Anthelmintic compounds comprising a pyridine structure

A Compound of Formula (I)

• wherein
• L is independently selected from
• being absent, —CH2—, —NRL—, —O—, —S—, —S(O)— and —S(O)2—, with RL being independently selected from hydrogen and C1-3-alkyl,
• R1 is independently selected from the group consisting of
• hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10 aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy, C1-6-alkylmercapto, halogen, cyano, nitro, hydroxy, mercapto, NR2R3, COOH, C(═O)OR4, SR4, S(O)R4, S(O)2R4, S(O)2NR5R6 and C(═O)NR5R6,
• wherein each C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10 aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy or C1-6-alkylmercapto, is optionally substituted with one or more substituent(s) independently selected from the group consisting of
• C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy, C1-6-alkylmercapto, halogen, cyano, nitro, hydroxy, mercapto, NR2′R3′, C(═O)OR4′, SR4′, S(O)R4′, S(O)2R4′, S(O)2NR5′R6′ and C(═O)NR5′R6′,
• R2 and R3 are independently selected from the group consisting of
• hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy-C1-6-alkyl, C1-6-alkyl substituted with C3-10-cycloalkyl, C1-6-alkyl substituted with 4 to 10-membered heterocyclyl, C1-6-alkyl substituted with C6-10-aryl and C1-6-alkyl substituted with 5 to 10-membered heteroaryl, or
• R2 and R3 together with the N atom to which they are attached form a saturated or unsaturated heterocyclic ring having 3 to 12 ring atoms, wherein 0, 1, 2 or 3 further ring atoms are selected from N, S and O,
• wherein each C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy-C1-6-alkyl, C1-6-alkyl substituted with C3-10-cycloalkyl, C1-6-alkyl substituted with 4 to 10-membered heterocyclyl, C1-6-alkyl substituted with C6-10-aryl, C1-6-alkyl substituted with 5 to 10-membered heteroaryl or the heterocyclic ring formed by R2 and R3 together with the N atom to which they are attached is optionally substituted with one or more substituent(s) independently selected from the group consisting of
• C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy, carbonyl, halogen, cyano, hydroxy, mercapto, NR2″R3″, C(═O)OR4″, SR4″, S(O)R4″, S(O)2R4″, S(O)2NR5″R6″ and C(═O)NR5″R6″,
• R4, R5 and R6 are independently selected from hydrogen and C1-6-alkyl,
• R2′, R3′, R4′, R5′ and R6′ are independently selected from hydrogen and C1-6-alkyl,
• R2″, R3″, R4″, R5″ and R6″ are independently selected from hydrogen and C1-6-alkyl,
• R7 is independently selected from the group consisting of
• methyl, ethyl, isopropyl, isopropenyl, methoxy, ethoxy, isopropoxy, hydroxy, methylmercapto, ethylmercapto, methyl sulfoxyl, methyl sulfonyl, methylthio, amino, methylamino, ethylamino, isopropylamino, dimethylamino, isopropylmethylamino, hydroxyethylamino, methoxyethylamino, morpholin-4-yl, 4-methylpiperazin-1-yl, 3-hydroxy-pyrrolidin-1-yl, 3-fluoroazetidin-1-yl and 3,3-difluoroazetidin-1-yl,
• R8 and R9 are independently selected from the group consisting of
• hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy-C1-6-alkyl, C1-6-alkyl substituted with C3-10-cycloalkyl, C1-6-alkyl substituted with 4 to 10-membered heterocyclyl, C1-6-alkyl substituted with C6-10-aryl and C1-6-alkyl substituted with 5 to 10-membered heteroaryl, or
• R8 and R9 together with the N atom to which they are attached form a saturated or unsaturated heterocyclic ring having 3 to 12 ring atoms, wherein 0, 1, 2 or 3 further ring atoms are selected from N, S and O,
• wherein each C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy-C1-6-alkyl, C1-6-alkyl substituted with C3-10-cycloalkyl, C1-6-alkyl substituted with 4 to 10-membered heterocyclyl, C1-6-alkyl substituted with C6-10-aryl, C1-6-alkyl substituted with 5 to 10-membered heteroaryl or the heterocyclic ring formed by R8 and R9 together with the N atom to which they are attached is optionally substituted with one or more substituent(s) independently selected from the group consisting of
• C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy, carbonyl, halogen, cyano, hydroxy, mercapto, NR8″R9″, C(═O)OR10″, SR10″, S(O)R10″, S(O)2R10″, S(O)2NR11″R12″ and C(═O)NR11″R12″,
• R10, R11 and R12 are independently selected from hydrogen and C1-6-alkyl,
• R8′, R9′, R10′, R11′ and R12′ are independently selected from hydrogen and C1-6-alkyl,
• R8″, R9″, R10″, R11″ and R12″ are independently selected from hydrogen and C1-6-alkyl,
• R13 and R14 together with the atoms to which they are attached form a 5 or 6-carbon atoms containing saturated ring, wherein the saturated ring is optionally substituted with one or more C1-3-alkyl or ═O, and/or wherein one or more of the ring-forming carbon atoms are optionally replaced by —NH—, —O—, —S(O)—, —S(O)2— or —S—, or
• R13 and R14 together with the atoms to which they are attached form a 5 or 6-carbon atoms containing unsaturated ring, wherein the unsaturated ring is optionally substituted with one or more C1-3-alkyl, and/or wherein one or more of the ring-forming carbon atoms are optionally replaced by —NH—, —N═, =N—, —O— or —S—,
• A1 is N or CR15, wherein R15 is independently hydrogen, halogen, C1-3 alkyl, C1-3 alkoxy, or NR15′R15″, wherein R15′ and R15″ are independently C1-3-alkyl,
• A2 is N or CR16, wherein R16 is independently hydrogen, halogen, C1-3 alkyl, C1-3 alkoxy, or NR16′R16″, wherein R16′ and R16″ are independently C1-3-alkyl,
• A3 is N or CR17, wherein R17 is independently hydrogen, halogen, C1-3 alkyl, C1-3 alkoxy, or NR17′R17″, wherein R17′ and R17″ are independently C1-3-alkyl,
• A4 is N or CR18, wherein R18 is independently hydrogen, halogen C1-3 alkyl, C1-3 alkoxy, or NR18′R18″, wherein R18′ and R18″ are independently C1-3-alkyl,
• R19 is independently selected from the group consisting of
• C6-10-aryl and 5 to 10-membered heteroaryl,
• wherein each C6-10-aryl or 5 to 10-membered heteroaryl is optionally substituted with one or more substituent(s) independently selected from the group consisting of
• C1-6-alkyl, C2-6-alkenyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy, C1-6-alkylmercapto, halogen, cyano, nitro, hydroxy, mercapto, NR20R21, C(═O)OR22, SR22, S(O)R22, S(O)2R22, S(O)2NR23R24 and C(═O)NR23R24,
• R20 and R21 are independently selected from the group consisting of
• hydrogen, C1-6-alkyl, C3-10-cycloalkyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy-C1-6-alkyl, C1-C6-alkyl substituted with C6-10-aryl and C1-6-alkyl substituted with 5 to 10-membered heteroaryl, or
• R20 and R21 together with the N atom to which they are attached form a saturated or unsaturated heterocyclic ring having 3 to 12 ring atoms, wherein 0, 1, 2 or 3 further ring atoms are selected from N, S and O,
• wherein each C1-6-alkyl, C2-6-alkenyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy, C1-6-alkylmercapto or the heterocyclic ring formed by R20 and R21 together with the N atom to which they are attached is optionally substituted with one or more substituents independently selected from the group consisting of
• C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, 4 to 10-membered heterocyclyl, C6-10-aryl, 5 to 10-membered heteroaryl, C1-6-alkoxy, carbonyl, halogen, cyano, hydroxy, mercapto, NR20′R21′, C(═O)OR22′, SR22′, S(O)R22′, S(O)2R22′, S(O)2NR23′R24′ and C(═O)NR23′R24′,
• R22, R23 and R24 are independently selected from hydrogen and C1-6-alkyl,
• R20′, R21′, R22′, R23′ and R24′ are independently selected from hydrogen and C1-6-alkyl,
• R25 is independently selected from hydrogen and C1-6-alkyl,
• or a stereoisomer, physiologically acceptable salt, ester, solvate, polymorph, prodrug and mixtures thereof.