AR104178A1 - Derivados de imidazolilmetilo 5-sustituidos - Google Patents
Derivados de imidazolilmetilo 5-sustituidosInfo
- Publication number
- AR104178A1 AR104178A1 ARP160100901A ARP160100901A AR104178A1 AR 104178 A1 AR104178 A1 AR 104178A1 AR P160100901 A ARP160100901 A AR P160100901A AR P160100901 A ARP160100901 A AR P160100901A AR 104178 A1 AR104178 A1 AR 104178A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- halogen
- alkoxy
- Prior art date
Links
- 229910052736 halogen Inorganic materials 0.000 abstract 50
- 150000002367 halogens Chemical group 0.000 abstract 47
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 41
- 125000000217 alkyl group Chemical group 0.000 abstract 29
- -1 5-substituted imidazolylmethyl Chemical class 0.000 abstract 24
- 125000003545 alkoxy group Chemical group 0.000 abstract 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 16
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 15
- 125000005843 halogen group Chemical group 0.000 abstract 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 12
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 11
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 9
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 8
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 abstract 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 7
- 125000001188 haloalkyl group Chemical group 0.000 abstract 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 7
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 5
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical group NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 abstract 5
- 125000004429 atom Chemical group 0.000 abstract 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 5
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 abstract 5
- 150000002923 oximes Chemical group 0.000 abstract 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 3
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 abstract 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 2
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 abstract 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 2
- 125000005159 cyanoalkoxy group Chemical group 0.000 abstract 2
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 2
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 abstract 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Chemical group 0.000 abstract 2
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 2
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000012948 isocyanate Chemical group 0.000 abstract 2
- 150000002513 isocyanates Chemical group 0.000 abstract 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 2
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000008635 plant growth Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/68—Halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/84—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (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)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Derivados de imidazolilmetilo 5-sustituidos, a procesos para preparar estos compuestos, a composiciones que comprenden estos compuestos y a su uso como compuestos biológicamente activos, en especial para controlar los microorganismos nocivos en la protección de cultivos y en la protección de materiales y como reguladores del crecimiento de plantas. Reivindicación 1: Derivados de imidazol de la fórmula (1) en donde R¹ representa hidrógeno, en cada caso opcionalmente ramificado alquilo C₁₋₈, haloalquilo C₁₋₈, alquenilo C₂₋₇, haloalquenilo C₂₋₇, alquinilo C₂₋₈, haloalquinilo C₂₋₈, cicloalquilo C₃₋₇ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio, bicicloalquilo opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; cicloalquilalquilo C₃₋₈ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; halocicloalquil C₃₋₇-alquilo C₁₋₄ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; halocicloalquil C₃₋₇-haloalquilo C₁₋₄ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; cicloalquil C₃₋₇-haloalquilo C₁₋₄ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; cicloalquil C₃₋₇-cicloalquilo C₃₋₇ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; cicloalquenilo C₃₋₇ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; tri(alquil C₁₋₈)silil-alquilo C₁₋₄ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; tri(alquil C₁₋₈)silil-cicloalquilo C₃₋₇ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; R² representa H, alquilo C₁₋₈, -Si(R³ᵃ)(R³ᵇ)(R³ᶜ), -P(O)(OH)₂, -CH₂-O-P(O)(OH)₂, -C(O)-alquilo C₁₋₈, -C(O)-cicloalquilo C₃₋₇, -C(O)NH-alquilo C₁₋₈; -C(O)N-di-alquilo C₁₋₈; -C(O)O-alquilo C₁₋₈; en donde el -C(O)-alquilo C₁₋₈, -C(O)-cicloalquilo C₃₋₇, -C(O)NH-alquilo C₁₋₈; -C(O)N-di-alquilo C₁₋₈ o -C(O)O-alquilo C₁₋₈ puede no estar sustituido o puede estar sustituido con uno o varios grupos seleccionados de halógeno o alcoxi C₁₋₈; en donde R³ᵃ, R³ᵇ, R³ᶜ representan, de modo independiente entre sí, un fenilo o alquilo C₁₋₈; R³ representa halógeno; hidroxilo; ciano; isociano; nitro; amino; sulfanilo; pentafluoro-l⁶-sulfanilo; carboxaldehído, hidroxicarbonilo, alquilo C₁₋₈; haloalquilo C₁₋₈; cianoalquilo C₁₋₈; alquil C₁₋₈-oxi; halógenoalquil C₁₋₈-oxi; tri(alquil C₁₋₈)sililo; tri(alquil C₁₋₈)silil-alquilo C₁₋₈; cicloalquilo C₃₋₇; halógenocicloalquilo C₃₋₇; cicloalquenilo C₃₋₇; halógenocicloalquenilo C₃₋₇; cicloalquilalquilo C₄₋₁₀; halocicloalquilalquilo C₄₋₁₀; cicloalquilcicloalquilo C₆₋₁₂; alquil C₁₋₈-cicloalquilo C₃₋₇; alcoxi C₁₋₈-cicloalquilo C₃₋₇; tri(alquil C₁₋₈)silil-cicloalquilo C₃₋₇; alquenilo C₂₋₈; alquinilo C₂₋₈; alquenil C₂₋₈-oxi; halógenoalquenil C₂₋₈-oxi; alquinil C₃₋₈-oxi; halógenoalquinil C₃₋₈-oxi; alquil C₁₋₈-amino; halógenoalquil C₁₋₈-amino; cianoalcoxi C₁₋₈; cicloalquilalcoxi C₄₋₈; cicloalcoxi C₃₋₆; alquil C₁₋₈-sulfanilo; halógenoalquil C₁₋₈-sulfanilo; alquil C₁₋₈-carbonilo; halógenoalquil C₁₋₈-carbonilo; arilcarbonilo; aril-alquil C₁₋₆-carbonilo; cicloalquil C₃₋₈-carbonilo; halógenocicloalquil C₃₋₈-carbonilo; alquil C₁₋₈-carbamoílo; di-alquil C₁₋₈-carbamoílo; N-alquil C₁₋₈-oxicarbamoílo; alcoxi C₁₋₈-carbamoílo; N-alquil C₁₋₈-alcoxi C₁₋₈-carbamoílo; aminotiocarbonilo; alcoxi C₁₋₈-carbonilo; halógenoalcoxi C₁₋₈-carbonilo; cicloalcoxi C₃₋₈-carbonilo; alcoxialquil C₂₋₈-carbonilo; halógenoalcoxialquil C₂₋₈-carbonilo; cicloalcoxialquil C₃₋₁₀-carbonilo; alquil C₁₋₈-aminocarbonilo; di-alquil C₁₋₈-aminocarbonilo; cicloalquil C₃₋₈-aminocarbonilo; alquil C₁₋₈-carboniloxi; halógenoalquil C₁₋₈-carboniloxi; cicloalquil C₃₋₈-carboniloxi; alquil C₁₋₈-carbonilamino; halógenoalquil C₁₋₈-carbonilamino; alquil C₁₋₈-aminocarboniloxi; di-alquil C₁₋₈-aminocarboniloxi; alquil C₁₋₈-oxicarboniloxi; alquil C₁₋₈-sulfinilo; halógenoalquil C₁₋₈-sulfinilo; alquil C₁₋₈-sulfonilo; halógenoalquil C₁₋₈-sulfonilo; alquil C₁₋₈-sulfoniloxi; halógenoalquil C₁₋₈-sulfoniloxi; alquil C₁₋₈-aminosulfamoílo; di-alquil C₁₋₈-aminosulfamoílo; (alcoxi C₁₋₈-imino)-alquilo C₁₋₈; (cicloalcoxi C₃₋₇-imino)-alquilo C₁₋₈; hidroxiimino-alquilo C₁₋₈; (alcoxi C₁₋₈-imino)-cicloalquilo C₃₋₇; hidroxiimino-cicloalquilo C₃₋₇; (alquil C₁₋₈-imino)-oxi; (alquil C₁₋₈-imino)-oxi-alquilo C₁₋₈; (cicloalquil C₃₋₇-imino)-oxi-alquilo C₁₋₈; (alquil C₁₋₆-imino)-oxi-cicloalquilo C₃₋₇; (alquenil C₁₋₈-oxiimino)-alquilo C₁₋₈; (alquinil C₁₋₈-oxiimino)-alquilo C₁₋₈; (benciloxiimino)-alquilo C₁₋₈; alcoxialquilo C₁₋₈; alquiltioalquilo C₁₋₈; alcoxialcoxialquilo C₁₋₈; halógenoalcoxialquilo C₁₋₈; bencilo; fenilo; heteroarilo de 5 miembros; heteroarilo de 6 miembros; benciloxi; feniloxi; bencilsulfanilo; bencilamino; fenilsulfanilo; o fenilamino; en donde el bencilo, fenilo, heteroarilo de 5 miembros, heteroarilo de 6 miembros, benciloxi o feniloxi pueden estar opcionalmente sustituidos con uno o varios grupos seleccionados de halógeno; hidroxilo; ciano; isociano; amino; sulfanilo; pentafluoro-l⁶-sulfanilo; carboxaldehído, hidroxicarbonilo, alquilo C₁₋₈; haloalquilo C₁₋₈; cianoalquilo C₁₋₈; alquil C₁₋₈-oxi; halógenoalquil C₁₋₈-oxi; tri(alquil C₁₋₈)sililo; tri(alquil C₁₋₈)silil-alquilo C₁₋₈; cicloalquilo C₃₋₇; halógenocicloalquilo C₃₋₇; cicloalquenilo C₃₋₇; halógenocicloalquenilo C₃₋₇; cicloalquilalquilo C₄₋₁₀; halocicloalquilalquilo C₄₋₁₀; cicloalquilcicloalquilo C₆₋₁₂; alquil C₁₋₈-cicloalquilo C₃₋₇; alcoxi C₁₋₈-cicloalquilo C₃₋₇; tri(alquil C₁₋₈)silil-cicloalquilo C₃₋₇; alquenilo C₂₋₈; alquinilo C₂₋₈; alquenil C₂₋₈-oxi; halógenoalquenil C₂₋₈-oxi; alquinil C₃₋₈-oxi; halógenoalquinil C₃₋₈-oxi; alquil C₁₋₈-amino; halógenoalquil C₁₋₈-amino; cianoalcoxi C₁₋₈; cicloalquilalcoxi C₄₋₈; cicloalcoxi C₃₋₆; alquil C₁₋₈-sulfanilo halógenoalquil C₁₋₈-sulfanilo; alquil C₁₋₈-carbonilo; halógenoalquil C₁₋₈-carbonilo; arilcarbonilo; aril-alquil C₁₋₆-carbonilo; cicloalquil C₃₋₈-carbonilo; halógenocicloalquil C₃₋₈-carbonilo; alquil C₁₋₈-carbamoílo; di-alquil C₁₋₈-carbamoílo; N-alquil C₁₋₈-oxicarbamoílo; alcoxi C₁₋₈-carbamoílo; N-alquil C₁₋₈-alcoxi C₁₋₈-carbamoílo; aminotiocarbonilo; alcoxi C₁₋₈-carbonilo; halógenoalcoxi C₁₋₈-carbonilo; cicloalcoxi C₃₋₈-carbonilo; alcoxialquil C₂₋₈-carbonilo; halógenoalcoxialquil C₂₋₈-carbonilo; cicloalcoxialquil C₃₋₁₀-carbonilo; alquil C₁₋₈-aminocarbonilo; di-alquil C₁₋₈-aminocarbonilo; cicloalquil C₃₋₈-aminocarbonilo; alquil C₁₋₈-carboniloxi; halógenoalquil C₁₋₈-carboniloxi; cicloalquil C₃₋₈-carboniloxi; alquil C₁₋₈-carbonilamino; halógenoalquil C₁₋₈-carbonilamino; alquil C₁₋₈-aminocarboniloxi; di-alquil C₁₋₈-aminocarboniloxi; alquil C₁₋₈-oxicarboniloxi; alquil C₁₋₈-sulfinilo; halógenoalquil C₁₋₈-sulfinilo; alquil C₁₋₈-sulfonilo; halógenoalquil C₁₋₈-sulfonilo; alquil C₁₋₈-sulfoniloxi; halógenoalquil C₁₋₈-sulfoniloxi; alquil C₁₋₈-aminosulfamoílo; di-alquil C₁₋₈-aminosulfarmoílo; (alcoxi C₁₋₈-imino)-alquilo C₁₋₈; (cicloalcoxi C₃₋₇-imino)-alquilo C₁₋₈; hidroxiimino-alquilo C₁₋₈; (alcoxi C₁₋₈-imino)-cicloalquilo C₃₋₇; hidroxiimino-cicloalquilo C₃₋₇; (alquil C₁₋₈-imino)-oxi; (alquil C₁₋₈-imino)-oxi-alquilo C₁₋₈; (cicloalquil C₃₋₇-imino)-oxi-alquilo C₁₋₈; (alquil C₁₋₆-imino)-oxi-cicloalquilo C₃₋₇; (alquenil C₁₋₈-oxiimino)-alquilo C₁₋₈; (alquinil C₁₋₈-oxiimino)-alquilo C₁₋₈; (benciloxiimino)-alquilo C₁₋₈; alcoxialquilo C₁₋₈; alquiltioalquilo C₁₋₈; alcoxialcoxialquilo C₁₋₈; halógenoalcoxialquilo C₁₋₈; bencilo; fenilo; heteroarilo de 5 miembros; heteroarilo de 6 miembros; benciloxi; feniloxi; bencilsulfanilo; bencilamino; fenilsulfanilo; o fenilamino; R⁴ representa hidrógeno, flúor, alquilo C₁₋₈, haloalquilo C₁₋₈ o alquil C₁₋₈-oxi; R⁵ representa hidrógeno, flúor, alquilo C₁₋₈, haloalquilo C₁₋₈ o alquil C₁₋₈-oxi; o R⁴ y R⁵ forman, junto con el átomo de carbono al que están unidos, un anillo cicloalquilo C₃₋₇ opcionalmente sustituido con halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio; Q representa un ciclo aromático de 6 miembros de la fórmula (2) en donde U¹ representa CX¹ o N; en donde X¹ representa hidrógeno, halógeno, nitro, ciano, hidroxi, sulfanilo, carboxaldehído, carbaldehído O-(alquil C₁₋₈)oxima sustituida o no sustituida, grupo pentafluoro-l⁶-sulfenilo, alquilo C₁₋₈ sustituido o no sustituido, cicloalquilo C₃₋₈ sustituido o no sustituido, halógenocicloalquilo C₃₋₇ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno; cicloalquenilo C₃₋₇ sustituido o no sustituido; halógenoalquilo C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, un alquenilo C₂₋₈ sustituido o no sustituido, alquinilo C₂₋₈ sustituido o no sustituido, alcoxi C₁₋₈ sustituido o no sustituido, halógenoalcoxi C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfenilo sustituido o no sustituido, alquenil C₂₋₈-oxi sustituido o no sustituido, alquinil C₃₋₈-oxi sustituido o no sustituido, cicloalcoxi C₃₋₆ sustituido o no sustituido, N-(alcoxi C₁₋₈)-alcan C₁₋₈-imidoílo sustituido o no sustituido, N-(alcoxi C₁₋₈)-halógenoalcan C₁₋₈-imidoílo sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-aminocarbonilo; di-alquil C₁₋₈-aminocarbonilo, alcoxi C₁₋₈-carbonilo sustituido o no sustituido, alquil C₁₋₈-carboniloxi sustituido o no sustituido, alquil C₁₋₈-sulfinilo sustituido o no sustituido, alquil C₁₋₈-sulfonilo sustituido o no sustituido, (alcoxi C₁₋₈-imino)-alquilo C₁₋₈ sustituido o no sustituido; (cicloalcoxi C₃₋₇-imino)-alquilo C₁₋₈ sustituido o no sustituido; hidroxiimino-alquilo C₁₋₈ sustituido o no sustituido, feniloxi sustituido o no sustituido, fenilsulfenilo sustituido o no sustituido, arilo sustituido o no sustituido, tri(alquil C₁₋₈)-sililoxi sustituido o no sustituido, tri(alquil C₁₋₈)-sililo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterocicliloxi sustituido o no sustituido; U² representa CX² o N; en donde X² representa hidrógeno, halógeno, nitro, ciano, hidroxi, sulfanilo, carboxaldehído, carbaldehído O-(alquil C₁₋₈)oxima sustituida o no sustituida, grupo pentafluoro-l⁶-sulfenilo, alquilo C₁₋₈ sustituido o no sustituido, cicloalquilo C₃₋₈ sustituido o no sustituido, halógenocicloalquilo C₃₋₇ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno; cicloalquenilo C₃₋₇ sustituido o no sustituido; halógenoalquilo C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, un alquenilo C₂₋₈ sustituido o no sustituido, alquinilo C₂₋₈ sustituido o no sustituido, alcoxi C₁₋₈ sustituido o no sustituido, halógenoalcoxi C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfenilo sustituido o no sustituido, alquenil C₂₋₈-oxi sustituido o no sustituido, alquinil C₃₋₈-oxi sustituido o no sustituido, cicloalcoxi C₃₋₆ sustituido o no sustituido, N-(alcoxi C₁₋₈)-alcan C₁₋₈-imidoílo sustituido o no sustituido, N-(alcoxi C₁₋₈)-halógenoalcan C₁₋₈-imidoílo sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-aminocarbonilo; di-alquil C₁₋₈- aminocarbonilo, alcoxi C₁₋₈-carbonilo sustituido o no sustituido, alquil C₁₋₈-carboniloxi sustituido o no sustituido, alquil C₁₋₈-sulfinilo sustituido o no sustituido, alquil C₁₋₈-sulfonilo sustituido o no sustituido, (alcoxi C₁₋₈-imino)-alquilo C₁₋₈ sustituido o no sustituido; (cicloalcoxi C₃₋₇-imino)-alquilo C₁₋₈ sustituido o no sustituido; hidroxiimino-alquilo C₁₋₈ sustituido o no sustituido, feniloxi sustituido o no sustituido, fenilsulfenilo sustituido o no sustituido, arilo sustituido o no sustituido, tri(alquil C₁₋₈)-sililoxi sustituido o no sustituido, tri(alquil C₁₋₈)-sililo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterocicliloxi sustituido o no sustituido; U³ representa CX³ o N; en donde X³ representa hidrógeno, halógeno, nitro, ciano, hidroxi, sulfanilo, carboxaldehído, carbaldehído O-(alquil C₁₋₈)oxima sustituida o no sustituida, grupo pentafluoro-l⁶-sulfenilo, alquilo C₁₋₈ sustituido o no sustituido, cicloalquilo C₃₋₈ sustituido o no sustituido, halógenocicloalquilo C₃₋₇ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno; cicloalquenilo C₃₋₇ sustituido o no sustituido; halógenoalquilo C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, un alquenilo C₂₋₈ sustituido o no sustituido, alquinilo C₂₋₈ sustituido o no sustituido, alcoxi C₁₋₈ sustituido o no sustituido, halógenoalcoxi C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfenilo sustituido o no sustituido, alquenil C₂₋₈-oxi sustituido o no sustituido, alquinil C₃₋₈-oxi sustituido o no sustituido, cicloalcoxi C₃₋₆ sustituido o no sustituido, N-(alcoxi C₁₋₈)-alcan C₁₋₈-imidoílo sustituido o no sustituido, N-(alcoxi C₁₋₈)-halógenoalcan C₁₋₈-imidoílo sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-aminocarbonilo; di-alquil C₁₋₈-aminocarbonilo, alcoxi C₁₋₈-carbonilo sustituido o no sustituido, alquil C₁₋₈-carboniloxi sustituido o no sustituido, alquil C₁₋₈-sulfinilo sustituido o no sustituido, alquil C₁₋₈-sulfonilo sustituido o no sustituido, (alcoxi C₁₋₈-imino)-alquilo C₁₋₈ sustituido o no sustituido; (cicloalcoxi C₃₋₇-imino)-alquilo C₁₋₈ sustituido o no sustituido; hidroxiimino-alquilo C₁₋₈ sustituido o no sustituido, feniloxi sustituido o no sustituido, fenilsulfenilo sustituido o no sustituido, arilo sustituido o no sustituido, tri(alquil C₁₋₈)-sililoxi sustituido o no sustituido, tri(alquil C₁₋₈)-sililo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterocicliloxi sustituido o no sustituido; U⁴ representa CX⁴ o N; en donde X⁴ representa hidrógeno, halógeno, nitro, ciano, hidroxi, sulfanilo, carboxaldehído, carbaldehído O-(alquil C₁₋₈)oxima sustituida o no sustituida, grupo pentafluoro-l⁶-sulfenilo, alquilo C₁₋₈ sustituido o no sustituido, cicloalquilo C₃₋₈ sustituido o no sustituido, halógenocicloalquilo C₃₋₇ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno; cicloalquenilo C₃₋₇ sustituido o no sustituido; halógenoalquilo C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, un alquenilo C₂₋₈ sustituido o no sustituido, alquinilo C₂₋₈ sustituido o no sustituido, alcoxi C₁₋₈ sustituido o no sustituido, halógenoalcoxi C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfenilo sustituido o no sustituido, alquenil C₂₋₈-oxi sustituido o no sustituido, alquinil C₃₋₈-oxi sustituido o no sustituido, cicloalcoxi C₃₋₆ sustituido o no sustituido, N-(alcoxi C₁₋₈)-alcan C₁₋₈-imidoílo sustituido o no sustituido, N-(alcoxi C₁₋₈)-halógenoalcan C₁₋₈-imidoílo sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-aminocarbonilo; di-alquil C₁₋₈-aminocarbonilo, alcoxi C₁₋₈-carbonilo sustituido o no sustituido, alquil C₁₋₈-carboniloxi sustituido o no sustituido, alquil C₁₋₈-sulfinilo sustituido o no sustituido, alquil C₁₋₈-sulfonilo sustituido o no sustituido, (alcoxi C₁₋₈-imino)-alquilo C₁₋₈ sustituido o no sustituido; (cicloalcoxi C₃₋₇-imino)-alquilo C₁₋₈ sustituido o no sustituido; hidroxiimino-alquilo C₁₋₈ sustituido o no sustituido, feniloxi sustituido o no sustituido, fenilsulfenilo sustituido o no sustituido, arilo sustituido o no sustituido, tri(alquil C₁₋₈)-sililoxi sustituido o no sustituido, tri(alquil C₁₋₈)-sililo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterocicliloxi sustituido o no sustituido; U⁵ representa CX⁵ o N; en donde X⁵ representa hidrógeno, halógeno, nitro, ciano, hidroxi, sulfanilo, carboxaldehído, carbaldehído O-(alquil C₁₋₈)oxima sustituida o no sustituida, grupo pentafluoro-l⁶-sulfenilo, alquilo C₁₋₈ sustituido o no sustituido, cicloalquilo C₃₋₈ sustituido o no sustituido, halógenocicloalquilo C₃₋₇ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno; cicloalquenilo C₃₋₇ sustituido o no sustituido; halógenoalquilo C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, un alquenilo C₂₋₈ sustituido o no sustituido, alquinilo C₂₋₈ sustituido o no sustituido, alcoxi C₁₋₈ sustituido o no sustituido, halógenoalcoxi C₁₋₈ sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-sulfenilo sustituido o no sustituido, alquenil C₂₋₈-oxi sustituido o no sustituido, alquinil C₃₋₈-oxi sustituido o no sustituido, cicloalcoxi C₃₋₆ sustituido o no sustituido, N-(alcoxi C₁₋₈)-alcan C₁₋₈-imidoílo sustituido o no sustituido, N-(alcoxi C₁₋₈)-halógenoalcan C₁₋₈-imidoílo sustituido o no sustituido que tiene 1 a 5 átomos de halógeno, alquil C₁₋₈-aminocarbonilo; di-alquil C₁₋₈-aminocarbonilo, alcoxi C₁₋₈-carbonilo sustituido o no sustituido, alquil C₁₋₈-carboniloxi sustituido o no sustituido, alquil C₁₋₈-sulfinilo sustituido o no sustituido, alquil C₁₋₈-sulfonilo sustituido o no sustituido, (alcoxi C₁₋₈-imino)-alquilo C₁₋₈ sustituido o no sustituido; (cicloalcoxi C₃₋₇-imino)-alquilo C₁₋₈ sustituido o no sustituido; hidroxiimino-alquilo C₁₋₈ sustituido o no sustituido, feniloxi sustituido o no sustituido, fenilsulfenilo sustituido o no sustituido, arilo sustituido o no sustituido, tri(alquil C₁₋₈)-sililoxi sustituido o no sustituido, tri(alquil C₁₋₈)-sililo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterocicliloxi sustituido o no sustituido; y en donde a lo sumo dos de U¹, U², U³, U⁴ o U⁵ pueden representar N; o U¹ y U² o U² y U³ o U³ y U⁴ forman juntos un anillo adicional saturado o insaturado de 4 a 6 miembros sustituido con halógeno o alquilo C₁₋₈ o no sustituido; y sus sales o N-óxidos. Reivindicación 11: Los compuestos de la fórmula (3) en donde R¹ representa hidrógeno, en cada caso opcionalmente ramificado alquilo C₁₋₈, haloalquilo C₁₋₈, alquenilo C₂₋₇, haloalquenilo C₂₋₇, alquinilo C₂₋₈, haloalquinilo C₂₋₈, cicloalquilo C₃₋₇ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio, bicicloalquilo opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquil C₁₋₄-tio o haloalquil C₁₋₄-tio, cicloalquilalquilo C₃₋₈ opcionalmente sustituido con halógeno, ciano, alquilo C₁₋₄, haloalquilo
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| EP2308866A1 (de) | 2009-10-09 | 2011-04-13 | Bayer CropScience AG | Phenylpyri(mi)dinylpyrazole und ihre Verwendung als Fungizide |
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| CA2825098C (en) | 2011-01-27 | 2020-03-10 | Universite De Montreal | Pyrazolopyridine and pyrazolopyrimidine derivatives as melanocortin-4 receptor modulators |
| EP2723734A1 (en) | 2011-06-22 | 2014-04-30 | Isochem | Process for the preparation of solifenacin and salts thereof |
| EP2782447A1 (de) | 2011-11-25 | 2014-10-01 | Bayer Intellectual Property GmbH | 2-iod-imidazol-derivate |
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-
2016
- 2016-03-29 CR CR20170445A patent/CR20170445A/es unknown
- 2016-03-29 EP EP16711859.5A patent/EP3277666A1/en not_active Withdrawn
- 2016-03-29 WO PCT/EP2016/056764 patent/WO2016156290A1/en not_active Ceased
- 2016-03-29 CN CN201680027971.2A patent/CN107635968A/zh active Pending
- 2016-03-29 KR KR1020177031654A patent/KR20170132315A/ko not_active Withdrawn
- 2016-03-29 PE PE2017001646A patent/PE20180175A1/es unknown
- 2016-03-29 JP JP2017551271A patent/JP2018516237A/ja active Pending
- 2016-03-29 EA EA201792151A patent/EA201792151A1/ru unknown
- 2016-03-29 US US15/563,414 patent/US10231453B2/en not_active Expired - Fee Related
- 2016-03-29 BR BR112017021183A patent/BR112017021183A2/pt not_active Application Discontinuation
- 2016-03-29 CA CA2981379A patent/CA2981379A1/en not_active Abandoned
- 2016-03-29 MX MX2017012709A patent/MX2017012709A/es unknown
- 2016-03-29 AU AU2016239067A patent/AU2016239067A1/en not_active Abandoned
- 2016-03-31 TW TW105110209A patent/TW201702229A/zh unknown
- 2016-04-04 AR ARP160100901A patent/AR104178A1/es unknown
- 2016-04-04 UY UY0001036603A patent/UY36603A/es not_active Application Discontinuation
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2017
- 2017-09-28 IL IL254773A patent/IL254773A0/en unknown
- 2017-09-29 PH PH12017501808A patent/PH12017501808A1/en unknown
- 2017-10-02 EC ECIEPI201765502A patent/ECSP17065502A/es unknown
- 2017-10-02 CL CL2017002480A patent/CL2017002480A1/es unknown
- 2017-10-02 CO CONC2017/0010006A patent/CO2017010006A2/es unknown
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- 2017-11-01 ZA ZA2017/07424A patent/ZA201707424B/en unknown
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2018
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Also Published As
| Publication number | Publication date |
|---|---|
| EP3277666A1 (en) | 2018-02-07 |
| PH12017501808A1 (en) | 2018-04-23 |
| ECSP17065502A (es) | 2017-10-31 |
| IL254773A0 (en) | 2017-12-31 |
| CL2017002480A1 (es) | 2018-05-11 |
| CN107635968A (zh) | 2018-01-26 |
| CR20170445A (es) | 2018-02-06 |
| EA201792151A1 (ru) | 2018-04-30 |
| KR20170132315A (ko) | 2017-12-01 |
| TW201702229A (zh) | 2017-01-16 |
| US20180084780A1 (en) | 2018-03-29 |
| AU2016239067A1 (en) | 2017-10-19 |
| ZA201707424B (en) | 2019-07-31 |
| WO2016156290A1 (en) | 2016-10-06 |
| PE20180175A1 (es) | 2018-01-22 |
| MX2017012709A (es) | 2017-11-23 |
| GT201700210A (es) | 2018-12-06 |
| US10568326B2 (en) | 2020-02-25 |
| CO2017010006A2 (es) | 2018-01-05 |
| US20190082691A1 (en) | 2019-03-21 |
| US10231453B2 (en) | 2019-03-19 |
| BR112017021183A2 (pt) | 2018-07-03 |
| JP2018516237A (ja) | 2018-06-21 |
| CA2981379A1 (en) | 2016-10-06 |
| UY36603A (es) | 2016-10-31 |
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