GB2104517A - Pantothenate salts of quinine - Google Patents

Abstract

Pantothenate salts of quinine of the formula: (C9H17NO5) x C20H24N2O2 where x=1 (basic pantothenate> or x=2 (neutral pantothenate), are new and are prepared by reaction of pantothenic acid with quinine in the presence of alcohol, the pantothenic acid preferably being in aqueous solution. The pantothenate salts of quinine can be used in cosmetic products for the care of hair and other phanera.

Description

SPECIFICATION Pantothenates of quinine The present invention relates to new chemical compounds, namely pantothenates of quinine, to processes for their preparation, and to cosmetic products containing the same.

The compounds of the invention have the advantage of combining the qualities of pantothenic acid and those of quinine in the form of stable compounds whose efficiency is increased in comparison to the relative instability of pantothenic acid.

The combination of the properties of pantothenic acid and of quinine is of particular interest for the treatment of hair and other phanera.

According to the present invention there is provided a chemical compound constituted at least in part by a pantothenate of quinine of the formula: (CgH17NOs) x C20H24N202 where x = 1 or 2.

Two such compounds are distinguished, namely the neutral pantothenate of quinine, oftheformula: (CgH17NOs)2 C20H24N2O2 having a molecular weight of about 762.87, and basic pantothenate of quinine, of the formula: CgHr7NOs . Cp0H24N2O2 having a molecular weight of about 563.64.

It is of particular interest to use these compounds in the form of aqueous solutions of neutral pantothenate of quinine of rotative power[a]2D0 = -110 to -120 , whose ultraviolet spectrum has two maxima of absorption at 325 and 275 nm, presenting a blue fluorescence, precipitating with the general reagents of alkaloids, and liberating through hydrolysis p-alanine in a quantity corresponding to their pantothenic acid content.

Thus the new pantothenates of quinine give the conventional reactions of precipitating alkaloids in a slightly acidic aqueius environment.

lodised reagents, such as iodo-bismuthite of potassium, give an orange-red precipitate; alkaline iodomercurates give a white precipitate, and iodoiodised reagents gives a brown precipitate. Acid reagents such as picric acid give a yellow precipitate; reagents of heavy metals, such as silicotungstic or phospho-tungstic acids, give a white precipitate.

An aqueous solution of tannin gives a beige precipitate.

Neutral pantothenate is the more soluble in water and alcohol, and for this reason its use is generally more interesting than that of basic pantothenate.

The invention is also a process for preparing pantothenates of quinine, by reacting pantothenic acid with quinine in the presence of alcohol, in orderto obtain a hydroalcoholic solution of pantothenate of quinine.

The pantothenic acid is preferably in aqueous solution. The quinine is preferably in solution.

In this way an aqueous solution of pantothenate of calcium may be reacted with an aqueous solution of oxalic acid, the resulting precipitate, calcium oxalate, being removed by filtration, and the filtrate being caused to react in a solution of basic quinine in ethanol in order to obtain a hydroalcoholic solution of pantothenate of quinine.

Alternatively, one can dissolve pantothenate of calcium in water, add ethyl alcohol and then an aqueous solution of neutral sulphate of quinine, and remove, for example by filtration, the calcium sulphate precipitated in the hydroalocohlic solution of pantothenate of quinine.

It is generally advantageous to evaporate the hydroalcoholic solution in vacuo until pantothenate of quinine is obtained in the form of a white to whiteyellowish vitreous substance which is extremely hygroscopic and soluble in water and alcohol.

The manufacturing processes of neutral pantothenate and basic pantothenate differ only in the quantity of pantothenic acid used.

The invention also provides cosmetic products, particularlyforthe care of hair and otherphanera, characterised in that they contain pantothenate of quinine, preferably as an active quantity.

The average active quantity is 1%. Lowerconcent- ration may be used, but there is a risk of them being less effective, while higher concentrations would generally be needlessly expensive.

The new pantothenates of quinine may be used in all the cosmetic forms generally in use with which they are compatible.

Thus one may produce hydroalcoholic capillary lotions, shampoos, oils or creamy emulsions of eitherwaterin oil or oil in water.

The cosmetic products of this invention can be used in a conventional manner.

Shampoos are used from 1 to 3 times per week, while the oils and creams, as well as the lotions, are usually applied daily.

Application on the nails is preferably done at cuticle level, while for eyebrows and hair, application is essentially on the base of the hairs, the action being exerted at the level of the follicles.

For the hair, it is generally easier to apply the lotion, cream or oil with a pad along strands previously drawn out by a comb.

Daily application should be carried out for 3 weeks at least before the effects of the products are noticed.

This duration substantially corresponds to the cycle of the hair follicles.

Application ofthe products ofthis invention encourages the regrowth of hair, which is generally abundant and fine, at the first cycle and remains abundant, but is of normal size from the second cycle onwards.

Upon application there will be noticed a slight congestion accompanied by pink colouration of the skin.

No action is noticed on the canitia of the divided hairs.

Embodiments of the invention will now be described by way of illustration in the following Examples.

Example 1.

Preparation of neutral pantothenate of quinine by action of an aqueous solution of pantothenic acid on an alcoholic solution of basic quinine: To 22 ml of an aqueous solution at 10g per 100 ml of pantothenic acid there are added 1.629 of basic quinine previ ously dissolved in 25 ml of ethyl alcohol at 960.

The reaction is carried out at normal ambient temperature.

Example 2.

Preparation of pantothenic acid from pantothenate of calcium by precipitation of calcium by oxalic acid: 2.409 of pantothenate of calcium are dissolved in 15 ml of distilled water. 0.634g of oxalic acid, dissolved in 10 ml of water, are added. The precipitate of calcium oxalate is allowed to settle, and is separated by filtration. The precipitate is washed in 2 ml of water.

The filtrate constitutes a solution of pure pantothenic acid.

Example 3.

Preparation of basic pantothenate of quinine: To the filtrate in Example 2 there are added 0.819 of basic quinine, previously dissolved in 12.5 ml of ethyl alcohol at 960.

In this way, a hydroalcoholic solution of pantothenate of basic quinine is obtained.

Example 4.

Preparation of neutral pantothenate of quinine by double decomposition between pantothenate of calcium and sulphate of quinine: 2.409 of pantothenate of calcium are dissolved in 15 ml of distilled water.

50 ml of ethyl alcohol at 96" are added, and then, slowly, 2.749 of neutral sulphate of quinine dissolved in 35 mi of distilled water. Calcium sulphate is precipitated. Its separation is facilitated by the presence of alcohol. After settling for 24 hours, the product is filtered on fretted glass, and the precipitate is washed slowly in alcohol, these operations being carried out at normal ambient temperature.

Example 5.

To obtain anhydrous pantothenate of quinine: The hydroalcoholic solutions in the previous Examples are evaporated in vacuo. Thus there is obtained a vitreous white to white-yellowish substance which is very hydroscopic and soluble in water and alcohol.

Example 6.

Preparation of a cosmetic oil: 1% of pantothenate of quinine is added to castor oil, and alcohol at 96" is added with stirring, until a clear solution is obtained.

Example 7.

Preparation of a hair lotion: 1 g of pantothenate of quinine is dissolved in about 100 ml of alcohol at 30".

Example 8.

Preparation of a shampoo: The process is conventional, according to the following formula: pantothenate of quinine ig lauric alcohol 1.509 betainic ampholytes 8.25g amido alkylbetain 11.20g amino oxide of amines 1.309 imidazolidimylurea 0.150g demineralised water 679 2-Bromo-2-nitropropane-1,3-diol 0.0509 Example 9.

Preparation of a cream: An oil in water emulsion is prepared in conventional manner to the following formula: neutral pantothenate of quinine 1g cetylicalcohol 189 stearate of triethanolamine 149 stearate of diethylene glycol 5g monopalmitate of sorbitan, detergent sold underthe commercial title "Span 40" 39 monopalmitate of polyoxyethylenised sorbitan with 20 oxides oftheylene, wetting agent sold under the commercial title "Tween 40" 39 antioxidant NDGA (nordehydroguaiaretic acid) 0.19 water qsp 100 ml All these preparations may have perfumes added thereto, preferably of a non-allergenic type.

It will be appreciated that the invention is in no way limited to the Examples described; it is capable of numerous variations within the reach of the person skilled in the art, depending on the applications intended, without going outwith the framework of the invention.

Claims (18)

1. A chemical compound constituted at least in part by a pantothenate of quinine of the following formula: (CgH17NOs) x C20H24N2O2 where = 1 or 2.

2. A chemical compound according to Claim 1, wherein the pantothenate of quinine is a neutral pantothenate of quinine oftheformula: (CgH17NOs2 C20H24N202.

3. A chemical compound according to Claim 1, wherein the pantothenate of quinine is a basic pantothenate of quinine ofthe following formula: CgH17NOs. C2oH24N2O2w

4. A chemical compound according to Claim 1 or 2 2 in the form of an aqueous solution of neutral pan- tothenate of quinine of a rotative power[o)0 20 = -4 10 to -'120", whose ultraviolet spectrum has two maxima of absorption at 325 and 275 nm, having a blue fluorescence, precipitating with general reagents of alkaloids and liberating by hydrolysis ss-alinine in a quantity corresponding to its pantothenic acid content.

5. A chemical compound according to Claim 1, substantially as hereinbefore described with reference to any one of the Examples.

6. A process for manufacturing the pantothenate of quinine defined in any one of Claims 1 to 5, characterised in that pantothenic acid is caused to react with quinine in the presence of alcohol.

7. A process according to Claim 6, wherein the pantothenic acid is in aqueous solution.

8. A process according to Claim 7, wherein an aqueous solution of pantothenate of calcium is caused to react with an aqueous solution of oxalic acid, the calcium oxalate formed, is separated and the remaining product is caused to react with a solution of basic quinine in ethanol, in order to obtain a hydroalcoholic solution of pantothenate of quinine.

9. A process according to Claim 6 or 7, wherein pantothenate of calcium is dissolved in water, ethyl alcohol and an aqueous solution of neutral sulphate of quinine are added, and calcium sulphate is removed from the reaction product.

10. A process according to any one of Claims 7 to 9, wherein the hydroalcoholic solution formed is evaporated until pantothenate of quinine is obtained.

11. A process for manufacturing the pantothenate of quinine in any one of Claims 1 to 5, substantially as hereinbefore described with reference to any one of the Examples.

12. A cosmetic product containing pantothenate of quinine.

13. A cosmetic product according to Claim 12, in the form of a capillary lotion which is hydroalcoholic and perfumed and contains about 1 % of pantothe- nate of quinine.

14. A cosmetic product according to Claim 12, in the form of an aqueous shampoo having about 1% of pantothenate of quinine, 65 to 70% water, 1.5% lauric alcohol, 8.25% betainic ampholytes, 11.20% amidoalkylbetain, 1.30% amino oxide of amines, 0.15% of imidazolidimylurea, 0.05% of 2 - Bromo - 2 nitropropane -1,3- diol.

15. A cosmetic product according to Claim 12, in the form of a solution of about 1% of pantothenate of quinine in a mixture of castor oil and alcohol.

16. A cosmetic product according to Claim 12, in the form of a creamy emulsion having about 1% of pantothenate of quinine, 14% of stearate of triethanolamine, 5% of stearate of diethylene glycol, 18% of cethylic acid, 0.1% of norehydroguaiaretic acid, 3% of monopalmitate of sorbitan, 3% of polyoxyethylenised monopalmitate of sorbitan with 20 oxides of ethylene, and 56% of water.

17. A cosmetic product substantially as hereinbefore described with reference to any one of the Examples.

18. A compound manufactured by the process according to any one of Claims 6 to 11.