# US 11,999,737 B2 · Kinase inhibitors and related methods of use

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- Number: US 11,999,737 B2
- Document ID: US11999737B2
- Status: Granted
- Kind: B2
- Application number: 17/165,048
- Filed: 2021-02-02
- Published: 2021-05-27
- Granted: 2024-06-04
- Earliest claimed: 2014-09-25
- Assignees: Duke University
- Applicants: Duke University; UTI Limited Partnership
- Inventors: Timothy A. J. Haystead; David A. Carlson; Douglas H. Weitzel; Justin A. MacDonald; Michael P. Walsh
- Web page: https://patentgrep.com/patent/US11999737B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

The present disclosure is directed to compounds that may selectively inhibit Death Associated Protein Kinases (DAPKs) as well as PIM kinases. The compounds can be used in methods of treating various disorders, including cancers.

## Claims

### Claim 1

A compound of formula (II), or a pharmaceutically acceptable salt thereof:
wherein:
R2 is selected from the group consisting of C1-C6 alkyl, substituted aryl and optionally substituted heteroaryl;
R3 is hydrogen;
R4 and R5 together form an oxo group;
R6 is selected from the group consisting of hydrogen and —(CRaRb)n—X;
R7 is selected from the group consisting of hydrogen and —(CRaRb)n—X;
each Ra and Rb is independently selected from the group consisting of hydrogen and C1-C4 alkyl;
n is 1, 2, 3, 4, 5 or 6;
each X is independently selected from the group consisting of optionally substituted aryl, optionally substituted heteroaryl, —ORc, —CORd, —COORe, —CON(Rf)(Rg), —CN;
each Rc is independently selected from the group consisting of hydrogen, C1-C4 alkyl, and —(CH2)m—Y wherein m is 1, 2 or 3 and Y is selected from the group consisting of —OH, —O(C1-C4-alkyl), —COORe and —CON(Rf)(Rg);
each Rd is independently selected from the group consisting of optionally substituted aryl, optionally substituted heteroaryl and —(CH2)p—Z wherein p is 1, 2 or 3 and Z is selected from the group consisting of —OH, —O(C1-C4-alkyl), —COORe and —CON(Rf)(Rg); and
each Re, Rf and Rg is independently selected from the group consisting of hydrogen and C1-C4 alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is substituted phenyl.

### Claim 3 (depends on 2)

The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein R2 is phenyl substituted with a halogen, cyano, alkoxy, or C1-C6 alkyl.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R6 is hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R6 is —CH2—X, wherein X is —CORd.

### Claim 6 (depends on 5)

The compound of claim 5, or a pharmaceutically acceptable salt thereof, wherein Rd is optionally substituted aryl.

### Claim 7 (depends on 6)

The compound of claim 6, or a pharmaceutically acceptable salt thereof, wherein Rd is optionally substituted phenyl.

### Claim 8 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of: