# US 12,178,224 B1 · Use of gamma-quaternary ammonium butyrate compound in preparation of an animal feed additive

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- Number: US 12,178,224 B1
- Document ID: US12178224B1
- Status: Granted
- Kind: B1
- Application number: 18/235,852
- Filed: 2023-08-20
- Granted: 2024-12-31
- Earliest claimed: 2023-08-20
- Assignees: Anipha Technologies Pty Ltd
- Applicants: Anipha Technologies Pty Ltd
- Inventors: Xianfeng Peng; Huacheng Huang
- Web page: https://patentgrep.com/patent/US12178224B1

## CPC

- A23K 20/105: Aliphatic or alicyclic compounds
- A23K 50/60: for weanlings
- A23K 20/111: Aromatic compounds
- A23K 20/142: Amino acids; Derivatives thereof
- A23K 50/30: for swines
- A23K 50/75: for poultry
- A61K 31/205: Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
- A23K: FODDER
- 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)

## Abstract

Provided is an application of a γ-quaternary ammonium butyrate compound having formula (I) or a racemate, a stereoisomer, a geometric isomer, a tautomer, a solvate, or a feed-acceptable salt thereof in preparing an animal feed additive, the compound being added to the daily feed of animals at a certain concentration ratio, and being capable of increasing the average daily weight gain of animals under the same food intake conditions, having no significant effect on the daily feed intake of the animals, and reducing the feed-to-meat ratio. The γ-quaternary ammonium butyrate compound disclosed herein can effectively increase the rate of daily weight gain of the animals and improve the growth performance of the animals, having no side effects on the animals, being stable and safe, and improving the production efficiency of the breeding industry whilst ensuring the health of the animals.

## Claims

### Claim 1

A method of improving animal production performance, the method comprising administering an animal feed additive to an animal, wherein the animal is selected from livestock and poultry; wherein the improved production performance of the animal is improved weight gain or feed conversion efficiency compared to an animal not administered with the animal feed additive, and wherein the animal feed additive comprises a γ-quaternary ammonium butyrate compound having Formula (I), or a racemate, a stereoisomer, a geometric isomer, a tautomer, a solvate or a feed acceptable salt thereof,
wherein A is an anion; R is C1-C20 alkyl, C6-C12 aryl, C4-C12 heteroaryl, (C1-C4 alkylene)-C6-C12 aryl, or (C1-C4 alkylene)-C4-C12 heteroaryl, wherein C1-C20 alkyl is optionally substituted with one, two, three, four, or five R3, and wherein each of C6-C12 aryl, C4-C12 heteroaryl, (C1-C4 alkylene)-C6-C12 aryl, and (C1-C4 alkylene)-C4-C12 heteroaryl is optionally substituted with one, two, three, four, or five R4;
R3 is —OH, —NH2, —CN, —SH or —X1, wherein X1 is F, Cl, Br or I; and
R4 is —OH, —NH2, —NO2, —CN, —SH, —X2, —C1-C5 alkoxy, —C1-C5 alkyl, or —C1-C5 alkyl substituted with X2, wherein X2 is F, Cl, Br or I.

### Claim 2 (depends on 1)

The method of claim 1, wherein R is C1-C20 alkyl or C1-C20 alkyl substituted with one, two, three, four, or five R3.

### Claim 3 (depends on 2)

The method of claim 2, wherein R is C1-C11 alkyl or C1-C11 alkyl substituted with one, two, three, four, or five R3.

### Claim 4 (depends on 3)

The method of claim 3, wherein R is C1-C11 alkyl.

### Claim 5 (depends on 4)

The method of claim 4, wherein R is a linear C1-C11 alkyl.

### Claim 6 (depends on 5)

The method of claim 5, wherein R is C1-C3 alkyl.

### Claim 7 (depends on 1)

The method of claim 1, wherein R is C6-C12 aryl, or C4-C12 heteroaryl, or (C1-C4 alkylene)-C6-C12 aryl, or (C1-C4 alkylene)-C4-C12 heteroaryl, wherein each of C6-C12 aryl, C4-C12 heteroaryl, (C1-C4 alkylene)-C6-C12 aryl, and (C1-C4 alkylene)-C4-C12 heteroaryl is optionally substituted with one, two, three, four, or five R4.

### Claim 8 (depends on 7)

The method of claim 7, wherein R is C6-C12 aryl or (C1-C4 alkylene)-C6-C12 aryl, wherein each of C6-C12 aryl and (C1-C4 alkylene)-C6-C12 aryl is optionally substituted with one, two, three, four, or five R4.

### Claim 9 (depends on 8)

The method of claim 8, wherein R is phenyl or (C1-C4 alkylene) phenyl, wherein each of phenyl and (C1-C4 alkylene) phenyl is optionally substituted with one, two, three, four, or five R4.

### Claim 10 (depends on 1)

The method of claim 1, wherein the γ-quaternary ammonium butyrate compound has a structural formula of

### Claim 11 (depends on 1)

The method of claim 1, wherein the γ-quaternary ammonium butyrate compound having Formula (I), or the racemate, the stereoisomer, the geometric isomer, the tautomer, the solvate or the feed acceptable salt thereof is used in combination with at least one additional animal feed additive.

### Claim 12 (depends on 11)

The method of claim 11, wherein the at least one additional animal feed additive is selected from at least one of a nutritive feed additive, a non-nutritive feed additive, and a medicated feed additive.

### Claim 13 (depends on 1)

The method of claim 1, wherein the γ-quaternary ammonium butyrate compound having Formula (I), or the racemate, the stereoisomer, the geometric isomer, the tautomer, the solvate or the feed acceptable salt thereof is used in combination with at least one animal feed material.

### Claim 14 (depends on 11)

The method of claim 11, wherein the γ-quaternary ammonium butyrate compound has a structural formula of

### Claim 15 (depends on 13)

The method of claim 13, wherein the T-quaternary ammonium butyrate compound has a structural formula of