US 12,258,335 B1
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)
Appl. No. 17/055,483
Filed by Foresee Pharmaceuticals USA, Inc., Newark, DE (US)
PCT Filed May 14, 2019, PCT No. PCT/US2019/032131
§ 371(c)(1), (2) Date Nov. 13, 2020,
PCT Pub. No. WO2019/222157, PCT Pub. Date Nov. 21, 2019.
Claims priority of provisional application 62/671,753, filed on May 15, 2018.
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 405/14 (2006.01); A61P 11/00 (2006.01); A61P 13/12 (2006.01); C07D 405/04 (2006.01)
CPC C07D 405/14 (2013.01) [A61P 11/00 (2018.01); A61P 13/12 (2018.01); C07D 405/04 (2013.01)] 21 Claims
 
1. A compound of formula (II):

OG Complex Work Unit Chemistry
or a tautomer, stereoisomer, pharmaceutically acceptable salt, or solvate thereof,
wherein:
ring B is optionally substituted furanyl;
ring C is aryl or heteroaryl;
ring D is phenyl, pyridinyl, or pyridinyl N-oxide;
each of X, Y, and Z is independently selected from the group consisting of O, CH2, NRx and S(O)q, wherein Rx is hydrogen or alkyl;
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;
p is 0, 1, 2, 3, 4, or 5; and
q is 0, 1, or 2;
provided that when ring D is phenyl, at least two of the following are true:
(i) R1 is alkyl;
(ii) R2 is not methoxy, chloro, or trifluoromethyl; and
(iii) ring C is not unsubstituted phenyl.