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US 8,618,126 B2Granted
Antiparisitic dihydroazole compounds and compositions comprising same
AssigneeMerial Limited
InventorsLoic Patrick Le Hir de Fallois, Hyoung Ik Lee, Douglas Edward Wilkinson, Brent Christopher Beck
Life of this patent
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Abstract
The present invention relates to novel dihydroazole of formula (I) and salts thereof: Wherein R1, A1, A2, G, X and Y are as defined in the description, compositions thereof, processes for their preparation and their uses to prevent or treat parasitic infections or infestations in animals and as pesticides.
Claims30
A dihydroazole compound of formula (I), or a pharmaceutically or agriculturally acceptable salt thereof:
- wherein:
- R1 is halogen, —CN, or alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(O)—, R7S(O)2—, R7C(O)—, R7R8NC(O)—, R7OC(O)—, R7C(O)O—, R7C(O)NR8—, —CN or —NO2;
- X is aryl or heteroaryl, which may be unsubstituted or substituted by one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(O)—, R7S(O)2—, R7C(O)—, R7R8NC(O)—, R7OC(O)—, R7C(O)O—, R7C(O)NR8—, —CN or —NO2;
- A1 is oxygen;
- A2 is oxygen, NR2 or CR7R8;
- G is G-2;
- B1, B2, B3, B4 and B5 are independently C—R9;
- Y is hydrogen, halogen, —CN;
- or Y is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, or heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(O)—, R7S(O)2—, R7C(O)—, R7R8NC(O)—, R7OC(O)—, R7C(O)O—, R7C(O)NR8—, —CN or —NO2;
- or Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-11, Y-12 or Y-13;
- R2, R3 are independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, R10S(O)—, R10S(O)2—, R10C(O)—, R10C(S)—, R10R11NC(O)—, R10R11NC(S)— R10OC(O)—;
- R4, R5 and R6 are independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl or heteroaryl;
- R7 and R8 are independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
- R9 is hydrogen, halogen, —CN, or alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R7S(O)—, R7S(O)2—, R7C(O)—, R7R8NC(O)—, R7OC(O)—, R7C(O)O—, R7C(O)NR8—, —CN or —NO2;
- R10, R11, R12 and R13 are each independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
- or
- R10 together with R11 form ═O, ═S or ═NR2;
- or
- R12 together with R13 form ═O, ═S or ═NR2;
- W is O, S or NR2;
- n is 1-4;
- and
- m is 0, 1 or 2.
20 more elements
A dihydroazole compound of formula (IIa), or pharmaceutically or agriculturally acceptable salt thereof:
- wherein Z, B1, B2, B3, B4, B5, R15, R16 and p are selected from:
- Compound
- No.
- (Z)p
- B5
- B4
- B3
- B2
- B1
- R15
- R16
- 1.001
- 3,5-Cl2
- C—H
- C—H
- C—H
- C—H
- N
- H
- CH2C(O)NHCH2CF3
- 1.002
- 3,5-Cl2
- C—H
- C—H
- C—H
- C—H
- N
- H
- CH2CF3
- 1.003
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- N
- CH3
- CH2CO2CH3
- 1.004
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- N
- CH3
- CH2CO2H
- 1.005
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- N
- CH3
- CH2C(O)NHCH2CF3
- 1.006
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- N
- H
- CH2C(O)NHCH2CF3
- 1.007
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- N
- H
- CH2CH2SCH3
- 1.008
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2C(O)NHCH2CF3
- 1.009
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2CH2SCH3
- 1.010
- 3,5-(CF3)2
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2CF3
- 1.011
- 3,5-Cl2
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2C(O)NHCH2CF3
- 1.012
- 3,5-Cl2
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2CF3
- 1.013
- 3,5-Cl2
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2CH2SCH3
- 1.014
- 3-Cl,5-CF3
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2C(O)NHCH2CF3
- 1.015
- 3-Cl,5-CF3
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2CF3
- 1.016
- 3-Cl,5-CF3
- C—H
- C—H
- C—H
- C—H
- C—H
- H
- CH2CH2SCH3
- 1.017
- 3,5-Cl2
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2C(O)NHCH2CF3
- 1.018
- 3,5-Cl2
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2CF3
- 1.019
- 3,5-Cl2
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2CH2SCH3
- 1.020
- 3,5-(CF3)2
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2C(O)NHCH2CF3
- 1.021
- 3,5-(CF3)2
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2CF3
- 1.022
- 3,5-(CF3)2
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2CH2SCH3
- 1.023
- 3-Cl,5-CF3
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2C(O)NHCH2CF3
- 1.024
- 3-Cl,5-CF3
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2CF3
- 1.025
- 3-Cl,5-CF3
- C—H
- C—H
- C—Me
- C—H
- C—Me
- H
- CH2CH2SCH3.
233 more elements
Dependencies are inferred from the claim text.