# US 11,998,539 B2 · Substituted aminoquinolones as DGKalpha inhibitors for immune activation

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- Number: US 11,998,539 B2
- Document ID: US11998539B2
- Status: Granted
- Kind: B2
- Application number: 18/072,490
- Filed: 2022-11-30
- Published: 2023-06-29
- Granted: 2024-06-04
- Earliest claimed: 2019-11-28
- Assignees: Bayer Aktiengesellschaft; Bayer Pharma Aktiengesellschaft; Deutsches Krebsforschungszentrum
- Applicants: Bayer Aktiengesellschaft; Bayer Pharma Aktiengesellschaft; Deutsches Krebsforschungszentrum
- Inventors: Norbert Schmees; Lars Wortmann; Dennis Kirchhoff; Thi Thanh Uyen Nguyen; Nicolas Werbeck; Ulf Bömer; Kirstin Petersen; Christina Kober; Christian Lechner; Dirk Kosemund; Rienk Offringa; Mareike Grees; Benjamin Bader
- Web page: https://patentgrep.com/patent/US11998539B2

## CPC

- A61K 31/4545: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
- A61K 31/4709: Non-condensed quinolines and containing further heterocyclic rings
- A61K 31/4725: containing further heterocyclic rings
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/498: Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
- A61K 31/55: having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 35/00: Antineoplastic agents
- A61P 37/04: Immunostimulants
- C07D 215/22: attached in position 2 or 4
- C07D 215/54: attached in position 3
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/14: containing three or more hetero rings
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 513/04: Ortho-condensed systems
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention covers aminoquinolone compounds of general formula (I), in which R1, R2, R3, R4, R5, R6, R7, R8 and n are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment and/or prophylaxis of diseases, in particular of diacylglycerol kinase alpha regulated disorders, as a sole agent or in combination with other active ingredients.

## Claims

### Claim 1

A compound having the structure:
or a hydrate or solvate thereof, or a pharmaceutically acceptable salt of any of the foregoing.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound is

### Claim 3 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a hydrate or solvate thereof, or a pharmaceutically acceptable salt of any of the foregoing, and at least one pharmaceutically acceptable excipient.

### Claim 4 (depends on 2)

A pharmaceutical composition comprising a compound of claim 2 and at least one pharmaceutically acceptable excipient.

### Claim 5 (depends on 1)

A method of treating or preventing a disease or condition associated with dysregulated immune responses or aberrant DGKα signaling in a mammal, comprising administering an effective amount of a compound of claim 1, or a hydrate or solvate thereof, or a pharmaceutically acceptable salt of any of the foregoing, to the mammal.

### Claim 6 (depends on 5)

The method of claim 5, wherein the mammal is a human.

### Claim 7 (depends on 5)

The method of claim 5, wherein the disease is cancer.

### Claim 8 (depends on 5)

The method of claim 5, wherein the compound or pharmaceutically acceptable salt thereof exercises its effect through T-cell activation.

### Claim 9 (depends on 5)

The method of claim 5, wherein the disease is non-small cell lung cancer (NSCLC), gastric cancer, gastric adenocarcinoma, esophageal adenocarcinoma, melanoma, or colorectal cancer.

### Claim 10 (depends on 5)

The method of claim 5, wherein the disease is non-small cell lung cancer.

### Claim 11 (depends on 5)

The method of claim 5, wherein the disease is gastric cancer.

### Claim 12 (depends on 5)

The method of claim 5, wherein the disease is gastric adenocarcinoma or esophageal adenocarcinoma.

### Claim 13 (depends on 5)

The method of claim 5, wherein the disease is melanoma.

### Claim 14 (depends on 5)

The method of claim 5, wherein the disease is colorectal cancer.

### Claim 15

A method of treating or preventing a disease or condition associated with dysregulated immune responses or aberrant DGKα signaling in a mammal, comprising administering an effective amount of 6-fluoro-1-methyl-4-[4-(5-methyl-1,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carboxamide, to the mammal.

### Claim 16 (depends on 15)

The method of claim 15, wherein the mammal is a human.

### Claim 17 (depends on 15)

The method of claim 15, wherein the disease is cancer.

### Claim 18 (depends on 15)

The method of claim 15, wherein 6-fluoro-1-methyl-4-[4- (5-methyl-1,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carboxamide exercises its effect through T-cell activation.

### Claim 19 (depends on 15)

The method of claim 15, wherein the disease is non-small cell lung cancer (NSCLC), gastric cancer, gastric adenocarcinoma, esophageal adenocarcinoma, melanoma, or colorectal cancer.

### Claim 20 (depends on 15)

The method of claim 15, wherein the disease is non-small cell lung cancer.

### Claim 21 (depends on 15)

The method of claim 15, wherein the disease is gastric cancer.

### Claim 22 (depends on 15)

The method of claim 15, wherein the disease is gastric adenocarcinoma or esophageal adenocarcinoma.

### Claim 23 (depends on 15)

The method of claim 15, wherein the disease is melanoma.

### Claim 24 (depends on 15)

The method of claim 15, wherein the disease is colorectal cancer.