# US 11,299,461 B2 · Pyridin-2-yl alkylamino substituted hydroxamic acid and uses thereof

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- Number: US 11,299,461 B2
- Document ID: US11299461B2
- Status: Granted
- Kind: B2
- Application number: 16/979,503
- Filed: 2019-03-12
- Published: 2021-12-02
- Granted: 2022-04-12
- Earliest claimed: 2018-03-12
- Assignees: Hawaii Biotech, Inc.
- Applicants: Hawaii Biotech, Inc.
- Inventors: Guan-Sheng Jiao; Seong Jin Kim; Alan T. Johnson
- Web page: https://patentgrep.com/patent/US11299461B2

## CPC

- C07D 213/65: attached in position 3 or 5
- A61P 31/04: Antibacterial agents
- C07D 213/54: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 213/61: Halogen atoms or nitro radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula I are provided: wherein X is NH, or CH2, Y is a single bond, or —CHR5—, R1 is H, C1-C4 alkyl, or C1-C4 hydroxyalkyl, R2 and R2′ are each independently H, C1-C4 alkyl, or C1-C4 hydroxyalkyl, each R3 is independently H, halo, —CF3, C1-C4 alkyl, or C1-C4 alkoxy, C3 perhaloalkyl, each R4 is independently H, halo, or C1-C4 alkyl, R5 is C1-C4 alkoxy, r is integer from 0 to 3; and p is integer from 0 to 3.

## Claims

### Claim 1

A compound of formula I:
or a pharmaceutically acceptable salt, hydrate or solvate thereof
wherein
X is NH or CH2;
Y is a single bond, or —CHR5—;
R1 is H, C1-C4 alkyl, or C1-C4 hydroxyalkyl;
R2 and R2′ are each independently H, C1-C4 alkyl, or C1-C4 hydroxyalkyl;
each R3 is independently H, halo, —CF3, C1-C4 alkyl, or C1-C4 alkoxy, C3 perhaloalkyl;
each R4 is independently H, halo, or C1-C4 alkyl;
R5 is C1-C4 alkoxy;
r is integer from 0 to 3; and
p is integer from 0 to 3.

### Claim 2 (depends on 1)

The compound of claim 1 wherein X is NH and Y is a single bond.

### Claim 3 (depends on 1)

The compound of claim 1 wherein X is CH2 Y is a single bond.

### Claim 4 (depends on 1)

The compound of claim 1 wherein X is CH2 and Y is —CHR5—.

### Claim 5 (depends on 4)

The compound of claim 4 wherein R5 is methoxy.

### Claim 6 (depends on 1)

The compound of claim 1 wherein R1 is H or C1-C4 alkyl.

### Claim 7 (depends on 1)

The compound of claim 1 wherein one of R2 and R2′ is H.

### Claim 8 (depends on 5)

The compound of claim 5 wherein the other one of R2 and R2′ is C1-C4 alkyl or C1-C4 hydroxyalkyl.

### Claim 9 (depends on 1)

The compound of claim 1 wherein p is 1.

### Claim 10 (depends on 1)

The compound of claim 1 wherein R3 is C1-C4 alkyl.

### Claim 11 (depends on 1)

The compound of claim 1 wherein R3 is methoxy.

### Claim 12 (depends on 1)

The compound of claim 1 wherein R3 is halo.

### Claim 13 (depends on 1)

The compound of claim 1 wherein R3 is CF3.

### Claim 14 (depends on 1)

The compound of claim 1 wherein p is 2.

### Claim 15 (depends on 10)

The compound of claim 10 wherein both R3 are halo.

### Claim 16 (depends on 10)

The compound of claim 10 wherein one of R3 is halo and the other one of R3 is C1-C4 alkyl.

### Claim 17 (depends on 1)

The compound of claim 1 wherein at least one of R4 is halo or methyl.

### Claim 18

A compound selected from:
or a pharmaceutically acceptable salt, hydrate or solvate thereof.

### Claim 19 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 along with a pharmaceutically acceptable carrier.

### Claim 20 (depends on 1)

A method of treating a subject exposed to a Bacillus anthracis toxin comprising: administering to the subject a therapeutically effective amount of a pharmaceutical composition comprising a compound according to claim 1.

### Claim 21 (depends on 18)

The compound of claim 18, wherein the compound is selected from:
or a pharmaceutically acceptable salt hydrate or solvate thereof.“