# US 11,078,165 B2 · Compounds for treating tuberculosis

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- Number: US 11,078,165 B2
- Document ID: US11078165B2
- Status: Granted
- Kind: B2
- Application number: 16/485,973
- Filed: 2018-02-15
- Published: 2020-07-23
- Granted: 2021-08-03
- Earliest claimed: 2017-02-15
- Assignees: Nanyang Technological University; National University of Singapore
- Applicants: Nanyang Technological University; National University of Singapore
- Inventors: Gerhard Grüber; Roderick Wayland Bates; Adam Hotra; Thomas Dick; Kevin Pethe
- Web page: https://patentgrep.com/patent/US11078165B2

## CPC

- C07D 239/48: Two nitrogen atoms
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/4545: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
- A61K 31/47: Quinolines; Isoquinolines
- A61K 31/505: Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61P 31/06: for tuberculosis
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to pyrimidine compounds and compositions for treating tuberculosis. These compounds may be used to target the F1 domain of F-ATP synthase and may be used with bedaquiline or 6-chloro-2-ethyl-N-[[4-[4-[4-(trifluoromethoxy)phenyl]piperidin-1-yl]phenyl]methyl]imidazo[1,2-a]pyridine-3-carboxamide (Q203) or a combination thereof.

## Claims

### Claim 1

A composition comprising a compound having a structure represented by the following formula:
wherein R1 and R1a are independently H, halogen, C1-C4 alkyl, C1-C4 alkoxy, OH;
R2═H, C1-C4 alkyl, C1-C4 alkyl alcohol, C1-C4 alkoxy, —CH2COOEt;
R3═H, C1-C4 alkyl;
R4═H, halogen, C1-C4 alkyl, C1-C4 alkoxy;
X, Y and Z are independently C or N, or a pharmaceutically acceptable salt thereof; and
bedaquiline or
6-chloro-2-ethyl-N-[[4-[4-[4-(trifluoromethoxy)phenyl]piperidin-1-yl]phenyl]methyl]imidazo[1,2-a]pyridine-3-carboxamide (Q203), or
a combination thereof.

### Claim 2 (depends on 1)

A kit for treating tuberculosis, the kit comprising the composition of claim 1.

### Claim 3 (depends on 1)

A method of treating tuberculosis in a patient, wherein the method comprises administering to a patient, a therapeutically effective amount of the composition of claim 1.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein R2 of the compound is ethyl and R3 of the compound is H.

### Claim 5 (depends on 1)

The composition according to claim 1, wherein X of the compound is N, Y and Z of the compound are C.

### Claim 6 (depends on 1)

The composition according to claim 1, wherein R1 of the compound is selected from the group consisting of 3-Br, 3-F, 3-OH, 4-Me and 4-OMe.

### Claim 7 (depends on 1)

The composition according to claim 1, wherein R1a of the compound is selected from the group consisting of 5-Br, 5-F and 5-OH.

### Claim 8 (depends on 1)

The composition according to claim 1, wherein R1a of the compound is hydrogen.

### Claim 9 (depends on 1)

The composition according to claim 1, wherein R2 of the compound is selected from the group consisting of —CH2CH2OH, —CH2COOEt, methyl, ethyl and isopropyl.

### Claim 10 (depends on 1)

The composition according to claim 1, wherein the compound is selected from the group of one of the following structures:
or a pharmaceutically acceptable salt thereof.