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Composition comprising at least one 3-amino-pyrazolopyridine derivatives

A composition and pyrazolo technology, applied in the field of dyeing keratin fibers, especially human keratin fibers such as hair, can solve the problems of inability to obtain good resistance of chromaticity properties, limited range of hues, etc.

Active Publication Date: 2007-06-13
LOREAL SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dyeing compositions described in this document do not give good chromatic properties and good resistance to external factors such as washing and light
Also, the range of hues is limited

Method used

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  • Composition comprising at least one 3-amino-pyrazolopyridine derivatives
  • Composition comprising at least one 3-amino-pyrazolopyridine derivatives
  • Composition comprising at least one 3-amino-pyrazolopyridine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0127] Example 1: N-2-Ethylpyrazolo[1,5-a]pyridine-2,3-diamine dihydrochloride

[0128]

[0129] Synthesis of 2-Methylthio-3-nitro-pyrazolo[1,5-a]pyridine

[0130]

[0131] In a 2-liter three-necked flask equipped with a mechanical stirrer and an internal temperature sensor, 111 g of 1-N-aminopyridine_iodide (0.5 mol) solution in DMF (500 rl) was prepared under nitrogen.

[0132] Then potassium carbonate (207.3, 3 equivalents) was added in one portion, followed by 1,1-bis(methylthio)-2-nitroethylene (165.2 g, 2 equivalents) in one portion. The weight of the reaction mixture increases. Then 500ml DMF was added to make the reaction mixture more fluid.

[0133] After stirring at room temperature for 48 hours, the reaction mixture was poured into 4 liters of ice water. The precipitate formed was filtered, washed with a large amount of water (5 liters), and then dried under vacuum at 80°C.

[0134] Excessive 1,1-bis(methylthio)-2-nitroethylene (30mol.%, by re-pasting) was removed...

Embodiment 2

[0156] Example 2: 2-(3-Amino-pyrazolo[1,5-a]pyridin-2-ylamino)ethyl acetone dihydrochloride

[0157]

[0158] Synthesis of 2-[(3-nitro-pyrazolo[1,5-a]pyridin-2-yl)amino]ethanol

[0159]

[0160] Add 10ml of N-methylpyrrolidone, 7.25g (0.03mol) of 2-methanesulfonyl-3-nitropyrazolo[1,5-a]pyridine and 6ml of ethanolamine into a spherical condenser, thermometer and magnetic stirring In a 50ml three-necked flask. Stir and heat to 70°C for 5 hours on an oil bath.

[0161] The yellow compound separated by pouring the reaction mixture into water was drained on the frit, and then washed several times with water. At P 2 O 5 After vacuum drying in the presence, 6.45 g of a yellow solid consistent with the expected compound was recovered.

[0162] NMR analysis ( 1 H 400MHz and 13 C100.61MHz DMSO d 6 ) Consistent with the expected structure.

[0163] The expected molecule C is mainly detected 9 H 10 N 4 O 3 Quasi-molecular ion [M+H] + , [M+Na] + And [M-H] - .

[0164] Synthesis of 2-(3-...

Embodiment 3

[0172] Example 3: 1-(3-Amino-pyrazolo[1,5-a]pyridin-1-ylamino)-propan-2-cetanol

[0173]

[0174] Synthesis of 1-[(3-nitropyrazolo[1,5-a]pyridin-2-yl)amino]propan-2-ol

[0175]

[0176] Add 10ml of N-methylpyrrolidone, 7.23g (0.03mol) of 2-methanesulfonyl-3-nitropyrazolo[1,5-a]pyridine and 7ml of 1-amino-2-propanol to the ball Condenser, thermometer and magnetic stirrer in a 50ml three-necked flask. While stirring, heat to 70°C for 5 hours on an oil bath.

[0177] Drain the yellow compound separated by pouring the reaction mixture into water on the frit, and then wash with water several times. At P 2 O 5 After vacuum drying in the presence, 6.02 g of a yellow solid consistent with the expected compound was recovered.

[0178] NMR analysis ( 1 H 400MHz and 13 C 100.61MHz DMSO d 6 ) Consistent with the expected structure.

[0179] Synthesis of 1-3-amino-pyrazolo[ 1,5-a]pyridin-1-ylamino)-propan-2-ol dihydrochloride

[0180]

[0181] Add 350ml of ethanol and 5g of zinc powde...

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PUM

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Abstract

Disclosed herein is a composition for the dyeing of keratin fibers, for example, human keratin fibers such as the hair, comprising at least one 3-amino pyrazolo-[1,5-a]-pyridine derivative or one of its addition salts and a method employing this derivative. The composition of the present disclosure makes it possible to obtain coloration in various shades that is powerful, chromatic, and aesthetic, with low selectivity and with good resistance to various aggressive factors to which the hair may be subjected, such as shampoos, the light, sweat and permanent shaping.

Description

Technical field [0001] The present invention relates to a composition for dyeing keratin fibers, especially human keratin fibers such as hair, comprising at least one specific 3-amino-pyrazolo[1,5-a]-pyridine derivative or one Its addition salts, and methods of applying these derivatives. It also relates to a 3-aminopyrazolo[1,5-a]-pyridine derivative or an addition salt thereof. Background technique [0002] It is well known that keratin fibers, especially human keratin fibers, such as hair, can be dyed with dyeing compositions, wherein the dyeing composition contains oxidation dye precursors, especially o- or p-phenylenediamines, o- or p-phenylenediamines. -Aminophenols, and heterocyclic compounds commonly referred to as oxidation bases. The oxidation dye precursor or oxidation base is a colorless or slightly colored compound. When it is combined with the oxidation product, a colored or dyed compound can be obtained through an oxidative condensation process. [0003] It is also...

Claims

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Application Information

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IPC IPC(8): A61K8/49A61Q5/10C07D471/00
CPCC07D471/04A61K8/494A61Q5/10A61K8/49
Inventor A·法德利L·威达尔S·萨贝勒
Owner LOREAL SA
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