# US 2021/0277062 A9 · Cyclic peptide and a medicament, external preparation and cosmetic comprising said cyclic peptide

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- Number: US 2021/0277062 A9
- Document ID: US20210277062A9
- Status: Published application
- Kind: A9
- Application number: 16/745,520
- Filed: 2020-01-17
- Published: 2021-09-09
- Earliest claimed: 2015-05-29
- Assignees: IGISU Co., Ltd.
- Applicants: Igisu Co., Ltd.
- Inventors: Kyoko Endo; Yori Endo
- Web page: https://patentgrep.com/patent/US20210277062A9

## CPC

- C07K 7/64: Cyclic peptides containing only normal peptide links
- A61K 8/64: Proteins; Peptides; Derivatives or degradation products thereof
- A61K 38/03: Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
- A61K 38/10: Peptides having 12 to 20 amino acids {(A61K38/043 - A61K38/046 take precedence)}
- A61K 38/12: Cyclic peptides {, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C (A61K38/043 - A61K38/046 take precedence)}
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 7/10: Antioedematous agents; Diuretics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/04: Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 11/02: Nasal agents, e.g. decongestants
- A61P 13/12: of the kidneys
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/04: Antipruritics
- A61P 17/10: Anti-acne agents
- A61P 17/14: for baldness or alopecia
- A61P 17/16: Emollients or protectives, e.g. against radiation
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/02: Immunomodulators
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 7/00: Preparations for affecting hair growth
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/00: Preparations for care of the skin
- A61Q 19/02: for chemically bleaching or whitening the skin
- A61Q 19/04: for chemically tanning the skin (topical sun or radiation screening or tanning preparations A61Q17/04)
- A61Q 19/06: for countering cellulitis
- A61Q 19/08: Anti-ageing preparations
- A61Q 19/10: Washing or bathing preparations
- C07K 7/08: having 12 to 20 amino acids (gastrins C07K14/595; somatostatins C07K14/655; melanotropins C07K14/68)
- 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
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

The present invention is aimed for providing a novel peptide with a high drug efficacy and strong effect, a medicament or external preparation comprising it, specifically a prophylactic or therapeutic for dermatitis, rhinitis or alopecia, or a hair growth stimulant, a hair growing agent, an antipruritic or a skin-care product. The present invention achieved said aim by providing a cyclic peptide having an amino acid sequence expressed by the Formula I or a derivative thereof or a pharmaceutically acceptable salt thereof, wherein the amino acid sequence does not have a peptide bond that is not between the amino acids constituting the amino acid sequence.

## Claims

### Claim at position 1

-15. (canceled)

### Claim 16

A method of using an external preparation comprising applying the external preparation to skin and/or mucosa of a subject, wherein the external preparation comprises a cyclic peptide having an amino acid sequence expressed by the Formula I:
wherein,
X1 denotes Gly, Val, Ala, Ser or Thr,
X2 denotes Arg, Gln or His,
X3 denotes Lys or Arg,
X4 denotes Met, Leu or Ile,
X5 denotes Ile or Val,
X6 denotes Ser or Gly,
X7 denotes Ser or Ala,
X8 denotes Ser, Gln, Val, Ala, Thr, Leu, Ile or Met,
X9 denotes Ser, Val, Ala or Thr,
X10 denotes Gly or Arg,
X11 denotes Leu, Met, Ile, Val or Ala,
X12 denotes Gly, Ser or Ala, and
the line connecting two Cys denotes a disulfide bond,
and wherein said amino acid sequence does not have a peptide bond that is not between the amino acids constituting said amino acid sequence,
or a derivative thereof or a pharmaceutically acceptable salt thereof.

### Claim 17 (depends on 16)

The method of using the external preparation according to claim 16, wherein the mucosa is labial, oral, nasal, ocular or vaginal mucosa.

### Claim 18 (depends on 16)

The method of using the external preparation according to claim 16 for treating and/or preventing dermatitis, for alleviating or resolving itch, for treating eczematous or other erosion or ulcer, or for skin-care.

### Claim 19 (depends on 16)

The method of using the external preparation according to claim 16 for treating and/or preventing alopecia, and/or for stimulating hair growth, and/or for growing hair.

### Claim 20 (depends on 16)

The method of using the external preparation according to claim 16 for treating and/or preventing rhinitis.

### Claim 21

(canceled)

### Claim 22

(canceled)

### Claim 23 (depends on 16)

The method according to claim 16, wherein X1-X12 are selected from the group consisting of following (1)-(12):
(1) X1 denotes Gly,
(2) X2 denotes Arg, Gln or His,
(3) X3 denotes Lys or Arg,
(4) X4 denotes Met, Leu or Ile,
(5) X5 denotes Ile,
(6) X6 denotes Ser or Gly,
(7) X7 denotes Ser or Ala,
(8) X8 denotes Ser, Gln, Val, Ala, Thr, Leu, Ile or Met,
(9) X9 denotes Ser, Val, Ala or Thr,
(10) X10 denotes Gly or Arg,
(11) X11 denotes Leu, and
(12) X12 denotes Gly,
or a derivative thereof or a pharmaceutically acceptable salt thereof.

### Claim 24 (depends on 16)

The method according to claim 16 selected from the cyclic peptides of SEQ ID NOs: 3-8 and SEQ ID NOs: 16-75, or a derivative thereof or a pharmaceutically acceptable salt thereof.

### Claim 25 (depends on 16)

The method according to claim 16, wherein the derivative is substituted by a substituent which is capable of replacing a hydrogen atom, hydroxyl group, carboxy group, amino group or imino group in the cyclic peptide.

### Claim 26 (depends on 16)

The method according to claim 16, wherein the cyclic peptide is formed by deleting 1 to 4 amino acids in the cyclic peptide expressed by any one of the Formulae (I-a)-(I-e), or by replacing them with or adding them other amino acids, and wherein the cyclic peptide has an equal function with the cyclic peptide expressed by each of said formulae.

### Claim 27 (depends on 16)

The method according to claim 16, wherein the external preparation is an ingredient for a dermatitis therapeutic, dermatitis prophylactic, antipruritic, antiphlogistic, wound epithelialization-accelerating agent or skin-care product.

### Claim 28 (depends on 27)

The method according to claim 27, wherein the skin-care product is used for moisturizing, and/or for preventing or improving rough skin, and/or for sebum/acne care, and/or for alleviating irritation/anti-inflammation, and/or for skin-lightening, and/or for anti-aging, and/or for preventing/alleviating ultraviolet lesion, and/or for slimming, and/or for skin-cleansing.

### Claim 29 (depends on 16)

The method according to claim 16, wherein the external preparation is a bath agent, a body-cleansing agent or a hair-cleansing agent.

### Claim 30 (depends on 16)

The method according to claim 16, wherein the external preparation is an alopecia therapeutic, an alopecia prophylactic, a hair growing agent and/or a hair growth stimulant.

### Claim 31 (depends on 16)

The method according to claim 16, wherein the external preparation is a rhinitis therapeutic and/or rhinitis prophylactic.

### Claim 32 (depends on 16)

The method according to claim 16, wherein the external preparation is a cosmetic.

### Claim 33 (depends on 16)

The method according to claim 16, wherein the external preparation is a solid, semi-solid, powder, liquid, spray, ointment, cream, emulsion, gel or patch formulation.

### Claim 34 (depends on 16)

The method according to claim 16, wherein the external preparation is used as a pharmaceutical product, a quasi-drug or a cosmetic product.