# US 12,492,222 B2 · Lipophilic enantiomers of desacetylglucosamine muramyl dipeptide with anti-inflammatory and growth promoting activity

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- Number: US 12,492,222 B2
- Document ID: US12492222B2
- Status: Granted
- Kind: B2
- Application number: 17/912,647
- Filed: 2021-03-25
- Published: 2023-06-08
- Granted: 2025-12-09
- Earliest claimed: 2020-03-26
- Assignees: Nutrivert LLC
- Applicants: Nutrivert Inc.
- Inventors: Horace Disston Nalle, Jr.; Bernhard Kaltenboeck
- Web page: https://patentgrep.com/patent/US12492222B2

## CPC

- C07K 5/06026: {the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala}
- A23K 20/147: Polymeric derivatives, e.g. peptides or proteins
- A61K 39/39: characterised by the immunostimulating additives, e.g. chemical adjuvants
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- C07K 5/0806: {the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala}
- A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00)
- A61K 2039/5555: {Muramyl dipeptides}
- C07B 2200/07: Optical isomers
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Compositions of matter and methods to reduce inflammation in vertebrates and to promote growth and feed conversion in animals by administering an effective amount of a composition containing a mirror image molecule (enantiomer) of a lipophilic muramyl dipeptide (MDP) derivative that does not contain the N-acetylglucosamine moiety of MDP (i.e., a desmuramyl dipeptide).

## Claims

### Claim 1

An oligopeptide of the following formula:
or a pharmaceutically acceptable acid or salt thereof, wherein:
R1 is C1-C18 linear alkyl or substituted or unsubstituted aryl;
R2, R3, and R4 are each independently selected from H, substituted or unsubstituted alkyl and substituted or unsubstituted aryl;
R5 is H, unsubstituted alkyl, or substituted or unsubstituted aryl; and
X is O or NR6, wherein R6 is hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

### Claim 2 (depends on 1)

The oligopeptide of claim 1, wherein X is O.

### Claim 3 (depends on 1)

The oligopeptide of claim 1, wherein the oligopeptide has the following structure:

### Claim 4 (depends on 1)

The oligopeptide of claim 1, wherein the oligopeptide has the following structure:
wherein
R7 is substituted or unsubstituted alkyl or substituted or unsubstituted aryl; and
Y is O or NR8, wherein R8 is hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

### Claim 5 (depends on 1)

The oligopeptide of claim 1, wherein the oligopeptide is L-lactate-D-alanine-L-glutamine-hexadecyl ester.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising at least one oligopeptide of claim 1 and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 1)

A composition comprising at least one oligopeptide of claim 1 and animal feed.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the at least one oligopeptide is present in the composition in an amount of from about 0.01 mg/kg to 5 mg/kg.

### Claim 9 (depends on 7)

The composition of claim 7, wherein the composition further comprises an additive used in an animal diet.

### Claim 10 (depends on 9)

The composition of claim 9, wherein the additive comprises an enzyme, a probiotic, a prebiotic, an antioxidant, an antibiotic growth promoter, a coloring agent, or a combination thereof.

### Claim 11 (depends on 6)

A method for reducing intestinal inflammation in a human, comprising:
administering the pharmaceutical composition of claim 6 to a human having intestinal inflammation, wherein the administration reduces the intestinal inflammation.

### Claim 12 (depends on 1)

A method for promoting growth in an animal, comprising:
administering the oligopeptide of claim 1 to an animal, wherein the administration enhances the growth of the animal.

### Claim 13 (depends on 7)

A method for promoting growth in an animal, comprising:
administering the composition of claim 7 to an animal, wherein the administration enhances the growth of the animal.

### Claim 14 (depends on 1)

A method for enhancing feed conversion in an animal, comprising:
administering the oligopeptide of claim 1 to an animal, wherein the administration enhances the feed conversion of the animal.

### Claim 15 (depends on 7)

A method for enhancing feed conversion in an animal, comprising:
administering the composition of claim 7 to an animal, wherein the administration enhances the feed conversion in the animal.

### Claim 16 (depends on 1)

The oligopeptide of claim 1, wherein R5 is H.

### Claim 17 (depends on 11)

The method of claim 11, further comprising selecting a human having a disease or condition associated with intestinal inflammation.

### Claim 18 (depends on 17)

The method of claim 17, wherein the disease or condition associated with intestinal inflammation comprises inflammatory bowel disease, irritable bowel syndrome, Crohn's disease, ulcerative colitis, or a bacterial infection.