US 12,168,665 B2
Substituted imidazo[l,2-a]pyrazines and pyrazino[l,2-a] pyrimidines as topical agents for dermatological applications
Fuqiang Ruan, Bellevue, WA (US)
Assigned to Genesis Molecular Technologies, Inc., Austin, TX (US)
Filed by Genesis Molecular Technologies, Inc., Austin, TX (US)
Filed on Apr. 27, 2023, as Appl. No. 18/140,402.
Application 18/140,402 is a continuation of application No. 17/492,514, filed on Oct. 1, 2021, granted, now 11,639,356.
Claims priority of provisional application 63/087,670, filed on Oct. 5, 2020.
Prior Publication US 2023/0374020 A1, Nov. 23, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/4985 (2006.01); A61K 8/49 (2006.01); A61Q 19/00 (2006.01); C07D 487/04 (2006.01)
CPC C07D 487/04 (2013.01) [A61K 8/4953 (2013.01); A61Q 19/00 (2013.01)] 15 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a cosmeceutically acceptable or pharmaceutically acceptable salt thereof,
wherein:
L is —C(O)— or —S(O)2—;
X is —C(O)— or —CH2C(O)—;
Y is H or C(O)R;
R is C1-30 alkyl or C2-30 alkenyl;
R1 is H or CH3;
R2 is H or CH3;
R3 is H or D;
Q is benzyl, phenyl, or an 8- to 11-membered aryl;
wherein the 8- to 11-membered aryl is bicyclic;
wherein the 8- to 11-membered aryl optionally contains 1, 2, or 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
wherein the benzyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-4 perfluoroalkyl, C(NH)NH2, C(O)OH, NH2, NHC1-4 alkyl, N(C1-4 alkyl)2, NHC(NH)NH2, OH, OC1-3 alkyl, S(O)2alkyl, S(O)2heterocyclyl, and S(O)2aryl; and
wherein the phenyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-4 alkyl, C1-4 perfluoroalkyl, C(NH)NH2, C(O)OH, NH2, NHC1-4 alkyl, N(C1-4 alkyl)2, NHC(NH)NH2, OH, OC1-3 alkyl, S(O)2alkyl, S(O)2heterocyclyl, and S(O)2aryl; and
n is 1 or 2.
 
3. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of claim 1, or a pharmaceutically acceptable salt thereof.