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HRP20151058T2 - Ariloazol-2-il-cijanoetilamino-spojevi, postupak njihove proizvodnje i postupak njihove uporabe - Google Patents

Ariloazol-2-il-cijanoetilamino-spojevi, postupak njihove proizvodnje i postupak njihove uporabe Download PDF

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HRP20151058T2
HRP20151058T2 HRP20151058TT HRP20151058T HRP20151058T2 HR P20151058 T2 HRP20151058 T2 HR P20151058T2 HR P20151058T T HRP20151058T T HR P20151058TT HR P20151058 T HRP20151058 T HR P20151058T HR P20151058 T2 HRP20151058 T2 HR P20151058T2
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alkyl
halo
compound
alkoxy
cyano
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Mark David Soll
Loic Patrick Le Hir De Fallois
Scot Kevin Huber
Hyoung Ik Lee
Douglas Edward Wilkinson
Robert Toms Jacobs
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Merial, Inc.
Aventis Agriculture
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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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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Claims (20)

1. Spoj, naznačen time, da je to ariloazol-2-il-cijanoetilamin formule (I): [image] P je C-R1 ili N; Q je C-R2 ili N; V je C-R8 ili N; W je C-R9 ili N; X je C-R10 ili N; Y je C-R11 ili N; bilo koji od R1, R2, R8, R9, R10 i R11, međusobno neovisno je vodik, amino, amido, cijano, nitro, halogen, alkil, alkenil, alkinil, cikloalkil, hidroksialkil, haloalkil, alkiltio, haloalkiltio, ariltio, alkoksi, fenoksi, alkoksialkoksi, cikloalkiloksi, haloalkoksi, alkilkarbonil, haloalkilkarbonil, alkilsulfinil, haloalkilsulfinil, alkilsulfonil, alkilamino, di(alkil)amino, alkilkarbonilamino, alkilaminoalkoksi, dialkilaminoalkoksi, alkilaminoalkil, dialkilaminoalkil, aminoalkil, formil, HO2C-, alkil-O2C-, nesupstituiran ili supstituiran aril ili nesupstituiran ili supstituiran fenoksi, gdje supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, alkil, haloalkil, alkiltio, haloalkiltio, ariltio, alkoksi, haloalkoksi, alkilkarbonil, haloalkilkarbonil, alkilsulfinil, haloalkilsulfinil, alkilsulfonil, haloalkilsulfonil; bilo koji od R3, R4 i R5, međusobno neovisno je vodik, halogen, alkil, hidroksialkil, alkiltioalkil, haloalkil, alkiloksialkil, alkilsulfinilalkil, alkilsulfonilalkil, alkilsulfoniloksialkil; nesupstituiran ili supstituiran cikloalkil, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: halogen i alkil; nesupstituiran ili supstituiran fenil, gdje svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, alkil, haloalkil, alkiltio, haloalkiltio, ariltio, alkoksi, haloalkoksi, alkilkarbonil, haloalkilkarbonil, alkilsulfinil, haloalkilsulfinil, alkilsulfonil, haloalkilsulfonil, alkilamino, di(alkil)amino; ili R4 i R5 zajedno s ugljikom na kojega su priključeni, tvore cikloalkil-prsten; R6 je vodik, alkil, alkoksialkil, alkilkarbonil, alkiltiokarbonil ili nesupstituiran ili supstituiran benzil, gdje svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, alkil, haloalkil, alkiltio, haloalkiltio, ariltio, alkoksi, haloalkoksi, alkilkarbonil, haloalkilkarbonil, alkilsulfinil, haloalkilsulfinil, alkilsulfonil, haloalkilsulfonil, alkilamino, di(alkil)amino; R7 je vodik, alkil, alkoksialkil, alkilkarbonil, alkiltiokarbonil ili nesupstituiran ili supstituiran fenil, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, alkil, haloalkil, fenil, fenoksi, alkiltio, haloalkiltio, ariltio, alkoksi, haloalkoksi, alkilkarbonil, haloalkilkarbonil, alkilsulfinil, haloalkilsulfinil, alkilsulfonil, haloalkilsulfonil-alkilamino, di(alkil)amino; nesupstituiran ili supstituiran hetaril, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, alkil, haloalkil, alkiltio, haloalkiltio, ariltio, alkoksi, haloalkoksi, alkilkarbonil, haloalkilkarbonil, alkilsulfinil, haloalkilsulfinil, alkilsulfonil, alkilamino, di(alkil)amino; ili nesupstituiran ili supstituiran naftil ili kinolin, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, alkil, haloalkil, alkiltio, haloalkiltio, ariltio, alkoksi, haloalkoksi, alkilkarbonil, haloalkilkarbonil, alkilsulfinil, haloalkilsulfinil, alkilsulfonil, alkilamino, di(alkil)amino; Z je direktna veza, C(O), C(S) ili S(O)p; a je 1, 2 ili 3; p je 0, 1 ili 2; i njegove soli.
2. Ariloazol-2-il-cijanoetilamin prema zahtjevu 1, naznačen time, da P je C-R1 ili N; Q je C-R2 ili N; V je C-R8 ili N; W je C-R9 ili N; X je C-R10 ili N; Y je C-R11 ili N; bilo koji od R1, R2, R8, R9, R10 i R11, međusobno neovisno je vodik, amino, amido, cijano, nitro, halogen, C1-C6-alkil, C2-C6-alkenil, C2-C6-akinil, C3-C7-cikloalkil, hidroksi-C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltioariltio, C1-C8-alkoksi, fenoksi, C1-C6-alkoksi-C1-C6-alkoksi, C3-C7-cikloalkiloksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino, C1-C6-alkilkarboksilamino, C1-C6-alkilamino-C1-C6-alkoksi, di-C1-C6-alkilamino-C1-C6-alkoksi, C1-C6-alkilamino-C1-C6-alkil, di-C1-C6-alkilamino-C1-C6-alkil, amino-C1-C6-alkil, formil, HO2C-, C1-C6-alkil-O2C-, nesupstituiran ili supstituiran aril ili nesupstituiran ili supstituiran fenoksi, gdje svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfnil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, halo-C1-C6-alkilsulfonil; bilo koji od R3, R4 i R5, međusobno neovisno je vodik, halogen, C1-C6-alkil, hidroksi-C1-C6-alkil, C1-C6-alkiltio-C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkoksi-C1-C6-alkil, C1-C6-alkilsulfinil-C1-C6-alkil, C1-C6-alkilsulfonil-C1-C6-alkil, C1-C6-alkilsulfoniloksi-C1-C6-alkil; nesupstituiran ili supstituiran C3-C7-cikloalkil, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: halogen i C1-C6-alkil; nesupstituiran ili supstituiran fenil, gdje svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkil-karbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, halo-C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino; ili R4 i R5 zajedno s ugljikom na kojega su priključeni, tvore cikloalkil-prsten; R6 je vodik, C1-C6-alkil, C1-C6-alkoksi-C1-C6-alkil, C1-C6-alkilkarbonil, C1-C6-alkiltiokarbonil ili nesupstituiran ili supstituiran benzil, gdje svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, halo-C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino; R7 je vodik, C1-C6-alkil, C1-C6-alkoksi-C1-C6-alkil, C1-C6-alkilkarbonil, C1-C6-alkiltiokarbonil ili nesupstituiran ili supstituiran fenil, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, fenil, fenoksi, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, halo-C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino; nesupstituiran ili supstituiran hetaril, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino; ili nesupstituiran ili supstituiran naftil ili kinolil, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino; Z je direktna veza, C(O), C(S) ili S(O)p; a je 1, 2 ili 3; p je 0, 1 ili 2; i njegove soli.
3. Ariloazol-2-il-cijanoetilamin prema zahtjevu 2, naznačen time, da P i Q su N; V je C-R8; W je C-R9; X je C-R10; Y je C-R11; bilo koji od R8, R9, R10 i R11, međusobno neovisno je vodik, amino, amido, cijano, nitro, halogen, C1-C6-alkil, C2-C6-alkenil, C2-C6-akinil, C3-C7-cikloalkil, hidroksi-C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltioariltio, C1-C6-alkoksi, fenoksi, C1-C6-alkoksi-C1-C6-alkoksi, C3-C7-cikloalkiloksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino, C1-C6-alkilkarboksilamino, C1-C6-alkilamino-C1-C6-alkoksi, di-C1-C6-alkilamino-C1-C6-alkoksi, C1-C6-alkilamino-C1-C6-alkil, di-C1-C6-alkilamino-C1-C6-alkil, amino-C1-C8-alkil, formil, HO2C-, C1-C6-alkil-O2C-, nesupstituiran ili supstituiran aril ili nesupstituiran ili supstituiran fenoksi, gdje svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, halo-C1-C6-alkilsulfonil; R3, R4 i R6 su H; R5 je metil; R7 je nesupstituiran ili supstituiran fenil, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino; nesupstituiran ili supstituiran hetaril, pri čemu svi supstituenti mogu biti međusobno neovisni i odabrani su iz skupine koju čine: cijano, nitro, halogen, C1-C6-alkil, halo-C1-C6-alkil, C1-C6-alkiltio, halo-C1-C6-alkiltio, ariltio, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkilkarbonil, halo-C1-C6-alkilkarbonil, C1-C6-alkilsulfinil, halo-C1-C6-alkilsulfinil, C1-C6-alkilsulfonil, C1-C6-alkilamino, di(C1-C6-alkil)amino; Z je C(O); i a je 1; i njegove soli.
4. Ariloazol-2-il-cijanoetilamin prema zahtjevu 1, naznačen time, da P i Q su N; V je C-R8; W je C-R9; X je C-R10; Y je C-R11; R3, R4 i R6 su vodik; R5 je vodik, C1-C6-alkil, halo-C1-C6-alkil, hidroksi-C1-C6-alkil, C1-C6-alkiltio-C1-C6-alkil, C1-C6-alkiloksi-C1-C6-alkil, ili C1-C6-alkilsulfoniloksi-C1-C6-alkil; R7 je nesupstituiran fenil ili fenil supstituiran s jednim ili više supstituenata odabranih iz skupine koju čine: C1-C6-alkil, halo-C1-C6-alkil, fenil, feniloksi, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkiltio, halo-C1-C6-alkiltio, halo-C1-C6-alkilsulfinil i halo-C1-C6-alkilsulfonil; bilo koji od R8, R9, R10 i R11, međusobno neovisno je vodik, halogen, C1-C6-alkil, halo-C1-C6-alkil, cijano, C1-C6-alkoksi, halo-C1-C6-alkoksi, C1-C6-alkenil, C1-C6-alkilamino, hidroksi-C1-C6-alkil, formil, C1-C6-alkilamino-C1-C6-alkil, HO2C-, C1-C6-alkil-O2C- ili nesupstituiran ili supstituiran fenil, pri čemu su supstituenti C1-C6-alkil ili halo-C1-C6-alkil; Z je C(O); a je 1; i njegove soli.
5. Ariloazol-2-il-cijanoetilamin prema zahtjevu 1, naznačen time, da P i Q su N; V je C-R8; W je C-R9; X je C-R10; Y je C-R11; R3, R4 i R6 su vodik; R5 je metil, etil, butil, CH2OH, CH2OCH3, CH2SCH3, CH2OSO2CH3; R7 je fenil supstituiran sa sljedećima: butil, CF3, fenil, fenoksi, OCF3, SCF3, SOCF3, SO2CF3; bilo koji od R8, R9, R10 i R11, međusobno neovisno je vodik, metil, CH2NH2, CH2N(CH3)2, vinil, CH2OH, CH(OH)CH2OH, CO2H, CO2CH3, Ph-CF3, F, Cl, Br, CF3, OCF3 ili CN; Z je C(O); a je 1; i njegove soli.
6. Ariloazol-2-il-cijanoetilamin prema zahtjevu 1, naznačen time, da P je N; Q je C-R2; V je C-R6; W je C-R9; X je C-R10; Y je C-R11; R2 je vodik, Cl, metil, metoksi, etoksi, propoksi, butoksi, O(CH2)2OCH3 ili O(CH2)2N(CH3)2; R3, R4 i R6 su vodik; R5 je metil; R7 je fenil supstituiran s OCF3, fenoksi ili SCF3; bilo koji od R8, R9, R10 i R11, međusobno neovisno je vodik, Cl, Br, C1-C6-alkil, CF3, nitro, amino, amido, CO2CH3 ili NHCOCH3; Z je C(O); a je 1; i njegove soli.
7. Ariloazol-2-il-cijanoetilamin prema zahtjevu 1, naznačen time, da P je N; Q je C-R2 ili N; V je N; W je C-R9; X je C-R10; Y je C-R11; R2 je vodik, Cl, Br, metoksi; R3, R4 i R8su vodik; R5 je metil; R7 je fenil supstituiran s OCF3 ili SCF3; bilo koji od R9, R10 i R11, međusobno neovisno je vodik, Cl, Br ili metil; Z je C(O); i a je 1; i njegove soli.
8. Pesticidni sastav, naznačen time, da obuhvaća spoj prema zahtjevu 1 i pesticidno prikladan nosač.
9. Pesticidni sastav prema zahtjevu 8, naznačen time, da nadalje obuhvaća dodatni pesticidni spoj.
10. Postupak proizvodnje spojeva formule (I) prema zahtjevu 1, naznačen time da obuhvaća: (i) dobivanje karbonilnih spojeva formule (IV) pomoću obrade NH-aril-azola opće formule (V) sa spojem opće formule (VI) [image] pri čemu su R3, R4, R5, P, Q, V, W, X, Y i a, definirani kao gore za spojeve formule (I) i T je izlazna skupina; (ii) dobivanje derivata α-aminonitrila formule (II) pomoću obrade karbonilnih spojeva opće formule (IV) s izvorom cijanida s aminom opće formule R6-NH2 u prisutnosti amonijeve soli: [image] pri čemu su R3, R4, R5, R6, P, Q, V, W, X, Y i a, definirani kao gore za spojeve formule (I); i (iii) reakcija spoja (II) sa spojem (III) u prisutnosti lužine u otopini: [image] pri čemu su R3, R4, R5, R6, R7, P, Q, V, W, X, Y, Z i a, definirani kao gore za spojeve formule (I) iT je izlazna skupina.
11. Spoj prema zahtjevu 1, naznačen time, da se upotrebljava u liječenju endoparazitne infekcije kod sisavca kojemu je to potrebno.
12. Spoj prema zahtjevu 11, naznačen time, da je za uporabu kada je endoparazitna infekcija ona s helmintom odabranim iz skupine koju čine: Anaplocephala (Anoplocephala), Ancilostoma, Anecator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cilicociklus, Cilicodontophorus, Cilicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipilidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonclius, Metastrongilus, Moniezia, Necator, Nematodirus, Nippostrongilus, Oesophagostumum, Onchocerca, Ostertagia, Oksiuris, Paracaris, Schistosoma, Strongilus, Taenia, Toksocara, Strongiloides, Toksascaris, Trichinella, Trichuris, Trichostrongilus, Triodontophorous, Uncinaria, Wuchereria, i njihove kombinacije.
13. Spoj prema zahtjevu 12, naznačen time, da je za uporabu gdje je helmint sljedeći: Haemonchus contortus, Ostertagia circumcincta, Trichostrongilus axei, Trichostrongilus colubriformis, Cooperia curticei, Nematodirus battus, i njihove kombinacije.
14. Spoj prema zahtjevu 13, naznačen time, da je za uporabu gdje helmint je Haemonchus contortus , a spoj je spoj formule (I) gdje: P je N; Q je C-R2 ili N; V je C-R8 ili N; W je C-R9; X je C-R10; Y je C-R11; R2 je vodik, Cl, Br, metil ili metoksi; R3, R4 i R6 su H; R5 je metil; R7 je fenil supstituiran s OCF3, SCF3 ili CHFCF3; R8 je H, Cl, Br, F ili CN; R9 je H, Cl ili Br; R10 je H, Cl, Br ili CF3; R11 je H, Cl, Br ili metil; Z je C(O); i a je 1.
15. Spoj prema zahtjevu 13, naznačen time, da je za uporabu gdje helmint je Haemonchus contortus, a spoj je spoj formule (I) pri čemu: P je N; Q je C-R2 ili N; V je N; W je C-R9; X je C-R10; Y je C-R11; R2 je vodik, Cl, Br ili metoksi; R3, R4 i R6 su H; R5 je metil; R7 je fenil supstituiran s OCF3 ili SCF3; R8 je H; R10 je Cl ili Br; R11 je H; Z je C(O); i a je 1.
16. Spoj prema zahtjevu 1, naznačen time, da se upotrebljava u liječenju ektoparazitne infekcije kod sisavca kojemu je to potrebno.
17. Spoj prema zahtjevu 16, naznačen time, da je za uporabu pri kojoj je ektoparazitna infekcija nastala od ektoparazita odabranog iz skupine koju čine: buhe, krpelji, crvi, komarci, muhe, uši, muhe zunzare, te njihove kombinacije.
18. Spoj prema zahtjevu 17, naznačen time, da je za uporabu pri kojoj je ektoparazitna infekcija nastala od buha.
19. Postupak proizvodnje spoja ariloazol-2-il-cijanoetilamina prema zahtjevu 1, naznačen time, da obuhvaća sljedeće korake: (a)(i) reakcija spoja formule (V): [image] sa spojem formule (VI) pri čemu T je izlazna skupina: [image] za tvorbu spoja formule (IV): [image] ili (a)(ii) reakcija spoja formule (XVI): [image] s NaNO2/kiselinom; t-butilnitrilom ili izoamilnitrilom i bakrenim halidom za tvorbu spoja formule (XIV); pri čemu R16 je atom halogena [image] [image] gdje reagira spoj formule (XIV) sa spojem formule (XV); pri čemu M je trialkiltin, borna kiselina ili borni ester; R14 i R15 su neovisno odabrani od C1-C4-alkilkarbonila i C1-C4-alkila [image] za tvorbu spoja formule (XIII) [image] [image] podvrgavanjem spoja formule (XIII) oksidacijskom cijepanju za tvorbu spoja formule (X): [image] pri čemu reagira spoj formule (X) sa spojem formule (XI): [image] gdje R12 je hidroksi-zaštitna skupina: za tvorbu spoja formule (IXa): [image] podvrgavanjem spoja formule (IXa) koraku heterociklizacije za tvorbu spoja formule (VIIIb): [image] podvrgavanjem spoja formule (VIII) deprotekciji hidroksil-zaštitne skupine, za tvorbu spoja formule (VII): [image] (VII) gdje Q je CH; i oksidiranjem spoja formule (VII) za tvorbu spoja formule (IV); gdje reagira spoj formule (IV) [image] s R6-NH2 za tvorbu spoja formule (II): [image] [image] i (c) reakcija spoja formule (II) s T-Z-R7 u prisutnosti lužine, za tvorbu spoja prema zahtjevu 1, pri čemu su P, Q, V, W, X, Y, R3, R4, R5, R6, R7, Z i a, kao što su definirani u zahtjevu 1.
20. Spoj ariloazol-2-il-cijanoetilamina prema zahtjevima 1, 2 i 7, naznačen time, da je odabran od sljedećih: N-[2-(6-kloro-3-metoksi-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.001), N-[2-(6-kloro-3-metoksi-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometiltiobenzamid (spoj br. 3.002), N-[2-(6-bromo-7-metil-2H-[1,2,3]triazolo[4,5-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.003), N-[2-(6-bromo-7-metil-2H-[1,2,3]triazolo[4,5-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometiltiobenzamid (spoj br. 3.004), N-[2-(6-kloro-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.005), N-[2-(6-kloro-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometiltiobenzamid (spoj br. 3.006), N-[2-(6-bromo-3-metoksi-7-metil-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.007), N-[2-(6-kloro-3-metoksi-7-metil-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.008), N-[2-(6-bromo-7-metil-2H-pirazolo[4,3-b]-piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.009), N-[2-(6-kloro-7-metil-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.010), N-[2-(6-bromo-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.011), N-[2-(6-bromo-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometiltiobenzamid (spoj br. 3.012), N-[2-(6-bromo-7-metil-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometiltiobenzamid (spoj br. 3.023), N-[1-cijano-2-(3,6-dikloro-2H-pirazolo[4,3-b]piridin-2-il)-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.017), N-[2-(3-bromo-6-kloro-2H-pirazolo[4,3-b]piridin-2-il)-1-cijano-1-metiletil]-4-trifluorometoksibenzamid (spoj br. 3.019).
HRP20151058TT 2007-05-15 2015-10-05 Ariloazol-2-il-cijanoetilamino-spojevi, postupak njihove proizvodnje i postupak njihove uporabe HRP20151058T2 (hr)

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PCT/US2008/063417 WO2008144275A1 (en) 2007-05-15 2008-05-12 Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof
EP08769452.7A EP2155699B9 (en) 2007-05-15 2008-05-12 Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof

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