US 11,964,977 B2
Anthelmintic heterocyclic compounds
Hannes Fiepko Koolman, Biberach an der Riss (DE); Bart Herlé, Biberach an der Riss (DE); and Alan Long, Biberach an der Riss (DE)
Assigned to Boehringer Ingelheim Animal Health USA Inc., Duluth, GA (US)
Filed by Boehringer Ingelheim Animal Health USA Inc., Duluth, GA (US); and BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG, Ingelheim am Rhein (DE)
Filed on May 19, 2021, as Appl. No. 17/324,288.
Claims priority of provisional application 63/031,656, filed on May 29, 2020.
Prior Publication US 2021/0380591 A1, Dec. 9, 2021
Int. Cl. A61K 31/5025 (2006.01); A61P 33/10 (2006.01); C07D 487/04 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 33/10 (2018.01)] 41 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
wherein:
L is L1, L2, L3, L4, L5, L6, L7, L8, L9, L10, L11, L12, L13, L14 or L15:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
R′ is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl;
R1 is hydrogen, cyano, halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted alkoxyalkyl, optionally substituted aminoalkyl, optionally substituted alkylaminoalkyl, optionally substituted dialkylaminoalkyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkoxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SOp (optionally substituted alkyl or haloalkyl), —SF5, or —NRaRb, wherein Ra and Rb are independently H or optionally substituted alkyl; or Ra and Rb may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R2 is hydrogen, cyano, halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl; optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkoxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SOp (optionally substituted alkyl or haloalkyl), —SF5, or —NRaRb, wherein Ra and Rb are independently H or optionally substituted alkyl; or Ra and Rb may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R3 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —S(O)p (optionally substituted alkyl), —SF5, optionally substituted heterocyclyl, optionally substituted 6- to 10-membered aryl, optionally substituted 5- to 10-membered heteroaryl, a spirocyclic heterocyclyl-carbocyclyl group, a spirocyclic heterocyclyl-heterocyclyl group, a spirocyclic carbocyclyl-carbocyclyl group, a spirocyclic carbocyclyl-heterocyclyl group or —NRaRb, wherein Ra and Rb are independently H or optionally substituted alkyl; or Ra and Rb may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R4 and R4′ are independently in each occurrence, hydrogen, halogen, cyano, nitro, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted cycloalkyl, optionally substituted cycloalkoxy, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, or optionally substituted di(alkyl)aminocarbonyl, optionally substituted alkylcarbonyloxy, optionally substituted alkylcarbonylamino, optionally substituted aryl, optionally substituted heteroaryl, —SF5, —SOp (optionally substituted alkyl or haloalkyl); or R4 together with R4′ together form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached; or —NRcRd, wherein Rc and Rd are independently H or optionally substituted alkyl; or Rc and Rd may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R8 is hydrogen, halogen, alkyl, haloalkyl, cycloalkyl, alkenyl or alkynyl;
R9 and R9′ are independently hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or cycloalkoxy, or R9 together with R9′ form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached;
Q is N or C—R8;
X is O, S or N—R′;
Y1 and Y6 are each independently N, C, or —CR4—;
Y2, Y3, Y4 and Y5 are each independently N, NR′, S, O, —CR4— or CR4R4′;
W is CR5R6, O, SOp, or N—R7,
Z is CR5R6, O, SOp, or N—R7,
wherein
R5 and R6 are independently in each occurrence hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or cycloalkoxy; or R5 together with R6 form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached;
R7 is hydrogen or C1-C4-alkyl; and
wherein at most three of Y1, Y2, Y3, Y4, Y5 and Y6 are heteroatoms;
a is 0 or 1;
q is 0 or 1;
p is independently in each occurrence is 0, 1, or 2; and
the dashed bonds (custom character) signifies a single or double bond;
or a pharmaceutically acceptable salt thereof.