US 12,258,331 B2
Pyrimidine derivative and preparation process and use thereof
Xingshu Li, Guangdong (CN); Xinzi Chen, Guangdong (CN); Wei Yang, Guangdong (CN); and Jianmin Guo, Guangdong (CN)
Assigned to Guangdong Lewwin Pharmaceutical Research Institute Co., Ltd., Guangdong (CN); and Guangdong CS-Lewwin Drug Research Co., Ltd., Guangdong (CN)
Filed by Guangdong Lewwin Pharmaceutical Research Institute Co., Ltd., Guangdong (CN); and Guangdong CS-Lewwin Drug Research Co., Ltd., Guangdong (CN)
Filed on Jul. 19, 2023, as Appl. No. 18/223,652.
Application 18/223,652 is a division of application No. 17/255,719, previously published as PCT/CN2019/105043, filed on Sep. 10, 2019.
Claims priority of application No. 201811059596.7 (CN), filed on Sep. 12, 2018; and application No. 201811623543.3 (CN), filed on Dec. 28, 2018.
Prior Publication US 2023/0365532 A1, Nov. 16, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 403/10 (2006.01); A61P 35/00 (2006.01); C07B 59/00 (2006.01); C07D 239/30 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 403/14 (2006.01)
CPC C07D 403/10 (2013.01) [A61P 35/00 (2018.01); C07B 59/002 (2013.01); C07D 239/30 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/14 (2013.01); C07B 2200/05 (2013.01)] 3 Claims
 
1. A method of treating a tumor comprising administering to a patient in need thereof a pharmaceutically effective amount of a pyrimidine derivative of Formula 2:

OG Complex Work Unit Chemistry
wherein
X1 and X2 indicate, independently of one another, CH or N;
Y is a hydrogen atom or a deuterium atom;
R1 is CD3, C2-C4 alkyl, C2-C4 alkenyl, or C2-C4 alkynyl, in which one or more hydrogen atoms in the alkyl, alkenyl or alkynyl is unsubstituted or substituted with a deuterium atom;
Z is an oxygen atom, a sulfur atom, a selenium atom, NH, NCH3 or sulfoxide SO;
R2 is 2-(N,N-dialkylamino)ethyl, or 4-piperidyl with the nitrogen atom attached to C1-C4 alkyl, or 4-piperidyl with positions 2 and 3 substituted with an alkyl, or 4-piperidyl with a bridge ring;
R3-R8 are each, independently of one another, a hydrogen atom, a halogen, C1-C4 alkyl, C2-C4 alkenyl, or C2-C4 alkynyl;
the carbon atom attached to R1 and Y is a chiral carbon in R-configuration;
Y and R1 are not both deuterium atoms; and
at least one of Y and R1 contains a deuterium atom.