US 11,932,645 B2
Substituted pyrazolo[1,5-a]pyrimidines and their use in the treatment of medical disorders
Renato T. Skerlj, West Newton, MA (US); Peter T. Lansbury, Brookline, MA (US); Andrew C. Good, Wallingford, CT (US); and Elyse Marie Josee Bourque, L'etang-du-Nord (CA)
Assigned to Bial—R & D Investments, S.A., Coronado (PT)
Filed by Bial—R&D Investments, S.A., Coronado (PT)
Filed on Jul. 7, 2021, as Appl. No. 17/369,507.
Application 17/369,507 is a continuation of application No. 16/733,598, filed on Jan. 3, 2020, granted, now 11,091,492.
Application 16/733,598 is a continuation of application No. 15/523,769, granted, now 10,570,135, issued on Feb. 25, 2020, previously published as PCT/US2015/059541, filed on Nov. 6, 2015.
Claims priority of provisional application 62/076,062, filed on Nov. 6, 2014.
Prior Publication US 2022/0169652 A1, Jun. 2, 2022
Int. Cl. C07D 487/04 (2006.01); A61K 31/4162 (2006.01); A61K 31/519 (2006.01); A61P 3/10 (2006.01); A61P 13/12 (2006.01); A61P 25/08 (2006.01); A61P 25/16 (2006.01); A61P 25/18 (2006.01); A61P 25/22 (2006.01); A61P 25/24 (2006.01); A61P 25/28 (2006.01); A61P 27/06 (2006.01); A61P 35/00 (2006.01); A61P 43/00 (2006.01); C07D 519/00 (2006.01)
CPC C07D 487/04 (2013.01) 20 Claims
 
1. A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a compound of Formula III:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
R1 and R2 each represent independently for each occurrence hydrogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxyl, —(C1-4 alkylene)-(2-6 membered heteroalkyl), cyclopropyl, cyano, chloro, or fluoro;
R3 represents independently for each occurrence hydrogen or C1-4 alkyl;
X1 is one of the following:
(a) a carbonyl-containing linker selected from —C(O)N(H)-ψ and —C(O)N(H)(C1-6 alkylene)-ψ; where ψ is a bond to A1; or
(b) an amine-containing linker selected from —(C1-4 alkylene)-N(H)-ψ and —(C1-4 alkylene)-N(H)—(C1-4 alkylene)-ψ;
A1 is phenyl substituted by (a) 0, 1, 2, or 3 occurrences of Y2 and (b) one of the following:
(i) a 5-membered heteroaryl substituted by 0, 1, 2, or 3 occurrences of Y2; or
(ii) —(C1-6 alkylene)-CO2R3;
Y2 represents, independently for each occurrence, C1-6 alkyl, C3-6 cycloalkyl, halogen, C1-6 haloalkyl, C1-6 hydroxyalkyl, hydroxyl, C1-6 alkoxyl, cyano, azido, —N(R3)2, —(C1-6 alkylene)-(5-6 membered heterocyclyl), —(C1-6 alkylene)-CO2R3, or C1-6 haloalkyl-substituted C3-6 cycloalkyl; and
n is 1, 2, or 3.