# US 2016/0355469 A1 · Anticonvulsant compounds

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- Number: US 2016/0355469 A1
- Document ID: US20160355469A1
- Status: Published application
- Kind: A1
- Application number: 15/174,099
- Filed: 2016-06-06
- Published: 2016-12-08
- Earliest claimed: 2015-06-05
- Assignees: Owen-Barry Pharmaceuticals Inc.
- Applicants: Owen-Barry Pharmaceuticals Inc.
- Inventors: Michael Poulter; TONY DURST
- Web page: https://patentgrep.com/patent/US20160355469A1

## CPC

- C07C 255/31: having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 2601/02: with a three-membered ring
- C07C 2601/16: the ring being unsaturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present application relates to compounds and methods for reducing the severity of convulsant activity, or epileptic seizures.

## Claims

### Claim 1

A compound represented by the following formula (I):
wherein,
R=H, CH3, C2 to C6 (linear or branched), cC3H5, cC5H9, cC6H11, CH=CH2, or CH2Ar,
R1=R2=H or CH3,
R3=R4=H or CH3,
R5=H, CH3, OCH3, OCH2Ar, Cl, or Br, and
R6=H or CH3.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R=H, CH3, C2 to C6 (linear or branched), cC3H5, cC5H9, or cC6H11.

### Claim 3 (depends on 2)

The compound of claim 2, wherein R5=H or CH3.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R=H, CH3, or C2 to C6 (linear or branched).

### Claim 5 (depends on 4)

The compound of claim 4, wherein R=H or CH3.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound represented by the formula (I) is 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)pentanenitrile.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound represented by the formula (I) is 3-methyl-2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)butanenitrile.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 11 (depends on 1)

The compound of claim 1, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 13

A pharmaceutical composition for reducing the severity of convulsant activity, comprising a compound represented by the following formula (I) or a pharmaceutically acceptable salt or solvate thereof, and a pharmaceutically acceptable excipient:
wherein,
R=H, CH3, C2 to C6 (linear or branched), cC3H5, cC5H9, cC6H11, CH=CH2, or CH2Ar,
R1=R2=H or CH3,
R3=R4=H or CH3,
R5=H, CH3, OCH3, OCH2Ar, Cl, or Br, and
R6=H or CH3.

### Claim 14 (depends on 13)

The pharmaceutical composition of claim 13, wherein R=H, CH3, C2 to C6 (linear or branched), cC3H5, cC5H9, or cC6H11.

### Claim 15 (depends on 14)

The pharmaceutical composition of claim 14, wherein R5=H or CH3.

### Claim 16 (depends on 15)

The pharmaceutical composition of claim 15, wherein R=H, CH3, or C2 to C6 (linear or branched).

### Claim 17 (depends on 16)

The pharmaceutical composition of claim 16, wherein R=H or CH3.

### Claim 18 (depends on 13)

The pharmaceutical composition of claim 13, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 19 (depends on 13)

The pharmaceutical composition of claim 13, wherein the compound represented by the formula (I) is 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)pentanenitrile.

### Claim 20 (depends on 13)

The pharmaceutical composition of claim 13, wherein the compound represented by the formula (I) is 3-methyl-2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)butanenitrile.

### Claim 21 (depends on 13)

The pharmaceutical composition of claim 13, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 22 (depends on 13)

The pharmaceutical composition of claim 13, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 23 (depends on 13)

The pharmaceutical composition of claim 13, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 24 (depends on 13)

The pharmaceutical composition of claim 13, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 25

A method for reducing the severity of convulsant activity, comprising administering to a subject a therapeutically effective amount of a compound represented by the following formula (I):
wherein,
R=H, CH3, C2 to C6 (linear or branched), cC3H5, cC5H9, cC6H11, CH=CH2, or CH2Ar,
R1=R2=H or CH3,
R3=R4=H or CH3,
R5=H, CH3, OCH3, OCH2Ar, Cl, or Br, and
R6=H or CH3.

### Claim 26 (depends on 25)

The method of claim 25, wherein R=H, CH3, C2 to C6 (linear or branched), cC3H5, cC5H9, or cC6H11.

### Claim 27 (depends on 26)

The method of claim 26, wherein R5=H or CH3.

### Claim 28 (depends on 27)

The method of claim 27, wherein R=H, CH3, or C2 to C6 (linear or branched).

### Claim 29 (depends on 28)

The method of claim 28, wherein R=H or CH3.

### Claim 30 (depends on 25)

The method of claim 25, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 31 (depends on 25)

The method of claim 25, wherein the compound represented by the formula (I) is 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)pentanenitrile.

### Claim 32 (depends on 25)

The method of claim 25, wherein the compound represented by the formula (I) is 3-methyl-2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)butanenitrile.

### Claim 33 (depends on 25)

The method of claim 25, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 34 (depends on 25)

The method of claim 25, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 35 (depends on 25)

The method of claim 25, wherein the compound represented by the formula (I) is a compound represented by the following formula:

### Claim 36 (depends on 25)

The method of claim 25, wherein the compound represented by the formula (I) is a compound represented by the following formula:
