US 12,215,096 B2
Matrix metalloproteinase (MMP) inhibitors and methods of use thereof
Wenjin Yang, Newark, DE (US); Kai-Wei Chang, Newark, DE (US); Suying Liu, Newark, DE (US); and Cheng-Han Tsai, Newark, DE (US)
Assigned to Foresee Pharmaceuticals USA, Inc., Newark, DE (US)
Filed by Foresee Pharmaceuticals USA, Inc., Newark, DE (US)
Filed on Jul. 6, 2023, as Appl. No. 18/347,674.
Application 18/347,674 is a continuation of application No. 17/055,459, granted, now 11,739,080, previously published as PCT/US2019/032127, filed on May 14, 2019.
Claims priority of provisional application 62/671,753, filed on May 15, 2018.
Prior Publication US 2024/0018131 A1, Jan. 18, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 407/14 (2006.01); C07D 233/74 (2006.01); C07D 401/04 (2006.01); C07D 401/14 (2006.01); C07D 403/04 (2006.01); C07D 405/04 (2006.01); C07D 407/04 (2006.01); C07D 409/04 (2006.01); C07D 409/14 (2006.01); C07D 413/04 (2006.01); C07D 413/14 (2006.01)
CPC C07D 407/14 (2013.01) [C07D 233/74 (2013.01); C07D 401/04 (2013.01); C07D 401/14 (2013.01); C07D 403/04 (2013.01); C07D 405/04 (2013.01); C07D 407/04 (2013.01); C07D 409/04 (2013.01); C07D 409/14 (2013.01); C07D 413/04 (2013.01); C07D 413/14 (2013.01)] 15 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a tautomer, stereoisomer, pharmaceutically acceptable salt, or solvate thereof,
wherein:
ring B is an optionally substituted phenyl, pyridinyl, pyridinyl N-oxide, imidazolyl, or pyrazolyl;
ring C is phenyl;
ring D is phenyl or pyridinyl;
X is S;
Y is O, and Z is CH2;
R1 is hydrogen or alkyl;
each R2 is independently selected from the group consisting of hydrogen, alkyl, halo, hydroxyl, haloalkyl, alkoxy, alkylthio, amino, amide, alkylamine, aminoalkyl, cyano, hydroxyalkyl, —(CH2)pC(O)OR6, and —(CH2)pOC(O)R6;
each R3 is independently selected from the group consisting of hydrogen, alkyl and halo;
R4 is hydrogen or alkyl;
R5 is hydrogen;
each R6 is independently selected from the group consisting of hydrogen and alkyl, wherein the alkyl is unsubstituted or substituted with one or more groups independently selected from the group consisting of amino, hydroxyl, halo, and alkoxy;
m is 1, 2, 3, or 4;
n is 1, 2, 3, 4, or 5; and
p is 0, 1, 2, 3, 4, or 5.