US 12,187,668 B2
Compositions and methods for treating and preventing neurodegenerative disorders
Petr Kocis, Framingham, MA (US); Martin Tolar, Framingham, MA (US); and John Hey, Framingham, MA (US)
Assigned to Alzheon, Inc., Framingham, MA (US)
Filed by Alzheon, Inc., Framingham, MA (US)
Filed on Feb. 16, 2022, as Appl. No. 17/673,269.
Application 17/673,269 is a continuation of application No. 17/328,199, filed on May 24, 2021, abandoned.
Application 17/328,199 is a continuation of application No. 16/807,747, filed on Mar. 3, 2020, granted, now 11,053,192, issued on Jul. 6, 2021.
Application 16/807,747 is a continuation of application No. 15/751,547, granted, now 10,590,070, issued on Mar. 17, 2020, previously published as PCT/US2016/046336, filed on Aug. 10, 2016.
Claims priority of provisional application 62/203,256, filed on Aug. 10, 2015.
Prior Publication US 2023/0133465 A1, May 4, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 309/26 (2006.01); A61P 25/28 (2006.01); C07C 309/19 (2006.01); C07C 309/27 (2006.01); C07C 317/50 (2006.01); C07C 323/59 (2006.01); C07C 323/60 (2006.01); C07D 207/14 (2006.01); C07D 207/16 (2006.01); C07D 209/20 (2006.01); C07D 211/58 (2006.01); C07D 233/26 (2006.01); C07D 295/185 (2006.01); C07D 401/06 (2006.01); C07D 401/12 (2006.01); C07D 403/06 (2006.01); C07D 403/12 (2006.01); C07K 5/00 (2006.01); C07K 5/078 (2006.01)
CPC C07C 309/26 (2013.01) [A61P 25/28 (2018.01); C07C 309/19 (2013.01); C07C 309/27 (2013.01); C07C 317/50 (2013.01); C07C 323/59 (2013.01); C07C 323/60 (2013.01); C07D 207/14 (2013.01); C07D 207/16 (2013.01); C07D 209/20 (2013.01); C07D 211/58 (2013.01); C07D 233/26 (2013.01); C07D 295/185 (2013.01); C07D 401/06 (2013.01); C07D 401/12 (2013.01); C07D 403/06 (2013.01); C07D 403/12 (2013.01); C07K 5/00 (2013.01); C07K 5/06165 (2013.01); C07B 2200/07 (2013.01); C07C 2601/08 (2017.05); C07C 2601/14 (2017.05)] 7 Claims
 
1. A compound having the structural formula (IV-1):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
Rb1 is selected from hydrogen, —(CH2)1-3—C(O) OH, —(CH2)1-3—C(O)O(C1-C3 alkyl), —C(O)—[CH(RA)]1-2—NH—RB, and —C(O)—[CH(RA)]1-2—NH—C(O)—[CH(RA)]1-2—NH—RB;
each R7 and each R8 is independently selected from —H, —NH2, —NRaRb—C(O)NH2, —C(O)NRaRb, —(C(Rx)(Ry))nNH2, —(C(Rx)(Ry))n NRaRb, —(C(Ra)(Rb))nC(O)NH2, —(C(Ra)(Rb))nC(O)NRaRb, —OH, —(C(Ra)(Rb))nOH, —CO2H, —(C(Ra)(Rb))nCO2H, —SO3H, —(C(Ra)(Rb))nSO3H, deuterium, halogen, alkyl, alkoxy, alkenyl, alkynyl, cyano, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;
each Ra is hydrogen or optionally substituted alkyl;
each Rb is selected from hydrogen, alkyl substituted with a carboxyl or a carboxylate, and an amino acid or a dipeptide, wherein the amino acid or the dipeptide is bound to the nitrogen atom in R3 through a carboxy group; or Ra and Rb are taken together to form an optionally substituted heterocyclyl;
each Rx and Ry are independently a hydrogen or a C1-C6 alkyl group
n is 1 or 2;
each RA is independently selected from hydrogen or a side group of a natural or unnatural amino acid; and
RB is selected from hydrogen and a protecting group.