US 12,215,128 B2
(Pyridinylmethyl)butanediamine derivatives that chelate copper
Nicholas Tonks, Cold Spring Harbor, NY (US); Navasona Krishnan, Hawthorn Woods, IL (US); and Andreas Grill, Saint James, NY (US)
Assigned to Cold Spring Harbor Laboratory, Cold Spring Harbor, NY (US); and Depymed, Inc., Farmingdale, NY (US)
Appl. No. 17/261,313
Filed by COLD SPRING HARBOR LABORATORY, Cold Spring Harbor, NY (US); and DEPYMED, INC., Farmingdale, NY (US)
PCT Filed Jul. 19, 2019, PCT No. PCT/US2019/042580
§ 371(c)(1), (2) Date Jan. 19, 2021,
PCT Pub. No. WO2020/018893, PCT Pub. Date Jan. 23, 2020.
Claims priority of provisional application 62/700,968, filed on Jul. 20, 2018.
Claims priority of provisional application 62/855,031, filed on May 31, 2019.
Prior Publication US 2021/0261602 A1, Aug. 26, 2021
Int. Cl. C07D 213/38 (2006.01); C07D 401/12 (2006.01); C07J 43/00 (2006.01)
CPC C07J 43/003 (2013.01) [C07D 213/38 (2013.01); C07D 401/12 (2013.01)] 19 Claims
 
1. A compound of formula:

OG Complex Work Unit Chemistry
wherein R1, R2, R3 and R4 are chosen independently from hydrogen, (C1-C6)alkyl, (C1-C6)oxaalkyl, and (C1-C6)aminoalkyl, or two adjacent R1, R2, R3 and R4 may form a five-, six-, or seven-membered ring, said five-, six-, or seven-membered ring optionally substituted with one or two substituents chosen from halogen, cyano, hydroxy, (C1-C6)alkyl, (C1-C6)oxaalkyl, and (C1-C6)aminoalkyl;
A is a polycyclic ring system chosen from one of the following ring systems:

OG Complex Work Unit Chemistry
said rings optionally substituted with one or more substituents chosen from halogen, hydroxy, (C1-C6)alkyl, oxo, (C1-C6)oxaalkyl, carboxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, carboxy(C1-C6)alkyl, amino, and (C1-C6)aminoalkyl;
n is zero or one; and
p is one or two;
with the proviso that, when R1, R2, R3, and R4 are all hydrogen, p is one, and n is zero, the polycyclic ring system A is not a perhydrocyclopenta[a]phenanthrene of formula

OG Complex Work Unit Chemistry
 attached at the 3-position as shown, in which a substituent at 17 is —CH(CH3)CH2CH2COOH, —CH(CH3)CH2CH2COOCH3, —CH(CH3)CH2CH2CH(OSO3H)CH(CH3)2,

OG Complex Work Unit Chemistry
 regardless of the remaining substitutions of the ring.