US 11,771,738 B2
Endoparasitic depsipeptides
Todd Maddux, Kalamazoo, MI (US); Matthew W. Bedore, Portage, MI (US); Paul D. Johnson, Kalamazoo, MI (US); Tomasz Respondek, Kalamazoo, MI (US); Susan M. K. Sheehan, Galesburg, MI (US); Graham M. Kyne, Portage, MI (US); Richard A. Ewin, Kalamazoo, MI (US); Rajendran Vairagoundar, Kalamazoo, MI (US); and Michael P. Curtis, Portage, MI (US)
Assigned to Zoetis Services LLC, Parsippany, NJ (US)
Appl. No. 17/52,571
Filed by Zoetis Services LLC, Parsippany, NJ (US)
PCT Filed May 7, 2019, PCT No. PCT/US2019/031158
§ 371(c)(1), (2) Date Nov. 3, 2020,
PCT Pub. No. WO2019/217449, PCT Pub. Date Nov. 14, 2019.
Claims priority of provisional application 62/669,623, filed on May 10, 2018.
Prior Publication US 2022/0323540 A1, Oct. 13, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 38/15 (2006.01); A61P 33/00 (2006.01); C07D 273/00 (2006.01); C07D 413/10 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01)
CPC A61K 38/15 (2013.01) [A61P 33/00 (2018.01); C07D 273/00 (2013.01); C07D 413/10 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01)] 13 Claims
 
1. A compound of Formula (3A)

OG Complex Work Unit Chemistry
wherein Ring A and Ring B are the same and are selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, oxetanyl, azetidinyl, piperidinyl, pyrrolidinyl, morpholinyl, tetrahydropyranyl, tetrahydropyrimidinyl, tetrahydropyridinyl, tetrahydropyranyl, thiophenyl, furanyl, thiazolyl, oxazolyl, pyrrolyl, pyrazolyl, imidazolyl, pyridinyl, thiadiazolyl, isothiazolyl, triazinyl, pyrimidinyl, pyrazinyl, pyridazinyl, isoxazolyl, tetrazolyl, oxadiazolyl, 1,2-dihydropyridinyl, triazolyl, quinolinyl, isoquinolinyl, benzofuranyl, 2,3-dihydrothieno[3,4-b][1,4]dioxine, 3,4-dihydro-2H-pyrano[2,3-b]pyridinyl, oxazolo[5,4-b]pyridinyl, pyrazolo[1,5-a]pyridinyl, pyrazolo[1,5-a]pyrimidine, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, 4,5-tetrahydropyrazolo[1,5-a]pyrimidine, 1H-pyrrolo[3,2-b]pyridinyl, indazolyl, furo[2,3-b]pyridinyl, and benzo[d][1,3]dioxole; each (R)n is the same and each R in (R)n is independently selected from the group consisting of C1-C6alkyl optionally substituted with at least one substituent selected from hydroxyl, C3-C6cycloalkyl and —ORa; halo, oxo, cyano, hydroxyl, —OR5, —NRaRb, C1-C4haloalkyl, C1-C4haloalkoxy, —S(O)pRa, C1-C6alkoxy, C3-C6cycloalkyl, —C(O)NRaRb, —C(O)Ra, —C(O)ORa, —NRaC(O)Rb, pyrazolyl, imidazolyl, pyridinyl, pyrimidinyl, piperidinyl, morpholinyl, pyrrolidinyl, dihydropyrimidinyl; and phenyl optionally substituted with at least one substituent selected from C1-C3alkyl, —CF3, halo, and hydroxyl; n is 0, 1, 2, or 3;
Ra and Rb are each independently selected from H or C1-C6alkyl;
Rc and Rd are each independently selected from the group consisting of H, hydroxyl, —CF3, F, methyl, ethyl, methoxy, ethoxy and —N(CH2CH3)2; and wherein each Rc is the same and each Rd is the same;
R5 is C3-C6cycloalkyl or C1-C3alkylC3-C6cycloalkyl; and
p is 0, 1, or 2;
stereoisomers thereof, and veterinary acceptable salts thereof.