# US 11,078,153 B2 · 2-difluoro substituted 4-aminocyclopentanecarboxylic acids as inhibitors of gamma-aminobutyric acid aminotransferase and human ornithine aminotransferase

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- Number: US 11,078,153 B2
- Document ID: US11078153B2
- Status: Granted
- Kind: B2
- Application number: 16/839,441
- Filed: 2020-04-03
- Published: 2020-10-08
- Granted: 2021-08-03
- Earliest claimed: 2019-04-03
- Assignees: Northwestern University
- Applicants: Northwestern University
- Inventors: Richard B. Silverman
- Web page: https://patentgrep.com/patent/US11078153B2

## CPC

- C07C 229/48: with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
- C07B 2200/07: Optical isomers
- C07C 2601/08: the ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Disclosed are enantiomerically pure cyclopentane-based compounds that are prepared by a multiple-step synthesis process. The disclosed compounds have been designed to inhibit gamma-aminobutyric acid-amino transferase (GABA-AT) activity and ornithine aminotransferase (OAT) activity. Some of the enantiomerically pure compounds inhibit OAT activity more potently than the racemic compound. The disclosed compounds may be used to selectively inhibit OAT activity, for example, to treat hepatocellular carcinoma and/or used to selected inhibit GABA-AT activity, for example, to treat neurological diseases and disorders.

## Claims

### Claim 1

An enantiomerically pure form of a compound having the following formula, or a protonated form, a deprotonated form, a zwitterionic form, a deuterated form, or a hydrate or a salt thereof:

### Claim 2 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1.

### Claim 3 (depends on 1)

A method for treating a disease or disorder in a subject in need thereof, the method comprising administering to the subject an effective amount of the compound of claim 1 or a pharmaceutically composition comprising an effective amount thereof.

### Claim 4 (depends on 3)

The method of claim 3, wherein the disease or disorder is associated with ornithine aminotransferase (OAT) activity.

### Claim 5 (depends on 3)

The method of claim 3, wherein the disease or disorder is hepatocellular cancer.

### Claim 6 (depends on 1)

A method for inhibiting activity of ornithine aminotransferase (OAT), the method comprising contacting the OAT with the compound of claim 1.

### Claim 7 (depends on 6)

The method of claim 6, wherein the OAT is present within a cell.