AU745987B2 - A cosmetic composition and a method for reducing the ageing processes of skin - Google Patents
A cosmetic composition and a method for reducing the ageing processes of skin Download PDFInfo
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- AU745987B2 AU745987B2 AU61803/99A AU6180399A AU745987B2 AU 745987 B2 AU745987 B2 AU 745987B2 AU 61803/99 A AU61803/99 A AU 61803/99A AU 6180399 A AU6180399 A AU 6180399A AU 745987 B2 AU745987 B2 AU 745987B2
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Description
r"UU/l I I nIrtI Regulation 3.2(2) p I
AUSTRALIA
Patents Act 1990
ORIGINAL
COMPLETE SPECIFICATION *5
S
STANDARD PATENT Application Number: Lodged: S P
**SS.
Invention Title: A COSMETIC COMPOSITION AND A METHOD FOR REDUCING THE AGING PROCESSES OF SKIN The following statement is a full description of this invention, including the best method of performing it known to us A cosmetic composition and a method for reducing the ageing processes of skin The invention refers to a cosmetic composition and a method for reducing the ageing processes of skin and/or treating the pathological lesions of skin.
More specifically the invention refers to a cosmetic composition comprising a hydroximic acid derivative of the formula R YR SR C CH- CH-CH-,N I B R wherein R represents a hydrogen atom or a C 1 .5 alkyl group, 2 stands for a hydrogen atom, a C 1 s 5 alkyl group, a C 5 -7 cycloalkyl group or a phenyl group optionally substituted by a hydroxy or a phenyl group, or R and R" together with the nitrogen atom they are attached to form a 5 to 8 membered ring optionally containing one or more further nitrogen or oxygen atom(s) and said ring can be condensed with a benzene ring,
R
3 means a hydrogen atom, a phenyl group, a naphthyl group or a pyridyl group wherein said groups can be substituted by one or more halo atom(s) or CI.4 alkoxy group(s), Y is a hydroxy group, X stands for an amino group, -1 R forms with B a chemical bond, A is a group of the formula
R
4
R
I I -(CH)m -(CH)n b wherein
R
4 represents a hydrogen atom,
R
5 stands for a hydrogen atom, m has a value of 0, 1 or 2, n has a value of 0, 1 or 2, or a physiologically acceptable acid addition salt thereof as the active ingredient.
The human skin is a natural target of light radiation having several known pleasant and unpleasant effects such as sunburn and carcinogenesis. Due to the ultraviolet radiation free radicals (for example hydroxy radicals or nascent oxygen) form in the skin. Such free radicals can injure the DNA and contribute to the ageing of the skin.
A well-known theory of the ageing process of skin is based on the deteriorating effect of free radicals. In addition to the effect of ultraviolet radiation, free radicals may also form in biochemical processes. Thus, due to e.g. inflammation, hypoxia or reactive hyperaemia, free radicals of oxygen origin such as superoxide anion, perhydroxy or hydroxy radical, hydrogen peroxide etc. may form.
Free radicals having powerful oxidizing effect can injure the membrane by oxidizing the unsaturated fatty acid components of the membrane (peroxidization of lipid) on the one hand, and reactive aldehydes are formed during the oxidization on the other hand. In the injury of membrane, the increased intake of calcium leads to cell death, and pathological processes are started due to the presence of the reactive aldehydes: injury of DNA, mutation in both the cell nucleus and mitochondrium; change in the properties of the interstitial proteins (i.e.
elastin) owing to formation of crosslinks.
c It is known that the elastic structures of collagen proteins and elastin contain a lot of water. It is characteristic of the interstitial proteins that they are rich in lysine. The reactive aldehydes such as malondialdehyde give condensation reaction with the side chains containing amino groups to yield crosslinks. Thus, the originally elastic structure becomes rigid and hydrophobic. During the above process, at first lipofuscin ceroids, then age pigments are formed.
SThe natural protective mechanisms against ultraviolet radiation include bronzing due to the formation of melanin, DNA repair mechanism etc. The deficiency of a protective mechanism such as the damage of the DNA repair and consequently the loss of the correction of the DNA injuries caused by the ultraviolet rays leads to the early ageing of skin or perhaps to a disease called xeroderma pigmentosum that can be accompanied by the development of a malignant tumor. Sunburn spots caused by bronzing in the early childhood are healed leaving an extended scar.
In addition to spinocellular carcinoma, various malignant tumors melanoma, cerato-acanthoma, basalioma, sarcoma) can develop.
Thus, it is of great significance if the ageing processes of skin could be influenced and the pathological lesions could be treated.
The hydroximic acid derivatives of the formula I are known.
HU-P No. 177 578 and its equivalent US-P No. 4,308,399 describe hydroximic acid derivatives within the compounds of the formula I suitable for the treatment of diabetic angiopathy.
HU-P No. 207 9,88 and its equivalent EP No. 417 210 also describe hydroximic acid halides having a selective beta-blocking effect, thus, being suitable for the treatment of diabetic angiopathy.
HU-P Application No. 2385/92 published under No. T/66350 describes further hydroximic acid derivatives. These known compounds can be used in the treatment of vascular deformations, mainly in the therapy of diabetes mellitus.
The aim of the invention is to provide a composition suitable for reducing the ageing processes of skin and/or treating the pathological lesions of skin.
It was found that the above aim is fulfilled by a composition comprising a hydroximic acid derivative of the formula I or a physiologically acceptable acid addition salt thereof as the active ingredient.
Under the pathological lesions of skin for which the composition of the invention is suitable, especially the followings are meant: dry skin; actinic keratosis, aktinic prurigo (Lopez-Gonzalez's disease); polymorphic light exanthema; toxic photopathy; photo-allergy; purpura senilis; solar atrophy of skin; puberal strias (stria migrans); elastoma diffusum (old skin); X-ray dermatitis; gouty polychondritis; decubitus (bedsore).
In the description and Claims, under the term "composition" a cosmetic composition is meant which is suitable in the first place for' local treatment, and is applied to the skin surface in a conventional manner.
In the description and Claims, under the term "comprises" and its grammatical variations this term does not preclude the presence of additional features, steps, integers or components.
The composition of the invention comprises a hydroximic acid derivative of the formula I or a physiologally acceptable acid addition salt thereof as the active ingredient in admixture with one or more conventional carrier(s) of cosmetic compositions.
In the specification and Claims a Ct-s alkyl group is, for example, a methyl, ethyl, n-propyl, isopropyl, n-butyl or n-pentyl group, preferably a methyl or an ethyl group.
A C5.7 cycloalkyl group is cyclopentyl, cyclohexyl or cycloheptyl group, preferably a cyclopentyl or a cyclohexyl group.
A 5 to 8 membered ring containing one or more heteroatom(s) can be, for example, a pyrrole, pyrazole, imidazole, oxazole, pyridine, pyridazine, pyrimidine, piperazine, morpholine, indole, quinoline etc. ring.
A halo atom is, for example, a fluoro, chloro, bromo or iodo atom, preferalby a chloro or a bromo atom.
The physiologically acceptable acid addition salts of the compounds of the formula I are the acid addition salts formed with physiologically acceptable inorganic acids such as hydrochloric acid, sulfuric acid etc. or with physiologically acceptable organic acids such as acetic acid, fumaric acid, lactic acid etc.
A preferred subgroup of the compounds of the formula I consists of the hydroximic acid derivatives of the formula
R
4 R
R
3 (CH)m -C X R' N -CH, CH-CH-N II I R- Y R wherein R 1
R
2
R
3
R
4
R
5 m and n are as stated in relation to formula I, X represents an amino group, Y means a hydroxy group.
Especially preferred compounds of the formula II are those wherein R' and R 2 together with the nitrogen atom they are attached o* to form a piperidino group, R 3 stands for a pyridyl group, m and n have a value of 0, X is as defined above. Of these compounds, preferred species are as follows: O-(3-piperidino-2-hydroxy-l-propyl)nicotinic amidoxime (Compound The compounds of the formula I can be prepared by the processes known from HU-P No. 177 578.
The composition of the invention contains, in general, 0.1 to by mass, suitably,2 to 10 by mass, preferably 4 to 5 by mass of a hydroximic acid derivative of the formula I or a physiologically acceptable acid addition salt thereof as the active ingredient and conventional carrier(s) of the cosmetic compositions.
The compositions of the invention can be conventional cosmetic formulations suitable for the local treatment of the skin surface. Preferred formulations are creams, body emulsions, sunemulsions, skin treatment foams, sprays, skin regenerating ampouls etc.
The compositions of the invention may contain, in addition to the active ingredient the conventional carriers of cosmetic compositions generally in an amount of 70 to 99.9 by mass.
Suitable carriers are, for example, one- or two-basic alcohols having a saturated or an unsaturated carbon chain such as cetyl alcohol, stearyl alcohol, cetyl-stearyl alcohol, oleyl alcohol, lauryl alcohol, ethylene glycol, propylene glycol, glycerol; natural fats and oils such as olive oil, avocado oil, wheat-germ oilo, maize-germ oil, lanolin, cocoa-butter; higher hydrocarbons such as vaseline oil, vaseline; bee-wax; cellulose derivatives; emulgators such as sodium lauryl sulfate, fatty acid or oleic acid esters of sorbitan, fatty acid or oleic acid esters of poly(ethylene glycol)s, sorbitan ethers of fatty alcohols or oleic alcohols, poly(ethylene glycol) ethers of fatty alcohols or oleic alcohols, glycerides of fatty acids; vitamins, herb extracts such as camomile extract; preservatives such as methyl, phydroxy-benzoate, chlorohexidine gluconate; light protecting factors etc.
The compositions of the invention are prepared by blending the ingredients thereof, in a manner known per se. In case of compositions based on a water/oil or oil/water emulsion, in general, the ingredients of the fatty phase and those of the aqueous phase are separately admixed, then the two phases are blended using a fatty phase of elevated temperature, if required. The active ingredient of the formula I is added, preferably in an aqueous solution, to the fatty phase or to the mixture of the other ingredients.
The skin ageing inhibition effect of the compounds of the formula I was examined on guinea-pigs. The skin surface of 8 guinea-pigs was depilated, then, on both sides of the animals 1 cm 2 areas were irradiated by UV-B light of 100 mJ/cm 2 intensity. After the irradiation one side of the animals was covered with the cream of Example 1 comprising 4 by mass of the test compound as the ~active ingredient. The other side of each animal was covered with a mixture of cosmetic carriers comprising no active ingredient a cream corresponding to that of Example 1 was used, however, said cream contained water instead of the active ingredient, too). Thus, •as a matter of fact, an internal control was used in the experiment.
S *l In case of 4 animals the treatment with the cream was performed immediately after the irradiation, then the treatment was repeated daily for a week (group In case of the other 4 animals the skin surface irradiated was treated with the cream of the invention and the control cream, respectively, only 24 hours after the irradiation (group II).
In case of animals of group I a minimal erythema could be observed on the skin surface irradiated and treated with the composition of the invention 24 and 48 hours after the irradiation.
On the skin surface used as control an area without epithelium could be noticed, and this state subsisted during the 7 days of observation. From the 4th day no difference could be detected between the skin surface irradiated and treated with the composition of the invention and the surrounding skin area.
In case of animals of group II, on the treated area as well as on the control area, skin injuries (vesicula, bulla) could be observed, then an area without epithelium developped. On the 7th day after the irradiation the area treated with the composition of the invention was epithelized.
On the basis of the above examination it can be established that the skin surface is protected from the damaging effects of the UV-B light by the composition of the invention and the compound of the formula I, respectively. If the skin surface is treated with the composition of the invention immediately after the irradiation, only a weak injury of the epithelium is experienced, at the most.
Skin injuries developped by UV-B radiation are healed owing to the treatment with the composition of the invention in a S* shorter time than without treatment. The compound of the formula I exerts an epithelizing effect.
S* Thus, a further embodiment of the invention consists of a method for reducing the ageing processes of skin and/or treating the pathological lesions of skin, said method comprising treating the affected skin surface with a cosmetically effective non-toxic amount of a hydroximic acid derivative of the formula I or a physiologically acceptable acid addition salt thereof Suitably, the skin surface is treated with a cosmetic composition comprising 0.1 to 30 by mass of a hydroximic acid derivative of the formula I or a physiologically acceptable acid addition salt thereof Preferably, the skin surface is treated with O-(3-piperidino- 2-hydroxy-l-propyl)nicotinic amidoxime or a physiologically acceptable acid addition salt thereof.
The invention is further elucidated by means of the following Examples.
Example 1 Cream (oil/water) The cream consists of the following ingredients: compound of the formula I 4.0 by mass cetylstearyl alcohol 7.5 by mass stearic acid 9.0 by mass glycerol monostearate 2.0 by mass sodium lauryl sulfate 0.5 by mass methyl p-hydroxybenzoate 0.1 by mass distilled water 76.9 by mass 100.0 by mass The lipophilic ingredients (cetylstearyl) alcohol, stearyc acid and glycerol monostearate) are melted on a water-bath. The sodium lauryl sulfate and methyl p-hydroxy-benzoate are dissolved in about 38 ml of distilled water at 60 to 65 the pH of the solution is adjusted by the addition of diluted aqueous sodium hydroxide solution to a value of 9 to 10, then the aqueous solution is admixed to the mixture of the lipophilic ingredients, and the emulsion obtained is stirred until cold. The active ingredient is dissolved in the remaining water and the solution is admixed to the cooled cream.
Example 2 Cream (water/oil) The cream consists of the following ingredients: compound of the formula I 5.0 by mass cetylstearyl alcohol 10.0 by mass white wax 10.0 by mass neutral oil 35.0 by mass Imwitor(R 780 K (partial glycerides of vegetable fatty acids) 5.0 by mass methyl p-hydroxybenzoate 0.1 by mass distilled water 34.9 by mass 100.0% by mass The ingredients are blended using the method described in Example 1.
Example 3 Cream (water/oil) The cream consists of the following ingredients: compound of the formula I 5.0 by mass cetylstearyl alcohol 1.5 by mass white wax 1.5 by mass lanalcol 2.5 by mass cholesterol 1.0 by mass white vaseline 43.5 by mass sodium tetraborate 2.0 by mass methyl p-hydroxybenzoate 0.1 by mass distilled water 42.9 by mass 100.0 by mass 12 The ingredients are blended using the method described in Example 1.
Example 4 Moisturizing cream for night The cream consisting of the following ingredients is prepared using the method described in Example 1: compound 5.0 by mass cetyl alcohol 5.0 by mass lanolin (anhydrous) 5.0 by mass cocoa-butter 5.0 by mass vaseline 5.0 by mass vaseline oil 5.0 by mass isopropyl miristate 1.0 by mass isopropyl palmitate 1.0 by mass wheat-germ oil 10.0 by mass *oeoo evening primrose oil 5.0 by mass vitamin A 0.03 by mass vitamine E 0.05 by mass Stglycerol 5.0 by mass glycerol 5.0 by mass propylene glycol 5.0 by mass methyl p-hydroxybenzoate 0.2 by mass perfume 0.1 by mass water, demineralized 42.62 by mass 100.00 by mass Example Moisturizing cream for day The cream consisting of the following ingredients is prepared by the method described in Example 1.
compound "B" cetyl alcohol lanolin (anhydrous) vaseline vaseline oil isopropyl miristate isopropyl palmitate borage oil peanut oil vitamin A vitamin E glycerol propylene glycol methyl p-hydroxybenzoate perfume water, demineralized 5.0 by mass 5.0 by mass 5.0 by mass 5.0 by mass 5.0 by mass 1.0 by mass 1.0 by mass 4.0 by mass 11.0 by mass 0.03 by mass 0.05 by mass 5.0 by mass 5.0 by mass 0.2 by mass 0.1 by mass 47.62 by mass 100.00 by mass Example 6 Body milk The body milk consisting of the following ingredients is prepared by the method described in Example 1.
compound 4.0 by mass stearic acid monoglyceride 2.0 by mass cetylstearyl alcohol 2.0 by mass peanut oil 5.0 by mass vaseline oil 3.0 by mass polyoxyethylene cetylstearyl alcohol (degree of polymerization: 20) 2.0 by mass 11 glycerol methyl p-hydroxybenzoate propyl p-hydroxybenzoate butyihydroxytoluene water, demnineralized 4.0 %by mass 0.2 %by mass 0. 1 by mass 0.01 %by mass 77.69 by mass 100. 00 by mass
Claims (9)
1. Use of a composition comprising a hydroximic acid derivative of the formula X Y 3 1 R 2 R3 -A--N-O-CH 2 -CH-CH 2 -N N wherein R 1 represents a hydrogen atom or a C1.5 alkyl group, R 2 stands for a hydrogen atom, a C1.5 alkyl group, a C5.7 cycloalkyl group or a phenyl group optionally substituted by a hydroxy or a phenyl group, or R 1 and R 2 together with the nitrogen atom they are attached to form a 5 to 8 membered ring optionally containing one or more further nitrogen or oxygen atom(s) and said ring can be condensed with a benzene ring, R 3 means a hydrogen atom, a phenyl group, a naphthyl group or a pyridyl group wherein said groups can be substituted by one or more halo atom(s) or C1 alkoxy group(s), Y is a hydroxy group, A is a group of the formula R4 R -(CH)m (CH)m- b wherein R 4 represents a hydrogen atom, R 5 stands for a hydrogen atom, m has a value of 0, 1 or 2, n has a value of 0, 1 or 2, 16 or an acid addition salt thereof in admixture with one or more conventional cosmetic carrier(s) in cosmetic treatment for reducing ageing process of the skin.
2. A use according to Claim 1 comprising a compound of the formula I, wherein R 1 and R 2 together with the nitrogen atom they are attached to form a piperidino group, R 3 A, X and Y are as defined in Claim 1, or an acid addition salt thereof.
3. A use according to Claim 1 or 2 comprising O-(3-piperidino-2-hydroxy- 1 -propyl)nicotinic amidoxime or an acid addition salt thereof.
4. A method of cosmetic treatment of the skin in which the affected skin surface is treated with a cosmetically effective non-toxic amount of a hydroximic acid derivative of the formula I, wherein R 1 R 2 R 3 X, Y and A are as defined in Claim 1, or an acid addition salt thereof.
5. A method of cosmetic treatment according to Claim 4 in which the skin surface is treated with a cosmetic composition comprising 0.1 to 30% by mass of a hydroximic acid derivative of the formula I, wherein R, R 3 X, Y and A are as defined in Claim 1, or an acid addition salt thereof.
6. A method of cosmetic treatment according to either of Claims 4 and 5 in which the hydroximic acid derivative is O-(3-piperidino-2-hydroxy-1- propyl)nicotinic amidoxime or an acid addition salt thereof.
7. Use of a compound of the formula I as defined in Claim 1 for the manufacture of a cosmetic composition for cosmetic treatment for reducing ageing process of the skin. 17
8. Use of a compound of the formula I as claimed in Claim 1, or an acid addition salt thereof for the preparation of a topical composition for the treatment of pathological lesions of the skin.
9. Use of a compound of the formula I as claimed in Claim 1 for the preparation of a topical composition for the treatment of actinic ceratosis. A use according to either of Claims 8 and 9 wherein the compound of formula I is O-(3-piperidino-2-hydroxy-1-propyl)nicotinic amidoxime or an acid addition salt thereof. DATED this 2 6 t h day of September 2001 MEDGENE LIMITED WATERMARK PATENT TRADEMARK ATTORNEYS 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRALIA P1343AU01 LCG/RBP/RES *o•
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU61803/99A AU745987B2 (en) | 1995-12-22 | 1999-11-30 | A cosmetic composition and a method for reducing the ageing processes of skin |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9503728 | 1995-12-22 | ||
| AU61803/99A AU745987B2 (en) | 1995-12-22 | 1999-11-30 | A cosmetic composition and a method for reducing the ageing processes of skin |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU11673/97A Division AU1167397A (en) | 1995-12-22 | 1996-12-20 | A cosmetic composition and a method for reducing the ageing processes of skin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6180399A AU6180399A (en) | 2000-02-17 |
| AU745987B2 true AU745987B2 (en) | 2002-04-11 |
Family
ID=3746784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU61803/99A Ceased AU745987B2 (en) | 1995-12-22 | 1999-11-30 | A cosmetic composition and a method for reducing the ageing processes of skin |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU745987B2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308399A (en) * | 1977-08-30 | 1981-12-29 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | O-(3-Amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same |
| US5147879A (en) * | 1988-10-20 | 1992-09-15 | Biorex Kutato-Fejleszto Kft | O-(3-amino-2-hydroxypropyl)-hydroximic acid halides and process for preparing the same |
-
1999
- 1999-11-30 AU AU61803/99A patent/AU745987B2/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308399A (en) * | 1977-08-30 | 1981-12-29 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | O-(3-Amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same |
| US5147879A (en) * | 1988-10-20 | 1992-09-15 | Biorex Kutato-Fejleszto Kft | O-(3-amino-2-hydroxypropyl)-hydroximic acid halides and process for preparing the same |
| US5328906A (en) * | 1988-10-20 | 1994-07-12 | Biorex Kutato-Fejleszto Kft | 0-(3-amino-2-hydroxypropyl)-hydroximic acid halides and process for preparing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6180399A (en) | 2000-02-17 |
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|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: N-GENE RESEARCH LABORATORIES INC. Free format text: THE FORMER OWNER WAS: MEDGENE LIMITED |
|
| FGA | Letters patent sealed or granted (standard patent) |