US 11,708,360 B2
N-substituted-dioxocyclobutenylamino-3-hydroxy-picolinamides useful as CCR6 inhibitors
Brian Stephen Gerstenberger, Cambridge, MA (US); Andrew Christopher Flick, Carlsbad, CA (US); Daniel Wei-Shung Kung, Salem, CT (US); Vincent Michael Lombardo, Carmel, IN (US); James John Mousseau, Norwich, CT (US); Philippe Marcel Nuhant, Dorchester, MA (US); Ralph Pelton Robinson, Jr., Gales Ferry, CT (US); Daniel Copley Schmitt, Westerly, RI (US); Mark Edward Schnute, Acton, MA (US); Atli Thorarensen, Stow, MA (US); John Isidro Trujillo, Ledyard, CT (US); Rayomand Jal Unwalla, Bedford, MA (US); and Huixian Wu, East Lyme, CT (US)
Assigned to Pfizer Inc., New York, NY (US)
Filed by Pfizer Inc., New York, NY (US)
Filed on Mar. 5, 2021, as Appl. No. 17/192,968.
Application 17/192,968 is a continuation of application No. 16/576,997, filed on Sep. 20, 2019, granted, now 10,975,065.
Claims priority of provisional application 62/734,486, filed on Sep. 21, 2018.
Prior Publication US 2021/0206757 A1, Jul. 8, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 413/14 (2006.01); A61P 29/00 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 413/12 (2006.01); C07D 417/12 (2006.01); C07D 417/14 (2006.01); C07F 9/6558 (2006.01)
CPC C07D 413/14 (2013.01) [A61P 29/00 (2018.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 405/14 (2013.01); C07D 413/12 (2013.01); C07D 417/12 (2013.01); C07D 417/14 (2013.01); C07F 9/65583 (2013.01)] 16 Claims
OG exemplary drawing
 
1. A pharmaceutical composition comprising a compound of Formula (IA) or (IB)

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt or hydrate thereof, wherein
R1 is methyl;
R2 is methyl, ethyl, or isopropyl
or R1 and R2 taken together with the nitrogen atom to which they are attached form morpholine or 4-methylpiperazine;
R3 is H or —CH2OP(═O)(OH)2;
A is

OG Complex Work Unit Chemistry
R4 is methyl;
R5 is methyl, ethyl, methoxy, Cl, difluoromethoxy, cyano, or cyclopropyl;
R6 is H;
B is

OG Complex Work Unit Chemistry
R7 is methyl; and
n is 0,
and at least one pharmaceutically acceptable excipient, diluent, or carrier.