ME00044B - Substituisani imidazoli i njihova upotreba kao pesticida - Google Patents
Substituisani imidazoli i njihova upotreba kao pesticidaInfo
- Publication number
- ME00044B ME00044B MEP-2008-42A MEP200842A ME00044B ME 00044 B ME00044 B ME 00044B ME P200842 A MEP200842 A ME P200842A ME 00044 B ME00044 B ME 00044B
- Authority
- ME
- Montenegro
- Prior art keywords
- ethyl
- dimethylphenyl
- group
- imidazole
- alkyl
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title abstract 2
- 239000000575 pesticide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 238000000034 method Methods 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 2
- 230000000590 parasiticidal effect Effects 0.000 claims abstract 2
- -1 form 1 Chemical group 0.000 claims 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 241001465754 Metazoa Species 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 241000238631 Hexapoda Species 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 2
- 206010061217 Infestation Diseases 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 244000045947 parasite Species 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- FAHUKNBUIVOJJR-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine Chemical compound C1=CC(F)=CC=C1C1C2=CC=CN2CCN1 FAHUKNBUIVOJJR-UHFFFAOYSA-N 0.000 claims 1
- RYMBPJBTYXXTKV-UHFFFAOYSA-N 1-benzyl-2-[1-(2,3-dimethylphenyl)ethyl]imidazole Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=NC=CN1CC1=CC=CC=C1 RYMBPJBTYXXTKV-UHFFFAOYSA-N 0.000 claims 1
- FXJRDUKXWHFPND-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=NC=CN1 FXJRDUKXWHFPND-UHFFFAOYSA-N 0.000 claims 1
- IWOOTJMGZNQLKN-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C=1C(C)=CC=C(C)C=1C(C)C1=NC=CN1 IWOOTJMGZNQLKN-UHFFFAOYSA-N 0.000 claims 1
- BFPWWMHMPOMZIB-UHFFFAOYSA-N 2-[1-(3,5-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C=1C(C)=CC(C)=CC=1C(C)C1=NC=CN1 BFPWWMHMPOMZIB-UHFFFAOYSA-N 0.000 claims 1
- DVRSNIFQMIUPPI-UHFFFAOYSA-N 2-[1-(3-methylphenyl)ethyl]-1h-imidazole Chemical compound C=1C=CC(C)=CC=1C(C)C1=NC=CN1 DVRSNIFQMIUPPI-UHFFFAOYSA-N 0.000 claims 1
- PQLXCNZMCQTKHR-UHFFFAOYSA-N 2-[1-(4-chloro-3-methylphenyl)ethyl]-1h-imidazole Chemical compound C=1C=C(Cl)C(C)=CC=1C(C)C1=NC=CN1 PQLXCNZMCQTKHR-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 241000251468 Actinopterygii Species 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- CGVJRYSZXMFVST-UHFFFAOYSA-N [2-[1-(2,3-dimethylphenyl)ethyl]imidazol-1-yl]methyl propanoate Chemical compound CCC(=O)OCN1C=CN=C1C(C)C1=CC=CC(C)=C1C CGVJRYSZXMFVST-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- FGPDDJMBTHHHRK-UHFFFAOYSA-N methyl 3-cyclopentylpropanoate Chemical compound COC(=O)CCC1CCCC1 FGPDDJMBTHHHRK-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000003071 parasitic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- DUWIPJYYAOGKMW-UHFFFAOYSA-N propan-2-yl 2-[1-(2,3-dimethylphenyl)ethyl]imidazole-1-carboxylate Chemical compound CC(C)OC(=O)N1C=CN=C1C(C)C1=CC=CC(C)=C1C DUWIPJYYAOGKMW-UHFFFAOYSA-N 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002297 parasiticide Substances 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Ovaj pronalazak se odnosi na brojna jedinjenja alfa supstituisanih 2-benzil supstituisanog imidazola i njihove farmaceutski prihvatljive soli i solvate, na kompozicije koje sadrže ova jedinjenja, procese za njihovu sintezu i njihovu upotrebu kao paraziticida.
Claims (15)
1.Jedinjenje formule (I): pri čemu: R1, R2, R3, R4 i R5 su nezavisno izabrani iz grupe koja sadrži vodonik, cijano, nitro, halo,hidroksi, C1-4 alkil grupu opciono supstituisanu sa jednom ili više hidroksi grupa, C3-6 cikloalkil grupu opciono supstituisanu sa jednom ili više halo grupa, C3-6 alkil ili halo grupu. C1-4 alkoksi, C1-4 haloalkil. Cm haloalkoksi, fenil, amino, NRxRy i S(O)nR10 grupu; R je izabran iz grupe koja sadrži vodonik, -C0-2alkilenR, -C1-2alkilenOR, -C0-2alkilenC(O)R,-C1-2alkilenOC(O)R7, -C1-2alkilen OC(O)OR7, -C0-2alkilenC(O)OR7, -C1-2alkilenN(H)C(O)R7,-C1-2alkilenN(R7)C(O)R7, -C0-2alkilenC(O)NHR7, -C0-2alkilenC(O)NRl5R16, -C1-2alkilenNHC(O)NRl5R16, -C1-2alkilenNR7C(O)NR15R16, -C1-2alkilen0C(O)NHR7, -C1-2alkilenOC(O)NRl5R16, -C0-2alkilenCH=N(R7), -C1-2alkilenP(=O)(NRl5Rl6)(NR15R16), -C0-2alkilenSi(R7)3 i -C0-2alkilenS(O)nR10 grupe; gde C0-2alkilen ili -C1-2alkilen grupa R6 radikala mogu, kada je hemijski moguće, opciono dabudu supstituisane sa jednim ili više supstituenata izabranih iz grupe koja sadrži C1-6 alkil, C3-6 cikloalkil, C1-4alkilen(C3-6cikloalkil), C0-6alkilenfenil grupe, čiji C0-2alkilen ili -C1-2 alkilen supstituent mogu po redu da budu opciono dalje supstituisani, kada je hemijski moguće, sa jednim ili više supstituenata izabranih iz grupe koja sadrži vodonik. cijano, nitro, halo, formi 1, okso, hidroksi, C(O)0H, C1-4alkil, C1-4alkilenC3-6cikloalkil, C1-4alkoksi, C1-4alkilenC1-4alkiloksi, -C(O)OCm alkil. C1-4haloalkil, C1-4 haloalkoksi, amino, C1-4 alkilamino, C1-4 dialkilamino i S(O)nR10 grupu; gde je svaki R7, R15 i R16, kada je hemijski moguće, nezavisno izabran iz grupe koja sadrživodonik, C1-8 alkil, C2-6 alkenil, C2-6 alkinil, C3-8 cikloalkil. C1-4 alkilen(C3-6 cikloalkil), C1-4alkilenC1-4 alkoksi, C1-6 haloalkil, C0-6 alkilenfenil, C0-6 alkilennaftil, C0-6 alkilen(tetrahidronaftil) i C0-2 alkilen(Het) grupu, gde je het grupa izabrana od oksetanil, tetrahidropiranil, piperidinil. morfolinil, furil, piridil. benzofuranil, benzotiazolil, indolil, 2, 3-benzodioksolil. 2, 3-hidroksi-l, 4-benzodioksinil, indolil i 1, 5-naftiridinil grupe; ili R15 i R16 zajedno sa azotom za koji su vezani mogu da formiraju zasićeni ili nezasićeni heterociklični prsten od tri do sedam članova koji opciono sadrži jedan ili više novih N. O ili S atoma ili SO2 grupa; gde svaka od prethodnih R7, R15 ili R16 grupa može nezavisno da obuhvati jedan ili više opcionih supstituenata, kada je hemijski moguće, izabranih od vodonika, cijano, nitro, halo, formil, okso, hidroksi, C(O)OH, C1-4 alkil, C2-4 alkenil, C2-4 alkinil, C3-6 cikloalkil, C1-4 alkilenC3-6cikloalkil. C1-4 alkoksi, C1-4 alkilenC1-4 alkiloksi, C1-4 alkoksiC1-4 alkoksi, C1-4 alkanoil, -C(O)OCm alkil. Cm haloalkil, C3-6halocikloalkil, C1-4 haloalkoksi, C1-4 haloalkanoil, -C(O)OC1-4 haloalkil. fenil, 4-halofenil, 4-alkoksifenil, 2-cijanofenil, fenoksi, 4-halofenoksi, benziloksi, 4-halobenziloksi, benzoil, pirazolil, triazolil, 2-halo-4-pirimidinil, 2-feniletil, amino, C1-4 alkilamino, C1-4 dialkilamino, C(O)N(C1-4 alkil)2, N(C1-4 alkilen)C(O)(C1-4 alkil) i S(O)nR10 grupe; R8 i R9 su nezavisno izabrani iz grupe koja sadrži vodonik, C1-4 alkil, C1-4 alkoksi, C1-4 haloalkil, C1-4 haloalkoksi i C0-4alkilenfenil grupu ali uz uslov da R8 i R9 grupe nisu obe vodonik; gde svaka R8 i R9 grupa može nezavisno da obuhvati jedan ili više opcionih supstituenata, kada je hemijski moguće, izabranih od vodonika, cijano, halo, hidroksi, C1-4 alkil, C3-6cikloalkil, C1-4 alkoksi, -C(O)OCm alkil, C1-4 haloalkil, C1-4 haloalkoksi i S(O)nR10 grupe; ili R8 i R9 zajedno sa ugljenikom za koji su vezani mogu da formiraju od tri do šest člani karbociklični, zasićeni prsten, koji je opciono supstituisan sa jednim ili više supstituenata izabranih iz grupe koja sadrži halo, C1-2 alkil, C1-2 alkoksi, C1-2haloalkil, C1-2haloalkoksi grupu; R11 i R12 su nezavisno izabrani iz grupe koja sadrži vodonik, halo, cijano, C1-4 alkil, C1-4 alkoksi, C1-4 haloalkil i C1-4 haloalkoksi grupu; gde su Rx i Ry nezavisno izabrani od vodonika, C1-4 alkil, C1-4 haloalkil i S(O)nR10 grupe; svaki n je nezavisno 0, 1 ili 2; i svaki R10 je nezavisno vodonik, hidroksi, C1-4 alkil, C1-4 haloalkil, 4-halofenil, amino, C1-6alkil amino i di C1-6alkil amino grupa; ili njihova farmaceutski prihvatljiva so ili prolek.
2.Jedinjenje u skladu sa patentnim zahtevom 1, naznačeno time što su R1 i R2 metil grupa, a R3, R4 i R5 su vodonik.
3.Jedinjenje u skladu sa patentnim zahtevom 1 ili 2, naznačeno time sto je R6 izabran iz grupe koja sadrži vodonik, -C1-2alkilenR7 * i - C1-2alkilenOC(O)R7 grupu.
4.Jedinjenje u skladu sa patentnim zahtevom 3, naznačeno time što je R6 izabran iz grupe koja sadrži vodonik. 2, 2-dimetilpropioniloksimetil, propioniloksimetil, 3- ciklopentilpropioniloksimetil. 3-metilbutiriloksimetil, heptanoiloksimetil. butiriloksimetil, pentanoiloksimetil, fenilmetil, 4-metoksibenziloksikarboniloksimetil. ciklopropilmetil, metil, ciklopropilmetiloksikarboniloksimetil, 3-metilbutoksikarboniloksimetil, izopropoksikarboniloksimetil, ciklobutoksikarboniloksimetil, 2, 2, 2- trifluoroetioksikarboniloksimetil, etil. 4-metoksibenzil. metoksimetil. 4- (trifluorometil)benzil. izobutoksikarbonil, izopropoksikarbonil grupu.
5.Jedinjenje u skladu sa bilo kojim zahtevom od 1 do 4, naznačeno time stoje R8 je metil grupa, a R9 je vodonik.
6.Jedinjenje u skladu sa bilo kojim zahtevom od 1 do 5, naznačeno time što su R11 i R12 oba vodonik.
7. Jedinjenje u skladu sa patentnim zahtevom 1, naznačeno time što je izabrano od: 2-[l-(2, 3-dimetilfenil)etil]-lH-imidazola; 2-[( 1S)-1 -(2, 3-dimetilfenil)etilj-1 H-imidazola; 2-[( 1 fl)-1 -(2, 3-dimetilfenil)eti 1]-1 H-imidazola; {2-[ 1 -(2, 3-dimetilfenil)etilj-1 H-imidazol-1 -il}metil pivalata; [2-[(l S)-1 -(2, 3-dimetilfenil)etilj-1 H-imidazol-1 -ii}metilpivalata; [2-[(l R)-l-(2, 3-dimetilfenil)etil]-lH-imidazol-1 -il}metilpivalata; {2-[l-(2, 3-dimetilfenil)etil]-lH-imidazol-1 -il}metil propionata; {2-[ 1 -(2, 3-dimetilfenil)etilj-1 H-imidazol-1 -il}metil 3-metilbutanoata; {2-[ 1-(2, 3-dimetilfeniljetil]-1 H-imidazol-1 -il}metil butirata; {2-[l-(2, 3-dimetilfeniljetil]-1 H-imidazol-1 -il)metil 3-ciklopentilpropanoata; {2-[l-(2, 3-dimetilfenil)etill-l H-imidazol-1 -il)metil heptanoata; {2-[l-(2, 3-dimetilfenil)etil]-l H-imidazol-1 -il}metil pentanoata 2- {1 -[2-(trif luorometil)fenil]etil} -1 H-imidazola; 2-[l-(2, 5-dimetilfenil)etil]-lH-imidazola; 2-[ 1 -(4-hlor-3-metilfenil)etil]-1 H-imidazola; 2-[l-(3, 5-dimetilfenil)etil]-lH-imidazola; 1 -benzil-2-[ 1 -(2, 3-dimetilfenil)etil]-1 H-imidazola; (2-[l-(2, 3-dimetilfenil)etil]-lH-imidazol-l-il}metil 4-metoksibenzil karbonata; 1 -(ciklopropilmetil)-2-[i-(2, 3-dimetilfenil)etil]-1 H-imidazola; 2-[l -(2, 3-dimetilfenil)etil]-l -metil-1 H-imidazola; ciklopropilmetil {2-[l-(2, 3-dimetilfenil)etil]-lH-imidazol-l-il}metil karbonata; {2-[ 1 -(2, 3-dimetiltenil)etil]-1 H-imidazol-1 -il}meti 1 3-metilbutil karbonata; {2-[l-(2, 3-dimetilfenil)etil]-l H-imidazol-l-il}metil izopropil karbonata; ciklobutil {2-[ 1 -(2, 3-dimetilfenil)etil]-1 H-imidazol-1 -il}metil karbonata; {2-[ 1 -(2, 3-dimetiltenil)etil]-1 H-imidazol-1 -il}metil 2, 2, 2-trifluoroetil karbonata; 2-[l-(2, 3-dimetilfenil)etil]-l-etil-1 H-imidazola; 2-[l-(2, 3-dimetilfenil)etil]-l-(4-metoksibenzil)-1 H-imidazola; 2-[l-(2, 3-dimetilfenil)etil]-l-(metoksimetil)-i H-imidazola; 2-[l-(2, 3-dimetilfenil)etil]-l-[4-(trifluorometil)benzil]-l H-imidazol 4-fluorofenil 2-[l-(2, 3-dimetilfenil)etil]-1 H-imidazol-1-karboksilata; izobutil 2-[ 1 -(2, 3-dimetilfenil)etil]-1 H-imidazol-1 -karboksilata; izopropil 2-[l-(2, 3-dimetilfenil)etil]-lH-imidazol-1-karboksilata; 2-[ 1 -(3-metilfenil)etil]-1 H-imidazola; ili njihove farmaceutski prihvatljive soli ili proleka.
8.Farmaceutska, veterinarska ili agrokulturna kompozicija koja uključuje jedinjenje formule (I), kako je definisano u bilo kom patentnom zahtevu od 1 do 7, ili njegovu farmaceutski prihvatljivu so i pogodan ekscipijent ili nosač.
9.Upotreba jedinjenja formule (I), kako je defmisano u bilo kom patentnom zahtevu od 1 do 7, ili njegove farmaceutski, veterinarski ili agrokulturno prihvatljive soli, u proizvodnji paraziticidalnih medikamenata za ljude ili životinje.
10.Kombinacija jedinjenja formule (I), kako je defmisano u bilo kom patentnom zahtevu od 1 do 7, i drugog farmakološki aktivnog sredstva.
11.Metod za tretiranje najezde parazita na životinji domaćinu koji uključuje tretiranje životinje domaćina sa efektivnom količinom jedinjenja formule (I), kako je definisano u bilo kom patentnom zahtevu od 1 do 7.
12.Metod u skladu sa patentnim zahtevom 11, naznačen time što je sisar ptica ili riba, a parazit je neki insekt ili akarid.
13.Metod u skladu sa patentnim zahtevom 11, naznačen time što je životinja domaćin neki insekt, a parazit je neki akarid.
14.Metod za kantrolu najezde insekata ili akarida na mesto, naznačen time što uključuje nanošenje efektivne količine jedinjenja formule (I), kako je defmisano u bilo kom patentnom zahtevu od 1 do 7, na određeno mesto.
15.Metod u skladu sa patentnom zahtevom 14, naznačen time što mesto nije životinja domaćin.
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2007
- 2007-01-04 US US11/619,735 patent/US7592362B2/en active Active
- 2007-01-08 WO PCT/IB2007/000071 patent/WO2007083207A1/en not_active Ceased
- 2007-01-08 PL PL07700025T patent/PL1981853T3/pl unknown
- 2007-01-08 CA CA2632771A patent/CA2632771C/en not_active Expired - Fee Related
- 2007-01-08 EP EP07700025A patent/EP1981853B1/en active Active
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