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US 10,047,040 B2Granted
Sulfonylaminobenzamide compounds as anthelmintics
AssigneeElanco Tiergesundheit AG
InventorsNoelle Gauvry, Chouaib Tahtaoui
Life of this patent
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Abstract
The present invention relates to a new compound of formula (I) wherein the variables have the meaning as indicated in the claims; or an enantiomer or salt thereof. The compounds of formula (I) are useful in the control of parasites, in particular endoparasites, in and on vertebrates.
Claims15
A compound of formula
- or a salt or an enantiomer thereof, wherein
- n is 1;
- A is a phenyl radical which is substituted by chlorine, fluorine or CF3;
- R2 is H or —S(O2)-T;
- T is C1-C6-alkyl which is unsubstituted or substituted by halogen, trimethylsilyl, C3-C6-cycloalkyl, carboxyl or C1-C4-alkoxycarbonyl;
- C3-C6-cycloalkyl;
- C6-C12-bicarbocyclyl;
- phenyl which is unsubstituted or substituted by halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy;
- a 5- or 6 membered heteroaromatic radical, which is further unsubstituted or substituted by halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy;
- 5- or 6-membered heterocycloalkyl having from 1 to 3 same or different heteroatoms selected from the group consisting of N, O, S and S(O2), which is further unsubstituted or substituted by C1-C4-alkyl, C1-C2-alkoxycarbonyl or benzyloxycarbonyl;
- a group
- amino;
- or N-mono- or N,N-di-C1-C4-alkylamino;
- R3 is C1-C4-alkyl, unsubstituted or halogen-, C1-C4-alkyl- or C1-C4-haloalkyl-substituted phenyl, unsubstituted or halogen-, C1-C4-alkyl- or C1-C4-haloalkyl-substituted pyridyl, C1-C4-alkoxycarbonyl-methyl or morpholin-4-yl-carbonylmethyl;
- R0 is H or hydroxy;
- and
- Y is
- (i) phenyl or a phenylamino, which is substituted by one or more same or different radicals selected from the group consisting of halogen;
- C1-C2-alkyl;
- C1-C3-haloalkyl;
- C1-C2-alkoxy;
- C1-C3-haloalkoxy;
- C1-C2-haloalkylthio;
- SF5;
- cyano;
- nitro;
- hydroxy;
- or methylsulfonylamino;
- or is
- (ii) 5- or 6 membered heteroaryl or heteroarylamino, which is each further unsubstituted or substituted by halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, C2-C4-alkanoyl, or phenyl or phenylsulfonyl which is each unsubstituted or substituted by halogen, cyano, nitro, methyl or methoxy;
- or is
- (iii) benzoyl or 5- or 6 membered heteroarylcarbonyl, which is each further unsubstituted or substituted by halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl, C2-C4-alkanoyl or phenyl;
- or is
- (iv) a C6-C12-bicarbocyclic radical;
- or is a
- (v) a hetero-bicyclic ring radical comprising a total of 8 to 10 ring members, from which 1 to 5 members are same or different heteroatoms selected from the group consisting of B, N, O and S, and from which 0 to 2 members are a group —C(O)—, which bicyclic ring radical is further unsubstituted or substituted by halogen, cyano, hydroxyl, C1-C4-alkoxy, C1-C4-alkyl or C1-C4-haloalkyl;
- or is
- (vi) a radical —H2C—C(O)—NH—R4, wherein R4 is C1-C4-haloalkyl, C2-C3-alkynyl or cyano-C1-C4-alkyl;
- or
- R0 and Y together with the N-atom to which they are attached, form a piperidinyl or piperazinyl radical which is substituted by C1-C4-alkyl, C1-C4-alkoxy, unsubstituted or halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, amino- and/or C1-C4-alkoxy-substituted phenyl or benzoylamino, or unsubstituted or C1-C4-alkyl-, C1-C4-haloalkyl-, C3-C6-cycloalkyl- or halogen-substituted pyridyl or pyrimidinyl;
- subject to the proviso that
- at least one of A and Y must not be a phenyl radical if T is CH3.
39 more elements
A compound of the formula:
- wherein
- (R)m is H or 4-Cl;
- T is 4-CH3-phenyl, phenyl, 2-NO2-4-CF3-phenyl, 3-Cl-4-F-phenyl, 2-CF3-4-F-phenyl, 4-CF3-phenyl, 3,4-dimethoxyphenyl, 4-nitrophenyl, 4-chlorophenyl, 3,5-di-Cl-phenyl, 4-methoxyphenyl, 2-chloro-phenyl, 3-chloro-phenyl, 3-pyridyl, 3-methoxyphenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2-methoxyphenyl, 2,4-dichlorophenyl, 2-NO2-4-OCH3-phenyl, 2,4-dimethoxyphenyl, ethyl, —CH2CF3, —CH2CH2CF3, n-propyl, n-butyl, iso-butyl, —CH2CH2Si(CH3)3, cyclopropyl, cyclohexyl, 1-(benzyloxycarbonyl)-piperazin-4-yl, isopropyl, cyclohexylmethyl, (1R)-(−-campher, —CH2C(O)OC2H5, —CH2C(O)OCH3, —CH2C(O)OH, (1S)-(+)-campher, tetrahydro-2H-pyran-4-yl, —N(CH3)2, 1-methylpiperazin-4-yl, —CH2—Cl,
- and
- R2 is H or —SO2CH2Cl.
2 more elements
A compound of the formula:
- wherein
- R0 is H or hydroxy;
- and
- Y is
- or R0 and Y together with the N-atom to which they are attached, form
2 more elements
Dependencies are inferred from the claim text.