WO2012054515A2 - Alkoxyalkylamide compounds, methods of making same, and cosmetic compositions containing same - Google Patents

Abstract

The present invention is directed to alkoxyalkylamide compounds having the formulas (I)- (VI), methods of making the compounds, and cosmetic compositions containing the compounds. The compounds and cosmetic compositions containing thereof provide various advantageous properties to the human skin.

Description

ALKOXYALKYLAMIDE COMPOUNDS, METHODS OF MAKING SAME, AND COSMETIC COMPOSITIONS CONTAINING SAME

[0001] This application claims the benefit of priority from U.S. Provisional Application No. 61/394,546, which was filed on October 19, 2010, the content of which is incorporated by reference herein in its entirety.

BACKGROUND OF THE INVENTION

[0002] The present invention relates to alkoxyalkylamide compounds, methods of making the compounds, and cosmetic compositions containing the compounds The compounds and the cosmetic compositions containing thereof provide various advantageous properties to the human skin (including hair, nail and lip). The compounds and compositions may have, among others, moisturizing and/or softening properties and would be useful for treating and/or relieving mild to moderate dry skin. The compounds and compositions may also have collagen- production inducing and skin-lightening properties.

[0003] For most, if not all, having beautiful skin is very important, however, there are challenges in achieving and maintaining it. One of the many challenges is the exposure to the environments, e.g. , sun radiation, dryness of the air, chemical (natural and/or artificial) exposure that causes damages, etc. Another challenge is aging. Both exposure to the environments and aging may cause the skin to be dry, wrinkled or to have lines, and to lose its elasticity; they may also cause darkening/discoloration of the skin and the degradation of collagen fibers therein.

[0004] Dry skin is generally characterized by cracking, flaking, or scaling of the skin of the hands, feet, neck, face, or other parts of the body. Dry skin may result from a hereditary disorder known as ichthyosis which is a severe form of dry skin. The more common form of dry skin is a mild to moderate form of dry skin which arises due to exposure to low humidity, such as low humidity in the fall and winter seasons of the temperate climate zones. The low humidity gives rise to, in skin areas exposed thereto, a loss of moisture, resulting in the formation of fissures, chaps, cracks, or flakes in the affected skin areas.

[0005] Various compounds have been proposed for use in treating or relieving dry skin. These compounds are generally formulated with other materials for topical use in the form of a lotion, cream, or ointment.

[0006] Aging causes, among others, the degradation of collagen fibers in the skin. The degradation results in the skin being flaccid and lacking firmness. Aging, generally in combination with exposure to the sun, also causes discoloration/darkening of the skin. Attempts have been made to delay, or even reverse, the effects of aging by delaying the degradation and/or increasing collagen production; or by lightening or evening out the discoloration of the skin.

[0007] There is a need for a compound that can treat and/or relieve dry skin. There is also a need for a compound that can delay and/or prevent the effects of aging. Further, there is a need for a stable cosmetic composition containing such a compound that provides the benefits associated with the compound. SUMMARY OF THE INVENTION

[0008] The present invention is directed to an alkoxyalkylamide compound having the following general formula (I):

[0009] The present invention is also directed to a related alkoxyalkylamide compound having the following general formula (II):

[0010] The present invention is also directed to another related alkoxyalkylamide compound having the following general formula (III):

[0011] In formulas (I), (II), and (III), n is a whole number of 1 to 10, and m is a whole number of 1 to 10. In one embodiment, n is a whole number of 1 to 4. In another embodiment, m is a whole number of 1 to 4. In another embodiment, n is 3. In yet another embodiment, m is 1.

[0012] In yet another embodiment, the values of n and m are 3 and 1, respectively, as shown in formulas (IV), (V), and (VI):

[0013] The present invention includes methods of making the alkoxyalkylamide compounds having the formulas (I) - (VI). The method of making the alkoxyalkylamide compounds having the formulas (I) and (II) comprises reacting an alkoxyalkylamine of formula (VII) with ascorbic acid.

H₂N-(C_nH_2n)-0-(C_mH_2m+1 ) (VII)

In such method, n is a whole number of 1 to 10, and m is a whole number of 1 to 10. In one embodiment, n is a whole number of 1 to 4. In another embodiment, m is a whole number of 1 to 4. In another embodiment, n is 3. In yet another embodiment, m is 1.

[0014] The method of making the alkoxyalkylamide compounds having the formulas (IV) and (V) comprises reacting alkoxyalkylamine

(methoxypropylamine) of formula (VIII) with ascorbic acid.

H₂N-(CH₂)₃-0-CH₃ (VIII)

[0015] The alternative method of making the alkoxyalkylamide compound having formula (I) and the method of making the alkoxyalkylamide compound having formula (III) comprise the steps of: protecting the hydroxyl at either C-2 or C-3, and the hydroxyls at C-4, C-5, and C-6 of a compound of formula (IX); activating the unprotected hydroxyl at either C-2 or C-3; reacting the activated, protected compound with an alkoxyalkylamine of formula (VII); deprotecting the protected hydroxyl at either C-2 or C-3 and the protected hydroxyls at C- 1 and C- 4 to generate an intermediate; cyclizing the intermediate; oxidizing the deprotected hydroxyl at either C-2 or C-3; and deprotecting the hydroxyls C-5 and C-6. In formulas (I), (III), and (VII), n is a whole number of 1 to 10, and m is a whole number of 1 to 10. In one embodiment, n is a whole number of 1 to 4. In another embodiment, m is a whole number of 1 to 4. In another embodiment, n is 3. In yet another embodiment, m is 1.

[0016] The alternative method of making the alkoxyalkylamide compound having formula (IV) and the method of making the alkoxyalkylamide compound having formula (VI) comprise the steps of: protecting the hydroxyl at either C-2 or C-3, and the hydroxyls at C-4, C-5, and C-6 of a compound of formula (IX); activating the unprotected hydroxyl at either C-2 or C-3; reacting the activated, protected compound with an alkoxyalkylamine (methoxypropylamine) of formula (VIII); deprotecting the protected hydroxyl at either C-2 or C-3 and the protected hydroxyls at C-1 and C-4 to generate an intermediate; cyclizing the intermediate; oxidizing the deprotected hydroxyl at either C-2 or C-3; and deprotecting the hydroxyls C-5 and C-6.

[0017] In the methods of making alkoxyalkylamide compounds of formulas I, III, IV, and VI, the activating step comprises a step of forming a carbonate or a sulfonate. A step of forming a carbonate may be performed by a phosgene or a carbonyldiimidazole (CDI). [0018] The present invention is also directed to a cosmetic composition comprising up to 75% by weight of a compound of formula (I), (II), or (III), or a combination thereof. In formulas (I), (II), and (III), n is a whole number of 1 to 10, and m is a whole number of 1 to 10, e.g., n is a whole number of 1 to 4 and m is a whole number of 1 to 4. In one embodiment, n is 3 and m is 1.

[0019] The present invention is also directed to a cosmetic composition comprising up to 75% by weight of a compound of formula (IV), (V), or (VI), or a combination thereof.

DETAILED DESCRIPTION OF THE INVENTION

[0020] For the purposes of the present invention, the use of the term "cosmetic composition" is understood to mean a composition suitable for application to the human body. A cosmetic composition is typically applied to the body for beautifying, cleansing, moisturizing or otherwise treating the external surface of the body, including by cleansing, coloring, conditioning, or protecting the external surface of the body part such as, for example, the skin, nails, lips, or hair.

[0021] The cosmetic compositions of the present invention are compositions that contain alkoxyalkylamide compounds, described below. Examples of cosmetic compositions in which the present alkoxyalkylamide compounds can be used include skin moisturizers, sunscreens, self tanning compositions, after-sun care compositions, makeup, protein concentrates, antiwrinkle or anti-aging

compositions, skin firming compositions, skin lightening composition, topically applied therapeutic compositions, hair care compositions, shaving preparation compositions, depilatory compositions, and cleansers.

[0022] The present invention is directed to an alkoxyalkylamide compound having the general formula (I):

.... (I). [0023] The present invention is also directed to related alkoxyalkylamide compounds having the general formulas (II) and (III):

[0024] For the purposes of the present invention, in formulas (I), (II), (III), and (VII) (below), unless otherwise specified, n is a whole number of 1 to 10, and m is a whole number of 1 to 10.

H₂N-(C_nH2n)-0-(C_mH_2m+i ) (VII)

[0025] In one embodiment, the value of n is a whole number of 1 to 4. In another embodiment, the value of m is a whole number of 1 to 4. In another embodiment, the value of n is 3. In yet another embodiment, the value of m is 1. In an additional embodiment, the values of n and m are 3 and 1, respectively; as shown in alkoxyalkylamide compounds of the invention having formulas (IV), (V), and (VI), below:

[0026] The present invention includes methods of making the alkoxyalkylamide compounds having the formulas (I) - (VI). A person of ordinary skill could readily ascertain the reaction conditions to carry out the methods described herein.

[0027] The method of making the alkoxyalkylamide compounds having the formulas (I) and (II) comprises reacting an alkoxyalkylamine of formula (VII) with ascorbic acid. In such method, the value of n in compounds of formulas (I), (II), and (VII) can be a whole number of 1 to 10, and the value of m can be a whole number of 1 to 10. In one embodiment, the value of n is a whole number of 1 to 4. In another embodiment, the value of m is a whole number of 1 to 4. In another embodiment, the value of n is 3. In yet another embodiment, the value of m is 1.

[0028] The chemical reactions of the above-mentioned method are shown in the below schemes:

Formula (I)

Scheme 1

0-(C_mH_2m+1)

Formula (II)

Scheme 2

[0029] The method of making the alkoxyalkylamide compounds having the

formulas (IV) and (V) comprises reacting methoxypropylamine of formula (VIII) (below) with ascorbic acid.

H₂N-(CH₂)₃-0-CH_{3 (vni)}

[0030] The chemical reactions of the above-mentioned method are shown in the below schemes:

Formula (IV)

Scheme 3

Scheme 4

[0031] The products in Schemes 1 and 2 or Schemes 3 and 4 may be formed in the same reaction, and, if so, may be separated by chromatographic techniques such as flash chromatography, thin-layer chromatography, gel chromatography, HPLC, and/or reverse-phase HPLC.

[0032] The alternative method of making the alkoxyalkylamide compound having formula (I) and the method of making the alkoxyalkylamide compound having formula (III) comprise the steps of: protecting the hydroxyl at either C-2 or C-3, and the hydroxyls at C-4, C-5, and C-6 of a compound of formula (FX);

activating the unprotected hydroxyl at either C-2 or C-3; reacting the activated, protected compound with an alkoxyalkylamine of formula (VII); deprotecting the protected hydroxyl at either C-2 or C-3 and the protected hydroxyls at C- 1 and C- 4 to generate an intermediate; cyclizing the intermediate; oxidizing the deprotected hydroxyl at either C-2 or C-3; and deprotecting the hydroxyls C-5 and C-6. In such method, the value of n in compounds having formulas (I), (III), and (VII) can be a whole number of 1 to 10. The value of m can be a whole number of 1 to 10. In one embodiment, the value of n is a whole number of 1 to 4. In another embodiment, the value of m is a whole number of 1 to 4. In another embodiment, the value of n is 3. In yet another embodiment, the value of m is 1.

[0033] The chemical reactions of the above-mentioned method are shown in the below scheme:

F

Formula (ΙΠ) Formula (I)

Scheme 5

[0034] The alternative method of making the alkoxyalkylamide compound having formula (IV) and the method of making the alkoxyalkylamide compound having formula (VI) comprise the steps of: protecting the hydroxyl at either C-2 or C-3, and the hydroxyls at C-4, C-5, and C-6 of a compound of formula (IX); activating the unprotected hydroxyl at either C-2 or C-3; reacting the activated, protected compound with a methoxypropylamine of formula (VIII); deprotecting the protected hydroxyl at either C-2 or C-3 and the protected hydroxyls at C-l and C-4 to generate an intermediate; cyclizing the intermediate; oxidizing the deprotected hydroxyl at either C-2 or C-3; and deprotecting the hydroxyls C-5 and C-6.

[0035] The chemical reactions of the above-mentioned method are shown in the below scheme:

Formula (IX)

\

Formula (VI) Formula (IV)

Scheme 6

[0036] In Schemes 5 and 6, the protection steps may yield a mixture of products unprotected at C-2 and/or C-3. Similarly, the activation step(s) may yield a mixture of products activated at C-2 and/or C-3. The products may be separated by chromatographic techniques such as flash chromatography, thin-layer chromatography, gel chromatography, HPLC, and/or reverse-phase HPLC.

[0037] In Schemes 5 and 6, P¹ to P⁶ may be the same or different protecting groups, e.g., acetyl group. The use of protecting groups are well known in the art and is disclosed, for example, by Wuts et al., "Greene's Protective Groups in Organic Synthesis," 4^th ed., Ch. 2 and 5, 2006, incorporated by reference herein in its entirety. A 1 and A 2 may be the same or different activating groups, e.g., sulfonate (tosyl or mesyl), or carbonate (methyl).

[0038] In one embodiment, the activating step includes the step of forming a carbonate or a sulfonate on the hydroxyl. In another embodiment, the step of forming the carbonate is performed by a phosgene or a carbonyldiimidazole

(CDI).

[0039] It is understood that, in addition to amines of formulas (VII) and (VIII), other amines may be used in the above-mentioned method to produce amide compounds having beneficial properties for the skin. Examples of the amines include but are not limited to:

Tranexamic acid,

Sphingosine,

Hydroxyproline, and

N-acetyl-L-Hydroxyproline.

[0040] The alkoxyalkylamide compounds of the present invention possess many advantageous properties for the skin and may be useful for the treatment of various skin conditions. For example, the alkoxyalkylamide compounds may be useful for the treatment of mild or moderate form of dry skin as they are believed to have moisturizing and/or skin-softening properties. Accordingly, the alkoxyalkylamide compounds may prevent or cure the occurrence of any cracking, flaking, scaling, or chapping of the skin caused by dry skin. In addition, the alkoxyalkylamide compounds may be used to prevent, cure, or ameliorate acne, psoriases, seborrhea, keratose, diaper rash, sunburn, and windburn.

[0041] The alkoxyalkylamide compounds may also be useful for the treatment, preventively or curatively, of wrinkles and/or fine lines, wizened skin, a lack of elasticity and/or of tonus of the skin, thinning of the dermis, the degradation of collagen fibers, flaccid skin, thinned skin, and the internal degradation of the skin following exposure to ultraviolet radiation.

[0042] In addition, the alkoxyalkylamide compounds are believed to have skin lightening properties due to the ascorbate moieties. The ascorbate moiety also possesses antioxidant properties that prevent the adverse effects of oxidation; it also boosts collagen production resulting in the reduction of fine lines and/or wrinkles.

[0043] It is believed that the alkoxyalkylamide compounds of the present invention are also advantageous due to the ease of manufacture and handling thereof. The compounds have a neutral pH which enables the use of a neutral pH carrier. Some conventional moisturizers, e.g., aliphatic hydroxyacids, are acidic and therefore must be neutralized or incorporated into a basic carrier to be effective and non-irritating to the human skin.

[0044] It is also believed that the alkoxyalkylamide compounds of the present invention also do not rapidly degrade, either in storage or formulation, resulting in a loss of activity and/or a change in color. The alkoxyalkylamide compounds would be stable, have a long shelf-life, and their ascorbate moieties are readily released upon application to improve skin condition and appearance. The alkoxyalkylamide compounds of the present invention would also have an increased penetration and permeability; therefore, they are more significantly absorbed by the skin to improve the condition and appearance thereof.

[0045] The present invention is also directed to a cosmetic composition comprising up to 75% by weight of a compound of formula (I), (II), or (III), or a combination thereof. The value of n in compounds of formula (I), (II), or (III) in such cosmetic compositions can be a whole number of 1 to 10, and the value of m can be a whole number of 1 to 10. In one embodiment, the value of n is a whole number of 1 to 4. In another embodiment, the value of m is a whole number of 1 to 4. In another embodiment, the value of n is 3. In yet another embodiment, the value of m is 1.

[0046] The present invention is also directed to a cosmetic composition comprising up to 75% by weight of a compound of formula (IV), (V), or (VI), or a combination thereof.

[0047] The cosmetic compositions of the present invention which include the compounds of the present invention are useful for a variety of cosmetic purposes due to the properties mentioned above with regard to the compounds.

[0048] In addition to a compound of the present invention, the cosmetic composition of the present invention includes a carrier. The carrier for use in formulating the cosmetic composition may comprise one or more compounds which is selected based on the particular intended use of the composition. The carrier may be inorganic or organic in nature; it must be non-toxic and non- irritating. The carrier must also be compatible with the alkoxyalkylamide compound.

[0049] Based on the intended use, the compositions may be care, treatment, cleansing, and/or protective products for facial or body skin; antiwrinkle or anti- aging compositions; skin firming compositions; skin lightening compositions; compositions for irritated skin; sunscreen compositions, artificial tanning (self- tanning) compositions or after-sun care compositions; hair care and/or scalp care compositions; shaving preparation compositions; depilatory compositions; or make-up products for the skin of the face or body.

[0050] The cosmetic compositions of the present invention may also include one or more optional ingredient. Examples of the optional ingredients include but not limited to lubricants, preservatives, perfumes, and colorants. The optional ingredients should be chemically inert with respect to each other, and with respect to the alkoxyalkylamide compound.

[0051] The cosmetic compositions of the present invention may be prepared and used in the form of a lotion, cream, ointment, stick, soap, or other forms commonly employed in the art of cosmetic and skin care formulation. The compositions may be in an emulsion form.

[0052] For example, for use in treating dry skin, the composition of the present invention may be prepared employing an effective amount (up to about 75 wt%) of an alkoxyalkylamide compound of the present invention in a cosmetically acceptable carrier, e.g., a hydrophilic ointment or petrolatum. In one

embodiment, an amount of about 1 to about 20 wt of the alkoxyalkylamide compound is employed. In another embodiment, an amount of about 5 to about 15 wt of the alkoxyalkylamide compound is employed. It should be understood that smaller amounts of the alkoxyalkylamide compound may be used in the cosmetic composition, for example, when the compound is used together with one or more other skin moisturizer or softener, or when the compound is used in cosmetic compositions that are designed primarily for other types of cosmetic functions.

[0053] When an aqueous carrier is used, the cosmetic composition may comprise about 30 to about 90 wt of water. In one embodiment, the composition comprises about 55 to about 65 wt of distilled water. In another embodiment, the composition comprises about 10 to about 40 wt of water, for example, about 15 to about 30 weight wt of water. It should be understood however, that the water in the composition can be totally or partly eliminated by the use of nonaqueous or partially aqueous carriers. [0054] A general example of an aqueous composition according to the present invention is as follows:

about 0.1 to about 7 wt emulsifying agent(s),

about 0.1 to about 15 wt emollient(s),

about 0.1 to about 15 wt compound(s) of the present invention, about 0.1 to about 5 wt lubricant(s),

about 0.1 to about 1 wt preservative(s),

about 0.1 to about 1 wt perfume(s),

about 0.01 to about 30 wt colorant(s), and

water to make up to 100 wt .

[0055] Lists of carriers and optional ingredients, which are well known in the art, are disclosed, for example, in "Cosmetics: Science and Technology," edited by M. S. Balsam and E. Sagarin, 2nd Edition, 1972, Wiley Pub. Co.; "The

Chemistry and Manufacture of Cosmetics" by M. G. DeNavasse; and "Harry's Cosmeticology," J. B. Wilkinson et al., 7th Edition, 1982, Chem. Pub. Co.; the disclosures of each of the above being incorporated herein by reference.

[0056] The alkoxyalkylamide compounds of the present invention may be topically applied in uncompounded form to the areas of the skin to be treated therewith. Whether used as is, or in a compounded or compositional form, the alkoxyalkylamide compounds of the present invention may be topically applied one or more time per day to the area of the skin to be treated for a period of about 7 to 30 days in order to achieve the desired effect. For example, the

alkoxyalkylamide compounds of the present invention are applied about 1 to 2 times per day.

[0057] A makeup composition, for example, may incorporate an

alkoxyalkylamide compound of the present invention in a small amount, generally about 0.01 to about 5 wt%, for example, about 0.02 to about 0.1 wt of the composition. In addition, the makeup composition may comprise about 1 to about 40 wt%, for example, about 10 to about 20 wt%, of a coloring agent in a suitable carrier. Suitable coloring agents include inorganic and organic pigments which are usable in cosmetic formulations. Examples of these pigments include carmine, bismuth oxychloride, zinc oxide, ferric oxide, ferrous oxide, kaolin, ultramarine violet, ultramarine blue, chromium oxide, chromium hydroxide, silica, manganese violet, talc, mica, and titanium oxide. The examples also include lakes of organic colorants such as FD&C Red No. 7 calcium lake, FD&C Yellow No. 5 aluminum lake, FD&C Red No. 9 barium lake, and FD&C Red No. 30.

[0058] As used herein, "about" or "approximately" generally means within 20 percent, preferably within 10 percent, and more preferably within 5 percent of a given value or range.

[0059] Various tests may be carried out to compare formulations containing the alkoxyalkylamide compounds of the present invention with formulations without the alkoxyalkylamide compounds to show the advantageous properties of the alkoxyalkylamide compounds. Examples of tests are provided in Table 1 below:

Table 1

[0060] Examples set forth below show the use of the alkoxyalkylamide compounds of the present invention in various types of the compositions. The following examples are merely illustrative of the scope of the present invention and are not intended as a limitation upon the scope thereof.

EXAMPLES

EXAMPLE 1

[0061] A moisturizing cream formulation may be prepared using an

alkoxyalkylamide compound of the present invention. The formulation, in wt%, is shown in Table 2:

Table 2

Component Weight %

Water 70.36

Butylene Glycol 1.00

Methyl p-Hydroxybenzoate 0.30 Mineral Oil 1.50

C_12-15 Alcohol Benzoate 1.50

Glyceryl Monostearate 2.30

Polawax* 4.08

Stearyl Alcohol 1.50

Polyoxyethylene 21 Stearyl Ether 0.75

Silicone Oil 0.21

Stearyl Stearoyl Stearate 1.00

Propyl p-Hydroxybenzoate 0.10

Bisabolol 0.20

lmidazolidinyl Urea 0.20

Alkoxyalkylamide compound of formula (IV) 15.00

TOTAL 100.00

*Polawax (Croda, Inc.) is a preparation of higher fatty alcohols and ethylene oxide reaction products.

[0062] The cream is an emulsion that is prepared from four subcombinations, or phases, of the components listed above.

[0063] Phase A is made of 52.36% water, 1.00% propylene glycol and 0.30% methyl-p-hydroxy benzoate. Phase D is made of 15.00% water and 15.00% of the alkoxyalkylamide compound. Phase B contains all the remaining

components except the imidazolidinyl urea.

[0064] The components of Phase A are first mixed together with heating at 80°C, and the components of Phase B are also mixed together at 80°C. Subsequently, Phase B is added to Phase A, and heating (at 80°C) and mixing is continued for about 10 minutes, and then the heating is stopped.

[0065] Phase C is formed by dissolving the imidazolidinyl urea in the water and heating to 50° C. Phase C is then added to the Phase A/B admixture. Phase D is made by dissolving alkoxyalkylamide compound in water and heating to 45° C, then Phase D is added to the Phase A/B/C admixture. The resulting product is then cooled to 35° C with mixing and packaged.

EXAMPLE 2

[0066] The alkoxyalkylamide compounds of the present invention may be incorporated in cosmetic compositions containing sunscreening agents. A formulation of such a composition, in wt%, is shown in Table 3:

Table 3

[0067] The use of the alkoxyalkylamide compound of formula (IV) in a sunscreen composition above is believed to possess improved dry skin treating properties compared to a sunscreen composition without the compound therein.

EXAMPLE 3

[0068] The alkoxyalkylamide compounds of the present invention may be incorporated in a water in oil emulsion cosmetic compositions. A formulation of such a composition, in wt%, is shown in Table 4:

Table 4

Component Weight %

Water 52.058

Methyl Paraben 0.200

Ethyl Paraben 0.150

Disodium Salt of Ethylene Diamine Tetraacetic Acid 0.240

Butylated Hydroxy Toluene 0.150

Butylene Glycol 4.000

Triethanolamine 0.092

Cyclomethicone 10.000

Carbopol 1342 (Carbomer 1342) 0.110

Dimethicone 50 cs 10.000

Dimethicone 1000 cs 7.500

Isocetyl Linoleoyl Oxystearate 5.000

*Abil® WS08 (Goldschmidt AG) is a combination of Cetyl Dimethicone Copolyol Cetyl Dimethicone, Polyglycery-1 Oleate and Hexyl Laurate.

[0069] The alkoxyalkylamide compound of formula (IV) is believed to be physically, chemically and functionally compatible with the other components of the Example 3 formulation. The use of the alkoxyalkylamide compound in the Example 3 formulation is believed to provide noticeably improved dry skin treating properties compared to a formulation without such compound therein.

EXAMPLE 4

[0070] This example illustrates a possible cosmetic composition of the present invention containing the alkoxyalkylamide compound of formula (IV) with skin moisturizing properties, the formulation of which is shown in Table 5:

Table 5

Component Weight %

Alkoxyalkylamide compound of formula (IV) 0.1

Water 55.67

Carbomer 8

Octyl methoxycinnamate 7

Butylene glycol 5

Propylene glycol dicaprylate/dicaprate 4

Stearic acid 3

Benzophenone-3 3

Isostearyl neopentanoate 2.5

Glycerin 2

Triethanolamine 1.85

Glyceryl stearate 1.5

Polysorbate 60 1.2

Petrolatum 1

Coco-caprylate/caprate 1

Dimethicone 0.5

Sorbitan stearate 0.5

Squalane 0.5

Sodium hyaluronate, chitin 0.5

Imidazolidinyl urea 0.3

Cetyl alcohol 0.25

Methylparaben 0.15 Tocopheryl acetate 0.1

Sodium PCA (2-pyrrolidone-5-carboxylic acid) 0.1

Evening primrose oil 0.1

Propylparaben 0.05

Bisabolol 0.05

Trisodium EDTA 0.05

Fragrance 0.03

TOTAL 100.00

EXAMPLES 5 TO 12

[0071] Compositions for firming, plumping, or tightening of the skin may incorporate advantageously the alkoxyalkylamide compounds of the present invention. Such compositions can comprise also a skin-firming agent, for example, xanthan gum, carboxy methyl cellulose or related cellulosic material, and fibronectin or other proteinaceous material, and a compatible carrier. The amount of the skin-firming agent in the composition will be about 0.1 to about 35 wt of the total composition, such as about 2 to about 15 wt of the total composition. The amount of an alkoxyalkylamide compound of the present invention in the composition will be about 0.1 to about 20 wt of the total composition, such as about 1 to about 15 wt of the total composition. Tables 6 and 7 below provide eight exemplary cosmetic compositions having skin-firming properties.

Table 6

Component, weight % Ex. 5 Ex. 6 Ex. 7 Ex. 8 Ex. 9

Imidazolidinyl urea 0.3 0.3 0.3 0.3 0.3

TOTAL 100.0 100.0 100.0 100.0 100.0

Available from Laboratories Serobiologiques as Firmogen LS 3497

Table 7

Fibronectin-containing liposomes

EXAMPLES 13 TO 16

[0072] It is believed that the alkoxyalkylamide compounds of the present invention may be ideal for use in products used for skin tanning type applications where their superior moisturizing properties aid in preventing the drying of the skin caused by exposure to the sun and/or wind. The essential components for a cosmetic composition of the present invention having sunscreening properties include a sunscreening agent, an alkoxyalkylamide compound of the present invention, and a suitable carrier.

[0073] Sunscreening agents suitable for use in the cosmetic composition include but not limited to p-aminobenzoic acid (PABA) and its derivatives such as octyl dimethyl PABA, amyl-p-dimethylaminobenzoate, and glyceryl monop- aminobenzoate; cinnamates such as octyl methoxycinnamate, isobutyl salicylcinnamate, and 2-ethoxyethyl-p-methoxycinnamate; benzophenone and its derivatives such as 2-hydroxy-4-methoxybenzophenone (benzophenone-3) and 2- hydroxy-4-methoxybenzophenone-5-sulfonic acid (benzophenone-4); salicylates such as benzyl salicylate, homomenthyl salicylate, dipropylene glycol salicylate, and 2-ethylhexyl salicylate; ricinoleate and derivatives such as propylene glycol ricinoleate; coumarin (2H-l-benzopyran-2-one); tannic acid and digalloyl trioleate.

[0074] The concentration of the sunscreening agent depends on its efficacy as a sunscreen, but is generally about 0.25 to about 33 wt of the total weight of the composition, such as about 1 to about 15 wt of the total weight of the composition. The amount of an alkoxyalkylamide compound of the present invention in the composition is about 0.01 to about 10 wt of the total weight of the composition, such as about 0.1 to about 5 wt of the total weight of the composition.

[0075] Table 8 below provides four exemplary cosmetic compositions having sunscreening properties. The term in parentheses is the approximate Sun

Protection Factor (SPF) for each composition. Examples 13 to 15 are aqueous- based compositions, whereas Example 16 is a non-aqueous composition.

Table 8

EXAMPLE 17

[0076] The alkoxyalkylamide compounds of the present invention may also be used advantageously in self-tanning compositions. Such compositions contain tanning agents capable of darkening the skin without exposure to ultraviolet radiation. The most commonly used tanning agent is dihydroxyacetone, the amount of which in the composition is generally about 1 to about 12 wt% of the total composition, such as about 2 to about 7 wt of the total composition. The amount of an alkoxyalkylamide of the present invention in the composition is about 0.01 to about 10 wt of the total composition, for example, about 0.1 to about 5 wt of the total composition. An example of a formulation for a cosmetic composition for use in self-tanning is shown in Table 9:

Table 9

EXAMPLE 18

[0077] The alkoxyalkylamide compounds of the present invention may also be used advantageously in compositions for treating the skin before or after exposure to tanning radiation. Such compositions contain at least one moisturizer, and do not require sunscreens or self-tanning agents. Optional ingredients include antioxidants such as tocopheryl acetate (vitamin E), healing agents such as allantoin, protein extracts and amino acid preparations. The amount of an alkoxyalkylamide of the present invention in the composition is about 0.01 to about 10 wt of the total composition, such as about 0.1 to about 5 wt of the total composition. An example of a formulation for a cosmetic composition for use before or after exposure to tanning radiation is shown in Table 10: Table 10

EXAMPLES 19 TO 21

[0078] The alkoxyalkylamide compounds of the present invention may also be used advantageously in compositions for skin cleansing to reduce the drying out of the skin by washing. Essential components of such compositions include also a detergent, or cleansing agent, such as cocamidopropyl betaine, sodium lauryl (and laureth) sulfate and sucrose cocoate, and a compatible carrier. The amount of the cleansing agent in the composition is generally about 1 to about 20 wt of the total composition, such as about 2 to about 11 wt of the total composition. The amount of an alkoxyalkylamide of the present invention in the composition is about 0.1 to about 10 wt of the total composition, such as about 0.5 to about 5 wt% of the total composition. Other desired properties in the composition can be achieved by incorporating different suitable components; in addition, the cleanser may be formulated for different types of skin.

[0079] Table 11 below provides three exemplary cosmetic compositions for skin cleansing. Example 19 is for normal skin, Example 20 for dry skin, and Example 21 for oily skin.

Table 11

EXAMPLE 22

[0080] The alkoxyalkylamide compounds of the present invention may be incorporated into compositions containing proteinaceous material to be applied to the skin. Examples of such proteinaceous material include protein and protein concentrates of such proteins such as collagen, fibronectin, elastin, marine protein, and animal protein. The phrase "proteinaceous material," as used herein, includes also partially and fully hydrolyzed forms thereof, for example, polypeptide fragments and substituent amino acids. The amount of the proteinaceous material in the composition is generally about 0.1 to about 90 wt% of the total composition, such as about 1 to about 15 wt% of the total composition. The amount of an alkoxyalkylamide compound of the present invention in the composition is about 0.01 to about 10 wt of the total composition, such as about 0.1 to about 3 wt of the total composition. An example of a formulation for a cosmetic composition, which is a collagen concentrate, is shown in Table 12:

Table 12

EXAMPLE 23

[0081] The alkoxyalkylamide compounds of the present invention may also be used advantageously in compositions for nail strengthening. An example of a water-based formulation for a nail strengthening composition is shown in Table 13:

Table 13

Components Weight %

Water 59.77

Citric acid 0.05

Glycerin 5.00

Magnesium ascorbyl phosphate 0.05

EDTA 0.05

Butylene glycol 5.00

Ethyl paraben 0.20

Methyl paraben 0.30

Xanthan gum 0.25 Components Weight %

Magnesium aluminum silicate 0.70

Folic acid 0.01

Steareth-20 0.20

Steareth-2 0 0.20

Cetyl alcohol 0.65

Trisiloxane, dimethicone 9.60

Glyceryl stearate 0.25

Propylene glycol dicaprylate/dicaprate 4.00

Stearyl alcohol 0.55

Tocopherol 0.25

Dimethicone 2.90

Urea 0.30

Sodium hyaluronate/glycosaminoglycans 0.10

Alkoxyalkylamide compound of formula (IV) 5.00

Thioctic acid 1.50

Pantetheine 2.00

Linoleamidopropyl-PG dimonium chloride 1.00

Pyridoxine 0.10

Biotin 0.01

Spermine 0.01

TOTAL 100.00

EXAMPLE 24

[0082] An example of a solvent-based formulation for a nail strengthening enamel composition is shown in Table 14:

Table 14

Components Weight %

Nitrocellulose 17.70

Butyl acetate 27.20

Ethyl acetate 27.00

Isopropyl alcohol 8.00

Glyceryl tribenzoate 13.10

Alkoxyalkylamide compound of formula (IV) 1.00

Linoleic acid 3.80

Phytic acid (10% solution in ethyl alcohol) 0.10

Thiooctic acid 0.10

Stearalkonium bentonite 1.00

2,5 dibutyl pheny 3,5 di t-butyl-4-hydroxy benzoate 1.00

TOTAL 100.00 EXAMPLE 25

[0083] The alkoxyalkylamide compounds of the present invention may also be used advantageously in lipstick compositions. An example of a formulation for a lipstick composition is shown in Table 15:

Table 15

EXAMPLE 26

[0084] The alkoxyalkylamide compounds of the present invention may also be used advantageously in makeup compositions. An example of a formulation for a makeup composition is shown in Table 16:

Table 16

Group No. Component Weight %

1 Dimethicone/dimethicone copolyol 20.85

1 Sorbitan sesquioleate 0.05

1 Propyl paraben 0.10

1 Titanium dioxide/methicone 8.00

1 Red iron oxide/methicone 0.47

1 Yellow iron oxide/methicone 1.16

1 Black iron oxide/methicone 0.18

1 Mica/dimethicone 0.98

2 Nylon 12/lecithin 2.00 Group No. Component Weight %

2 Boron nitride 4.00

3 Dimethicone 2.50

3 Dow Corning 2-0747 14.00

3 Tribehenin 2.00

4 Glyceryl rosinate/C9-l l isoparaffin 5.00

5 Water 29.31

6 Methyl paraben 0.20

6 Trisodium EDTA 0.20

6 Butylene glycol 4.50

6 Alkoxyalkylamide compound of formula (IV) 1.50

7 SD alcohol 40-B 3.00

TOTAL 100.00

[0085] Group 1 components are milled in the colloid mill, one after another until no undispersed white or color is present. Subsequently, group 2 components are milled until dispersed. In a main beaker, groups 1 and 2 are charged and heated to 55-60 °C. Group 3 components are then added. After all of the tribehenin is melted, group 4 components are added. For the water phase, in a side beaker group 5 components and the pre-mix of group 6 components are heated to 50- 55 °C. Right before emulsification, group 7 components are added to the water phase. The water phase and the oil phase are then emulsified using a

homogenizer for 15 minutes. The mixture is cooled using a paddle mixer.

EXAMPLE 27

[0086] The alkoxyalkylamide compounds of the present invention may also be used advantageously in compositions for hair conditioning. An example of a formulation for a hair conditioning composition is shown in Table 17:

Table 17

Component Weight %

Water 90.90

Hydroxyethylcellulo se 0.70

Methyl paraben 0.10

Methylichloroisothiazolinone, methylisothiazoline 0.04

Stearalkonium chloride 3.00

Cetyl alcohol 1.50

Cetearyl alcohol, ceteareth-20 2.50

Hydrolyzed wheat protein 0.02

Panthenol 0.01 Component Weight %

Alkoxyalkylamide compound of formula (IV) 0.20

Amodimethicone, cetrimonium chloride, trideceth-12 0.20

Citric acid 0.10

Perfume 0.50

Color 0.23

TOTAL 100.00

[0087] The entire contents of all documents cited throughout this application are hereby incorporated by reference herein.

Claims

WHAT IS CLAIMED IS:

1. A compound of formula (I):

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10.

A compound of formula (II):

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10.

3. A compound of formula (III):

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10.

4. The compound of any one of claims 1 to 3, wherein n is a whole number of 1 to 4.

5. The compound of any one of claims 1 to 3, wherein m is a whole number of 1 to 4.

6. The compound of claim 4, wherein n is 3.

7. The compound of claim 5, wherein m is 1.

8. A compound of formula (IV):

A compound of formula (V):

A compound of formula (VI):

11. A method of making a compound of formula (I) (C_mH_2m+1)-0-(C_nH_2n)-H N

.•••(I)

comprising reacting an alkoxyalkylamine of formula (VII)

H₂N-(C_nH2n)-0-(C_mH_2m+i ) (VII)

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10,

with ascorbic acid.

12. A method of making a compound of formula (II)

comprising reacting an alkoxyalkylamine of formula (VII)

H₂N-(C_nH2n)-0-(C_mH_2m+i ) (VII)

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10,

with ascorbic acid.

13. The method of claim 11 or 12, wherein n is a whole number of 1 to 4.

14. The method of claim 11 or 12, wherein m is a whole number of 1 to 4.

15. The method of claim 13, wherein n is 3.

16. The method of claim 14, wherein m is 1.

17. A method of making a compound of formula (IV)

comprising reacting an alkoxyalkylamine of formula (VIII)

H₂N-(CH₂)₃-0-CH₃ (VIII)

with ascorbic acid.

A method of making a compound of formula (V)

OH OH

H₃CO-(CH₂)₃-HN Z _/CH₂OH

O OH OH .... (V) comprising reacting an alkoxyalkylamine of formula (VIII)

H₂N-(CH₂)₃-0-CH₃ (VIII)

with ascorbic acid.

A method of making a compound of formula (I)

or (III) (C_mH_2m+1 )-0-(C_nH_2n)-HN

·· (HI)

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10,

comprising the steps of:

protecting the hydroxyl at either C-2 or C-3, and the hydroxyls at C-4, C-5, and C-6 of a compound of Formula (IX)

activating the unprotected hydroxyl at either C-2 or C-3;

reacting the activated, protected compound with an alkoxyalkylamine of formula (VII)

H₂N-(C_nH2n)-0-(C_mH_2m+i ) (VII)

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10;

deprotecting the protected hydroxyl at either C-2 or C-3 and the protected hydroxyls at C-l and C-4 to generate an intermediate;

cyclizing the intermediate;

oxidizing the deprotected hydroxyl at either C-2 or C-3; and

deprotecting the protected hydroxyls at C-5 and C-6.

20. The method of claim 19, wherein n is a whole number of 1 to 4.

The method of claim 19, wherein m is a whole number of 1 to 4.

The method of claim 20, wherein

23. The method of claim 21, wherein m is 1.

A method of making a compound of formula (IV)

or (VI)

comprising the steps of:

protecting the hydroxyl at either C-2 or C-3, and the hydroxyls at C-4, C-5, and C-6 of a compound of Formula (IX)

activating the unprotected hydroxyl at either C-2 or C-3;

reacting the activated, protected compound with an alkoxyalkylamine of formula (VIII)

H₂N-(CH₂)₃-0-CH₃ (VIII);

deprotecting the protected hydroxyl at either C-2 or C-3 and the protected hydroxyls at C-l and C-4 to generate an intermediate;

cyclizing the intermediate;

oxidizing the deprotected hydroxyl at either C-2 or C-3; and

deprotecting the protected hydroxyls at C-5 and C-6.

25. The method of claim 19 or 24, wherein the activating step comprises of forming a carbonate or a sulfonate.

26. The method of claim 25, wherein the step of forming a carbonate is performed by a phosgene or a carbonyldiimidazole (CDI).

A cosmetic composition comprising up to 75% by weight of a compound of

wherein n is a whole number of 1 to 10, and wherein m is a whole number of 1 to 10.

28. A cosmetic composition comprising up to 75% by weight of a compound of formula (II):

(C_mH_2m+1)-0-(C_nH_2n)-H

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10.

29. A cosmetic composition comprising up to 75% by weight of a compound of formula (III):

wherein n is a whole number of 1 to 10, and

wherein m is a whole number of 1 to 10.

30. The cosmetic composition of any one of claims 27 to 29, wherein n is a whole number of 1 to 4.

31. The cosmetic composition of any one of claims 27 to 29, wherein m is a whole number of 1 to 4.

The cosmetic composition of claim 30, wherein

33. The cosmetic composition of claim 31, wherein m is 1.

34. A cosmetic composition comprising up to 75% by weight of a compound of formula (IV)

35. A cosmetic composition comprising up to 75% by weight of a compound of formula (V)

36. A cosmetic composition comprising up to 75% by weight of a compound of formula (VI)

CH₂OH

CHOH

H₃CO-(CH₂)₃-HN