# US 10,118,903 B2 · Aminotriazole-based KDM1A inhibitors as epigenetic modulators

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- Number: US 10,118,903 B2
- Document ID: US10118903B2
- Status: Granted
- Kind: B2
- Application number: 15/115,342
- Filed: 2015-02-06
- Published: 2017-01-05
- Granted: 2018-11-06
- Earliest claimed: 2014-02-07
- Assignees: MUSC Foundation for Research Development
- Applicants: Musc Foundation for Research Development
- Inventors: Patrick M. Woster; Craig J. Kutz
- Web page: https://patentgrep.com/patent/US10118903B2

## CPC

- C07D 249/14: Nitrogen atoms
- C07D 257/06: with nitrogen atoms directly attached to the ring carbon atom
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

In some aspects, the present invention provides compounds of the formula (IV), wherein the variables are as defined herein, which may be used as inhibitors of histone demethylase or spermine oxidase. Also provided herein are pharmaceutical compositions of the compounds and methods using the compounds in the treatment of diseases such as cancer and cardiovascular disease.

## Claims

### Claim 1

A compound of the formula:
wherein:
R1 is halo, hydroxy, amino, nitro, cyano, alkyl(C≤12), or substituted alkyl(C≤12);
Y1 is alkanediyl(C≤12), alkylaminodiyl(C≤12), alkoxydiyl(C≤12), or a substituted version of any of these groups;
X1 is —O—, —S—, or —NR3—, wherein R3 is hydrogen or alkyl(C≤6); and
R2 is aryl(C≤12), aralkyl(C≤12), heteroaryl(C≤12), heteroaralkyl(C≤12), or a substituted version of any of these groups;
provided that R2 is not phenyl when X1 is —O—;
or a pharmaceutically acceptable salt or tautomer thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the formula is further defined as:
wherein:
R1 is halo, hydroxy, amino, nitro, cyano, alkyl(C≤12), or substituted alkyl(C≤12);
Y1 is alkanediyl(C≤12), alkylaminodiyl(C≤12), alkoxydiyl(C≤12), or a substituted version of any of these groups;
X1 is —O—, —S—, or —NR3—, wherein R3 is hydrogen or alkyl(C≤6);
R2 is aryl(C≤12), aralkyl(C≤12), heteroaryl(C≤12), heteroaralkyl(C≤12), or a substituted version of any of these groups;
provided that R2 is not phenyl when X1 is —O—;
or a pharmaceutically acceptable salt of tautomer thereof.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 is halo.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R1 is —Cl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein X1 is —O—.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R2 is aryl(C≤12).

### Claim 7 (depends on 6)

The compound of claim 6, wherein R2 is 1-napthyl or 2-napthyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the formula is selected from:
or a pharmaceutically acceptable salt or tautomer thereof.

### Claim 9

A compound of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 and an excipient.

### Claim 11 (depends on 1)

A method of treating a cardiac reperfusion injury comprising administering to a patient a therapeutically effective amount of a compound of claim 1.

### Claim 12 (depends on 11)

The method of claim 11, wherein R1 is halo.

### Claim 13 (depends on 11)

The method of claim 11, wherein Y1 is alkylaminodiyl(C≤12).

### Claim 14 (depends on 11)

The method of claim 11, wherein X1 is —O—, —S—, or —NH—.

### Claim 15 (depends on 11)

The method of claim 11, wherein R2 is aryl(C≤12) or substituted aryl(C≤12).

### Claim 16 (depends on 11)

The method of claim 11, wherein the compound is selected from:
or a pharmaceutically acceptable salt or tautomer, thereof.

### Claim 17 (depends on 1)

A method of preventing tissue damage related to ischemia or reperfusion injury comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1.

### Claim 18 (depends on 17)

The method of claim 17, wherein the tissue is cardiac tissue.