US 12,295,936 B2
Immunomodulating urea azalides
Mark R. Cox, Kalamazoo, MI (US); Timothy L. Stuk, Mattawan, MI (US); Todd M. Maddux, Kalamazoo, MI (US); Richard Andrew Ewin, Kalamazoo, MI (US); Paul D. Johnson, Kalamazoo, MI (US); Tomasz Respondek, Kalamazoo, MI (US); Graham M. Kyne, Kalamazoo, MI (US); and Rajendran Vairagoundar, Kalamazoo, MI (US)
Assigned to Zoetis Services LLC, Parsippany, NJ (US)
Filed by Zoetis Services LLC, Parsippany, NJ (US)
Filed on Aug. 17, 2023, as Appl. No. 18/451,243.
Application 18/451,243 is a division of application No. 17/198,863, filed on Mar. 11, 2021, granted, now 11,771,677.
Claims priority of provisional application 62/988,492, filed on Mar. 12, 2020.
Prior Publication US 2023/0390237 A1, Dec. 7, 2023
Int. Cl. C07D 498/04 (2006.01); A61K 31/351 (2006.01); A61K 31/7048 (2006.01); A61P 11/00 (2006.01); A61P 29/00 (2006.01); A61P 31/04 (2006.01); A61P 37/02 (2006.01); C07D 519/00 (2006.01); C07H 17/08 (2006.01)
CPC A61K 31/351 (2013.01) [A61P 11/00 (2018.01); A61P 29/00 (2018.01); A61P 31/04 (2018.01); A61P 37/02 (2018.01); C07D 498/04 (2013.01); C07D 519/00 (2013.01); C07H 17/08 (2013.01)] 6 Claims
 
1. A compound of Formula (1-A1)

OG Complex Work Unit Chemistry
wherein
R0 is H, methyl, ethyl or propyl;
R1 is methyl, ethyl, propyl, or isopropyl; or R1 is benzyl, —CH2pyridine, —CH2pyrimidine, —CH2pyrazole or —CH2imidazole, wherein each is optionally substituted with at least one R9 substituent;
R2 and R3 are each independently H, C1-C6alkyl; —CH2N(CH3)2, or —CH2CH2N(CH3)2; or
cyclopropyl, C1alkylcyclopropyl, cyclobutyl, C1alkylcyclobutyl, cyclopentyl,
C1alkylcyclopentyl, cyclohexyl, C1alkylcyclohexyl, phenyl, C1alkylphenyl, piperidinyl, C1alkylpiperidinyl, C2alkylpiperidinyl, piperazinyl, morpholinyl, tetrahydro-2H-pyran, pyrrolyl, pyrazolyl, triazolyl, pyridinyl, pyrimidinyl, pyridazinyl or pyrazinyl, each of which is optionally substituted with at least one R9 substituent;
or R2 and R3 taken together with the nitrogen atom to which they are attached form Ring A which is azetidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyrrolidinyl, indolyl, piperidinyl, piperazinyl, morpholinyl, or thiomorpholinyl, each optionally substituted with at least one R10 substituent selected from methyl, ethyl, F, Cl, —CF3 and oxo;
or Ring A is indolinyl, isoindolinyl, tetrahydroquinolinyl, dihydrobenzooxazinyl, or dihydrobenzothiazinyl optionally substituted with at least one oxo;
R5 and R6 taken together with the nitrogen atom to which they are attached form Ring B which is azetidinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl or thiomorpholinyl, and wherein each is optionally substituted with at least one R9 substituent; and wherein each ring is further optionally fused with Y which is phenyl, pyridinyl or pyrimidinyl; and
R9 is independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, cyclopropyl, methoxy, F, Cl, Br, cyano, —N(CH3)2, hydroxy, —CHF2, —CF3, —OCHF2, —OCF3 and oxo; or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof.