US 12,187,759 B2
TLR7 agonists
Stephen E. Webber, Carlsbad, CA (US); and James Richard Appleman, Carlsbad, CA (US)
Assigned to Primmune Therapeutics, Inc., Carlsbad, CA (US)
Filed by Primmune Therapeutics, Inc., Carlsbad, CA (US)
Filed on Jun. 30, 2023, as Appl. No. 18/345,903.
Application 18/345,903 is a continuation of application No. 17/104,808, filed on Nov. 25, 2020, granted, now 11,692,005.
Claims priority of provisional application 62/940,622, filed on Nov. 26, 2019.
Prior Publication US 2024/0116974 A1, Apr. 11, 2024
Int. Cl. C07H 19/16 (2006.01); A61K 31/708 (2006.01); A61K 45/06 (2006.01)
CPC C07H 19/16 (2013.01) [A61K 31/708 (2013.01); A61K 45/06 (2013.01)] 14 Claims
 
1. A method for treating a precancerous condition in a subject caused by a papillomavirus infection comprising administering an effective amount of a compound of Formula I:

OG Complex Work Unit Chemistry
wherein
R1 is independently —H, —OH, —O—C(O)—R8 or —F;
R2 is independently —H, —OH, —O—C(O)—R8 or —F;
R3 is —OH, or —O—C(O)—R8;
R4 is —H, —OH, —O—C(O)—R8 or —(C1-C8)alkyl;
wherein R3 and R4 can be in the form of a carbonyl oxygen (═O);
R5 is —H, —OH, —O—C(O)—R8, —(C1-C8)alkyl, —O—(C1-C8)alkyl, —NH2 or —NHR8
wherein R4 and R5 can form a 3-6 membered cycloalkyl ring;
R6 is —H, —(C1-C8)alkyl, —C(H)═CH2, —C(H)═CH(C1-C8)alkyl), —C(H)═C(C1-C8)alkyl)(C1-C8)alkyl), —C(H)═C═CH2, —C(H)═C═C(C1-C8)alkyl)H, —CH2C═CH, —OH or —O(C1-C8)alkyl;
R7 is —H, —OH, —OCH3, —SH or —Cl;
R8 is independently —(C1-C8)alkyl, aryl, —(CH2)n(aryl), heteroaryl or —(CH2)n(heteroaryl);
n is an integer 1, 2, 3, 4 or 5;
wherein at least one R4 or R5 is not —H;
wherein each alkyl, cycloalkyl, aryl and heteroaryl are independently optionally substituted by one or more of CN, NO2, halogen, (C1-C3)alkyl, (C1-C3)haloalkyl, (C1-C3)cycloalkyl, aryl, heteroaryl, OH, alkenyl, alkynyl, O—(C1-C3)alkyl, O—C(O)—R9, O-(alkylene)aryl, O-(alkylene)heteroaryl, C(O)R9, S(C1-C8)alkyl, S(O)(C1-C8)alkyl, SO2(C1-C8)alkyl, C(O)OR9, C(O)NR9R9, C(O)NR9SO2(C1-C8)alkyl, NR9R9, NR9(CO)OR9, NH(CO)R9, NH(SO2)(C1-C8)alkyl or NH(SO2)NR9R9, and R9 is independently —H, —OH, —(C1-C8)alkyl, cycloalkyl, heterocyclyl; or the two R9's of C(O)NR9R9 or NR9R9 combine together with the nitrogen atom to form a heterocycle;
or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof.