Needle-like material and method for manufacturing needle-like material

Patent metadata

Field	Value
Publication number	US-9849271-B2
Application number	US-201414470078-A
Country	US
Kind code	B2
Filing date	Aug 27, 2014
Priority date	Feb 29, 2012
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A needle-shaped structure includes a needle-shaped projection and a support substrate supporting the projection wherein the projection contains at least a chitosan and an organic acid, places a low burden on a living body and is able to keep the microscopic form after puncture into the skin.

First claim

The invention claimed is:

1. A method of producing a needle-shaped structure having a support substrate and a needle-shaped projection projected from the support substrate, the method comprising:
preparing a liquid material comprising a chitosan material and an acid;
applying the liquid material onto an intaglio plate having a needle-shaped recess;
solidifying the liquid material applied onto the intaglio plate such that a solidified article made from the liquid material is obtained;
separating the solidified article from the intaglio plate; and
immersing separated solidified article in an aqueous alcohol solution which reduces the acid from the separated solidified article.

2. The method of producing a needle-shaped structure as defined in claim 1 , wherein the aqueous alcohol solution comprises at least one alcohol selected from the group consisting of ethanol, methanol and propanol.

3. The method of producing a needle-shaped structure as defined in claim 2 , wherein the aqueous alcohol solution has a concentration of 50-90 wt %.

4. The method of producing a needle-shaped structure as defined in claim 1 , wherein the immersing comprises immersing the separated solidified article in a first aqueous alcohol solution of a higher concentration and then in a second aqueous alcohol solution of a lower concentration.

5. The method of producing a needle-shaped structure as defined in claim 1 , wherein the chitosan material comprises at least one material selected from the group consisting of chitosan, chitin-chitosan, a chitin-chitosan derivative, glucosamine and a glucosamine derivative.

6. The method of producing a needle-shaped structure as defined in claim 1 , wherein the acid comprises at least one selected from the group consisting of acetic acid, succinic acid, citric acid, lactic acid, tartaric acid, glyoxylic acid, pyruvic acid, oxalosuccinic acid, oxaloacetic acid, acetoacetic acid, levulinic acid, oxoglutaric acid, hydrochloric acid, sulfuric acid and a hydrate thereof.

7. A method of producing a needle-shaped structure having a support substrate and a needle-shaped projection projected from the support substrate, the method comprising:
preparing a liquid material comprising a chitosan material and an acid;
applying the liquid material onto an intaglio plate having a needle-shaped recess;
solidifying the liquid material applied onto the intaglio plate such that a solidified article made from the liquid material is obtained;
separating the solidified article from the intaglio plate; and
placing separated solidified article in a solution acetylating the chitosan material in the separated solidified article.

8. The method of producing a needle-shaped structure as defined in claim 7 , wherein the chitosan material comprises at least one material selected from the group consisting of chitosan, chitin-chitosan, a chitin-chitosan derivative, glucosamine and a glucosamine derivative.

9. The method of producing a needle-shaped structure as defined in claim 7 , wherein the acid comprises at least one selected from the group consisting of acetic acid, succinic acid, citric acid, lactic acid, tartaric acid, glyoxylic acid, pyruvic acid, oxalosuccinic acid, oxaloacetic acid, acetoacetic acid, levulinic acid, oxoglutaric acid, hydrochloric acid, sulfuric acid and a hydrate thereof.

10. A method of producing a needle-shaped structure having a support substrate and a needle-shaped projection projected from the support substrate, the method comprising:
preparing a liquid material comprising a chitosan material, a first acid, and a second acid;
applying the liquid material onto an intaglio plate having a needle-shaped recess;
solidifying the liquid material such that a solidified article made from the liquid material is obtained;
separating the solidified article from the intaglio plate; and
immersing separated solidified article in an aqueous alcohol solution,
wherein the first acid is a tri- or higher valent carboxylic acid or a dicarboxylic acid having a number average molecular weight of not less than 110, and the second acid is a monocarboxylic acid or a dicarboxylic acid, having a number average molecular weight of less than 110.

11. The method of producing a needle-shaped structure as defined in claim 10 , wherein the first acid is selected from the group consisting of citric acid, tartaric acid, fumaric acid and maleic acid, and the second acid is selected from the group consisting of formic acid, acetic acid, propionic acid, lactic acid, oxalic acid and malonic acid.

12. The method of producing a needle-shaped structure as defined in claim 10 , wherein the first acid is citric acid.

13. The method of producing a needle-shaped structure as defined in claim 10 , wherein the second acid is acetic acid.

14. The method of producing a needle-shaped structure as defined in claim 10 , wherein a total amount of the first acid and the second acid is from 0.5 wt % to 40 wt % relative to the needle-shaped structure.

15. The method of producing a needle-shaped structure as defined in claim 10 , wherein the aqueous alcohol solution comprises at least one alcohol selected from the group consisting of methanol, ethanol and propanol.

16. The method of producing a needle-shaped structure as defined in claim 10 , wherein the aqueous alcohol solution has a concentration of 50 wt % to 90 wt %.

17. The method of producing a needle-shaped structure as defined in claim 10 , wherein the chitosan material is at least one member selected from the group consisting of chitosan, chitin-chitosan, a chitin-chitosan derivative, glucosamine and a glucosamine derivative.

18. The method of producing a needle-shaped structure as defined in claim 10 , wherein the projection and the support substrate are made of a material of a same composition.

19. The method of producing a needle-shaped structure as defined in claim 10 , wherein the projection has a needle shape having a height of 10 μm to 1000 μm.

20. The method of producing a needle-shaped structure as defined in claim 7 , wherein the solution includes acetic anhydride.

Assignees

• Toppan Printing Co Ltd

Inventors

• Kato Hiroyuki
• Yamamoto Takako
• Taroura Yoshikazu

Classifications

• A61K47/12

  Carboxylic acids; Salts or anhydrides thereof · CPC title

• A61M2037/0046

  Solid microneedles · CPC title

• A61K47/36

  Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin · CPC title

• B29C39/003

  characterised by the choice of material · CPC title

• A61M2037/0053

  Methods for producing microneedles · CPC title