# US 10,501,564 B2 · Polymer compound which has membrane-permeable peptide in side chain

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,501,564 B2
- Document ID: US10501564B2
- Status: Granted
- Kind: B2
- Application number: 15/547,840
- Filed: 2016-02-23
- Published: 2018-01-18
- Granted: 2019-12-10
- Earliest claimed: 2015-02-27
- Assignees: Josho Gakuen Educational Foundation; Adeka Corporation
- Applicants: Josho Gakuen Educational Foundation; Adeka Corporation
- Inventors: Shinji Sakuma; Kohta Mohri; Ken-ichiro Hiwatari; Kyohei Ochiai
- Web page: https://patentgrep.com/patent/US10501564B2

## CPC

- C08F 8/30: Introducing nitrogen atoms or nitrogen-containing groups
- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- C07K 2/00: Peptides of undefined number of amino acids; Derivatives thereof
- C07K 5/06026: {the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala}
- C08F 220/06: Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
- C08F 220/56: Acrylamide; Methacrylamide
- C08F 226/02: by a single or double bond to nitrogen
- C08G 81/00: Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42})
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A polymer compound has a group represented by Formula (1) or Formula (2) in a side chain. (In Formula (1), X1 represents a neutral amino acid residue or an ω-aminoalkanoic acid residue, X2 represents a membrane-permeable peptide residue, X3 represents a hydroxyl group, an amino group, an alkoxyl group having 1 to 4 carbon atoms, or a benzyloxy group, and a represents a number of from 1 to 50.) (In Formula (2), X4 represents a neutral amino acid residue or an ω-aminoalkanoic acid residue, X5 represents a membrane-permeable peptide residue, X6 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a benzyl group, an acyl group having 1 to 6 carbon atoms, an arylsulfonyl group, or a carboxyl group, and b represents a number of from 1 to 50.).

## Claims

### Claim 1

A polymer compound having a group represented by Formula (1) below or Formula (2) below in a side chain:
wherein X1 represents a residue obtained by removing a terminal amino group and a terminal carboxyl group from glycine, X2 represents a residue obtained by removing a terminal amino group and a terminal carboxyl group from octaarginine, X3 represents a hydroxyl group, an amino group, an alkoxyl group having 1 to 4 carbon atoms, or a benzyloxy group, and “a” is 4; and
wherein X4 represents a residue obtained by removing a terminal amino group and a terminal carboxyl group from glycine, X5 represents a residue obtained by removing a terminal amino group and a terminal carboxyl group from octaarginine, X6 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a benzyl group, an acyl group having 1 to 6 carbon atoms, an arylsulfonyl group, or an oxycarbonyl group, and “b” is 4;
said polymer compound comprising acrylic acid-N-vinylacetamide copolymer as a stem polymer.

### Claim 2 (depends on 1)

An introducing agent for introducing a poorly membrane-permeable compound into a cell or a mucous membrane, the introducing agent comprising the polymer compound according to claim 1.

### Claim 3 (depends on 2)

A method for introducing a poorly membrane-permeable compound into a cell, the method comprising administering the introducing agent according to claim 2 into a cell.

### Claim 4 (depends on 2)

A method for introducing a poorly membrane-permeable compound into a mucous membrane, the method comprising administering the introducing agent according to claim 2 into a mucous membrane.