ARYLOAZOL-2-YL CYANOETHYLAMINO COMPOUNDS, METHOD OF MAKING AND METHOD OF USING THEREOF
First Claim
Patent Images
1. An aryloazol-2-yl-cyanoethylamine compound of the formula (I):
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P is C—
R1 or N;
Q is C—
R2 or N;
V is C—
R8 or N;
w is C—
R9 or N;
X is C—
R10 or N;
Y is C—
R11 or N;
R1, R2, R8, R9, R10 and R11 either, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, hydroxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, phenoxy, alkoxyalkoxy, cycloalkyloxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino, alkylcarbonylamino, alkylaminoalkoxy, dialkylaminoalkoxy, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, formyl, HO2C—
, alkyl-O2C—
, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl;
R3, R4 and R5 either, independently of one another, is hydrogen, halogen, alkyl, hydroxyalkyl, alkylthioalkyl, haloalkyl, alkyloxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl;
unsubstituted or substituted cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and alkyl;
unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, di(alkyl)amino;
or R4 and R5 together with the carbon to which they are attached form a cycloalkyl ring;
R6 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, di(alkyl)amino;
R7 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, phenyl, phenoxy, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl alkylamino, di(alkyl)amino;
unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino;
orunsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino;
Z is a direct bond, C(O), C(S) or S(O)p;
a is 1, 2 or 3;
p is 0, 1 or 2; and
salts thereof.
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Abstract
The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives of formula (I):
wherein R3, R4, R5, R6, R7, P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.
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Citations
19 Claims
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1. An aryloazol-2-yl-cyanoethylamine compound of the formula (I):
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P is C—
R1 or N;Q is C—
R2 or N;V is C—
R8 or N;w is C—
R9 or N;X is C—
R10 or N;Y is C—
R11 or N;R1, R2, R8, R9, R10 and R11 either, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, hydroxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, phenoxy, alkoxyalkoxy, cycloalkyloxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino, alkylcarbonylamino, alkylaminoalkoxy, dialkylaminoalkoxy, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, formyl, HO2C—
, alkyl-O2C—
, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl;R3, R4 and R5 either, independently of one another, is hydrogen, halogen, alkyl, hydroxyalkyl, alkylthioalkyl, haloalkyl, alkyloxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl;
unsubstituted or substituted cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and alkyl;
unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, di(alkyl)amino;
orR4 and R5 together with the carbon to which they are attached form a cycloalkyl ring; R6 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, di(alkyl)amino; R7 is hydrogen, alkyl, alkoxyalkyl, alkylcarbonyl, alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, phenyl, phenoxy, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl alkylamino, di(alkyl)amino;
unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino;or unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, alkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylamino, di(alkyl)amino; Z is a direct bond, C(O), C(S) or S(O)p; a is 1, 2 or 3; p is 0, 1 or 2; and salts thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19)
Q is C—
R2 or N;V is C—
R8 or N;W is C—
R9 or N;X is C—
R10 or N;Y is C—
R11 or N;R1, R2, R8, R9, R10 and R11 either, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-akynyl, C3-C7-cycloalkyl, hydroxy-C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio arylthio, C1-C6-alkoxy, phenoxy, C1-C6-alkoxy-C1-C6-alkoxy, C3-C7-cycloalkyloxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylcarboxylamino, C1-C6-alkylamino-C1-C6-alkoxy, di-C1-C6-alkylamino-C1-C6-alkoxy, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, amino-C1-C6-alkyl, formyl, HO2C—
, C1-C6-alkyl-O2C—
, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halo-C1-C6-alkylsulfonyl;R3, R4 and R5 either, independently of one another, is hydrogen, halogen, C1-C6-alkyl, hydroxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylsulfonyloxy-C1-C6-alkyl;
unsubstituted or substituted C3-C7-cycloalkyl, wherein the substituents may each be independent of one another and are selected from the group consisting of halogen and C1-C6-alkyl;
unsubstituted or substituted phenyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halo-C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino;
orR4 and R5 together with the carbon to which they are attached form a cycloalkyl ring; R6 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkylthiocarbonyl or unsubstituted or substituted benzyl, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halo-C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino; R7 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkylthiocarbonyl or unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, phenyl, phenoxy, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halo-C1-C6-alkylsulfonyl C1-C6-alkylamino, di(C1-C6-alkyl)amino;
unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino;or unsubstituted or substituted naphthyl or quinolyl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino; Z is a direct bond, C(O), C(S) or S(O)p; a is 1, 2 or 3; p is 0, 1 or 2; and salts thereof.
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3. The aryloazol-2-yl-cyanoethylamine of claim 2, wherein
P and Q is N; -
V is C—
R8;W is C—
R9;X is C—
R10;Y is C—
R11;R8, R9, R10 and R11 either, independently of one another, is hydrogen, amino, amido, cyano, nitro, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-akynyl, C3-C7-cycloalkyl, hydroxy-C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio arylthio, C1-C6-alkoxy, phenoxy, C1-C6-alkoxy-C1-C6-alkoxy, C3-C7-cycloalkyloxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylcarboxylamino, C1-C6-alkylamino-C1-C6-alkoxy, di-C1-C6-alkylamino-C1-C6-alkoxy, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, amino-C1-C6-alkyl, formyl, HO2C—
, C1-C6-alkyl-O2C—
, unsubstituted or substituted aryl or unsubstituted or substituted phenoxy, whereby the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, halo-C1-C6-alkylsulfonyl;R3, R4 and R6 are H; R5 is methyl R7 is unsubstituted or substituted phenyl wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino;
unsubstituted or substituted hetaryl, wherein the substituents may each be independent of one another and are selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, arylthio, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino;Z is C(O); and a is 1; and salts thereof.
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4. The aryloazol-2-yl-cyanoethylamine of claim 1, wherein
P and Q is N; -
V is C—
R8;W is C—
R9;X is C—
R10;Y is C—
R11;R3, R4 and R6 are hydrogen; R5 is hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, hydroxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkyloxy-C1-C6-alkyl, or C1-C6-alkylsulfonyloxy-C1-C6-alkyl; R7 is unsubstituted phenyl or phenyl substituted by one or more substituents selected from the group consisting of C1-C6-alkyl, halo-C1-C6-alkyl, phenyl, phenyloxy, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylthio, halo-C1-C6-alkylthio, halo-C1-C6-alkylsulfinyl and halo-C1-C6-alkylsulfonyl; R8, R9, R10 and R11 either, independently of one another, is hydrogen, halogen, C1-C6-alkyl, halo-C1-C6-alkyl, cyano, C1-C6-alkoxy, halo-C1-C6-alkoxy, C2-C6-alkenyl, C1-C6-alkylamino, hydroxy-C1-C6-alkyl, formyl, C1-C6-alkylamino-C1-C6-alkyl, HO2C—
, C1-C6-alkyl-O2C—
or unsubstituted or substituted phenyl wherein the substituents are C1-C6-alkyl or halo-C1-C6-alkyl;Z is C(O); a is 1; and salts thereof.
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5. The aryloazol-2-yl-cyanoethylamine of claim 1, wherein
P and Q is N; -
V is C—
R8;W is C—
R9;X is C—
R10;Y is C—
R11;R3, R4 and R6 are hydrogen; R5 is methyl, ethyl, butyl, CH2OH, CH2OCH3, CH2SCH3, CH2OSO2CH3; R7 is a phenyl substituted with butyl, CF3, phenyl, phenoxy, OCF3, SCF3, SOCF3, SO2CF3; R8, R9, R10 and R11 either, independently of one another, is hydrogen, methyl, CH2NH2, CH2N(CH3)2, vinyl, CH2OH, CH(OH)CH2OH, CO2H, CO2CH3, Ph—
CF3, F, Cl, Br, CF3, OCF3 or CN;Z is C(O); a is 1; and salts thereof.
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6. The aryloazol-2-yl-cyanoethylamine of claim 1, wherein
P is N; -
Q is C—
R2;V is C—
R8;W is C—
R9;X is C—
R10;Y is C—
R11;R2 is hydrogen, Cl, methyl, methoxy, ethoxy, propoxy, butoxy, O(CH2)2OCH3, or O(CH2)2N(CH3)2; R3, R4 and R6 are hydrogen; R5 is methyl; R7 is phenyl substituted by OCF3, phenoxy, or SCF3; R8, R9, R10 and R11 either, independently of one another, is hydrogen, Cl, Br, C1-C6-alkyl, CF3, nitro, amino, amido, CO2CH3, or NHCOCH3; Z is C(O); a is 1; and salts thereof.
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7. The aryloazol-2-yl-cyanoethylamine of claim 1, wherein
P is N; -
Q is C—
R2 or N;V is N; W is C—
R9;X is C—
R10;Y is C—
R11;R2 is hydrogen, Cl, Br, methoxy; R3, R4 and R6 are hydrogen; R5 is methyl; R7 is phenyl substituted by OCF3 or SCF3; R9, R10 and R11 either, independently of one another, is hydrogen, Cl, Br or methyl; Z is C(O); and a is; and salts thereof.
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8. A pesticidal composition comprising a compound of claim 1 and a pesticidally acceptable carrier.
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9. The pesticidal composition of claim 8 which further comprises an additional pesticidal compound.
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10. A method of making the compounds of formula (I) of claim 1 which comprises of:
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(i) obtaining the carbonyl compounds of formula (IV) by treatment of a NH-aryl-azole of general formula (V) with compound of general formula (VI)
wherein, R3, R4, R5, P, Q, V, W, X, Y, and a are as defined above for the compounds of formula (I) and T is a leaving group;(ii) obtaining the α
-amino nitrile derivatives of formula (II) by treatment of carbonyl compounds of general formula (IV) with a cyanide source with amines of general formula R6—
NH2 in presence of ammonium salt;
wherein, R3, R4, R5, R6, P, Q, V, W, X, Y, and a are as defined above for the compounds of formula (I); and(iii) reacting compound (II) with compound (III) in the presence of a base in a solvent;
wherein R3, R4, R5, R6, R7, P, Q, V, W, X, Y, Z, and a are as defined above for the compounds of formula (I) and T is a leaving group.
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11. A method of treating endoparasiticidal infection in a mammal in need thereof which comprising administering an effective amount of the compound of claim 1.
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12. The method of claim 11, wherein the endoparasiticidal infection is a helminth selected from the group consisting of Anaplocephala (Anoplocephala), Ancylostoma, Anecator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cylicocyclus, Cylicodontophorus, Cylicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipylidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonchus, Metastrongylus, Moniezia, Necator, Nematodirus, Nippostrongylus, Oesophagostumum, Onchocerca, Ostertagia, Oxyuris, Paracaris, Schistosoma, Strongylus, Taenia, Toxocara, Strongyloides, Toxascaris, Trichinella, Trichuris, Trichostrongylus, Triodontophorous, Uncinaria, Wuchereria, and combinations thereof
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13. The method of claim 12, wherein the helminth is Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus and combinations thereof.
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14. The method of claim 13, wherein the helminth is Haemonchus contortus and the compound is a compound of formula (I) wherein:
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P is N; Q is C—
R2 or N;V is C—
R8 or N;W is C—
R9;X is C—
R10;Y is C—
R11;R2 is hydrogen, Cl, Br, methyl or methoxy; R3, R4 and R6 is H; R5 is methyl; R7 is phenyl substituted with OCF3, SCF3 or CHFCF3; R8 is H, Cl, Br, F or CN; R9 is H, Cl or Br; R10 is H, Cl, Br or CF3; R11 is H, Cl, Br or methyl; Z is C(O); and a is 1.
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15. The method of claim 13, wherein the helminth is Haemonchus contortus and the compound is a compound of formula (I) wherein:
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P is N; Q is C—
R2 or N;V is N; W is C—
R9;X is C—
R10;Y is C—
R11;R2 is hydrogen, Cl, Br or methoxy; R3, R4 and R6 is H; R5 is methyl; R7 is phenyl substituted with OCF3 or SCF3; R9 is H; R10 is Cl or Br; R11 is H; Z is C(O); and a is 1.
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16. A method of treating ectoparasiticidal infection in a mammal in need thereof which comprises administering an effective amount of the compound of claim 1.
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17. The method of claim 16, wherein the ectoparasiticidal infection is selected from the group consisting of fleas, ticks, mites, mosquitoes, flies, lice, blowfly and combinations thereof.
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18. The method of claim 17, wherein the ectoparasiticidal infection is fleas.
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19. A process of making the aryloazol-2-yl-cyanoethylamine compound of claim 1 which comprises:
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(a)(i) reacting a compound of formula (V); with a compound of formula (VI); to form the compound of formula (IV);
or(a)(ii) reacting a compound of formula (XVI); with NaNO2/acid;
t-butylnitrile or isoamylnitrile to form the compound of formula (XIV);reacting the compound of formula (XIV) with a compound of formula (XV); to form the compound of formula (XIII) subjecting the compound of formula (XIII) to oxidative cleavage to form the compound of formula (X); reacting the compound of formula (X) with a compound of formula (XI); wherein R12 is a hydroxy protection group; to form the compound of formula (IXa); subjecting the compound of formula (IXa) to a heterocyclization step to form the compound of formula (VIIIb); subjecting the compound of formula (VIII) to deprotection of the hydroxyl protection group to form the compound of formula (VII);
andoxidizing the compound of formula (VII) to form the compound of formula (IV); (b) reacting the compound of formula (IV) with R6—
NH2 to form the compound of formula (II); and(c) reacting a compound of formula (II) with T-Z-R7 in the presence of a base, to form to compound of claim 1, wherein P, Q, V, W, X, Y, R3, R4, R5, R6, R7, Z, and a are as defined in claim 1.
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Specification
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Current AssigneeAventis Agriculture, Merial Incorporated (C.H. Boehringer Sohn AG & Co. KG)
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Original AssigneeAventis Agriculture, Merial Limited (C.H. Boehringer Sohn AG & Co. KG)
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InventorsSoll, Mark David, Wilkinson, Douglas Edward, Lee, Hyoung Ik, Huber, Scot Kevin, Jacobs, Robert Toms, Fallois, Loic Patrick Le Hir de
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current514/303
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CPC Class CodesA61P 33/00 Antiparasitic agentsA61P 33/10 AnthelminticsA61P 33/12 SchistosomicidesA61P 33/14 Ectoparasiticides, e.g. sca...C07D 231/56 Benzopyrazoles; Hydrogenate...C07D 249/18 Benzotriazoles
