US 12,269,822 B2
Anthelminthic heterocyclic compounds
Alan Long, Flowery Branch, GA (US); Hyoung Lee, Alpharetta, GA (US); and Hannes Fiepko Koolman, Biberach an der Riss (DE)
Appl. No. 17/142,877
Filed by BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC., Duluth, GA (US); and BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG, Ingelheim am Rhein (DE)
PCT Filed Jul. 3, 2019, PCT No. PCT/US2019/040509
§ 371(c)(1), (2) Date Jan. 6, 2021,
PCT Pub. No. WO2020/014068, PCT Pub. Date Jan. 16, 2020.
Claims priority of provisional application 62/695,656, filed on Jul. 9, 2018.
Prior Publication US 2022/0048903 A1, Feb. 17, 2022
Int. Cl. C07D 471/04 (2006.01); A61P 33/10 (2006.01)
CPC C07D 471/04 (2013.01) [A61P 33/10 (2018.01)] 17 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
wherein:
W1 W2, W3 and W4 are independently C—H or N;
R1 is cyano, optionally substituted alkoxy, optionally substituted haloalkoxy, optionally substituted aryloxy, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted C3-C8-cycloalkyl, optionally substituted alkenyl, optionally substituted haloalkenyl, optionally substituted alkynyl, optionally substituted haloalkynyl, optionally substituted aryl; optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted alkyl-SOn, haloalkyl-SOn, amino, NH-optionally substituted alkyl, or NRaRb wherein Ra and Rb are independently optionally substituted C1-C4 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 be optionally substituted;
R2 is halogen, cyano, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkyl, optionally substituted C3-C8-cycloalkyl, or SOm(optionally substituted alkyl);
R3 is selected from the group consisting of 6- or 10-membered aryl and 5- to 10-membered heteroaryl, each of which may be optionally substituted with 1, 2, 3, 4 or 5 substituents;
each R4 is independently hydrogen, halogen, cyano, nitro, —OH, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted cycloalkyl, -amino, NH-optionally substituted alkyl, SF5, or NRcRd wherein Rc and Rd are independently 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 be optionally substituted, SOp(optionally substituted C1-C4-alkyl);
o is 0, 1, 2, 3, or 4;
m, n, and p are independently 0, 1, or 2;
q is 0 or 1;
X and Y are independently CR5R6, O, S, or N—R7, wherein at least one of X and Y is CR5R6;
R5 and R6 are independently hydrogen, fluorine or C1-C4-alkyl;
R7 is hydrogen or C1-C4-alkyl; or
a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof.