WO1998017265A1 - Composition pharmaceutique contenant de la tromethamine pour le traitement topique de l'acne simple - Google Patents
Composition pharmaceutique contenant de la tromethamine pour le traitement topique de l'acne simple Download PDFInfo
- Publication number
- WO1998017265A1 WO1998017265A1 PCT/IT1997/000239 IT9700239W WO9817265A1 WO 1998017265 A1 WO1998017265 A1 WO 1998017265A1 IT 9700239 W IT9700239 W IT 9700239W WO 9817265 A1 WO9817265 A1 WO 9817265A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tromethamine
- realization
- composition according
- grams
- stearyl
- Prior art date
Links
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229960000281 trometamol Drugs 0.000 title claims abstract description 34
- 238000011282 treatment Methods 0.000 title claims abstract description 18
- 230000000699 topical effect Effects 0.000 title claims abstract description 17
- 206010000496 acne Diseases 0.000 title claims abstract description 16
- 208000002874 Acne Vulgaris Diseases 0.000 title claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 6
- 239000006071 cream Substances 0.000 claims abstract description 9
- 239000006210 lotion Substances 0.000 claims abstract description 7
- 235000013336 milk Nutrition 0.000 claims abstract description 5
- 210000004080 milk Anatomy 0.000 claims abstract description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000008347 soybean phospholipid Substances 0.000 claims description 4
- 239000008267 milk Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 208000010444 Acidosis Diseases 0.000 description 3
- 206010039792 Seborrhoea Diseases 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000007950 acidosis Effects 0.000 description 3
- 208000026545 acidosis disease Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000262 estrogen Substances 0.000 description 3
- 229940011871 estrogen Drugs 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000002085 irritant Substances 0.000 description 3
- 231100000021 irritant Toxicity 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 206010040844 Skin exfoliation Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 230000001530 keratinolytic effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 238000009121 systemic therapy Methods 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 241000186427 Cutibacterium acnes Species 0.000 description 1
- 241001464974 Cutibacterium avidum Species 0.000 description 1
- 241001464975 Cutibacterium granulosum Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010014523 Embolism and thrombosis Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- 206010039580 Scar Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 206010042566 Superinfection Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 239000000058 anti acne agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940124340 antiacne agent Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002612 cardiopulmonary effect Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 239000003410 keratolytic agent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 230000003821 menstrual periods Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 208000017983 photosensitivity disease Diseases 0.000 description 1
- 231100000434 photosensitization Toxicity 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000011125 single therapy Methods 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
Definitions
- the present invention concerns a pharmaceutical composition containing tromethamine for the topical treatment of acne vulgaris.
- Tromethamine behaves as a weak base characterized by a significant buffer action.
- a 0.3 molar solution (3.6% solution - 36 g/litre) is iso-osmolar with human plasma and has a pH of about 8.
- tromethamine has been employed in the synthesis of surface-active agents and of vulcanisation accelerators. In cosmetics, it is used as an emulsifying agent for creams and lotions. In medical therapy tromethamine is used in the treatment of metabolic, respiratory, diabetic and post-operative acidosis; in acidosis during the cardiopulmonary bypass, in heart failure and shock. In all these therapeutic uses, tromethamine is employed in the form of a 0.3 molar watery solution.
- Acne vulgaris is one of the most common dermatological affection that strikes 25% of the youth between 12 and 20 years in variable measure. As in its most serious forms, which are not infrequent, acne vulgaris may cause disfiguring scars, it is in fact a disease with large psychical implications that may result in social maladjustment and self-isolation.
- the topical therapy is based on the use of compounds against seborrhoea compositions with keratolytic action (benzoyl peroxide) , with a basis of retinoic acid, estrogens and topical corticosteroids .
- Topical preparations against seborrhoea in general are available in a huge variety of lotions, creams, powders containing sulphur, salicylic acid and resorcinol.
- the majority of these products are irritant when applied onto the skin, and the best results are obtained when they are used with they produce a non- damaging exsiccation and an exfoliation of the affected skin.
- a too limited use offers a very limited advantage, while an excessive use may be the cause of further lesions and pain. All these products might induce further seborrhoea.
- Benzoyl peroxide acts as an exfoliating and a keratolytic agent. Therapeutic results are not obtained before 5-6 weeks. This treatment may produce skin irritation at various degrees and eczema.
- Retinoic acids acts against the creation of comedones.
- the greatest handicap of this product is its irritating action that, during the first month of treatment or even further, may cause a deterioration of the lesions, with erythema and desquamation, and such collateral effects might lead to a suspension of the therapy.
- the effectiveness of the treatment with chemotherapeutic agents and antibiotics is debatable, as there might occur photo- sensitization and modification of the bacterial flora.
- the hormonic therapy has several drawbacks. First of all, male patients are excluded from the treatment; secondly, therapeutic effects are detectable only after months; finally, the best results are obtained using preparations with a higher level of estrogens, which yet present the greatest risks of thrombosis and embolism. Usually the hormonic therapy is employed in young female patients with acne clearly becoming acute in pre-menstrual periods.
- the present invention derives from the discovery that tromethamine and its pharmacologically acceptable salts, such as acetate, carbonate, citrate, phosphate, succinate and sulfate, administered in topical applications, are extremely effective anti-acne agents, not presenting the considerable side effects of known medicines .
- a pharmaceutical composition according to above scientific and experimental discovery comprising tromethamine and/or its pharmacologically acceptable salts in preparations for topical use such as creams, emulsions, solutions, lotions, in spray containers and similar.
- compositions are given per 100 g of their formulation.
- Spray composition tromethamine gr. 3.60 citric acid " 0.65 cetyl-stearyl-ethoxylate alcohol " 2.00 water " 83.70 freon 12 - Freon 114 (15/85) " 10.00
- Cream composition tromethamine gr. 3.60 citric acid " 0.65 silicon oil “ 0.15 soya lecithin “ 1.00 sodium stearyl lactilate “ 1.50 cetyl-stearyl-ethoxylate alcohol “ 14.00 propylene glycol “ 4.00 glycerin “ 2.00 nipasept " 0.15 water " 73.00
- 0.3 molar watery solutions may also be used.
- composition according to the present invention has been tested, using a 3.6% tromethamine solution (thamesol of Baxter hydroxymethyl - aminomethane 0.3 M - Acetic acid 0.1
- the clinical varieties treated were mixed forms of acne microcystica-comedonica and papulo-pustulosa, with a wide range of seriousness and extension of skin lesions.
- the medication On the dry face, the medication is applied and the skin is gently rubbed with wads watered with abundant tromethamine solution on all the points concerned.
- the application for a few minutes of a pledget soaked with solution has proved to be effective; the skin may dry at ambient air.
- the skin shows a definitely less greasy appearance; its surface is smoother and more regular; its colour is clearer and more uniform.
- the results further improve with a total "restitutio ad integrum" of the dermal tissue.
- tromethamine and its pharmacologically acceptable salts perform a progressive and constant therapeutical action in the topical treatment of acne vulgaris .
- the first event is shown by a rapid halt to the evolution of cutaneous lesions, followed by a constant regression, up to the complete remission, of the objective symptomatology. Such an effect is most evident towards the inflammatory component.
- the rectification of the abnormally lowered pH may determine the inhibition of those enzymatic activities (in particular, phospholipases) with an optimum in acid media (pH 5-6) , which give rise to the liberation of free fat acids.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Abstract
Cette composition pharmaceutique de trométhamine permet le traitement topique de l'acné simple grâce à la réalisation de crèmes, de laits, de lotions et similaires, contenant de 1 à 10 grammes de trométhamine par 100 grammes de produit.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITCA960022 IT1288708B1 (it) | 1996-10-17 | 1996-10-17 | Composizione farmaceutica comprendente trometamina per il trattamento per via topica dell'acne vulgaris. |
| ITCA96A000022 | 1996-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1998017265A1 true WO1998017265A1 (fr) | 1998-04-30 |
Family
ID=11347108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IT1997/000239 WO1998017265A1 (fr) | 1996-10-17 | 1997-10-06 | Composition pharmaceutique contenant de la tromethamine pour le traitement topique de l'acne simple |
Country Status (2)
| Country | Link |
|---|---|
| IT (1) | IT1288708B1 (fr) |
| WO (1) | WO1998017265A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018177778A (ja) * | 2017-04-10 | 2018-11-15 | 花王株式会社 | 皮膚洗浄剤組成物 |
| CN110494120A (zh) * | 2017-04-10 | 2019-11-22 | 花王株式会社 | 去除角栓的方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994021271A1 (fr) * | 1993-03-19 | 1994-09-29 | Cellegy Pharmaceuticals, Inc. | Procedes et compositions pour induire une separation de phase des deux couches lipidiques de l'epithelium |
| US5352389A (en) * | 1991-07-08 | 1994-10-04 | Crinos Industria Farmacobiologica Spa | Composition for the cleaning of the skin, scalp and hair |
| WO1995000176A1 (fr) * | 1993-06-18 | 1995-01-05 | Allergan, Inc. | Compositions pour le traitement des complications oculaires associees a l'hypoxie |
| WO1995033489A1 (fr) * | 1994-06-07 | 1995-12-14 | Allergan | Composition de gel stable pour le traitement topique de maladies de la peau |
| WO1996014055A1 (fr) * | 1994-11-04 | 1996-05-17 | The Procter & Gamble Company | Hydrolyse acide ou basique d'emulsions tamponnees contenant des composes actifs |
-
1996
- 1996-10-17 IT ITCA960022 patent/IT1288708B1/it active IP Right Grant
-
1997
- 1997-10-06 WO PCT/IT1997/000239 patent/WO1998017265A1/fr active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5352389A (en) * | 1991-07-08 | 1994-10-04 | Crinos Industria Farmacobiologica Spa | Composition for the cleaning of the skin, scalp and hair |
| WO1994021271A1 (fr) * | 1993-03-19 | 1994-09-29 | Cellegy Pharmaceuticals, Inc. | Procedes et compositions pour induire une separation de phase des deux couches lipidiques de l'epithelium |
| WO1995000176A1 (fr) * | 1993-06-18 | 1995-01-05 | Allergan, Inc. | Compositions pour le traitement des complications oculaires associees a l'hypoxie |
| WO1995033489A1 (fr) * | 1994-06-07 | 1995-12-14 | Allergan | Composition de gel stable pour le traitement topique de maladies de la peau |
| WO1996014055A1 (fr) * | 1994-11-04 | 1996-05-17 | The Procter & Gamble Company | Hydrolyse acide ou basique d'emulsions tamponnees contenant des composes actifs |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018177778A (ja) * | 2017-04-10 | 2018-11-15 | 花王株式会社 | 皮膚洗浄剤組成物 |
| CN110494120A (zh) * | 2017-04-10 | 2019-11-22 | 花王株式会社 | 去除角栓的方法 |
| EP3610848A4 (fr) * | 2017-04-10 | 2021-01-06 | Kao Corporation | Composition d'agent nettoyant pour la peau |
| EP3610849A4 (fr) * | 2017-04-10 | 2021-01-13 | Kao Corporation | Procédé d'élimination des points noirs |
| US11406576B2 (en) | 2017-04-10 | 2022-08-09 | Kao Corporation | Method for removing keratotic plugs |
| US11975086B2 (en) | 2017-04-10 | 2024-05-07 | Kao Corporation | Method for removing keratotic plugs |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1288708B1 (it) | 1998-09-23 |
| ITCA960022A1 (it) | 1998-04-17 |
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