US 12,486,241 B2
Cystine diamide analogs for cystinuria
Longqin Hu, Belle Mead, NJ (US); and Haifa Albanyan, Riyadh (SA)
Assigned to RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY, New Brunswick, NJ (US)
Appl. No. 17/757,244
Filed by Rutgers, The State University of New Jersey, New Brunswick, NJ (US)
PCT Filed Dec. 11, 2020, PCT No. PCT/US2020/064583
§ 371(c)(1), (2) Date Jun. 13, 2022,
PCT Pub. No. WO2021/119475, PCT Pub. Date Jun. 17, 2021.
Claims priority of provisional application 62/947,799, filed on Dec. 13, 2019.
Prior Publication US 2023/0043330 A1, Feb. 9, 2023
Int. Cl. C07D 295/185 (2006.01); C07C 323/41 (2006.01); C07D 211/58 (2006.01); C07D 241/04 (2006.01); C07D 295/13 (2006.01); C07D 471/10 (2006.01)
CPC C07D 295/185 (2013.01) [C07C 323/41 (2013.01); C07D 211/58 (2013.01); C07D 241/04 (2013.01); C07D 295/13 (2013.01); C07D 471/10 (2013.01)] 20 Claims
 
1. A compound, a pharmaceutically acceptable salt thereof, a solvate thereof, or a prodrug thereof, wherein the compound is represented by Formula I,

OG Complex Work Unit Chemistry
Wherein each pair of R1 and R2 are independently defined as follows:
a) R1 is H, R2 is (CH2)mNRaRb, m is 2, 3 or 4; wherein Ra and Rb are each independently a C1-8alkyl, alternatively Ra and Rb together with the N they are attached to, link up to form a 4 to 8-membered heterocyclic ring, wherein a carbon in the 4 to 8-membered heterocyclic ring is optionally replaced with a heteroatom selected from the group consisting of O, S, NH, and N C1-8alkyl;
or
b) R1 and R2, together with the amide nitrogen link up to form a ring of formula X-1

OG Complex Work Unit Chemistry
wherein
R3 is C1-8alkyl; r is 0, 1, or 2;
n, p, and A are defined as follows:
i)
n and p are independently 2 or 3;
A is NRe, wherein Re is H, C2-8alkyl or a C3-8 cycloalkyl;
ii)
n is 0, 1, or 2; p is 2 or 3 or 4;
A is a structure of Formula Y-1

OG Complex Work Unit Chemistry
wherein Rd is H or C1-8alkyl;
s is 0, 1, or 2; t is 2, 3 or 4; provided that when n is 0, s is 1 or 2;
or
iii)
n and p are independently 1, 2, 3 or 4;
A is CH(CH2)qNReRf, wherein
Re and Rf are independently C1-8alkyl; q is 0-3;
alternatively, Re and Rf, together with the N they are attached to, link up to form a 4 to 8-membered heterocyclic ring;
provided that the compound is not

OG Complex Work Unit Chemistry