IP Library Patent Application 15477343
Patent Application
App. No. 15/477,343

ANTIPARASITIC COMPOUNDS

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Patent No.
US None
App. No.
15/477,343
Abstract

The invention relates to 1,2,4-thiadiazole derivatives and their use to treat parasites.

Claims (183)

1 - 18 . (canceled)

19 . A method for controlling parasites at a locus which comprises applying to the locus an effective amount of a thiadiazole derivative of formula (I)

wherein:

A is C═O or SO 2 ;

X is R 1 or NHR 1 ;

R 1 is:

phenyl optionally substituted by from one to three substituents, which are the same or different, each selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

naphthyl optionally substituted by from one to three substituents, which are the same or different, each independently selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

quinoxolinyl optionally substituted by from one to three substituents, which are the same or different, each independently selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

quinolinyl optionally substituted by from one to three substituents, which are the same or different, each independently selected from the group consisting nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto, thioalkyl and halogen;

or thionyl or furyl optionally substituted by from one to three substituents which are the same or different, each selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, —SO 2 R 5 , —NR 3 SO 2 R 5 , —SO 2 NR 3 R 4 , —CONR 3 R 4 , —CONHC 6 H 5 , hydroxy, alkoxy, aryloxy, aryl, heterocyclyl, haloalkyl, haloalkoxy, mercapto (—SH), thioalkyl and halogen;

R 2 is hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy, aminoalkyl, alkylaminoalkyl, aryl, heterocyclyl or —CONR 3 R 4 ; or R 2 , together with two adjacent carbons of the pyridyl ring to which it is attached, forms a saturated or unsaturated ring containing from 4 to 6 ring atoms;

R 3 and R 4 , which are the same or different, each independently represent hydrogen or alkyl; or when R 3 and R 4 are each attached to a nitrogen atom, they may form a saturated or unsaturated heterocyclic ring containing from 4 to 6 ring atoms

R 5 is alkyl or haloalkyl;

or a pesticidally acceptable salt thereof.

20 . The method of claim 19 wherein controlling parasites comprises treating or preventing parasite infection in a subject in need thereof.

21 . The method of claim 19 , wherein:

A is C═O;

X is R 1 ;

R 1 is phenyl substituted by from one to three substituents which are the same or different selected from the group consisting of trifluoromethyl, trifluoromethoxy, chloro, fluoro, cyano, methyl, ethyl, methoxy, ethoxy, aryloxy, thiomethyl, —SO 2 CH 3 , —SO 2 NH 2 , —SO 2 NHCH 3 , —SO 2 N(CH 3 ) 2 and —NHSO 2 CH 3 ; and

R 2 is hydrogen, fluoro, methyl, trifluoromethyl, methoxy, trifluoromethoxy, morpholino, aminoalkyl or dimethylaminomethyl.

22 . The method of claim 19 , wherein:

A is SO 2 ;

X is R 1 ;

R 1 is phenyl substituted by from one to three substituents which are the same or different selected from the group consisting of trifluoromethyl, trifluoromethoxy, chloro, fluoro, cyano, methyl, ethyl, methoxy, ethoxy, thiomethyl, methanesulfonyl, sulfonamide, methylsulfonamide, dimethylsulfonamide, and methylsulfonanilide; and

R 2 is hydrogen.

23 . The method of claim 19 , wherein:

A is C═O or SO 2 ;

X is R 1 or NHR 1 ;

R 1 is:

phenyl optionally substituted by from one to three substituents which are the same or different, each selected from the group consisting of nitro, —NR 3 R 4 , cyano, —NR 3 COR 5 , alkyl, alkoxy, aryl, heterocyclyl, aryloxy, haloalkyl, haloalkoxy, mercapto (—SH), thioalkyl and halogen;

R 2 is hydrogen, fluoro, methyl, trifluoromethyl, methoxy, trifluoromethoxy, morpholino, aminoalkyl or dimethylaminomethyl.

24 . The method of claim 19 , wherein the compound is selected from one or more of:

1-(4-methoxyphenyl)-3-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]urea;

1-(2-chlorophenyl)-3-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]urea;

1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[4-(trifluoromethyl)phenyl]urea;

1-(3-methoxyphenyl)-3-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]urea;

1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[4-(trifluoromethoxy)phenyl]urea;

1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[3-(trifluoromethyl)phenyl]urea;

4-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-cyano-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]naphthalene-2-carboxamide;

4-trifluoromethoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

2-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

4-cyano-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

4-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

2-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethyl)benzenesulfonamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzenesulfonamide;

N-[3-(3-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-morpholino-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[benzyl(methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(dimethylamino)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[2-methoxyethyl)methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-methoxy-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-methoxy-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(triazolo[4,5-b]pyridin-3-yloxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-bromo-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

methyl 2-[5-[[4-(trifluoromethyl)benzoyl]amino]-1,2,4-thiadiazol-3-yl]pyridine-4-carboxylate;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]isoquinoline-7-carboxamide;

4-acetamido-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-nitro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]quinoxaline-6-carboxamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]thiophene-2-carboxamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]thiophene-3-carboxamide;

N-[3-(4-isopropyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(3-isoquinolyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-methyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

3-chloro-4-fluoro-N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy)benzamide;

4-tert-butyl-N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-3,5-bis(trifluoromethyl)benzamide;

N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethyl)benzamide;

3,4-dichloro-N-[3-(5-fluoro-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-methylsulfonyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]isoquinoline-5-carboxamide;

3-chloro-4-(4-methylpiperazin-1-yl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

methyl 4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoate;

4-(diethylsulfamoyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-methyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]thiophene-2-carboxamide;

3-chloro-4-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

2-fluoro-3-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethyl)benzamide;

2,5-dimethyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]furan-3-carboxamide;

4-tert-butyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-1,3-benzodioxole-5-carboxamide;

3,4-dichloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3,5-bis(trifluoromethyl)benzamide;

4-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-phenoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethyl)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoic acid;

4-iodo-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-morpholino-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(morpholine-4-carbonyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

tert-butyl 4-[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoyl]piperazine-1-carboxylate;

tert-butyl 4-[[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]benzoyl]amino]piperidine-1-carboxylate;

4-(piperidine-1-carbonyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(piperazine-1-carbonyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

4-(2-pyridylamino)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

tert-butyl 4-[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]anilino]piperidine-1-carboxylate;

4-phenyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-piperazin-1-yl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(4-piperidylamino)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

tert-butyl 4-[4-[[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]carbamoyl]phenyl]piperazine-1-carboxylate;

3-chloro-2-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(1,1,2,2-tetrafluoroethoxy)benzamide;

2-methoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy)benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl)furan-2-carboxamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl)thiophene-2-carboxamide;

4-formyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-[hydroxy(phenyl)methyl]-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-bromo-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-benzyl-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N4-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

4-bromo-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-chloro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy)benzamide;

N-[3-(4-phenyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(trifluoromethyl)-N-[3-[5-(trifluoromethyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]benzamide;

N4-phenyl-N1-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethyl) benzamide;

2-fluoro-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethoxy) benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-2-(trifluoromethoxy) benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-(trifluoromethoxy) benzamide;

4-(4-fluorophenoxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl] benzamide;

3-hydroxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-5-(trifluoromethyl) thiophene-2-carboxamide;

4-(2,4-difluorophenoxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-[4-(trifluoromethyl)phenoxy] benzamide;

N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]-3-[4-(trifluoromethyl)phenoxy]benzamide;

3-(4-fluorophenoxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-phenoxy-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N1-(4-piperidyl)-N4-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]terephthalamide;

N-[3-(5-piperazin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(4-piperidyloxy)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]pyridine-2-carboxamide;

N-[3-(6-piperazin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(3-pyridyl)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl] benzamide;

N-[3-(5-phenyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-(trifluoromethyl)-N-[3-(5-vinyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-[5-(3,6-dihydro-2H-pyran-4-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(6-phenyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[6-(3-pyridyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

4-anilino-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

4-(benzylamino)-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

3-anilino-N-[3-(2-pyridyl)-1,2,4-thiadiazol-5-yl]benzamide;

N-[3-[5-(3-pyridylamino)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-morpholino-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-[2-methoxyethyl(methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-pyrrolidin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-(2-pyridylamino)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-(4-methylpiperazin-1-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

tert-butyl 4-[6-[5-[[4-(trifluoromethyl)benzoyl]amino]-1,2,4-thiadiazol-3-yl]-3-pyridyl]piperazine-1-carboxylate;

N-[3-[5-(1-piperidyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(5-anilino-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[5-(4-hydroxy-1-piperidyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[6-(4-methylpiperazin-1-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

tert-butyl 4-[6-[5-[[4-(trifluoromethyl)benzoyl]amino]-1,2,4-thiadiazol-3-yl]-2-pyridyl]piperazine-1-carboxylate;

N-[3-(4-Methyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(6-Methyl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(dimethylaminomethyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[methyl-[2-(1-piperidyl)ethyl]amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[methyl(2-morpholinoethyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-pyrrolidin-1-yl-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(4-methylpiperazin-1-yl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[2-hydroxyethyl(methyl)amino]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[2-(1-piperidyl)ethoxy]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(2-methoxyethoxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(2-dimethylaminoethyloxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(2,2-dimethylpropoxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-[(1-methyl-4-piperidyl)oxy]-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-(4-tetrahydropyran-4-yloxy-2-pyridyl)-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide;

N-[3-[4-(oxetan-3-yloxy)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide; and

N-[3-[4-(hydroxymethyl)-2-pyridyl]-1,2,4-thiadiazol-5-yl]-4-(trifluoromethyl)benzamide,

or a pesticidally acceptable salt thereof.

25 . The method of claim 19 , wherein the parasite is a helminth.

26 . The method of claim 19 , wherein the parasite is dirofilaria immitis.

Assignments (4)
RELEASE OF FIRST LIEN SECURITY INTEREST IN PATENTS Recorded Mar 6, 2025
From: ROYAL BANK OF CANADA
To: CAMBREX CHARLES CITY, INC.; AVISTA PHARMA SOLUTIONS, INC.; SNAPDRAGON CHEMISTRY, INC.
Reel/Frame 070438/0333 →
RELEASE OF SECOND LIEN SECURITY INTEREST IN PATENTS Recorded Dec 7, 2020
From: ROYAL BANK OF CANADA, AS COLLATERAL AGENT
To: AVISTA PHARMA SOLUTIONS, INC.
Reel/Frame 054630/0307 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Dec 4, 2019
From: CAMBREX CHARLES CITY, INC.; AVISTA PHARMA SOLUTIONS, INC.
To: ROYAL BANK OF CANADA, AS COLLATERAL AGENT
Reel/Frame 051196/0080 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Dec 4, 2019
From: AVISTA PHARMA SOLUTIONS, INC.; CAMBREX CHARLES CITY, INC.
To: ROYAL BANK OF CANADA, AS COLLATERAL AGENT
Reel/Frame 051283/0877 →