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Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes

A compound, AA1-AA6 technology, used in skin care preparations, skin diseases, receptors/cell surface antigens/cell surface determinants, etc., can solve problems such as skin microbiota imbalance, and achieve the goal of improving physical and immune barriers. Effect

Pending Publication Date: 2019-08-30
LUBRIZOL ADVANCED MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] However, it is not only extrinsic factors that unbalance a healthy skin microbiome

Method used

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  • Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes
  • Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes
  • Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0262] The preparation method of the compound of the present invention

[0263] The synthesis of the compounds of the present invention, their stereoisomers, their mixtures and / or their cosmetically or pharmaceutically acceptable salts can be carried out according to conventional methods known in the art, such as solid-phase peptide synthesis methods [Stewart J.M. and Young J. .D., "Solid Phase Peptide Synthesis, 2nd edition", (1984), Pierce Chemical Company, Rockford, Illinois; Bodanzsky M. and Bodanzsky A., "The practice of Peptide Synthesis", (1994), Springer Verlag, Berlin; Lloyd -Williams P. et al., "Chemical Approaches to the Synthesis of Peptides and Proteins", (1997), CRC, Boca Raton, FL, USA], synthesis in solution, enzymatic synthesis [Kullmann W. "Proteases as catalysts for enzymic syntheses of opioid peptides”, (1980), J.Biol.Chem., 255(17), 8234-8238] or any combination thereof. The compound can also be obtained by fermentation of bacterial strains, modified or ...

Embodiment 1

[0358] Get H-AA 8 -O-2-ClTrt-(R), where AA 8 is L-Asp, L-Asn or L-Glu.

[0359]Weights have been normalized. Dissolve 3.2mmol (1 equivalent) of Fmoc-L-Asp(tBu)-OH, Fmoc-L-Asn(Trt)-OH or Fmoc-L-Glu(tBu)-OH in 20ml of DCM, add 0.83 Equivalents of DIEA, coupled to dry 2-chlorotrityl resin (3.2 mmol), functionalized at 1.6 mmol / g. The mixture was stirred for 5 minutes, then 1.63 equivalents of DIEA were added. The mixture was allowed to react for 40 minutes. The remaining chloride groups were blocked by treatment with 2 ml of MeOH.

[0360] The resin was then washed and the N-terminal Fmoc group deprotected as described in the general methods.

[0361] Get H-AA 6 -O-2-ClTrt-(R) where AA 6 is L-Arg or L-Lys.

[0362] Weights have been normalized. 1.6 mmol (1 equiv) of Fmoc-Arg(Pbf)-OH or Fmoc-L-Lys(Boc)-OH dissolved in 10 ml of DCM, to which 0.83 equiv of DIEA was added, was coupled to dry 2-chlorotrityl On base resin (1.6 mmol), the functionalization was 1.6 mmol / g. Th...

Embodiment 2

[0365] Get Fmoc-W m -X n -AA 1 -AA 2 -AA 3- AAA 4 -AA 5 -AA 6 -AA 7 -AA 8 -Y p -Z q -O-2-ClTrt-(R), where AA 1 is L-Glu; AA 2 is L-Glu; AA 3 is L-Met; AA 4 is L-Gln; AA 5 is L-Arg; AA 6 is L-Arg; AA 7 Is Ala; AA 8 is L-Asp; n, m, p and q are each 0.

[0366] Weights have been normalized. 143 mg of H-L-Asp(tBu)-O-2-Cl-Trt resin with 0.98 mmol / g (0.14 mmol) functionalization were washed as described in General Methods. Following the described protocol, 5 equivalents of Fmoc-Ala-OH (Fmoc-AA 7 -OH) was coupled to the peptidyl resin for 60 minutes.

[0367] The resin was then washed as described in the general method, and the deprotection treatment of the Fmoc group was repeated for coupling of the next amino acid. Following the previously described protocol, 5 equivalents of Fmoc-L-Arg(Pbf)-OH(Fmoc-AA 6 -OH) was coupled to the peptidyl resin for 60 minutes. The resin was then washed as described in the general method, and the deprotection treatment of the F...

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Abstract

A compound of formula (I) R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-(AA7)a-(AA8)b-Yp-Zq-R2 effective in maintaining and / or improving the physical and immunological barrier functions of the skin and useful in the treatment and / or care of the skin, hair, nails and / or mucous membranes.

Description

[0001] field of invention [0002] The present invention relates to compounds effective in maintaining and / or improving the physical and immune barrier function of the skin, and to cosmetic and pharmaceutical compositions comprising the same. The compounds are useful for the treatment and / or care of the skin, hair, nails and / or mucous membranes. In particular, the compounds are useful for maintaining and / or improving the hydration of the skin and maintaining the microbial balance of the skin. Background technique [0003] The main function of the skin is to form a barrier between the host interior and the environment. The skin must protect the organism from chemical substances, UV rays, mechanical damage and pathogenic microorganisms. Most importantly, the skin must provide an effective permeability barrier to prevent loss of water and electrolytes. Skin consists of epidermis, dermis and subcutaneous tissue. The epidermis consists of 4 layers: the undifferentiated basal la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/705
CPCA61K38/00A61K8/64A61Q19/007C07K14/705A61P17/00A61P17/04A61P17/06A61P29/00A61P37/02A61P37/08C07K7/06
Inventor W·范登内斯特K·罗德里格斯比尔萨O·拉波尔塔N·加西亚桑兹N·阿尔米尼亚纳多梅内克
Owner LUBRIZOL ADVANCED MATERIALS INC
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