WO2007051586A1 - Bacteriostatic and/or bactericide agent for cosmetic and/or dermopharmaceutical preparations and preparations containing this agent - Google Patents

Bacteriostatic and/or bactericide agent for cosmetic and/or dermopharmaceutical preparations and preparations containing this agent Download PDF

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Publication number
WO2007051586A1
WO2007051586A1 PCT/EP2006/010433 EP2006010433W WO2007051586A1 WO 2007051586 A1 WO2007051586 A1 WO 2007051586A1 EP 2006010433 W EP2006010433 W EP 2006010433W WO 2007051586 A1 WO2007051586 A1 WO 2007051586A1
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Prior art keywords
pca
phenoxyethanol
agent according
benzyl
agent
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Application number
PCT/EP2006/010433
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French (fr)
Inventor
Giovanni Razzano
Original Assignee
Roda S.R.L.
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Publication of WO2007051586A1 publication Critical patent/WO2007051586A1/en

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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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • 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

Definitions

  • the present invention concerns a bacteriostatic and/or bactericide agent, suitable for making cosmetic and/or dermopharmaceutical preparations.
  • the invention also extends to said preparations obtained with this agent.
  • PCA 2-pyrrolidon-5-carboxylic acid
  • the general purpose of the present invention is to provide a bacteriostatic and/or bactericide agent that, compared to conventional agents of the same type, can be obtained more easily, with higher yields and without components that are harmful to the skin.
  • a further purpose of the invention is to provide a new 2- phenoxyethanol -based bacteriostatic and/or bactericide agent that, unlike known agents of this type, has a wider activity spectrum, even using lower dosages of this substance.
  • the invention has the purpose of providing the cosmetic and/or dermopharmaceutical preparations obtained with this bacteriostatic and/or bactericide agent.
  • the one according to the invention offers the advantage of being obtained more easily, with higher yields and without components that are harmful to the skin.
  • the bacteriostatic and/or bactericide agent of the invention in its 2-phenoxyethanol-based version, for its part has the advantage of offering a wider activity spectrum, even using lower dosages of this substance.
  • the agent with bacteriostatic and/or bactericide action of the invention comprises the benzyl ester of 2-pyrrolidon-5-carboxylic acid (PCA) of formula (I) :
  • the bacteriostatic and/or bactericide agent of the invention comprises a mixture, in 2- phenoxyethanol of formula (III) :
  • the esters of PCA or the mixture thereof in 2-phenoxyethanol can be dissolved in various types of solvents including, just as non-limiting examples, ethylene, propylene and butylene glycols, glycerine, ethoxydiglycol and 2-methyl-1, 3-propanediol . It is also possible to use other solvent substances.
  • the solubility concentration can range from 20% to 80% by weight of the esters of PCA or of the quoted mixture, with an optimal value of 50%.
  • the agent of the invention can comprise at least one solvent and/or excipient for said esters of PCA of formula (I), (II), including:
  • Carboxylic acids in particular sorbic acid-benzoic acid- dehydroacetic acid
  • said mixtures can be in whatever percentage ratio even in a mixture of many solvents and/or excipients.
  • compositions of the agent of the invention are tabulated, followed by example challenge tests.
  • the bacteriostatic and/or bactericide agent of the invention has proven to be a good skin hydrator and biocompatible with the connecting tissue.
  • studies on the conservant activity of mixtures of 2-phenoxyethanol with the benzyl and/or ethyl alcohol ester of 2-pyrrolidon-5- carboxylic acid have demonstrated that it is possible to obtain an effective preservant and conservant activity against bacteria gram ⁇ and gram-, as well as against yeasts and moulds, in cosmetic and dermopharmaceutical formulae, using very low concentrations, with respect to 2- phenoxyethanol as such.
  • These mixtures also have displayed greater dermocompatibility than 2-phenoxyethanol, achieved thanks to the presence of ester derived from a natural product like PCA, constituent of the cutaneous hydrolipidic film.
  • the agent of the invention can therefore be effectively used in all cosmetic and dermopharmaceutical formulae, both as the only conservant, and in combination with other preservants, without incurring problems of stability at different pH levels .
  • Examples of cosmetic and dermopharmaceutical preparations comprising the bacteriostatic and/or bactericide agent of the invention are lotions in aqueous solution, detergents (like bubble bath, shampoo, shower gel, cleansing oils, liquid soaps, syndet, bars of soap), fluid and thick emulsions, aqueous and water-soluble gels, preparations for make-up, lipstick and wet wipes.
  • detergents like bubble bath, shampoo, shower gel, cleansing oils, liquid soaps, syndet, bars of soap
  • fluid and thick emulsions aqueous and water-soluble gels
  • preparations for make-up, lipstick and wet wipes preparations for make-up, lipstick and wet wipes.
  • MIC Minimum Inhibition Concentration
  • the Challenge test which consists of inoculating colonies of bacteria, mould and yeast of known numerical size in cosmetic or dermopharmaceutical preparations.
  • the survival rate is followed with tests after 48 hours, 7 days and 28 days from inoculation.
  • a result of a reduction of the inoculated colonies by an exponential rate of at least three logarithms after 7 days from inoculation is considered satisfactory.
  • the attached tables 3 to 7 show the results of reduction of the inoculated colonies with this type of test, carried out on detergent emulsions that contain the agent of the invention in its respective TWINCIDE A, TWINCIDE EDG, TWINCIDE PG (phenoxyethanol + benzyl PCA + propylene glycol) , TWINCIDE G (phenoxyethanol + benzyl PCA + glycerine) , and TWINCIDE BG (phenoxyethanol + benzyl PCA + butylene glycol) forms, with which it is demonstrated that the mixtures of 2- phenoxyethanol + benzyl ester of PCA, as such or in the different solvents used, have a good bacteriostatic and/or bactericide activity.
  • TWINCIDE A TWINCIDE EDG
  • TWINCIDE PG phenoxyethanol + benzyl PCA + propylene glycol
  • TWINCIDE G phenoxyethanol + benzyl PCA + glycerine

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

A bacteriostatic and/or bactericide agent for cosmetic and/or dermopharmaceutical preparations, comprising the benzyl ester and the ethyl ester, by themselves or mixed together, of 2- pyrrolidon-5-carboxylic acid, possibly also in the presence of 2-phenoxyethanol . Compared to conventional bacteriostatic and/or bactericide agent, the one according to the invention offers the advantage of being obtained more easily, with higher yields and without components that are harmful to the skin. The bacteriostatic and/or bactericide agent of the invention, in its 2-phenoxyethanol -based version, for its part has the advantage of offering a wider activity spectrum, even using lower dosages of this substance.

Description

BACTERIOSTATIC AND/OR BACTERICIDE AGENT FOR COSMETIC AND/OR
DERMOPHARMACEUTICAL PREPARATIONS AND PREPARATIONS CONTAINING THIS AGENT
DESCRIPTION
The present invention concerns a bacteriostatic and/or bactericide agent, suitable for making cosmetic and/or dermopharmaceutical preparations. The invention also extends to said preparations obtained with this agent.
Cosmetic and dermopharmaceutical preparations that contain bacteriostatic and/or bactericide agents consisting of esters of 2-pyrrolidon-5-carboxylic acid (PCA) are currently known. These agents nevertheless have the drawback of being difficult to prepare and of being obtained with reactions having a very low yield. Conventional agents of the type under discussion also have the disadvantage of containing halides, and therefore of being harmful to the skin.
In the preparation of cosmetic and dermopharmaceutical formulae it is also known to use 2 -phenoxyethanol as bacteriostatic stabilising agent. This substance, however, has the disadvantage of requiring high dosages to be able to be effective, with the consequent problems of toxicological compatibility with the skin. 2 -phenoxyethanol also has the drawback of displaying a somewhat limited activity spectrum, with respect to the requirements of the preparations of the invention .
The general purpose of the present invention is to provide a bacteriostatic and/or bactericide agent that, compared to conventional agents of the same type, can be obtained more easily, with higher yields and without components that are harmful to the skin.
A further purpose of the invention is to provide a new 2- phenoxyethanol -based bacteriostatic and/or bactericide agent that, unlike known agents of this type, has a wider activity spectrum, even using lower dosages of this substance.
Finally, the invention has the purpose of providing the cosmetic and/or dermopharmaceutical preparations obtained with this bacteriostatic and/or bactericide agent.
These and other purposes are accomplished with the bacteriostatic and/or bactericide agent and with the cosmetic and/or dermopharmaceutical preparations of claims 1 and 9 respectively. Preferred embodiments of the invention can be found in the remaining claims.
Compared to conventional bacteriostatic and/or bactericide agents, the one according to the invention offers the advantage of being obtained more easily, with higher yields and without components that are harmful to the skin.
The bacteriostatic and/or bactericide agent of the invention, in its 2-phenoxyethanol-based version, for its part has the advantage of offering a wider activity spectrum, even using lower dosages of this substance.
According to a first embodiment thereof, the agent with bacteriostatic and/or bactericide action of the invention comprises the benzyl ester of 2-pyrrolidon-5-carboxylic acid (PCA) of formula (I) :
Figure imgf000004_0001
or else the ethyl ester of PCA having formula (II)
Figure imgf000004_0002
(ID
or mixtures thereof.
According to a variant thereof, the bacteriostatic and/or bactericide agent of the invention comprises a mixture, in 2- phenoxyethanol of formula (III) :
Figure imgf000005_0001
( II I )
of at least one of said benzyl and ethyl esters of PCA of formula (I) and (II) respectively. Said mixture can be obtained at different concentrations of ester of PCA and 2- phenoxyethanol, which can vary between a 10:90 ratio and a 90:10 ratio of the two components by weight. From the analyses carried out it has been seen that the best ratio between the two substances in the mixture, in order to have a good bacteriostatic activity and optimal skin compatibility, is one part of 2-phenoxyethanol to one part of benzyl and/or ethyl ester of PCA.
In the agent of the invention, the esters of PCA or the mixture thereof in 2-phenoxyethanol can be dissolved in various types of solvents including, just as non-limiting examples, ethylene, propylene and butylene glycols, glycerine, ethoxydiglycol and 2-methyl-1, 3-propanediol . It is also possible to use other solvent substances. The solubility concentration can range from 20% to 80% by weight of the esters of PCA or of the quoted mixture, with an optimal value of 50%.
In particular, the agent of the invention can comprise at least one solvent and/or excipient for said esters of PCA of formula (I), (II), including:
- Alcohols (mono-di- tri) : in particular propylene Glycerol - Glycol -Ethanol- Capryl Glycol -Pentylene Glycol
- Carboxylic acids: in particular sorbic acid-benzoic acid- dehydroacetic acid
- Common solvent substances like methyl pyrrolidone-acetone .
All of the above is to widen the spectrum of bactericide agent action and to make it easier to incorporate them in cosmetic and dermopharmaceutical preparations of said esters of PCA respectively of formula (I) and (II) .
For this purpose, said mixtures can be in whatever percentage ratio even in a mixture of many solvents and/or excipients.
Hereafter, some example compositions of the agent of the invention are tabulated, followed by example challenge tests.
MIC minimum inhibition concentration Benzyl PCA/Glycerol
percentage ratio 50/50
Figure imgf000006_0001
MIC minimum inhibition concentration Benzyl PCA/Methyl pyrrolidone percentage ratio 50/50
Figure imgf000007_0001
MIC minimum inhibition concentration Benzyl PCA/Methyl pyrrolidone
percentage ratio 60/40
Figure imgf000007_0002
CHALLENGE TEST shower gel BENZYL PCA/METHYL PYRROLIDONE
ratio 50/50
use percentage 1%
Figure imgf000007_0003
Figure imgf000008_0001
CHALLENGE TEST shower gel BENZYL PCA/METHYL PYRROLIDONE
ratio 50/50
use percentage 2%
Figure imgf000008_0002
CHALLENGE TEST shower gel BENZYL PCA/GLYCEROL
ratio 50/50
use percentage 2%
Figure imgf000009_0001
The bacteriostatic and/or bactericide agent of the invention has proven to be a good skin hydrator and biocompatible with the connecting tissue. In particular, studies on the conservant activity of mixtures of 2-phenoxyethanol with the benzyl and/or ethyl alcohol ester of 2-pyrrolidon-5- carboxylic acid have demonstrated that it is possible to obtain an effective preservant and conservant activity against bacteria gram÷ and gram-, as well as against yeasts and moulds, in cosmetic and dermopharmaceutical formulae, using very low concentrations, with respect to 2- phenoxyethanol as such. These mixtures also have displayed greater dermocompatibility than 2-phenoxyethanol, achieved thanks to the presence of ester derived from a natural product like PCA, constituent of the cutaneous hydrolipidic film.
The agent of the invention can therefore be effectively used in all cosmetic and dermopharmaceutical formulae, both as the only conservant, and in combination with other preservants, without incurring problems of stability at different pH levels .
Examples of cosmetic and dermopharmaceutical preparations comprising the bacteriostatic and/or bactericide agent of the invention are lotions in aqueous solution, detergents (like bubble bath, shampoo, shower gel, cleansing oils, liquid soaps, syndet, bars of soap), fluid and thick emulsions, aqueous and water-soluble gels, preparations for make-up, lipstick and wet wipes.
Test of the bacteriostatic activity
of the agent of the invention
The most renowned test for testing bacteriostatic and/or bactericide activity is the so-called MIC (Minimum Inhibition Concentration) . This test indicates the lowest use concentration of a substance having bacteriostatic activity, in order to prevent the development of bacterial, fungal or yeast colonies. The lower this concentration, the greater the bacteriostatic and/or bactericide activity of the substance being studied.
From the attached tables 1 and 2, which concern this type of test, it can be seen that the inhibition concentrations (MIC) detected on the agent of the invention, respectively in the TWINCIDE A (phenoxyethanol + benzyl PCA) and TWINCIDE EDG (phenoxyethanol + benzyl PCA + ethoxydiglycol solution) versions, are totally satisfactory for the purposes of a positive judgement of bacteriostatic and/or bactericide activity of mixtures of 2 -phenoxyethanol + benzyl ester of PCA. On the other hand, the average values obtained with the MIC test using pure 2 -phenoxyethanol are clearly higher.
Test of bacteriostatic and/or bactericide efficiency in the
cosmetic and dermopharmaceutical preparations of the invention
These tests are carried out using the Challenge test, which consists of inoculating colonies of bacteria, mould and yeast of known numerical size in cosmetic or dermopharmaceutical preparations. The survival rate is followed with tests after 48 hours, 7 days and 28 days from inoculation. A result of a reduction of the inoculated colonies by an exponential rate of at least three logarithms after 7 days from inoculation is considered satisfactory.
The attached tables 3 to 7 show the results of reduction of the inoculated colonies with this type of test, carried out on detergent emulsions that contain the agent of the invention in its respective TWINCIDE A, TWINCIDE EDG, TWINCIDE PG (phenoxyethanol + benzyl PCA + propylene glycol) , TWINCIDE G (phenoxyethanol + benzyl PCA + glycerine) , and TWINCIDE BG (phenoxyethanol + benzyl PCA + butylene glycol) forms, with which it is demonstrated that the mixtures of 2- phenoxyethanol + benzyl ester of PCA, as such or in the different solvents used, have a good bacteriostatic and/or bactericide activity.

Claims

1. Bacteriostatic and/or bactericide agent for cosmetic and/or dermopharmaceutical preparations, characterised in that it comprises the benzyl ester of 2-pyrrolidon-5- carboxylic acid (PCA) of formula (I) :
Figure imgf000013_0001
(D
or else the ethyl ester of PCA having formula (II)
Figure imgf000013_0002
(ID
or mixtures thereof .
2. Agent according to claim 1, characterised in that it comprises a mixture, in 2-phenoxyethanol of formula (III) :
Figure imgf000014_0001
( I II )
of at least one of said benzyl and/or ethyl esters of PCA of formula (I) and (II) respectively.
3. Agent according to claim 2, characterised in that the concentrations of said esters of PCA and 2-phenoxyethanol in mixture are between 10:90 and 90:10 by weight.
4. Agent according to claim 3, characterised in that said mixture consists of one part of 2-phenoxyethanol and one part of benzyl and/or ethyl ester of PCA.
5. Agent according to any one of the previous claims, characterised in that it also comprises at least one solvent and/or excipient for said esters of PCA of formula (I) and
(II), or of the mixtures of these with 2-phenoxyethanol.
6. Agent according to claim 5, characterised in that said solvent consists of ethoxydiglycol, propylene glycol, glycerine or 2-methyl-1, 3 -propanediol .
7. Agent according to claim 6, characterised in that it consists of phenoxyethanol + benzyl PCA + ethoxydiglycol, phenoxyethanol + benzyl PCA + propylene glycol, phenoxyethanol + benzyl PCA + glycerine or phenoxyethanol + benzyl PCA + butylenes glycol + 2 -methyl -1, 3 -propanediol solutions .
8. Agent according to claim 6, characterised in that the solubility concentration is from 20% to 80% by weight of said esters or of the quoted mixture, preferably 50%.
9. Agent according to claim 5, characterised in that said solvent and/or excipient comprises poly-tri alcohols selected from glycerol, propylene glycol, ethanol, capryl glycol, pentylene Glycol .
10. Agent according to claim 5, characterised in that said solvent and/or excipient comprises carboxylic acids selected from sorbic acid, benzoic acid and dehydroacetic acid.
11. Agent according to claim 5, characterised in that said solvent and/or excipient comprises methyl pyrrolidone and/or acetone .
12. Cosmetic and/or dermopharmaceutical preparation, characterised in that it comprises a bacteriostatic and/or bactericide agent according to one or more of the previous claims .
PCT/EP2006/010433 2005-10-31 2006-10-31 Bacteriostatic and/or bactericide agent for cosmetic and/or dermopharmaceutical preparations and preparations containing this agent WO2007051586A1 (en)

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IT002077A ITMI20052077A1 (en) 2005-10-31 2005-10-31 BACTERIOSTATIC AND BACTERICIDAL AGENT FOR COSMETIC E-O DERMO-PHARMACEUTICAL PREPARATIONS AND PREPARATIONS CONTAINING THIS AGENT

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007005336A1 (en) * 2007-02-01 2008-08-07 Beiersdorf Ag UV filter combination with piperazine derivatives
DE102007005335A1 (en) * 2007-02-01 2008-08-07 Beiersdorf Ag Sunscreen preparation with a combination of micropigments
DE102007005334A1 (en) * 2007-02-01 2008-08-07 Beiersdorf Ag Piperazine derivatives in diol-containing cosmetic preparations
US8933134B2 (en) 2010-06-09 2015-01-13 L'oreal Compositions containing agar and a softening agent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2456634A1 (en) * 1974-11-29 1976-08-12 Thomae Gmbh Dr K Pyroglutamic acid aralkyl esters - prepd e.g. by esterifying pyroglutamic acid with an aralkanol
EP0135444A1 (en) * 1983-09-12 1985-03-27 Laboratoires Serobiologiques S.A. Pyroglumatic derivatives, process for their preparation , intermediates and bactericidal and/or fungicidal cosmetic or pharmaceutical compositions
EP0342055A2 (en) * 1988-05-13 1989-11-15 Unilever Plc Use of pyroglutamic acid alkyl esters for the manufacture of a medicament for the treatment of ichthyosis
WO2001028552A2 (en) * 1999-10-19 2001-04-26 The Procter & Gamble Company Antimicrobial compositions comprising pyroglutamic acid and optionally metal salts
WO2005079852A2 (en) * 2004-02-13 2005-09-01 Vama Farmcosmetica S.R.L. Bacteriostatic esters for topical use

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2456634A1 (en) * 1974-11-29 1976-08-12 Thomae Gmbh Dr K Pyroglutamic acid aralkyl esters - prepd e.g. by esterifying pyroglutamic acid with an aralkanol
EP0135444A1 (en) * 1983-09-12 1985-03-27 Laboratoires Serobiologiques S.A. Pyroglumatic derivatives, process for their preparation , intermediates and bactericidal and/or fungicidal cosmetic or pharmaceutical compositions
EP0342055A2 (en) * 1988-05-13 1989-11-15 Unilever Plc Use of pyroglutamic acid alkyl esters for the manufacture of a medicament for the treatment of ichthyosis
WO2001028552A2 (en) * 1999-10-19 2001-04-26 The Procter & Gamble Company Antimicrobial compositions comprising pyroglutamic acid and optionally metal salts
WO2005079852A2 (en) * 2004-02-13 2005-09-01 Vama Farmcosmetica S.R.L. Bacteriostatic esters for topical use

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007005336A1 (en) * 2007-02-01 2008-08-07 Beiersdorf Ag UV filter combination with piperazine derivatives
DE102007005335A1 (en) * 2007-02-01 2008-08-07 Beiersdorf Ag Sunscreen preparation with a combination of micropigments
DE102007005334A1 (en) * 2007-02-01 2008-08-07 Beiersdorf Ag Piperazine derivatives in diol-containing cosmetic preparations
US8933134B2 (en) 2010-06-09 2015-01-13 L'oreal Compositions containing agar and a softening agent

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