# US 10,870,678 B2 · Chiral peptides

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- Number: US 10,870,678 B2
- Document ID: US10870678B2
- Status: Granted
- Kind: B2
- Application number: 16/092,093
- Filed: 2017-04-10
- Published: 2019-05-23
- Granted: 2020-12-22
- Earliest claimed: 2016-04-11
- Assignees: Arcuate Therapeutics, Inc.
- Applicants: Arcuate Therapeutics, Inc.
- Inventors: Andrew D. Levin
- Web page: https://patentgrep.com/patent/US10870678B2

## CPC

- C07K 5/1016: {and aromatic or cycloaliphatic}
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- C07K 5/101: {the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu}
- C07K 5/1019: {with the first amino acid being basic}
- G01N 33/68: involving proteins, peptides or amino acids {(involving lipoproteins G01N33/92)}
- G01N 33/92: involving lipids, e.g. cholesterol {, lipoproteins, or their receptors (steroid hormones G01N33/743)}
- 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)
- G01N 2500/04: Screening involving studying the effect of compounds C directly on molecule A (e.g. C are potential ligands for a receptor A, or potential substrates for an enzyme A)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- 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

The present disclosure provides certain chiral peptide agents, and uses relating thereto.

## Claims

### Claim 1

A tetrameric peptide agent having sequence (D-Phe)(D-Orn)(D-Tyr)(L-Orn)-NH2.

### Claim 2 (depends on 1)

The tetrameric peptide agent of claim 1, wherein the peptide agent is in a salt form.

### Claim 3 (depends on 2)

The tetrameric peptide agent of claim 2, wherein the salt form is a pharmaceutically acceptable salt form.

### Claim 4 (depends on 1)

A pharmaceutical composition comprising the tetrameric peptide agent of claim 1 and a pharmaceutically acceptable excipient.

### Claim 5 (depends on 4)

The pharmaceutical composition of claim 4, wherein the pharmaceutical composition is formulated for oral delivery.

### Claim 6

A method of inhibiting mitochondrial respiration in a patient or in a biological sample, the method comprising a step of administering to said patient or contacting said biological sample with a peptide agent having sequence (D-Phe)(D-Orn)(D-Tyr)(L-Orn)-NH2.

### Claim 7 (depends on 6)

The method of claim 6, wherein the tetrameric peptide agent is in a salt form.

### Claim 8 (depends on 7)

The method of claim 7, wherein the salt form is a pharmaceutically acceptable salt form.

### Claim 9 (depends on 6)

The method of claim 6, wherein the tetrameric peptide agent is administered to said patient.

### Claim 10 (depends on 9)

The method of claim 9, wherein the tetrameric peptide agent is administered in a pharmaceutical composition comprising a pharmaceutically acceptable excipient.

### Claim 11 (depends on 10)

The method of claim 10, wherein the tetrameric peptide agent is administered orally.

### Claim 12 (depends on 9)

The method of claim 9, wherein the patient has a disease, disorder, or condition is associated with mitochondrial dysfunction.

### Claim 13 (depends on 6)

The method of claim 6, wherein the tetrameric peptide agent modulates mitochondrial function in a cell of the patient or biological sample.

### Claim 14 (depends on 13)

The method of claim 13, wherein the tetrameric peptide agent increases mitochondrial reserve capacity in the cell.