WO2012131363A2 - Deodorant formulations - Google Patents
Deodorant formulations Download PDFInfo
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- WO2012131363A2 WO2012131363A2 PCT/GB2012/050690 GB2012050690W WO2012131363A2 WO 2012131363 A2 WO2012131363 A2 WO 2012131363A2 GB 2012050690 W GB2012050690 W GB 2012050690W WO 2012131363 A2 WO2012131363 A2 WO 2012131363A2
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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
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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
Definitions
- the present invention relates to the reduction or prevention of body odour and specifically to deodorant compositions comprising a morpholino compound and to their use in improving the odour of the surface of the axilla.
- the axilla (or armpit, underarm, or oxter) is the area of the human body directly under the joint where the arm connects to the shoulder.
- the contents of the axilla include the axillary vein and artery, as well as the brachial plexus, lymph nodes and fat.
- Axilla is the space between the side of the thorax and the upper arm.
- the term "underarm” typically refers to the outer surface of the axilla. However, the terms are sometimes used interchangeably in casual contexts.
- armpit refers to an object or place which is smelly, greasy or otherwise undesirable. Underarm hair usually grows in the underarms of both females and males, beginning in adolescence.
- Body odour sometimes colloquially abbreviated as B.O., is the smell of bacteria growing on the body. The bacteria multiply rapidly in the presence of sweat, but sweat itself is almost completely odourless to humans.
- the condition can be known medically as bromhidrosis, apocrine bromhidrosis, bromidrosis, osmidrosis, ozochrotia, fetid sweat, body smell or malodourous sweating.
- Body odour can smell specific to the individual and can be used to identify people.
- An individual's body odour is influenced by diet, lifestyle, gender, genetics, health and medication.
- apocrine and eccrine Human secretory glands are primarily divided into 2 types: apocrine and eccrine. Eccrine glands are distributed over the entire skin surface, where they are involved in thermoregulation by means of sweat production. In contrast, apocrine glands have a limited distribution involving the axilla, genital skin, and breasts. Apocrine elements are also found in the periorbital and periauricular areas. Apocrine glands have no thermoregulatory role but are responsible for characteristic pheromonal odours. They secrete a small amount of oily fluid, which is odourless upon reaching the skin surface. The characteristic odour is due to bacterial decomposition of the oily fluid. Studies have shown that in comparison to controls, individuals with bromhidrosis display more numerous and larger apocrine glands.
- Propionic acid is present in many sweat samples. This acid is a breakdown product of some amino acids by propionibacteria, which thrive in the ducts of adolescent and adult sebaceous glands. Because propionic acid is chemically similar to acetic acid with similar characteristics including odour, body odours may be identified as having a vinegar-like smell by certain people. Isovaleric acid (3-methyl butanoic acid) is the other source of body odour as a result of actions of the bacteria Staphylococcus epidermidis, which is also present in several strong cheese types.
- Body odour is also caused by the actions of skin flora, including members of Corynebacterium, which manufacture enzymes called lipases that break down the lipids in sweat to create smaller molecules. These smaller molecules smell, and give body odour its characteristic aroma. Body odour may be reduced or prevented or even aggravated by using deodorants, antiperspirants, disinfectants (e.g., triclosan), special soaps or foams with antiseptic plant extracts such as ribwort and liquorice, chlorophyllin ointments and sprays topically, and chlorophyllin supplements internally. Although body odour is commonly associated with hygiene practices, its presentation can be affected by changes in diet as well as the other factors discussed above.
- antiperspirant and deodorants are colloquially interchangeable. However, they are differentiated in that antiperspirants seek to reduce armpit malodour through reduction of perspiration, whilst deodorants disguise the existence of malodour. Both are often present in single cosmetic products.
- Antiperspirants include aluminium salts, which cause mechanical obstruction of eccrine sweat ducts. Aluminium has been associated with undesirable effects such as Alzheimer's Disease, DNA alterations and epigenetic effects. Titanium salts are also used as antiperspirants.
- Water-insoluble films of polymers create occlusion on the axillary skin, thereby reducing the underarm wetness. Such films are a barrier to the passage of sweat.
- film-forming antiperspirant polymers have been described as being capable of a greater perspiration reduction compared with traditional antiperspirant salts.
- Polymers used should be occlusive, insoluble in water, high in degree of adhesion, and nontoxic.
- Several polymers have been applied for the occlusive effects, including polyvinyl alcohol derivatives, chloroacetate derivatives of hydroxy polymers, spherical calcium alginate, and octylacrylamide/acrylate copolymer.
- fragrance compositions have been used to mask the unpleasant body odour since ancient times.
- fragrance compositions can be classified into three categories, namely natural, semi-synthetic, and synthetic.
- Natural fragrances are obtained from living organisms, that is, plants and animals. Plants are major sources of essential oils and aromatic substances. Plant fragrances include the extracts of stems, leaves, fruits, roots, and woods. Civet and beaver are examples of animal fragrance materials. Today, the use of animal sources is not practical due to ethical and legal issues. Natural fragrance compositions can be used as precursors for semi-synthetic fragrances. By chemical alteration, intermediate natural compounds can be converted into semisynthetic substances. Synthetic fragrances are prepared by synthesis methods.
- fragrances are products of esters, aldehydes, alcohols, and ethers. !n addition to masking malodour, some fragrances have been shown to possess antimicrobial properties. In general, fragrance compositions at 0.2-1.5% levels are employed in deodorant products.
- fragrance compositions at 0.2-1.5% levels are employed in deodorant products.
- United States Patent 538070715 discloses that the long-lasting fragrance compositions could be achieved with the fixative agent, acetyl hexamethyl tetraiin.
- Sodium bicarbonate and zinc carbonate are examples of odour-neutralizing agents. These agents work by neutralizing certain odourous fatty acids that contribute to axillary odour.
- Sodium carbonate is colorless crystals or white, crystalline powder that is soluble in water. With respect to formulation development, sodium carbonate is not easily formulated because its stability is influenced by aqueous solution and high temperature (above 50°C). Unlike sodium carbonate, zinc carbonate is practically insoluble in water. Besides reducing the underarm odour, zinc carbonate possesses mild astringent property.
- Aliphatic diols and their esters work by destroying the bacteria that cause unpleasant body odour, it has been reported that antiperspirants and deodorants containing these compounds are effective and nontoxic to human.
- Examples of aliphatic diols include aliphatic 1 ,3-diols such as 1 ,3- pentanediol, 1 ,3- hexanedioi, and 1 ,3-heptanediol.
- esters of aliphatic diols such as 1 ,3- butanedioi-1 -monopalmitate, 1 ,3-hexanedioi-1 - monoacetate, and 1 ,3-heptanedioi-1 -monoocian pile,
- Esterase inhibitors are compounds that are capable of inhibiting the exoenzymes from the axillary-resident bacteria. Such exoenzymes are able to transform the odourless water-soluble precursors of androstenoi into the volatile steroids, which is responsible for axillary odour.
- Triethyl citrate, trimethyl citrate, and zinc salts such as zinc glycinate are examples of esterase inhibitors.
- Zinc giycinate is an odourless, white crystalline substance that is slightly soluble in water and insoluble in alcohol. The dual function of zinc glycinate as bacterial growth inhibitor and chemical monraiizer of body odours when used in the concentrations of 1-20% is disclosed in United States Patent 4585693.
- Antimicrobial agents are able to prevent or reduce axillary odour by inhibiting or suppressing the growth of microbial populations responsible for malodour generation.
- antimicrobial agents for example triclosan
- Triclosan is the most widely used synthetic antibacterial.
- European Economic Community Council directive 76/768/CEE Appendix VI 81976
- the highest content of triclosan approved to be used in deodorants is 0.30% w/w.
- United States Patent 558715221 discloses deodorant composition containing 0.25% w/w triclosan and using diben-zylidine sorbitol as a gelling agent.
- Other synthetic antibacterial agents include propyi-p-hydroxybenzoate, chlorhexidine gluconate, sodium lactoyl caprylate, trichlorocarboniiide, zinc undecylenate, and glycerolether.
- natural antimicrobial actives include mono- and oiigo-glycryl fatty acid esters that are derived from plants and animals
- Chitosan is a major derivative of chitin, a naturally occurring polysaccharide that is a main constituent of the shells of lobsters and crabs, in addition, exoskeletons of insects and cell walls of fungi are composed of chitin constituent.
- Chitin is a linear polymer composed of ⁇ (1 ⁇ 4) linked 2- acetamido- 2-deoxy ⁇ P-D-glucose units (or N-acetyi-D-giucosamine). Sufficient deacetylation of chitin yields chitosan, a cationic biopoiymer of N-acetyl-D- glucosamine and D-giucosamine.
- Chitosan is soluble in acidic solutions but insoluble in water. Chitosan has deodorizing effect due to its bacteriostatic property.
- the long-lasting deodorizing activity can be achieved by using nanosca!e chitosan and/or chitosan derivatives, having particle diameter in the range 10-300 nm.
- the contents of nanochitosan and derivatives are in the ranges of 0.01-5% by weight.
- Antiperspirants and deodorants in conventional formulations such as original emulsions (milky liquids or creams), sprays and sticks (dispersions of actives in wax-like bases) provide good contact for the product with the skin. However, they leave a residue on the skin after application, resulting in feeling sticky and undesirable looking. Therefore, new formulations such as microemulsions and liquid crystals are developed to overcome the disadvantages of the conventional ones and to provide alternative choices to satisfy the consumers.
- the present invention is based on the surprising discovery that morphoiino compounds of formula (I), and their derivatives, are useful in the reduction of body odour at the surface of the human axilla.
- R. is a straight or branched alkyi group containing 8 to 16 carbon atoms at the 2- or 3-position of the morphoiino ring
- i3 ⁇ 4 is a straight or branched aikyl group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position.
- Deimopinoi a compound of Formula (I) has been shown to reduce colonization of the tooth surface by inhibiting defined stages of orai plaque biofi!m formation (Klinge B, Matsson L, Attstrom R et al, Clin Periodontol 1996; 23: 542-547, Rundegren J, Arnebrant T, Caries Res 1992;26:281 -285 and Rundegren J, Simonsson T, Petersson L, Hansson E. J Dent Res 1992;71 :1792-1796). Deimopinoi has been shown to have poor antimicrobial properties.
- composition comprising a morpholino compound having the general formula (!)
- Ri is a straight or branched aikyi group containing 8 to 16 carbon atoms at the 2- or 3-position of the morpholino ring
- R? is a straight or branched aikyi group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof, for use in the reduction or prevention of body odour.
- a method of reducing or preventing body odour comprising topical application to the skin of a composition comprising a morpholino compound having the general formula wherein R.
- f3 ⁇ 4? is a straight or branched a!kyl group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof.
- a deodorant composition suitable for dermatoiogical application comprising a morpho!ino compound having the general formula
- R-i is a straight or branched alkyl group containing 8 to 16 carbon atoms at the 2 ⁇ or 3-position of the morpho!ino ring
- R2 is a straight or branched alkyl group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof.
- deodorant composition of the present invention is understood to mean a composition which deodorizes the surface of the skin.
- the "deodorant composition” of the invention may be an antiperspirant or a deodorant as per the definitions applied to these terms in the prior art.
- the deodorant composition of the invention may therefore comprise a compound of formula (!) optionally in combination with one or more of a fragrance, an antiperspirant and an antibacterial agent for topical administration.
- an aerosol canister, pump spray container or roil-on container for dermatological application comprising a composition according to the invention.
- malodour refers to the smell caused by bacteria growing on the body.
- the condition can be known medically as bromhidrosis, apocrine bromhidrosis, bromidrosis, osmidrosis, ozochrotia, fetid sweat, body smell or malodourous sweating.
- the morpholino compounds are defined according to the general formula shown above.
- the sum of carbon atoms in the groups R3 ⁇ 4 and f3 ⁇ 4 is at least 10, and is preferably between 10 and 20,
- the f3 ⁇ 4 group terminates with the hydroxy group.
- the preferred morpholino compound for use in the present invention is 3-(4- propyl-beptyl)-4-(2-hydoxyethyi) morpholine which is commonly known as Deimopinoi (CAS No. 79874-76-3).
- the morpholino compounds of the present invention can be used in their free base form or as a pharmaceutically acceptable salt thereof.
- pharmaceutically acceptable salts are the salts of acids such as acetic acid, phosphoric, acid, boric acid, hydrochloric acid, maieie acid, benzoic acid, citric acid, malic acid, oxalic acid, tartaric acid, succinic acid, glutaric acid, gentisic acid, valeric acid, gallic acid, beta-resorcydic acid, acetyl salicylic acid, salicylic acid, perchloric acid, barbituric acid, sulfanilic acid, phytic acid, p-nitro benzoic acid, stearic acid, palmitic acid, oleic acid, myristic acid, lauric acid and the like,
- the most preferred salt form Is of hydrochloric acid.
- a preferred compound is delmopinol hydrochloride (CAS No. 98092-92-3).
- the claimed morpholino compounds are not thought to have any substantial antimicrobial action themselves. Therefore, the claimed compounds may advantageously be used in combination with a treatment that reduces the number of bacteria.
- a composition containing the claimed morpholino compounds can be used as part of a skin-cleansing routine.
- the compositions of the present invention comprise a morpholino compound of formula (I) preferably used in combination with an antimicrobial agent.
- the antimicrobial agent can be any pharmaceutically acceptable compound which is effective against the bacteria associated with malodour, for example, synthetic antibacterial agents include triclosan, propyl-p-hydroxybenzoate, chlorhexidine gluconate, sodium lactoyl caprylate, trichlorocarbonilide, zinc undecylenate, and glycerolether.
- synthetic antibacterial agents include triclosan, propyl-p-hydroxybenzoate, chlorhexidine gluconate, sodium lactoyl caprylate, trichlorocarbonilide, zinc undecylenate, and glycerolether.
- natural antimicrobial actives include mono- and oligo- glyceryl fatty acid esters that are derived from plants and animals. Suitable antimicrobials will be apparent to the skilled person. For the avoidance of doubt, ail combinations of each of the composition ingredients described herein are within the scope of the invention.
- compositions for use in the present invention are intended for topical application to the skin.
- the compositions may be in the form of a spray, stick (dispersions of the compositions of the invention in wax-like bases), roll-on
- the composition can be hydrophilic or hydrophobic.
- the composition can be an aqueous composition, although other suitable solvents, such as alcohols or other organic solvents, may be used. A combination of solvents may also be used.
- the composition can be in the form of a microemulsion or a liquid crystal.
- Topically administrate compositions may also comprise a matrix in which the composition of the invention is dispersed so that the compound of formula (!) is held in contact with the skin.
- the claimed morpholino compound should be included in the composition at a level at which it is effective, which can be determined on the basis of the severity of the condition.
- the compound of the invention may be present in any suitable concentration. Typically, the compound is present in a concentration of from 0.01 %(w/v) to 20% (w/v) e.g. 15% (w/v), preferably from 0.01 % (w/v) to 10% (w/v), preferably from 0.1 % (w/v) to 5% (w/v) and most preferably from 1 % (w/v) to 3% (w/v) e.g. 2% (w/v).
- a suitable level can easily be selected by a person skilled in the art.
- an antimicrobial or antibiotic and/or other additional component is included in the composition, these are also included at an effective level which can easily be determined by a person skilled in the art.
- the deodorants according to the invention can be present in the form of aerosols, i.e. preparations which can be sprayed from aerosol containers, squeeze bottles or by a pump device, or in the form of liquid compositions which can be applied by means of roil-on devices, but also in the form of W/O or O/W emulsions, e.g. creams or lotions, which can be applied from conventional bottles and containers.
- aerosols i.e. preparations which can be sprayed from aerosol containers, squeeze bottles or by a pump device
- liquid compositions which can be applied by means of roil-on devices
- W/O or O/W emulsions e.g. creams or lotions
- Customary cosmetic carriers which can be employed for the preparation of the deodorizing compositions according to the invention, in addition to wafer, ethano! and isopropanoi, glycerol and propylene glycol, are skin care fatty or fat-like substances, such as decyi oieate, cetyi alcohol, cetyistearyi alcohol and 2- octyldodecanoi, in the quantative ratios customary for such preparations, and mucigenous substances and thickening agents, e.g.
- Suitable propeilants for cosmetic deodorants according to the invention which can be sprayed from aerosol containers are the customary known readily volatile liquefied propeilants, for example hydrocarbons (propane, butane and isobutane), which can be employed on their own or as a mixture with one another. Compressed air can also be advantageously used.
- CFCs chlorofluorohydrocarbons
- Emulsifiers which have proved suitable for the preparation of the cosmetic deodorants according to the invention which are advantageously to be applied to the desired areas of skin as liquid preparations by means of roll-on device, and which can be used in the compositions in a small amount, e.g. 2 to 5% by weight, relative to the total composition, are non-ionic types, such as po!yoxyethy!ene fatty alcohol ethers, e.g. cetyistearyl alcohol polyethylene glycol ethers having 12 to 20 ethylene oxide units added per molecule cetyistearyl alcohol as well as sorbitan ester and sorbitan ester/eihylene oxide compounds (e.g. sorbitan monostearate and polyoxyethylenesorbitan monostearate) and long-chain higher molecular weight waxy poiyglycol ethers.
- non-ionic types such as po!yoxyethy!ene fatty alcohol ethers, e.g. cetyistearyl alcohol polyethylene
- perfume, colorants, antioxidants e.g. alpha-tocopheroi and its derivatives or butylated hydroxytp!uene (BHT ⁇ 2,6-di- tert-butyl-4-methylphenol
- suspending agents, buffer mixtures or other customary cosmetic basis can be admixed to the deodorizing cosmetic agents according to the invention, whose pH is preferably adjusted, e.g. by customary buffer mixtures.
- the amounts of cosmetic carriers and perfume to be employed in each case can easily be determined by the person skilled in the art by simple trial and error depending on the nature of the particular product.
- those substances and perfume oils are also suitable which are stable, do not irritate the skin and as such already have antibacterial or bacteriostatic properties.
- the preparation of the cosmetic compositions can be carried out in the customary manner, by simple mixing while stirring, optionally with gentle warming.
- the fatty phase and the water phase are prepared separately, for example, if appropriate with heating, and then emulsified. Otherwise the customary rules for making up cosmetic formulations, which are familiar to the person skilled in the art, are to be observed.
- the suspension basis for this can advantageously be chosen from the group consisting of silica gels (e.g. those which are obtainable under the trade name Aerosii®) kieseiguhr, talc, modified starch, titanium dioxide, silk powder, nylon powder, polyethylene powder and related substances.
- Example 1 The liquid phase of Example 1 or Example 2 is introduced into aerosol containers toqelher with a propane/butane 2.7 mixture in the ratio 39:61 .
- Example 3 The liquid phase of Example 1 or Example 2 is introduced into aerosol containers toqelher with a propane/butane 2.7 mixture in the ratio 39:61 .
- the constituents of (a) are dispersed, water (b) is added, and the mixture is left to swell at room temperature, and a solution of the constituents mentioned under (c) is added after about 15 minutes.
- the resulting mixture is homogenized and can be transferred to ro!S-on containers.
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Abstract
The present invention relates to deodorant compositions comprising morpholino compounds and their use in preventing or reducing body odour. Also provided is a method of reducing or preventing body odour.
Description
Deodorant formulations
Field of the inve tio
The present invention relates to the reduction or prevention of body odour and specifically to deodorant compositions comprising a morpholino compound and to their use in improving the odour of the surface of the axilla.
Background to the invention
The axilla (or armpit, underarm, or oxter) is the area of the human body directly under the joint where the arm connects to the shoulder. The contents of the axilla include the axillary vein and artery, as well as the brachial plexus, lymph nodes and fat. Axilla is the space between the side of the thorax and the upper arm. The term "underarm" typically refers to the outer surface of the axilla. However, the terms are sometimes used interchangeably in casual contexts. Colloquially, armpit refers to an object or place which is smelly, greasy or otherwise undesirable. Underarm hair usually grows in the underarms of both females and males, beginning in adolescence. Body odour, sometimes colloquially abbreviated as B.O., is the smell of bacteria growing on the body. The bacteria multiply rapidly in the presence of sweat, but sweat itself is almost completely odourless to humans.
The condition can be known medically as bromhidrosis, apocrine bromhidrosis, bromidrosis, osmidrosis, ozochrotia, fetid sweat, body smell or malodourous sweating.
Body odour can smell specific to the individual and can be used to identify people. An individual's body odour is influenced by diet, lifestyle, gender, genetics, health and medication.
Human secretory glands are primarily divided into 2 types: apocrine and eccrine. Eccrine glands are distributed over the entire skin surface, where they are
involved in thermoregulation by means of sweat production. In contrast, apocrine glands have a limited distribution involving the axilla, genital skin, and breasts. Apocrine elements are also found in the periorbital and periauricular areas. Apocrine glands have no thermoregulatory role but are responsible for characteristic pheromonal odours. They secrete a small amount of oily fluid, which is odourless upon reaching the skin surface. The characteristic odour is due to bacterial decomposition of the oily fluid. Studies have shown that in comparison to controls, individuals with bromhidrosis display more numerous and larger apocrine glands.
Propionic acid (propanoic acid) is present in many sweat samples. This acid is a breakdown product of some amino acids by propionibacteria, which thrive in the ducts of adolescent and adult sebaceous glands. Because propionic acid is chemically similar to acetic acid with similar characteristics including odour, body odours may be identified as having a vinegar-like smell by certain people. Isovaleric acid (3-methyl butanoic acid) is the other source of body odour as a result of actions of the bacteria Staphylococcus epidermidis, which is also present in several strong cheese types. Body odour is also caused by the actions of skin flora, including members of Corynebacterium, which manufacture enzymes called lipases that break down the lipids in sweat to create smaller molecules. These smaller molecules smell, and give body odour its characteristic aroma. Body odour may be reduced or prevented or even aggravated by using deodorants, antiperspirants, disinfectants (e.g., triclosan), special soaps or foams with antiseptic plant extracts such as ribwort and liquorice, chlorophyllin ointments and sprays topically, and chlorophyllin supplements internally. Although body odour is commonly associated with hygiene practices, its presentation can be affected by changes in diet as well as the other factors discussed above.
Efforts are made to prevent or reduce body odour by using antiperspirants and deodorants. The terms antiperspirant and deodorant are colloquially interchangeable. However, they are differentiated in that antiperspirants seek to reduce armpit malodour through reduction of perspiration, whilst deodorants disguise the existence of malodour. Both are often present in single cosmetic products.
Antiperspirants include aluminium salts, which cause mechanical obstruction of eccrine sweat ducts. Aluminium has been associated with undesirable effects such as Alzheimer's Disease, DNA alterations and epigenetic effects. Titanium salts are also used as antiperspirants.
Water-insoluble films of polymers create occlusion on the axillary skin, thereby reducing the underarm wetness. Such films are a barrier to the passage of sweat. In general, film-forming antiperspirant polymers have been described as being capable of a greater perspiration reduction compared with traditional antiperspirant salts. Polymers used should be occlusive, insoluble in water, high in degree of adhesion, and nontoxic. Several polymers have been applied for the occlusive effects, including polyvinyl alcohol derivatives, chloroacetate derivatives of hydroxy polymers, spherical calcium alginate, and octylacrylamide/acrylate copolymer.
Fragrance compositions have been used to mask the unpleasant body odour since ancient times. Generally, fragrance compositions can be classified into three categories, namely natural, semi-synthetic, and synthetic. Natural fragrances are obtained from living organisms, that is, plants and animals. Plants are major sources of essential oils and aromatic substances. Plant fragrances include the extracts of stems, leaves, fruits, roots, and woods. Civet and beaver are examples of animal fragrance materials. Nowadays, the use of animal sources is not practical due to ethical and legal issues. Natural fragrance compositions can be used as precursors for semi-synthetic fragrances. By chemical alteration, intermediate natural compounds can be converted into semisynthetic substances. Synthetic fragrances are prepared by synthesis methods.
The compounds obtained possess aromatic scents that somewhat resemble natural ingredients. In general, synthetic fragrances are products of esters, aldehydes, alcohols, and ethers. !n addition to masking malodour, some fragrances have been shown to possess antimicrobial properties. In general, fragrance compositions at 0.2-1.5% levels are employed in deodorant products. One should be aware that many fragrance compounds could cause skin irritation, sensitization, or allergic contact dermatitis. United States Patent 538070715 discloses that the long-lasting fragrance compositions could be achieved with the fixative agent, acetyl hexamethyl tetraiin.
Sodium bicarbonate and zinc carbonate are examples of odour-neutralizing agents. These agents work by neutralizing certain odourous fatty acids that contribute to axillary odour. Sodium carbonate is colorless crystals or white, crystalline powder that is soluble in water. With respect to formulation development, sodium carbonate is not easily formulated because its stability is influenced by aqueous solution and high temperature (above 50°C). Unlike sodium carbonate, zinc carbonate is practically insoluble in water. Besides reducing the underarm odour, zinc carbonate possesses mild astringent property.
Aliphatic diols and their esters work by destroying the bacteria that cause unpleasant body odour, it has been reported that antiperspirants and deodorants containing these compounds are effective and nontoxic to human. Examples of aliphatic diols include aliphatic 1 ,3-diols such as 1 ,3- pentanediol, 1 ,3- hexanedioi, and 1 ,3-heptanediol. Several esters of aliphatic diols have been disclosed such as 1 ,3- butanedioi-1 -monopalmitate, 1 ,3-hexanedioi-1 - monoacetate, and 1 ,3-heptanedioi-1 -monoocianoaie, The amounts of these active ingredients used in the cream and stick formulations vary greatly from 2.0% to 40.0% by weight
Esterase inhibitors are compounds that are capable of inhibiting the exoenzymes from the axillary-resident bacteria. Such exoenzymes are able to transform the odourless water-soluble precursors of androstenoi into the volatile steroids, which is responsible for axillary odour. Triethyl citrate, trimethyl citrate, and zinc salts such as zinc glycinate are examples of esterase inhibitors. Zinc giycinate is an odourless, white crystalline substance that is slightly soluble in water and insoluble in alcohol. The dual function of zinc glycinate as bacterial growth inhibitor and chemical neufraiizer of body odours when used in the concentrations of 1-20% is disclosed in United States Patent 4585693.
Antimicrobial agents are able to prevent or reduce axillary odour by inhibiting or suppressing the growth of microbial populations responsible for malodour generation. Over the past decades, the majority of commercial deodorant products contain antimicrobial agents, for example triclosan, as active ingredients. Triclosan is the most widely used synthetic antibacterial. According to European Economic Community Council directive 76/768/CEE (Appendix VI 81976), the highest content of triclosan approved to be used in deodorants is 0.30% w/w. United States Patent 558715221 discloses deodorant composition containing 0.25% w/w triclosan and using diben-zylidine sorbitol as a gelling agent. Other synthetic antibacterial agents include propyi-p-hydroxybenzoate, chlorhexidine gluconate, sodium lactoyl caprylate, trichlorocarboniiide, zinc undecylenate, and glycerolether. Examples of natural antimicrobial actives include mono- and oiigo-glycryl fatty acid esters that are derived from plants and animals
Chitosan is a major derivative of chitin, a naturally occurring polysaccharide that is a main constituent of the shells of lobsters and crabs, in addition, exoskeletons of insects and cell walls of fungi are composed of chitin constituent. Chitin is a linear polymer composed of β (1 → 4) linked 2- acetamido- 2-deoxy~P-D-glucose units (or N-acetyi-D-giucosamine). Sufficient deacetylation of chitin yields chitosan, a cationic biopoiymer of N-acetyl-D- glucosamine and D-giucosamine. Chitosan is soluble in acidic solutions but insoluble in water. Chitosan has deodorizing effect due to its bacteriostatic
property. The long-lasting deodorizing activity can be achieved by using nanosca!e chitosan and/or chitosan derivatives, having particle diameter in the range 10-300 nm. The contents of nanochitosan and derivatives are in the ranges of 0.01-5% by weight.
Antiperspirants and deodorants in conventional formulations such as original emulsions (milky liquids or creams), sprays and sticks (dispersions of actives in wax-like bases) provide good contact for the product with the skin. However, they leave a residue on the skin after application, resulting in feeling sticky and undesirable looking. Therefore, new formulations such as microemulsions and liquid crystals are developed to overcome the disadvantages of the conventional ones and to provide alternative choices to satisfy the consumers.
Although existing deodorants and antiperspirants are effective to some degree, there is room for improvement in this fieid and there remains a strong need for effective, safe and environmentally friendly products.
Summary of the invention
The present invention is based on the surprising discovery that morphoiino compounds of formula (I), and their derivatives, are useful in the reduction of body odour at the surface of the human axilla.
Compounds of formula (!) have the general formula:
wherein R. is a straight or branched alkyi group containing 8 to 16 carbon atoms at the 2- or 3-position of the morphoiino ring, and i¾ is a straight or branched aikyl group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position.
Deimopinoi, a compound of Formula (I), has been shown to reduce colonization of the tooth surface by inhibiting defined stages of orai plaque biofi!m formation (Klinge B, Matsson L, Attstrom R et al, Clin Periodontol 1996; 23: 542-547, Rundegren J, Arnebrant T, Caries Res 1992;26:281 -285 and Rundegren J, Simonsson T, Petersson L, Hansson E. J Dent Res 1992;71 :1792-1796). Deimopinoi has been shown to have poor antimicrobial properties.
Bacterial colonization of the surface of the axilla has not been shown to be dependent on biofiim formation. Therefore it is surprising that deimopinoi is effective in reducing underarm body odour. In any case, even if biofiim formation was shown to be important for bacterial colonization of the armpit, one would expect the biofiim to be materially different in character and microbial composition to the biofiims which deimopinoi is known to be effective against,
According to a first aspect, there is a composition comprising a morpholino compound having the general formula (!)
wherein Ri is a straight or branched aikyi group containing 8 to 16 carbon atoms at the 2- or 3-position of the morpholino ring, and R? is a straight or branched aikyi group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof, for use in the reduction or prevention of body odour. According to a second aspect, there is a method of reducing or preventing body odour, the method comprising topical application to the skin of a composition comprising a morpholino compound having the general formula
wherein R. is a straight or branched alkyl group containing 8 to 16 carbon atoms at the 2- or 3-position of the morphoSino ring, and f¾? is a straight or branched a!kyl group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof.
According to a third aspect, there is a deodorant composition suitable for dermatoiogical application comprising a morpho!ino compound having the general formula
wherein R-i, is a straight or branched alkyl group containing 8 to 16 carbon atoms at the 2~ or 3-position of the morpho!ino ring, and R2 is a straight or branched alkyl group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof.
The term "deodorant composition" of the present invention is understood to mean a composition which deodorizes the surface of the skin. The "deodorant composition" of the invention may be an antiperspirant or a deodorant as per the definitions applied to these terms in the prior art. The deodorant composition of the invention may therefore comprise a compound of formula (!) optionally in combination with one or more of a fragrance, an antiperspirant and an antibacterial agent for topical administration.
According to a fourth aspect, there is an aerosol canister, pump spray container or roil-on container for dermatological application comprising a composition according to the invention.
Description of the invention
The claimed morpholino compounds are beneficial in the reduction of malodour at the surface of the human axilla. As used herein, the term "malodour" refers to the smell caused by bacteria growing on the body. The condition can be known medically as bromhidrosis, apocrine bromhidrosis, bromidrosis, osmidrosis, ozochrotia, fetid sweat, body smell or malodourous sweating.
The claimed morpholino compounds are known per se as disclosed in US 4,894,221 and US 5,082,653, the content of which are incorporated herein by reference.
Sn the present invention, the morpholino compounds are defined according to the general formula shown above. In a preferred embodiment of the present invention, the sum of carbon atoms in the groups R¾ and f¾ is at least 10, and is preferably between 10 and 20, In a further preferred embodiment, the f¾ group terminates with the hydroxy group.
The preferred morpholino compound for use in the present invention is 3-(4- propyl-beptyl)-4-(2-hydoxyethyi) morpholine which is commonly known as Deimopinoi (CAS No. 79874-76-3).
The morpholino compounds of the present invention can be used in their free base form or as a pharmaceutically acceptable salt thereof. Some examples of pharmaceutically acceptable salts are the salts of acids such as acetic acid, phosphoric, acid, boric acid, hydrochloric acid, maieie acid, benzoic acid, citric acid, malic acid, oxalic acid, tartaric acid, succinic acid, glutaric acid, gentisic acid, valeric acid, gallic acid, beta-resorcydic acid, acetyl salicylic acid, salicylic acid, perchloric acid, barbituric acid, sulfanilic acid, phytic acid, p-nitro benzoic
acid, stearic acid, palmitic acid, oleic acid, myristic acid, lauric acid and the like, The most preferred salt form Is of hydrochloric acid. A preferred compound is delmopinol hydrochloride (CAS No. 98092-92-3). The claimed compounds can be manufactured by any known method, for example, that disclosed in US 5,082,653 and WO 90/14342 herein incorporated by reference.
The claimed morpholino compounds are not thought to have any substantial antimicrobial action themselves. Therefore, the claimed compounds may advantageously be used in combination with a treatment that reduces the number of bacteria. For example, a composition containing the claimed morpholino compounds can be used as part of a skin-cleansing routine. The compositions of the present invention comprise a morpholino compound of formula (I) preferably used in combination with an antimicrobial agent. The antimicrobial agent can be any pharmaceutically acceptable compound which is effective against the bacteria associated with malodour, for example, synthetic antibacterial agents include triclosan, propyl-p-hydroxybenzoate, chlorhexidine gluconate, sodium lactoyl caprylate, trichlorocarbonilide, zinc undecylenate, and glycerolether. Examples of natural antimicrobial actives include mono- and oligo- glyceryl fatty acid esters that are derived from plants and animals. Suitable antimicrobials will be apparent to the skilled person. For the avoidance of doubt, ail combinations of each of the composition ingredients described herein are within the scope of the invention.
The compositions for use in the present invention are intended for topical application to the skin. The compositions may be in the form of a spray, stick (dispersions of the compositions of the invention in wax-like bases), roll-on
(usually an emulsion), cream, ointment or gel. The composition can be hydrophilic or hydrophobic. The composition can be an aqueous composition, although other suitable solvents, such as alcohols or other organic solvents, may
be used. A combination of solvents may also be used. The composition can be in the form of a microemulsion or a liquid crystal.
Topically administrate compositions may also comprise a matrix in which the composition of the invention is dispersed so that the compound of formula (!) is held in contact with the skin.
The claimed morpholino compound should be included in the composition at a level at which it is effective, which can be determined on the basis of the severity of the condition. The compound of the invention may be present in any suitable concentration. Typically, the compound is present in a concentration of from 0.01 %(w/v) to 20% (w/v) e.g. 15% (w/v), preferably from 0.01 % (w/v) to 10% (w/v), preferably from 0.1 % (w/v) to 5% (w/v) and most preferably from 1 % (w/v) to 3% (w/v) e.g. 2% (w/v). A suitable level can easily be selected by a person skilled in the art.
Where an antimicrobial or antibiotic and/or other additional component is included in the composition, these are also included at an effective level which can easily be determined by a person skilled in the art.
The deodorants according to the invention can be present in the form of aerosols, i.e. preparations which can be sprayed from aerosol containers, squeeze bottles or by a pump device, or in the form of liquid compositions which can be applied by means of roil-on devices, but also in the form of W/O or O/W emulsions, e.g. creams or lotions, which can be applied from conventional bottles and containers.
Customary cosmetic carriers which can be employed for the preparation of the deodorizing compositions according to the invention, in addition to wafer, ethano! and isopropanoi, glycerol and propylene glycol, are skin care fatty or fat-like substances, such as decyi oieate, cetyi alcohol, cetyistearyi alcohol and 2- octyldodecanoi, in the quantative ratios customary for such preparations, and mucigenous substances and thickening agents, e.g. hydroxyethyi- or
hydrocypropySce!!u!ose, polyacryiic acid and poiyviynipyrroiidone, but in addition, in smaii amounts, also cyclic silicone oils (polydimethyisiloxanes) and liquid poiymethyiphenysiioxanes of low viscosity. Suitable propeilants for cosmetic deodorants according to the invention which can be sprayed from aerosol containers are the customary known readily volatile liquefied propeilants, for example hydrocarbons (propane, butane and isobutane), which can be employed on their own or as a mixture with one another. Compressed air can also be advantageously used.
The person skilled in the art of course knows that there are non-toxic propeilants which would be fundamentally suitable for the present invention but which nevertheless are undesirable because of a questionable action on the environment or other accompanying circumstances, in particular chlorofluorohydrocarbons (CFCs).
Emulsifiers which have proved suitable for the preparation of the cosmetic deodorants according to the invention which are advantageously to be applied to the desired areas of skin as liquid preparations by means of roll-on device, and which can be used in the compositions in a small amount, e.g. 2 to 5% by weight, relative to the total composition, are non-ionic types, such as po!yoxyethy!ene fatty alcohol ethers, e.g. cetyistearyl alcohol polyethylene glycol ethers having 12 to 20 ethylene oxide units added per molecule cetyistearyl alcohol as well as sorbitan ester and sorbitan ester/eihylene oxide compounds (e.g. sorbitan monostearate and polyoxyethylenesorbitan monostearate) and long-chain higher molecular weight waxy poiyglycol ethers.
In addition to the constituents mentioned, perfume, colorants, antioxidants (e.g. alpha-tocopheroi and its derivatives or butylated hydroxytp!uene (BHT~2,6-di- tert-butyl-4-methylphenol) in amounts from 0.01 to 0.03% by weight, suspending agents, buffer mixtures or other customary cosmetic basis can be admixed to the deodorizing cosmetic agents according to the invention, whose pH is preferably adjusted, e.g. by customary buffer mixtures.
The amounts of cosmetic carriers and perfume to be employed in each case can easily be determined by the person skilled in the art by simple trial and error depending on the nature of the particular product.
For perfuming, optionally those substances and perfume oils are also suitable which are stable, do not irritate the skin and as such already have antibacterial or bacteriostatic properties. The preparation of the cosmetic compositions can be carried out in the customary manner, by simple mixing while stirring, optionally with gentle warming. For emulsions, the fatty phase and the water phase are prepared separately, for example, if appropriate with heating, and then emulsified. Otherwise the customary rules for making up cosmetic formulations, which are familiar to the person skilled in the art, are to be observed.
Sf the combinations according to the invention are to be incorporated into powder sprays, the suspension basis for this can advantageously be chosen from the group consisting of silica gels (e.g. those which are obtainable under the trade name Aerosii®) kieseiguhr, talc, modified starch, titanium dioxide, silk powder, nylon powder, polyethylene powder and related substances.
The following Examples illustrate the invention: Examples
Aerosol spray, liquid phase
Component % w/v
Octyldodecanol 0.50
Fatty acid mixture 0.50
Perfume q.s
Delmopinol hydrochloride 0.10
Ethyl alcohol to 100.00
Example 2
Aerosol spray, liquid phase
Com onent % w/v
Octyldodecanol 0.50
Coconut fatty acid 0.20
Perfume q.s
Delmopinol hydrochloride 0.20
Isopropyl alcohol to 100.00
The liquid phase of Example 1 or Example 2 is introduced into aerosol containers toqelher with a propane/butane 2.7 mixture in the ratio 39:61 . Example 3
Roil-on gel
Component % w/v
(a)
1 ,3-hutyiene glycol 2.00
Hydroxyethy!cei!uiose 0.50
(b)
Water to 100.00
(c)
Ethyl alcohol 60.00
PEG 40/hydrogenated castor oil 2.00
Fatty acid mixture 0.50
Delmopinol hydrochloride 0.10
Perfume q.s
Water to 1000.00
Roii-on gel
The constituents of (a) are dispersed, water (b) is added, and the mixture is left to swell at room temperature, and a solution of the constituents mentioned under (c) is added after about 15 minutes. The resulting mixture is homogenized and can be transferred to ro!S-on containers.
Claims
Chasms
A composition comprising a morpholino compound having the general
wherein Ri is a straight or branched a!kyl group containing 8 to 16 carbon atoms at the 2- or 3-position of the morphoiino ring, and f¾ is a straight or branched alky! group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable saits thereof, for use in the reduction or prevention of body odour.
2. The composition of claim 1 , wherein the sum of the carbon atoms in the groups R-i and R2 is at least 10, preferably between 10 and 20.
3. The composition of claim 1 or claim 2, wherein R2 terminates with the hydroxy group.
4. The composition of any preceding claim, wherein the morpholino compound is 3-(4-propyi-heptyi) -4-(2-hydroxyethyi) morpho!ine.
5. The composition of any preceding claim, further comprising an antimicrobial agent.
6. The composition of claim 5, wherein the antimicrobial agent is an antibiotic, preferably an antibiotic selected from the group consisting of triclosan, propyl-p-hydroxybenzoate, chlorhexidine gluconate, sodium lactoyl caprylate, trichlorocarbonilide, zinc undecylenate,and glycerolether.
7. The composition of any preceding ciaim, further comprising an anti- perspirant agent.
8. A method of reducing or preventing body odour, the method comprising topical application to the skin of a composition comprising a morpholino compound having the genera! formula
wherein R. is a straight or branched alkyi group containing 8 to 16 carbon atoms at the 2- or 3-position of the morpholino ring, and f¾? is a straight or branched aikyl group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof.
9. The method of claim 8, wherein the morpholino compound is as defined as in any of claims 2 to 4.
10. The method of claim 8 or claim 9, wherein the composition further comprises an antimicrobial agent.
1 1. The method of any of claims 8 to 10. wherein the composition further comprises an anti-perspirant agent.
12. A deodorant composition suitable for dermatological application comprising a morpholino compound having the general formula
wherein R1 ; is a straight or branched alkyi group containing 8 to 16 carbon atoms at the 2- or 3-position of the morpholino ring, and f¾ is a straight or branched alkyi group containing 2 to 10 carbon atoms, substituted with a hydroxy group except in the alpha-position, or pharmaceutically acceptable salts thereof.
13, The deodorant composition of ciaim 12, further comprising any of the features of claims 2 to 7. 14, An aerosol canister, pump spray container or roll-on container for dermatologicai application comprising a composition according to ciaim 12 or claim 13.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GB1105162.0 | 2011-03-28 | ||
GB201105162A GB201105162D0 (en) | 2011-03-28 | 2011-03-28 | Improved deodorant formulations |
Publications (2)
Publication Number | Publication Date |
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WO2012131363A2 true WO2012131363A2 (en) | 2012-10-04 |
WO2012131363A3 WO2012131363A3 (en) | 2013-07-18 |
Family
ID=44067474
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/GB2012/050690 WO2012131363A2 (en) | 2011-03-28 | 2012-03-28 | Deodorant formulations |
Country Status (2)
Country | Link |
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GB (1) | GB201105162D0 (en) |
WO (1) | WO2012131363A2 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT201600130538A1 (en) * | 2016-12-23 | 2018-06-23 | Lundbeck Pharmaceuticals Italy S P A | PROCESS FOR DELMOPINOL PRODUCTION |
US10717747B2 (en) | 2016-12-23 | 2020-07-21 | Lundbeck Pharmaceuticals Italy S.P.A. | Method for the manufacturing of 2-(3-(alkyl and alkenyl)morpholino)-ethan-1-ols |
DE102020101190A1 (en) | 2020-01-20 | 2021-07-22 | Henkel Ag & Co. Kgaa | Cyclic amine salts to reduce sweat secretion |
US11384056B2 (en) | 2016-12-23 | 2022-07-12 | Lundbeck Pharmaceuticals Italy S.P.A. | Method for the manufacturing of delmopinol intermediates |
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US4565693A (en) | 1981-11-09 | 1986-01-21 | Colgate-Palmolive Company | Deodorant composition |
US4894221A (en) | 1981-03-19 | 1990-01-16 | Ab Ferrosan | Method of treating plaque using morpholine compounds |
WO1990014342A1 (en) | 1989-05-24 | 1990-11-29 | Pharmacia Ab | Substituted isoxazolidines and isoxazolines |
US5082653A (en) | 1990-10-31 | 1992-01-21 | Warner-Lambert Company | Anti-plaque compositions comprising a combination of morpholinoamino alcohol and antibiotic |
US5380707A (en) | 1993-08-13 | 1995-01-10 | The Mennen Company | Enhanced efficacy, long-lasting fragrance composition, and deodorant composition, for masking malodor, containing the fragrance composition |
Family Cites Families (1)
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US4851214A (en) * | 1988-09-07 | 1989-07-25 | Ici Americas Inc. | Deodorants containing N-soya-N-ethyl morpholinium ethosulfate |
-
2011
- 2011-03-28 GB GB201105162A patent/GB201105162D0/en not_active Ceased
-
2012
- 2012-03-28 WO PCT/GB2012/050690 patent/WO2012131363A2/en active Application Filing
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US4894221A (en) | 1981-03-19 | 1990-01-16 | Ab Ferrosan | Method of treating plaque using morpholine compounds |
US4565693A (en) | 1981-11-09 | 1986-01-21 | Colgate-Palmolive Company | Deodorant composition |
WO1990014342A1 (en) | 1989-05-24 | 1990-11-29 | Pharmacia Ab | Substituted isoxazolidines and isoxazolines |
US5082653A (en) | 1990-10-31 | 1992-01-21 | Warner-Lambert Company | Anti-plaque compositions comprising a combination of morpholinoamino alcohol and antibiotic |
US5380707A (en) | 1993-08-13 | 1995-01-10 | The Mennen Company | Enhanced efficacy, long-lasting fragrance composition, and deodorant composition, for masking malodor, containing the fragrance composition |
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Title |
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KLINGE B; MATSSON L; ATTSTROM R ET AL., CLIN PERIODONTOL, vol. 23, 1996, pages 542 - 547 |
RUNDEGREN J; ARNEBRANT T, CARIES RES, vol. 26, 1992, pages 281 - 285 |
RUNDEGREN J; SIMONSSON T; PETERSSON L; HANSSON E., J DENT RES, vol. 71, 1992, pages 1792 - 1796 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT201600130538A1 (en) * | 2016-12-23 | 2018-06-23 | Lundbeck Pharmaceuticals Italy S P A | PROCESS FOR DELMOPINOL PRODUCTION |
WO2018115096A1 (en) * | 2016-12-23 | 2018-06-28 | Lundbeck Pharmaceuticals Italy S.P.A. | Method for the manufacturing of delmopinol |
US10717747B2 (en) | 2016-12-23 | 2020-07-21 | Lundbeck Pharmaceuticals Italy S.P.A. | Method for the manufacturing of 2-(3-(alkyl and alkenyl)morpholino)-ethan-1-ols |
US10815251B2 (en) | 2016-12-23 | 2020-10-27 | Lundbeck Pharmaceuticals Italy S.P.A. | Method for the manufacturing of 2-(3-(alkyl and alkenyl)morpholino)-ethan-1-ols |
US10894778B2 (en) | 2016-12-23 | 2021-01-19 | Lundbeck Pharmaceuticals Italy S.P.A. | Method for the manufacturing of delmopinol |
US11384056B2 (en) | 2016-12-23 | 2022-07-12 | Lundbeck Pharmaceuticals Italy S.P.A. | Method for the manufacturing of delmopinol intermediates |
DE102020101190A1 (en) | 2020-01-20 | 2021-07-22 | Henkel Ag & Co. Kgaa | Cyclic amine salts to reduce sweat secretion |
Also Published As
Publication number | Publication date |
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GB201105162D0 (en) | 2011-05-11 |
WO2012131363A3 (en) | 2013-07-18 |
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