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Parakeratosis inhibitor, pore shrinking agent or agent for preventing or improving rough skin, and composition for external use on the skin containing the same

A technology for parakeratosis and rough skin, applied in the direction of cosmetic preparations, skin care preparations, anhydride/acid/halide active ingredients, etc.

Active Publication Date: 2011-02-09
SHISEIDO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are currently no reports indicating that NOS inhibitors or N-amidinoglutamic acid have the effect of inhibiting parakeratosis or improving enlarged pores

Method used

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  • Parakeratosis inhibitor, pore shrinking agent or agent for preventing or improving rough skin, and composition for external use on the skin containing the same
  • Parakeratosis inhibitor, pore shrinking agent or agent for preventing or improving rough skin, and composition for external use on the skin containing the same
  • Parakeratosis inhibitor, pore shrinking agent or agent for preventing or improving rough skin, and composition for external use on the skin containing the same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example

[0163] (1) N-acetyl-N', N"-dimethyl-L-glutamic acid-1,5-diamide

[0164]Add 50 mL of methanol and 10 mL of 10% methanolic hydrochloric acid solution to 5 g of N-acetyl-L-glutamic acid, and heat to reflux for 1 hour. After air cooling, concentrate to obtain a residue, add 20 mL of 40% methylamine methanol solution to the residue, and stir at room temperature for 2 hours. The reaction solution was concentrated, dried and solidified, and recrystallized from methanol to obtain 3.8 g of the target product.

[0165] The structure of the obtained target product was confirmed by NMR (JEOL EX-400, solvent DMSO).

[0166] 1 H-NMR (ppm): 8.01(1H), 7.82(1H), 7.73(1H), 4.12(1H), 2.55(6H), 2.05(2H), 1.85(4H), 1.68(1H). 13 C-NMR (ppm): 171.8, 171.8, 169.2, 62.3, 31.8, 28.1, 25.5, 25.4, 22.5.

[0167] (2) N-acetyl-N', N"-diethyl-L-glutamic acid-1,5-diamide

[0168] Add 50 mL of methanol and 50 mL of 10% methanolic hydrochloric acid solution to 5 g of N-acetyl-L-glutamic acid, and heat to...

preparation example 1

[0266] Preparation Example 1 Lotion

[0267] (1) 1,3-Butanediol 6.0

[0268] (2) Glycerin 4.0

[0269] (3) Oleyl alcohol 0.1

[0270] (4) POE(20) sorbitan monolaurate 0.5

[0271] (5) POE (15) lauryl ester 0.5

[0272] (6) Ethanol 10.0

[0273] (7) N-carbamoyl-L-glutamic acid 1.0

[0274] (8) Purified water balance

preparation example 2

[0275] Preparation Example 2 lotion

[0276] (ethanol phase)

[0277] (1) Ethanol 10.0

[0278] (2) Oleyl alcohol 0.1

[0279] (3) POE(20) sorbitan monolaurate 0.5

[0280] (4) POE (15) lauryl ether 0.5

[0281] (5) Appropriate amount of preservatives

[0282] (6) Appropriate amount of spices

[0283] (7) N-Benzyloxycarbonyl-L-glutamic acid 0.7

[0284] (water box)

[0285] (8) 1,3-Butanediol 6.0

[0286] (9) Glycerin 4.0

[0287] (10)Ion-exchanged water balance

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Abstract

Provided are an outstandingly effective parakeratosis inhibitor, pore shrinking agent, or agent for preventing or improving rough skin, which contains as active ingredient a compound which has no problems as regards safety, such as sensory irritation, and a composition for external use on the skin containing such a compound. The aforementioned compound is selected from glutamic acid derivatives of general formula (1) or (2) and salts thereof. (A represents a carbamoyl group, a benzyloxycarbonyl group, a C1-3 alkyl group, an aryl group or an amidino group.) (Z is a C1-4 alkyl group, a C2-4 alkenyl group or the like; Y is OH, a C1-3 alkyloxy group, an aryloxy group or NR3R4; and R1-R4 are H, a C1-3 alkyl group, an aryl group, a C3-7 cycloalkyl group, a C3-7 cycloalkenyl group, a phenyl group, or a benzyl group, or NR1R2 or NR3R4 is a heterocyclic ring).

Description

[0001] related application [0002] This application claims the priority of Japanese Patent Application No. 2008-63352 filed on March 12, 2008 and Japanese Patent Application No. 2008-87497 filed on March 28, 2008, and the contents thereof are incorporated into this application. technical field [0003] The present invention relates to a parakeratosis inhibitor that suppresses parakeratosis caused by sebum; suppresses parakeratosis caused by irritating components in sebum around pores, maintains normal skin around pores, and suppresses enlarged pores with a mortar-shaped structure of pores A shrinking agent; a skin roughness preventing / improving agent for preventing / improving skin roughness caused by unsaturated fatty acids, and a composition for external use on skin having the above effects. Background technique [0004] In recent years, especially young women have been concerned about enlarged pores, and people are looking for skin external preparations that improve such e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61Q19/00A61K8/44
CPCA61K31/16A61Q1/12A61K8/0212A61K31/198A61Q1/02A61Q19/007A61K31/185A61K8/442A61K8/44A61K31/195
Inventor 饭田年以金子摩纪上沼三纪子末继胜
Owner SHISEIDO CO LTD
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