The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Mar. 15, 2022

Filed:

Jun. 23, 2020
Applicants:

Eastern Virginia Medical School, Norfolk, VA (US);

The Regents of the Univ. of California Santa Cruz, Oakland, CA (US);

The U.s. Dept of Health & Human Services, Bethesda, MD (US);

Thomas Jefferson University, Philadelphia, PA (US);

Inventors:

David J. Maloney, Point Of Rocks, MD (US);

Diane K. Luci, Germantown, MD (US);

Ajit Jadhav, Chantilly, VA (US);

Theodore Holman, Santa Cruz, CA (US);

Jerry L. Nadler, Norfolk, VA (US);

Michael Holinstat, Wallingford, PA (US);

David Taylor-Fishwick, Norfolk, VA (US);

Anton Simeonov, Bethesda, MD (US);

Adam Yasgar, Washington, DC (US);

Steven McKenzie, Springfield, PA (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07C 311/44 (2006.01); A61P 7/02 (2006.01); C07D 211/28 (2006.01); C07D 213/76 (2006.01); C07D 217/02 (2006.01); C07D 217/22 (2006.01); C07D 235/30 (2006.01); C07D 239/69 (2006.01); C07D 261/16 (2006.01); C07D 263/58 (2006.01); C07D 277/52 (2006.01); C07D 277/82 (2006.01); C07D 295/135 (2006.01); C07D 333/36 (2006.01); C07D 417/12 (2006.01);
U.S. Cl.
CPC ...
C07C 311/44 (2013.01); A61P 7/02 (2018.01); C07D 211/28 (2013.01); C07D 213/76 (2013.01); C07D 217/02 (2013.01); C07D 217/22 (2013.01); C07D 235/30 (2013.01); C07D 239/69 (2013.01); C07D 261/16 (2013.01); C07D 263/58 (2013.01); C07D 277/52 (2013.01); C07D 277/82 (2013.01); C07D 295/135 (2013.01); C07D 333/36 (2013.01); C07D 417/12 (2013.01);
Abstract

Human lipoxygenases (LOXs) are a family of iron-containing enzymes involved in catalyzing the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling molecules are involved in a number of physiologic responses such as platelet aggregation, inflammation, and cell proliferation. Platelet-type 12-(S)-LOX (12-LOX) is of particular interest because of its demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Disclosed herein is the identification and medicinal chemistry optimization of a 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide-based scaffold. The compounds display nM potency against 12-LOX and excellent selectivity over related lipoxygenases and cyclooxygenases. In addition to possessing favorable ADME properties, the compounds also inhibit PAR-4 induced aggregation and calcium mobilization in human platelets, and reduce 12-HETE in mouse/human beta cells. The compounds can also be used in methods for treating or preventing a 12-lipoxygenase mediated disease or disorder.


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