WO2010004016A1 - Use of phenoxyalkylamines in cosmetic and/or dermatological compositions - Google Patents
Use of phenoxyalkylamines in cosmetic and/or dermatological compositions Download PDFInfo
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- WO2010004016A1 WO2010004016A1 PCT/EP2009/058781 EP2009058781W WO2010004016A1 WO 2010004016 A1 WO2010004016 A1 WO 2010004016A1 EP 2009058781 W EP2009058781 W EP 2009058781W WO 2010004016 A1 WO2010004016 A1 WO 2010004016A1
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- WIPO (PCT)
- Prior art keywords
- acid
- composition
- compound
- formula
- phenoxyethylamine
- Prior art date
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- IMLAIXAZMVDRGA-UHFFFAOYSA-N NCCOc1ccccc1 Chemical compound NCCOc1ccccc1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/16—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring not being further substituted
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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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the invention relates to the use of compounds of the phenoxyalkylamine family of formula (I) in cosmetic and/or dermatological compositions, especially as preserving agents.
- the invention also relates to compositions comprising, especially as preserving agent, at least one phenoxyalkylamine of formula (I).
- compositions especially need to be protected against microorganisms that are capable of growing inside the composition and also against those that the user might introduce therein by handling it, in particular when taking up with the fingers products in jars.
- Commonly used chemical preserving agents are especially parabens or formaldehyde-releasing compounds.
- these preserving agents have the drawback of causing irritation, in particular on sensitive skin, when they are present in relatively large amounts.
- Known preserving agents that may be mentioned include organic hydroxy acids. However, these compounds may also give rise to irritation due to their desquamating effect on the skin, which is not always well tolerated.
- the aim of the present invention is to propose novel preserving agents that especially have a broad antimicrobial spectrum, and that do not have the drawbacks of the prior art.
- one subject of the present invention is the use of at least one compound of the phenoxyalkylamine family corresponding to formula (I)
- the compounds of formula (I) according to the invention are used as antimicrobial and/or antibacterial and/or antifungal agents.
- Another subject of the invention is a process for preserving a cosmetic and/or dermatological composition, characterized in that it consists in incorporating into the said composition at least one compound of the phenoxyalkylamine family of formula (I) as defined hereinbelow.
- the organic acid is citric acid.
- the organic acid is lactic acid (enantiomerically pure or racemic).
- Another subject of the invention is a process for preparing a compound as defined above in B, comprising: a) a step of chemical synthesis of the said compound especially according to one of the reactions chosen from: i) alkylation of phenol with a haloalkylamide (C 2 -C 8 alkyl chain), followed by a reduction; ii) alkylation of phenol with a C 2 -C 8 dihaloalkane, followed by an amination; iii) amination via reaction of a phenoxyhaloalkane (C 2 -C 8 alkane chain) with potassium phthalimide; iv) reaction between phenol and an amino alcohol (C 2 -C 8 alcohol); or v) opening of the oxazolidine ring with phenol, followed by a hydrolysis; or, according to an alternative, the use of 2-phenoxyethylamine or 3-phenoxy- propylamine; b) a step of salification in the presence of at least one mineral acid or one organic
- the mineral acid may be chosen especially from hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid.
- the organic acid may be chosen especially from carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid (enantiomerically pure or racemic), glycolic acid, citric acid, gluconic acid, salicylic acid and tartaric acid (enantiomerically pure or racemic).
- Another subject of the invention is a cosmetic and/or dermatological composition
- a cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium, at least one compound of the phenoxyalkylamine family corresponding to formula (I) as defined previously, especially as a preserving agent.
- composition according to the invention may especially be in the form of:
- a body hygiene composition such as a shower gel, a shampoo or a deodorant
- composition according to the invention does not contain any parabens.
- alkoxybenzylamine compounds as antimicrobial agents and to use them in industrial processes, detergent formulations and cosmetic formulations.
- Phenoxyethylamine (RN: 1758-46-9) is known especially in the plastics industry. Phenoxypropylamine (RN: 7617-76-7) is also known.
- the compounds of formula (I) have the advantage of being odourless and environmentally friendly.
- the salts, especially mineral acid or organic acid salts, of the compounds of formula (I) also form part of the invention.
- a mineral acid such as hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid.
- the compounds of formula (I) according to the invention will be used in a salified form (compounds "B" according to the invention).
- This salified form is especially obtained by adding a mineral acid chosen especially from hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, or an organic acid chosen especially from carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid, glycolic acid, citric acid, gluconic acid, salicylic acid and tartaric acid.
- compound Il or III according to the invention will be used in a salified form.
- the compound 3-phenoxypropylamine (compound III), in a non-salified form, is commercially available from the company Wako (ref. F 320-31701 ).
- the invention also relates to a phenoxyhexylamine or a salt thereof, in particular a phenoxyhexylamine in citrate or lactate salified form.
- the invention relates in particular to the compound 2-phenoxyethylamine 2-hydroxypropane-1 ,2,3-tricarboxylate, also known as 2-phenoxyethylamine citrate (compound IV):
- the compound 2-phenoxyethylamine 2-hydroxypropane-1 ,2,3-tricarboxylate may especially be prepared according to the following process: - phenoxyethylamine compound (II) is synthesized according to one of the synthetic processes 1 ) to 5) described previously, or a commercial reference such as the product available from Chemrio International Limited (http://www.chemrio.com), or the product from Aldrich under the commercial reference F 40,726-7, is used; - it is placed in contact with citric acid and ethanol at room temperature for
- the invention also relates in particular to the compound 2-phenoxyethylamine lactate (compound V):
- the 2-phenoxyethylamine lactate will be in proportions of 2 equivalents of phenoxyethylamine per 1 equivalent of lactic acid.
- This compound 2-phenoxyethylamine lactate (compound V) may especially be prepared according to the following process: - phenoxyethylamine (compound II) is synthesized according to one of the processes 1 ) to 5) described previously, or a commercial reference such as the product available from Chemrio International Limited (http://www.chemrio.com), or from Aldrich under the commercial reference F 40,726-7, is used; - it is placed in contact with lactic acid (racemic or enantiomerically pure) in ethyl acetate, and the mixture is left stirring at room temperature for 15 hours;
- the compounds of the phenoxyalkylamine family of formula (I) according to the invention may be present in the cosmetic or dermatological compositions in an amount sufficient to obtain the desired effect, and especially represent from 0.001 % to 30% by weight, preferably from 0.01 % to 15% by weight and more particularly from 0.1% to 5% by weight relative to the total weight of the composition.
- the composition may also comprise an aqueous medium, an aqueous-alcoholic medium containing an alcohol such as ethanol or isopropanol, or an organic medium comprising common organic solvents such as C1-C6 alcohols, especially ethanol and isopropanol, glycols such as propylene glycol, and ketones.
- an aqueous medium an aqueous-alcoholic medium containing an alcohol such as ethanol or isopropanol
- an organic medium comprising common organic solvents such as C1-C6 alcohols, especially ethanol and isopropanol, glycols such as propylene glycol, and ketones.
- the phenoxyalkylamine compounds of formula (I) used in the context of the present invention thus show noteworthy antimicrobial activity, especially antibacterial and antifungal activity.
- a makeup product for facial skin, bodily skin or the lips such as a foundation, a makeup rouge, an eyeshadow, a concealer stick, a cover stick, an eyeliner, a mascara, a lipstick, a nail varnish or a nailcare product;
- an aerosol composition also comprising a propellant under pressure
- phenoxyethylamine (RN 1758-46-9 commercially available from the company Aldrich, ref. 40,726-7) are dissolved in 2L of ethanol in a reactor equipped with a mechanical stirrer. 56.04 g of citric acid are then added. A compact precipitate rapidly forms (vigorous stirring required).
- strains of gram-negative bacteria Esscherichia coli and Pseudomonas aeruginosa
- gram-positive bacterium Enterococcus faecalis
- yeast Candida albicans
- mould Aspergillus niger
- a suspension in Tryptone salt diluent is prepared, respectively, for the bacteria and the yeast, so as to obtain by spectrophotometer a suspension with an optical density of between 35% and 45% of transmitted light at 544 nm.
- the amount of microorganisms present in the product corresponds, after homogenization, to a concentration of 10 6 microorganisms per gram of product, i.e. inoculation to 1% of an inoculum containing 10 8 microorganisms per ml.
Abstract
The invention relates to the use of compounds of the phenoxyalkylamine family of formula (I) in cosmetic and/or dermatological compositions, especially as preserving agents. The invention also relates to compositions comprising, especially as preserving agent, at least one phenoxyalkylamine of formula (I). The invention also relates to particular compounds of the phenoxyalkylamine family of formula (I) and to cosmetic and/or dermatological compositions containing them.
Description
Use of phenoxyalkylamines in cosmetic and/or dermatological compositions
The invention relates to the use of compounds of the phenoxyalkylamine family of formula (I) in cosmetic and/or dermatological compositions, especially as preserving agents.
The invention also relates to compositions comprising, especially as preserving agent, at least one phenoxyalkylamine of formula (I).
The invention also relates to particular compounds of the phenoxyalkylamine family of formula (I) and to cosmetic and/or dermatological compositions containing them.
It is common practice to introduce into cosmetic or dermatological compositions chemical preserving agents for combating the growth of microorganisms in these compositions, which would make them rapidly unsuitable for use. The compositions especially need to be protected against microorganisms that are capable of growing inside the composition and also against those that the user might introduce therein by handling it, in particular when taking up with the fingers products in jars. Commonly used chemical preserving agents are especially parabens or formaldehyde-releasing compounds. However, these preserving agents have the drawback of causing irritation, in particular on sensitive skin, when they are present in relatively large amounts. Known preserving agents that may be mentioned include organic hydroxy acids. However, these compounds may also give rise to irritation due to their desquamating effect on the skin, which is not always well tolerated.
Moreover, out of concern to preserve the environment, consumers are increasingly in search of environmentally friendly preserving agents.
There is thus still a need for preserving agents, especially antimicrobial agents, whose action is at least as effective as the compounds of the prior art, but which do not have their drawbacks.
The aim of the present invention is to propose novel preserving agents that especially have a broad antimicrobial spectrum, and that do not have the drawbacks of the prior art.
Thus, one subject of the present invention is the use of at least one compound of the phenoxyalkylamine family corresponding to formula (I)
I in which R1 represents a linear or branched saturated hydrocarbon-based chain CnH2n with n = 1 to 8, or an unsaturated hydrocarbon-based chain CnH2n-2 with n = 1 to 8, and in which the phenyl group is unsubstituted, and also salts thereof, in a cosmetic and/or dermatological composition also comprising a physiologically acceptable medium, especially as a preserving agent.
The term "preserving agent" means a substance that is commonly added to a composition in order to ensure its preservation with respect to a contaminant.
Advantageously, the compounds of formula (I) according to the invention are used as antimicrobial and/or antibacterial and/or antifungal agents.
Another subject of the invention is a process for preserving a cosmetic and/or dermatological composition, characterized in that it consists in incorporating into the said composition at least one compound of the phenoxyalkylamine family of formula (I) as defined hereinbelow.
The invention also relates to particular compounds of the phenoxyalkylamine family of formula (I), in particular: - A: the compounds of formula (I) as defined above, in which R1 represents a linear or branched saturated hydrocarbon-based chain CnH2n with n = 4 to 8, or an unsaturated hydrocarbon-based chain CnH2n-2 with n = 4 to 8, and in which the phenyl group is unsubstituted, and also salts thereof; and - B: the compounds of formula (I) as defined above, in a salified form, especially in the presence of a mineral or organic acid, preferably an organic acid.
More preferably, the organic acid is citric acid.
According to another embodiment, the organic acid is lactic acid (enantiomerically pure or racemic).
Another subject of the invention is a process for preparing a compound of formula (I), comprising: a) a step of chemical synthesis of the said compound defined above in A especially according to one of the reactions chosen from: i) alkylation of phenol with a haloalkylamide (C4-C8 alkyl chain), followed by a reduction; ii) alkylation of phenol with a C4-C8 dihaloalkane, followed by an amination; iii) amination via reaction of a phenoxyhaloalkane (C4-C8 alkane chain) with potassium phthalimide; iv) reaction between phenol and an amino alcohol (C4-C8 alcohol); or v) opening of the oxazolidine ring with phenol, followed by a hydrolysis; b) optionally, a step of salification in the presence of at least one mineral acid or one organic acid.
Another subject of the invention is a process for preparing a compound as defined above in B, comprising: a) a step of chemical synthesis of the said compound especially according to one of the reactions chosen from: i) alkylation of phenol with a haloalkylamide (C2-C8 alkyl chain), followed by a reduction; ii) alkylation of phenol with a C2-C8 dihaloalkane, followed by an amination; iii) amination via reaction of a phenoxyhaloalkane (C2-C8 alkane chain) with potassium phthalimide; iv) reaction between phenol and an amino alcohol (C2-C8 alcohol); or v) opening of the oxazolidine ring with phenol, followed by a hydrolysis; or, according to an alternative, the use of 2-phenoxyethylamine or 3-phenoxy- propylamine; b) a step of salification in the presence of at least one mineral acid or one organic acid, in particular a citric acid or a lactic acid.
The mineral acid may be chosen especially from hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid.
The organic acid may be chosen especially from carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid (enantiomerically pure or racemic), glycolic acid, citric acid, gluconic acid, salicylic acid and tartaric acid (enantiomerically pure or racemic).
Preferably, the step of salification of the said phenoxyalkylamine compounds of formula (I) according to the invention will take place in the presence of an alcohol or an alcohol ester, and in the presence of an organic acid.
These chemical reactions are described hereinbelow.
Another subject of the invention is a cosmetic and/or dermatological composition comprising, in a physiologically acceptable medium, at least one compound of the phenoxyalkylamine family corresponding to formula (I) as defined previously, especially as a preserving agent.
The said composition according to the invention may especially be in the form of:
- a makeup product for facial skin, bodily skin or the lips;
- an antisun or artificial tanning composition;
- an aftershave gel or lotion; - a hair-removing cream;
- a body hygiene composition, such as a shower gel, a shampoo or a deodorant;
- a pharmaceutical composition;
- a solid composition such as a soap or a cleansing bar;
- an aerosol composition also comprising a propellant under pressure; - a hairsetting lotion, a hairstyling cream or gel, a dye composition, a hair restructuring lotion, a permanent-waving composition or a lotion or gel for combating hair loss;
- a composition for dentibuccal use.
According to one particular embodiment, the composition according to the invention does not contain any parabens.
According to another particular embodiment, the composition according to the invention does not contain any preserving agent other than the compound(s) of the phenoxyalkylamine family of formula (I).
The Applicant has found, surprisingly and unexpectedly, that the compounds of the phenoxyalkylamine family corresponding to formula (I) according to the invention, in which the amine and the phenyl group are unsubstituted, have good antimicrobial properties, whether it is towards bacteria, yeasts or moulds. On account of their broad antimicrobial spectrum, these compounds may thus be used, especially in cosmetic compositions, as antimicrobial agents, especially as antibacterial agents, and/or as antifungal agents, i.e. as anti-yeast and/or anti-mould agents. These compounds of formula (I) may thus be used advantageously in cosmetic and/or dermatological compositions, especially as preserving agents.
It is known from the prior art to use phenoxyalkylamine derivatives, substituted on the phenyl group with halogen (e.g.: Cl or Br) or haloaryl groups and/or substituted on the amine, as dopamine receptor antagonists, for the preparation of pharmaceutical compositions for treating psychosis and schizophrenia (US 6 051 605) or as bactericides in agriculture and horticulture (US 5 409 957, EP 446 873).
It is also known to use alkoxybenzylamine compounds as antimicrobial agents and to use them in industrial processes, detergent formulations and cosmetic formulations.
It is also known to use compounds of the phenoxyalcohols family as preserving agent in cosmetic compositions (JP 2002-350791 ).
However, to the Applicant's knowledge, the phenoxyalkylamines corresponding to formula (I) according to the invention, in which the amine and the phenyl group are unsubstituted, have never been proposed in cosmetic compositions, and even less so as preserving agents.
Phenoxyethylamine (RN: 1758-46-9) is known especially in the plastics industry. Phenoxypropylamine (RN: 7617-76-7) is also known.
The compounds of formula (I) according to the invention have as an advantage a clearly defined and characterized chemical structure, resulting in easy reproducibility of their manufacture; their industrial feasibility is also relatively simple.
Furthermore, they show good solubility or compatibility with the media commonly used in cosmetics, especially aqueous media. In addition, the compounds of formula (I)
have the advantage of being odourless and environmentally friendly.
Phenoxyalkylamines of formula (I) according to the invention
The compounds of the phenoxyalkylamine family according to the invention correspond to formula (I) below:
I in which R1 represents a linear or branched saturated hydrocarbon-based chain CnH2n with n = 1 to 8, or an unsaturated hydrocarbon-based chain CnH2n-2 with n = 1 to 8, in which the phenyl group is unsubstituted, and also salts thereof.
In particular, R1 denotes an ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl divalent radical, and also the corresponding positional isomers thereof.
Compounds corresponding to formula (I) according to the invention that may be mentioned include: - 2-phenoxyethylamine (Registry number 1758-46-9)
3-phenoxypropylamine (Registry number 7617-76-7) 4-phenoxybutylamine 5-phenoxypentylamine 6-phenoxyhexylamine - 7-phenoxyheptylamine
8-phenoxyoctylamine and salts thereof.
The salts, especially mineral acid or organic acid salts, of the compounds of formula (I) also form part of the invention.
Mention may be made especially of the salts obtained by adding the compound of formula (I) according to the invention to a mineral acid such as hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid.
Mention may also be made of the salts obtained by adding the compound of formula (I) according to the invention to an organic acid such as carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid (enantiomerically pure or racemic), glycolic acid, citric acid, gluconic acid, salicylic acid or tartaric acid.
In particular, a salt obtained by adding a compound of formula (I) according to the invention to an acid selected from sulphuric acid, nitric acid, carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid, glycolic acid, citric acid, gluconic acid, salicylic acid or tartaric acid will be used.
Still in particular, a salt obtained by adding a compound of formula (I) according to the invention to an organic acid will be used.
According to one preferred embodiment, a salt obtained by adding a compound of formula (I) according to the invention to a citric acid will be used.
According to another preferred embodiment, a salt obtained by adding a compound of formula (I) according to the invention to a lactic acid (enantiomerically pure or racemic) will be used.
According to one preferred embodiment, a compound chosen from:
- 2-phenoxyethylamine (compound II) Registry number 1758-46-9
Preferably, the compounds of formula (I) according to the invention will be used in a salified form (compounds "B" according to the invention).
This salified form is especially obtained by adding a mineral acid chosen especially from hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, or an organic acid chosen especially from carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid, glycolic acid, citric acid, gluconic acid, salicylic acid and tartaric acid.
According to a first embodiment, the compounds of formula (I) according to the invention are in a citrate salified form.
According to another embodiment, the compounds of formula (I) according to the invention are in a lactate salified form.
In particular, compound Il or III according to the invention will be used in a salified form.
In particular, a salt obtained by adding the compound 2-phenoxyethylamine
(compound II) to citric acid will be used.
According to another particular embodiment, a salt obtained by adding the compound 2-phenoxyethylamine (compound II) to lactic acid (enantiomerically pure or racemic) will be used.
According to one preferred embodiment, the compounds of formula (I) are in a citrate salified form, and the compound is in particular 2-phenoxyethylamine citrate.
According to another preferred embodiment, the compounds of formula (I) are in a lactate salified form, and the compound is in particular 2-phenoxyethylamine lactate.
Preparation of the compounds of formula (I) according to the invention
The compound 2-phenoxyethylamine (compound II), in a non-salified form, is commercially available from the company Chemrio International Limited (http://www.chemrio.com), or from the company Aldrich (ref. F40, 726-7).
The compound 3-phenoxypropylamine (compound III), in a non-salified form, is commercially available from the company Wako (ref. F 320-31701 ).
These compounds corresponding to the general formula (I) may also be synthesized according to processes described in the literature: since these processes have been described for the production of phenoxyethylamine, the starting materials are adapted to the desired final product of formula (I) according to the invention.
Mention may be made especially of the processes described and referenced hereinbelow, which a person skilled in the art will know how to adapt to obtain the compounds of formula (I) according to the invention, in particular to obtain the compounds of formula (I) in which R1 represents a linear or branched saturated hydrocarbon-based chain CnH2n with n = 4 to 8, or an unsaturated hydrocarbon-based chain CnH2n-2 with n = 4 to 8.
i) Alkylation of phenol with a haloalkylamide (C1-CR alkyl chain), followed by a reduction
By way of example, mention may be made of the alkylation reaction of phenol with a haloacetamide, followed by a reduction:
with X = Cl and the reducing agent = LiAIH4, according to Helvetica Chimica Acta, 1948, 31 , 1397-1400 or the reducing agent = BH3, according to J. Med. Chem., 2003, 46(8), 1504-151 1.
The starting haloalkylamide is defined as a function of the desired final compound of formula (I) according to the invention, with X = Cl, Br and the hydrocarbon-based chain of the haloalkylamide representing an ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl.
The following will be used, for example: - a halopropylamide (e.g.: 3-chloropropylamide) to obtain phenoxypropylamine;
a chlorobutylamide (e.g.: 4-chlorobutylamide) to obtain phenoxybutylamine; a chloropentylamide (e.g.: 5-chloropentylamide) to obtain a phenoxypentylamine; a chlorohexylamide (e.g.: 6-chlorohexylamide) to obtain a phenoxyhexylamine; a chloroheptylamide (e.g.: 7-chloroheptylamide) to obtain a phenoxyheptylamine; - a chlorooctylamide (e.g.: 8-chlorooctylamide) to obtain a phenoxyoctylamine.
ii) Alkylation of phenol with a C?-Ca dihaloalkane, followed by an amination
By way of example, mention may be made of the alkylation reaction of phenol with a dihaloethane, followed by an amination, according to the following reaction:
with X = Br or X = Cl, according to Transactions of Tianjin Univ., 2006, 12(4), 248- 251.
The starting dihaloalkane is defined as a function of the desired final product of formula (I) according to the invention, with X = Cl, Br and the alkane chain representing an ethane, a propane, a butane, a pentane, a hexane, a heptane or an octane.
The following will be used, for example: - a 1 ,3-dichloropropane to obtain a phenoxypropylamine
- a 1 ,4-dichlorobutane to obtain a phenoxybutylamine
- a 1 ,5-dichloropentane to obtain a phenoxypentylamine
- a 1 ,6-dichlorohexane to obtain a phenoxyhexylamine
- a 1 ,7-dichloroheptane to obtain a phenoxyheptylamine - a 1 ,8-dichlorooctane to obtain a phenoxyoctylamine.
iii) Amination via reaction of a phenoxyhaloalkane (C?-Ca alkane chain) with potassium phthalimide
The intermediate compound obtained according to the reaction described in process 2) above may be placed in contact with potassium phthalimide to obtain a phenoxyalkylamine of formula (I) according to the invention.
By way of example, mention may be made of amination via reaction of a phenoxyhaloethane with potassium phthalimide according to the following reaction described in J. Heterocyclic Chemistry, 1982, 19(3), 537-9:
iv) Reaction between phenol and an amino alcohol (C?-Ca alcohol)
By way of example, mention may be made of the following reaction between phenol and ethanolamine, as described in preparation 13-1 of patent application WO- 2005/009 941 :
1 ) NaH/dioxane
OH 0H 2) Reflux 14 h o / 3) Chromatography NH,
^ H2N
The starting amino alcohol is defined as a function of the desired product of formula (I) according to the invention. It may thus be chosen from ethanolamine, propanolamine, butanolamine, pentanolamine, hexanolamine, heptanolamine and octanolamine.
v) Opening of the oxazolidine ring with phenol, followed by a hydrolysis
By way of example, mention may be made of the following reaction between methylimide and ethanolamine, followed by addition of phenol and a hydrolysis:
O
1) Zn(OAc)2 cat ^O^
N Λ
CH3CN + NH2CH2CH2OH O V N 1> C; H reflux, 20 h 160°C, 7 h 2) Distillation 2) Cool, filtration
1) H3PO4, reflux, 8 h
905% 71 2% or potentially NaOH/DME, reflux, 6 h industrially available 2) Extraction with toluene and distillation
^O^
NH,
80 3-98% in three steps with preparation of oxazolidine and hydrolysis with NaOH according to Jingxi Huagong Zhongjiati, 2003, 33(5), 28-29, or in two steps starting with oxazolidine and hydrolysis with H3PO4 according to Example 2 of patent application US 5 276 192.
The starting amino alcohol is defined as a function of the desired product of formula (I) according to the invention. It may thus be chosen from ethanolamine, propanolamine, butanolamine, pentanolamine, hexanolamine, heptanolamine and octanolamine.
These processes according to one of the variants i) to v) described above are especially suited to the preparation of compounds of formula (I) according to the invention, in which R1 represents a linear or branched saturated hydrocarbon-based chain CnH2n with n = 4 to 8, or an unsaturated hydrocarbon-based chain CnH2n-2 with n = 4 to 8, and salts thereof (compounds "A" according to the invention).
These compounds also form part of the invention.
The invention thus also relates to a phenoxybutylamine or a salt thereof, in particular a phenoxybutylamine in citrate or lactate salified form.
The invention also relates to a phenoxypentylamine or a salt thereof, in particular a phenoxypentylamine in citrate or lactate salified form.
The invention also relates to a phenoxyhexylamine or a salt thereof, in particular a phenoxyhexylamine in citrate or lactate salified form.
The invention also relates to a phenoxyheptylamine or a salt thereof, in particular a phenoxyheptylamine in citrate or lactate salified form.
The invention also relates to a phenoxyoctylamine or a salt thereof, in particular a phenoxyoctylamine in citrate or lactate salified form.
The invention relates in particular to the compound 2-phenoxyethylamine 2-hydroxypropane-1 ,2,3-tricarboxylate, also known as 2-phenoxyethylamine citrate (compound IV):
corresponding to the salified form in the form of 2-phenoxyethylamine citrate.
This compound is obtained by salification of phenoxyethylamine with citric acid.
2-Phenoxyethylamine citrate may comprise 1 , 2 or 3 salified functions, corresponding to the following proportions:
- 1 equivalent of phenoxyethylamine per 1/3 equivalent of citric acid (1 salified function)
- 2 equivalents of phenoxyethylamine per 2/3 equivalents of citric acid (2 salified functions)
- 3 equivalents of phenoxyethylamine per 1 equivalent of citric acid (3 salified functions).
According to one preferred embodiment, the 2-phenoxyethylamine citrate will be in the following proportions:
The compound 2-phenoxyethylamine 2-hydroxypropane-1 ,2,3-tricarboxylate (compound IV) may especially be prepared according to the following process:
- phenoxyethylamine compound (II) is synthesized according to one of the synthetic processes 1 ) to 5) described previously, or a commercial reference such as the product available from Chemrio International Limited (http://www.chemrio.com), or the product from Aldrich under the commercial reference F 40,726-7, is used; - it is placed in contact with citric acid and ethanol at room temperature for
15 hours;
- the precipitated citrate formed is filtered off, washed with ethanol and then dried (see Example 1 below).
The invention also relates in particular to the compound 2-phenoxyethylamine lactate (compound V):
This compound is obtained by salification of phenoxyethylamine with lactic acid
(enantiomerically pure or racemic).
2-Phenoxyethylamine lactate may comprise one or two salified functions, corresponding to the following proportions: - 1 equivalent of phenoxyethylamine per 1/2 equivalent of lactic acid (1 salified function),
- 2 equivalents of phenoxyethylamine per 1 equivalent of lactic acid (2 salified functions).
Preferably, the 2-phenoxyethylamine lactate will be in proportions of 2 equivalents of phenoxyethylamine per 1 equivalent of lactic acid.
This compound 2-phenoxyethylamine lactate (compound V) may especially be prepared according to the following process: - phenoxyethylamine (compound II) is synthesized according to one of the processes 1 ) to 5) described previously, or a commercial reference such as the product available from Chemrio International Limited (http://www.chemrio.com), or from Aldrich under the commercial reference F 40,726-7, is used;
- it is placed in contact with lactic acid (racemic or enantiomerically pure) in ethyl acetate, and the mixture is left stirring at room temperature for 15 hours;
- the medium is cooled to -15°C for 3 hours in total, and the precipitate is then filtered off, washed and dried (see Example 2 below).
The compounds of the phenoxyalkylamine family of formula (I) according to the invention may be present in the cosmetic or dermatological compositions in an amount sufficient to obtain the desired effect, and especially represent from 0.001 % to 30% by weight, preferably from 0.01 % to 15% by weight and more particularly from 0.1% to 5% by weight relative to the total weight of the composition.
Galenical form
The compositions comprising the said phenoxyalkylamine compounds of formula (I) according to the invention comprise a physiologically acceptable medium, i.e. a medium that is compatible with the skin and possibly with its integuments (eyelashes, nails or hair), the scalp and/or mucous membranes.
They may be in any galenical form that is suitable for topical application, especially in the form of an aqueous, aqueous-alcoholic, organic or oily solution; in the form of a suspension or dispersion in solvents or fatty substances, of lotion or serum type; in the form of a vesicular dispersion; in the form of a VWO, O/W or multiple emulsion, such as a cream or a milk; in the form of an ointment, a gel, a solid stick, pasty or solid anhydrous products, a mousse, especially an aerosol mousse, or a spray.
The physiologically acceptable medium in which the compounds may be used, and the constituents thereof, their amount, the galenical form of the composition and the method for preparing it, may be chosen by a person skilled in the art on the basis of his general knowledge as a function of the desired type of composition.
The composition may especially comprise any fatty substance usually used in the envisaged field of application. Mention may be made especially of silicone fatty substances such as silicone oils, gums and waxes, and also non-silicone fatty substances such as oils and waxes of plant, mineral, animal and/or synthetic origin. The oils may optionally be volatile or non-volatile. Mention may also be made of hydrocarbons, synthetic esters and ethers, fatty alcohols and fatty acids.
The composition may also comprise an aqueous medium, an aqueous-alcoholic medium containing an alcohol such as ethanol or isopropanol, or an organic medium comprising common organic solvents such as C1-C6 alcohols, especially ethanol and isopropanol, glycols such as propylene glycol, and ketones.
The composition may comprise at least one standard emulsifier, chosen from amphoteric, anionic, cationic and nonionic emulsifiers, used alone or as a mixture.
It may also comprise adjuvants that are common in the field under consideration, such as hydrophilic or lipophilic thickeners or gelling agents, hydrophilic or lipophilic additives, active agents, especially cosmetic active agents, antioxidants, fragrances, fillers, pigments, UV-screening agents, odour absorbers, dyes, moisturizers (glycerol), vitamins, essential fatty acids, liposoluble polymers, especially hydrocarbon-based polymers, opacifiers, stabilizers, sequestrants, conditioning agents and propellants.
Needless to say, a person skilled in the art will take care to select this or these optional additional adjuvant(s) and/or the amount thereof such that the advantageous properties of the composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
By way of example, these optional adjuvants may represent from 0.001% to 20% by weight and preferably from 0.01 % to 10% by weight relative to the total weight of the said composition.
The pH of the compositions according to the invention, when they comprise at least one aqueous phase (e.g.: aqueous solutions, emulsions, etc.), is preferably between 4 and 9, preferably between 4 and 7, advantageously from 5 to 6, and in particular a pH of 5.5.
The phenoxyalkylamine compounds of formula (I) used in the context of the present invention thus show noteworthy antimicrobial activity, especially antibacterial and antifungal activity.
It has been found that, depending on the nature of the compound of formula (I) used (salified or non-salified; choice of the salt), it is possible to obtain compounds that are more or less active towards a given type of microbe. The field of action of the
compounds according to the invention can thus be modified by focusing on a given microbe, by appropriately choosing the chemical nature of the compound used.
These compounds thus find a most particular application in compositions that may be in the form of:
- a makeup product for facial skin, bodily skin or the lips, such as a foundation, a makeup rouge, an eyeshadow, a concealer stick, a cover stick, an eyeliner, a mascara, a lipstick, a nail varnish or a nailcare product;
- an antisun or artificial tanning composition;
- an aftershave gel or lotion;
- a hair-removing cream;
- a body hygiene composition, such as a shower gel, a shampoo or a deodorant;
- a pharmaceutical composition;
- a solid composition such as a soap or a cleansing bar;
- an aerosol composition also comprising a propellant under pressure;
- a hairsetting lotion, a hairstyling cream or gel, a dye (especially an oxidation dye) composition optionally in the form of a colouring shampoo, a hair restructuring lotion, a permanent-waving composition or a lotion or gel for combating hair loss;
- a composition for dentibuccal use, for example a toothpaste.
The examples that follow illustrate the invention in greater detail without in any way limiting its scope.
EXAMPLE 1 : Preparation of 2-phenoxyethylamine 2-hydroxypropane-1 ,2,3- tricarboxylate (= 2-phenoxyethylamine citrate): compound IV
2-Phenoxyethylamine 2-hydroxypropane-1 ,2,3-tricarboxylate (compound IV)
is obtained by salification of phenoxyethylamine with citric acid, according to the following reaction:
Ethanol Citric acid
15 h room temperature phenoxyethylamine
MW = 137 18
MW = 137 18 192 13 C8H11 NO C6H8O7
120 g of phenoxyethylamine (RN 1758-46-9 commercially available from the company Aldrich, ref. 40,726-7) are dissolved in 2L of ethanol in a reactor equipped with a mechanical stirrer. 56.04 g of citric acid are then added. A compact precipitate rapidly forms (vigorous stirring required).
After stirring for 15 hours, the compact solid is filtered off on a sinter funnel and is then washed with 150 ml of ethanol. The solid obtained is dried in a desiccator under vacuum at 500C. Recovered mass: 145 g. The reaction yield is 82%.
Phenoxyethylamine (starting material) may also be prepared according to one of the processes described in the literature and indicated previously in the description (cf. hereinabove).
EXAMPLE 2: Preparation of 2-phenoxyethylamine lactate (compound V)
2-Phenoxyethylamine lactate (compound V) is obtained by salification of phenoxyethylamine with lactic acid, according to the following reaction:
10 g of phenoxyethylamine (RN 1758-46-9 available commercially from the company Aldrich, ref. 40,726-7) are dissolved in 70 ml of ethyl acetate in a reactor. 6.02 ml of D,L-lactic acid (1 equivalent) are then added and the mixture is stirred at room temperature for 15 hours. The milky medium thus obtained is cooled to -15°C for 2 hours. A precipitate forms. The mixture is maintained for a further 1 hour at -15°C and the precipitate obtained is filtered off on a sinter funnel and rinsed with 5 ml of ethyl acetate.
The solid is then dried in a desiccator under vacuum at 500C. A white wax is obtained. Recovered mass: 16.57 g. The reaction yield is 77%.
EXAMPLE 3: Measurement of the antimicrobial activity of compounds of formula (I) according to the invention in water
The antimicrobial efficacy of compounds of formula (I) according to the invention was evaluated by means of the Challenge Test method or artificial contamination after introducing the said compounds into water (Example 3) or into cosmetic formulations (Example 4).
Protocol
The challenge test method consists in artificially contaminating the sample with microbial collection strains (bacteria, yeasts and moulds) and evaluating the number of revivable microorganisms seven days after the inoculation.
In order to demonstrate the effect of compounds of formula (I), the antimicrobial activity of an aqueous solution containing, respectively, 0.75% and 0.5% of the compound 2-phenoxyethylamine (compound II); 0.50% of the compound 3- phenoxypropylamine (compound III); or 0.75%, 0.5% and 0.25%, respectively, of the compound 2-phenoxyethylamine 2-hydroxypropane-1 ,2,3-tricarboxylate, also known as 2-phenoxyethylamine citrate (compound IV), was compared with the same formulation alone (Control), after inoculation of about 106 cfu (colony-forming units)/gram of aqueous solution.
Five pure microorganism cultures are used.
ATCC = American Type Culture Collection
The strains of gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), gram-positive bacterium (Enterococcus faecalis), yeast (Candida albicans), and mould (Aspergillus niger) are inoculated in subculturing medium, the day before inoculation for the bacteria and the yeast, and five days before inoculation for the mould, respectively.
On the day of inoculation:
- a suspension in Tryptone salt diluent is prepared, respectively, for the bacteria and the yeast, so as to obtain by spectrophotometer a suspension with an optical density of between 35% and 45% of transmitted light at 544 nm.
- for the mould, spores are collected by washing the agar with 6 to 7 ml of harvest solution, and the suspension is collected in a sterile flask or tube.
After homogenizing the microbial suspension, 0.2 ml of inoculum is introduced into each pill bottle (the suspensions are used pure: between 1 x108 and 3x108 colony-forming units (cfu) per ml) and the microbial suspension is homogenized thoroughly, using a spatula, in the 20 g of product (aqueous solution containing the compounds of formula (I) according to the invention at the indicated concentrations).
The amount of microorganisms present in the product corresponds, after homogenization, to a concentration of 106 microorganisms per gram of product, i.e. inoculation to 1% of an inoculum containing 108 microorganisms per ml.
After a contact time of 7 days between the microorganisms and the product at 22°C ± 2°C and in the dark, tenfold dilutions are performed and the number of revivable microorganisms remaining in the product is counted.
Results
<200 cfu: sensitivity threshold of the method
This study shows that the compounds of formula (I) according to the invention have a very broad antimicrobial spectrum due to their antibacterial and antifungal activity.
The compounds of formula (I) according to the invention are efficient preserving agents, in particular in the aqueous solutions tested.
EXAMPLE 4: Measurement of the antimicrobial activity of the compounds of formula (I) in formulation
The same test (Challenge Test) as that described in Example 3 above is performed on cosmetic formulations. The antimicrobial activity of a cosmetic formulation containing, respectively, 0.75% of compound according to the invention (compound II, IV or V) was compared with the same formulation alone (Control), after inoculation of about
106 microorganisms/gram of cosmetic product.
Makeup-removing lotion (Control) Allantoin 0.05%
Hexylene glycol 1.00%
Sodium N-cocoylamidoethyl N-ethoxycarboxymethylglycinate 1.10%
Cornflower water 1.00%
Sodium chloride 0.90% Sodium/magnesium lauryl ether sulfate (80/20) at 52% in water 0.45%
Fragrance 0.01 %
Water qs 100%
0.75% of compound V (2-phenoxyethylamine lactate) is added to this makeup- removing lotion.
Makeup-removing milk (Control)
Acrylic acid/stearyl methacrylate copolymer polymerized in an ethyl acetate/cyclohexane mixture (Pemulen TR1® from Noveon) 0.1 %
Xanthan gum 0.1 %
2-Ethylhexyl palmitate 7.0%
Glycerol 3.0%
Acrylamide/sodium 2-acrylamidomethylpropanesulfonate copolymer as an inverse emulsion at 40% in isoparaffin/water (Sepigel 305® from SEPPIC) 0.1 %
Carboxyvinyl polymer (Synthalen K® from 3V) 0.3%
Plant oils 5.0%
Water qs 100%
0.75% of 2-phenoxyethylamine (compound II) or of 2-phenoxyethylamine citrate (compound IV) or of 2-phenoxyethylamine lactate (compound V), respectively, is added to this makeup-removing milk.
*= the support alone shows intrinsic activity towards these microorganisms, which prevents the demonstration of antimicrobial activity of a starting material.
Emulsion (Control) Sorbitan tristearate (Span 65 V® from Croda) 0.9%
Polyethylene glycol (40 EO) stearate (Myrj 52 P® from the company Croda) 2.0%
Mixture of glyceryl mono-distearate (36/64)/potassium stearate 3.0%
Fatty acids of plant origin (53/44/3 stearic acid/palmitic acid/myristic acid) 1.0%
Cetyl alcohol 3.8% Myristyl myristate 2.0%
Cyclopentasiloxane 5.0%
Fillers 0.8%
Glycerol 3.0%
Hydrogenated isoparaffin 7.2% White petroleum jelly 4.0%
Water qs 100%
0.75% of 2-phenoxyethylamine (compound II) or of 2-phenoxyethylamine citrate (compound IV), respectively, is added to this emulsion.
Water/oil emulsion (Control) Magnesium sulfate 0.175% Cyclopentadimethylsiloxane 12.000% Glycerol 3.250%
Acrylamide/acrylamido^-methylpropanesulfonic copolymer, sodium salt 1.000%
Acetyl glycol distearate/glyceryl tristearate mixture 0.125%
Poly dimethyl/methylcetyl/methylsiloxane EO 0.750%
Water qs 100%
0.75% of 2-phenoxyethylamine (compound II) is added to this water/oil emulsion.
Foundation (Control)
Magnesium sulfate 0.7% Vinylidene chloride/acrylonitrile/polymethyl methacrylate microspheres expanded with isobutane (Expancel 551 from Expancel) 0.2%
Cyclopentadimethylsiloxane 10.3%
Cyclohexadimethylsiloxane (8 cSt) 6.0%
Phenyltrimethylsiloxysiloxane (20 cSt) 8.0% Mixture of dimethicone copolyol, cyclopentasiloxane and water (10/88/2)
(DC 5225C from Dow Corning) 2.0%
Cetyl dimethicone copolyol (Abil EM 90 from Goldschmidt) 3.0%
Titanium oxides 8.9%
Iron oxides 2.1 %
Nacres 4.0%
Polyglyceryl-4 isostearate (Isolan Gl 34 from Goldschmidt) 1.0%
Carboxymethylcellulose (Blanose 7M8SF from Aqualon) 0.4%
1 ,3-Butylene glycol 5.0%
Water qs 100%
0.75% of phenoxyethylamine citrate (compound IV) is added to this foundation.
**: result <200 after 14 days.
This second study demonstrates that the compounds of formula (I), in particular compounds IV and V (citrate and lactate salified forms) according to the invention, have a very broad antimicrobial spectrum due to their antibacterial and antifungal activity.
The compounds of formula (I), in particular compounds IV and V according to the invention, are efficient preserving agents, in particular in the formulations tested.
EXAMPLE 5: Formulation examples
The percentages are expressed as weight percentages relative to the total weight of the compositions.
Lotion
- 2-phenoxyethylamine citrate 0.75%
- glycerol 2%
- ethyl alcohol 20%
- mixture of oxyethylenated (26 EO) oxypropylenated (26 PO) butanol and oxyethylenated (40 EO) hydrogenated castor oil in water 1 %
- demineralized water qs 100%
Facial qel
- polyglyceryl acrylate (Norgel) 30%
- polyacrylamide/C13-14 isoparaffine/laureth-7 (Sepigel 305) 2%
- silicone oil 10%
- 2-phenoxyethylamine lactate 5%
- water qs 100%
Treatinq qel
- 2-phenoxyethylamine 1 %
- xanthan gum 1 %
- glycerol 2%
- ethanol 20%
- mixture of oxyethylenated (26 EO) oxypropylenated (26 PO) butanol and oxyethylenated (40 EO) hydrogenated castor oil in water 1 %
- fragrance qs
- demineralized water qs 100%
Foaminq cleansinq cream
- ethylene glycol monostearate 2%
- 3-phenoxypropylamine 0.5%
- hydrated magnesium aluminium silicate 1.7%
- hydroxypropylmethylcellulose 0.8%
- mixture of sodium cocoyl isethionate and of coconut fatty acids
(Elfan AT 84 G from Akzo) 15%
- stearic acid 1.25%
- sodium lauroyl sarcosinate at 30% in water 10%
- fragrance qs
- demineralized water qs 100%
Care cream
- sorbitan tristearate 1 %
- 3-phenoxypropylamine citrate 1.5%
- crosslinked carboxyvinyl homopolymer 0.4% - xanthan gum 0.5%
- ethylene glycol dimethacrylate/lauryl methacrylate copolymer 1 %
- cyclopentadimethylsiloxane 6%
- glycerol 3%
- emulsifier 4% - fragrance qs
- demineralized water qs 100%
Cover stick
- waxes (carnauba wax and ozokerite) 14%
- liquid fraction of shea butter 4%
- titanium oxide and zinc oxide 22%
- iron oxides 4%
- 3-phenoxypropylamine lactate 1 %
- polydimethylsiloxane/hydrated silica 0.1 %
- cetyl alcohol 1.4%
- isoparaffin qs 100%
Tinted cream
- hydrogenated lecithin 2.4%
- apricot kernel oil 6%
- ethylene glycol dimethacrylate/lauryl methacrylate copolymer 1 %
- oxyethylenated (5 EO) soybean sterols 1.6%
- 2-phenoxyethylamine citrate 1 %
- iron oxides 0.9%
- titanium oxide 5%
- polyacrylamide/Cis-Cu-isoparaffin/Laureth-y (Sepigel 305) 4%
- cyclopentadimethylsiloxane 6%
- glycerol 6%
- propylene glycol 6%
- fragrance qs
- demineralized water qs 100%
Claims
1. Use of at least one compound of the phenoxyalkylamine family corresponding to formula (I)
2. Use of at least one compound of formula (I) as defined in the preceding claim, as an antimicrobial and/or antibacterial and/or antifungal agent.
3. Use according to either of Claims 1 and 2, characterized in that the compound of formula (I) is chosen from:
2-phenoxyethylamine (compound II)
3-phenoxypropylamine (compound
4. Use of at least one compound of formula (I) as defined in anyone of the preceding claims, in a salified form obtained by adding a mineral acid chosen especially from hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, or an organic acid chosen especially from carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid, glycolic acid, citric acid, gluconic acid, salicylic acid and tartaric acid.
5. Use according to the preceding claim, characterized in that the compound is a 2-phenoxyethylamine citrate
6. Use according to Claim 4, characterized in that the compound is a 2-phenoxyethylamine lactate
7. Use according to anyone of the preceding claims, in which the compound of formula (I) is present in the cosmetic, dermatological or pharmaceutical composition in an amount of between 0.001 % and 30% by weight, preferably between 0.01% and 15% by weight and more particularly between 0.1 % and 5% by weight relative to the total weight of the composition.
8. Use according to anyone of the preceding claims, in which the composition is present: - in the form of a makeup product for facial skin, bodily skin or the lips, such as a foundation, a makeup rouge, an eyeshadow, a concealer stick, a cover stick, an eyeliner, a mascara, a lipstick, a nail varnish or a nailcare product;
- in the form of a dermatological or cosmetic care product for facial skin, bodily skin including the scalp, or the lips, such as a lipcare base, a fixing base to be applied over a standard lipstick, an antisun or artificial tanning composition; a deodorant product; a facial care composition; a facial matting composition; a cleansing or makeup-removing gel or cream; a protective or care body milk; a purifying milk;
- in the form of a deodorizing composition; an aftershave gel or lotion; a hair- removing cream; - in the form of a body hygiene composition, such as a shower gel, a shampoo or a deodorant; - in the form of a pharmaceutical composition;
- in the form of a solid composition such as a soap or a cleansing bar;
- in the form of an aerosol composition also comprising a propellant under pressure; - in the form of a haircare composition, and especially a shampoo, a hairsetting lotion, a treating lotion, a hairstyling cream or gel, a dye composition optionally in the form of a colouring shampoo, a hair restructuring lotion, a permanent-waving composition, a lotion or gel for combating hair loss, an antiparasitic shampoo; an antidandruff lotion or shampoo; a medicated shampoo, especially an anti-seborrhoea shampoo. - in the form of a composition for dentibuccal use, a toothpaste.
9. Process for preserving a cosmetic and/or dermatological composition, characterized in that it consists in incorporating into the said composition at least one compound of formula (I) as defined in any one of Claims 1 and 3 to 6.
10. Compounds of formula (I) as defined in Claim 1 , in a salified form, wherein the salified form is obtained by adding a compound of formula (I) as defined in Claim 1 to an acid selected from sulphuric acid, nitric acid, carbonic acid, acetic acid, succinic acid, fumaric acid, lactic acid, glycolic acid, citric acid, gluconic acid, salicylic acid or tartaric acid.
1 1. Compounds of formula (I) as defined in Claim 1 , in citrate or lactate salified form.
12. Compound according to Claim 1 1 , characterized in that it is 2- phenoxyethylamine citrate.
13. Compound according to Claim 11 , characterized in that it is 2- phenoxyethylamine lactate.
14. Process for preparing a compound as defined in Claim 1 1 , comprising: a) a step of chemical synthesis of the said compound especially according to one of the reactions chosen from: i) alkylation of phenol with a haloalkylamide (C2-C8 alkyl chain), followed by a reduction; ii) alkylation of phenol with a C2-C8 dihaloalkane, followed by an amination; Ni) amination via reaction of a phenoxyhaloalkane (C2-Cs alkane chain) with potassium phthalimide; iv) reaction between phenol and an amino alcohol (C2-C8 alcohol); or v) opening of the oxazolidine ring with phenol, followed by a hydrolysis; or, according to an alternative, the use of 2-phenoxyethylamine or 3-phenoxy- propylamine; b) a step of salification in the presence of citric acid or a lactic acid.
15. Cosmetic and/or dermatological composition comprising a compound of formula (I) as defined in anyone of Claims 1 , 3, 4, and 10 to 13, the said composition possibly being especially in the form of:
- a makeup product for facial skin, bodily skin or the lips;
- an antisun or artificial tanning composition; - an aftershave gel or lotion;
- a hair-removing cream;
- a body hygiene composition, such as a shower gel, a shampoo or a deodorant;
- a pharmaceutical composition;
- a solid composition such as a soap or a cleansing bar; - an aerosol composition also comprising a propellant under pressure;
- a hairsetting lotion, a hairstyling cream or gel, a dye composition, a hair restructuring lotion, a permanent-waving composition or a lotion or gel for combating hair loss;
- a composition for dentibuccal use.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0854727 | 2008-07-10 | ||
| FR0854727A FR2933694B1 (en) | 2008-07-10 | 2008-07-10 | USE OF PHENOXYALKYLAMINES IN COSMETIC AND / OR DERMATOLOGICAL COMPOSITIONS. |
| US8957808P | 2008-08-18 | 2008-08-18 | |
| US61/089,578 | 2008-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2010004016A1 true WO2010004016A1 (en) | 2010-01-14 |
Family
ID=40260804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2009/058781 WO2010004016A1 (en) | 2008-07-10 | 2009-07-09 | Use of phenoxyalkylamines in cosmetic and/or dermatological compositions |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2933694B1 (en) |
| WO (1) | WO2010004016A1 (en) |
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| US5672588A (en) * | 1992-05-20 | 1997-09-30 | Novo Nordisk A/S | Purine derivatives |
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|---|---|---|---|---|
| GB670991A (en) * | 1948-05-21 | 1952-04-30 | Ciba Ltd | Manfuacture of amines |
| US3198701A (en) * | 1961-07-31 | 1965-08-03 | Boehringer Sohn Ingelheim | Method of curbing appetite with 1-phenoxy-2-amino-propane |
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| FR2933694B1 (en) | 2016-10-21 |
| FR2933694A1 (en) | 2010-01-15 |
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