Amphiphilic polymer

Patent metadata

Field	Value
Publication number	US-10328024-B2
Application number	US-201615525835-A
Country	US
Kind code	B2
Filing date	Sep 23, 2016
Priority date	Nov 25, 2015
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

The present application relates to an amphiphilic polymer and a method of preparing the same. Furthermore, the present application relates to a micelle including a drug encapsulated by the amphiphilic polymer and a composition including the same. The amphiphilic polymer according to the present application has excellent drug encapsulation properties as well as good dispersion properties in an aqueous solution.

First claim

What is claimed is:

1. A micelle comprising:
an amphiphilic polymer comprising:
a first block (A); and
a second block (B) which is phase-separated from the first block (A) and includes a polymerization unit (B1) of an acrylic monomer or vinyl-based monomer of which a homopolymer has a solubility parameter of less than 10.0 (cal/cm 3 ) 1/2 and a polymerization unit (B2) of a polymerizable monomer having a functional group which is capable of forming a hydrogen bond,
wherein the functional group is a nitro group, an imide group, an alkoxysilane group or a cyano group;
wherein a weight ratio (B1:B2) of the polymerization unit (B1) of an acrylic monomer or vinyl-based monomer of which a homopolymer has a solubility parameter of less than 10.0 (cal/cm 3 ) 1/2 to the polymerization unit (B2) of a polymerizable monomer having a functional group which is capable of forming a hydrogen bond in the second block (B) is in a range of 1:9 to 9:1, and
a drug encapsulated by the amphiphilic polymer, wherein the second block of the amphiphilic polymer is adjacent to the drug,
wherein the drug includes an insoluble biologically active substance, and
wherein the insoluble biologically active substance is one or more selected from the group consisting of genistein, daidzein, cucurbitacin, prangenidin and a derivative thereof.

2. The micelle of claim 1 , wherein the first block (A) includes a polymer having a solubility parameter of 10.0 (cal/cm 3 ) 1/2 or more.

3. The micelle of claim 1 , wherein the first block (A) is one or more selected from the group consisting of a polyethylene glycol, a polyethylene glycol-propylene glycol copolymer, a polyvinylpyrrolidone and a polyethyleneimine.

4. The micelle of claim 1 , wherein the acrylic monomer is a compound represented by the following Formula 1 or 2:

where, in Formulas 1 and 2, Q is hydrogen or an alkyl group,
in Formula 1, B is a linear or branched alkyl group with one or more carbon atoms, an alicyclic hydrocarbon group, an aromatic substituent or a carboxyl group, and
in Formula 2, R 1 and R 2 each independently represent hydrogen, a linear or branched alkyl group with one or more carbon atoms, an alicyclic hydrocarbon group, or an aromatic substituent.

5. The micelle of claim 4 , wherein, in Formula 1, Q is hydrogen or an alkyl group with 1 to 4 carbon atoms, and B is an alkyl group with one or more carbon atoms or an alicyclic hydrocarbon group with 6 to 12 carbon atoms.

6. The micelle of claim 1 , wherein the vinyl-based monomer is a compound represented by the following Formula 3 or 4:

where, in Formula 3, X is a nitrogen atom or an oxygen atom, Y is a carbonyl group or a single bond, R 3 and R 5 each independently represent hydrogen or an alkyl group, R 3 and R 5 are connected to each other to form an alkylene group, and R 4 is an alkenyl group (but, when X is an oxygen atom, R 3 is not present);

where, in Formula 4, R 6 , R 7 and R 8 each independently represent hydrogen or an alkyl group, and R 9 is a cyano group or an aromatic substituent.

7. The micelle of claim 1 , wherein a block ratio (A:B) of the first block (A) and the second block (B) is different.

8. The micelle of claim 7 , wherein a block ratio (A:B) of the first block (A) to the second block (B) is in a range of 1:9 to 9:1.

9. The micelle of claim 7 , wherein a block ratio (A:B) of the first block (A) to the second block (B) is in a range of 3:7 to 7:3.

10. The micelle of claim 1 , wherein an average particle size is in a range of 1 to 10,000 nm.

11. A composition for preparing a particle, comprising the micelle of claim 1 .

12. A pharmaceutical or cosmetic composition, comprising the micelle of claim 1 .

13. The pharmaceutical or cosmetic composition of claim 12 , which is in the form of water-in-oil or oil-in-water emulsion.

14. A method of preparing the micelle of claim 1 comprising a step of polymerizing a polymer which forms a first block (A) with an acrylic monomer or vinyl-based monomer of which a homopolymer having a solubility parameter of less than 10.0 (cal/cm 3 ) 1/2 and a polymerizable monomer having a functional group which is capable of forming a hydrogen bond.

Assignees

• Lg Chemical Ltd
• Lg Household & Health Care Ltd

Inventors

• Yoon Jeong Ae
• Kim Su Jeong
• Lee Sun Hwa
• Shim Woo Sun
• Yoon Sung Soo
• Ju Chang Hwan
• Kim Jung A
• Kang Nae Gyu

Classifications

• A61K8/02

  characterised by special physical form · CPC title

• A61K8/11

  Encapsulated compositions · CPC title

• A61K9/51

  Nanocapsules; {Nanoparticles; (nanotubes A61K9/0092; polymeric micelles A61K9/1075; polymersomes A61K9/1273; pure drug nanoparticles A61K9/14; drug nanoparticles with adsorbed surface modifiers A61K9/141; conjugates, e.g. between drug and non-active nanoparticles, A61K47/50; preparations for in vivo diagnosis A61K49/00; with radioactive substances A61K51/00)} · CPC title

• C08G81/00

  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}) · CPC title

• C08G81/025

  containing polyether sequences · CPC title