US 11,807,628 B2
Benzodiazepine derivatives and uses thereof
Taekyo Park, Daejeon (KR); Sung Ho Woo, Sejong-Si (KR); Sunyoung Kim, Daejeon (KR); Suho Park, Daejeon (KR); Jongun Cho, Daejeon (KR); Doohwan Jung, Daejeon (KR); Donghoon Seo, Daejeon (KR); Jaeho Lee, Sejong-Si (KR); Sangkwang Lee, Daejeon (KR); Sanghyeon Yun, Daejeon (KR); Hyang Sook Lee, Daejeon (KR); Okku Park, Daejeon (KR); Beomseok Seo, Daejeon (KR); Sena Kim, Daejeon (KR); and Minah Seol, Daejeon (KR)
Assigned to IntoCell, Inc., Daejeon (KR)
Filed by IntoCell, Inc., Daejeon (KR)
Filed on Jun. 30, 2021, as Appl. No. 17/363,814.
Application 17/363,814 is a continuation of application No. 16/425,237, filed on May 29, 2019, granted, now 11,084,801.
Claims priority of provisional application 62/677,498, filed on May 29, 2018.
Prior Publication US 2022/0162190 A1, May 26, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 403/12 (2006.01); C07H 17/02 (2006.01); C07D 519/00 (2006.01)
CPC C07D 403/12 (2013.01) [C07D 519/00 (2013.01); C07H 17/02 (2013.01)] 20 Claims
 
1. A compound having the structure of Formula (II), (IIa), or (IIb)

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein:
A1 and A2 each independently represent a heterocyclic ring;
R1 and R2 are each independently an alkyl group;
Z1 is a linking group;
n1 and n2 are each independently an integer having a value of 1 to 5;
Z2 is a linking group;
L1, when present, is a linking group attached to the SO2 via a heteroatom selected from O, S, and N, and is selected such that cleavage of the bond between L1 and SO2 promotes cleavage of the bond between L1 and Z1, A1, or A2 to release the active agent;
X1 is —O—, —CRb2—, or —NRa—;
Ar is selected from aryl or heteroaryl;
Y1 is —(CRb2)yN(Ra)—, —(CRb2)yO—, or —(CRb2)yS—, positioned such that the N, O, or S atom is attached to TG if y is 1-10; wherein X1 and Y1 are positioned on adjacent atoms of Ar;
TG is a triggering group that, when activated, generates an N, O, or S atom capable of reacting with the SO2 to displace Z1, A1, or A2 and form a 5-6-membered ring including X1—SO2 and the intervening atoms of Ar;
w and x are each independently an integer having a value of 0 or 1;
each Ra is independently hydrogen or lower alkyl;
each Rb is independently hydrogen or lower alkyl; or
two Rb, together with the carbon atom to which they are attached, form a 3-5-membered ring; and
y is an integer having a value of 0-10.