# US 11,078,185 B2 · Mycobacterium tuberculosis—thioredoxin reductase inhibitor as an antitubercular agent

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- Number: US 11,078,185 B2
- Document ID: US11078185B2
- Status: Granted
- Kind: B2
- Application number: 16/720,659
- Filed: 2019-12-19
- Published: 2020-04-23
- Granted: 2021-08-03
- Earliest claimed: 2017-07-04
- Assignees: Technische UniversitäT Dortmund
- Applicants: Technische Universität Dortmund
- Inventors: Oliver Koch; Luis Bering
- Web page: https://patentgrep.com/patent/US11078185B2

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A61P 31/06: for tuberculosis
- C07D 215/44: with aryl radicals attached to said nitrogen atoms
- C07D 215/46: with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to Mycobacterium tuberculosis-thioredoxin reductase inhibitors, processes for the preparation thereof, drugs containing said compounds, and the use of said compounds for manufacturing drugs.

## Claims

### Claim 1

A compound which is selected from the group consisting of:
6-methoxy-2-methyl-N-(4-((4-(pyridin-4-ylamino)phenyl)sulfonyl)phenyl)quinolin-4-amine (2):
N-(4-((4-aminophenyl)sulfonyl)phenyl)-6-methoxy-2-methylquinolin-4-amine (9):
N-(4-((4-((6-methoxy-2-methylquinolin-4-yl)amino)phenyl)sulfonyl)phenyl)acetamide (10):
6-methoxy-2-methyl-N-(4-((4-(pyrimidin-4-yl-amino)phenyl)sulfonyl)phenyl)quinolin-4-amine (24):
N-(4-((4-((3-(tert-butyl)-1H-pyrazol-5-yl)amino)phenyl)sulfonyl)phenyl)-6methoxy-2-methylquinolin-4-amine (25):
6-methoxy-N-(4-((4-((4-methoxyphenyl)amino)phenyl)sulfonyl)phenyl)-2-methylquinolin-4-amine (26):
methyl-4-((4-((4-((6-methoxy-2-methylquinolin-4-yl)amino)phenyl)sulfonyl)phenyl)amino) benzoate (27):
(4-((6-methoxy-2-methylquinolin-4-yl)amino)phenyl)(4-(pyridin-4-yl-amino) phenyl)methanone (45):
6-methoxy-2-methyl-N-(4-(4-(pyridin-4-ylamino)benzyl)phenyl)quinolin-4-amine (63):
6-methoxy-2-methyl-N-(4-(4-(pyrimidin-4-ylamino)benzyl)phenyl)quinolin-4-amine (68):
and
physiologically acceptable salts thereof.

### Claim 2 (depends on 1)

A medicament comprising at least one compound as claimed in claim 1 or a physiologically acceptable salt thereof, and optionally suitable additives and/or auxiliaries and/or optionally further active ingredients.

### Claim 3 (depends on 1)

The compound as claimed in claim 1 for use as a medicament.

### Claim 4 (depends on 1)

The compound as claimed in claim 1, for use in the treatment of tuberculosis.

### Claim 5 (depends on 4)

The compound as claimed in claim 4 for use in the treatment of tuberculosis, wherein tuberculosis is selected from the group consisting of
tuberculosis of the respiratory organs,
tuberculosis of the nervous system,
tuberculosis of other organs, and
miliary tuberculosis.

### Claim 6 (depends on 5)

The compound as claimed in claim 5 for use in the treatment of tuberculosis, wherein
tuberculosis of he respiratory organs is selected from the group consisting of
pulmonary tuberculosis,
tuberculosis of the intrathoracic lymph nodes,
tuberculosis of the larynx, trachea and bronchi, and
tuberculous pleurisy;
tuberculosis of the nervous system is selected from the group consisting of
tuberculous meningitis, and
meningeal tuberculoma;
tuberculosis of other organs is selected from the group consisting of
tuberculosis of bones and joints,
tuberculosis of the genitourinary system,
tuberculosis of peripheral lymph nodes,
tuberculosis of the intestine, peritoneum and mesenteric lymph nodes,
tuberculosis of the skin and subcutaneous tissue,
tuberculosis of the eye,
tuberculosis of the ear, and
tuberculosis of the adrenal glands.