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Stable vitamin b6 derivative

a technology of vitamin b6 and derivatives, applied in the field of stable vitamin b6 derivatives, can solve the problems of inability to light, obstacle to the practical use of these substances, etc., and achieve the effect of suppressing wrinkle formation and suppressing wrinkle formation

Inactive Publication Date: 2009-05-07
DAIICHI FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Benefits of technology

[0010]The inventors of the present invention conducted various researches to achieve the aforementioned object. As a result, they found that a vitamin B6 derivative having a particular structure in which vitamin B6 was glycosylated or made into phosphoric acid or sulfuric acid ester (hereinafter also referred to as a “vitamin B6 derivative”) at the 3-position had superior stability, and especially the stability thereof against light was remarkably improved. The inventors of the present invention further conducted researches, and found a novel compound useful as an intermediate for manufacture of the aforementioned vitamin B6 derivative, and an efficient method for producing the aforementioned vitamin B6 derivative using the aforementioned intermediate. The inventors of the present invention also found that the aforementioned vitamin B6 derivative was stably maintained in a composition such as medicaments, foodstuffs, feeds, cosmetics and the like to exhibit superior effects, and the derivative gave no influence on the stability of other vitamins in the composition. They further found that the aforementioned vitamin B6 derivative had remarkable advantageous effects, in particular, whitening effect, anti-aging effect, wrinkle suppressing effect and the like. The present invention was achieved on the basis of the aforementioned findings.
[0011]The present invention thus provides a compound represented by the following general formula (I) or a salt thereof:wherein R1 represents a glycosyl group, a phosphate group, or a cyclic phosphate group bound to R2; R2 represents —CH2OH, —CHO, —CH2NH2, —CH2-amino acid residue, or —CH2-OPO2H; and R3 represents hydrogen atom, or —PO3H2.
[0012]According to another embodiment of the present invention, there is provided a compound represented by the following general formula (IV) or a salt thereof.wherein R4 represents —CH2OH, —CHO, or —CH2NH2, or represents —CH2OH, —CHO, or —CH2NH2 which is protected with a protective group; R5 represents hydrogen atom, a protective group of hydroxyl group, a phosphate group, or a protected phosphate group; and R6 represents a glycosyl group which may have a protective group, or a phosphate group which may have a protective group, which is useful as an intermediate for the manufacture of the compound represented by the aforementioned general formula (I).
[0013]According to another embodiment of the present invention, there is provided a method for preparing a compound represented by the aforementioned general formula (I) or a salt thereof, which comprises the step of reacting a compound represented by the following general formula (II) or a salt thereof:wherein R4 represents —CH2OH, —CHO, or —CH2NH2, or represents —CH2OH, —CHO, or —CH2NH2 which is protected with a protective group; and R5 represents hydrogen atom, a protective group of hydroxyl group, a phosphate group, or a protected phosphate group, with a compound represented by the following general formula (III):R6-X   (III)wherein R6 represents a glycosyl group which may have a protective group, and X represents a leaving group, to obtain the compound represented by the aforementioned general formula (IV), and if necessary, the step of deprotecting the compound represented by the aforementioned general formula (IV).
[0014]The present invention also provides a composition for cosmetics, medicaments, foodstuffs, and / or feeds which comprises a compound represented by the following general formula (V) or a salt thereof:wherein R7 represents a glycosyl group, a phosphate group, a sulfate group, or a cyclic phosphate group bound to R8; R8 represents —CH2OH, —CHO, —CH2NH2, —CH2-amino acid residue, or —CH2OPO2H; and R9 represents hydrogen atom, or —PO3H2.
[0015]The present invention also provide a method for stabilizing a vitamin in a composition for cosmetics, medicaments, foodstuffs, and / or feeds by adding the compound represented by the general formula (V) or a salt thereof to the composition, and a composition for cosmetics, medicaments, foodstuffs, and / or feeds containing the compound represented by the general formula (V) or a salt thereof and at least one kind of vitamin, wherein stability of the vitamin is improved.

Problems solved by technology

The instability of vitamin B6 and derivatives thereof, especially the instability to light, is an obstacle for practical use of these substances.

Method used

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  • Stable vitamin b6 derivative
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Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of Pyridoxine 3-β-D-glucoside

[0092]a) 3-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-α4, α5-di-O-acetylpyridoxine

[0093]α4, α5-Di-O-acetylpyridoxine hydrochloride (4.90 g, 17.2 mmol) was added with CHCl3 (150 ml) and saturated aqueous NaHCO3 (100 ml), and the mixture was stirred at room temperature for 1 hour. Then, the organic layer was washed with saturated brine, and dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The resulting white solid (4.0 g) and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (9.74 g, 23.7 mmol) were dissolved in CH2Cl2 (70 ml), and the solution was added with silver carbonate (4.36 g, 15.8 mmol) under light shielding and refluxed under a nitrogen atmosphere, and then stirred overnight. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by column chromatography (silica gel, 600 g, eluted with a mixed solvent of n-hexane:ethyl acetate=1:2) to obtain the title compound...

example 2

Preparation of Pyridoxal 3-β-D-glucoside

[0097]a) 3-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-pyridoxal monoethylacetal

[0098]Pyridoxal monoethylacetal hydrochloride (11.0 g, 47.5 mmol) was suspended in CH2Cl2 (100 ml) under a nitrogen atmosphere, and added with triethylamine (6.63 ml, 47.5 mmol) under ice cooling, and the mixture was warmed to room temperature, and then added with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (23.4 g, 57.0 mmol). After the reaction vessel was light-shielded, the reaction mixture was added with silver carbonate (13.1 g, 47.5 mmol), and stirred at room temperature for 18 hours, and then stirring was continued at 35° C. for 24 hours. The reaction mixture was filtered, and concentrated under reduced pressure, and then the residue was purified by column chromatography (silica gel, 600 g, eluted with a mixed solvent of n-hexane:ethyl acetate=1:2) to obtain the title compound (20.8 g, 84%).

[0099]1H-NMR (CDCl3) δ ppm: 1.2-1.4 (3H, m), 2.0-2.1 (12H, m),...

example 3

Preparation of Pyridoxamine 3-β-D-glucoside

a) 3-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-pyridoxal Oxime

[0105]The compound of Example 2, b) (6.0 g, 12.1 mmol) was suspended in water (200 ml), and added with sodium acetate (1.29 g, 15.7 mmol) and hydroxylammonium chloride (1.26 g, 18.2 mmol), and the mixture was stirred for 30 minutes under reflux. The reaction mixture was cooled to room temperature, and then extracted with ethyl acetate (300 ml). The organic layer was dried over anhydrous MgSO4, and then the solvent was evaporated under reduced pressure. The residue was added with diethyl ether, and the deposited solid was collected by filtration, washed with diethyl ether, and then dried under reduced pressure to obtain the title compound (5.49 g, 89%).

[0106]1H-NMR (CDC3) δ ppm: 2.03 (3H, s), 2.03 (3H, s), 2.05 (3H, s), 2.19 (3H, s), 2.56 (3H, s), 3.5-3.7 (1H, m), 4.0-4.2 (2H, m), 4.61 (2H, brs), 4.80 (1H, d, J=7.9 Hz), 5.0 (1H, brs), 5.1-5.5 (3H, m), 8.40 (1H, s), 8.57 (1H, s),...

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Abstract

A compound represented by the following general formula (I) or a salt thereof:wherein R1 represents a glycosyl group; R2 represents —CH2OH, —CHO, —CH2NH2, —CH2-amino acid residue, or —CH2—OPO2H; and R3 represents hydrogen atom, or —PO3H2, and methods of its use in cosmetics, medicaments, foodstuffs, and / or feeds.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]The present application is a continuation of U.S. application Ser. No. 10 / 573,973, which is a National Stage of International Application PCT / JP2004 / 014768, filed Sep. 30, 2004, the disclosure of which is expressly incorporated by reference herein in its entirety. The present application also claims priority under 35 U.S.C. § 119 to Japanese Application Nos. 2003-342918, filed Oct. 1, 2003 and 2004-155624, filed May 26, 2004.TECHNICAL FIELD[0002]The present invention relates to a stable vitamin B6 derivative.BACKGROUND ART[0003]Each of pyridoxine, pyridoxal, and pyridoxamine is a substance having a vitamin B6 action, and referred to as a class of vitamin B6 together with each 5′-phosphate thereof, i.e., pyridoxine 5′-phosphate, pyridoxal 5′-phosphate, and pyridoxamine 5′-phosphate. These compounds are metabolized to give pyridoxal 5′-phosphate in vivo, and play an important role as a coenzyme for enzymes involved in amino acid metabolism....

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/49A61K31/706A61Q19/02A23L1/48A23L2/00A23L2/42A23L2/52A23L33/15A23L35/00A61K8/67A61P1/02A61P1/04A61P3/02A61P5/16A61P7/06A61P17/00A61P17/04A61P21/02A61P25/08A61P25/32A61P29/00A61Q19/00A61Q19/08C07H17/02
CPCA23K1/1603A23L1/302A61K8/673A61K31/66A61K31/706A61Q5/02C07H17/02A61Q19/004A61Q19/005A61Q19/02A61Q19/08C07F9/582A61Q19/00A23K20/174A23L33/15A61P1/02A61P1/04A61P3/02A61P5/16A61P7/06A61P17/00A61P17/04A61P21/02A61P25/08A61P25/32A61P29/00C07F9/58C07H17/00
Inventor SAKAMOTO, KEIJIWADA, KOICHIITO, HAJIMETAKE, NOBUHIROMORIMOTO, HIROSHIMANIWA, FUMIOSHIMMOTO, YUKIKO
Owner DAIICHI FINE CHEM CO LTD
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