WO2020193742A1 - Utilisation de dianhydrohexitol pour éliminer les effets cosmétique de l'acné, des pellicules et des mauvaises odeurs - Google Patents
Utilisation de dianhydrohexitol pour éliminer les effets cosmétique de l'acné, des pellicules et des mauvaises odeurs Download PDFInfo
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- WO2020193742A1 WO2020193742A1 PCT/EP2020/058678 EP2020058678W WO2020193742A1 WO 2020193742 A1 WO2020193742 A1 WO 2020193742A1 EP 2020058678 W EP2020058678 W EP 2020058678W WO 2020193742 A1 WO2020193742 A1 WO 2020193742A1
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- dianhydrohexitol
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- therapeutic
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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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
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- 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
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
Definitions
- the present application is in the field of cosmetics, more specifically in the field of antimicrobial and / or bacteriostatic and / or bactericidal and / or antifungal active cosmetic agents, preferably on bacterial and / or fungal strains present on the human epidermis.
- a use of isosorbide is proposed for reducing the number of bacterial or fungal strains present on the skin, in particular in the skin microbiome, responsible for acne, the formation of dandruff and the formation of bad odors; or to increase the activity of biocides already used for this purpose.
- Isosorbide or its alkylated derivatives are mentioned as a moisturizing agent for limiting the irritation induced by the anti-acne active agent that is benzoyl peroxide.
- the anti-acne active agent that is benzoyl peroxide.
- dimethylisosorbide is exemplified in topical formulations, and only as a moisturizing agent, because benzoyl peroxide is the active ingredient always used.
- the solution provided by the present invention makes it possible to solve the problems posed by a known solution that is salicylic acid or benzoyl peroxide, which have the major drawbacks of causing irritation of the epidermis, or which exhibits some recently discovered toxicity.
- a first abnormal situation is that of contamination of the skin microbiome by an external pathogenic microorganism, through contact with a contaminated environment.
- a second abnormal situation is that of the appearance of an imbalance in the interactions between the microorganisms constituting the skin microbiome, which results in the proliferation of one microorganism to the detriment of other microorganisms.
- Such proliferation may be generalized over a large area of the skin, or perhaps more localized, for example in areas of the skin richer in water and warmer, or for example on the face or scalp due to the presence nutrient reserves for said microorganisms, such as triglycerides located in the glands at the base of the hair or body hair.
- these abnormal situations also cause cosmetic inconvenience, in particular visual, tactile, or olfactory, which can adversely affect the comfort of the individual or his image, and thus disrupt or degrade his social life.
- the bacterial microorganism Propionobacterium acnes is responsible for acne.
- Acne is a skin disorder characterized by excessive secretion of sebum by the sebaceous glands. The sebum reaches the surface of the skin through the duct of the hair follicle. The excessive presence of sebum blocks the passage of the hair follicle duct. This causes a thickening of the sebum, which then forms a comedo (black point, or white point).
- This comedo is contaminated by the skin microbiome, including in particular the bacterium Propionobacterium acnes. The latter grows and multiplies in the sebum accumulated in the comedo.
- Sebum is indeed a nutritional source for this bacterium, which then releases metabolites in the pore of the skin. These chemicals alert and attract white blood cells, which leads to inflammation, visible by redness for example in comedones, and felt by itchy skin, more particularly localized on acne comedones.
- Inflammation can damage collagen-producing cells.
- a drop in collagen production can cause thinning of the skin, which causes hollow scars (also called depressed scars).
- the inflammation causes an increase in collagen production, which causes the scars to thicken.
- the present invention improves the structure of scars while preventing redness and itching.
- the fungal microorganisms of the Malassezia spp family are responsible for the formation of dandruff (Frederick Manuel, S Ranganathan. A new postulate on two stages of drandruff: a clinical perspective. Int J Trichology.
- Malassezia are microscopic yeasts naturally present on the surface of the skin. They are particularly abundant in areas of the body rich in sebaceous glands such as the scalp. Half of those affected do not experience the consequences of malassezia, while the other suffers from excessive development of dandruff.
- Therapeutic treatments for dandruff generally aim to eliminate the dandruff formed, or to inhibit the overproduction of immature keratinocytes, or to inhibit the growth of fungal microorganisms involved in the mechanism of dandruff formation, in particular Malassezia spp. They are based, for example, on the use of salicylic acid, or of antimycotic active agents with good antifungal activity on Malassezia spp, substances based on charcoal, sulfur or selenium disulphide.
- Salicylic acid for example, causes irritation of the scalp. Most classic antimycotics have poor elimination from the kidneys.
- sweat contains many organic substances, such as fats, amino acids, sugars, lactic acid, and urea.
- Freshly formed sweat is odorless.
- the typical smell of sweat is only formed under the action of bacteria in the skin microbiome, which break down sweat into odorous substances.
- bacteria-like microorganisms such as Corynobacterium xerosis and Staphylococcus epidermis, and yeasts such as Malassezia contribute to the formation of bad body odor, by degrading body sweat and its components, into odorous chemicals such as Amino or sulfur compounds, often perceived as unpleasant odors, even nauseating.
- antimicrobial substances also called bactericides, are used in deodorant and antiperspirant cosmetics, with the aim of controlling the growth of bacteria responsible for odor formation, often perceived as bad or foul-smelling.
- non-derivative dianhydrohexitols preferably isosorbide
- the use according to the invention makes it possible to inhibit the growth of pathogenic bacterial and / or fungal strains involved in acne, the formation of dandruff and the formation of bad body odors, on the human epidermis, up to the disappearance of these strains from the human epidermis.
- the present invention relates to the use of at least one dianhydrohexitol as a bacteriostatic or / and bactericidal and / or antifungal agent.
- at least one dianhydrohexitol has:
- the present invention relates to the non-therapeutic cosmetic use of at least one dianhydrohexitol to promote the elimination of the cosmetic effects of acne.
- the cosmetic effects of acne being chosen from inflammation or itching.
- the invention also relates to dianhydrohexitol for its use in the therapeutic treatment of acne.
- dianhydrohexitol is isosorbide.
- isosorbide for reducing or eliminating strains of Propionobacterium acnes (also called Cutibacterium acnes) of the human microbiome, and also alleviate or eliminate the cosmetic symptoms of acne, including redness, irritation and itching.
- the use according to the invention makes it possible to reduce or eliminate the inflammation, visible by redness for example in the area of acne comedones, and / or reduce or eliminate the skin itching localized on the comedones of acne.
- the dianhydrohexitol is chosen from isosorbide, isomannide, isoidide, preferably isosorbide.
- the concentration of dianhydrohexitol applied to the skin is at least 1 mg / cm 2 , preferably at least 25 mg / cm 2 , and most preferably at least 50 mg / cm 2 .
- dianhydrohexitol exhibits antimicrobial action. More particularly, dianhydrohexitol exhibits bacteriostatic and / and bactericidal and / or antifungal action, by reducing or preventing the development, or by eliminating the presence of bacterial and / or fungal strains involved in acne, preferably the presence of bacterial strains .
- the bacterial strain is chosen from commensable propionic bacteria, the genus of which is commonly called Propionobacterium spp, preferentially the bacterial strain is Propionobacterium acnes.
- dianhydrohexitol is an agent for combating the undesirable effects on the skin of commensal propionic bacteria, preferably of the genus Propionobacterium spp, and very preferably of Propionobacterium acnes.
- the use of at least one dianhydrohexitol can be done in combination with at least one other cosmetic or dermatological active agent having the same activity or function.
- the present invention relates to the non-therapeutic cosmetic use of at least one dianhydrohexitol to promote the elimination of cosmetic effects. excessive scaling.
- the cosmetic effects of excessive desquamation being chosen from inflammation or itching.
- the invention also relates to dianhydrohexitol for its therapeutic use in the treatment of dandruff.
- dianhydrohexitol is isosorbide.
- isosorbide for reducing or eliminating strains of Malassezia furfur from the human microbiome, in order to eliminate dandruff from the scalp, or to reduce its formation, or to make them less visible by reducing their size or number
- the use according to the invention makes it possible to remove dandruff from the scalp, or to reduce its formation, or to make them less visible by reducing the size or the number thereof.
- the dianhydrohexitol is chosen from isosorbide, isomannide, isoidide, preferably isosorbide.
- the concentration of dianhydrohexitol applied to the skin is at least 1 mg / cm 2 , preferably at least 25 mg / cm 2 , and most preferably at least 50 mg / cm 2 .
- dianhydrohexitol exhibits antimicrobial action. More particularly, dianhydrohexitol exhibits a bacteriostatic or / and bactericidal and / or antifungal action, by reducing or preventing the development, or by eliminating the presence of bacterial and / or fungal strains involved in excessive desquamation of the skin, preferably in the skin. formation of dandruff of the scalp.
- the fungal strain is chosen from fungal strains of the Malassezia spp family, preferably the fungal strain is Malassezia furfur.
- dianhydrohexitol is an agent for combating the adverse effects on the skin and the scalp of fungal strains of the Malassezia spp family, preferably on the bacterial strain Malassezia furfur.
- these undesirable effects there is the formation of dandruff as mentioned above, but also tinea versicolor, seborrheic dermatitis and pityrosporum folliculitis.
- the use of at least one dianhydrohexitol can be carried out in combination with at least one other cosmetic or dermatological active agent having the same activity or function.
- the present invention relates to the non-therapeutic cosmetic use of at least one dianhydrohexitol to reduce or prevent the formation of bad body odors, preferably bad odors resulting from the degradation of sweat.
- the invention also relates to dianhydrohexitol for its therapeutic use in the treatment of bad body odor.
- dianhydrohexitol is isosorbide.
- isosorbide to reduce or eliminate strains of Corynebacterium xerosis, and Staphylococcus epidermis from the human microbiome, in order to attenuate or prevent the appearance of bad odors resulting from the degradation of sweat by these microorganisms.
- Isosorbide is used alone, or in combination with other active ingredients already used for this purpose.
- the dianhydrohexitol is chosen from isosorbide, isomannide, isoidide, preferably isosorbide.
- the concentration of dianhydrohexitol applied to the skin is at least 1 mg / cm 2 , preferably at least 25 mg / cm 2 , and most preferably at least 50 mg / cm 2 .
- dianhydrohexitol exhibits antimicrobial action. More particularly, dianhydrohexitol exhibits bacteriostatic and / and bactericidal and / or antifungal action by reducing or preventing the development, or by eliminating the presence, of bacterial and / or fungal strains involved in the formation of bad body odors.
- the bacterial strain is chosen from bacterial strains of the Corynebacterium spp family, preferentially the bacterial strain is Corynebacterium xerosis, and / or the bacterial strain is chosen from the Staphylococcus spp family, preferentially the bacterial strain is Staphylococcus epidermis, and / or the bacterial strain is chosen among the Propiobacterium spp family, the bacterial strain is preferably Propiobacterium acnes.
- dianhydrohexitol is an agent for combating the undesirable effects on the skin of bacterial strains of the Corynebacterium spp family, preferably Corynebacterium xerosis, and / or of Staphylococcus spp family, preferably is Staphylococcus epidermis, and / or of the Propiobacterium spp family, preferentially on Propiobacterium acnes.
- Corynebacterium spp family preferably Corynebacterium xerosis, and / or of Staphylococcus spp family, preferably is Staphylococcus epidermis, and / or of the Propiobacterium spp family, preferentially on Propiobacterium acnes.
- the use of at least one dianhydrohexitol can be done in combination with at least one other cosmetic or dermatological active having the same activity or function.
- the aqueous solution in question may contain a dianhydrohexitol alone, as it may contain several.
- dianhydrohexitols (1, 4 - 3,6-dianhydrohexitols) are isosorbide (1, 4-3,6-dianhydrosorbitol), isomannide (1, 4- 3,6-dianhydromannitol), isoidide (1, 4-3,6-dianhydroiditol) and mixtures of at least two of these products.
- the aqueous solution contains only one dianhydrohexitol which is isosorbide.
- dianhydrohexitols are synthesized in the presence of water (or water is generated during their synthesis): by recovering said dianhydrohexitol in this reaction medium, there is immediately available a composition in the form of an aqueous solution of dianhydrohexitol which can be used according to the invention.
- the solutions of dianhydrohexitols can in particular be obtained according to the processes described in the aforementioned patent applications EP 1 287 000 and WO 03 / 043959.
- the dianhydrohexitol is chosen from isosorbide, isomannide, isoidide, preferably isosorbide.
- composition intended to be brought into contact with the skin, human or animal.
- the cosmetic or dermatological preparation according to the invention comprises, as active agent for the non-therapeutic treatment of acne, at least one dianhydrohexitol, preferably chosen from isosorbide, isomannide, isoidide, preferably is isosorbide .
- the cosmetic or dermatological preparation according to the invention comprises, as active agent for the non-therapeutic treatment of dandruff, at least one dianhydrohexitol, preferably chosen from isosorbide, isomannide, isoidide, preferably isosorbide.
- the cosmetic or dermatological preparation for topical use according to the invention comprises, as an active agent for the non-therapeutic treatment of bad odors, at least one dianhydrohexitol, preferably chosen from isosorbide, isomannide, isoidide, preferably is l isosorbide.
- the concentration of dianhydrohexitol applied to the skin or the scalp is at least 1 mg / cm2, preferably at least 25 mg / cm2, and most preferably at least 50 mg / cm2 .
- the cosmetic or dermatological preparation according to the invention comprises from 0.1% to 50% by weight of dianhydrohexitol, preferably from 0.5 to 25%, more preferably from 1% to 25% , even more preferably from 2% to 15%, and most preferably from 5% to 9%.
- the cosmetic or dermatological preparation according to the invention contains as only antimicrobial agent and / or bactericide and / or bacteriostatic and / or antifungal, at least one dianhydrohexitol, preferably chosen from isosorbide, isomannide, isoidide, preferably is isosorbide.
- the cosmetic or dermatological preparation according to the invention makes it possible to reduce or eliminate redness and / or itching due to acne, to remove dandruff from the scalp, or to attenuate its formation, or to make them less visible by reducing their size or number, reducing or preventing the formation of bad body odors, preferably bad odors resulting from the degradation of sweat.
- the cosmetic preparation can be a product for the skin, a product for the hair, a make-up, or a hygiene product.
- the cosmetic preparation according to the invention can be chosen from day creams, sunscreens, after-sun creams, self-tanners, masks.
- the cosmetic preparation according to the invention is preferably chosen from shampoos, conditioners (creams, masks, lotions), styling products (spray, gels, waxes), coloring products.
- the cosmetic preparation according to the invention is preferably chosen from foundations and eye shadows.
- the cosmetic preparation according to the invention is preferably chosen from washing gels, shower gels, cleansing or make-up removing wipes, hydroalcoholic solutions or gels, soaps, deodorants, antiperspirants, sprays for the body, more preferably among deodorants or antiperspirants, which may be in the form of a stick, gel, powder or spray.
- the cosmetic or dermatological preparation can in particular be chosen from anti-acne creams or lotions.
- the cosmetic or dermatological preparation can in particular be chosen from anti-dandruff shampoos, anti-dandruff body and hair shower gels. [0062] Method of non-therapeutic treatment
- the invention proposes a non-therapeutic cosmetic method for caring for the skin or the scalp, comprising the following steps:
- a cosmetic or dermatological preparation comprising at least one dianhydrohexitol, preferably isosorbide, before, during or after the appearance of the cosmetic effects of acne or bad odors or dandruff, for a period of at least 20 minutes, preferably at least 2 hours, and most preferably at least 6 hours,
- the invention provides a non-therapeutic cosmetic method of caring for acne-prone skin, which comprises the steps:
- a cosmetic or dermatological preparation comprising at least one dianhydrohexitol, preferably isosorbide, before, during or after the appearance of the cosmetic effects of acne, for a period of at least 20 minutes, preferably at least 2 hours, and most preferably at least 6 hours,
- the invention provides a non-therapeutic cosmetic method of scalp care, which comprises the steps:
- a cosmetic or dermatological preparation comprising at least one dianhydrohexitol, preferably isosorbide, before, during or after the appearance of dandruff, for a period of at least 20 minutes, preferably of at least 2 hours, and most preferably at least 6 hours,
- the invention provides a non-therapeutic cosmetic method of caring for skin prone to bad odors, in particular linked to the degradation of sweat by the skin microbiome, comprising the steps: - cleaning of the skin,
- a cosmetic or dermatological preparation comprising at least one dianhydrohexitol, preferably isosorbide, preferably under the arms or on the crotch, before, during or after the appearance of bad odors, for a period of time. at least 20 minutes, preferably at least 2 hours, and most preferably at least 6 hours,
- Example 1 In-vitro measurements of the effect of isosorbide on microbial strains responsible for acne
- Samples and controls are contaminated with a bacterial strain Propionibacterium acnes from about 1 to 5 43.10 4 15.10 5 colony forming units per milliliter, denoted cfu / ml.
- the samples are carefully mixed by cycles of aspiration - repression in order to ensure a homogeneous distribution of the micro-organism. The whole is incubated at 22 ° C for 28 days.
- Samples and counts of the microbial population are carried out at 24 hours, 7, 14, 21 and 28 days for the bacterial strain Propionobacterium acnes.
- the contaminated samples are taken and then deposited in serial dilutions in microtiter plates, in the presence of culture medium, which is a 0.85% saline solution of sodium chloride, and a reagent revealing dehydrogenase activity, which is 2,3,5-triphenyltetrazolium chloride (noted TTC).
- TTC 2,3,5-triphenyltetrazolium chloride
- the measurements of microbial populations carried out at each sampling time are expressed in colony-forming units / ml.
- Isosorbide is a bactericide of the Propionobacterium acnes strain.
- Example 2 In-vitro measurements of the effect of isosorbide on microbial strains responsible for dandruff
- the samples are prepared under sterile conditions and deposited in microplates (2 ml wells) according to the concentrations below. Two analysis witnesses were carried out: - a positive control corresponding to 0.5% Phenonip®;
- Samples and controls are infected with a fungal strain Malassezia furfur at about 1, 4 to 50.10 3,80.10 4 colony forming units per milliliter, denoted cfu / ml.
- the samples are carefully mixed by cycles of aspiration - repression in order to ensure a homogeneous distribution of the micro-organism. The whole is incubated at 22 ° C for 28 days.
- Samples and counts of the microbial population are carried out at 24 hours, 7, 14, 21 and 28 days for the bacterial strain.
- the contaminated samples are taken and then deposited in serial dilutions in microtiter plates, in the presence of culture medium, which is a 0.85% saline solution of sodium chloride, and a reagent revealing dehydrogenase activity, which is 2,3,5-triphenyltetrazolium chloride (denoted TTC).
- culture medium which is a 0.85% saline solution of sodium chloride
- dehydrogenase activity which is 2,3,5-triphenyltetrazolium chloride
- the measurements of microbial populations in the samples taken at each time are carried out according to the following microtiter method, for a sample.
- 20 ⁇ L of the sample are diluted by a factor of 10 by dispersion in 180 ⁇ L of Letheen broth (Difco, ref 268110) containing 1.5% of Tween 80 (Sigma , ref P1754) and TTC (Sigma, ref T8877).
- the microplate is incubated 48 hours at 32.5 ° C, and the growth of the microorganisms is followed by the color change from colorless to red / pink.
- the highest reciprocal dilution indicating growth allows determination of the log number of each microorganism at each time point.
- the isosorbide made it possible to kill the entire inoculum.
- Isosorbide is a bactericide of the Malassezia furfur strain.
- Example 3 In-vitro measurements of the effect of isosorbide on microbial strains responsible for bad body odor
- Samples and controls are contaminated with three bacterial strains, Staphylococcus epidermidis, Corynebacterium xerosis and Propionibacterium acnes from about 1 to 5 43.10 4 15.10 5 colony forming units per milliliter, denoted cfu / ml.
- the samples are carefully mixed by cycles of aspiration - repression in order to ensure a homogeneous distribution of the micro-organism. The whole is incubated at 22 ° C for 28 days.
- Samples and counts of the microbial population are carried out at 24 hours, 7, 14, 21 and 28 days for each bacterial strain.
- the contaminated samples are taken and then deposited in serial dilutions in microtiter plates, in the presence of culture medium, which is a 0.85% saline solution in sodium chloride, and a reagent revealing the activity.
- culture medium which is a 0.85% saline solution in sodium chloride, and a reagent revealing the activity.
- dehydrogenase which is 2,3,5-triphenyltetrazolium chloride (noted TTC).
- TTC 2,3,5-triphenyltetrazolium chloride
- the measurements of microbial populations in the samples taken at each time are carried out according to the following microtiter method, for a sample.
- 20 ⁇ L of the sample are diluted by a factor of 10 by dispersion in 180 ⁇ L of Letheen broth (Difco, ref 268110) containing 1.5% of Tween 80 (Sigma , ref P1754) and TTC (Sigma, ref T8877).
- the microplate is incubated 48 hours at 32.5 ° C, and the growth of the microorganisms is followed by the color change from colorless to red / pink.
- the highest reciprocal dilution indicating growth allows determination of the log number of each microorganism at each time point.
- the measurements of microbial populations carried out at each sampling time are expressed in colony-forming units / ml.
- Isosorbide is a bactericide of the Propionobacterium acnes strain.
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Abstract
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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JP2021557509A JP7547361B2 (ja) | 2019-03-28 | 2020-03-27 | 静菌用及び/又は殺菌用及び/又は抗真菌用の薬剤。 |
KR1020217032572A KR20210145760A (ko) | 2019-03-28 | 2020-03-27 | 여드름, 비듬 및 악취의 미용적 영향을 없애기 위한 다이언하이드로헥시톨의 용도 |
CN202080021064.3A CN114096229B (zh) | 2019-03-28 | 2020-03-27 | 双脱水己糖醇用于消除痤疮、头皮屑和异味对仪容仪表的影响的用途 |
EP20713025.3A EP3946235A1 (fr) | 2019-03-28 | 2020-03-27 | Utilisation de dianhydrohexitol pour éliminer les effets cosmétique de l'acné, des pellicules et des mauvaises odeurs |
US17/593,727 US20220193025A1 (en) | 2019-03-28 | 2020-03-27 | Use of dianhydrohexitol to eliminate the cosmetic effects of acne, dandruff and bad odors |
JP2024076557A JP2024102278A (ja) | 2019-03-28 | 2024-05-09 | ざ瘡、頭垢及び悪臭の美容上の影響を排除するためのジアンヒドロヘキシトールの使用 |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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FR1903286A FR3094215B1 (fr) | 2019-03-28 | 2019-03-28 | Utilisation de dianhydrohexitol pour éliminer les effets cosmétique de l’acné |
FR1903288A FR3094218B1 (fr) | 2019-03-28 | 2019-03-28 | Utilisation de dianhydrohexitol pour éliminer les effets cosmétique des pellicules |
FR1903286 | 2019-03-28 | ||
FR1903288 | 2019-03-28 | ||
FR1903289A FR3094216B1 (fr) | 2019-03-28 | 2019-03-28 | Utilisation de dianhydrohexitol pour éliminer les effets cosmétique des mauvaises odeurs |
FR1903289 | 2019-03-28 |
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WO2020193742A1 true WO2020193742A1 (fr) | 2020-10-01 |
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US (1) | US20220193025A1 (fr) |
EP (1) | EP3946235A1 (fr) |
JP (2) | JP7547361B2 (fr) |
KR (1) | KR20210145760A (fr) |
CN (1) | CN114096229B (fr) |
WO (1) | WO2020193742A1 (fr) |
Citations (10)
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US999300A (en) | 1911-04-17 | 1911-08-01 | Alvin W Collins | Letter-binder. |
US6433024B1 (en) | 2000-05-08 | 2002-08-13 | Karl F. Popp | Topical anti-acne composition |
EP1287000A1 (fr) | 2000-06-09 | 2003-03-05 | Roquette Frˬres | Procede de purification d'une composition contenant au moins un produit de deshydratation interne d'un sucre hydrogene |
WO2003043959A1 (fr) | 2001-11-20 | 2003-05-30 | Roquette Freres | Procede de preparation d'une composition contenant au moins un produit de deshydratation interne d'un sucre hydrogene |
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2020
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JP2024102278A (ja) | 2024-07-30 |
JP7547361B2 (ja) | 2024-09-09 |
CN114096229B (zh) | 2024-02-09 |
EP3946235A1 (fr) | 2022-02-09 |
US20220193025A1 (en) | 2022-06-23 |
KR20210145760A (ko) | 2021-12-02 |
JP2022526951A (ja) | 2022-05-27 |
CN114096229A (zh) | 2022-02-25 |
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