Substituted pyrrolo[1,2-b]pyridazines as anthelmintics

A compound of Formula (I):

• or a pharmaceutically acceptable salt or stereoisomer thereof,
• wherein:
• each independently is a single or double bond;
• R1 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), Si(alkyl)3, NRaRb, OH, O(alkyl), O(alkenyl), O(alkynyl), OSi(alkyl)3, O(aryl), SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), Si(alkyl)3, O(alkyl), O(alkenyl), O(alkynyl), O(aryl), OSi(alkyl)3, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;
• R1′ is H, halogen, alkyl, or haloalkyl;
• R2 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRaRb, OH, O(alkyl), O(aryl), SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), O(aryl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;
• R3 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRaRb, OH, O(alkyl), O(aryl), SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), O(aryl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;
• R4 is H, alkyl, alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRaRb, SF5, S(O)palkyl, cycloalkyl, cycloalkenyl, carbocyclyl-(spirocyclic carbocyclyl), carbocyclyl-(spirocyclic heterocyclyl), heterocyclyl, heterocyclyl-(spirocyclic carbocyclyl), heterocyclyl-(spirocyclic heterocyclyl), aryl, or 5- to 10-membered heteroaryl, wherein the alkyl, alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), S(O)palkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or 5- to 10-membered heteroaryl is optionally substituted with one or more independently selected substituents;
• each Ra is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;
• each Rb is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;
• or
• any Ra and Rb, taken together with the nitrogen atom to which they are attached, independently forms a 3- to 8-membered heterocyclyl;
• wherein each 3- to 8-membered heterocyclyl independently contains 0, 1, 2, or 3 additional heteroatoms independently selected from the group consisting of N, O, Si, and S;
• and
• wherein each 3- to 8-membered heterocyclyl is optionally and independently substituted with one or more independently selected substituents;
• L is (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L 11), (L12), (L13), (L14), (L15), (L16), or (L17):
• —C(X)NR′-(L1), —NR′C(X)-(L2), —NR′C(X)NR′-(L3), —S(NR′)(O)CH2-(L4), —CH2S(NR′)(O)-(L5), —S(O)2NR′-(L6), —NR′S(O)2-(L7), —S(O)2CH2-(L8), —CH2S(O)2-(L9), —CH(CF3)NR′-(L10), —NR′CH(CF3)-(L11), —CH(CHF2)NR′-(L12), —NR′CH(CHF2)-(L13),
• each X is independently NR′, O, or S;
• R′ is H, alkyl, haloalkyl, cycloalkyl, aralkyl, or aryl, wherein the alkyl, haloalkyl, cycloalkyl, aralkyl, or aryl is optionally substituted with one or more independently selected substituents;
• or
• two R′, together with the atoms to which they are attached, form a 2- to 4-membered carbon chain resulting in a 5- to 7-membered heterocyclyl;
• Y1 is C, CR5, or N;
• Y2 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
• Y3 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
• Y4 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
• Y5 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
• Y6 is C, CR5, or N;
• W is absent, CR6, —CR6R7—, N, —NR′—, —O—, or —S(O)p—;
• W1 is CR6, —CR6R7—, N, —NR′—, —O—, or —S(O)p—;
• Z is CR7, —CR6R7—, N, —NR′—, —O—, or —S(O)p—;
• Q is CR9;
• each R5 is independently H, halogen, CN, NO2, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRcRd, NHC(O)alkyl, OH, O(alkyl), OC(O)alkyl, SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, or heteroaryl, wherein each alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, and heteroaryl is optionally and independently substituted with one or more independently selected substituents;
• each R5′ is independently H, halogen, CN, NO2, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRcRd, NHC(O)alkyl, OH, O(alkyl), OC(O)alkyl, SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, or heteroaryl, wherein each alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, and heteroaryl is optionally and independently substituted with one or more independently selected substituents;
• or
• any R5 and R5′, taken together with the carbon atom to which they are attached, independently forms a 2- to 6-membered chain resulting in a 3- to 7-membered cyclyl;
• wherein each 3- to 7-membered cyclyl optionally and independently contains 1 or 2 heteroatoms independently selected from the group consisting of N, O, Si, and S;
• and
• wherein each 3- to 7-membered cyclyl is optionally and independently substituted with one or more independently selected substituents;
• each Rc is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;
• each Rd is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;
• or
• any Rc and Rd, taken together with the nitrogen atom to which they are attached, independently forms a 3- to 8-membered heterocyclyl;
• wherein each 3- to 8-membered heterocyclyl independently contains 0, 1, 2, or 3 additional heteroatoms independently selected from the group consisting of N, O, Si, and S;
• and
• wherein each 3- to 8-membered heterocyclyl is optionally and independently substituted with one or more independently selected substituents;
• each R6 is independently H, halogen, alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, or cycloalkoxy, wherein each alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, and cycloalkoxy is optionally and independently substituted with one or more independently selected substituents;
• each R7 is independently H, halogen, alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, or cycloalkoxy, wherein each alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, and cycloalkoxy is optionally and independently substituted with one or more independently selected substituents;
• or
• any R6 and R7, taken together with the carbon atom to which they are attached, independently forms a 2- to 6-membered chain resulting in a 3- to 7-membered cyclyl;
• wherein each 3- to 7-membered cyclyl optionally and independently contains 1 or 2 heteroatoms independently selected from the group consisting of N, O, Si, and S;
• and
• wherein each 3- to 7-membered cyclyl is optionally and independently substituted with one or more independently selected substituents;
• R8 is H or C1-C4 alkyl;
• R9 is H, halogen, alkyl, haloalkyl, alkenyl, alkynyl, or cycloalkyl;
• each p is independently 0, 1, or 2;
• and
• q is 0 or 1;
• wherein each optional substituent is independently selected from the group consisting of halogen, CN, NO2, alkyl, haloalkyl, CH(NH), CH(NOH), C(NH)NH2, C(O)alkyl, C(O)haloalkyl, C(O)NH2, C(O)NH(alkyl), C(O)NH(haloalkyl), C(O)N(alkyl)2, C(O)N(haloalkyl)2, C(O)OH, C(O)O(alkyl), C(O)O(haloalkyl), C(O)OC(O)R, C(O)SR, C(S)NH2, Si(R)3, NH2, NH(alkyl), NHC(NH)NH2, NHNH2, NH(aryl), N(alkyl)2, N(aryl)2, OH, O(alkyl), O(haloalkyl), OC(O)NH2, OC(O)OR, OSi(R)3, OP(O)(OR)(OR), OS(O)2OH, O(aryl), ═O, P(R)3, P(O)R, P(O)(R)2, P(O)(OR)(OR), P(O)(OR)NH2, SH, SF5, S(alkyl), S(haloalkyl), S(O)alkyl, S(O)haloalkyl, S(O)(NH)R, S(O)2alkyl, S(O)2haloalkyl, S(O)2NH2, S(O)2OH, S(O)2O(alkyl), cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl;
• and
• each R is independently alkyl, haloalkyl, or aryl;
• with the proviso that no more than three of Y1, Y2, Y3, Y4, Y5, and Y6 are heteroatoms.