CH670633A5 - - Google Patents

Description

DESCRIPTION

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The present invention relates to mono-, di- and triesters of 1,8-dihydroxy-phenyl-10 anthrone-9 or anthranol-9, a process for the preparation of these esters and the pharmaceutical or cosmetic compositions containing them.

45 In human or veterinary therapy, these esters find particular application as antiproliferative agents, in particular in the treatment of psoriasis and warts, or as anti-inflammatory agents in the treatment of rheumatism, dermatoses and eczema or as anti-acne agents.

In cosmetics, these esters are anti-dandruff agents, anti-borrheic and against hair loss and can be used for skin prone to acne.

The mono-, di- and triesters of dihydroxy-1,8 phenyl-10 anthrone-55 9 or anthranol-9 according to the invention have, compared to dihydroxy-1,8 phenyl-10 anthrone, the advantage of be more stable and less stain the skin and clothes, especially in basic washing.

The mono-, di- and triesters of 1,8-dihydroxy-phenyl-10 anthrone-9 or anthranol-9 can be represented by the following general formula 60:

O (Rj) OCOR3

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(I)

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in which:

p is 0 or 1

a) when p = 0, t = 1 and R2 represents a hydrogen atom or

-cor3,

b) when p = 1, t = 0 and Rj and R2 represent, independently of one another, a hydrogen atom or - COR3,

R3 representing an alkyl radical, linear or branched, having from 1 to 17 carbon atoms, a cycloalkyl radical, or a phenyl radical optionally substituted by a lower alkyl, a lower alkoxy, a halogen atom, a nitro function, a radical - CF3 or by a hydroxyl function,

and mixtures of said esters.

By linear or branched alkyl radical having from 1 to 17 carbon atoms, is meant a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiobutyl, pentyl, isopentyl, heptyl, nonyl, undecyl, pentadecyl radical. heptadecyl.

The term “cycloalkyl radical” should be understood to mean a radical having from 3 to 6 carbon atoms, but preferably the cyclopentyl or cyclohexyl radical.

When the phenyl radical is substituted by a lower alkyl radical, the latter is preferably a methyl, ethyl or tert-butyl radical.

When the phenyl radical is substituted by a lower alkoxy radical, the latter is preferably the methoxy or ethoxy radical.

When the phenyl radical is substituted by a halogen atom, the latter is preferably a chlorine or fluorine atom.

According to a preferred embodiment of the invention, the compounds according to the invention are diesters or triesters represented by the following formulas:

ocor, ocor,

r.coo r, coo ocor.

c6h.

(II) (iii)

Mention may in particular be made, among the esters according to the invention of formula (I):

- 10-phenyl-triacetoxy-1,8,9 anthracene,

- 10-phenyl-tripropionyloxy-1,8,9 anthracene,

- 10-phenyl-tributyryloxy-1,8,9 anthracene,

- 10-phenyl triisobutyryloxy-1,8,9 anthracene,

- 1,8-diisobutyryloxy phenyl-10 anthrone-9,

- 10-phenyl tricyclohexylcarbonyloxy-1,8,9 anthracene,

- 1,8-dipivaloyloxy-phenyl-10 anthrone-9,

- phenyl-10 tribenzoyloxy-1,8,9 anthracene,

- 10-phenyl tricyclopentylcarbonyloxy-1,8,9 anthracene,

- 10-phenyl-trioctanoyloxy-1,8,9 anthracene,

- 10-phenyl-triundecanoyloxy-1,8,9 anthracene,

- phenyl-10 trioctadecanoyloxy-1,8,9 anthracene,

- 10-phenyl tritolylcarbonyloxy-1,8,9 anthracene,

- 10-phenyl tri- (p-methoxybenzoyloxy) -1.8.9 anthracene,

- 10-phenyl tri- [m- (trifluoromethyl) benzoyloxy] -1.8.9 anthracene.

The present invention also relates to the process for the preparation of 1,8-dihydroxy-phenyl-10 anthrone-9 or anthranol-9 esters as defined above.

Dihydroxy-1,8 phenyl-10 anthrone-9 is a known compound, the preparation of which has been described in "Arch. der Pharmazie ”, 298, 273-81 (1965), presenting three possible O-acylation sites which, depending on the operating conditions and the nature of the reagent, allow access to the mono-, di- or triesters.

These esters can however be obtained in the form of a mixture which is fractionated by chromatography.

The esters according to the invention are obtained by reacting, on 1,8-dihydroxy-phenyl-10 anthrone-9, an activated form of acid such as an acid anhydride, (R3C0) 20, or a chloride of acid, R3COCl, in the presence of a base and, preferably, an aromatic amine such as pyridine, optionally in an aromatic solvent medium such as toluene and at a temperature between 20 and 130 ° C.

The formation of the mono-, di- or triesters is a function of the molar proportions of the acid anhydride or of the acid chloride reacted and of the reaction time.

For the preparation of the mono- and diesters, 1.5 to 2.5 equivalents of acid chloride or acid anhydride are preferably used and the reaction is monitored by thin layer chromatography in order to stop it. either at the monoester stage or at the diester stage.

For the preparation of the triesters, a large excess of acid chloride or acid anhydride is used and, in order to complete the reaction, the temperature is preferably brought to 80-110 ° C.

When using a particularly congested acid chloride such as for example pivaloyl chloride, it is particularly easy to access the diesters even in the presence of excess, without there being any significant formation of the corresponding triester.

Insofar as an easily removable acid chloride is used, either by evaporation or by washing in a basic medium, it is desirable to carry out the reaction using the acid chloride both as solvent and as reagent and add 4 to 8 equivalents of pyridine.

In this case, the operation is then carried out at a temperature between 20 and 60 ° C., and the reaction is particularly rapid.

After the end of the reaction, when the latter is carried out in a solvent, water is poured into the reaction medium and various washes are carried out, in particular using a solution of sodium bicarbonate. The organic phase is then dried over magnesium sulfate and then filtered. The product can be purified either by recrystallization in the evening by chromatography on silica gel, preferably using toluene or a toluene / ethyl acetate mixture as eluent.

In human or veterinary therapy, the compounds according to the invention are antiproliferative agents, in particular in the treatment of psoriasis and warts, and useful as anti-inflammatory agents, in particular in the treatment of rheumatism, dermatosis and eczema as well as acne.

In cosmetics, the compounds according to the invention can be used in the treatment of acne-prone skin, dandruff, seborrhea and hair loss.

The cosmetic or pharmaceutical compositions according to the invention can be prepared for example by adding an ester of formula (I), at a concentration of between 0.01 and 5%, in various inert non-toxic supports, solid or liquid, generally used in compositions for cosmetic or therapeutic use.

The pharmaceutical compositions can be administered enterally, parenterally or topically. For enteral administration, the compositions are in the form of tablets, powders, granules, capsules, syrups, suspensions or solutions.

The dosage is of course a function of the route of administration and the activity sought.

The pharmaceutical compositions can also contain inert additives. The tablets or granules can contain, for example, binders, fillers, carriers or diluents.

The liquid compositions can be present for example in the form of a sterile solution miscible with water. In addition to the active compound, the capsules may contain a filler or a thickener. Oral pharmaceutical compositions may also contain flavor enhancers and substances commonly used as preservatives, stabilizers.

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health, antioxidants, regulators and emulsifiers. You can also add salts and buffers.

The carriers and diluents as listed above can consist of organic or mineral substances, for example by gelatin, lactose, starch, magnesium stearate, talc, gum arabic, oils vegetable and mineral, fillers, thickeners, dyes, humectants or po-lyalkylene glycols.

When the pharmaceutical compositions are intended for topical application, they are in the form of an ointment, an ointment, a gel, a tincture, a cream, a solution, a lotion, micronized powder, spray, suspension, shampoo or soaked pads.

Ointments or ointments are preferred and are prepared by mixing an ester according to the invention with inert non-toxic supports suitable for topical treatment.

We will now give by way of illustration and without being limiting, several examples of preparation of the esters according to the invention as well as several examples of compositions for therapeutic and cosmetic use.

Preparation of 1,8-dihydroxy-phenyl-10 anthrone-9

a) Preparation of phenyl-10 trihydroxy-lj8,10 anthrone-9

In a 2 liter reactor fitted with mechanical agitation,

30 g of dihydroxy-1,8 anthraquinone and 2 liters of anhydrous t-trahydrofuran are placed with an inlet of argon, a condenser and an introduction vial. The solution obtained is then cooled to -70 ° C.

At this temperature, the anthraquinone is crystallized. A solution which contains 4 equivalents of phenyllithium is then added with stirring over 30 minutes.

The temperature is maintained throughout the addition between -60 and -70 ° C. At the end of the addition, it is checked on a sample taken that all of the 1,8-dihydroxy anthraquinone is transformed. At this temperature, the reaction medium is acidified by adding 400 cm3 of acetic acid, then the mixture is allowed to return to room temperature. The solvent is evaporated to dryness under reduced pressure. The product obtained, in the form of an oily mass, crystallizes on stirring in water.

The crystals obtained are drained, washed with dichloromethane and then dried. 32 g of yellow crystals are thus obtained which are recrystallized from methanol. The product has a melting point of 126 ° C.

Analysis for C20H14O4:

Calculated: C 75.46 H 4.43 0 20.10%

Found: C 75.48 H 4.35 0 19.95%

b) Preparation of 1,8-dihydroxy-phenyl-10 anthrone-9

50 g of phenyl-10-trihydroxy-1,8,10 anthrone-9 are introduced into a 2 liter reactor fitted with mechanical stirring and an argon inlet, followed by 200 g of ground stannous chloride and 2 liters. acetic acid.

To this mixture, stirred at ambient temperature, 200 cm 3 of concentrated hydrochloric acid are then added dropwise over 30 minutes. The disappearance of phenyl-10 trihydroxy-1,8,10 anthrone-9 is followed by thin layer chromatography. After about 2 hours, the reduction reaction is complete. The 1,8-dihydroxy-phenyl-10 anthrone-9 precipitated in the medium is drained, washed with water and dried. 42 g of light yellow crystals are thus obtained. The filtrate is poured onto a mixture of 1 liter of water and 1 kg of crushed ice. The rest of the product precipitated, it is drained, washed with water and dried. An additional 4 g of the expected product are thus isolated.

The dihydroxy-1,8,10 phenyl-10 anthrone-9 thus obtained is pure.

It has a melting point of 193-194 ° C.

Analysis for C20H14O3:

Calculated: C 79.45 H 4.66 0 15.87%

Found: C 79.25 H 4.71.016.00%

5 The structure of 1,8-dihydroxy-phenyl-10 anthrone-9 is confirmed by mass spectrography where the parent peak is observed on the spectrum at m / e: 302 by direct ionization and at m / e: 303 by chemical ionization with isobutane corresponding to M + H +. These results are in agreement with the molar mass of 302 g of the product. The NMR spectrum also confirms this structure. One observes in particular a singlet at 5.30 ppm whose integration corresponds to a proton. It is that which is hey to carbon in position 10 of the anthrone nucleus.

The signal of the eleven aromatic protons is a multiplet whose 5 15 is from 6.60 to 7.50 ppm (11).

Finally, the spectrum shows another singlet at 12.40 ppm, which disappears by exchange with heavy water and whose integration corresponds well to the two protons of the hydroxyl groups in positions 1 and 8.

20 Example I

Preparation of 10-phenyl-triacetoxy-1,8,9 anthracene

A mixture of 40 g of 1,8-dihydroxy-10 phenyl-anthrone and 0.5 cm3 of pyridine in 400 cm3 of acetic anhydride is stirred under an inert atmosphere and gradually brought to a temperature between 60 and 70 ° C. The starting product is quantitatively transformed into the corresponding triacetate after 3 hours. After cooling using an ice bath, the product crystallizes. It is drained, washed with ethyl ether and then dried. 45 g of a greenish-yellow solid are thus obtained, which is dissolved in a mixture of 200 cm3 of acetic acid and 200 cm3 of 1,2-dichloroethane brought to a temperature of approximately 80 ° C. solution is then filtered at this temperature and, by cooling the filtrate, the product crystallizes. It is drained, washed with ethyl ether and dried.

35 g of 10-phenyl-triacetoxy-1,8,9 anthracene are obtained, in the form of light yellow crystals with a melting point of 279 ° C.

Analysis for C2SH20O6:

Calculated: C 72.88 H 4.70 0 22.40%

40 Found: C 72.87 H 4.73 0 22.15%

Example II

Preparation of phenyl-10 tripropionyloxy-1,8,9 anthracene

To a stirred mixture under an argon atmosphere of 2.5 g of dihy-45 droxy-1,8 phenyl-10 anthrone in 25 cm3 of propionic anhydride, 0.100 cm3 of anhydrous pyridine is added. The reaction mixture is then brought for 1 hour to 70 ° C, time after which all the starting material is transformed. The excess reagent is then removed by evaporation under vacuum. The solid obtained is dissolved in a minimum of toluene, deposited on a column of silica gel and then eluted with toluene. After evaporation of the eluent, 1.3 g of a solid are obtained which is recrystallized from a toluene / hexane mixture. 1.1 g of white crystals with a melting point of 216 ° C. are thus isolated.

__ Analysis for

Calculated: C 74.02 H 5.56 0 20.40%

Found: C 74.14 H 5.59 0 20.19%

Example III

60 Preparation of phenyl-10 triisobutyryloxy-1,8,9 anthracene

A mixture, stirred under an inert atmosphere, of 3 g of 1,8-dihydroxy-phenyl-10 anthrone, of 3.16 cm3 of pyridine (4 equivalents) and of 4.26 cm3 of isobutyryl chloride (4 equivalents) in 100 cm3 of anhydrous toluene is brought to reflux of the solvent for 10 hours. The reaction medium is then washed several times with water. The organic phase is then decanted, dried over magnesium sulfate and concentrated. The product obtained in the form of a viscous liquid is dissolved in the minimum amount of toluene and deposited on a column of gel.

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silica. The expected triester is eluted with a toluene / methylene chloride mixture (3/1). After concentrating the eluent, 2.3 g of solid are obtained which is recrystallized from toluene. 1.4 g of phenyl-10 triisobutyryloxy-1,8.9 anthracene are isolated in the form of yellow crystals with a melting point of 224 ° C.

Analysis for C32H3206:

Calculated: C 74.98 H 6.29 0 18.72%

Found: C 74.78 H 6.27 0 18.57%

Example IV

Preparation of phenyl-10 tri- (cyclohexylcarbonyloxy) -1.8.9 anthracene

To a mixture of 3 g of dihydroxy-1,8 phenyl-10 anthrone in 15 cm3 of cyclohexanecarboxylic acid chloride, 3.2 cm3 of pyridine is added slowly with stirring. The reaction medium is then brought to 100 ° C. for 3 hours. It is then diluted to ordinary temperature, by the addition of 200 cm 3 of methylene chloride, then washed with bicarbonate water and then with water. The organic phase is dried over sodium sulfate. After evaporation of the methylene chloride, 4.2 g of a yellow solid is obtained which is recrystallized from a toluene / ethyl ether mixture. After filtration and drying, 3.75 g of phenyl-10 tri- (cyclohexylcarbonyIoxy) -1.8.9 anthracene are obtained in the form of yellow-colored crystals with a melting point of 235 ° C.

Analysis for C41H4406:

Calculated: C 77.82 H 7.00 0 15.17%

Found: C 77.97 H 7.00 0 15.01%

Example V

Preparation of dipivaloyloxy-1,8 phenyl-10 anthrone

A mixture of 3 g of 1,8-dihydroxy-phenyl-10 anthrone, 3.16 cm 3 of pyridine, 4.8 cm 3 of pivaloyl chloride in 100 cm 3 of anhydrous toluene is stirred under an argon atmosphere for 10 hours at the boiling point of the solvent. After cooling to room temperature, the reaction medium is washed several times with water. The organic phase is decanted, dried over magnesium sulfate and concentrated. The residue deposited on a column of silica gel is then eluted using toluene. After concentrating the elution phases, 2.38 g of a solid are obtained which is recrystallized from a toluene / hexane mixture.

1.4 g of dipivaloyloxy-1,8 phenyl-10 anthrone are thus isolated in the form of white crystals with a melting point of 160 ° C.

Analysis for C30H30O5:

Calculated: C 76.57 H 6.42 0 16.99%

Found: C 76.40 H 6.40 0 16.92%

Example VI

Preparation of phenyl-10 tribenzoyloxy-1,8,9 anthracene

To a mixture stirred at room temperature and under an inert atmosphere of 1 g of 1,8-dihydroxy-10-phenyl-anthrone-9 in 15 cm3 of benzoyl chloride, 1.2 cm3 of pyridine are added dropwise.

After 1 hour of stirring, all of the starting anthron is transformed into the corresponding triester. The reaction medium is concentrated under reduced pressure, dissolved in 100 cm3 of methylene chloride, washed several times with water and finally dried over sodium sulfate.

The organic phase is then deposited on a column of silica gel and eluted with a toluene / methylene chloride mixture, progressively enriched in methylene chloride.

After concentrating the elution phases, 1.55 g of triester are obtained, which is recrystallized from toluene. The crystals are wrung and dried. 1 g of phenyl-10 tribenzoyloxy-1,8,9 anthracene is thus isolated in the form of yellow crystals with a melting point of 225 ° C.

Analysis for C41H2606:

Calculated: C 80.12 H 4.26 0 15.62%

Found: C 80.08 H 4.32 0 15.79%

Example VII

Preparation of diisobutyryloxy-1,8 phenyl-10 anthrone

A mixture, stirred away from light and under an inert atmosphere, of 18 g of 1,8-dihydroxy-10-phenyl-anthrone, 19 cm3 of pyridine and 25 cm3 of isobutyryl chloride in 500 cm3 of anhydrous toluene is brought to reflux of the solvent for 5 hours.

After cooling, the reaction mixture is washed three times with water and dried over magnesium sulfate.

The residue obtained after evaporation under reduced pressure is then deposited on a column of silica gel. The column is eluted with toluene and then with a toluene / methylene chloride mixture, the latter being progressively enriched in methylene chloride.

At the top of the chromatography, 5 g of phenyl-10-triisobutyryloxy-1,8,9 anthracene described in Example III are isolated, after evaporation of the solvent.

The following fractions rich in diester are concentrated and the product obtained is recrystallized from a toluene / pentane mixture.

1.5 g of diisobutyryloxy-1,8 phenyl-10 anthrone are obtained in the form of beige crystals with a melting point of 136 ° C.

Analysis for C28H26Os:

Calculated: C 76.00 H 5.92 0 18.08%

Found: C 75.75 H 5.99 0 18.36%

Example VIII

Preparation of phenyl-10 tributyryloxy-1,8,9 anthracene

To a suspension stirred, protected from light and under an inert atmosphere, of 18 g of 1,8-dihydroxy-10-phenyl-anthrone in 500 cm3 of anhydrous toluene, 19 cm3 of pyridine and 24.5 cm3 of butyryl chloride are added. . The mixture is then brought to toluene reflux for 3 hours, time after which the starting material is completely transformed.

After cooling, the mixture is washed three times with water and the toluene phase is dried over sodium sulfate. After concentration, the residue is deposited on a column of silica gel. The expected product is eluted with a hexane / toluene mixture.

After concentrating the eluting solvent, 23 g of product are obtained which is recrystallized from a toluene / pentane mixture, which leads to 16 g of 10-phenyl-1,8-tributyryloxy-1,8,9 anthracene in the form of light yellow crystals melting point: 150 ° C.

Analysis for C32H3206:

Calculated: C 74.98 H 6.29 0 18.72%

Found: C 75.00 H 6.47 0 18.57%

Examples of pharmaceutical and cosmetic compositions

Example 1: 0.5 g insoluble tablet

- Phenyl-10 triacetoxy-1,8,9 anthracene 0,100 g

- Lactose 0.082 g

- Stearic acid 0.003 g

- Purified talc 0.015 g

- Sweetener q.s.

- Colorant q.s.

- Rice starch q.s.p. 0.500 g This tablet is prepared by direct dry compression of the mixture of the various constituents.

Example 2: 0.8 g non-soluble tablet

- Phenyl-10 triisobutyryloxy-1,8,9 anthracene 0,200 g

- Lactose 0.200 g

- Gum arabic 20% in water 0.080 g

- Liquid paraffin 0.004 g

- Purified talc 0.016 g

- Starch q.s.p. 0.800 g s

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For a good conservation, this emulsion should be stored mixture of 10-phenyl-triisobutyryloxy-1,8,9 anthracene, starch, away from heat and light.

lactose and gum arabic 20% in water.

The granules are then dried and then sieved. These last Example 8: Anhydrous gel are then mixed with paraffin and talc. 5 —Dipivaloyloxy-1,8 phenyl-10 anthrone 1.50 g

- Aerosol 200 (silica) from Degussa 7.00 g

- Isopropyl myristate q.s.p. 100.00 g

- Phenyl-10 tripropionyloxy-1,8 anthracene 2.00 g Miglyol 812 (triglycerides of capric / caprylic acids) from the company Dynamit

Nobel q.s.p. 20.00 g

Example 3: Granules in 3 g sachets

- Phenyl-10 tripropionyloxy-1,8,9 anthracene 0,150 g

- Sucrose 2.220 g Example 9: Milk in two parts to be emulsified extemporaneously Methylellulose 0.030 g First part

- Purified water 0.600

The paste obtained by mixing the four constituents is granular - Miglyol 812 (acid triglycerides moistened and then dried. Capric / caprylic) from the company Dynamit

Example 4 Capsules Containing 0.05 g of Active Compound

- Phenyl-10 tri- (cyclohexylcarbonyloxy) -1.8.9 Second part anthracene 0.050 g - Tween 80 (polyoxy sorbitan monooleate)

- Cod liver oil q.s.p. 0.500 g ethylenated to 20 moles of ethylene oxide) of the

The capsule shell is produced by molding and then drying at Atlas Company 10.00 g of a suitable mixture composed of gelatin, glycerin, water and preservative q.s.

servant. The suspension containing the active compound is introduced - Sterile demineralized water q.s.p. 80.00 g in the capsule which is then sealed. The first part is agitated in order to bring the active compound into

Example 5: Capsule containing 0.3 g of suspension powder, then the two parts are mixed before applying the milk.

Powder composition: 25

- Dipivaloyloxy-1,8 phenyl-10 anthrone 0,080 g Example 10: Stick

Corn starch 0.060 g - 10-phenyl-triisobutyryloxy-1,8.9 anthracene 5.00 g

-Lactose q.s.p. 0.300 g _ Cocoa butter 12.50 g

The powder is packaged in a capsule composed of gelatin - Ozokerite wax 18.50 g tine, titanium dioxide and a preservative. 30 - Refined white paraffin 6.25 g

- Vaseline oil 12.75 g

- • Isopropyl myristate q.s.p. 100.00 d

EXAMPLE 11 Hair Loss and Dandruff Composition

EXAMPLE 6 Hydrophobic Ointment

- DipivaIoyloxy-1,8 phenyl-10 anthrone 1.00 g

- Vaseline 49.00 g

- Ceresin 15.00 g-

- Salicylic acid 0.30 g - Dipivaloyloxy-1,8 phenyl-10 anthrone 0.50 g

- Vaseline oil 34.70 g - Stannous chloride 0.30 g

- Isopropyl myristate q.s.p. 100.00 g

Example 7 Non-ionic emulsion for topical application

- Phenyl-10 triacetoxy-1,8,9 anthracene 0.70 g 40 ^ xemP ^ e 12: Ointment

- Eucerin anhydrous 70.00 g Diisobutyryloxy-1,8 phenyl-10 anthrone 1,00 g

- Vaseline oil 10.00 g —Miglyol 812 (acid triglycerides

- Curator q.s. caprylic / caprylic) from Dynamit Nobel 49.25 g

- Butylhydroxytoluene q.s. - White Vaseline 49.25 g

- Sterile demineralized water q.s.p. 100.00 g 45 - Salicylic acid 0.50 g

R

Claims (14)

670,633 1. Mono-, di- and triesters of 1,8-dihydroxy-phenyl-10 anthrone-9 or anthranol-9, characterized in that they correspond to the following formula: _ _ „ 0 (Rj) p OCORg (I) in which: p is 0 or 1 a) when p = 0, t = 1 and R2 represents a hydrogen atom or -cor3, b) when p = 1, t = 0 and Rj and R2 represent, independently of one another, a hydrogen atom or - COR3, R3 representing an alkyl radical, linear or branched, having from 1 to 17 carbon atoms, a cycloalkyl radical, or a phenyl radical optionally substituted by a lower alkyl, a lower alkoxy, a halogen atom, a nitro function, a radical - CF3 or by a hydroxyl function. 2. Compounds according to claim 1, characterized in that the alkyl radical having from 1 to 17 carbon atoms is a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiobutyl, pentyl, isopentyl, heptyl, nonyl, undecyl radical , pentadecyl or hepta-decyl. 2 3. Compounds according to claim 1, characterized in that the cycloalkyl radical is the cyclopentyl or cyclohexyl radical. 4. Compounds according to claim 1, characterized in that the phenyl radical is substituted by at least one methyl, ethyl, tert-butyl, methoxy, ethoxy radical, a fluorine or chlorine atom, a nitro function, the radical - CF3 or a hydroxyl function. 5. Compounds according to one of claims 1 to 4, characterized in that they are diesters of the following formula: R3C00 0 OCOR. R3 having the same meanings as those given in claim 1. 6. Compounds according to one of claims 1 to 4, characterized in that they are triesters of the following formula: R ^ COO ocor3 ocor3 R3 having the same meanings as those given in claim 1. 7. Compounds according to one of the preceding claims, characterized in that they are taken from the group consisting of: - phenyI-10 triacetoxy-1,8,9 anthracene, - 10-phenyl-tripropionyloxy-1,8,9 anthracene, - phenyl-10 tributyryloxy-1,8,9 anthracene, - 10-phenyl triisobutyryloxy-1,8,9 anthracene, - 1,8-diisobutyryloxy phenyl-10 anthrone-9, - 10-phenyl tricyclohexylcarbonyloxy-1,8,9 anthracene, - 1,8-dipivaloyloxy-phenyl-10 anthrone-9, - phenyl-10 tribenzoyloxy-1,8,9 anthracene, - 10-phenyl tricyclopentylcarbonyloxy-1,8,9 anthracene, 5 - 10-phenyl trioctanoyloxy-1,8,9 anthracene, - 10-phenyl-triundecanoyloxy-1,8,9 anthracene, - 10-phenyl trioctadecanoyloxy-1,8,9 anthracene, - 10-phenyl tritolylcarbonyloxy-1,8,9 anthracene, - phenyl-10 tri- (p-methoxybenzoyloxy) -1.8.9 anthracene, io - 10-phenyl tri- [m- (trifluoromethyl) benzoyloxy] -1.8.9 anthracene. 8. Process for the preparation of mono-, di- and triesters according to one of claims 1 to 7, characterized in that it consists in reacting, with or without solvent, on 1,8-dihydroxy-phenyl-10 year- 15 throne-9, an acid anhydride, (R3C0) 20, or an acid chloride, R3COCl, R3 having the same meanings as those given in claim 1, in the presence of a base and at a temperature between 20 and 130 ° C. 9. Method according to claim 8, characterized in that the reaction is carried out in toluene. 10. Pharmaceutical composition, characterized in that it contains as ingredient in an appropriate vehicle at least one compound according to one of claims 1 to 7. 11. Cosmetic composition, characterized in that it contains as active ingredient in an appropriate vehicle at least one compound according to one of claims 1 to 7. 12. Composition according to claim 10 or 11, characterized in that it contains the active ingredient at a concentration of between 0.01 and 5% relative to the total weight of the composition. 30 13. Use of a compound according to one of claims 1 to 7 for the preparation of a pharmaceutical composition intended for the treatment of psoriasis, warts, rheumatism, dermatoses, eczema and acne. 14. Use of a compound according to one of claims 1 to 7 35 for the preparation of a cosmetic composition intended for the treatment of acne-prone skin, dandruff, seborrhea and hair loss.