WO1994008969A1 - Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives - Google Patents

Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives Download PDF

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Publication number
WO1994008969A1
WO1994008969A1 PCT/EP1993/002644 EP9302644W WO9408969A1 WO 1994008969 A1 WO1994008969 A1 WO 1994008969A1 EP 9302644 W EP9302644 W EP 9302644W WO 9408969 A1 WO9408969 A1 WO 9408969A1
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Prior art keywords
nitropyrazole
bromo
hydroxyethyl
amino
benzyl
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PCT/EP1993/002644
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German (de)
French (fr)
Inventor
Hans Neunhoeffer
Stefan Gerstung
Thomas Clausen
Wolfgang R. Balzer
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Wella Aktiengesellschaft
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Priority to EP93921874A priority Critical patent/EP0618902A1/en
Priority to JP6509556A priority patent/JPH07502542A/en
Priority to BR9305675A priority patent/BR9305675A/en
Publication of WO1994008969A1 publication Critical patent/WO1994008969A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38Nitrogen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16Halogen atoms or nitro radicals

Definitions

  • the present invention relates to a process for the preparation of 4,5-diaminopyrazole derivatives of the general formula (I)
  • R 1 and R 2 independently of one another denote hydrogen, a C 1 -C 4 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, and also new pyrazole derivatives, including 4,5-diaminopyrazole derivatives which act as dye precursors, for example for hair dyes.
  • DE-OS 2 141 700 describes a one-step process according to which 5-amino-1-methylpyrazole can be obtained from N, N-dimethylaminoacrylonitrile and methylhydrazine in a yield of 71 percent.
  • the 5-amino-1-methylpyrazole obtained by the processes described can be obtained in a yield of 23 percent to 5-amino-1-methyl-4-nitropyrazole implement.
  • Catalytic reduction of this product provides according to V.P. Perevalov et al., Khim. Geterotsicl. Soedin. 8__, p. 1090 (1985), l-methyl-4,5-diaminopyrazole-dihydrochloride in a yield of approx. 79 percent.
  • the overall yield over the stages mentioned is 7 to 13 percent.
  • DE-OS 38 43 892 discloses a process for the preparation of 4,5-diamino-1-methylpyrazole in which 2-chloroacrylonitrile with hydrazine (G. Ege, Angew. Chem, 86, p. 237 (1974 )) is cyclized. After acetylation of the amino group, nitration and elimination of the protective group, the tautomeric compounds 3-amino-4-nitropyrazole and 5-amino-4-nitropyrazole are obtained in a total yield of approximately 41 percent.
  • tautomeric quantity is alkylated with dimethyl sulfa
  • an isomer mixture is obtained in 70 percent yield, which is chromatographically divided into the isomeric compounds 5-amino-1-me- thyl-4-nitropyrazole (25 percent) and 3-amino-l-methyl-4-nitropyrazole (45 percent) can be separated.
  • the corresponding diamino compounds can be obtained by reduction.
  • the overall yield of l-methyl-4,5-diaminopyrazole is less than 10 percent.
  • DE-OS 3 432 983 discloses a process for the preparation of 5-amino-1- (2'-hydroxyethyl) -4-nitropyrazole. Starting from 5-amino-l- (2'-hydroxyethyl) pyrazole-4-carboxylic acid, the compound is obtained in a yield of 59 percent by decarboxylation, subsequent nitrosation and hydrogenation.
  • the object of the present invention was therefore to provide a process for the isomerically pure preparation of differently substituted 4,5-diaminopyrazole derivatives.
  • R 1 and R 2 independently of one another denote hydrogen, a C 1 -C 6 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, characterized in that
  • R3 and R4 independently of one another denote a Ci to C6 alkyl radical, a C2 to C4 hydroxyalkyl radical or a benzyl radical, substituted in the 5-position and then
  • 3,5-dibromo-4-nitropyrazole (IV) serves as the starting compound for the synthesis of 4,5-diamino-pyrazole derivatives (I), which can be prepared in the following manner:
  • the 3,5-dibromo-4-nitropyrazole (IV) is firstly reacted with C 1 -C 6 -alkyl-, C2- to C4-hydroxyalkyl or benzyl halides in dimethylformamide (DMF) (process I) or alkylated in the 1-position by reaction with Ci to C6 alkyl, C2 to C4 hydroxyalkyl or benzyl sulfate and alkali (method II).
  • DMF dimethylformamide
  • an equimolar amount of 3,5-dibromo-4-nitropyrazole, dissolved in absolute DMF, is added dropwise over a period of one hour to an initial charge of sodium hydride in absolute DMF, with stirring at room temperature.
  • an equimolar amount of C 1 -C 6 -alkyl, C 2 -C 4 -hydroxyalkyl or benzyl halide, preferably chloride or bromide, dissolved in DMF is added dropwise, and the reaction mixture is heated to 80 ° C. for three hours .
  • the solvent is then distilled off in vacuo and the residue is recrystallized from methylene chloride.
  • the 3,5-dibromo-4-nitropyrazole is dissolved in aqueous alkali, preferably 2N sodium or potassium hydroxide solution, and with a two to five-fold molar amount of C 1 -C 6 -alkyl-, C2- to C4-hydroxyalkyl - or benzyl sulfate added.
  • aqueous alkali preferably 2N sodium or potassium hydroxide solution
  • C 1 -C 6 -alkyl-, C2- to C4-hydroxyalkyl - or benzyl sulfate added.
  • the mixture is left to react at room temperature for 15 hours, the precipitated product is then filtered off, washed with water until the washing solution is pH-neutral and dried in vacuo.
  • N-substituted 3,5-dibromo-4-nitropyrazoles of the general formula (II) are heated in an aqueous, alcoholic or aqueous-alcoholic solution of C 1 -C 6 -alkyl-, C 2 ⁇ to C4-hydroxyalkyl or benzylamine or in the corresponding amine itself, as a solvent, to a temperature of 60 to 80 ° C.
  • Methanol and / or ethanol are preferably used as alcohols.
  • the compounds of the general formula (III) are then hydrogenated using hydrogen using a palladium / activated carbon catalyst with a palladium content of 10% by weight.
  • a palladium / activated carbon catalyst with a palladium content of 10% by weight.
  • two methods are available for this.
  • two spatula tips, approx. 100 mg, of the catalyst are added to the alcoholic, preferably ethanolic, solution of a compound of general formula (III) and the batch is transferred to an autoclave.
  • the mixture is stirred at room temperature for 1 to 6 hours, preferably 2 to 4 hours.
  • the catalyst is then filtered off through a glass filter crucible and the product is precipitated as a salt with a quantity of sulfuric acid which is equimolar to the pyrazole compound used or a double-molar quantity of hydrochloric acid.
  • process (2) 2 spatula tips of the above-described catalyst and an amount of sulfuric acid equimolar to the starting compound are added to the aqueous solution of a compound of the general formula (III) and the batch in a hydrogenation flask shaken at room temperature under a hydrogen atom (normal pressure).
  • a glass filter crucible is filtered off over the reaction mixture, the filtrate is concentrated and the product is crystallized out by adding ethanol.
  • R in which R3 is a Ci to C6 alkyl radical, a C2 to C4 hydroxyalkyl radical or a benzyl radical examples of compounds of the formula (II) are 3,5-dibromo-l-methyl-4-nitropyrazole, 3,5-dibromo-l-ethyl-4-nitropyrazole, 3,5-dibromo-l -isopropyl-4-nitropyrazole, 3,5-dibromo-l- (2'-hydroxyethyl) -4-nitropyrazole and 1-benzyl-3,5-dibromo-4-nitropyrazole.
  • R3 and R4 independently of one another denote a Ci to C6 alkyl radical, C2 to C4 hydroxyalkyl radical or a benzyl radical.
  • the present invention further relates to new 4,5-diaminopyrazole derivatives of the general formula (V)
  • R a and R are hydrogen, a C 1 -C 6 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, with the proviso that when R is hydrogen, R a is not hydrogen, methyl or 2-hydroxyethyl.
  • the compounds of the formula (V) can be used as dye precursors in oxidation hair colorants for dyeing hair (see example of use).
  • Ci to C6-alkyl-, C2 to C4-hydroxyalkyl- or benzyl sulfate are added to a solution of 5 g (18.5 mmol) of 3,5-dibromo-4-nitropyrazole in 50 ml of 2N sodium hydroxide solution. is allowed to stir vigorously at room temperature for 15 hours and finally the precipitated product is filtered off, washed with water until the washing solution is pH-neutral and dries in vacuo.
  • Process I gives, using 2-bromopropane, 13.14 g (60 percent of theory) of 3,5-dibromo-l-isopropyl-4-nitropyrazole in the form of brown-yellow crystals with a melting point of 72 to 73 ° C.
  • (III) is in a hydrogenation flask with an equimolar amount of 97 percent sulfuric acid, 2 spatula tips palladium / activated carbon catalyst (10 percent by weight palladium) and the amount of water indicated at room temperature under hydrogen atmosphere (normal pressure) over the in the period specified in the following production examples.
  • the course of the reaction is checked by means of thin layer chromatography. After the starting material has been completely converted, the react tion mixture filtered through a glass filter crucible. After the solvent has been distilled off, the product is crystallized from ethanol.
  • the filtrate is concentrated to 10 ml. Then 10 ml of ethanol are added, whereupon the product crystallizes out in the form of colorless crystals with a melting point of 188 ° C. 0.1 g (34 percent of theory) of 4-amino- (3) 5-ethylaminopyrazole hydrosulfate is obtained.
  • 100.00 g 50 g of the above hair dye are mixed with 50 g of hydrogen peroxide solution (6 percent) immediately before use.
  • the mixture is then applied to blonde natural hair and left to act at a temperature of 40 ° C for 30 minutes.
  • the hair is then rinsed with water and dried.
  • the hair is colored in a fashionable purple tone.

Abstract

The present invention relates to a process for producing 4,5-diamino pyrazole derivatives of general formula (I) in which R1 and R2 are mutually independently hydrogen, a C1 to C6 alkyl residue or a C2 to C4 hydroxy alkyl residue, which may be used as colorant pre-products, e.g. for hair colorants, and novel pyrzole derivatives. The use of the process of the invention makes it possible to obtain 4,5-diamino pyrazole derivatives of general formula (I) without isomers and with good yields.

Description

Beschreibung description
Verfahren zur Herstellung von 4,5-Diaminopyrazol-Deri- vaten, deren Veirwendung zum Färben von Haaren sowie neue Pyrazol-DerivateProcess for the preparation of 4,5-diaminopyrazole derivatives, their use for dyeing hair and new pyrazole derivatives
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von 4,5-Diaminopyrazol-Derivaten der allgemeinen Formel (I)The present invention relates to a process for the preparation of 4,5-diaminopyrazole derivatives of the general formula (I)
Figure imgf000003_0001
Figure imgf000003_0001
RiRi
in der Ri und R2 unabhängig voneinander Wasserstoff, einen Ci- bis Cs-Alkylrest oder einen C2- bis C4-Hydro- xyalkylrest bedeuten, sowie neue Pyrazol-Derivate, unter anderem 4,5-Diaminopyrazol-Derivate, die als Farbstoff- Vorstufen, zum Beispiel für Haarfarbstoffe, verwendet werden können.in which R 1 and R 2 independently of one another denote hydrogen, a C 1 -C 4 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, and also new pyrazole derivatives, including 4,5-diaminopyrazole derivatives which act as dye precursors, for example for hair dyes.
Es sind in der Literatur bereits mehrere Verfahren zur Herstellung von 4,5-Diaminopyrazol-Derivaten der Formel (I) bekannt. Diese Verfahren sind jedoch in vielerlei Hinsicht unbefriedigend.Several processes for the preparation of 4,5-diaminopyrazole derivatives of the formula (I) are already known in the literature. However, these methods are unsatisfactory in many ways.
So wird beispielsweise nach H. Dorn et al. , Chem. Ber. 98, S. 3368 (1965), ausgehend von Ethoxymethylen-cyan- essigsäureethylester und Methylhydrazin die 5-Amino-l- methylpyrazol-4-carbonsäure erhalten, aus der durch Decarboxylierung, in einer Gesamtausbeute von 40 Pro¬ zent, das 5-Amino-l-methylpyrazol entsteht.For example, according to H. Dorn et al. , Chem. Ber. 98, p. 3368 (1965), starting from ethyl ethoxymethylene-cyanoacetate and methylhydrazine to obtain the 5-amino-l-methylpyrazole-4-carboxylic acid, from which by Decarboxylation, in a total yield of 40 percent, the 5-amino-1-methylpyrazole is formed.
In der DE-OS 2 141 700 ist ein Einstufenverfahren be¬ schrieben, nach dem aus N,N-Dimethylaminoacrylnitril und Methylhydrazin das 5-Amino-l-methylpyrazol in einer Aus¬ beute von 71 Prozent erhalten werden kann.DE-OS 2 141 700 describes a one-step process according to which 5-amino-1-methylpyrazole can be obtained from N, N-dimethylaminoacrylonitrile and methylhydrazine in a yield of 71 percent.
Nach M.A. Khan et al. , Can. J. Chem. .49., S. 3566 (1971), läßt sich das nach den beschriebenen Verfahren erhaltene 5-Amino-l-methylpyrazol mit einer Ausbeute von 23 Pro¬ zent zum 5-Amino-l-methyl-4-nitropyrazol umsetzen. Kata- lytische Reduktion dieses Produktes liefert nach V.P. Perevalov et al., Khim. Geterotsicl. Soedin. 8__, S. 1090 (1985), l-Methyl-4,5-diaminopyrazol-dihydrochlorid in einer Ausbeute von ca. 79 Prozent. Die Gesamtausbeute über die genannten Stufen beträgt 7 bis 13 Prozent.According to M.A. Khan et al. , Can. J. Chem.. 49., P. 3566 (1971), the 5-amino-1-methylpyrazole obtained by the processes described can be obtained in a yield of 23 percent to 5-amino-1-methyl-4-nitropyrazole implement. Catalytic reduction of this product provides according to V.P. Perevalov et al., Khim. Geterotsicl. Soedin. 8__, p. 1090 (1985), l-methyl-4,5-diaminopyrazole-dihydrochloride in a yield of approx. 79 percent. The overall yield over the stages mentioned is 7 to 13 percent.
Gesamtausbeuten von bis zu 46 Prozent werden erhalten, wenn man das 5-Amino-l-methylpyrazol nach H. Dorn et al., Liebigs Ann. Chem. 717 , S. 118 (1968), mit Isoamyl- nitrit zum 5-Amino-l-methyl-4-nitropyrazol umsetzt und mit Zinn(II)chlorid zum 4,5-Diamino-l-methylpyrazol reduziert.Overall yields of up to 46 percent are obtained if the 5-amino-l-methylpyrazole according to H. Dorn et al., Liebigs Ann. Chem. 717, p. 118 (1968), with isoamyl nitrite to give 5-amino-1-methyl-4-nitropyrazole and reduced with tin (II) chloride to 4,5-diamino-1-methylpyrazole.
Aus der DE-OS 38 43 892 ist ein Verfahren zur Herstel¬ lung von 4,5-Diamino-l-methylpyrazol bekannt, in dem 2-Chloracrylnitril mit Hydrazin (G. Ege, Angew. Chem, 86, S. 237 (1974)) cyclisiert wird. Nach Acetylierung der Aminogruppe, Nitrierung und Abspaltung der Schutz¬ gruppe erhält man die tautomeren Verbindungen 3-Amino-4- nitropyrazol und 5-Amino-4-nitropyrazol in einer Gesamt¬ ausbeute von ca. 41 Prozent. Alkyliert man das Tautome- renge isch mit Dimethylsulfa , so erhält man in 70 pro- zentiger Ausbeute ein Isomerengemisch, das sich chroma¬ tographisch in die isomeren Verbindungen 5-Amino-l-me- thyl-4-nitropyrazol (25 Prozent) und 3-Amino-l-methyl- 4-nitropyrazol (45 Prozent) auftrennen läßt. Durch Re¬ duktion können die entsprechenden Diamino-Verbindungen erhalten werden. Die Gesamtausbeute von l-Methyl-4,5- diaminopyrazol beträgt weniger als 10 Prozent.DE-OS 38 43 892 discloses a process for the preparation of 4,5-diamino-1-methylpyrazole in which 2-chloroacrylonitrile with hydrazine (G. Ege, Angew. Chem, 86, p. 237 (1974 )) is cyclized. After acetylation of the amino group, nitration and elimination of the protective group, the tautomeric compounds 3-amino-4-nitropyrazole and 5-amino-4-nitropyrazole are obtained in a total yield of approximately 41 percent. If the tautomeric quantity is alkylated with dimethyl sulfa, an isomer mixture is obtained in 70 percent yield, which is chromatographically divided into the isomeric compounds 5-amino-1-me- thyl-4-nitropyrazole (25 percent) and 3-amino-l-methyl-4-nitropyrazole (45 percent) can be separated. The corresponding diamino compounds can be obtained by reduction. The overall yield of l-methyl-4,5-diaminopyrazole is less than 10 percent.
Aus der DE-OS 3 432 983 ist ein Verfahren zur Her¬ stellung von 5-Amino-l-(2'-hydroxyethyl)-4-nitropyrazol bekannt. Ausgehend von 5-Amino-l-(2'-hydroxyethyl)pyra- zol-4-carbonsäure wird die Verbindung durch Decarboxy- lierung, anschließender Nitrosierung und Hydrierung, in einer Ausbeute von 59 Prozent erhalten.DE-OS 3 432 983 discloses a process for the preparation of 5-amino-1- (2'-hydroxyethyl) -4-nitropyrazole. Starting from 5-amino-l- (2'-hydroxyethyl) pyrazole-4-carboxylic acid, the compound is obtained in a yield of 59 percent by decarboxylation, subsequent nitrosation and hydrogenation.
Neben den zum Teil geringen Ausbeuten haben die beschriebenen Verfahren weitere Nachteile. So sind viele Ausgangsverbindungen, wie zum Beispiel Ethoxymethylcyan- essigsäureethylester oder N,N-Dimethylaminoacrylnitril, nicht käuflich erhältlich oder nur durch zum Teil aufwendige Synthesen herstellbar. Darüberhinaus werden Hydrazinderivate als giftig und zum Teil krebserregend eingestuft.In addition to the sometimes low yields, the processes described have further disadvantages. For example, many starting compounds, such as, for example, ethyl ethoxymethylcyanoacetate or N, N-dimethylaminoacrylonitrile, are not commercially available or can only be prepared by in part complex syntheses. In addition, hydrazine derivatives are classified as toxic and in part carcinogenic.
Die Herstellung von 4,5-Diaminopyrazol-Derivaten, die am Stickstoffatom der Aminogruppe in 5-Position substitu¬ iert sind, ist nicht beschrieben.The preparation of 4,5-diaminopyrazole derivatives which are substituted in the 5-position on the nitrogen atom of the amino group is not described.
Aufgabe der vorliegenden Erfindung war es daher, ein Verfahren zur isomerenreinen Herstellung von unter¬ schiedlich substituierten 4,5-Diaminopyrazol-Derivaten zur Verfügung zu stellen.The object of the present invention was therefore to provide a process for the isomerically pure preparation of differently substituted 4,5-diaminopyrazole derivatives.
Es wurde nunmehr gefunden, daß sich die gestellte Aufgabe durch ein Verfahren zur Herstellung von 4,5-Di- aminopyrazol-Derivaten der allgemeinen Formel (I)
Figure imgf000006_0001
It has now been found that the object is achieved by a process for the preparation of 4,5-diaminopyrazole derivatives of the general formula (I)
Figure imgf000006_0001
II.
RiRi
in der Ri und R2 unabhängig voneinander Wasserstoff, einen Ci- bis Cß-Alkylrest oder einen C2- bis C4-Hydro- xyalkylrest bedeuten, dadurch gekennzeichnet, daß manin which R 1 and R 2 independently of one another denote hydrogen, a C 1 -C 6 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, characterized in that
(A) 3,5-Dibrom-4-nitropyrazol mit einem C]_- bis Cδ-Al- kyl-, C2- bis C4-Hydroxyalkyl- oder Benzylhalogenid oder einem Ci- bis Cδ-Alkyl, C2- bis C4-Hydroxy- alkyl-oder Benzylsulfat zu Verbindungen der allge¬ meinen Formel (II)(A) 3,5-dibromo-4-nitropyrazole with a C] _ to Cδ alkyl, C2 to C4 hydroxyalkyl or benzyl halide or a Ci to Cδ alkyl, C2 to C4 hydroxy alkyl or benzyl sulfate to compounds of the general formula (II)
Figure imgf000006_0002
Figure imgf000006_0002
in der R3 einen Ci- bis Cδ-Alkylrest, einen C2- bis C4-Hydroxyalkylrest oder einen Benzylrest bedeutet, umsetzt, (B) die Verbindungen der allgemeinen Formel (II) mit Ci- bis Cδ-Alkyl-, C2- bis C4-Hydroxyalkyl- oder Benzyl- amin zu Verbindungen der allgemeinen Formel (III)in which R3 denotes a C 1 -C 6 -alkyl radical, a C 2 -C 4 -hydroxyalkyl radical or a benzyl radical, (B) the compounds of the general formula (II) with Ci- to Cδ-alkyl-, C2- to C4-hydroxyalkyl- or benzylamine to give compounds of the general formula (III)
Figure imgf000007_0001
Figure imgf000007_0001
II.
R3 R 3
in der R3 und R4 unabhängig voneinander einen Ci- bis C6-Alkylrest, einen C2- bis C4-Hydroxyalkylrest oder einen Benzylrest bedeuten, in 5-Position substituiert und sodannin which R3 and R4 independently of one another denote a Ci to C6 alkyl radical, a C2 to C4 hydroxyalkyl radical or a benzyl radical, substituted in the 5-position and then
(C) die Verbindungen der allgemeinen Formel (III) durch katalytische Hydrierung zu den Verbindungen der allgemeinen Formel (I) reduziert,(C) the compounds of the general formula (III) are reduced to the compounds of the general formula (I) by catalytic hydrogenation,
hervorragend lösen läßt. Das vorstehend aufgeführte Ver¬ fahren ist daher ein Gegenstand der Erfindung.can be solved excellently. The above-mentioned method is therefore an object of the invention.
Das allgemeine Reaktionsschema ist nachstehend angege¬ ben.
Figure imgf000008_0001
The general reaction scheme is given below.
Figure imgf000008_0001
Figure imgf000008_0002
i
Figure imgf000008_0002
i
RiRi
(I)(I)
Als Ausgangsverbindung für die Synthese von 4,5-Diamino- pyrazol-Derivaten (I) dient das bekannte 3,5-Dibrom-4- nitropyrazol (IV), welches auf folgende Weise darge¬ stellt werden kann:The known 3,5-dibromo-4-nitropyrazole (IV) serves as the starting compound for the synthesis of 4,5-diamino-pyrazole derivatives (I), which can be prepared in the following manner:
Nach R. Hüttel et al. , Chem. Ber. .88./ S. 1577 (1955), erhält man.durch Nitrierung von Pyrazol mit einem Schwe¬ felsäure-Salpetersäure-Gemisch das 4-Nitropyrazol, das nach H.J. Klebe et al. , Synthesis 1973. S. 294 unter milderen Bedingungen durch Nitrierung von Pyrazol zum N-Nitropyrazol und anschließender Umlagerung, mit Hilfe von Schwefelsäure (R. Hüttel et al., Chem. Ber. .8J3., S. 1586 (1955)), erhalten werden kann. Anschließende Bromierung nach J.P.H. Juffermanns et al . , J. Org. Chem. 51, S. 4656 (1986), liefert das 3,5-Dibrom-4-nitropyra- zol (IV). Nach dem erfindungsgemäßen Verfahren wird zunächst das 3,5-Dibrom-4-nitropyrazol (IV) durch Umsetzung mit Ci- bis Cß-Alkyl-, C2- bis C4-Hydroxyalkyl- oder Benzylhalo- geniden in Dimethylformamid (DMF) (Verfahren I) oder durch Umsetzung mit Ci- bis C6-Alkyl-, C2- bis C4-Hydro- xyalkyl- oder Benzylsulfat und Lauge (Verfahren II) in 1-Position alkyliert.According to R. Hüttel et al. , Chem. Ber. .88. / P. 1577 (1955), the 4-nitropyrazole obtained by nitrating pyrazole with a sulfuric acid / nitric acid mixture, which according to HJ Klebe et al. , Synthesis 1973. p. 294 under milder conditions by nitration of pyrazole to N-nitropyrazole and subsequent rearrangement, with the aid of sulfuric acid (R. Hüttel et al., Chem. Ber. .8J3 . , P. 1586 (1955)), can be obtained. Subsequent bromination according to JPH Juffermanns et al. , J. Org. Chem. 51, p. 4656 (1986), provides the 3,5-dibromo-4-nitropyrazole (IV). In the process according to the invention, the 3,5-dibromo-4-nitropyrazole (IV) is firstly reacted with C 1 -C 6 -alkyl-, C2- to C4-hydroxyalkyl or benzyl halides in dimethylformamide (DMF) (process I) or alkylated in the 1-position by reaction with Ci to C6 alkyl, C2 to C4 hydroxyalkyl or benzyl sulfate and alkali (method II).
Nach Verfahren I wird zu einer Vorlage von Natriumhydrid in absolutem DMF, unter Rühren bei Raumtemperatur, eine äquimolare Menge von 3,5-Dibrom-4-nitropyrazol, gelöst in absolutem DMF, über einem Zeitraum von einer Stunde zugetropft. Nach Beendigung der Gasentwicklung tropft man eine äquimolare Menge Ci- bis Cß-Alkyl-, C2-bis C4-Hydroxyalkyl- oder Benzylhalogenid, bevorzugt -chlorid oder -bromid, gelöst in DMF, zu und erhitzt das Reaktionsgemisch drei Stunden lang auf 80 °C. Anschließend wird das Lösungmittel im Vakuum abdestil¬ liert und der Rückstand aus Methylenchlorid umkristal¬ lisiert.According to method I, an equimolar amount of 3,5-dibromo-4-nitropyrazole, dissolved in absolute DMF, is added dropwise over a period of one hour to an initial charge of sodium hydride in absolute DMF, with stirring at room temperature. After the evolution of gas has ceased, an equimolar amount of C 1 -C 6 -alkyl, C 2 -C 4 -hydroxyalkyl or benzyl halide, preferably chloride or bromide, dissolved in DMF, is added dropwise, and the reaction mixture is heated to 80 ° C. for three hours . The solvent is then distilled off in vacuo and the residue is recrystallized from methylene chloride.
Nach Verfahren II wird das 3,5-Dibrom-4-nitropyrazol in wäßriger Lauge, vorzugsweise 2N Natron- oder Kalilauge, gelöst und mit einer zwei- bis fünffachen molaren Menge an Ci-bis Cδ-Alkyl-, C2- bis C4-Hydroxyalkyl- oder Ben¬ zylsulfat versetzt. Unter kräftigem Rühren läßt man 15 Stunden lang bei Raumtemperatur reagieren, filtriert an¬ schließend das ausgefallene Produkt ab, wäscht mit Wasser bis die Waschlösung pH-neutral reagiert und trocknet im Vakuum.According to process II, the 3,5-dibromo-4-nitropyrazole is dissolved in aqueous alkali, preferably 2N sodium or potassium hydroxide solution, and with a two to five-fold molar amount of C 1 -C 6 -alkyl-, C2- to C4-hydroxyalkyl - or benzyl sulfate added. With vigorous stirring, the mixture is left to react at room temperature for 15 hours, the precipitated product is then filtered off, washed with water until the washing solution is pH-neutral and dried in vacuo.
Nach beiden Verfahren erhält man isomerenreine N-substi-, tuierte 3,5-Dibrom-4-nitropyrazole der allgemeinen Formel (II) in guten Ausbeuten. In einem anschließenden Schritt erhitzt man die N-sub- stituierten 3,5-Dibrom-4-nitropyrazole der allgemeinen Formel (II) in einer wäßrigen, alkoholischen oder wä߬ rig-alkoholischen Lösung von Ci- bis Cδ-Alkyl-, C2~bis C4-Hydroxyalkyl- oder Benzylamin oder in dem ent¬ sprechenden Amin selbst, als Lösungsmittel, auf eine Temperatur von 60 bis 80 °C. Als Alkohole werden bevorzugt Methanol und/oder Ethanol verwendet. Nach einer Reaktionszeit von 1 bis 20 Stunden, gießt man das abgekühlte Reaktionsgemisch auf 20 bis 150 ml Wasser und filtriert das abgeschiedene Produkt ab. Anschließend wäscht man mit Wasser (10 bis 20 ml) und trocknet im Vakuum. Man erhält isomerenreine 5-Amino-3-brom-4-nitro- pyrazol-Derivate der allgemeinen Formel (III) in guten Ausbeuten.Both processes give isomerically pure N-substituted, 3,5-dibromo-4-nitropyrazoles of the general formula (II) in good yields. In a subsequent step, the N-substituted 3,5-dibromo-4-nitropyrazoles of the general formula (II) are heated in an aqueous, alcoholic or aqueous-alcoholic solution of C 1 -C 6 -alkyl-, C 2 ~ to C4-hydroxyalkyl or benzylamine or in the corresponding amine itself, as a solvent, to a temperature of 60 to 80 ° C. Methanol and / or ethanol are preferably used as alcohols. After a reaction time of 1 to 20 hours, the cooled reaction mixture is poured into 20 to 150 ml of water and the separated product is filtered off. Then it is washed with water (10 to 20 ml) and dried in vacuo. Isomerically pure 5-amino-3-bromo-4-nitro-pyrazole derivatives of the general formula (III) are obtained in good yields.
Die Verbindungen der allgemeinen Formel (III) werden an¬ schließend, unter Verwendung eines Palladium-Aktivkohle- Katalysators mit einem Palladiumanteil von 10 Gewichts¬ prozent, mit Wasserstoff hydriert. Erfindungsgemäß ste¬ hen dazu zwei Verfahren zur Verfügung. Nach Verfahren (1) wird der alkoholischen, bevorzugt ethanolischen, Lö¬ sung einer Verbindung der allgemeinen Formel (III) zwei Spatelspitzen, ca. 100 mg, des Katalysators zugefügt und der Ansatz in einen Autoklaven überführt. Bei 50 bar Wasserstoffatmosphäre wird bei Raumtemperatur 1 bis 6 Stunden lang, bevorzugt 2 bis 4 Stunden, gerührt. Anschließend wird der Katalysator über einen Glasfilter- tiegel abfiltriert und das Produkt, mit einer zur einge¬ setzten Pyrazolverbindung äquimolaren Menge Schwefel¬ säure oder zweifachmolaren Menge Salzsäure als Salz aus¬ gefällt. Nach Verfahren (2) werden der wäßrigen Lösung einer Verbindung der allgemeinen Formel (III) 2 Spatel¬ spitzen des vorstehend beschriebenen Katalysators und eine zur Ausgangsverbindung äquimolare Menge Schwefel¬ säure zugegeben und der Ansatz in einem Hydrierkolben bei Raumtemperatur unter Wasserstoffatomospäre (Normal¬ druck geschüttelt. Sobald die dünnschichtchromatogra- phische Untersuchung der Reaktionsmischung keinen Hinweis mehr auf noch vorliegendes Edukt gibt, wird über das Reaktionsgemisch einen Glasfiltertiegel abfiltriert, das Filtrat eingeengt und das Produkt durch Zugabe von Ethanol auskristallisiert.The compounds of the general formula (III) are then hydrogenated using hydrogen using a palladium / activated carbon catalyst with a palladium content of 10% by weight. According to the invention, two methods are available for this. According to process (1), two spatula tips, approx. 100 mg, of the catalyst are added to the alcoholic, preferably ethanolic, solution of a compound of general formula (III) and the batch is transferred to an autoclave. In a 50 bar hydrogen atmosphere, the mixture is stirred at room temperature for 1 to 6 hours, preferably 2 to 4 hours. The catalyst is then filtered off through a glass filter crucible and the product is precipitated as a salt with a quantity of sulfuric acid which is equimolar to the pyrazole compound used or a double-molar quantity of hydrochloric acid. According to process (2), 2 spatula tips of the above-described catalyst and an amount of sulfuric acid equimolar to the starting compound are added to the aqueous solution of a compound of the general formula (III) and the batch in a hydrogenation flask shaken at room temperature under a hydrogen atom (normal pressure). As soon as the thin-layer chromatographic analysis of the reaction mixture gives no indication of any educt still present, a glass filter crucible is filtered off over the reaction mixture, the filtrate is concentrated and the product is crystallized out by adding ethanol.
Man erhält nach beiden Verfahren isomerenreine 4,5- Diaminopyrazol-Derivate der allgemeinen Formel (I) in guten Ausbeuten.Isomerically pure 4,5-diaminopyrazole derivatives of the general formula (I) are obtained in good yields by both processes.
Die Verbindungen der allgemeinen Formel (I), in denen Ri Wasserstoff bedeutet, liegen als Tauto ere vor. Die Positionen 3 und 5 im Pyrazolring sind nicht unter¬ scheidbar.The compounds of the general formula (I) in which R 1 is hydrogen are present as tautomers. Positions 3 and 5 in the pyrazole ring cannot be distinguished.
Bei der Reduktion von Verbindungen der allgemeinen For¬ mel (III), in der R3 einen Benzylrest oder R4 einen Ben- zyl- oder tert-Butylrest bedeuten, werden die N-Benzyl- und N-tert-Butylreste reduktiv abgespalten, so daß man Verbindungen der allgemeinen Formel (I) erhält, in der Rl bzw. R2 Wasserstoff statt Benzyl oder tert-Butyl bedeutet.In the reduction of compounds of the general formula (III) in which R3 is a benzyl radical or R4 is a benzyl or tert-butyl radical, the N-benzyl and N-tert-butyl radicals are cleaved reductively, so that Compounds of general formula (I) is obtained in which Rl or R2 is hydrogen instead of benzyl or tert-butyl.
Gegenstand der vorliegenden Patentanmeldung sind ferner neue 3,5-Dibrom-4-nitropyrazol-Derivate der allgemeinen Formel (II)The present patent application also relates to new 3,5-dibromo-4-nitropyrazole derivatives of the general formula (II)
Figure imgf000011_0001
Figure imgf000011_0001
II.
R in der R3 einen Ci- bis C6-Alkylrest, einen C2- bis C4- Hydroxyalkylrest oder einen Benzylrest bedeutet. Bei¬ spiele für Verbindungen der Formel (II) sind 3,5-Di- brom-l-methyl-4-nitropyrazol, 3,5-Dibrom-l-ethyl-4-ni- tropyrazol, 3,5-Dibrom-l-isopropyl-4-nitropyrazol, 3,5- Dibrom-l-(2'-hydroxyethyl)-4-nitropyrazol und 1-Benzyl- 3,5-dibrom-4-nitropyrazol.R in which R3 is a Ci to C6 alkyl radical, a C2 to C4 hydroxyalkyl radical or a benzyl radical. Examples of compounds of the formula (II) are 3,5-dibromo-l-methyl-4-nitropyrazole, 3,5-dibromo-l-ethyl-4-nitropyrazole, 3,5-dibromo-l -isopropyl-4-nitropyrazole, 3,5-dibromo-l- (2'-hydroxyethyl) -4-nitropyrazole and 1-benzyl-3,5-dibromo-4-nitropyrazole.
Ein weiterer Erfindungsgegenstand sind 3-Brom-5-amino- 4-nitropyrazol-Derivate der allgemeinen Formel (III)Another subject of the invention are 3-bromo-5-amino-4-nitropyrazole derivatives of the general formula (III)
Figure imgf000012_0001
Figure imgf000012_0001
in der R3 und R4 unabhängig voneinander einen Ci- bis C6-Alkylrest, C2- bis C4-Hydroxyalkylrest oder einen Benzylrest bedeuten.in which R3 and R4 independently of one another denote a Ci to C6 alkyl radical, C2 to C4 hydroxyalkyl radical or a benzyl radical.
Beispiele für Verbindungen der Formel (III) sindExamples of compounds of the formula (III) are
3-Brom-l-methyl-5-methylamino-4-nitropyrazol,3-bromo-l-methyl-5-methylamino-4-nitropyrazole,
3-Brom-5-(2'-hydroxyethyl)amino-l-methyl-4-nitropyrazol,3-bromo-5- (2'-hydroxyethyl) amino-l-methyl-4-nitropyrazole,
3-Brom-5-tertiärbutylamino-l-methyl-4-nitropyrazol,3-bromo-5-tertiary-butylamino-l-methyl-4-nitropyrazole,
5-Benzylamino-3-brom-l-methyl-4-nitropyrazol,5-benzylamino-3-bromo-l-methyl-4-nitropyrazole,
5-Benzylamino-3-brom-l-ethyl-4-nitropyrazol,5-benzylamino-3-bromo-l-ethyl-4-nitropyrazole,
5-Benzylamino-3-brom-l-isopropyl-4-nitropyrazol,5-benzylamino-3-bromo-l-isopropyl-4-nitropyrazole,
3-Brom-1-(2'-hydroxyethyl)-5-(2 '-hydroxyethyl)amino-4- nitropyrazol, 3-Brom-l-(2'-hydroxyethyl)-5-methylamino-4-nitropyrazol, 5-Benzylamino-3-brom-l-(2'-hydroxyethyl)-4-nitropyrazol l-Benzyl-3-brom-5-methylamino-4-nitropyrazol, l-Benzyl-3-brom-5-ethylamino-4-nitropyrazol, l-Benzyl-3-brom-5-(2'-hydroxyethyl)amino-4-nitropyrazol und l-Benzyl-5-benzylamino-3-brom-4-nitropyrazol zu nen¬ nen sind.3-bromo-1- (2'-hydroxyethyl) -5- (2'-hydroxyethyl) amino-4-nitropyrazole, 3-bromo-1- (2'-hydroxyethyl) -5-methylamino-4-nitropyrazole, 5-benzylamino-3-bromo-1- (2'-hydroxyethyl) -4-nitropyrazole 1-benzyl-3-bromo-5 -methylamino-4-nitropyrazole, l-benzyl-3-bromo-5-ethylamino-4-nitropyrazole, l-benzyl-3-bromo-5- (2'-hydroxyethyl) amino-4-nitropyrazole and l-benzyl-5 -benzylamino-3-bromo-4-nitropyrazole are to be named.
Gegenstand der vorliegenden Erfindung sind ferner neue 4,5-Diaminopyrazol-Derivate der allgemeinen Formel (V)The present invention further relates to new 4,5-diaminopyrazole derivatives of the general formula (V)
Figure imgf000013_0001
I Ra
Figure imgf000013_0001
I Ra
in der Ra und R Wasserstoff, einen Ci- bis Cß-Alkylrest oder einen C2- bis C4-Hydroxyalkylrest bedeuten, mit der Maßgabe, daß, wenn R Wasserstoff ist, Ra nicht Wasser¬ stoff, Methyl oder 2-Hydroxyethyl ist.in which R a and R are hydrogen, a C 1 -C 6 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, with the proviso that when R is hydrogen, R a is not hydrogen, methyl or 2-hydroxyethyl.
Als Beispiele für Verbindungen der Formel (I) werdenAs examples of compounds of formula (I)
4-Amino-l-methyl-5-methylaminopyrazol,4-amino-l-methyl-5-methylaminopyrazole,
4-Amino-5-(2'-hydroxyethyl)amino-1-methylpyrazol,4-amino-5- (2'-hydroxyethyl) amino-1-methylpyrazole,
4,5-Diamino-l-ethylpyrazol,4,5-diamino-l-ethylpyrazole,
4,5-Diamino-l-isopropylpyrazol,4,5-diamino-l-isopropylpyrazole,
4-Amino-l-(2'-hydroxyethyl)-5-(2'-hydroxyethyl)amino- pyrazol, 4-Amino-l-(2'-hydroxyethyl)-5-methylaminopyrazol, 4-Amino-(3)5-methylaminopyrazol, 4-Amino-(3)5-ethylaminopyrazol und 4-Amino-(3)5-(2'-hydroxyethyl)aminopyrazol,4-amino-1- (2'-hydroxyethyl) -5- (2'-hydroxyethyl) amino-pyrazole, 4-amino-1- (2'-hydroxyethyl) -5-methylaminopyrazole, 4-amino- (3) 5-methylaminopyrazole, 4-amino- (3) 5-ethylaminopyrazole and 4-amino- (3) 5- (2 '-hydroxyethyl) aminopyrazole,
genannt.called.
Die Verbindungen der Formel (V) können als Farbstoffvor¬ stufen in Oxidationshaarfärbemitteln zur Färbung von Haaren verwendet werden (siehe Verwendungsbeispiel). The compounds of the formula (V) can be used as dye precursors in oxidation hair colorants for dyeing hair (see example of use).
BeispieleExamples
A) Herstellung von N-substituierten 3 , 5-Dibrom-4-nitro- pyrazolen der allgemeinen Formel ( II )A) Preparation of N-substituted 3, 5-dibromo-4-nitro-pyrazoles of the general formula (II)
a) Allgemeine Vorschrift, Verfahren I:a) General regulation, procedure I:
Zu 1,75 g (70 mmol) Natriumhydrid in 150 ml absolutem DMF (Dimethylformamid) tropft man über einen Zeitraum von 1 Stunde 19,0 g (70 mmol) 3,5-Dibrom-4-nitropyrazol, gelöst in 90 ml absolutem DMF, zu. Nach Beendigung der Gasentwicklung werden 70 mmol Ci bis C6-Alkyl-, C2 bis C4-Hydroxyalkyl- oder Benzylhalogenid in 30 ml DMF zugetropft und 3 Stunden lang auf 80 °C erhitzt. Anschließend destilliert man das Lösungsmittel im Vakuum ab und kristallisiert den Rückstand aus Methylenchlorid um.19.0 g (70 mmol) of 3,5-dibromo-4-nitropyrazole, dissolved in 90 ml of absolute DMF, are added dropwise to 1.75 g (70 mmol) of sodium hydride in 150 ml of absolute DMF (dimethylformamide) over a period of 1 hour , too. After the evolution of gas has ceased, 70 mmol of Ci to C6-alkyl, C2 to C4-hydroxyalkyl or benzyl halide in 30 ml of DMF are added dropwise and the mixture is heated to 80 ° C. for 3 hours. The solvent is then distilled off in vacuo and the residue is recrystallized from methylene chloride.
b) Allgemeine Vorschrift, Verfahren II:b) General regulation, procedure II:
Zu einer Lösung von 5 g (18,5 mmol) 3,5-Dibrom-4- nitropyrazol in 50 ml 2N Natronlauge gibt man 92,5 mmol Ci bis C6-Alkyl-, C2 bis C4-Hydroxy- alkyl- oder Benzylsulfat, läßt 15 Stunden lang bei Raumtemperatur kräftig rühren und filtriert schließlich das ausgefallene Produkt ab, wäscht mit Wasser bis die Waschlösung pH-neutral reagiert und trocknet im Vakuum.92.5 mmol of Ci to C6-alkyl-, C2 to C4-hydroxyalkyl- or benzyl sulfate are added to a solution of 5 g (18.5 mmol) of 3,5-dibromo-4-nitropyrazole in 50 ml of 2N sodium hydroxide solution. is allowed to stir vigorously at room temperature for 15 hours and finally the precipitated product is filtered off, washed with water until the washing solution is pH-neutral and dries in vacuo.
Herstellungsbeispiel 1: 3,5-Dibrom-l-methyl-4-nitro- pyrazolProduction Example 1: 3,5-dibromo-1-methyl-4-nitrophyrazole
Nach Verfahren II erhält man, unter Verwendung von Methylsulfat, 5,06 g (96 Prozent der Theorie) 3,5-Di- brom-l-methyl-4-nitropyrazol in Form weißer Kristalle mit einem Schmelzpunkt von 154 °C.According to method II, using methyl sulfate, 5.06 g (96 percent of theory) of 3,5-di- bromo-l-methyl-4-nitropyrazole in the form of white crystals with a melting point of 154 ° C.
iH-NMR (60 MHz, DMSO-dδ): = 3,90 ppm (s; 3H;-CH3).iH-NMR (60 MHz, DMSO-dδ): = 3.90 ppm (s; 3H; -CH3).
Für diese und alle folgenden lH-NMR-Spektren gilt: DieThe following applies to this and all the following 1H NMR spectra: The
Angaben der chemischen Verschiebung erfolgt in deltaThe chemical shift is given in delta
(ppm), die der Kopplungskonstanten (J) erfolgt in Hertz(ppm), the coupling constant (J) is in Hertz
Standard: Tetramethylsilan s = Singulett, d = Dublett, t = Triplett, q = Quartett, m = Multiplett, Ph = Phenyl, Ring-H = Proton am Pyrazol- ringStandard: tetramethylsilane s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, Ph = phenyl, ring H = proton on the pyrazole ring
MS (70eV) :m/e=287 (M+) .MS (70 eV): m / e = 287 (M + ).
Herstellungsbeispiel 2: 3,5-Dibrom-l-ethyl-4-nitro- pyrazolProduction Example 2: 3,5-dibromo-1-ethyl-4-nitropyrazole
Nach Verfahren II erhält man, unter Verwendung von Ethylsulfat, 3,59 g (65 Prozent der Theorie) 3,5-Dibrom- l-ethyl-4-nitropyrazol in Form weißer Kristalle mit einem Schmelzpunkt von 119 bis 121 °C.According to process II, 3.59 g (65 percent of theory) of 3,5-dibromo-1-ethyl-4-nitropyrazole are obtained in the form of white crystals with a melting point of 119 to 121 ° C. using ethyl sulfate.
iH-NMR (60 MHz, DMSO-d6): = 4,26 (q; J=7,0 Hz; 2H;iH-NMR (60 MHz, DMSO-d6): = 4.26 (q; J = 7.0 Hz; 2H;
-CH2-CH3) und 1,36 ppm (t; J=7,0 Hz; 3H;-CH2~CH3) ■-CH2-CH3) and 1.36 ppm (t; J = 7.0 Hz; 3H; -CH2 ~ CH3) ■
MS (70eV) :m/e=297 (M+) .MS (70 eV): m / e = 297 (M +).
Herstellungsbeispiel 3: 3,5-Dibrom-l-isopropyl-4-nitro- pyrazolProduction Example 3: 3,5-dibromo-l-isopropyl-4-nitro-pyrazole
Nach Verfahren I erhält man, unter Verwendung von 2-Brompropan, 13,14 g (60 Prozent der Theorie) 3,5- Dibrom-l-isopropyl-4-nitropyrazol in Form braungelber Kristalle mit einem Schmelzpunkt von 72 bis 73 °C. iH-NMR (60 MHz, DMSO-d6): = 4,84 (dq; J=6,5 Hz; 1H;Process I gives, using 2-bromopropane, 13.14 g (60 percent of theory) of 3,5-dibromo-l-isopropyl-4-nitropyrazole in the form of brown-yellow crystals with a melting point of 72 to 73 ° C. iH-NMR (60 MHz, DMSO-d6): = 4.84 (dq; J = 6.5 Hz; 1H;
CH) und 1,42 ppm (d; J=6 Hz; 6H;-CH(CH3)2)CH) and 1.42 ppm (d; J = 6 Hz; 6H; -CH (CH3) 2)
MS (70eV) :m/e=311 (M+).MS (70 eV): m / e = 311 (M +).
Herstellungsbeispiel 4: 3,5-Dibrom-l-(2 '-hydroxyethyl)-Production Example 4: 3,5-dibromo-1- (2'-hydroxyethyl) -
4-nitropyrazol4-nitropyrazole
Nach Verfahren I erhält man, unter Verwendung von l-Brom-2-hydroxyethan, 14,77 g (67 Prozent der Theorie) 3,5-Dibrom-l-(2 '-hydroxyethyl)-4-nitropyrazol in Form blaßgelber Kristalle mit einem Schmelzpunkt von 103 bis 105 °C.According to process I, using l-bromo-2-hydroxyethane, 14.77 g (67 percent of theory) of 3,5-dibromo-l- (2'-hydroxyethyl) -4-nitropyrazole are obtained in the form of pale yellow crystals a melting point of 103 to 105 ° C.
iH-NMR (60 MHz, DMSO-d6): = 4,90 (s; breit; 1H; -OH; mit D2O austauschbar), 4,31 (m; 2H; -CH2-) und 4,08-3,82 ppm (m; 2H; -CH2-; nach D2θ-Austausch: t; 2H; J=5 Hz) .iH-NMR (60 MHz, DMSO-d6): = 4.90 (s; broad; 1H; -OH; exchangeable with D2O), 4.31 (m; 2H; -CH2-) and 4.08-3, 82 ppm (m; 2H; -CH2-; after D2θ exchange: t; 2H; J = 5 Hz).
MS (70eV) :m/e=317 (M+) .MS (70 eV): m / e = 317 (M +).
Herstellungsbeispiel 5: l-Benzyl-3,5-dibrom-4-nitro- pyrazolPreparation example 5: 1-benzyl-3,5-dibromo-4-nitro-pyrazole
Nach Verfahren I erhält man, unter Verwendung von Benzylchlorid, 17,94 g (71 Prozent der Theorie) l-Benzyl-3,5-dibrom-4-nitrobenzol in Form blaßgelber Kristalle mit einem Schmelzpunkt von 128 °C.According to process I, 17.94 g (71 percent of theory) of l-benzyl-3,5-dibromo-4-nitrobenzene are obtained in the form of pale yellow crystals with a melting point of 128 ° C. using benzyl chloride.
lH-NMR (60 MHz, DMSO-d6): = 7,26-7,41 (m; 5H; Ph-H) und1 H-NMR (60 MHz, DMSO-d6): = 7.26-7.41 (m; 5H; Ph-H) and
5,51 ppm (s; 2H; -CH2-). MS (70eV) :m/e=363 (M+) . B) Herstellung von 5-Amino-3-brom-4-nitropyrazol- Derivaten der allgemeinen Formel (III)5.51 ppm (s; 2H; -CH2-). MS (70 eV): m / e = 363 (M +). B) Preparation of 5-amino-3-bromo-4-nitropyrazole derivatives of the general formula (III)
Herstellungsbeispiel 6: 3-Brom-l-methyl-5-methylamino-4- nitropyrazolProduction Example 6: 3-bromo-l-methyl-5-methylamino-4-nitropyrazole
2 g (7,02 mmol) 3,5-Dibrom-l-methyl-4-nitropyrazol wer¬ den in 50 ml einer 40 prozentigen Lösung von Methylamin in Ethanol 4 Stunden lang auf Siedetemperatur erhitzt. Nach dem Abkühlen fügt man dem Reaktionsgemisch 100 ml Wasser zu, filtriert das abgeschiedene Produkt ab und wäscht mit wenig Wasser (20 ml). Nach dem Trocknen im Vakuum erhält man 1,45 g (88 Prozent der Theorie) 3-Brom-l-methyl-5-methylamino-4-nitropyrazol in Form gelber Kristalle mit einem Schmelzpunkt von 185 °C.2 g (7.02 mmol) of 3,5-dibromo-l-methyl-4-nitropyrazole are heated to boiling temperature in 50 ml of a 40 percent solution of methylamine in ethanol for 4 hours. After cooling, 100 ml of water are added to the reaction mixture, the separated product is filtered off and washed with a little water (20 ml). After drying in vacuo, 1.45 g (88 percent of theory) of 3-bromo-l-methyl-5-methylamino-4-nitropyrazole are obtained in the form of yellow crystals with a melting point of 185 ° C.
iH-NMR (60 MHz, DMSO-d6): = 7,50 (s; breit; 1H; -NH; mit D2O austauschbar) , 3,88 (s; 3H; N-CH3) und 3,16 ppm (d; 3H; J=6 Hz; -NH-CH3; nach D2O Austausch s).iH-NMR (60 MHz, DMSO-d6): = 7.50 (s; broad; 1H; -NH; exchangeable with D2O), 3.88 (s; 3H; N-CH3) and 3.16 ppm (i.e. ; 3H; J = 6 Hz; -NH-CH3; after D2O exchange s).
MS (70eV) :m/e=236 (M+) .MS (70 eV): m / e = 236 (M + ).
Herstellungsbeispiel 7: 3-Brom-5-(2'-hydroxyethylamino)- l-methyl-4-nitropyrazolProduction Example 7: 3-bromo-5- (2'-hydroxyethylamino) - 1-methyl-4-nitropyrazole
3 g (10,5 mmol) 3,5-Dibrom-l-methyl-4-nitropyrazol wer¬ den in einer Lösung von 30 ml Ethanolamin in 30 ml Etha¬ nol 15 Stunden lang auf Siedetemperatur erhitzt. An¬ schließend gießt man das Reaktionsgemisch auf 200 ml Wasser, filtriert das abgeschiedene Produkt ab, wäscht mit Wasser (20 ml) und trocknet im Vakuum. Aus dem Fil- trat kristallisiert in der Kälte (5 °C) weiteres Produkt aus . Man erhält 2,25 g (81 Prozent der Theorie) 3-Brom-5-(2' hydroxyethyl)amino-l-methyl-4-nitropyrazol in Form geißer Kristalle mit einem Schmelzpunkt von 150 °C.3 g (10.5 mmol) of 3,5-dibromo-l-methyl-4-nitropyrazole are heated to boiling temperature in a solution of 30 ml of ethanolamine in 30 ml of ethanol for 15 hours. The reaction mixture is then poured onto 200 ml of water, the separated product is filtered off, washed with water (20 ml) and dried in vacuo. Further product crystallized out of the filtrate in the cold (5 ° C). 2.25 g (81 percent of theory) of 3-bromo-5- (2 'hydroxyethyl) amino-1-methyl-4-nitropyrazole are obtained in the form of white crystals with a melting point of 150 ° C.
iH-NMR (60 MHz, DMS0-d6): = 7,38 (s; breit; 1H; -NH; mit D2O austauschbar), 4,98 (s; breit; 1H; -OH; mit D2O austauschbar) , 3,82 (s; 3H; N-CH3) und 3,60 ppm (m; 4H; -NH-CH2-CH2) •iH-NMR (60 MHz, DMS0-d6): = 7.38 (s; broad; 1H; -NH; exchangeable with D2O), 4.98 (s; broad; 1H; -OH; exchangeable with D2O), 3 , 82 (s; 3H; N-CH3) and 3.60 ppm (m; 4H; -NH-CH2-CH2) •
MS (70eV) :m/e=266 (M+)MS (70eV): m / e = 266 (M + )
Herstellungsbeispiel 8: 3-Brom-5-tert-butylamino-l- methyl-4-nitropyrazolProduction Example 8: 3-bromo-5-tert-butylamino-1-methyl-4-nitropyrazole
1,5 g (5,26 mmol) 3,5-Dibrom-l-methyl-4-nitropyrazol werden in einer Lösung von 20 ml tert-Butylamin in 30 ml Ethanol 20 Stunden lang auf Siedetemperatur erhitzt.Nach dem Abkühlen gießt man das Reaktionsgemisch auf 150 ml Wasser, filtriert das abgeschiedene Produkt ab und wäscht mit 100 ml Wasser. Nach dem Trocknen im Vakuum erhält man 1,14 g (78 Prozent der Theorie) 3-Brom-5-tert-butylamino-l-methyl-4-nitropyrazol in Form blaßgelber Blättchen mit einem Schmelzpunkt von 75 bis 77 °C.1.5 g (5.26 mmol) of 3,5-dibromo-l-methyl-4-nitropyrazole are heated to boiling temperature in a solution of 20 ml of tert-butylamine in 30 ml of ethanol for 20 hours. After cooling, the mixture is poured Reaction mixture on 150 ml of water, the separated product is filtered off and washed with 100 ml of water. After drying in vacuo, 1.14 g (78 percent of theory) of 3-bromo-5-tert-butylamino-l-methyl-4-nitropyrazole are obtained in the form of pale yellow leaves with a melting point of 75 to 77 ° C.
lH-NMR (60 MHz, DMSO-d6): = 5,35 (s; 1H; -NH; tauscht mit D2O aus), 3,75 (s; 3H; N-CH3) und 1,20 ppm (s; 9H; -C(CH3)3).1 H-NMR (60 MHz, DMSO-d6): = 5.35 (s; 1H; -NH; exchanges with D2O), 3.75 (s; 3H; N-CH3) and 1.20 ppm (s; 9H; -C (CH 3 ) 3 ).
MS (70eV): m/e = 277 (M+) . Herstellungsbeispiel 9: 5-Benzylamino-3-brom-l-methyl-MS (70 eV): m / e = 277 (M + ). Production Example 9: 5-Benzylamino-3-bromo-1-methyl
4-nitropyrazol4-nitropyrazole
2 g (7,02 mmol) 3,5-Dibrom-l-methyl-4-nitropyrazol werden in einer Lösung von 11 g (0,1 mol) Benzylamin in 50 ml Ethanol 10 Stunden lang auf Siedetemperatur er¬ hitzt. Nach dem Abkühlen gießt man das Reaktionsgemisch auf 100 ml Wasser, filtriert das abgeschiedene Produkt ab und wäscht mit Wasser ( 20 ml). Nach dem Trocknen im Vakuum erhält man 1,76 g (81 Prozent der Theorie) 5-Ben- zylamino-3-brom-l-methyl-4-nitropyrazol in Form gelber Nadeln mit einem Schmelzpunkt von 133 °C.2 g (7.02 mmol) of 3,5-dibromo-l-methyl-4-nitropyrazole are heated to boiling temperature in a solution of 11 g (0.1 mol) of benzylamine in 50 ml of ethanol for 10 hours. After cooling, the reaction mixture is poured onto 100 ml of water, the separated product is filtered off and washed with water (20 ml). After drying in vacuo, 1.76 g (81 percent of theory) of 5-benzylamino-3-bromo-1-methyl-4-nitropyrazole are obtained in the form of yellow needles with a melting point of 133 ° C.
iH-NMR (60 MHz, DMSO-d6): = 7,88 (t; 1H; J = 6Hz;-NH; mit D2O austauschbar), 7,32 (m; 5H; Ph-H) , 4,73 (d; 2H; J = 6 Hz; -NH-CH2-; nach D2θ-Austausch s) und 3,68 ppm (s; 3H; N-CH3).iH-NMR (60 MHz, DMSO-d6): = 7.88 (t; 1H; J = 6Hz; -NH; exchangeable with D2O), 7.32 (m; 5H; Ph-H), 4.73 ( d; 2H; J = 6 Hz; -NH-CH2-; after D2θ exchange s) and 3.68 ppm (s; 3H; N-CH3).
MS (70eV): m/e = 312 (M+).MS (70 eV): m / e = 312 (M + ).
Herstellungsbeispiel 10: 5-Benzylamino-3-brom-l-ethyl-Production Example 10: 5-Benzylamino-3-bromo-1-ethyl
4-nitropyrazol4-nitropyrazole
6,3 g (21 mmol) 3,5-Dibrom-l-ethyl-4-nitropyrazol werden in 10 ml Benzylamin 1 Stunde lang auf 80 °C erhitzt. An¬ schließend gießt man das Reaktionsgemisch auf 50 ml Wasser und trennt das abgeschiedene Öl ab, aus dem, nach Zugabe von 20 bis 30 ml Essigsäureethylester, das Pro¬ dukt auskristallisiert. Nach einmaligem Umkristalli¬ sieren aus Methanol erhält man 5,2 g (76 Prozent der Theorie) 5-Benzylamino-3-brom-l-ethyl-4-nitropyrazol in Form hellgelber Nadeln mit einem Schmelzpunkt von 92 CC. iH-NMR (300 MHz,DMSO-d6) : = 7,90 (t; J = 6,7Hz; 1H;-NH; tauscht mit D2O aus), 7,26- 7,40 (m; 5H; Ph-H) , 4,68 (d; J = 6,7 Hz,2H; NH-CH?-; nach D2θ-Austausch s), 4,00 (q; J = 7,3Hz; 2H; -CH2-CH3) , und 1,18 ppm (t; J = 7,2Hz; 3H; -CH2-CH3) .6.3 g (21 mmol) of 3,5-dibromo-1-ethyl-4-nitropyrazole are heated to 80 ° C. in 10 ml of benzylamine for 1 hour. The reaction mixture is then poured onto 50 ml of water and the separated oil is separated off, from which, after addition of 20 to 30 ml of ethyl acetate, the product crystallizes out. After one Umkristalli¬ Sieren from methanol obtained 5.2 g (76 percent of theory) of 5-benzylamino-3-bromo-l-ethyl-4-nitropyrazole in the form of light yellow needles having a melting point of 92 C C. iH-NMR (300 MHz, DMSO-d6): = 7.90 (t; J = 6.7Hz; 1H; -NH; exchanges with D2O), 7.26- 7.40 (m; 5H; Ph- H), 4.68 (d; J = 6.7 Hz, 2H; NH-CH? -; after D2θ exchange s), 4.00 (q; J = 7.3 Hz; 2H; -CH2-CH3) , and 1.18 ppm (t; J = 7.2Hz; 3H; -CH2-CH3).
MS (70 eV) : m/e = 324 (M+)MS (70 eV): m / e = 324 (M + )
Herstellungsbeispiel 11: 5-Benzylamino-3-brom-l-isopro- pyl-4-nitropyrazolProduction Example 11: 5-Benzylamino-3-bromo-1-isopropyl-4-nitropyrazole
3,13 g (10 mmol) 3,5-Dibrom-l-isopropyl-4-nitropyrazol werden in 10 ml Benzylamin 1 Stunde lang auf 80 °C er¬ hitzt. Anschließend gießt man das Reaktionsgemisch' auf 50 ml Wasser und filtriert das abgeschiedene Produkt ab. Nach einmaligem Umkristallisieren aus einem Toluol/ Petrolether-Gemisch (1:1) erhält man 2,3 g (68 Prozent der Theorie) 5-Benzylamino-3-brom-l-isopropyl-4-nitro- pyrazol in Form hellgelber Kristalle mit einem Schmelzpunkt von 120 und 122 °C.3.13 g (10 mmol) of 3,5-dibromo-l-isopropyl-4-nitropyrazole are heated in 80 ml of benzylamine at 80 ° C. for 1 hour. The reaction mixture is then poured onto 50 ml of water and the separated product is filtered off. After recrystallization once from a toluene / petroleum ether mixture (1: 1), 2.3 g (68 percent of theory) of 5-benzylamino-3-bromo-l-isopropyl-4-nitro-pyrazole in the form of light yellow crystals with a Melting point of 120 and 122 ° C.
iH-NMR (300 MHz,DMSO-d6) : = 7,78 (t; J = 6,6Hz; 1H;-NH; nach D2θ-Austausch s), 7,25-7,39 (m; 5H; Ph-H); 4,66 (d; J = 6,6Hz; 2H,-NH- CH2-; nach D2θ-Austausch s) ; 4,57 (dq; J = 6,4Hz; 1H; -CH(CH3)2) und 1,19 ppm (d; J = 6,4Hz; 6H: -CH(CH3)2).iH-NMR (300 MHz, DMSO-d6): = 7.78 (t; J = 6.6Hz; 1H; -NH; after D2θ exchange s), 7.25-7.39 (m; 5H; Ph -H); 4.66 (d; J = 6.6Hz; 2H, -NH-CH2-; after D2θ exchange s); 4.57 (dq; J = 6.4Hz; 1H; -CH (CH3) 2) and 1.19 ppm (d; J = 6.4Hz; 6H: -CH (CH3) 2).
MS (70 eV) : m/e = 338 (M+) Herstellungsbeispiel 12: 3-Brom-l-(2 '-hydroxyethyl)-5-MS (70 eV): m / e = 338 (M +) Production Example 12: 3-bromo-1- (2'-hydroxyethyl) -5-
(2 '-hydroxyethyl)amino-4-nitro- pyrazol(2'-Hydroxyethyl) amino-4-nitropyrazole
1,5 g (4,8 mmol) 3,5-Dibrom-l-(2 '-hydroxyethyl )-4-nitro- pyrazol werden in einer Lösung von 0,58 g (9,6 mmol) Ethanolamin in 30 ml Ethanol 15 Stunden lang auf 80 °C erhitzt. Nach dem Abkühlen fügt man dem Reaktionsgemisch 50 ml Wasser zu und extrahiert drei mal mit je 70 ml Essigsäureethylester. Man gibt zu den vereinigten Ex¬ traktionslösungen 200 ml n-Hexan und destilliert das Lösungsmittelgemisch im Vakuum auf ein Drittel der ur¬ sprünglichen Menge ab. Danach fügt man erneut n-Hexan bis zur Trübung der Lösung zu. Anschließend filtriert man das auskristallisierte Produkt ab und wäscht mit n-Hexan (10 bis 20 ml). Man erhält 1,04 g (74 Prozent der Theorie) 3-Brom-,l-(2 '-hydroxyethyl)-5-(2 '-hy¬ droxyethyl)amino-4-nitropyrazol in Form hellgelber Kristalle mit einem Schmelzpunkt von 132 bis 134 °C.1.5 g (4.8 mmol) of 3,5-dibromo-l- (2 '-hydroxyethyl) -4-nitro-pyrazole are dissolved in a solution of 0.58 g (9.6 mmol) of ethanolamine in 30 ml of ethanol Heated to 80 ° C for 15 hours. After cooling, 50 ml of water are added to the reaction mixture and extracted three times with 70 ml of ethyl acetate each time. 200 ml of n-hexane are added to the combined extraction solutions and the solvent mixture is distilled off in vacuo to a third of the original amount. Then add n-hexane again until the solution becomes cloudy. The product which has crystallized out is then filtered off and washed with n-hexane (10 to 20 ml). 1.04 g (74 percent of theory) of 3-bromo, l- (2 '-hydroxyethyl) -5- (2' -hydroxyethyl) amino-4-nitropyrazole are obtained in the form of pale yellow crystals with a melting point of 132 up to 134 ° C.
iH-NMR (60 MHz, DMSO-dß): = 7,42 (s; breit; 1H; -NH; mit D2O austauschbar) , 5,23-5,02 (m; 2H; -OH; mit D2O austauschbar), 4,18 (m; 2H; N-CH2-) und 3,93- 3,45 ppm ( ; 6H; -CH2-).iH-NMR (60 MHz, DMSO-dß): = 7.42 (s; broad; 1H; -NH; exchangeable with D2O), 5.23-5.02 (m; 2H; -OH; exchangeable with D2O) , 4.18 (m; 2H; N-CH2-) and 3.93-3.45 ppm (; 6H; -CH2-).
MS (70 eV) : m/e = 296 (M+) MS (70 eV): m / e = 296 (M +)
Herstellungsbeispiel 13: 3-Brom-l-(2 '-hydroxyethyl)-5- methylamino-4-nitropyrazolProduction Example 13: 3-bromo-1- (2'-hydroxyethyl) -5-methylamino-4-nitropyrazole
3,15 g (10 mmol) 3,5-Dibrom-l-(2 '-hydroxyethyl)-4-nitro- pyrazol werden in 70 ml einer 30prozentigen Lösung von Methylamin in Wasser 1 Stunde lang auf 60 °C erwärmt. Nach dem Abkühlen fällt das Produkt in Form hellgelber Kristalle, mit einem Schmelzpunkt von 158 bis 160 °C, aus. Man erhält 2,4 g (91 Prozent der Theorie) 3-Brom-l-(2 'hydroxyethyl)-5-methylamino-4-nitropyrazol.3.15 g (10 mmol) of 3,5-dibromo-l- (2 '-hydroxyethyl) -4-nitro-pyrazole are heated to 60 ° C. for 1 hour in 70 ml of a 30 percent solution of methylamine in water. After cooling, the product precipitates in the form of light yellow crystals with a melting point of 158 to 160 ° C. 2.4 g (91 percent of theory) of 3-bromo-1- (2 'hydroxyethyl) -5-methylamino-4-nitropyrazole are obtained.
iH-NMR (300 MHz DMSO-d6): = 7,67 (s; 1H; -NH; tauscht mit D2O aus); 5,06 (s; 1H; -OH; tauscht mit D2O aus), 4,18 (t; 2H; N-CH2-), 3,68 (t; 2H;-CH2-OH) und 3,15 ppm (d; J = 4,5 Hz; 3H;-NH- CH3; nach D2θ-Austausch s).iH-NMR (300 MHz DMSO-d6): = 7.67 (s; 1H; -NH; exchanges with D2O); 5.06 (s; 1H; -OH; exchanges with D2O), 4.18 (t; 2H; N-CH2-), 3.68 (t; 2H; -CH2-OH) and 3.15 ppm ( d; J = 4.5 Hz; 3H; -NH-CH3; after D2θ exchange s).
MS (70 eV) : m/e = 266 (M+) .MS (70 eV): m / e = 266 (M + ).
Herstellungsbeispiel 14: 5-Benzylamino-3-brom-l-(2 '-hy¬ droxyethyl)-4-nitropyrazolPreparation example 14: 5-benzylamino-3-bromo-1- (2'-hydroxyethyl) -4-nitropyrazole
6,3 g (20 mmol) 3,5-Dibrom-l-(2 '-hydroxyethyl)-4-nitro- pyrazol werden in 20 ml Benzylamin 2 Stunden lang auf 60 °C erhitzt. Nach dem Abkühlen gießt man auf 50 ml Wasser, filtriert das abgeschiedene Produkt ab und kristallisiert einmal aus Toluol/Ligroin (1:1) um. Man erhält 4 g (59 Prozent der Theorie) 5-Benzylamino-3- brom-l-(2 '-hydroxyethyl)-4-nitropyrazol in Form gelber Kristalle mit einem Schmelzpunkt von 133 bis 135 °C. iH-NMR (300 MHz,DMSO-d6) : = 7,89 (t; J = 6,6Hz; 1H;-NH; tauscht mit D2O aus), 7,22- 7,44 (m; 5H; Ph-H); 5,15 (s; 1H;-0H; tauscht mit D2O aus) , 4,77 (d; J = 6,6Hz; 2H;-NH-CH2-; nach D2O-AUS- tausch s), 3,99 (t; J = 4,9H; 2H;-CH2-) und 3,96 ppm (t; J = 5Hz; 2H;-CH2~).6.3 g (20 mmol) of 3,5-dibromo-l- (2'-hydroxyethyl) -4-nitro-pyrazole are heated in 60 ml of benzylamine at 60 ° C for 2 hours. After cooling, the mixture is poured onto 50 ml of water, the separated product is filtered off and recrystallized once from toluene / ligroin (1: 1). 4 g (59 percent of theory) of 5-benzylamino-3-bromo-l- (2'-hydroxyethyl) -4-nitropyrazole are obtained in the form of yellow crystals with a melting point of 133 to 135 ° C. iH-NMR (300 MHz, DMSO-d6): = 7.89 (t; J = 6.6Hz; 1H; -NH; exchanges with D2O), 7.22- 7.44 (m; 5H; Ph- H); 5.15 (s; 1H; -0H; exchanges with D2O), 4.77 (d; J = 6.6Hz; 2H; -NH-CH2-; after D2O exchange s), 3.99 ( t; J = 4.9H; 2H; -CH2-) and 3.96 ppm (t; J = 5Hz; 2H; -CH2 ~).
MS (70 eV) : m/e = 340 (M+)MS (70 eV): m / e = 340 (M + )
Herstellungsbeispiel 15 : l-Benzyl-3-brom-5-methylaπtino-Production Example 15: 1-Benzyl-3-bromo-5-methylaπtino
4-nitropyrazol4-nitropyrazole
3,61 g (10 mmol) l-Benzyl-3,5-dibrom-4-nitropyrazol werden in 100 ml einer 35prozentigen Lösung von Metyl- amin in Wasser 4 Stunden lang auf 60 °C erhitzt. Nach dem Abkühlen filtriert man den abgeschiedenen Nieder¬ schlag ab und kristallisiert einmal aus Ethanol um. Man erhält 2,7 g (87 Prozent der Theorie) 1-Benzyl- 3-brom-5-methylamino-4-nitropyrazol in Form farbloser Kristalle mit einem Schmelzpunkt von 116 °C.3.61 g (10 mmol) of l-benzyl-3,5-dibromo-4-nitropyrazole are heated in 100 ml of a 35 percent solution of methylamine in water at 60 ° C. for 4 hours. After cooling, the deposited precipitate is filtered off and recrystallized once from ethanol. 2.7 g (87 percent of theory) of 1-benzyl-3-bromo-5-methylamino-4-nitropyrazole are obtained in the form of colorless crystals with a melting point of 116 ° C.
iH-NMR (300 MHz,DMSO-dß) : = 7,71 (s; 1H; -NH; tauscht mit D2O aus), 7,15-7,40 (m;iH-NMR (300 MHz, DMSO-dß): = 7.71 (s; 1H; -NH; exchanges with D2O), 7.15-7.40 (m;
5H, Ph-H), 5,45 (s; 2H;5H, Ph-H), 5.45 (s; 2H;
-CH2-) und 3,02 ppm (s; 3H;-CH2-) and 3.02 ppm (s; 3H;
-CH3). MS (70 eV) : m/e = 312 (M+) . Herstellungsbeispiel 16: l-Benzyl-3-brom-5-ethylamino--CH 3 ). MS (70 eV): m / e = 312 (M + ). Production Example 16: 1-Benzyl-3-bromo-5-ethylamino
4-nitropyrazol4-nitropyrazole
3,61 (10 mmol) l-Benzyl-3,5-dibrom-4-nitropyrazol werden in 120 ml einer 30prozentigen wäßrigen Ethylaminlösung 1 Stunde lang auf 60 °C erhitzt. Nach dem Abkühlen scheidet sich das Produkt in Form farbloser Kristalle mit einem Schmelzpunkt von 122 °C ab. Man erhält 2,88 g 89 Prozent der Theorie) l-Benzyl-3-brom-5-ethylamino-4- nitropyrazol.3.61 (10 mmol) l-benzyl-3,5-dibromo-4-nitropyrazole are heated in 120 ml of a 30 percent aqueous ethylamine solution at 60 ° C. for 1 hour. After cooling, the product separates in the form of colorless crystals with a melting point of 122 ° C. 2.88 g (89 percent of theory) of l-benzyl-3-bromo-5-ethylamino-4-nitropyrazole are obtained.
iH-NMR (300 MHz,DMS0-d6) : = 7,15-7,41 (m; 6H; -NH undiH-NMR (300 MHz, DMS0-d6): = 7.15-7.41 (m; 6H; -NH and
Ph-H; 1H tauscht mit D2O aus), 5,37 (s; 1H; -CH2-), 3,32-3,39 (m; 2H; -CH2-CH3) und 1,07-1,12 ppm (t; 3H;- CH2-CH3).Ph-H; 1H exchanges with D2O), 5.37 (s; 1H; -CH2-), 3.32-3.39 (m; 2H; -CH2-CH3) and 1.07-1.12 ppm (t; 3H ; - CH2-CH3).
MS (70 eV) : m/e = 326 (M+)MS (70 eV): m / e = 326 (M + )
Herstellungsbeispiel 17: l-Benzyl-3-brom-5-(2'-hydroxy¬ ethyl)amino-4-nitropyrazolProduction Example 17: 1-Benzyl-3-bromo-5- (2'-hydroxyethyl) amino-4-nitropyrazole
3,61 g (10 mmol) l-Benzyl-3,5-dibrom-4-nitropyrazol werden in 15 ml Ethanolamin 2 Stunden lang auf 80 °C erhitzt. Nach dem Abkühlen gießt man das Reaktionsge¬ misch auf 30 ml Wasser und filtriert den abgeschiedenen Niederschlag ab. Nach einmaligem Umkristallisieren aus Toluol erhält man 2,5 g (74 Prozent der Theorie) l-Benzyl-3-brom-5-(2 '-hydroxyethyl)amino-4-nitropyrazol in Form blaßgelber Kristalle mit einem Schmelzpunkt von 110 bis 112 °C. iH-NMR (300 MHz,DMSO-d6) : = 7,54 (t; 1H; -NH; tauscht mit D20 aus), 7,15-7,40 (m; 5H; Ph-H), 5,44 (s; 2H; -CH2-Ph) , 5,05 (t; 1H;-0H; tauscht mit D2O aus) und 3,32-3,53 ppm (m; 4H;-CH2~ CH2-).3.61 g (10 mmol) of l-benzyl-3,5-dibromo-4-nitropyrazole are heated to 80 ° C. in 15 ml of ethanolamine for 2 hours. After cooling, the reaction mixture is poured onto 30 ml of water and the deposited precipitate is filtered off. After recrystallization from toluene once, 2.5 g (74 percent of theory) of l-benzyl-3-bromo-5- (2'-hydroxyethyl) amino-4-nitropyrazole are obtained in the form of pale yellow crystals with a melting point of 110 to 112 ° C. iH-NMR (300 MHz, DMSO-d6): = 7.54 (t; 1H; -NH; exchanges with D20), 7.15-7.40 (m; 5H; Ph-H), 5.44 (s; 2H; -CH2-Ph), 5.05 (t; 1H; -0H; exchanges with D2O) and 3.32-3.53 ppm (m; 4H; -CH2 ~ CH 2 -).
MS (70 eV) : m/e = 342 (M+) .MS (70 eV): m / e = 342 (M + ).
Herstellungsbeispiel 18: l-Benzyl-5-benzylamino-3-brom-Production Example 18: 1-Benzyl-5-benzylamino-3-bromo
4-nitropyrazol4-nitropyrazole
3,61 g (10 mmol) l-Benzyl-3,5-dibrom-4-nitropyrazol wer¬ den in einer Lösung von 3,6 g Benzylamin 2 Stunden lang auf 60 °C erhitzt. Nach dem Abkühlen wird das Reaktions¬ gemisch auf 20 ml Wasser gegossen und der abgeschiedene Niederschlag abfiltriert. Nach einmaligem Umkristalli¬ sieren aus einem Ligroin/Toluol-Gemisch (1:1) erhält man 2,6 g (68 Prozent der Theorie) l-Benzyl-5-benzyl- amino-3-brom-4-nitropyrazol in Form blaßgelber Kristalle mit einem Schmelzpunkt von 103 °C.3.61 g (10 mmol) of l-benzyl-3,5-dibromo-4-nitropyrazole are heated in a solution of 3.6 g of benzylamine at 60 ° C. for 2 hours. After cooling, the reaction mixture is poured onto 20 ml of water and the deposited precipitate is filtered off. After single recrystallization from a ligroin / toluene mixture (1: 1), 2.6 g (68 percent of theory) of l-benzyl-5-benzylamino-3-bromo-4-nitropyrazole are obtained in the form of pale yellow crystals with a melting point of 103 ° C.
iH-NMR (300 MHz,DMSO-dß) : = 8,04 (t; J = 6,1Hz; 1H;-NH; tauscht mit D2O aus), 7,08- 7,47 (m; 10H; Ph-H), 5,24 (s; 2H; -CH2_-Ph) und 4,55 ppm (d; J = 6,1Hz; 2H; -NH- CH2-Ph; nach D2θ-Austausch s).iH-NMR (300 MHz, DMSO-dß): = 8.04 (t; J = 6.1Hz; 1H; -NH; exchanges with D2O), 7.08- 7.47 (m; 10H; Ph- H), 5.24 (s; 2H; -CH2_-Ph) and 4.55 ppm (d; J = 6.1Hz; 2H; -NH-CH2-Ph; after D2θ exchange s).
MS (70 eV) : m/e = 388 (M+) C) Herstellung von 4,5-Diaminopyrazol-Derivaten der allgemeinen Formel (I)MS (70 eV): m / e = 388 (M +) C) Preparation of 4,5-diaminopyrazole derivatives of the general formula (I)
a) Allgemeine Vorschrift, Verfahren (1):a) General regulation, procedure (1):
Eine in den folgenden Herstellungsbeispielen angege¬ bene Menge einer Verbindung der allgemeinen FormelAn amount of a compound of the general formula given in the following preparation examples
(II) wird in 130 ml Ethanol gelöst und in einen Au¬ toklaven (250 ml) überführt. Nach der Zugabe von 2 Spatelspitzen (ca. 100 mg) eines Palladium/Aktiv¬ kohle-Katalysators, mit einem Polladiumanteil von 10 Gewichtsprozent, wird über den in den nachfolgenden Herstellungsbeispielen angegebenen Zeitraum, bei 50 bar Wasserstoffatmosphäre, bei Raumtemperatur ge¬ rührt. Anschließend wird die Reaktionsmischung mit¬ tels einer Wasserstrahlpumpe in einen Glaskolben überführt und der Katalysator sofort über einen Glasfiltertiegel abfiltriert. Danach fügt man dem Filtrat eine zur Ausgangsverbingung äquimolare Menge Schwefelsäure (97prozentig) oder die zweifachmolare Menge Salzsäure (36prozentig) zu.(II) is dissolved in 130 ml of ethanol and transferred to an autoclave (250 ml). After the addition of 2 spatula tips (approx. 100 mg) of a palladium / activated carbon catalyst with a polladium content of 10 percent by weight, the mixture is stirred at room temperature at 50 bar hydrogen atmosphere for the period specified in the following production examples. The reaction mixture is then transferred into a glass flask by means of a water jet pump and the catalyst is immediately filtered off through a glass filter crucible. Then one adds to the filtrate an equimolar amount of sulfuric acid (97 percent) to the starting compound or the double molar amount of hydrochloric acid (36 percent).
b) Allgemeine Vorschrift, Verfahren (2):b) General regulation, procedure (2):
Eine in den folgenden Herstellungsbeispielen angege¬ bene Menge einer Verbindung der allgemeinen FormelAn amount of a compound of the general formula given in the following preparation examples
(III) wird in einem Hydrierkolben mit einer äquimo- laren Menge 97prozentiger Schwefelsäure, 2 Spatel¬ spitzen Palladium/Aktivkohle-Katalysator (10 Ge¬ wichtsprozent Palladium) und der jeweils angegebenen Menge Wasser bei Raumtemperatur unter Wasserstoff¬ atmosphäre (Normaldruck) über den in den nachfol¬ genden Herstellungsbeispielen angegebenen Zeitraum geschüttelt. Der Reaktionsverlauf wird mittels Dünnschichtchromatographie kontrolliert. Nach vollständiger Umsetzung des Eduktes wird das Reak- tionsgemisch über einen Glasfiltertiegel abfiltriert. Nach dem Abdestillieren des Lösungsmittels wird das Produkt aus Ethanol kristallisiert.(III) is in a hydrogenation flask with an equimolar amount of 97 percent sulfuric acid, 2 spatula tips palladium / activated carbon catalyst (10 percent by weight palladium) and the amount of water indicated at room temperature under hydrogen atmosphere (normal pressure) over the in the period specified in the following production examples. The course of the reaction is checked by means of thin layer chromatography. After the starting material has been completely converted, the react tion mixture filtered through a glass filter crucible. After the solvent has been distilled off, the product is crystallized from ethanol.
Herstellungsbeispiel 19: 4-Amino-l-methyl-5-methylamino- pyrazolProduction Example 19: 4-Amino-1-methyl-5-methylamino-pyrazole
0,5 g (2,13 mmol) 3-Brom-l-methyl-5-methylamino-4-nitro- pyrazol werden in einer Lösung von 220 mg (2,13 mmol) Schwefelsäure in 20 ml Wasser, nach Zugabe des Katalysa¬ tors, 14 Stunden lang, wie in Verfahren (2) beschrieben, hydriert. Nach dem Abfiltrieren des Katalysators engt man das Filtrat bis zur Trockene ein und kristallisiert den Rückstand aus Ethanol um. Man erhält 370 mg (78 Prozent der Theorie) 4-Amino-l-methyl-5-methylaminopy- razol-hydrosulfat in Form farbloser Kristalle mit einem Schmelzpunkt von 185 bis 188 °C.0.5 g (2.13 mmol) of 3-bromo-l-methyl-5-methylamino-4-nitro-pyrazole are in a solution of 220 mg (2.13 mmol) of sulfuric acid in 20 ml of water, after adding the catalyst ¬ tors, hydrogenated for 14 hours as described in process (2). After filtering off the catalyst, the filtrate is concentrated to dryness and the residue is recrystallized from ethanol. 370 mg (78 percent of theory) of 4-amino-1-methyl-5-methylaminopyrazole hydrosulfate are obtained in the form of colorless crystals with a melting point of 185 to 188 ° C.
iH-NMR (60 MHz, DMSO-d6): = 8,53 (s; breit; 5H, -NH2;iH-NMR (60 MHz, DMSO-d6): = 8.53 (s; broad; 5H, -NH2;
-NH; H2SO4; mit D2O aus¬ tauschbar), 7,30 (s; 1H; Ring-H 3,58 (s; 3H; N-CH3) und 2,80 ppm (s; 3H; -NH-CH3) .-NH; H2SO4; exchangeable with D2O), 7.30 (s; 1H; Ring-H 3.58 (s; 3H; N-CH3) and 2.80 ppm (s; 3H; -NH-CH3).
MS (70 eV) : m/e = 126 (M+) .MS (70 eV): m / e = 126 (M + ).
Herstellungsbeispiel 20: 4-Amino-5-(2'-hydroxyethyl)ami- no-1-methylpyrazolPreparation example 20: 4-amino-5- (2'-hydroxyethyl) amino-1-methylpyrazole
1 g (3,77 mmol) 3-Brom-5-(2 '-hydroxyethyl)amino-1-me- thyl-4-nitropyrazol werden in einer Lösung von 380 mg (3,77 mmol) Schwefelsäure in 50 ml Wasser 2 Stunden lang nach Verfahren (2) hydriert. Man erhält 720 mg (75 Pro¬ zent der Theorie) 4-Amino-5-(2 '-hydroxyethyl)amino-l-me- thylpyrazol-hydrosulfat in Form farbloser Kristalle mit einem Schmelzpunkt von 94 bis 97 °C.1 g (3.77 mmol) of 3-bromo-5- (2'-hydroxyethyl) amino-1-methyl-4-nitropyrazole are dissolved in a solution of 380 mg (3.77 mmol) of sulfuric acid in 50 ml of water 2 Hydrogenated for hours according to method (2). 720 mg (75 percent of theory) of 4-amino-5- (2'-hydroxyethyl) amino-l-me- thylpyrazole hydrosulfate in the form of colorless crystals with a melting point of 94 to 97 ° C.
iH-NMR (60 MHz, DMS0-d6): = 8,00 (s; breit; 6H; -NH2 ;iH-NMR (60 MHz, DMS0-d6): = 8.00 (s; broad; 6H; -NH2;
-NH,-0H, H2SO4, tauscht mit-NH, -0H, H2SO4, exchange
D2O aus) , 7,45 (s; 1H;D2O off), 7.45 (s; 1H;
Ring-H), 3,60 (s; 3H;Ring-H), 3.60 (s; 3H;
-CH3) und 3,50-3,10 (m; 4H;-CH3) and 3.50-3.10 (m; 4H;
-CH2-CH2-) • MS (70 eV) : m/e = 156 (M+).-CH2-CH2-) • MS (70 eV): m / e = 156 (M +).
Herstellungsbeispiel 21: 4,5-Diamino-l-methylpyrazolPreparation 21: 4,5-diamino-l-methylpyrazole
a) 0,5 g (1,81 mmol) 3-Brom-5-tert-butylamino-l-me- thyl-4-nitropyrazol werden in einer Lösung von 1,84 mg (1,81 mmol) Schwefelsäure in 20 ml Wasser, nach Zugabe des Katalysators, 48 Stunden lang nach Ver¬ fahren (2) hydriert. Man erhält, nach Abdestillieren des Lösungsmittels auf die Hälfte der ursprünglichen Menge und Zugabe einer äquivalenten Menge Ethanol, 360 mg (87 Prozent der Theorie) 4,5-Diamino-l-me- thylpyrazol-hydrosulfat-hydrat in Form von weißen Kristallen mit einem Schmelzpunkt von 200 bisa) 0.5 g (1.81 mmol) of 3-bromo-5-tert-butylamino-1-methyl-4-nitropyrazole are dissolved in a solution of 1.84 mg (1.81 mmol) of sulfuric acid in 20 ml Water, after addition of the catalyst, is hydrogenated for 48 hours after process (2). After distilling off the solvent to half the original amount and adding an equivalent amount of ethanol, 360 mg (87 percent of theory) of 4,5-diamino-l-methylpyrazole hydrosulfate hydrate are obtained in the form of white crystals with a Melting point from 200 to
201 °C.201 ° C.
b) 0,5 g (1,61 mmol) 5-Benzylamino-3-brom-l-methyl4-ni- tropyrazol werden in einer Lösung von 165 mg (161 mmol) Schwefelsäure in 20 ml Wasser, nach Zugabe des Katalysators, 48 Stunden lang, wie im Verfahren (2) beschrieben, hydriert. Anschließend filtriert man den Katalysator ab und engt das Filtrat auf ca. 2 ml ein. Nach Zugabe von wenig Ethanol (ca. 2 ml) schei¬ det sich das Produkt in Form weißer Kristalle ab. Man erhält 330 mg (90 Prozent der Theorie) 4,5-Dia- mino-1-methylpyrazol-hydrosulfat-hydrat in Form von weißen Kristallen mit einem Schmelzpunkt von 200 bis 201 °C.b) 0.5 g (1.61 mmol) of 5-benzylamino-3-bromo-l-methyl4-nitropyrazole are dissolved in a solution of 165 mg (161 mmol) of sulfuric acid in 20 ml of water, after adding the catalyst, 48 Hydrogenated for hours as described in process (2). The catalyst is then filtered off and the filtrate is concentrated to about 2 ml. After adding a little ethanol (approx. 2 ml), the product separates out in the form of white crystals. 330 mg (90 percent of theory) of 4,5-slide mino-1-methylpyrazole hydrosulfate hydrate in the form of white crystals with a melting point of 200 to 201 ° C.
Herstellungsbeispiel 22: 4,5-Diamino-l-ethylpyrazolPreparation 22: 4,5-diamino-l-ethylpyrazole
1,62 g (5,6 mmol) 3-Benzylamino-3-brom-l-ethyl-4-nitro- pyrazol werden über einen Zeitraum von 2 Stunden nach Vorschrift (1) hydriert. Nach Abfiltrieren des Katalysa¬ tors fällt man durch Zugabe von 1 ml (11,6 mmol) konzen¬ trierter Salzsäure (36prozentig) das Produkt als Dihy- drochlorid aus. Man erhält 0,8 g (72 Prozent der Theo¬ rie) 4,5-Diamino-l-ethylpyrazol-dihydrochlorid in Form farbloser Kristalle mit einem Schmelzpunkt von 184 bis 186 °C.1.62 g (5.6 mmol) of 3-benzylamino-3-bromo-1-ethyl-4-nitrophyrazole are hydrogenated over a period of 2 hours according to procedure (1). After filtering off the catalyst, the product is precipitated as dihydrochloride by adding 1 ml (11.6 mmol) of concentrated hydrochloric acid (36 percent). 0.8 g (72 percent of theory) of 4,5-diamino-1-ethylpyrazole dihydrochloride are obtained in the form of colorless crystals with a melting point of 184 to 186 ° C.
iH-NMR (300 MHz,DMSO-d6) : = 8,01 (s; breit; 6H;-NH2;iH-NMR (300 MHz, DMSO-d6): = 8.01 (s; broad; 6H; -NH2;
HC1; tauscht mit D2O aus), 7,63 (s; 1H; Ring-H; 4,03 (q; J = 6,4 Hz; 2H;-CH2_- CH3) und 1,25 ppm (t; J = 6,5 Hz; 3H; -CH2-CH3) .HC1; exchanges with D2O), 7.63 (s; 1H; Ring-H; 4.03 (q; J = 6.4 Hz; 2H; -CH2_- CH3) and 1.25 ppm (t; J = 6, 5 Hz; 3H; -CH2-CH3).
MS (70 eV) : m/e = 126 (M+)MS (70 eV): m / e = 126 (M + )
Herstellungsbeispiel 23: 4,5-Diamino-l-isopropylpyrazolPreparation 23: 4,5-diamino-l-isopropylpyrazole
0,5 g (1,6 mmol) l-Benzylamino-3-brom-l-isopropyl-4-ni- tropyrazol werden 2 Stunden lang nach Vorschrift ( 1 ) hydriert. Nach Abfiltrieren des Katalysators wird das Produkt mit 0,3 ml (3,5 mmol) konzentrierter Salzsäure als Dihydrochlorid ausgefällt. Man erhält 0,25 g (73 Prozent der Theorie) 4,5-Diamino-l-isopropylpyrazol- dihydrochlorid in Form farbloser Kristalle mit einem Schmelzpunkt von 164 °C. iH-NMR (300 MHz,DMSO-d6) : = 7,90 (s; breit; 6H; -NH2;0.5 g (1.6 mmol) of 1-benzylamino-3-bromo-1-isopropyl-4-nitropyrazole are hydrogenated for 2 hours according to procedure (1). After filtering off the catalyst, the product is precipitated with 0.3 ml (3.5 mmol) of concentrated hydrochloric acid as dihydrochloride. 0.25 g (73 percent of theory) of 4,5-diamino-l-isopropylpyrazole dihydrochloride are obtained in the form of colorless crystals with a melting point of 164 ° C. iH-NMR (300 MHz, DMSO-d6): = 7.90 (s; broad; 6H; -NH2;
HC1; tauscht mit D2O aus),HC1; exchanges with D2O),
7,51 (s; 1H; Ring-H) , 4,54 ( ; 1H; -CH (CH3)2) und 1,30 ppm (d; 6H-CH(CH3)2) •7.51 (s; 1H; Ring-H), 4.54 (; 1H; -CH (CH3) 2) and 1.30 ppm (d; 6H-CH (CH3) 2) •
MS (70 eV) : m/e = 140 (M+)MS (70 eV): m / e = 140 (M + )
Herstellungsbeispiel 24: 4-Amino-l-(2'-hydroxyethyl)-5-Production Example 24: 4-amino-1- (2'-hydroxyethyl) -5-
(2'-hydroxyethyl)aminopyrazol(2'-hydroxyethyl) aminopyrazole
0,8 g (2,7 mmol) 3-Brom-l-(2'-hydroxyethyl)-5-(2 '-hydro¬ xyethyl)amino-4-nitropyrazol werden nach Vorschrift (1) 4 Stunden lang hydriert. Nach Abfiltrieren des Kataly¬ sators fügt man 0,27 g (2,7 mmol) Schwefelsäure (97pro- zentig) zu. Nach Abkühlen auf - 30 CC erhält man 630 mg (82 Prozent der Theorie) 4-Amino-l-(2'-hydroxyethyl)-5- (2'-hydroxyethyl)aminopyrazol-hydrosulfat in Form farb¬ loser Kristalle mit einem Schmelzpunkt von 140 bis 142 °C.0.8 g (2.7 mmol) of 3-bromo-1- (2'-hydroxyethyl) -5- (2'-hydroxyethyl) amino-4-nitropyrazole are hydrogenated for 4 hours according to procedure (1). After filtering off the catalyst, 0.27 g (2.7 mmol) of sulfuric acid (97 percent) is added. After cooling to - 30 C C to obtain 630 mg (82 percent of theory) of 4-amino-l- (2'-hydroxyethyl) -5- (2'-hydroxyethyl) aminopyrazole hydrosulfate farb¬ in the form of a white crystal having a melting point from 140 to 142 ° C.
iH-NMR (60 MHz, DMSO-d6): = 10,18 (s; breit; 7H;-NH;iH-NMR (60 MHz, DMSO-d6): = 10.18 (s; broad; 7H; -NH;
-NH2; -OH; H2SO4; mit D2O austauschbar), 7,37 (s; 1H; Ring-H), 4,00 (m; 2H; -CH2-), 3,53-NH2; -OH; H2SO4; interchangeable with D2O), 7.37 (s; 1H; Ring-H), 4.00 (m; 2H; -CH2-), 3.53
(m; breit; 4H; -CH2-) und 3,13 ppm (m; 2H; -CH2-).(m; broad; 4H; -CH2-) and 3.13 ppm (m; 2H; -CH2-).
MS (70 eV) : m/e = 186 (M+) . Herstellungsbeispiel 25: 4-Amino-l-(2 '-hydroxyethyl)-5- methylaminopyrazolMS (70 eV): m / e = 186 (M + ). Preparation 25: 4-amino-1- (2'-hydroxyethyl) -5-methylaminopyrazole
2,65 g (10 mmol) 3-Brom-l-(2 '-hydroxyethyl)-5-methylami- no-4-nitropyrazol werden 4 Stunden lang nach Vorschrift (1) hydriert. Nach Zugabe von 1 g (10 mmol) Schwefel¬ säure und 10 ml Isopropanol scheidet sich das Produkt ab. Man erhält 1 g (40 Prozent der Theorie) 4-Amino-l- (2 '-hydroxyethyl)-5-methylaminopyrazol-hydrosulfat in Form farbloser Kristalle mit einem Schmelzpunkt von 138 bis 140 °C.2.65 g (10 mmol) of 3-bromo-1- (2'-hydroxyethyl) -5-methylamino-4-nitropyrazole are hydrogenated for 4 hours according to procedure (1). After adding 1 g (10 mmol) of sulfuric acid and 10 ml of isopropanol, the product separates. 1 g (40 percent of theory) of 4-amino-l- (2'-hydroxyethyl) -5-methylaminopyrazole hydrosulfate are obtained in the form of colorless crystals with a melting point of 138 to 140 ° C.
iH-NMR (300 MHz,DMSO-d6 ) : = 9,6 (s; 2H;-NH2, tauscht mit D2θ aus), 7,38 (s; 1H; Ring-H), 6,35 (s; 2H; -NH und -OH; tauscht mit D2O aus) , 3,96 (t; J = 5,8 Hz; 2H; -CH2-CH2) , 3,65 (t; J = 5,7 Hz; 2H; -CH2-CH2-) undiH-NMR (300 MHz, DMSO-d6): = 9.6 (s; 2H; -NH2, exchanges with D2θ), 7.38 (s; 1H; Ring-H), 6.35 (s; 2H ; -NH and -OH; exchanges with D2O), 3.96 (t; J = 5.8 Hz; 2H; -CH2-CH2), 3.65 (t; J = 5.7 Hz; 2H; - CH2-CH2-) and
2,80 ppm (s; 3H; -NH-CH3)2.80 ppm (s; 3H; -NH-CH3)
MS (70 eV) : m/e = 156 (M+)MS (70 eV): m / e = 156 (M + )
Herstellungsbeispiel 26: 4,5-Diamino-l-(2'-hydroxyethyl) pyrazolPreparation Example 26: 4,5-diamino-1- (2'-hydroxyethyl) pyrazole
1,7 g (5 mmol) 5-Benzylamino-3-brom-l-(2 '-hydroxyethyl)- 4-nitropyrazol werden 4 Stunden lang nach Vorschrift (1) hydriert. Nach Zugabe von 0,5 g (5 mmol) Schwefelsäure erhält man 0,8 g (62 Prozent der Theorie) 4 ,5-Diamino-l- (2 '-hydroxyethyl)pyrazol-hydrosulfat-hydrat in Form farbloser Kristalle mit einem Schmelzpunkt von 158 bis 160 °C. Herstellungsbeispiel 27: 4-Amino-(3)5-methylaminopyrazol1.7 g (5 mmol) of 5-benzylamino-3-bromo-1- (2'-hydroxyethyl) -4-nitropyrazole are hydrogenated for 4 hours according to procedure (1). After addition of 0.5 g (5 mmol) of sulfuric acid, 0.8 g (62 percent of theory) of 4,5-diamino-l- (2'-hydroxyethyl) pyrazole hydrosulfate hydrate are obtained in the form of colorless crystals with a melting point from 158 to 160 ° C. Preparation 27: 4-amino- (3) 5-methylaminopyrazole
1 g (2,9 mmol) l-Benzyl-3-brom-5-methylamino-4-nitro- pyrazol werden in einer Lösung von 0,29 g (2,9 mmol) Schwefelsäure in 50 ml Wasser gemäß Vorschrift (2) über einen Zeitraum von 8 Stunden hydriert. Nach Abfiltrieren des Katalysators und Zugabe von 50 ml Ethanol wird das Filtrat auf 30 ml eingeengt und auf - 30 °C abgekühlt. Man erhält 244 mg (40 % der Theorie) 4-Amino-(3)5-me- thylaminopyrazol-hydrosulfat in Form farbloser Kristalle mit einem Schmelzpunkt von 182 °C.1 g (2.9 mmol) of l-benzyl-3-bromo-5-methylamino-4-nitrophyrazole are dissolved in a solution of 0.29 g (2.9 mmol) of sulfuric acid in 50 ml of water according to regulation (2) hydrogenated over a period of 8 hours. After filtering off the catalyst and adding 50 ml of ethanol, the filtrate is concentrated to 30 ml and cooled to -30 ° C. 244 mg (40% of theory) of 4-amino- (3) 5-methylaminopyrazole hydrosulfate are obtained in the form of colorless crystals with a melting point of 182 ° C.
iH-NMR (60 MHz, DMS0-d6): = 10,10-9,20 (m; 6H; NH;-NH2;iH-NMR (60 MHz, DMS0-d6): = 10.10-9.20 (m; 6H; NH; -NH2;
H2SO4; mit D2θ-austausch- bar); 7,95 (s; 1H; Ring-H) undH2SO4; interchangeable with D2θ); 7.95 (s; 1H; Ring-H) and
2,85 ppm (s; 3H; -CH3) . MS (70 eV) : m/e = 112 (M+) .2.85 ppm (s; 3H; -CH3). MS (70 eV): m / e = 112 (M +).
Herstellungsbeispiel 28: 4-Amino-(3)5-ethylaminopyrazolPreparation 28: 4-amino- (3) 5-ethylaminopyrazole
0,5 g (1,31 mmol) l-Benzyl-3-Brom-5-ethylamino-4-nitro- pyrazol werden in einer Lösung von 130 mg (1,31 mmol) Schwefelsäure in 50 ml Wasser gemäß Vorschrift (2) über einen Zeitraum von 8 Stunden hydriert. Nach Abfiltrieren 0.5 g (1.31 mmol) of l-benzyl-3-bromo-5-ethylamino-4-nitrophyrazole are dissolved in a solution of 130 mg (1.31 mmol) of sulfuric acid in 50 ml of water according to regulation (2) hydrogenated over a period of 8 hours. After filtering
des Katalysators wird das Filtrat auf 10 ml eingeengt. Anschließend gibt man 10 ml Ethanol hinzu, woraufhin das Produkt in Form farbloser Kristalle, mit einem Schmelz¬ punkt von 188 °C, auskristallisiert. Man erhält 0,1 g (34 Prozent der Theorie) 4-Amino-(3)5-ethylaminopyra- zol-hydrosulfat.of the catalyst, the filtrate is concentrated to 10 ml. Then 10 ml of ethanol are added, whereupon the product crystallizes out in the form of colorless crystals with a melting point of 188 ° C. 0.1 g (34 percent of theory) of 4-amino- (3) 5-ethylaminopyrazole hydrosulfate is obtained.
iH-NMR (300 MHz,DMSO-d6) : = 8,53 (s; breit; 6H; -NH;iH-NMR (300 MHz, DMSO-d6): = 8.53 (s; broad; 6H; -NH;
-NH2; H2SO4; tauscht mit D2O aus) , 7,78 (s; 1H; Ring-H) ; 3,21 (q; J = 7,1 Hz; 2H; -CH2-CH3) und 1,18 ppm (t; J = 7,1 Hz; 3H; -CH2-CH3) .-NH2; H2SO4; exchanges with D2O), 7.78 (s; 1H; Ring-H); 3.21 (q; J = 7.1 Hz; 2H; -CH2-CH3) and 1.18 ppm (t; J = 7.1 Hz; 3H; -CH2-CH3).
MS (70 eV) : m/e = 126 (M+) .MS (70 eV): m / e = 126 (M +).
Herstellungsbeispiel 29: 4-Amino-(3)5-(2'-hydroxyethyl) aminopyrazolPreparation 29: 4-amino- (3) 5- (2'-hydroxyethyl) aminopyrazole
1 g (2,9 mmol) l-Benzyl-3-brom-5-(2 '-hydroxyethyl)amino- 4-nitropyrazol werden in einer Lösung von 0,29 g (2,9 mmol) Schwefelsäure und 50 ml Wasser über einen Zeitraum von 3 Stunden gemäß Vorschrift (2) hydriert. Nach Abfil¬ trieren des Katalysators wird das Lösungsmittel im Vaku¬ um abdestilliert. Das dabei auskristallisierte Produkt wird mit wenig (20 ml) Ethanol gewaschen und anschlie¬ ßend getrocknet. Man erhält 240 mg (35 Prozent der Theorie) 4-Amino-(3)5-(2 '-hydroxyethyl)aminopyrazol- hydrosulfat in Form farbloser Kristalle mit einem Schmelzpunkt von 185 °C. iH-NMR (60 MHz, DMSO-d6): = 8,35 (s; breit; 6H; -NH;1 g (2.9 mmol) of l-benzyl-3-bromo-5- (2 '-hydroxyethyl) amino-4-nitropyrazole are dissolved in a solution of 0.29 g (2.9 mmol) of sulfuric acid and 50 ml of water hydrogenated for a period of 3 hours according to regulation (2). After filtering off the catalyst, the solvent is distilled off in vacuo. The product which crystallizes out is washed with a little (20 ml) of ethanol and then dried. 240 mg (35 percent of theory) of 4-amino- (3) 5- (2'-hydroxyethyl) aminopyrazole hydrosulfate are obtained in the form of colorless crystals with a melting point of 185 ° C. iH-NMR (60 MHz, DMSO-d6): = 8.35 (s; broad; 6H; -NH;
-NH2; -OH; H2SO4, mit D2O aus tauschbar), 7,58 (s; 1H; Ring-H); 3,55 (m, 2H; -CH2-OH) und 3,15 ppm (m; 2H; -NH-CH2-) .-NH2; -OH; H2SO4, exchangeable with D2O), 7.58 (s; 1H; Ring-H); 3.55 (m, 2H; -CH2-OH) and 3.15 ppm (m; 2H; -NH-CH2-).
MS (70 eV) : m/e = 142 (M+)MS (70 eV): m / e = 142 (M + )
Herstellungsbeispiel 30: 4, (3)5-DiaminopyrazolPreparation 30: 4, (3) 5-diaminopyrazole
1 g (2,4 mmol) l-Benzyl-5-benzylamino-3-brom-4-nitro- pyrazol werden in einer Lösung von 0,25 g (2,4 mmol) Schwefelsäure und 50 ml Wasser über einen Zeitraum von 4 Stunden gemäß Vorschrift (2) hydriert. Nach Abfiltrieren des Katalysators fügt man dem Filtrat 50 ml Ethanol zu und kühlt auf - 30 °C ab. Man erhält 184 mg (39 Prozent der Theorie) 4, ( 3)5-Diaminopyrazol-hydrosulfat in Form farbloser Kristalle mit einem Schmelzpunkt von 240 °C (Zersetzung) .1 g (2.4 mmol) of l-benzyl-5-benzylamino-3-bromo-4-nitrophyrazole are dissolved in a solution of 0.25 g (2.4 mmol) of sulfuric acid and 50 ml of water over a period of 4 Hours hydrogenated according to regulation (2). After filtering off the catalyst, 50 ml of ethanol are added to the filtrate and the mixture is cooled to −30 ° C. 184 mg (39 percent of theory) of 4, (3) 5-diaminopyrazole hydrosulfate are obtained in the form of colorless crystals with a melting point of 240 ° C. (decomposition).
Verwendungsbeispiel:Example of use:
6,35 g 4-Amino-l-(2 '-hydroxyethyl)-5-methylamino- pyrazol 2,73 g 3-Aminophenol 10,00 g Laurylalkohol-diglycolethersufat-Natriumsalz6.35 g of 4-amino-1- (2'-hydroxyethyl) -5-methylamino-pyrazole 2.73 g of 3-aminophenol 10.00 g of lauryl alcohol diglycol ether sulfate sodium salt
(28prozentige wäßrige Lösung) 10,00 g Ammoniak (22prozentige wäßrige Lösung)(28 percent aqueous solution) 10.00 g ammonia (22 percent aqueous solution)
100,00 g 50 g des vorstehenden Haarfärbemittels werden unmittel¬ bar vor Gebrauch mit 50 g Wasserstoffperoxidlösung (6- prozentig) gemischt. Das Gemisch wird anschließend auf blonde Naturhaare aufgetragen und 30 Minuten lang bei einer Temperatur von 40 °C einwirken gelassen. Das Haar wird anschließend mit Wasser gespült und getrocknet. Das Haar ist in einem modischen Purpurton gefärbt. 100.00 g 50 g of the above hair dye are mixed with 50 g of hydrogen peroxide solution (6 percent) immediately before use. The mixture is then applied to blonde natural hair and left to act at a temperature of 40 ° C for 30 minutes. The hair is then rinsed with water and dried. The hair is colored in a fashionable purple tone.

Claims

PatentansprücheClaims
1) Verfahren zur Herstellung von 4,5-Diaminopyrazol- Derivaten den allgemeinen Formel (I)1) Process for the preparation of 4,5-diaminopyrazole derivatives of the general formula (I)
Figure imgf000037_0001
i
Figure imgf000037_0001
i
in der Ri und R2 unabhängig voneinander Wasserstoff, einen Ci- bis C6-Alkylrest oder einen C2- bis C4-Hy- droxyalkylrest bedeuten, dadurch gekennzeichnet, daß manin which R 1 and R 2 independently of one another denote hydrogen, a C 1 -C 6 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, characterized in that
(A) 3,5-Dibrom-4-nitropyrazol mit einem Ci- bis Cß- Alkyl-, C2- bis C4-Hydroxyalkyl- oder Benzyl- halogenid oder einem Cχ~ bis Cß-Alkyl-, C2- bis C4-Hydroxyalkyl- oder Benzylsulfat zu Verbin¬ dungen der allgemeinen Formel (II)(A) 3,5-dibromo-4-nitropyrazole with a Ci to Cβ-alkyl, C2 to C4-hydroxyalkyl or benzyl halide or a Cid ~ to Cß-alkyl, C2 to C4-hydroxyalkyl or benzyl sulfate to compounds of the general formula (II)
Figure imgf000037_0002
in der R3 einen Ci- bis C6-Alkylrest, einen C2- bis C4-Hydroxyalkylrest oder einen Benzylrest bedeutet, umsetzt,
Figure imgf000037_0002
in which R3 is a Ci to C6 alkyl radical, a C2 to C4 hydroxyalkyl radical or a benzyl radical,
(B) die Verbindungen der allgemeinen Formel (II) mit Ci- bis Cö-Alkyl-, C2- bis C4-Hydroxyalkyl- oder Benzylamin zu Verbindungen der allgemeinen Formel (III)(B) the compounds of the general formula (II) with Ci- to Cö-alkyl-, C2- to C4-hydroxyalkyl- or benzylamine to give compounds of the general formula (III)
Figure imgf000038_0001
I
Figure imgf000038_0001
I
R3 R 3
in der R3 und R4 unabhängig voneinander einen Ci- bis Cß-Alkylrest, einen C2- bis C4-Hydroxy- alkylrest oder einen Benzylrest bedeuten, in 5-Position substituiert und sodannin which R3 and R4 independently of one another are a C 1 -C 6 -alkyl radical, a C 2 -C 4 -hydroxyalkyl radical or a benzyl radical, substituted in the 5-position and then
(C) die Verbindungen der allgemeinen Formel (III) durch katalytische Hydrierung zu den Verbin¬ dungen der allgemeinen Formel (I) reduziert. (C) the compounds of the general formula (III) are reduced to the compounds of the general formula (I) by catalytic hydrogenation.
2) Verbindungen der allgemeinen Formel (II)2) compounds of the general formula (II)
Figure imgf000039_0001
Figure imgf000039_0001
in der R3 einen Ci- bis Cδ-Alkylrest, einen C2- bis C4-Hydroxyalkylrest oder einen Benzylrest bedeutet.in which R3 is a Ci- to Cδ-alkyl radical, a C2- to C4-hydroxyalkyl radical or a benzyl radical.
3) 3,5-Dibrom-l-methyl-4-nitropyrazol.3) 3,5-dibromo-l-methyl-4-nitropyrazole.
4) 3,5-Dibrom-l-ethyl-4-nitropyrazol.4) 3,5-dibromo-1-ethyl-4-nitropyrazole.
5) 3,5-Dibrom-l-isopropyl-4-nitropyrazol .5) 3,5-dibromo-l-isopropyl-4-nitropyrazole.
6) 3,5-Dibrom-l-(2 '-hydroxyethyl)-4-nitropyrazol .6) 3,5-dibromo-1- (2'-hydroxyethyl) -4-nitropyrazole.
7) l-Benzyl-3,5-dibrom-4-nitropyrazol.7) l-Benzyl-3,5-dibromo-4-nitropyrazole.
8) Verbindungen der allgemeinen Formel (III)8) Compounds of the general formula (III)
Figure imgf000039_0002
I
Figure imgf000039_0002
I
R3 in der R3 und R4 unabhängig voneinander einen Ci- bis Cß-Alkylrest, C2- bis C4-Hydroxyalkylrest oder einen Benzylrest bedeuten.R 3 in which R3 and R4 independently of one another are a C 1 -C 6 -alkyl radical, C2- to C4-hydroxyalkyl radical or a benzyl radical.
) 3-Brom-l-methyl-5-methylamino-4-nitropyrazol .) 3-bromo-l-methyl-5-methylamino-4-nitropyrazole.
3-Brom-5-(2 '-hydroxyethyl)amino-l-methyl-4-nitro- pyrazol.3-bromo-5- (2'-hydroxyethyl) amino-l-methyl-4-nitrophyrazole.
1 3-Brom-5-tertiärbutylamino-l-methyl-4-nitropyrazol.1 3-bromo-5-tertiarybutylamino-l-methyl-4-nitropyrazole.
5-Benzylamino-3-brom-l-methyl-4-nitropyrazol.5-benzylamino-3-bromo-1-methyl-4-nitropyrazole.
5-Benzylamino-3-brom-l-ethyl-4-nitropyrazol.5-benzylamino-3-bromo-1-ethyl-4-nitropyrazole.
5-Benzylamino-3-brom-l-isopropyl-4-nitropyrazol .5-benzylamino-3-bromo-l-isopropyl-4-nitropyrazole.
3-Brom-1-(2 '-hydroxyethyl)-5-(2 '-hydroxyethyl)amino- 4-nitropyrazol.3-bromo-1- (2'-hydroxyethyl) -5- (2'-hydroxyethyl) amino-4-nitropyrazole.
3-Brom-l-(2 '-hydroxyethyl)-5-methylamino-4-nitro- pyrazol.3-bromo-1- (2'-hydroxyethyl) -5-methylamino-4-nitro-pyrazole.
5-Benzylamino-3-brom-l-(2 '-hydroxyethyl )-4-nitro- pyrazol5-benzylamino-3-bromo-1- (2'-hydroxyethyl) -4-nitro-pyrazole
l-Benzyl-3-brom-5-methylamino-4-nitropyrazol.l-benzyl-3-bromo-5-methylamino-4-nitropyrazole.
l-Benzyl-3-brom-5-ethylamino-4-nitropyrazol .l-benzyl-3-bromo-5-ethylamino-4-nitropyrazole.
l-Benzyl-3-brom-5-(2 '-hydroxyethyl)amino-4-nitro- pyrazol.l-benzyl-3-bromo-5- (2'-hydroxyethyl) amino-4-nitro-pyrazole.
l-Benzyl-5-benzylamino-3-brom-4-nitropyrazol . 22) Verbindungen der allgemeinen Formel (V)l-benzyl-5-benzylamino-3-bromo-4-nitropyrazole. 22) Compounds of the general formula (V)
Figure imgf000041_0001
Figure imgf000041_0001
in der Ra und Rb Wasserstoff, einen Ci- bis C6-A1- kylrest oder einen C2- bis C4-Hydroxyalkylrest bedeuten, mit der Maßgabe, daß, wenn Rb Wasserstoff ist, Ra nicht Wasserstoff, Methyl oder 2-Hydroxy- ethyl ist.in which R a and Rb denote hydrogen, a C 1 -C 6 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical, with the proviso that when R b is hydrogen, R a is not hydrogen, methyl or 2-hydroxy- is ethyl.
23 ) 4-Amino-l-methyl-5-methylaminopyrazol .23) 4-Amino-1-methyl-5-methylaminopyrazole.
24 ) 4-Amino-5- ( 2 ' -hydroxyethyl ) amino- 1-methylpyrazol .24) 4-Amino-5- (2'-hydroxyethyl) amino-1-methylpyrazole.
25) 4,5-Diamino-l-ethylpyrazol.25) 4,5-diamino-1-ethylpyrazole.
26) 4 ,5-Diamino-l-isopropylpyrazol.26) 4,5-diamino-l-isopropylpyrazole.
27) 4-Amino-1-(2'-hydroxyethyl)-5-(2'-hydroxyethyl)- aminopyrazol.27) 4-Amino-1- (2'-hydroxyethyl) -5- (2'-hydroxyethyl) aminopyrazole.
28) 4-Amino-l-(2'-hydroxyethyl)-5-methylaminopyrazol.28) 4-Amino-1- (2'-hydroxyethyl) -5-methylaminopyrazole.
29) 4-Amino-(3)5-methylaminopyrazol. 30) 4-Amino-(3)5-ethylaminopyrazol.29) 4-Amino- (3) 5-methylaminopyrazole. 30) 4-Amino- (3) 5-ethylaminopyrazole.
31) 4-Amino-(3)5-(2'-hydroxyethyl)aminopyrazol.31) 4-amino- (3) 5- (2'-hydroxyethyl) aminopyrazole.
32) Verwendung einer Verbindung der allgemeinen Formel (V) als Farbstoffvorstufe in Oxidationshaarfärbe- mitteln. 32) Use of a compound of the general formula (V) as a dye precursor in oxidation hair dye.
PCT/EP1993/002644 1992-10-16 1993-09-29 Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives WO1994008969A1 (en)

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WO2022129386A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dyeing base, at least one guar gum and at least one fatty substance
WO2022129394A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dyeing base and at least two particular couplers
WO2022129355A1 (en) 2020-12-17 2022-06-23 L'oreal Cosmetic composition comprising a combination of two particular couplers and a nonionic surfactant of alkylpolyglycoside type
WO2022129349A1 (en) 2020-12-17 2022-06-23 L'oreal Dyeing composition based on 2-gamma-hydroxypropyl-para-phenylenediamine and a phosphoric surfactant
WO2022129384A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising the combination of at least one fatty substance, a particular carboxylic acid and an oxidation dye and/or an alkaline agent
WO2022129391A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising the combination of two particular oxidation dye precursors and an alkyl(poly)glycoside
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WO2022129379A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising two particular oxidation dye precursors, and a particular carboxylic acid
WO2022129377A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising the combination of two particular oxidation dye precursors and a particular carboxylic acid
FR3117819A1 (en) 2020-12-17 2022-06-24 L'oreal COLORING COMPOSITION BASED ON 2-γ-HYDROXYPROPYL-PARA-PHENYLENEDIAMINE AND A PHOSPHORIC SURFACTANT
FR3117827A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising a particular oxidation coloring precursor and a particular carboxylic acid
WO2022129373A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising the combination of two particular oxidation dye precursors and a particular oxyethylenated fatty acid ester of sorbitan
FR3117812A1 (en) 2020-12-17 2022-06-24 L'oreal Cosmetic composition comprising a combination of two particular couplers and N,N-dicarboxymethyl glutamic acid and/or its salts
FR3117813A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of at least one fatty substance, a particular carboxylic acid and an oxidation dye and/or an alkaline agent
FR3117829A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of two particular oxidation coloring precursors and an alkyl(poly)glycoside.
WO2022129350A1 (en) 2020-12-17 2022-06-23 L'oreal Cosmetic composition comprising a combination of two particular couplers and an oxyethylenated fatty acid ester of sorbitan
FR3117835A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of two particular oxidation coloring precursors and an alkyl(poly)glycoside.
FR3117866A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising a particular oxidation coloring base, at least one associative polymer and at least one fatty substance.
WO2022129380A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dye precursor and a particular carboxylic acid
FR3117811A1 (en) 2020-12-17 2022-06-24 L'oreal Cosmetic composition comprising a combination of two particular couplers and an oxyethylenated ester of fatty acid and sorbitan
FR3117816A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising a particular oxidation coloring base and at least two particular couplers.
WO2022129383A1 (en) 2020-12-17 2022-06-23 L'oreal Process for dyeing keratin fibres with a composition comprising a particular oxidation dye precursor, a particular carboxylic acid and a chemical oxidizing agent
FR3117828A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of three particular oxidation coloring precursors.
FR3117817A1 (en) 2020-12-17 2022-06-24 L'oreal Cosmetic composition comprising a combination of two particular couplers and at least one oxidation base
FR3117840A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising two particular oxidation coloring precursors, an ester of fatty acid and oxyethylenated sorbitan and a fatty acid
WO2022129385A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising the combination of two particular oxidation dye precursors, an alkyl(poly)glycoside and a sulfated anionic surfactant
WO2022129389A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dyeing base, at least one particular coupler and at least one fatty substance
FR3117814A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising a particular oxidation coloring base, at least one guar gum and at least one fatty substance.
FR3117839A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of two specific oxidation coloring precursors and a specific carboxylic acid
FR3117841A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising two particular oxidation coloring precursors, and a particular carboxylic acid
FR3117815A1 (en) 2020-12-17 2022-06-24 L'oreal Cosmetic composition comprising a combination of two particular couplers and a nonionic surfactant of the alkylpolyglycoside type
FR3117836A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of two particular oxidation coloring precursors and an alkyl(poly)glycoside.
FR3117830A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising a particular oxidation coloring base, at least one particular coupler and at least one fatty substance.
FR3117826A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of two particular oxidation coloring precursors and an alkyl(poly)glycoside.
FR3117838A1 (en) 2020-12-17 2022-06-24 L'oreal Composition comprising the combination of two particular oxidation coloring precursors and a particular fatty acid and oxyethylenated sorbitan ester.
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WO2022129393A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dyeing base, at least one associative polymer and at least one fatty substance
WO2022129357A1 (en) 2020-12-17 2022-06-23 L'oreal Cosmetic composition comprising a combination of two particular couplers and at least one oxidation base
WO2022129369A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising two particular oxidation dye precursors, an oxyethylenated fatty acid ester of sorbitan and a fatty acid
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FR3117823A1 (en) 2020-12-18 2022-06-24 L'oreal Hair coloring process using specific resorcinol derivatives, associated compositions and new compounds
FR3117805A1 (en) 2020-12-18 2022-06-24 L'oreal Composition for lightening keratin fibers and process for lightening keratin fibers using this composition
FR3117806A1 (en) 2020-12-18 2022-06-24 L'oreal Composition for the simultaneous bleaching and coloring of keratin fibers and method using this composition
WO2022129343A1 (en) 2020-12-18 2022-06-23 L'oreal Process for lightening keratin fibres
FR3117808A1 (en) 2020-12-18 2022-06-24 L'oreal Composition for the simultaneous bleaching and coloring of keratin fibers and method using this composition
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FR3117807A1 (en) 2020-12-18 2022-06-24 L'oreal Composition for lightening keratin fibers and process for lightening keratin fibers using this composition
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WO2022129345A1 (en) 2020-12-18 2022-06-23 L'oreal Process for lightening keratin fibres
FR3117809A1 (en) 2020-12-18 2022-06-24 L'oreal Composition for lightening keratin fibers and process for lightening keratin fibers using this composition
FR3118707A1 (en) 2021-01-08 2022-07-15 L'oreal Solid composition for dyeing and/or lightening keratinous fibers
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FR3124705A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising propan-1,3-diol, at least one alkanolamine, at least one fatty substance and optionally at least one polyol
FR3124713A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising N,N-dicarboxymethyl glutamic acid, propane-1,3-diol, at least one nonionic surfactant, at least one alkaline agent and/or at least one colorant
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FR3124732A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising shea, an alkyl(poly)glycoside, a polysaccharide and an alkaline agent and/or a dye
FR3124733A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one oxidation base, at least an alkaline agent, and a fatty substance derived from shea
FR3124702A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising propane-1,3-diol and at least one fatty substance and one or more alkaline agents and/or one or more colorants.
FR3124709A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one alkanolamine, one (meta)silicate, glycine and propane-1,3-diol.
FR3124719A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one particular coupler, at least one particular oxidation base, at least one fatty substance and at least one anionic polysaccharide.
FR3124716A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one alkanolamine, one (meta)silicate, glycine and N,N-dicarboxymethyl glutamic acid.
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FR3124710A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one particular coupler, propane-1,3-diol, at least one alkaline agent and at least one fatty substance.
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FR3124724A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one alkyl(poly)glycoside, at least one fatty alcohol, at least one fatty acid, and at least one alkaline agent
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FR3124720A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one particular coupler, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol.
FR3124727A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising an alkanolamine, a (meta)silicate, glycine, a dye and a polysaccharide.
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FR3124706A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising at least one alkanolamine, one (meta)silicate, glycine and one fatty acid.
FR3124715A1 (en) 2021-06-30 2023-01-06 L'oreal Composition comprising N,N-dicarboxymethyl glutamic acid, at least one fatty alcohol, at least one fatty acid, at least one polyol, at least one alkaline agent and optionally at least one colorant
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FR3127130A1 (en) 2021-09-17 2023-03-24 L'oreal Compositions to CONFER COLOR and TONE to the hair
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FR3136973A1 (en) 2022-06-22 2023-12-29 L'oreal Keratin fiber treatment process
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DE4234885A1 (en) 1994-04-21
JPH07502542A (en) 1995-03-16
BR9305675A (en) 1994-12-20
EP0618902A1 (en) 1994-10-12
ES2060574T1 (en) 1994-12-01

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