# US 10,370,324 B2 · Phenyl and pyridinyl hydroxamic acids

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- Number: US 10,370,324 B2
- Document ID: US10370324B2
- Status: Granted
- Kind: B2
- Application number: 15/807,782
- Filed: 2017-11-09
- Published: 2018-05-10
- Granted: 2019-08-06
- Earliest claimed: 2016-11-10
- Assignees: Acetylon Pharmaceuticals, Inc.
- Applicants: Acetylon Pharmaceuticals, Inc.
- Inventors: John H. van Duzer; Ralph Mazitschek
- Web page: https://patentgrep.com/patent/US10370324B2

## CPC

- C07C 259/10: having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 35/00: Antineoplastic agents
- C07D 213/81: Amides; Imides
- C07D 309/14: Nitrogen atoms not forming part of a nitro radical
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07C 2601/02: with a three-membered ring
- C07C 2601/14: The ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to pyrimidine hydroxy amide compounds, the use of such compounds in the inhibition of HDAC6, and the use of such compounds in the treatment of various diseases, disorders, or conditions related to HDAC6.

## Claims

### Claim 1

The compound of Formula I:
or a pharmaceutically acceptable salt thereof;
wherein
R is N;
R1 is H or C1-C3 alkyl;
R2 and R3 are H; or
R2 is H and R3 is phenyl, wherein the phenyl ring is optionally and independently substituted with 1, 2, or 3 halo, C1-C6 alkyl or C1-C6 alkoxy groups; or
R2 and R3 are taken together to form a C3-C6 cycloalkyl ring or a C2-C5 heterocycloalkyl ring; and
R4 is phenyl, wherein the phenyl ring is optionally and independently substituted with 1, 2, or 3 halo, C1-C6 alkyl or C1-C6 alkoxy groups.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
R1 is H.

### Claim 3 (depends on 1)

The compound of claim 1, wherein
R2 is H and R3 is phenyl, wherein the phenyl ring is optionally and independently substituted with 1, 2, or 3 halo, C1-C6 alkyl or C1-C6 alkoxy groups; and
R4 is phenyl, wherein the phenyl ring is optionally and independently substituted with 1, 2, or 3 halo, C1-C6 alkyl or C1-C6 alkoxy groups.

### Claim 4 (depends on 3)

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

### Claim 5

A compound selected from the group consisting of:
or pharmaceutically acceptable salts thereof.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.

### Claim 7

A compound of Formula Ia:
or a pharmaceutically acceptable salt thereof;
wherein
R is C(H);
R1 is H or C1-C3 alkyl;
R2 and R3 are H; or
R2 and R3 are taken together to form a C3-C6 cycloalkyl ring or a C2-C5 heterocycloalkyl ring; and
R4 is phenyl, wherein the phenyl ring is optionally and independently substituted with 1, 2, or 3 halo, C1-C6 alkyl or C1-C6 alkoxy groups.

### Claim 8 (depends on 7)

The compound of claim 7, wherein
R1 is H;
R2 and R3 are H;
R4 is phenyl, wherein the phenyl ring is optionally and independently substituted with 1, 2, or 3 halo, C1-C6 alkyl or C1-C6 alkoxy groups.

### Claim 9 (depends on 7)

The compound of claim 7, wherein
R4 is phenyl, wherein the phenyl ring is optionally and independently substituted with 1, 2, or 3 halo or C1-C6 alkoxy groups.

### Claim 10 (depends on 7)

The compound of claim 7, wherein the compound of Formula Ia is:
or a pharmaceutically acceptable salt thereof.