Anthelmintic compounds
AssigneeMerial Limited
InventorsAlan Long, Srinivas Reddy Gurrala
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel anthelmintic compounds of formula (I) below: wherein Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group, or one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl, and variables X1, X6, X8, Q1, Q2, Q3, Q4, Q5, Q6, Ring A, Ring B, W, W′, R2, R3, R, R′, m, n and q are as defined herein. The invention also provides for veterinary compositions comprising the anthelmintic compounds of the invention, and their uses for the treatment and prevention of parasitic infections in animals.
Claims21
An anthelmintic compound of formula (IA-1):
- wherein
- Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group optionally independently substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- or
- one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group optionally substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl, and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl;
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl and heteroaryl groups are optionally independently substituted with one or more of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- X1 is a bond, —O—, —C(O)—, —C(S)—, —NH—, —S, —S(O), —S(O)2—, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n— where n is 1 to 3, —C(O)—CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O—, —NHCH2—, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2—, or —CH2—S(O)2—, wherein each NH, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n, —C(O)CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O, —NH—CH2, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2— and —CH2—S(O)2— is optionally independently substituted with oxo (═O) or one or two substituents selected from the group consisting of halogen, cyano, hydroxy, hydroxyalkyl, alkoxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl or aryl groups, where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino and carboxy (—COOH);
- X6 is a bond, —(CH2)n— where n is 1 to 3, —O—, —C(O)—, —C(S)—, —S—, —S(O)—, —S(O)2—, —NH—, —C(O)—NH—, —C(S)—NH—, —NH—C(O)—, —NH—C(S)—, wherein each —CH2— in the —(CH2)n— group, —NH—, —C(O)—NH—, —C(S)—NH—, —NH—C(O)—, —NH—C(S)— is optionally independently substituted with one or two substituents selected from the group consisting of halogen, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, halocarbocyclyl, carbocyclylalkyl and halocarbocyclylalkyl;
- X8 is a bond, —(CH2)n where n is 1 to 3, —O—, —C(O)—, —S—, —S(O)—, —S(O)2—, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, or —NH—, wherein each CH2 in —(CH2)n—, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH— or the —NH— is optionally independently substituted with one or two substituents selected from the group consisting of halogen, hydroxy, amino, alkylamino, dialkylamino, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl and oxo (═O), where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino or carboxy (—COOH);
- Ring A and Ring B are each independently a 3- to 8-membered carbocyclic or heterocyclic ring where Q1, Q2, Q5 and Q6 are independently N or CR4 where R4 is H, OH, halogen or C1-3alkyl, or a spirocyclic ring system comprising two carbocyclic rings, two heterocyclic rings or a carbocyclic-heterocyclic ring system joined at one carbon, wherein each ring of the spirocyclic linker contains 4, 5 or 6 ring atoms;
- with the proviso that at least one of Ring A and Ring B is an azetidine ring linker or a spirocyclic carbocyclic, heterocyclic or a spirocyclic carbocyclic-heterocyclic ring system;
- W is O, S or an oxetane group;
- Q3 and Q4 are each independently C—R1 or a ring heteroatom selected from N, S or O;
- each R1 is independently hydrogen, halogen, cyano, hydroxyl, amino, alkylamino, dialkylamino, alkyl, haloalkyl, carbocyclyl, heterocyclyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
- R2 and R3 are independently hydrogen, halogen, cyano, alkyl, haloalkyl or carbocyclyl;
- n is 0, 1, 2 or 3;
- m is 0, 1, 2, 3 or 4;
- and
- q is 0, 1, 2, 3 or 4.
An anthelmintic compound of formula (IA-2):
- wherein
- Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group optionally independently substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- or
- one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group optionally substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl, and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl;
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl and heteroaryl groups are optionally independently substituted with one or more of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- X1 is a bond, —O—, —C(O)—, —C(S)—, —NH—, —S, —S(O), —S(O)2—, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n— where n is 1 to 3, —C(O)—CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O—, —NHCH2—, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2—, or —CH2—S(O)2—, wherein each NH, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n, —C(O)CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O, —NH—CH2, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2— and —CH2—S(O)2— is optionally independently substituted with oxo (═O) or one or two substituents selected from the group consisting of halogen, cyano, hydroxy, hydroxyalkyl, alkoxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl and aryl groups, where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino or carboxy (—COOH);
- X8 is a bond, —(CH2)n where n is 1 to 3, —O—, —C(O)—, —S—, —S(O)—, —S(O)2—, NHS(O)—, —S(O)—NH—, NHSO2—, —SO2NH—, or —NH—, wherein each CH2 in —(CH2)n— —NHS(O)—, S(O)—NH—, NHSO2—, —SO2NH— or the —NH— is optionally independently substituted with one or two substituents selected from the group consisting of halogen, hydroxy, amino, alkylamino, dialkylamino, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl and oxo (═O), where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino or carboxy (—COOH);
- Ring A and Ring B are each independently a 3- to 8-membered carbocyclic or heterocyclic ring where Q1, Q2, Q5 and Q6 are independently N or CR4 where R4 is H, OH, halogen or C1-3alkyl, or a or a spirocyclic ring system comprising two carbocyclic rings, two heterocyclic rings or a carbocyclic-heterocyclic ring system joined at one carbon, wherein each ring of the spirocyclic linker contains 4, 5 or 6 ring atoms;
- with the proviso that at least one of Ring A and Ring B is an azetidine ring linker or a spirocyclic carbocyclic, heterocyclic or a spirocyclic carbocyclic-heterocyclic ring system;
- W is O, S or an oxetane group;
- Q3 and Q4 are each independently C—R1 or a ring heteroatom selected from N, S or O;
- each R1 is independently hydrogen, halogen, cyano, hydroxyl, amino, alkylamino, dialkylamino, alkyl, haloalkyl, carbocyclyl, heterocyclyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
- R2 and R3 are independently hydrogen, halogen, cyano, alkyl, haloalkyl or carbocyclyl;
- n is 0, 1, 2 or 3;
- m is 0, 1, 2, 3 or 4;
- and
- q is 0, 1, 2, 3 or 4.
An anthelmintic compound of formula (IB-2):
- wherein
- Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group optionally independently substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- or
- one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group optionally substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl, and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl;
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl and heteroaryl groups are optionally independently substituted with one or more of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- X1 is a bond, —O—, —C(O)—, —C(S)—, —NH—, —S, —S(O), —S(O)2—, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n— where n is 1 to 3, —C(O)—CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O—, —NHCH2—, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2—, or —CH2—S(O)2—, wherein each NH, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n, —C(O)CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O, —NH—CH2, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2— and —CH2—S(O)2— is optionally independently substituted with oxo (═O) or one or two substituents selected from the group consisting of halogen, cyano, hydroxy, hydroxyalkyl, alkoxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl or aryl groups, where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino and carboxy (—COOH);
- X6 is a bond, —(CH2)n— where n is 1 to 3, —O—, —C(O)—, —C(S)—, —S—, —S(O)—, —S(O)2—, —NH—, —C(O)—NH—, —C(S)—NH—, —NH—C(O)—, —NH—C(S)—, wherein each —CH2— in the —(CH2)n— group, —NH—, —C(O)—NH—, —C(S)—NH—, —NH—C(O)—, —NH—C(S)— is optionally independently substituted with one or more substituents independently selected from the group consisting of halogen, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, halocarbocyclyl, carbocyclylalkyl and halocarbocyclylalkyl;
- X8 is a bond, —(CH2)n where n is 1 to 3, —O—, —C(O)—, —S—, —S(O)—, —S(O)2—, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, or —NH—, wherein each CH2 in —(CH2)n— —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH— or the —NH— is optionally independently substituted with one or two substituents selected from the group consisting of halogen, hydroxy, amino, alkylamino, dialkylamino, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl and oxo (═O), where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino or carboxy (—COOH);
- W and W′ are each independently O or S;
- Q1 and Q2 are each independently C—H or N;
- the ring is an azetidine ring or a spirocyclic ring system comprising two carbocyclic rings, two heterocyclic rings or a carbocyclic-heterocyclic ring system joined at one carbon, wherein each ring of the spirocyclic linker contains 4, 5 or 6 ring atoms;
- R and R′ are each independently hydrogen, alkyl, haloalkyl or arylalkyl;
- R2 and R3 are independently hydrogen, halogen, cyano, alkyl, haloalkyl or carbocyclyl;
- and
- n is 0, 1, 2 or 3.
An anthelmintic compound of formula (IB-4):
- Wherein
- Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group optionally independently substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- or
- one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group optionally substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl, and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl;
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl and heteroaryl groups are optionally independently substituted with one or more of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- X1 is a bond, —O—, —C(O)—, —C(S)—, —NH—, —S, —S(O), —S(O)2—, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n— where n is 1 to 3, —C(O)—CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O—, —NHCH2—, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2—, or —CH2—S(O)2—, wherein each NH, —NHS(O)—, —S(O)—NH—, —NHSO2—, —SO2NH—, —(CH2)n, —C(O)CH2—, —CH2—C(O)—, —O—CH2—, —CH2—O, —NH—CH2, —CH2—NH—, —S—CH2—, —CH2—S—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2— and —CH2—S(O)2— is optionally independently substituted with oxo (═O) or one or two substituents selected from the group consisting of halogen, cyano, hydroxy, hydroxyalkyl, alkoxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl or aryl groups, where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino and carboxy (—COOH);
- X6 is a bond, —(CH2)n— where n is 1 to 3, —O—, —C(O)—, —C(S)—, —S—, —S(O)—, —S(O)2—, —NH—, —C(O)—NH—, —C(S)—NH—, —NH—C(O)—, —NH—C(S)—, wherein each —CH2— in the —(CH2)n— group, —NH—, —C(O)—NH—, —C(S)—NH—, —NH—C(O)—, —NH—C(S)— is optionally independently substituted with one or two substituents independently selected from the group consisting of halogen, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, halocarbocyclyl, carbocyclylalkyl and halocarbocyclylalkyl;
- X8 is a bond, —(CH2)n where n is 1 to 3, —O—, —C(O)—, —S—, —S(O)—, —S(O)2—, NHS(O)—, —S(O)—NH—, NHSO2—, —SO2NH—, or —NH—, wherein each CH2 in —(CH2)n— —NHS(O)—, S(O)—NH—, NHSO2—, —SO2NH— or the —NH— is optionally independently substituted with one or two substituents selected from the group consisting of halogen, hydroxy, amino, alkylamino, dialkylamino, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl and oxo (═O), where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino or carboxy (—COOH);
- W and W′ are each independently O or S;
- Q1 and Q2 are each independently C—H or N;
- the ring is an azetidine ring or a spirocyclic ring system comprising two heterocyclic rings or a carbocyclic-heterocyclic ring system joined at one carbon, wherein each ring of the spirocyclic linker contains 4, 5 or 6 ring atoms;
- R and R′ are each independently hydrogen, alkyl, haloalkyl or arylalkyl;
- R2 and R3 are independently hydrogen, halogen, cyano, alkyl, haloalkyl or carbocyclyl;
- and
- n is 0, 1, 2 or 3.
An anthelmintic compound of formula (IC-1):
- wherein
- Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group optionally independently substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- or
- one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group optionally substituted by one or more of halogen, nitro, cyano, hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino, aminoalkyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl, and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl;
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl and heteroaryl groups are optionally independently substituted with one or more of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, halothio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aryl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylsulfinyl, aryl sulfonyl, arylalkylsulfinyl, arylalkylsulfonyl, heteroaryl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylalkylthio, heteroarylalkylsulfinyl or heteroarylalkylsulfonyl;
- X1 is a bond, —C(O)—, —C(S)—, —NH—, —S(O)—, —S(O)2—, —(CH2)n— where n is 1 to 3, —O—CH2—, —NHCH2—, —S—CH2—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2—, or —CH2—S(O)2—, wherein each —NH—, —(CH2)n—, —O—CH2—, —NHCH2—, —S—CH2—, —S(O)—CH2—, —CH2—S(O)—, —S(O)2—CH2—, and —CH2—S(O)2— is optionally independently substituted with oxo (═O) or one or two substituents selected from the group consisting of halogen, cyano, alkyl, haloalkyl, aryl groups, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl and heterocyclylalkyl, where each substituent may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino and carboxy (—COOH);
- X8 is a bond, —(CH2)n where n is 1 to 3, —O—, —C(O)—, —S—, —S(O)—, —S(O)2—, NHS(O)—, —S(O)—NH—, NHSO2—, —SO2NH—, or —NH—, wherein each CH2 in —(CH2)n— —NHS(O)—, S(O)—NH—, NHSO2—, —SO2NH— or the —NH— is optionally independently substituted with one or two substituents selected from the group consisting of halogen, hydroxy, amino, alkylamino, dialkylamino, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbocyclyl, heterocyclyl, carbocyclylalkyl, heterocyclylalkyl and oxo (═O), where each substituent group may be further independently substituted by hydroxy, hydroxyalkyl, amino, alkylamino, dialkylamino or carboxy (—COOH);
- Ring A is a 3 to 8-membered monocyclic carbocyclic or heterocylic ring wherein Q5 and Q6 are independently N or CR4 where R4 is H, halogen, OH or C1-3alkyl;
- Q4 is a ring N, S or O atom or —CR4
- W is O or S;
- R2 and R3 are independently hydrogen, halogen, cyano, alkyl, haloalkyl or carbocyclyl;
- and
- n is 1, 2 or 3.
Dependencies are inferred from the claim text.