Lipid dipeptide and gel

Patent metadata

Field	Value
Publication number	US-9265833-B2
Application number	US-200913056517-A
Country	US
Kind code	B2
Filing date	Jun 19, 2009
Priority date	Aug 1, 2008
Publication date	Feb 23, 2016
Grant date	Feb 23, 2016

Abstract

A gelator that includes a lipid peptide of Formula (1) wherein R 1 is a C 9-23 aliphatic group, R 2 is a hydrogen atom or a C 1-4 alkyl group optionally having a C 1-2 branched chain, R 3 is a —(CH 2 ) n —X group, n is a number from 1 to 4, and X is an amino group, a guanidino group, a —CONH 2 group, or a 5-membered ring optionally having 1 to 3 nitrogen atoms, a 6-membered ring optionally having 1 to 3 nitrogen atoms, or a fused heterocycle including a 5-membered ring and a 6-membered ring that optionally has 1 to 3 nitrogen atoms; or a pharmaceutically usable salt of the lipid peptide.

First claim

The invention claimed is:

1. A fiber formed by self-assembly of a peptide of Formula (1b) or a pharmaceutically usable salt of the peptide of Formula (1b):

where:
R 1 is a C 12-22 aliphatic group,
R 2 is a hydrogen atom, and
R 3 is an imidazole methyl group.

2. A fiber formed by self-assembly of a mixture of:
a. a peptide of Formula (1b) or a pharmaceutically usable salt of the peptide of Formula (1b):

where:
R 1 is a C 12-22 aliphatic group,
R 2 is a hydrogen atom, and
R 3 is an imidazole methyl group; and
b. a lipid peptide of Formula (2):

where:
R 4 is a C 9-23 aliphatic group,
each of R 5 , R 6 , and R 7 is a hydrogen atom, a C 1-4 alkyl chain optionally having a C 1-2 branched chain, or —(CH 2 ) n —X, and at least one or more of R 5 , R 6 , and R 7 is —(CH 2 ) n —X,
n is a number from 1 to 4,
X is an amino group, a guanidino group, a —CONH 2 group, or a 5-membered ring optionally having 1 to 3 nitrogen atoms, a 6-membered ring optionally having 1 to 3 nitrogen atoms, or a fused heterocycle including a 5-membered ring and a 6-membered ring that optionally has 1 to 3 nitrogen atoms, and
m is a number from 1 to 4, or
a pharmacologically usable salt of the lipid peptide of Formula (2).

3. The fiber according to claim 1 , wherein the self-assembly is accelerated by addition of a surfactant.

4. The fiber according to claim 3 , wherein the surfactant is an anionic surfactant, a nonionic surfactant, or a cationic surfactant.

5. A gel comprising:
a peptide of Formula (1b) or a pharmaceutically usable salt of the peptide of Formula (1b):

where:
R 1 is a C 12-22 aliphatic group,
R 2 is a hydrogen atom, and
R 3 is an imidazole methyl group; and
a solvent.

6. A gel comprising:
the fiber as claimed in claim 1 ; and
a solvent.

7. The gel according to claim 6 , wherein the fiber adheres to or includes a compound selected from the group consisting of vitamin E (tocopherol), pyrene, azelaic acid derivatives, retinol (vitamin A alcohol), retinoic acid, hydroxycinnamic acid, caffeine, hinokitiol, carotenoids, astaxanthin, steroids, indomethacin, ketoprofen, vitamin C (ascorbic acid), vitamin B2 (riboflavin), kojic acid, glucosamine, azelaic acid, pyridoxine (vitamin B6), pantothenic acid (vitamin B5), arbutin, chitosan, phenoxyethanol, methylparaben, cytochrome c, medical drugs, and agrochemicals.

8. The gel according to claim 5 , wherein the solvent is water, an alcohol, an aqueous solution, an alcoholic solution, a hydrophilic organic solution, a higher alcohol, a fatty acid, higher fatty acid esters, a glyceride, a hydrophobic organic solution, or a miscible mixed solvent thereof.

9. The gel according to claim 8 , wherein the solvent is water, an alcohol, an aqueous solution, an alcoholic solution, a hydrophilic organic solution, a higher alcohol, a hydrophobic organic solution, or a miscible mixed solvent thereof.

10. The gel according to claim 8 , wherein the alcoholic solution is a mixed solution of at least one alcohol selected from the group consisting of methanol, ethanol, 2-propanol, and i-butanol and water.

11. The gel according to claim 8 , wherein the hydrophilic organic solution is a mixed solution of at least one hydrophilic organic solvent selected from the group consisting of acetone, dioxane, glycerin, propylene glycol, and polyethylene glycol and water.

12. The gel according to claim 8 , wherein the hydrophobic organic solution is a solution of at least one hydrophobic organic solvent selected from the group consisting of a liquid paraffin, a mineral oil, hydrogenated polyisobutene, and olive oil.

13. The gel according to claim 8 , wherein the aqueous solution is an aqueous solution dissolving at least one inorganic salt selected from the group consisting of an inorganic carbonate, an inorganic sulfate, an inorganic phosphate, and an inorganic hydrogen phosphate, or at least one organic salt selected from the group consisting of an organic amine hydrochloride and an organic amine acetate.

14. The gel according to claim 13 , wherein:
the inorganic salt is at least one inorganic salt selected from the group consisting of calcium carbonate, sodium carbonate, potassium carbonate, sodium sulfate, potassium sulfate, magnesium sulfate, potassium phosphate, sodium phosphate, disodium hydrogen phosphate, and sodium dihydrogen phosphate, and
the organic salt is at least one organic salt selected from the group consisting of ethylenediamine hydrochloride, ethylenediaminetetraacetate, and trishydroxymethylaminomethane hydrochloride.

15. The gel according to claim 5 , further comprising an antiseptic.

16. The gel according to claim 5 , wherein the gel is a sheet-shaped gel.

17. A film obtained by evaporation of a solvent from the sheet-shaped gel according to claim 16 .

18. A method of preparing a gel comprising the steps:
adding a solvent to a peptide of Formula (Ib) or a pharmaceutically usable salt of the peptide of Formula (Ib):

where:
R 1 is a C 12-22 aliphatic group,
R 2 is a hydrogen atom, and
R 3 is an imidazole methyl group;
heating a resulting mixture at a temperature of 75° C. or more to dissolve the peptide or the pharmaceutically usable salt of the peptide; and
allowing a resulting solution to cool to subject the solution to gelation.

19. A method of subjecting a solvent to gelation, comprising using as a gelator:
a lipid peptide of Formula (Ib):

where:
R 1 is a C 12-22 aliphatic group,
R 2 is a hydrogen atom, and
R 3 is an imidazole methyl group; or a pharmaceutically usable salt of the lipid peptide, wherein the method comprises the following steps:
adding a solvent to the lipid peptide of Formula (Ib) or a pharmaceutically usable salt of the lipid peptide and heating a resulting mixture at a temperature of 75° C. or more to dissolve the peptide or the pharmaceutically usable salt of the peptide; and
allowing a resulting solution to cool to subject the solution to gelation.

Assignees

• Miyamoto Misao
• Miyachi Nobuhide
• Iwama Takehisa
• Nissan Chemical Ind Ltd

Inventors

• Miyamoto Misao
• Miyachi Nobuhide
• Iwama Takehisa

Classifications

• A61P17/00

  Drugs for dermatological disorders · CPC title

• A61K47/22 Primary

  Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones · CPC title

• C07K5/06026

  the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala · CPC title

• A61K9/0014 Primary

  Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00) · CPC title

• C07K5/06139

  with the first amino acid being heterocyclic · CPC title