в каждом случае, R8 с R9, R9 с R10 или R8 с R10 вместе с атомами, к которым они присоединены, и, если является подходящим, вместе с другими атомами углерода, азота, кислорода или серы, могут образовывать пяти-, шести- или семи-членное кольцо.
6. Нитрофениловые простые эфиры формулы (VI)
в которой
R1 выбирают из группы, состоящей из галогена и галометила;
R2 представляет собой метил;
R3 представляет собой галоген.
7. Аминофениловые простые эфиры формулы (VIII)
в которой
R1 выбирают из группы, состоящей из галогена и галометила;
R2 представляет собой метил;
R3 представляет собой галоген.
8. Сельскохозяйственная композиция для борьбы с нежелательными микроорганизмами, содержащая по меньшей мере один феноксифениламидин по любому из пп. 1-4.
9. Применение феноксифениламидина по любому из пп. 1-4 или сельскохозяйственной композиции по п. 8 для борьбы с нежелательными микроорганизмами.
10. Способ борьбы с нежелательными микроорганизмами, отличающийся тем, что замещенные феноксифениламидины по любому из пп. 1-4 или сельскохозяйственные композиции по п. 8 применяются к микроорганизмам и/или области их обитания.
11. Семя, обработанное по меньшей мере одним феноксифениламидином по любому из пп. 1-4.
12. Применение феноксифениламидин по любому из пп. 1-4 для обработки семени.
13. Применение феноксифениламидин по любому из пп. 1-4 для обработки трансгенных растений.
14. Применение феноксифениламидин по любому из пп. 1-4 для обработки семени трансгенных растений.
15. Способ защиты семени от нежелательных микрорганизмов посредством применения семени, обработанного по меньшей мере одним феноксифениламидином по любому из пп. 1-4.
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Application Number | Priority Date | Filing Date | Title |
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EP15172107 | 2015-06-15 | ||
EP15172107.3 | 2015-06-15 | ||
PCT/EP2016/063508 WO2016202742A1 (en) | 2015-06-15 | 2016-06-13 | Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides |
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RU2018101137A true RU2018101137A (ru) | 2019-07-15 |
RU2018101137A3 RU2018101137A3 (ru) | 2019-12-16 |
RU2733511C2 RU2733511C2 (ru) | 2020-10-02 |
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US (2) | US10506807B2 (ru) |
EP (1) | EP3307707B1 (ru) |
JP (1) | JP2018522846A (ru) |
CN (1) | CN107848959B (ru) |
AR (1) | AR104995A1 (ru) |
AU (1) | AU2016279819B2 (ru) |
BR (1) | BR112017027189B8 (ru) |
CA (1) | CA2989237A1 (ru) |
DK (1) | DK3307707T3 (ru) |
ES (1) | ES2837098T3 (ru) |
HR (1) | HRP20202011T1 (ru) |
HU (1) | HUE051950T2 (ru) |
IL (1) | IL256078B (ru) |
LT (1) | LT3307707T (ru) |
MX (1) | MX2017016363A (ru) |
PL (1) | PL3307707T3 (ru) |
PT (1) | PT3307707T (ru) |
RS (1) | RS61217B1 (ru) |
RU (1) | RU2733511C2 (ru) |
SI (1) | SI3307707T1 (ru) |
TW (1) | TW201710237A (ru) |
UA (1) | UA123211C2 (ru) |
UY (1) | UY36730A (ru) |
WO (1) | WO2016202742A1 (ru) |
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2016
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- 2016-06-13 JP JP2017564700A patent/JP2018522846A/ja not_active Ceased
- 2016-06-13 LT LTEP16732972.1T patent/LT3307707T/lt unknown
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- 2016-06-13 BR BR112017027189A patent/BR112017027189B8/pt not_active IP Right Cessation
- 2016-06-13 SI SI201631024T patent/SI3307707T1/sl unknown
- 2016-06-13 DK DK16732972.1T patent/DK3307707T3/da active
- 2016-06-13 UA UAA201800339A patent/UA123211C2/uk unknown
- 2016-06-13 MX MX2017016363A patent/MX2017016363A/es unknown
- 2016-06-13 WO PCT/EP2016/063508 patent/WO2016202742A1/en active Application Filing
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2019
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AU2016279819B2 (en) | 2020-07-16 |
TW201710237A (zh) | 2017-03-16 |
IL256078B (en) | 2020-07-30 |
BR112017027189A2 (ru) | 2018-08-21 |
US20180153167A1 (en) | 2018-06-07 |
BR112017027189B1 (pt) | 2021-10-26 |
BR112017027189B8 (pt) | 2021-12-14 |
LT3307707T (lt) | 2021-01-11 |
CN107848959A (zh) | 2018-03-27 |
PL3307707T3 (pl) | 2021-04-19 |
RU2733511C2 (ru) | 2020-10-02 |
PT3307707T (pt) | 2020-12-23 |
US20200068886A1 (en) | 2020-03-05 |
EP3307707A1 (en) | 2018-04-18 |
HRP20202011T1 (hr) | 2021-04-02 |
ES2837098T3 (es) | 2021-06-29 |
EP3307707B1 (en) | 2020-10-07 |
AU2016279819A1 (en) | 2018-01-04 |
RU2018101137A3 (ru) | 2019-12-16 |
RS61217B1 (sr) | 2021-01-29 |
AR104995A1 (es) | 2017-08-30 |
US10506807B2 (en) | 2019-12-17 |
MX2017016363A (es) | 2018-03-02 |
WO2016202742A1 (en) | 2016-12-22 |
CA2989237A1 (en) | 2016-12-22 |
DK3307707T3 (da) | 2020-12-21 |
UY36730A (es) | 2016-12-30 |
IL256078A (en) | 2018-01-31 |
JP2018522846A (ja) | 2018-08-16 |
SI3307707T1 (sl) | 2021-03-31 |
UA123211C2 (uk) | 2021-03-03 |
CN107848959B (zh) | 2021-07-27 |
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