US 11,673,868 B2
Amino pyrimidine derivatives
Daniela Angst, Basel (CH); François Gessier, Altkirch (FR); and Anna Vulpetti, Basel (CH)
Assigned to Novartis AG, Basel (CH)
Filed by Novartis AG, Basel (CH)
Filed on Oct. 22, 2021, as Appl. No. 17/508,054.
Application 17/508,054 is a continuation of application No. 16/571,405, filed on Sep. 16, 2019, granted, now 11,180,460.
Application 16/571,405 is a continuation of application No. 15/974,190, filed on May 8, 2018, granted, now 10,457,647, issued on Oct. 29, 2019.
Application 15/974,190 is a continuation of application No. 15/135,296, filed on Apr. 21, 2016, abandoned.
Application 15/135,296 is a continuation of application No. 14/540,140, filed on Nov. 13, 2014, granted, now 9,512,084, issued on Dec. 6, 2016.
Claims priority of application No. 13195081 (EP), filed on Nov. 29, 2013.
Prior Publication US 2022/0041561 A1, Feb. 10, 2022
Int. Cl. C07D 405/12 (2006.01); C07D 403/12 (2006.01); A61K 31/505 (2006.01); A61K 31/506 (2006.01); C07D 239/47 (2006.01); C07D 401/14 (2006.01); C07D 401/10 (2006.01); C07D 401/12 (2006.01); A61P 29/00 (2006.01); A61P 35/02 (2006.01)
CPC C07D 239/47 (2013.01) [A61K 31/505 (2013.01); A61K 31/506 (2013.01); A61P 29/00 (2018.01); A61P 35/02 (2018.01); C07D 401/10 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 405/12 (2013.01)] 26 Claims
 
1. A method of preparing a compound of Formula (7) or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
comprising the step of reacting a compound of Formula (3) with a compound of Formula (4) to form a compound of Formula (5):

OG Complex Work Unit Chemistry
wherein,
PG is a protecting group;
R1 is hydrogen, C1-C6 alkyl optionally substituted by hydroxy;
R2 is hydrogen or halogen;
R3 is hydrogen or halogen;
R4 is hydrogen;
R5 is hydrogen or halogen;
or R4 and R5 are attached to each other and stand for a bond, —CH2—, —CH2—CH2—, —CH═CH—, —CH═CH—CH2—; —CH2—CH═CH—; or —CH2—CH2—CH2—;
R6 and R7 stand independently from each other for H, C1-C6 alkyl optionally substituted by hydroxyl, C3-C6 cycloalkyl optionally substituted by halogen or hydroxy, or halogen;
R8, R9, R, R′, R10 and R11 independently from each other stand for H, or C1-C6 alkyl optionally substituted by C1-C6 alkoxy; or any two of R8, R9, R, R′, R10 and R11 together with the carbon atom to which they are bound may form a 3-6 membered saturated carbocyclic ring;
R12 is hydrogen or C1-C6 alkyl optionally substituted by halogen or C1-C6 alkoxy;
or R12 and any one of R8, R9, R, R′, R10 or R 11 together with the atoms to which they are bound may form a 4, 5, 6 or 7 membered azaeyclic ring, which ring may optionally be substituted by halogen, cyano, hydroxyl, C1-C6 alkyl or C1-C6 alkoxy;
n is 0 or 1; and
R13 is C2-C6 alkenyl optionally substituted by C1-C6 alkyl, C1-C6 alkoxy or N,N-di-C1-C6 alkyl amino; C2-C6 alkynyl optionally substituted by C1-C6 alkyl or C1-C6 alkoxy; or C2-C6 alkylenyl oxide optionally substituted by C1-C6 alkyl.