# US 10,766,872 B2 · Compounds for the treatment of mycobacterial infections

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- Number: US 10,766,872 B2
- Document ID: US10766872B2
- Status: Granted
- Kind: B2
- Application number: 15/610,545
- Filed: 2017-05-31
- Published: 2017-11-16
- Granted: 2020-09-08
- Earliest claimed: 2011-09-29
- Assignees: The Board Institute, Inc.
- Applicants: The Broad Institute, Inc.; The General Hospital Corporation
- Inventors: Deborah Hung; Sarah Stanley; Tomohiko Kawate; Noriakie Iwase; Motohisa Shimizu
- Web page: https://patentgrep.com/patent/US10766872B2

## CPC

- C07D 311/16: substituted in position 7
- A61K 31/37: Coumarins, e.g. psoralen
- A61K 31/453: containing a six-membered ring with oxygen as a ring hetero atom
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- C07D 311/18: substituted otherwise than in position 3 or 7
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- 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 invention relates to compounds of Formula I or a pharmaceutically acceptable salt, ester or prodrug thereof:

## Claims

### Claim 1

A compound of Formula I or a pharmaceutically acceptable salt thereof:
wherein:
R1 is selected from the group consisting of phenyl, substituted phenyl, pyridinyl, and substituted pyridinyl;
R3 is hydrogen, substituted C1-C8 alkyl, or unsubstituted C1-C8 alkyl;
R4 is hydrogen, substituted C1-C8 alkyl, or unsubstituted C1-C8 alkyl;
R2 is
R6 and R7 are each independently selected from the group consisting of hydrogen and unsubstituted C1-C8 alkyl;
R5 is selected from the group consisting of
R100 and R100′ are each independently hydrogen or unsubstituted C1-C8 alkyl;
R101 and R102 are each independently hydrogen or unsubstituted C1-C8 alkyl;
wherein the term “substituted” refers to the replacement of one or more hydrogen radicals in a given structure with the radical selected from halo, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, thiol, alkylthio, arylthio, alkylthioalkyl, arylthioalkyl, alkylsulfonyl, alkylsulfonylalkyl, arylsulfonylalkyl, alkoxy, aryloxy, aralkoxy, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, alkoxycarbonyl, aryloxycarbonyl, haloalkyl, amino, cyano, nitro, alkylamino, arylamino, alkylaminoalkyl, arylaminoalkyl, aminoalkylamino, hydroxy, alkoxyalkyl, carboxy, carboxyalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, acyl, and aralkoxycarbonyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein, R1 is phenyl or unsubstituted phenyl, or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein R5 is selected from
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein R3 is unsubstituted C1-C8 alkyl, and R4 is unsubstituted C1-C8 alkyl.

### Claim 5 (depends on 1)

The compound according to claim 1 selected from Table A or a pharmaceutically acceptable salt thereof:
TABLE A
No.
Structure
1
5,7-dimethyl-6-(4-(morpholinomethyl)phenyl)-4-phenyl-2H- chromen-2-one
2
5,7-dimethyl-4-phenyl-6-(4-(piperidin-1-ylmethyl)phenyl)-2H- chromen-2-one
3
6-(4-((cyclohexylamino)methyl)phenyl)-5,7-dimethyl-4-phenyl- 2H-chromen-2-one
4
5,7-dimethyl-6-(4-((hexylamino)methyl)phenyl)-4-phenyl-2H- chromen-2-one
5
5,7-dimethyl-6-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-4- phenyl-2H-chromen-2-one
6
4-(3-aminophenyl)-5,7-dimethyl-6-(4- (morpholinomethyl)phenyl)-2H-chromen-2-one hydrochloride
7
4-(4-aminophenyl)-5,7-dimethyl-6-(4- (morpholinomethyl)phenyl)-2H-chromen-2-one
8
5,7-dimethyl-6-(4-(morpholinomethyl)phenyl)-4-(3-nitrophenyl)- 2H-chromen-2-one
9
methyl 3-(5,7-dimethyl-6-(4-(morpholinomethyl)phenyl)-2-oxo- 2H-chromen-4-yl)benzoate
10
N-(3-(5,7-dimethyl-6-(4-(morpholinomethyl)phenyl)-2-oxo-2H- chromen-4-yl)phenyl)acetamide
11
N-(3-(5,7-dimethyl-6-(4-(morpholinomethyl)phenyl)-2-oxo-2H- chromen-4-yl)phenyl)methanesulfonamide
12
ethyl (3-(5,7-dimethyl-6-(4-(morpholinomethyl)phenyl)-2-oxo- 2H-chromen-4-yl)phenyl)carbamate
13
5,7-dimethyl-6-(4-(morpholinomethyl)phenyl)-4-(pyridin-3-yl)- 2H-chromen-2-one
43
44

### Claim 6 (depends on 1)

A pharmaceutical composition comprising the compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 3)

The compound of claim 3, wherein R5 is:
or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 3)

The compound of claim 3, wherein R100 is hydrogen, or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 4)

The compound of claim 4, wherein R3 is unsubstituted C1-C3 alkyl, and R4 is unsubstituted C1-C3 alkyl, or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 9)

The compound of claim 9, wherein R3 is methyl and R4 is methyl, or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 5)

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of claim 5, or a pharmaceutically acceptable salt thereof.