US 12,168,664 B2
Triazolopyrimidines, their preparation and use
Konstantin Petrukhin, New Windsor, NY (US); Kirsten Alison Rinderspacher, Mount Vernon, NY (US); Shi-Xian Deng, White Plains, NY (US); Andras Varadi, New York, NY (US); Boglarka Racz, New York, NY (US); Peter Bernstein, Philadelphia, PA (US); Patricia C. Weber, Yardley, PA (US); Donald W. Landry, New York, NY (US); and Andrew S. Wasmuth, Brooklyn, NY (US)
Assigned to THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, New York, NY (US)
Filed by Konstantin Petrukhin, New Windsor, NY (US); Kirsten Alison Rinderspacher, Mount Vernon, NY (US); Shi-Xian Deng, White Plains, NY (US); Andras Varadi, New York, NY (US); Boglarka Racz, New York, NY (US); Peter Bernstein, Philadelphia, PA (US); Patricia C. Weber, Yardley, PA (US); Donald W. Landry, New York, NY (US); and Andrew S. Wasmuth, Brooklyn, NY (US)
Filed on Oct. 30, 2020, as Appl. No. 17/085,791.
Application 17/085,791 is a continuation of application No. PCT/US2019/030172, filed on May 1, 2019.
Claims priority of provisional application 62/665,047, filed on May 1, 2018.
Prior Publication US 2021/0047337 A1, Feb. 18, 2021
Int. Cl. C07D 487/04 (2006.01); A61P 27/02 (2006.01); C07D 519/00 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 27/02 (2018.01); C07D 519/00 (2013.01)] 20 Claims
 
1. A compound having the structure:

OG Complex Work Unit Chemistry
wherein
R1, R2, R3, R4, and R5 are each independently H, halogen, alkyl, haloalkyl, O-haloalkyl, aryl or heteroaryl;
X is N or CR6,
wherein Re is H, OH, or halogen;
A is absent or present, and when present is

OG Complex Work Unit Chemistry
B has the structure:

OG Complex Work Unit Chemistry
wherein
α and β are each a bond that is present or absent;
X1 is N, NH or NR10,
wherein R10 is alkyl, alkenyl or alkynyl;
X2 is C or N;
X3 is CH or N;
R7, R8 and R9 are each, independently, H, halogen, alkyl, alkenyl, alkynyl, alkyl-OH, alkyl-NH2, alkyl-OAc alkyl-O(CO)-alkyl, alkyl-O-alkyl, haloalkyl, cycloalkyl, O-alkyl, NH-alkyl, C(O)OH, C(O)—NH2, C(O)—N(CH3)2, C(O)—NHCH3, NHC(O)—N(CH3)2, CN or CF3,
wherein
X1, X2 and X3 are each N, α is present and β is absent; or
X1 is NH, X2 is C, X3 is CH, α is absent and β is present; or
X1 is N, X2 is N, X3 is CH, α is present and β is absent; or
X1 is NH or NR10, X2 is C, X3 is N, α is absent and β is present, wherein when X1 is NH, X2 is C, X3 is N, α is absent and β is present, then one of R7, R8 and R9 is other than H,
or B has the structure:

OG Complex Work Unit Chemistry
wherein
X4 and X5 are each, independently, is N or CH; and
R11, R12 and R13 are each, independently, H, halogen, alkyl, alkenyl, alkynyl, alkyl-OH, alkyl-NH2, alkyl-OAc, alkyl-O(CO)-alkyl, alkyl-O-alkyl, haloalkyl, cycloalkyl, O-alkyl, NH-alkyl, C(O)OH, C(O)—NH2, C(O)—N(CH3)2, C(O)—NHCH3, NHC(O)—N(CH3)2, CN or CF3,
or a pharmaceutically acceptable salt thereof.