DK2513104T3 - Antiparasit-dihydroazolforbindelser og sammensætninger omfattende disse - Google Patents

Antiparasit-dihydroazolforbindelser og sammensætninger omfattende disse Download PDF

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DK2513104T3
DK2513104T3 DK10796566.7T DK10796566T DK2513104T3 DK 2513104 T3 DK2513104 T3 DK 2513104T3 DK 10796566 T DK10796566 T DK 10796566T DK 2513104 T3 DK2513104 T3 DK 2513104T3
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alkyl
compound
haloalkyl
hydrogen
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Hir De Falois Loic Patrick Le
Hyoung Lk Lee
Douglas Edward Wilkinson
Brent Christopher Beck
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Merial Inc
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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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    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05—Dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
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    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Claims (28)

1. Dihydroazolforbindelse med formel (I), eller et farmaceutisk eller landbrugsmæssigt acceptable salt deraf:
© hvor: Ri er hydrogen, halogen, -CN, eller alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl eller cycloalkylalkyl, der hver er usubstitueret eller substitueret med én eller flere af halogen, hydroxy, amino, alkyl- eller di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(0)-, R7S(0)2-, R7C(0)-, R7R8NC(0)-, R70C(0)-, R7C(0)0-, R7C(0)NR8-, -CN eller NO2; X er aryl eller heteroaryl, der hver kan være usubstitueret eller substitueret med én eller flere af halogen, hydroxy, amino, alkyl- eller di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(0)-, R7S(0)2-, R7C(0)-, R7R8NC(0)-, R70C(0)-, R7C(0)0-, R7C(0)NRs-, -CN eller NO2; Ai og A2 er uafhængigt oxygen, NR2 eller CR7Re; G er G-l eller G-2;
G-l G-2 Bi, B2, B3, B4 og B5 er uafhængigt N eller C-Rg; Y er hydrogen, halogen, -CN; eller Y er alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, eller heterocyclyl eller heteroaryl der hver er usubstitueret eller substitueret med én eller flere af halogen, hydroxy, amino, alkyl,- eller di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(0)-, R7S(0)2-, R7C(0)-, R7R8NC(0)-, R70C(0)-, R7C(0)0-, R7C(0)NR8-, -CN eller -NO2; eller Y er Y-l, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-ll, Y-12 eller Y-13;
R2, R3 er uafhængigt hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkenyl, haloalkynyl, cycloalkyl, RioS(O)-, RioS(0)2-, RioC(O)-, RioC(S)-, RioRnNC(O)-, RioRuNC(S)-,RioOC(0)-; R4, R5 og Re er uafhængigt hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl eller heteroaryl; R7 og Rs er uafhængigt hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl eller haloalkynyl; Rg er hydrogen, halogen, -CN, eller alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl eller cycloalkylalkyl, der hver er usubstitueret eller substitueret med én eller flere af halogen, hydroxy, amino, alkyl- eller di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(0)-, R7S(0)2-, R7C(0)-, R7R8NC(0)-, R70C(0)-, R7C(0)0-, R7C(0)NR8-, -CN eller -NO2; Rio, R11, R12 og R13 er hver uafhængigt hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl eller haloalkynyl; eller Rio sammen med R11 danner =0, =S eller =NR2; eller R12 sammen med R13 danner =0, =S eller =NR2; W er O, S eller NR2; n er 1-4; og m er 0,1 eller 2.
2. Forbindelsen ifølge krav 1, hvor G er G-l,
3. Forbindelsen ifølge krav 1, hvor G er G-2.
4. Forbindelsen ifølge krav 1, hvor: G er G-l; Ai er oxygen; og X er eventuelt substitueret aryl,
5. Forbindelsen ifølge krav 1, hvor: G er G-2; Ai er oxygen; og X er eventuelt substitueret aryl.
6. Forbindelsen ifølge krav 1, hvor: Ai er oxygen; X er eventuelt substitueret aryl; Ri er hydrogen, halogen, alkyl eller haloalkyl; og Y er Y-l, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-ll, Y-12 eller Y-13.
7. Forbindelse ifølge krav 1, hvor: Ai er oxygen; X er aryl; Ri er hydrogen, alkyl eller haloalkyl; Y er Y-l, Y-2 Y-3, Y-4, Y-5 eller Y-6; og R2, R3 er uafhængigt hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl.
8. Forbindelsen ifølge krav 1, hvor; Ai er oxygen; X er eventuelt substitueret aryl; Ri er hydrogen, halogen, alkyl eller haloalkyl; og Y er pyrazolyl eller triazolyl.
9. Forbindelsen ifølge krav 1, hvor: G er G-l; Bi, B2, B3, B4 og B5 hver er C-Rg; Ri er Ci-C4alkyl eller Ci-C4haloalkyl; X er phenyl, der hver kan være usubstitueret eller substitueret med én eller flere halogen, Ci-C4alkyl eller Ci-C4haloalkyl; Ai er oxygen; A2 er CR7R8; Y er Y-l, Y-4, Y-5, Y-6; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4lalkoxy-Ci-C4alkyl eller Ci-C4alkylthio-C4-C4alkyl; og Ra' og R9 er uafhængigt hydrogen, Ci-C4alkyl eller Ci-C4haloalkyl.
10. Forbindelsen ifølge krav 1, hvor: G er G-2; Bi B2, B3, B4 og B5 hver er C-Rg; Ri er Ci-C4alkyl eller Ci-C4haloalkyl; X er phenyl, der hver kan være usubstitueret eller substitueret med én eller flere halogen, Ci-C4alkyl eller Ci-C4haloalkyl; Ai er oxygen; A2 er CR7R8; Y er Y-l, Y-4, Y-5, Y-6; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloall(yl, C1-C4 alkoxy-Ci-C4alkyl eller Ci-C4alkylthio-Ci-C4alkyl; og R3, og Rg er uafhængigt hydrogen, Ci-C4alkyl eller Ci-C4haloalkyl.
11. Forbindelsen ifølge krav 1, hvor: G er G-l; Bi, B2, B4 og B5 hver er C-Rg; B3 er N; Ri er Ci-C4alkyl eller Ci-C4haloalkyl; X er phenyl, der hver kan være usubstitueret eller substitueret med én eller flere halogen, Ci-C4alkyl eller Ci-C4haloalkyl; Ai er oxygen; A2 er CR7R8; Y er Y-l, Y-4, Y-5, Y-6; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, C1-C4 alkoxy-Ci-C4alkyl eller Ci-C4alkylthio-Ci-C4alkyl; og R3, og Rg er uafhængigt hydrogen, Ci-C4alkyl eller Ci-C4haloalkyl,
12. Forbindelsen ifølge krav 1, hvor: G er G-2; B2, B3, B4 og B5 hver er C-Rg; Bi er N; Ri er Ci-C4alkyl eller Ci-C4haloalkyl; X er phenyl, der hver kan være usubstitueret eller substitueret med én eller flere halogen, Ci-C4alkyl eller Ci-C4haloalkyl; Ai er oxygen; ki er CR7R.8; Y er Y-l, Y-4, Y-5, Y-6; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, C1-C4 alkoxy-Ci-C4alkyl eller Ci-C4alkylthio-Ci-C4alkyl; og R3, og R9 er uafhængigt hydrogen, Ci-C4alkyl eller Ci-C4haloalkyl.
13. Forbindelsen ifølge krav 9 eller krav 10, hvor: ki er CH2; R9 er hydrogen; R12 sammen med R13 danner =0, =S eller =NR2; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloalkyl; og R3, R7 og Re hver er hydrogen,
14. Forbindelse ifølge krav 1 hvor Rio sammen med R11 danner =0.
15. Forbindelse ifølge krav 1 hvor R12 sammen med R13 danner =0,
16. Forbindelsen ifølge krav 9 eller krav 10, hvor; ki er CH2; Rg er hydrogen; Rio sammen med Ru danner =0, =S eller NR2; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloalkyl; og R3, R7 og Rs hver er hydrogen.
17. Forbindelsen ifølge krav 9, hvor: A2 er CH2; Ro er hydrogen; Rio sammen med Ru danner =0, =S eller =NR2; R12 sammen med R13 danner =0, =S eller =NR2; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl eller Ci-C4haloalkyl; og R3, R7 og Rs er hydrogen.
18. Forbindelsen ifølge krav 11 eller krav 12, hvor: A2 er CH2; Rg er hydrogen; R12 sammen med R13 danner =0, =S eller =NR2; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloalkyl; og R3, R7 og Rs hver er hydrogen.
19. Forbindelsen ifølge krav 11 eller krav 12, hvor: ki er CH2; Rg er hydrogen; Rio sammen med Ru danner =0, =S eller =NR2j R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl, Ci-C4haloalkyl; og R3, R7 og Rs hver er hydrogen.
20. Forbindelsen ifølge krav 11 eller krav 12, hvor: A2 er CH2; Rs er hydrogen; Rio sammen med Ru danner =0, =S eller =NR2; R12 sammen med R13 danner =0, =S eller =NR2; R2 og R4 er uafhængigt hydrogen, Ci-C4alkyl eller Ci-C4haloalkyl; og R3, R7 og Rs er hydrogen.
21. Forbindelse ifølge krav 1 valgt fra følgende:
22. Forbindelse ifølge krav 1 valgt fra følgende:
23. Sammensætning til anvendelse i behandlingen eller forebyggelse af en parasitinfektion eller -infestation i et dyr omfattende en effektiv mængde af en forbindelse med formel (I) ifølge krav 1 i kombination med en farmaceutisk acceptabel bærer.
24. Sammensætning til beskyttelsen af afgrøder, planter, planteformeringsmateriale eller materiale fremstillet af træ fra skadedyr omfattende en pesticid effektiv mængde af en forbindelse med formel (I) ifølge krav 1 i kombination med en landbrugsmæssigt acceptabel bærer eller fortyndingsmiddel.
25. Fremgangsmåde til beskyttelse af afgrøder og planter i vækst fra angreb eller infestation af skadedyr, omfattende at bringe en plante, ellerjord eller vand hvor planten vokser, i kontakt med en forbindelse med formel (I) ifølge krav 1.
26. Fremgangsmåde til forebyggelse eller styring af infestation af skadedyr ved et lokus, omfattende administration af en pesticidt effektiv mængde eller en parasitær effektiv mængde af en forbindelse med formel (I) ifølge krav 1 til lokuset; hvor lokuset udelukker det humane eller dyriske legeme.
27. Forbindelsen ifølge krav 1 til anvendelse i behandlingen eller forebyggelse af en parasitinfektion eller -infestation hos et dyr.
28. Anvendelse af forbindelsen ifølge krav 1 i fremstillingen af et medikament til behandlingen eller forebyggelse af en parasitinfektion eller -infestation i et dyr.
DK10796566.7T 2009-12-17 2010-12-16 Antiparasit-dihydroazolforbindelser og sammensætninger omfattende disse DK2513104T3 (da)

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