CA2481770C - Topical pharmaceutical compositions comprising proanthocyanidins for the treatment of dermatitis - Google Patents

Topical pharmaceutical compositions comprising proanthocyanidins for the treatment of dermatitis Download PDF

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CA2481770C
CA2481770C CA2481770A CA2481770A CA2481770C CA 2481770 C CA2481770 C CA 2481770C CA 2481770 A CA2481770 A CA 2481770A CA 2481770 A CA2481770 A CA 2481770A CA 2481770 C CA2481770 C CA 2481770C
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pharmaceutical composition
proanthocyanidins
dermatitis
acid
telmesteine
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CA2481770A1 (en
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Marco Mastrodonato
Roberto Ciattini
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Alliance Pharmaceuticals Ltd
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Sinclair Pharmaceuticals Ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/728—Hyaluronic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Abstract

Pharmaceutical compositions for the topical administration, comprising as active ingredients proanthocyanidins alone or combined with glycyrrhetinic acid, telmesteine, alpha-bisabolol or other components having complementary activity, in admixture with a suitable carrier, useful for the treatment of avariety of pathologies such as atopic dermatitis, allergic contact dermatitis, seborrheic dermatitis, radiation dermatitis, psoriasis, xerosis and atopia as well as for the treatment of mucosae inflammatory conditions.

Description

TOPICAL PHARMACEUTICAL COMPOSITIONS COMPRISING
PROANTHOCYANIDINS FOR THE TREATMENT OF DERMATITIS

The' present invention relates to pharmaceutical compositions for the topical administration comprising as active ingredients proanthocyanidins, glycyrrhetinic acid and telmesteine, in admixture with a suitable carrier.

The topical pharmaceutical compositions of the present invention are useful for the treatment of inflammatory conditions of the skin, such as atopic dermatitis, allergic contact dermatitis, seborrheic dermatitis, radiation dermatitis, psoriasis, xerosis and atopia as well as of mucosae and eye inflammatory conditions.

Dermatites are superficial skin inflammations, characterized by vesicles, erythema, edema, oozing, scaling or crusting lesions and intense itching. Various types of dermatitis exist: contact dermatitis, which can be caused by irritants with which the skin is in contact or by non-irritating substances to which the subject is allergic; atopic dermatitis, a chronic disease characterized by strong itching; seborrheic dermatitis, a scaling disease which mainly affect the face and scalp. In principle, the treatment consists in removing the offending agent, which however cannot in many cases be identified or removed. Treatment is therefore based on corticosteroids, which have however well known side-effects: they reduce the immune defenses, which can induce infections, mainly by fungi or Candida; suspension of the treatment should be gradual; they cannot be used during the acute oozing phase; a rebound effect may appear on stopping treatment. Furthermore, corticosteroids should not be used for prolonged treatments, particularly in children, since they can give rise to systemic effects.

In the case of seborrheic dermatitis, alternative treatments, based on hydrogenated vegetable oils or hydrophilic petrolatum, or medicated
2 shampoos (based on zinc-pirithione, selenium sulfide, sulfur and the like) in are not resolutive.

In case of the mucosae inflammatory conditions, in particular of mouth, gingival, rectal, vaginal and eye mucosae, a number of topical treatments are available, including the use of steroidal or non-steroidal antiinflammatory agents, with the problems and side effects characteristics for these medicaments.

Different uses of proanthocyanidins have been described in the pharmaceutical and cosmetic fields. EP 0 694 305 discloses topical compositions of proanthocyanidins combined with coumarins (esculoside and the like) for the treatment of peripheral vasculopathies, such as bedsores, scars, couperose, varices and the like. US 5,470,874 describes a combination of proanthocyanidins and vitamin C for the topical use, as sunscreen, for stimulating collagen synthesis and for restoring damaged collagen. Finally, JP
6,336,421 relates to topical formulations of proanthocyanidins combined with anti-inflammatories, among which glycyrrhetinic acid and derivatives are cited, for the cosmetic use and against sunburns. However, to date the use of proanthocyanidins in the treatment of pathologies such as chronic dermatitis, seborrheic dermatitis and allergic dermatis has not been described.

Proanthocyanidins are widely diffused in a number of vegetable species.
They are vegetable extracts containing bioflavonoids, with well-defined chemical profile, consisting for about 15% of dimers, about 20% of trimers and tetramers, and of small amounts of catechin and epicatechin. Proanthocyanidins exert both skin protecting action from the aggression by free radicals and restoration action of the damages to the skin structure through stimulation of collagen production. They also contain essential fatty acids similar to those of the skin hydrolipidic barrier, which contribute to keep said barrier intact.
Finally, proanthocyanidins reduce the concentration of enzymes such as elastase, collagenase, hyaluronidase and beta-glucuronidase, which are
3 PCT/EP03/03329 responsible for the destruction of elastin, collagen and hyaluronic acid proteins.
Therefore, proanthocyanidins are widely used in the pharmaceutical and cosmetic industries, thanks to their restoring, regenerating, nutrient and restructurant actions, which restores the skin elasticity and tonicity.

According to the present invention, the proanthocyanidins extracted from grape seeds and skin of Vitis vinifera are particularly preferred. Most preferred are the complexes of proanthocyanidins from Vitis vinifera with phospholipids, prepared according to the process disclosed in US 4,963,527.

18-(3-Glycyrrhetinic acid, extracted from the roots of Glycyrrhiza glabra, is known to have antiinflammatory properties on the skin, in particular in case of burns and redness.

Telmesteine (N-carbethoxy-4-thiazolidinecarboxylic acid) exerts antiradicalic and protective action against the oxidizing agents responsible for skin damages, as well as inhibiting elastase and collagenase actions.

The topical pharmaceutical compositions of the present invention will contain the active ingredients in admixture with a suitable carrier, preferably a carrier rich in polyunsaturated fatty acids. According to the invention, suitable carriers comprise squalene, fatty acids, fatty acids esters, vegetable oils, natural or synthetic triglycerids. More preferably, suitable carriers comprise squalene, karite butter, octyl palmitate and oenothera oil.

In particular, karite butter (also known as shea butter) is a fat consisting of a mixture of saturated and unsaturated fats, extracted from the seeds of Butirospermum parkii, a tree from northern Africa, which is used in cosmetics thanks to its protective and softening actions, which make it particularly useful for sensitive skins as well as for skins which easily redden.

Oenothera oil (also known as evening primrose oil), extracted from the plant Oenothera biennis, is rich in essential polyunsaturated fatty acids, in particular y-linolenic acid, indispensable for regenerating the skin and all
4 cellular tissues.

According to a preferred embodiment, the pharmaceutical compositions of the invention will further contain compounds with antioxidizing activity, such as tocopherols and ascorbic acid or esters thereof, preferably tocopherol acetate and ascorbyl palmitate or tetrapalmitate, to further increase the protective effect on cell membranes and to slow down the oxidation of polyunsaturated fatty acids.

The compositions of the present invention may further contain other active ingredients, with complementary or anyway useful actions in the treatment of dermatosis.

Examples of said active ingredients are:

salicylic acid, which exerts a keratolytic action useful for the treatment of seborrheic dermatitis;

hyaluronic acid, which is useful for the treatment of radiation dermatitis due to its hydrating and healing action;

alpha-bisabolol, one of the active principles present in chamomile essential oil (Matricaria flos), which has lenitive and anti-redness action;

zinc pidolate, which exerts slightly astringent, emollient and lenitive actions, blocks and prevents the formation of free radicals thanks to its competitive action towards iron ions, and is active in the enzymatic processes of skin metabolism;

allantoin which has astringent, slightly keratolytic and healing actions;
moisturizers or wetting agents;

piroctone olamine (OctopiroxTM), a known agent with antiseborrhoic activity.
Therefore, a further preferred embodiment relates to the pharmaceutical compositions of the invention also containing salicylic acid, for the treatment of seborrheic dermatitis.

A further preferred embodiment relates to the pharmaceutical compositions of the invention also containing hyaluronic acid, for the treatment of radiation dermatitis.

A further preferred embodiment relates to the pharmaceutical compositions of the invention also containing alpha-bisabolol and allantoin.
5 A further preferred embodiment relates to the pharmaceutical compositions of the invention also containing zinc pidolate.

A further preferred embodiment relates to the pharmaceutical compositions of the invention also containing glycyrrhetinic acid.

A further preferred embodiment relates to the pharmaceutical compositions of the invention also containing telmesteine.

In one particular embodiment there is provided a pharmaceutical composition for topical administration, comprising as active ingredients proanthocyanidins, glycyrrhetinic acid and telmesteine in admixture with a suitable carrier.

The topical pharmaceutical compositions of the present invention can be in the form of cream, gel, lotion, suspension, spray, ointment, foam.

The topical pharmaceutical compositions of the present invention will contain the active ingredients in the following concentrations (w/w):

a) proanthocyanidins in the form of complexes with phospholipids:
0.01% to 1%;

b) glycyrrhetinic acid: 0.1 to 5%, preferably 1 to 2%;
c) telmesteine: 0.01% to 1%; and - carriers (squalene, fatty acids, fatty acid esters, vegetable oils, natural or synthetic triglycerids, karite butter, octyl palmitate and oenothera oil):
10-50%;

- antioxidants (tocopherol acetate 0.5-5%; ascorbyl palmitate 0.01-0.1 %);
- salicylic acid 0.1-5%;

- hyaluronic acid 0.1-10%;

5a al fa-bisabol of 0.1-3%;

- zinc pidolate 0.01-1%;
- allantoin 0.1-2%.

The daily dosage will be determined by the physician; by way of example, it will consist of one or more daily applications even for protracted times.

Some examples of formulations according to the present invention are shown hereinafter.
6 Example 1 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 0.800 Telmesteine 0.100 Octyl palmitate 7.000 Pentylene glycol 5.000 Karite butter 4.000 Arachidyl alcohol, behenyl alcohol, C 12-20 alkylglucoside 4.000 Glyceryl stearate and glyceryl (100) OE stearate 3.000 Oenothera oil 2.000 Capriloyl glycine 1.500 Bisabolol 1.200 Vitamin E acetate 1.000 CarbomerTM 0.700 Octyl glycerin 0.600 Salicylic acid 0.500 OctoplroXTM 0.500 Sodium hydroxide 0.387 Allantoin 0.350 Zinc pidolate 0.100 EDTA disodium salt 0.08 Ascorbyl palmitate 0.05 Propyl gallate 0.02 Water 65.013 Total 100.000
7 Example 2 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 0.800 Telmesteine 0.100 Octyl palmitate 7.000 Pentylene glycol 5.000 Karite butter 4.000 Arachidyl alcohol, behenyl alcohol, C 12-20 alkylglucoside 4.000 Glyceryl stearate and glyceryl (100) OE stearate 3.000 Squalene 2.000 Oenothera oil 2.000 Capriloyl glycine 1.500 Bisabolol 1.200 Vitamin E acetate 1.000 Carbomer 0.700 Octyl glycerin 0.600 Sodium hydroxide 0.387 Zinc pidolate 0.100 EDTA disodium salt 0.08 Ascorbyl palmitate 0.05 Propyl gallate 0.02 Water 66.013 Total 100.000
8 Example 3 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 0.800 Telmesteine 0.010 Dub po 7.000 HydroliteTM-5 5.000 Karite butter 4.000 MontanovTM 202 4.000 ArlacelTM 165 3.000 Squalene ex 2.000 Oenothera oil 2.000 LipacideTM C8G 1.500 Bisabolol 1.200 Vitamin E acetate 1.000 CarbopolTM ultrez 10 0.700 SensivaTM SC 50 0.600 Octopirox 0.500 Sodium hydroxide drops P.P.A 0.387 Allantoin 0.350 Nipaguard DMDMH 0.300 Zincidone 0.100 EDTA disodium salt 0.080 Ascorbyl palmitate 0.050 Propyl gallate 0.020 Water 65.303 Total 100.000
9 Example 4 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 0.800 Telmesteine 0.010 Dub po 7.000 Hydrolite-5 5.000 Karite butter 4.000 Montanov 202 4.000 Arlacel 165 3.000 Squalene ex 2.000 Oenothera oil 2.000 Lipacide C8G 1.500 Bisabolol 1.200 Vitamin E acetate 1.000 Carbopol ultrez 10 0.700 Sensiva SC 50 0.600 Salicylic acid 0.500 Octopirox 0.500 Sodium hydroxide drops P.P.A 0.465 Allantoin 0.350 Nipaguard DMDMH 0.300 Zincidone 0.100 EDTA disodium salt 0.080 Ascorbyl palmitate 0.050 Propyl gallate 0.020 Water 64.725 Total 100.000 Example 5 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 0.800 Telmesteine 0.010 Dub po 7.000 Hydrolite-5 5.000 Karite butter 4.000 Montanov 202 4.000 Arlacel 165 3.000 Squalene 2.000 Oenothera oil 2.000 Lipacide C8G 1.500 Bisabolol 1.200 Vitamin E acetate 1.000 Carbopol ultrez 10 0.700 Sensiva SC 50 0.600 Octopirox 0.500 Sodium hydroxide drops P.P.A. 0.387 Allantoin 0.350 Nipaguard DMDMH 0.300 Zincidone 0.100 EDTA disodium salt 0.080 Ascorbyl palmitate 0.050 Hyaluronic acid sodium salt 0.030 Propyl gallate 0.020 Water 65.273 Total 100.000 Example 6 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 2.000 Telmesteine 0.010 Ethylhexyl palmitate 9.000 Butyrospermum parkii 6.000 Pentylene glycol 5.000 Butylene glycol 3.000 PEG-100 stearate 1.500 Glyceryl stearate 1.500 Capryloyl glycine 1.500 Arachidyl glucoside 1.360 Arachidyl alcohol 1.320 Behenyl alcohol 1.320 Bisabolol 1.200 Tocopheryl acetate 1.000 Carbomer 0.700 Ethylhexyl glycerin 0.600 Piroctone olamine 0.500 Sodium hydroxide 0.387 Allantoin 0.350 DMDM hydantoin 0.300 Sodium hyaluronate 0.200 Disodium EDTA 0.080 Tetrahexyidecyl ascorbate 0.050 Propyl Gallate 0.020 Water 61.003 Total 100.000 Example 7 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 2.000 Telmesteine 0.010 Ethylhxyl palmitate 9.000 Butyrospermum parkii 6.000 Pentylene glycol 5.000 Butylene glycol 3.000 PEG-100 stearate 1.500 Glyceryl stearate 1.500 Capryloyl glycine 1.500 Arachidyl glucoside 1.360 Arachidyl alcohol 1.320 Behenyl alcohol 1.320 Bisabolol 1.200 Salicylic acid 1.000 Tocopheryl acetate 1.000 Sodium hydroxide 0.785 Carbomer 0.700 Ethylhexylglycerin 0.600 Piroctone olamina 0.500 Allantoin 0.350 DMDM hydantoin 0.300 Disodium EDTA 0.080 Tetrahexyldecyl ascorbate 0.050 Propyl gallate 0.020 Water 59.805 Total 100.000 Example 8 CREAM
Complexes of proanthocyanidins from Vitis vinifera with phospholipids 0.100 Glycyrrhetinic acid 2.000 Telmesteine 0.010 Ethylhexyl palmitate 9.000 Butyrospermum parkii 6.000 Pentylene glycol 5.000 Butylene glycol 3.000 PEG-100 stearate 1.500 Glyceryl stearate 1.500 Capryloyl glycine 1.500 Arachidyl glucoside 1.360 Arachidyl alcohol 1.320 Behenyl alcohol 1.320 Bisabolol 1.200 Tocopheryl acetate 1.000 Carbomer 0.700 Ethylhexylglycerin 0.600 Piroctone olamine 0.500 Sodium hydroxide 0.387 Allantoin 0.350 DMDM hydantoin 0.300 Sodium hyaluronate 0.100 Disodium EDTA 0.080 Tetrahexyldecyl ascorbate 0.050 Propyl gallate 0.020 Water 61.103 Total 100.000 The compositions of the present invention showed very good tolerability. They do not contain allergenic substances, derivatives from animal sources (such as lanolin, beeswax, animal fat), preservatives (such as parabens, isothiazolones, phenol derivatives, and the like) which are often responsible for allergic contact dermatitis.

Therefore, thanks to the above mentioned characteristics, the compositions of the present invention are useful for the treatment of already existing skin allergic reactions, for the prevention of recurrent forms, and as adjuvants in the treatment of chronic diseases such as atopic dermatitis, allergic contact dermatitis, seborrheic dermatitis, radiation dermatitis, xerosis and atopia.

More particularly, the compositions of the present invention are useful in the treatment of conditions such as irritative and eczematous dermatitis, as moisturizers and lenitive agents for sensitive, delicate skin; in allergic irritations due to medicaments, detergents, solvents; in erythema due to excessive exposure to sun radiaitons; in case of insect stings, redness of various origin, post-shaving irritations, slight burns, skin hyper-reactivity;
as normalizers after esthetic treatments, such as peeling with acid glycolic or laser-therapy.

The excellent tolerability of the compositions of the present invention makes them also suitable in pediatrics.

The present invention also relates to the use of proanthocyanidins for the preparation of a topical medicament for the treatment of skin inflammations, in particular atopic dermatitis, allergic contact dermatitis, seborrheic dermatitis, radiation dermatitis, xerosis, psoriasis and atopia;
and of mucosae inflammatory conditions, in particular of vaginal, rectal, eye gingival and buccal mucosae.

Claims (20)

Claims
1. Use of a combination of proanthocyanidins, glycyrrhetinic acid and telmesteine for the preparation of a topical medicament for the treatment of inflammatory conditions of the skin and mucosae.
2. The use as claimed in claim 1 wherein the inflammatory conditions are inflammatory conditions of the vaginal, rectal, buccal and eye mucosae.
3. The use as claimed in claim 1 wherein the inflammatory conditions of the skin are atopic dermatitis, allergic contact dermatitis, seborrheic dermatitis, radiation dermatitis, xerosis, psoriasis and atopia.
4. The use as claimed in any one of claims 1-3, in which the proanthocyanidins are in the form of complexes with phospholipids.
5. The use as claimed in any one of claims 1-4, in which the proanthocyanidins are further in combination with alpha-bisabolol.
6 The use as claimed in any one of claims 1-5, in which the proanthocyanidins are further in combination with piroctone olamine.
7. The use as claimed in any one of claims 1-6, in which the proanthocyanidins are further in combination with wetting agents and moisturisers.
8. The use as claimed in any one of claims 1-7, which further comprises the use of one or more agents selected from the group consisting of salicylic acid, hyaluronic acid and zinc pidolate.
9. A pharmaceutical composition for topical administration, comprising as active ingredients proanthocyanidins, glycyrrhetinic acid and telmesteine in admixture with a suitable carrier.
10. The pharmaceutical composition as claimed in claim 9, in the form of cream, gel, lotion, suspension, spray, ointment, or foam.
11. The pharmaceutical composition as claimed in claim 9 or claim 10, in which the carrier comprises squalene, fatty acids, fatty acids esters, vegetable oils, natural or synthetic triglycerids.
12. The pharmaceutical composition as claimed in claim 11, in which the carrier comprises squalene, karité butter, octyr palmitate and oenothera oil.
13. The pharmaceutical composition as defined in any one of claims 9-12, further comprising tocopherols, ascorbic acid or esters thereof.
14. The pharmaceutical composition as defined in claim 13, comprising tocopherol acetate and ascorbyl palmitate or tetrapalmitate.
15. The pharmaceutical composition as defined in any one of claims 9-14, comprising salicylic acid.
16. The pharmaceutical composition as defined in any one of claims 9-15, comprising hyaluronic acid.
17. The pharmaceutical composition as defined in any one of claims 9-16, further comprising at least one compound selected from the group consisting of alpha-bisabolol, zinc pidolate, allantoin and piroctone olamine.
18. The pharmaceutical composition as claimed in any one of claims 9-17, in which the active ingredients are present in the following concentrations:

a. proanthocyanidins in the form of complexes with phospholipids:
0.01% to 1%;

b. glycyrrhetinic acid: 0.1% to 5%;
c. telmesteine: 0.01% to 1%.
19. The pharmaceutical composition as claimed in claim 18 which glycyrrhetinic acid is present in concentrations ranging from 1 to 2%.
20. A pharmaceutical composition as claimed in any one of claims 9-19 for use in therapy.
CA2481770A 2002-04-09 2003-03-31 Topical pharmaceutical compositions comprising proanthocyanidins for the treatment of dermatitis Expired - Lifetime CA2481770C (en)

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