# US 10,501,516 B2 · Peptide compound

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- Number: US 10,501,516 B2
- Document ID: US10501516B2
- Status: Granted
- Kind: B2
- Application number: 16/303,975
- Filed: 2017-05-23
- Published: 2019-07-04
- Granted: 2019-12-10
- Earliest claimed: 2016-05-24
- Assignees: Takeda Pharmaceutical Company Limited
- Applicants: Takeda Pharmaceutical Company Limited
- Inventors: Taiji Asami; Ayumu Niida
- Web page: https://patentgrep.com/patent/US10501516B2

## CPC

- C07K 14/575: Hormones (derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin C07K14/665, e.g. corticotropin C07K14/695)
- A61K 38/16: Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof {(enzyme inhibitors A61K38/005)}
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- C12N 15/09: Recombinant DNA-technology
- 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)
- 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)
- 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
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)

## Abstract

The present invention relates to a peptide compound that may be useful in the treatment or prophylaxis of obesity, diabetes and the like. More specifically, the present invention relates to a peptide compound represented by the formula (I): P1-Tyr-Aib-Glu-Gly-Thr-α-MePhe-Thr-Ser-Asp-Lys(-Gly-Gly-Gly-Gly-RA10)-A11-A12-Aib-Leu-A15-Lys-Gln-A18-Gln-Iva-Glu-Phe-Val-Arg-His-Leu-Leu-Asn-Lys-Aib-Thr-Arg-Gln-Arg-A35-NH2 wherein each symbol is as defined in the specification, and the treatment or prophylaxis of obesity, diabetes and the like using the peptide compound.

## Claims

### Claim 1

A peptide represented by the formula (I):
P1-Tyr-Aib-Glu-Gly-Thr-α-MePhe-Thr-Ser-Asp-Lys(-Gly-Gly-Gly-Gly-RA10)-A11-A12-Aib-Leu-A15-Lys-Gln-A18-Gln-Iva-Glu-Phe-Val-Arg-His-Leu-Leu-Asn-Lys-Aib-Thr-Arg-Gln-Arg-A35-NH2
wherein
P1 is a group represented by the formula:
—RA1,
—CO—RA1,
—CO—ORA1,
—CO—CORA1,
—SO—RA1,
—SO2—RA1,
—SO2—ORA1,
—CO—NRA2RA3,
—SO2—NRA2RA3,
or
—C(═NRA1)—NRA2RA3
wherein RA1, RA2 and RA3 are each independently a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group;
RA10 is Pal or Oda;
A11 is Aib, Ala or Ser;
A12 is Ile or Lys;
A15 is Asp or Glu;
A18 is Ala or Arg; and
A35 is Tyr or Phe(2-F),
or a salt thereof.

### Claim 2 (depends on 1)

The peptide according to claim 1 or a salt thereof, wherein P1 is a hydrogen atom or a methyl group.

### Claim 3 (depends on 1)

The peptide according to claim 1 or a salt thereof, wherein RA10 is Pal.

### Claim 4 (depends on 1)

The peptide according to claim 1 or a salt thereof, wherein A12 is Ile.

### Claim 5 (depends on 1)

The peptide according to claim 1 or a salt thereof, wherein A15 is Glu.

### Claim 6 (depends on 1)

The peptide according to claim 1 or a salt thereof, wherein A18 is Arg.

### Claim 7 (depends on 1)

The peptide according to claim 1 or a salt thereof, wherein A35 is Tyr.

### Claim 8

H-Tyr-Aib-Glu-Gly-Thr-αMePhe-Thr-Ser-Asp-Lys(-Gly-Gly-Gly-Gly-Pal)-Aib-Ile-Aib-Leu-Glu-Lys-Gln-Arg-Gln-Iva-Glu-Phe-Val-Arg-His-Leu-Leu-Asn-Lys-Aib-Thr-Arg-Gln-Arg-Tyr-NH2
or a salt thereof.

### Claim 9

H-Tyr-Aib-Glu-Gly-Thr-αMePhe-Thr-Ser-Asp-Lys(-Gly-Gly-Gly-Gly-Pal)-Ala-Ile-Aib-Leu-Glu-Lys-Gln-Arg-Gln-Iva-Glu-Phe-Val-Arg-His-Leu-Leu-Asn-Lys-Aib-Thr-Arg-Gln-Arg-Tyr-NH2
or a salt thereof.

### Claim 10

Me-Tyr-Aib-Glu-Gly-Thr-αMePhe-Thr-Ser-Asp-Lys(-Gly-Gly-Gly-Gly-Pal)-Ser-Ile-Aib-Leu-Glu-Lys-Gln-Arg-Gln-Iva-Glu-Phe-Val-Arg-His-Leu-Leu-Asn-Lys-Aib-Thr-Arg-Gln-Arg-Tyr-NH2
or a salt thereof.

### Claim 11 (depends on 1)

A medicament comprising the peptide according to claim 1 or a salt thereof.

### Claim 12 (depends on 11)

The medicament according to claim 11, which is an activator of a Y2 receptor, a GLP-1 receptor and a GIP receptor.

### Claim 13 (depends on 11)

The medicament according to claim 11, which is an agent for the prophylaxis or treatment of obesity or diabetes.

### Claim 14 (depends on 1)

A method for the prophylaxis or treatment of obesity or diabetes in a mammal, comprising administering an effective amount of the peptide according to claim 1 or a salt thereof to the mammal.

### Claim 15 (depends on 1)

A method for activating a Y2 receptor, a GLP-1 receptor and a GIP receptor in a mammal, comprising administering an effective amount of the peptide according to claim 1 or a salt thereof to the mammal.