# US 2014/0194469 A1 · Histone demethylase inhibitors

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0194469 A1
- Document ID: US20140194469A1
- Status: Published application
- Kind: A1
- Application number: 14/098,415
- Filed: 2013-12-05
- Published: 2014-07-10
- Earliest claimed: 2012-12-06
- Assignees: Quanticel Pharmaceuticals, Inc.
- Applicants: Quanticel Pharmaceuticals, Inc.
- Inventors: Zhe Nie; Jeffrey Alan Stafford; James Marvin Veal; Michael Brennen Wallace
- Web page: https://patentgrep.com/patent/US20140194469A1

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A61K 31/44: Non condensed pyridines; Hydrogenated derivatives thereof
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- 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

Provided herein are substituted pyrazolylpyridine, pyrazolylpyridazine, and pyrazolylpyrimidine derivative compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

## Claims

### Claim 1

A compound of Formula (II), or a pharmaceutically acceptable salt thereof,
wherein,
R1 is hydrogen, halogen, —OH, —OR5, —N(R5)2, alkyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, carbocyclylalkyl, heterocyclylalkyl, aralkyl, or heteroarylalkyl;
R2 is hydrogen, halogen, —OH, —OR5, —N(R5)2, alkyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, carbocyclylalkyl, heterocyclylalkyl, aralkyl, or heteroarylalkyl;
R4 is hydrogen or alkyl; and
each R5 is independently hydrogen, alkyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, carbocyclylalkyl, heterocyclylalkyl, aralkyl, or heteroarylalkyl.

### Claim 2 (depends on 1)

The compound or pharmaceutically acceptable salt of claim 1, wherein R4 is hydrogen.

### Claim 3 (depends on 1)

The compound or pharmaceutically acceptable salt of claim 1, wherein R4 is alkyl.

### Claim 4 (depends on 1)

The compound or pharmaceutically acceptable salt of claim 1, wherein R1 or R2 is alkyl.

### Claim 5 (depends on 1)

The compound or pharmaceutically acceptable salt of claim 1, wherein R1 or R2 is carbocyclyl.

### Claim 6 (depends on 1)

The compound or pharmaceutically acceptable salt of claim 1, wherein R1 or R2 is aryl.

### Claim 7 (depends on 1)

The compound or pharmaceutically acceptable salt of claim 1, wherein R1 or R2 is aralkyl.

### Claim 8

A compound of Formula (IV) or a pharmaceutically acceptable salt thereof,
wherein,
R1 is hydrogen, halogen, —OH, —OR5, —N(R5)2, alkyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, carbocyclylalkyl, heterocyclylalkyl, aralkyl, or heteroarylalkyl;
R2 is hydrogen, halogen, —OH, —OR5, —N(R5)2, alkyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, carbocyclylalkyl, heterocyclylalkyl, aralkyl, or heteroarylalkyl;
R3 is —O—X—Y;
R4 is hydrogen or alkyl;
each R5 is independently hydrogen, alkyl, carbocyclyl, heterocyclyl, aryl, heteroaryl, carbocyclylalkyl, heterocyclylalkyl, aralkyl, or heteroarylalkyl;
X is C1-C8 alkylene or
where n is 0 to 4; and
Y is hydrogen, carbocyclyl, aryl, or heteroaryl.

### Claim 9 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein R4 is hydrogen.

### Claim 10 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein R4 is alkyl.

### Claim 11 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein R1 and R2 are hydrogen.

### Claim 12 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein X is C1-C4 alkylene.

### Claim 13 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein X is C1-C2 alkylene.

### Claim 14 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein X is C1 alkylene.

### Claim 15 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein Y is hydrogen.

### Claim 16 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein Y is carbocyclyl.

### Claim 17 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein Y is aryl.

### Claim 18 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein Y is a phenyl.

### Claim 19 (depends on 8)

The compound or pharmaceutically acceptable salt of claim 8, wherein Y is heteroaryl.

### Claim 20

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound Formula (II) or a pharmaceutically acceptable salt thereof.

### Claim 21

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound Formula (IV) or a pharmaceutically acceptable salt thereof.

### Claim 22

A method for inhibiting a histone-demethylase enzyme comprising contacting a histone demethylase enzyme with a compound of Formula (II).

### Claim 23

A method for inhibiting a histone-demethylase enzyme comprising contacting a histone demethylase enzyme with a compound of Formula (IV).

### Claim 24

A method for treating cancer in subject comprising administering to the subject in need thereof a composition comprising a compound of Formula (II) or pharmaceutically acceptable salt thereof.

### Claim 25

A method for treating cancer in subject comprising administering to the subject in need thereof a composition comprising a compound of Formula (IV) or pharmaceutically acceptable salt thereof.