DK2831046T3 - N-cyclylamider som nematicider - Google Patents

N-cyclylamider som nematicider Download PDF

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DK2831046T3
DK2831046T3 DK13707636.0T DK13707636T DK2831046T3 DK 2831046 T3 DK2831046 T3 DK 2831046T3 DK 13707636 T DK13707636 T DK 13707636T DK 2831046 T3 DK2831046 T3 DK 2831046T3
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spp
trifluoromethyl
cis
cyclobutyl
phenyl
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DK13707636.0T
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Anthony Cornelius O'sullivan
Olivier Loiseleur
Roman Staiger
Torsten Luksch
Thomas Pitterna
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Syngenta Participations Ag
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    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • 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
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    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/37—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
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    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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    • C07D213/00—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
    • 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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    • 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
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Claims (21)

1 . Fnrhi ndslrp med formel (I)
(i), hvor Y er 0, C=0 eller CR12R13; A er en 5- eller 6-leddet heteroaromatisk ring, der indeholder 1 til 3 heteroatomer, der hver for sig er udvalgt uafhængigt blandt oxygen, nitrogen og svovl, eller en phenylring; hvilken heteroaromatiske ring eller phenyl eventuelt er substitueret med en eller flere R6; R6 hver for sig er halogen, cyano, Cl-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, C1-C4- haloalkylthio, Cl-C4-alkoxy-Cl-4-alkyl eller Cl-C4-haloalkoxy-Cl-C4-alkyl; RI, R2, R3, R4, R12 og R13 hver for sig er hydrogen, halogen, cyano, Cl-C4-alkyl, Cl-C4-alkoxy eller Cl-C4-haloalkyl, R5 er hydrogen, methoxy eller hydroxyl, B er phenyl substitueret med en eller flere R8, R8 hver for sig er halogen, cyano eller en group -L-R9, hvor hvert L hver for sig er en binding, -0-, -0C(0)-, -NR7-, NR7C0-, -NR7S(0)n-, -S(0)n-, - S(0)nNR7-, -C00- eller C0NR7-, n er 0, 1 eller 2, R7 er hydrogen, Cl-C4-alkyl, Cl-C4-haloalkyl, benzyl eller phenyl, hvor benzyl og phenyl er usubstitueret eller substitueret med halogen, cyano, Cl-C4-alkyl eller C1-C4-haloalkyl, R9 hver for sig er Cl-C6-alkyl, der er usubstitueret eller substitueret med en eller flere RIO, C3-C6-cycloalkyl, der er usubstitueret eller substitueret med en eller flere RIO, C6-C14-bicycloalkyl, der er usubstitueret eller substitueret med en eller flere RIO, C2-C6-alkenyl, der er usubstitueret eller substitueret med en eller flere RIO, C2-C6-alkynyl, der er usubstitueret eller substitueret med en eller flere RIO, phenyl, der er usubstitueret eller substitueret med RIO, eller heteroaryl, der er usubstitueret eller substitueret med en eller flere RIO, RIO hver for sig er halogen, cyano, Cl-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio, Cl-C4-haloalkylthio, C3-C6-alkenyloxy eller C3-C6-alkynyloxy; eller et salt eller N-oxid deraf; hvor B og A-CO-NR5 er cis i forhold til hinanden på den 4-leddede ring, eller en tautomer eller stereoisomer af disse forbindelser.
2. Forbindelse ifølge krav 1, hvor Y er 0 eller CH2; A er en 6-leddet heteroaromatisk ring, der indeholder 1 til 2 nitrogenatomer, eller en phenylring; hvilken heteroaromatiske ring eller phenyl eventuelt er substitueret med en eller flere R6; R6 hver for sig er halogen, cyano, Cl-C4-alkyl, C1-C4-haloalkyl eller Cl-C4-haloalkoxy; RI, R2, R3, R4 og R5 hver er hydrogen; B er phenyl substitueret med en eller flere R8; R8 hver for sig er udvalgt blandt halogen, cyano, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-haloalkoxy eller C3-C6-cycloalkyl.
3. Forbindelse ifølge et hvilket som helst af krav 1 eller krav 2, hvor A er en 6-leddet heteroaromatisk ring, der indeholder 1 til 2 nitrogenatomer og har 1 til 3 substituenter, der er udvalgt blandt R6, eller en phenylring, der har 1 eller 3 substituenter, der er udvalgt blandt R6.
4. Forbindelse ifølge et hvilket som helst af kravene 1 til 3, hvor B er en phenyl substitueret med 1 til 3 substituenter R8 .
5. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, hvor B er en phenyl substitueret med 1 til 3 substituenter, der er udvalgt uafhængigt blandt fluor, chlor, trifluormethyl, cyclopropyl, difluormethoxy og trifluormethoxy; A er en phenyl, pyridyl eller pyrazinyl, hvilke ringe hver for sig er usubstitueret eller substitueret med 1 til 3 substituenter, der er udvalgt uafhængigt blandt chlor, brom, fluor, methyl, cyano og trifluormethyl, Y er 0 eller CH2, og RI, R2, R3, R4 og R5 hver er hydrogen.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor Y er CH2; B er en mono- eller dihalogensubstitueret phenyl; A er udvalgt blandt phenyl, pyrazinyl og pyridyl, der hver er mono- eller disubstitueret med substituenter, der er udvalgt uafhængigt blandt halogen og Cl-C4-haloalkyl; RI, R2, R3, R4 og R5 hver er hydrogen.
7. Forbindelse ifølge krav 1, hvor forbindelsen er udvalgt blandt en hvilken som helst af forbindelserne 1 til 118 med formel (Id)
(Id) eller et salt eller N-oxid deraf; hvor Y, R9a, R9b, R9c og A er som defineret i følgende tabel:
og hvor en hvilken som helst af R9a, R9b og R9c er hydrogen, med mindre andet er defineret; eller en tautomer eller stereoisomer af disse forbindelser.
8. Forbindelse eller salt eller N-oxid deraf ifølge krav 1, der er udvalgt blandt N-[(1,2-cis)-2-(4-chlorphenyl)cyclobutyl]-2-(trifluormethyl)pyridin-3-carboxamid; N-[(1,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]-2,6- difluorbenzamid; N-[ (1,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]-2-(trifluormethyl)benzamid; N-[(1,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]-2-(trifluormethyl)pyridin-3-carboxamid; N-[(l,2-cis)-2-(2,4-difluorphenyl)cyclobutyl]-2-(trifluormethyl)benzamid; N-[(l,2-cis)-2-(2,4-difluorphenyl)cyclobutyl]-2-(trifluormethyl)pyridin-3-carboxamid; N-[(l,2-cis)-2-(2,4-difluorphenyl)cyclobutyl]-3-(trifluormethyl)pyrazin-2-carboxamid; N-[(1,2-cis)-2-[2-chlor-4-(trifluormethyl)phenyl]cyclobutyl]-3-(trifluormethyl)pyridin-2-carboxamid; N- [ (1,2-cis)-2-[2-chlor-4-(trifluormethyl)phenyl]cyclobutyl]- 2- (trifluormethyl)pyridin-3-carboxamid; N-[ (1,2-cis)-2-[2-chlor-4-(trifluormethyl)phenyl]cyclobutyl]- 3- (trifluormethyl)pyrazin-2-carboxamid; N-[(1,2-cis)-2-[2-fluor-4-(trifluormethyl)phenyl]cyclobutyl]- 2- (trifluormethyl)benzamid; N-[(l,2-cis)-2-[2-fluor-4-(trifluormethyl)phenyl]cyclobutyl]- 3- (trifluormethyl)pyridin-2-carboxamid; N-[(1,2-cis)-2-[2-fluor-4-(trifluormethyl) phenyl]cyclobutyl]- 2- (trifluormethyl)pyridin-3-carboxamid; N-[(l,2-cis)-2-[2-fluor-4-(trifluormethyl)phenyl]cyclobutyl]- 3- (trifluormethyl)pyrazin-2-carboxamid; 2- (trifluormethyl)-N-[(2,3-cis)-2-(2,4,6-trifluorphenyl)oxetan-3-yl]benzamid; 2, 6-difluor-N-[(2,3-cis)-2-(2,4,6-trifluorphenyl)oxetan-3-yl]benzamid; N-[(2,3-cis)-2-(2,4-difluorphenyl)oxetan-3-yl]-2-(trifluormethyl)benzamid; N-[(2,3-cis)-2-(2,4-difluorphenyl)oxetan-3-yl]-2-(trifluormethyl)pyridin-3-carboxamid; 3- chlor-N-[(1,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]pyrazin- 2- carboxamid; N-[(1,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]-3-(trifluormethyl)pyridin-2-carboxamid; 3- chlor-N-[(l,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]pyridin- 2- carboxamid; N-[(1,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]-2-methylpyridin- 3- carboxamid; N-[(1,2-cis)-2-(2,4-dichlorphenyl)cyclobutyl]-3-methylpyridin-2-carboxamid; N-[(1,2-cis)-2-(2,4-difluorphenyl)cyclobutyl]-2-(trifluormethyl)pyridin-3-carboxamid; 2-chlor-N-[(1,2-cis)-2-(2,4-dichlorphenyl)-cyclobutyl]-nicotinamid; N-[(1,2-cis)-2-(2-chlor-4-fluorphenyl)cyclobutyl]-2-(trifluormethyl)pyridin-3-carboxamid; N-[(1,2-cis)-2-(2-chlor-4-fluorphenyl)cyclobutyl]-3-(trifluormethyl)pyridin-2-carboxamid; N-[(1,2-cis)-2-(4-brom-2-chlorphenyl)cyclobutyl]-3-(trifluormethyl)pyridin-2-carboxamid; N-[(1,2-cis)-2-(2,4-difluorphenyl)cyclobutyl]-3-(trifluormethyl)pyridin-2-carboxamid; N-[(1,2-cis)-2-(4-methoxyphenyl)cyclobutyl]-3-(trifluormethyl)pyridin-2-carboxamid; N-[(1,2-cis)-2-(4-chlor-2-fluorphenyl)cyclobutyl]-3-(trifluormethyl)pyridin-2-carboxamid; og N-[(1,2-cis)-2-(2-chlor-4-fluorphenyl)cyclobutyl]-2-(trifluormethyl)benzamid; eller en tautomer eller stereoisomer af disse forbindelser.
9. Pesticidsammensætning, der foruden at omfatte formuleringsadjuvanser omfatter en pesticidvirkende effektiv mængde af en forbindelse med formel I ifølge et hvilket som helst af kravene 1 til 8.
10. Sammensætning ifølge krav 9, der yderligere omfatter et eller flere andre insekticidt, acaricidt, nematicidt og/eller fungicidt aktive midler.
11. Fremgangsmåde til bekæmpelse af skade og/eller udbyttetab forårsaget af et skadedyr og/eller svamp, der omfatter påføring på et skadedyr eller på en plante, der er modtagelig for angreb af et skadedyr og/eller svamp, eller på voksestedet derfor eller på et planteopformeringsmateriale af en effektiv mængde af en forbindelse ifølge et hvilket som helst af kravene 1 til 8 eller en sammensætning ifølge et hvilket som helst af krav 9 eller 10.
12. Fremgangsmåde til beskyttelse af planteopformeringsmateriale mod skade og/eller udbyttetab forårsaget af et skadedyr og/eller svamp, der omfatter påføring på planteopformeringsmaterialet eller stedet, hvor opformeringsmaterialet plantes, af en effektiv mængde af en forbindelse ifølge et hvilket som helst af kravene 1 til 8 eller en sammensætning ifølge et hvilket som helst af krav 9 eller 10.
13. Fremgangsmåde ifølge et hvilket som helst af krav 11 eller krav 12, hvor skaden eller tabet er forårsaget af et nematodeangreb.
14. Belagt planteopformeringsmateriale, hvor belægningen på planteopformeringsmaterialet omfatter en forbindelse ifølge et hvilket som helst af kravene 1 til 8.
15. Farmaceutisk sammensætning til bekæmpelse af helminter, spindeldyr eller endo- eller ektoparasitiske artropoder, der omfatter en forbindelse ifølge et hvilket som helst af kravene 1 til 8, et fysiologisk tolerabelt bæremateriale og eventuelt et eller flere almindelige formuleringshjælpestoffer.
16. Farmaceutisk sammensætning, der omfatter en forbindelse ifølge et hvilket som helst af kravene 1 til 8, et fysiologisk tolerabelt bæremateriale og eventuelt et eller flere almindelige formuleringshjælpestoffer, til forebyggelse af infektion med sygdomme, der overføres via helminter, spindeldyr eller endo- eller ektoparasitiske artropoder.
17. Sammensætning ifølge krav 15 eller 16, der yderligere omfatter en eller flere andre biologisk aktive forbindelser.
18. Forbindelse ifølge et hvilket som helst af kravene 1 til 8 til bekæmpelse og forebyggelse af endo- og ektoparasitiske nematodeangreb og infektioner hos varmblodede dyr, der omfatter injektion, topisk påføring eller oral administration af en sammensætning ifølge krav 15 eller 16.
19. Fremgangsmåde til fremstilliing af en forbindelse med formel I ifølge krav 1, der omfatter reaktion af en forbindelse med formel II
(II), hvori B, Y, Ri, R2, R3, R4 og R5 er som defineret i krav 1, med et acyleringsmiddel med formel III A-C(=0)-R* (III), hvori A er som defineret i krav 1, og R* er halogen, hydroxyl eller Ci_6-alkoxy, i nærvær af en base.
20. Forbindelser med formel (XlXa)
(XlXa) hvori B, Y, RI, R3 og R4 er som defineret i krav 1, hvor forbindelserne med formlerne oe h
er udelukket.
21. Forbindelser med formel (II)
(II) hvori B, Y, RI, R2, R3, R4 og R5 er som defineret i krav 1, hvor forbindelsen med formel
er udelukket.
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JP2015514077A (ja) 2015-05-18
KR101952701B1 (ko) 2019-02-27
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AR090488A1 (es) 2014-11-19
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CA2866227A1 (en) 2013-10-03
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