JP2012001520A - Composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition for skin conditioning, preferable for cosmetic (including a quasi drug).SOLUTION: The composition containing a compound (1) represented by the general formula (1) and/or a pharmacologically acceptable salt thereof and an antiwrinkle agent (2) is provided (in the formula, A represents a di- or tri-aromatic methyl group selected independently from the group consisting of an allyl group having an unsubstituted or substituted group and/or a heteroaromatic ring having an unsubstituted or substituted group, and B represents a cyclic or non-cyclic and aliphatic or aromatic hydrocarbon group in which a part of binding with A is heteroatom, and a hydrogen atom and a hydrogen atom or a carbon atom may be replaced by heteroatom).

Description

  The present invention relates to a composition suitable for cosmetics (however, including quasi-drugs), foods, and the like. Specifically, 1) a compound represented by the following general formula (1) and / or their pharmacological properties It is related with the composition characterized by containing the salt accept | permitted by 2 and 2) an anti-wrinkle agent.

（１）
[式中、Aは、無置換又は置換基を有するアリ−ル基及び／又は無置換又は置換基を有する複素芳香族環よりなる群からそれぞれ独立に選ばれるジ又はトリ芳香族メチル基を表し、Bは、Aとの結合部位が複素原子である、水素原子、水素原子又は炭素原子が複素原子により置換されていてもよい環状又は非環状の脂肪族又は芳香族炭化水素基を表す。]

(1)
[Wherein, A represents a di- or tri-aromatic methyl group independently selected from the group consisting of an unsubstituted or substituted aryl group and / or an unsubstituted or substituted heteroaromatic ring. , B represents a cyclic or acyclic aliphatic or aromatic hydrocarbon group in which the bonding site to A is a hetero atom, and a hydrogen atom, a hydrogen atom, or a carbon atom may be substituted with a hetero atom. ]

  Skin symptoms such as wrinkles, spots, sagging, etc., which have a significant effect on the appearance of others, are manifested with aging due to genetic factors and accumulation of physical stimuli such as temperature changes and UV exposure over many years. To do. In particular, since wrinkles and sagging are a major factor in judging the youthfulness of appearance by others, various methods have been tried to prevent or improve wrinkles and sagging. As such a method, as a cosmetic method, a method by physical stimulation such as massage treatment, a medical method such as hyaluronic acid injection, and the like are known, but sufficient effects can be obtained. In addition to the fact that there is no such thing, the cost is high and there are problems in the treatment, so it is not necessarily a familiar and effective method for those who expect the effect. On the other hand, although many cosmetics etc. which mix | blended the component which has the prevention or improvement effect of wrinkle formation, and an anti-aging effect | action are marketed, in many cases, the effect may be unclear. For this reason, the technology which strengthens the anti-wrinkle and anti-aging effect which the component which has the prevention or improvement effect with respect to wrinkle formation and the said component has has been desired.

  As described above, the attention to prevention or improvement of skin aging phenomenon, especially, wrinkle formation is very high. For this reason, analysis of the mechanism of action of wrinkle formation and development of anti-wrinkle agents based on information on the mechanism of action that has been elucidated have been actively conducted. The mechanism of wrinkle formation includes cell damage caused by UV exposure and the like, cell apoptosis enhanced by the exposure, collagen caused by enhanced expression of proteases such as matrix metalloprotease (MMP), etc. It has already been reported that the fiber component is hydrolyzed, and further that the bundle of fibers is disrupted by the enhancement of cytokines. Many anti-wrinkle agents have been developed based on the information obtained by analyzing the mechanism of action. Retinoic acid, which is well known as a component having an effect of preventing or improving wrinkle formation (see, for example, Non-Patent Document 1) is approved as a therapeutic drug for wrinkles and acne in the United States, and its effectiveness is also illuminated. However, retinoic acid is not approved in Japan because there are major problems in terms of safety, including irritation to the skin. In addition, as components having preventive or anti-wrinkle action against wrinkle formation other than retinoic acid, anti-wrinkle agents (see, for example, Patent Document 1), collagen production promoters (see, for example, Patent Document 2), hyaluron Acid production promoters (see, for example, Patent Document 3) are known. In addition, for triterpenic acid or its benzyl derivative, the dermal collagen fiber bundle structure is reconstructed against wrinkles caused by the collapse of the dermal collagen fiber bundle caused by light irradiation, and the improvement effect Is known (see, for example, Patent Document 4). However, the above-mentioned anti-wrinkle agent has limitations on formulation due to solubility, in addition to problems related to safety and stability. In addition, since such anti-wrinkle agents may not provide sufficient preventive or ameliorating effects, in addition to the creation of new anti-wrinkle agents, further, ingredients and formulations that enhance the effects of existing anti-wrinkle agents Technology development is desired.

Steric bulky aromatic groups or heteroaromatic groups (particularly diphenylmethyl or triphenylmethyl groups) are widely known as effective protecting groups for hydroxyl groups or amino groups in organic low molecular weight compounds, peptides and nucleic acid synthesis. (For example, see Non-Patent Document 2 and Non-Patent Document 3). Reactions using these protecting groups and intermediate compounds (see, for example, Non-Patent Document 4 and Non-Patent Document 5) have been applied to organic synthesis in a wide range of scales from laboratory to industrial production. In addition, regarding the compound having the above-described sterically bulky substituent in its chemical structure, antitumor activity (see, for example, Non-Patent Document 4), antifungal action (for example, see Patent Document 5), It exhibits biological activities such as antihistamine action (for example, see Non-Patent Document 5), dopamine uptake inhibitory action (for example, see Non-Patent Document 6), calcium antagonism (for example, see Non-Patent Document 7), etc. It has been reported. However, it is not known at all that inclusion of the compound represented by the general formula (1) in the composition together with the anti-wrinkle agent enhances the skin beautifying action, especially the prevention or improvement action against wrinkle formation. It was.

Japanese Patent Application Laid-Open No. 07-041419 Japanese Patent Laid-Open No. 07-285846 JP 2007-051091 A WO / 2007/148474 JP 09-255634 A

Development technology for anti-aging, whitening and moisturizing cosmetics, CMC Publishing, supervised by Masato Suzuki Theodora W. Green, Protective Groups in Organic Synthesis, A Wiley-Interscience Publication .: 1981, P173-176 and P273-274 Nobuo Izumiya, Tetsuo Kato, Toshihiko Aoyagi, Michinori Waki, Basics and Experiments of Peptide Synthesis: Maruzen Co., Ltd., 1985, P38 Naohisa Ogo et. Al., Bioorganic & Medicinal Chemistry, 17 (4), 3921-3924 (2007) Sasse A., et. Al., Bioorganic & Medicinal Chemistry, 8 (5), 1139-1149 (2000) Dutta AK. Et. Al., Bioorganic & Medicinal Chemistry, 11 (17), 2337-2340 (2001) Shanklin JR Jr., et al., J. Med. Chem., 34 (10), 3011-3022 (1991)

The present invention has been made under such circumstances, and is a composition suitable for cosmetics (however, including quasi-drugs), foods, etc., specifically 1) the following general formula (1 And a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent.

In view of such a situation, the inventors have sought for a composition such as an external preparation for skin that is suitable for skin beautification, especially for prevention or improvement of wrinkle formation, and as a result of intensive efforts, 1) the above general A composition comprising the compound represented by formula (1) and / or a pharmacologically acceptable salt thereof and 2) an anti-wrinkle agent has such properties. As a result, the present invention has been completed. That is, the present invention is as follows.
<1> 1) A composition comprising the compound represented by the following general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent.

（１）
[式中、Aは、無置換又は置換基を有するアリ−ル基及び／又は無置換又は置換基を有する複素芳香族環よりなる群からそれぞれ独立に選ばれるジ又はトリ芳香族メチル基を表し、Bは、Aとの結合部位が複素原子である、水素原子、水素原子又は炭素原子が複素原子により置換されていてもよい環状又は非環状の脂肪族又は芳香族炭化水素基を表す。]

(1)
[Wherein, A represents a di- or tri-aromatic methyl group independently selected from the group consisting of an unsubstituted or substituted aryl group and / or an unsubstituted or substituted heteroaromatic ring. , B represents a cyclic or acyclic aliphatic or aromatic hydrocarbon group in which the bonding site to A is a hetero atom, and a hydrogen atom, a hydrogen atom, or a carbon atom may be substituted with a hetero atom. ]

<2> The compound represented by the general formula (1) is a compound represented by the following general formula (2) and / or a pharmacologically acceptable salt thereof, <1 The composition according to>.

（２）
[式中、Aは、無置換又は置換基を有するアリ−ル基よりなる群からそれぞれ独立に選ばれるジ又はトリアリ−ルメチル基を表し、Bは、Aとの結合部位が複素原子である、水素原子、水素原子又は炭素原子が複素原子により置換されていてもよい環状又は非環状の脂肪族又は芳香族炭化水素基を表す。]

(2)
[In the formula, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, and B is a hetero atom at the bonding site with A. It represents a cyclic or acyclic aliphatic or aromatic hydrocarbon group in which a hydrogen atom, a hydrogen atom or a carbon atom may be substituted with a hetero atom. ]

<3> The compound represented by the general formula (2) is a compound represented by the following general formula (3) and / or a pharmacologically acceptable salt thereof, <1 > Or <2>.

（３）
[式中、Aは、無置換又は置換基を有するアリ−ル基よりなる群からそれぞれ独立に選ばれるジ又はトリアリ−ルメチル基を表し、Xは、窒素原子又はNH基を表し、R１は、水素原子、水素原子又は炭素原子が複素原子で置換されていてもよい炭素数３〜８の環状脂肪族炭化水素基を表し、前記環状脂肪族炭化水素基の環は、Ｒ１のもう一方の末端がＸに再び結合して形成される環も包含する。]

(3)
[In the formula, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents a nitrogen atom or NH group, and R1 represents A hydrogen atom, a hydrogen atom, or a C 3-8 cyclic aliphatic hydrocarbon group that may be substituted with a hetero atom, and the ring of the cyclic aliphatic hydrocarbon group is the other end of R 1 Includes a ring formed by re-bonding to X. ]

<4> The compound represented by the general formula (2) is a compound represented by the following general formula (4) and / or a pharmacologically acceptable salt thereof, <1 > Or <2>.

（４）
[式中、Ａは、無置換又は置換基を有するアリ−ル基よりなる群からそれぞれ独立に選ばれるジ又はトリアリ−ルメチル基を表し、Ｘは、酸素原子を表し、Ｒ２は、水素原子、水素原子又は炭素原子が複素原子に置換されていてもよい炭素数１〜８の脂肪族炭化水素を表す。]

(4)
[Wherein, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents an oxygen atom, R2 represents a hydrogen atom, It represents a C1-C8 aliphatic hydrocarbon in which a hydrogen atom or a carbon atom may be substituted with a hetero atom. ]

<5> The compound represented by the general formula (2) is a compound represented by the following general formula (5) and / or a pharmacologically acceptable salt thereof, <1 > Or <2>.

（５）
[式中、Ａは、無置換又は置換基を有するアリ−ル基よりなる群からそれぞれ独立に選ばれるジ又はトリアリ−ルメチル基を表し、Ｘは、窒素原子を表し、Ｒ３及びＲ４は、それぞれ独立に、水素原子、水素原子又は炭素原子が複素原子に置換されていてもよい炭素数１〜８の脂肪族炭化水素を表す。]

(5)
[Wherein, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents a nitrogen atom, and R3 and R4 each represent Independently, the C1-C8 aliphatic hydrocarbon in which the hydrogen atom, the hydrogen atom, or the carbon atom may be substituted by the hetero atom is represented. ]

<6> The compound represented by the general formula (2) is a compound represented by the following general formula (6) and / or a pharmacologically acceptable salt thereof, <1 > Or <2>.

（６）
[式中、Ａは、無置換又は置換基を有するアリ−ル基よりなる群からそれぞれ独立に選ばれるジ又はトリアリ−ルメチル基を表し、Ｘは、窒素原子又はNH基を表し、Ｒ５は、水素原子又は炭素原子が複素原子で置換されていてもよい炭素数３〜８の芳香族炭化水素基を表し、前記芳香族炭化水素基は、Ｘが環内に存在する基も包含する。]

(6)
[Wherein, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents a nitrogen atom or NH group, and R5 represents A hydrogen atom or a C3-C8 aromatic hydrocarbon group in which a carbon atom may be substituted with a hetero atom is represented, and the aromatic hydrocarbon group includes a group in which X is present in the ring. ]

<7> The compounds represented by the general formulas (1) to (6) are 1- (diphenylmethyl) imidazole (compound 1), 1- (triphenylmethyl) imidazole (compound 2), 2 -[(Diphenylmethyl) oxy] ethanol (compound 3), 2-[(triphenylmethyl) oxy] ethanol (compound 4), 2-[(diphenylmethyl) amino] ethanol (compound 5) 2-[(triphenylmethyl) amino] ethanol (compound 6), 2-[(diphenylmethyl) oxy] ethylamine (compound 7), 2-[(triphenylmethyl) oxy] ethylamine (compound 8), 1- (diphenylmethyl) pyrrolidine (compound 9), 1- (triphenylmethyl) pyrrolidine (compound 10), 1- (diphenylmethyl) piperidine (compound 11), 1- (triphenylmethyl) <1> to <6>, comprising 1) or 2 or more types selected from (i) piperidine (compound 12) and / or a pharmacologically acceptable salt thereof. The composition as described.

１−（ジフェニルメチル）イミダゾ−ル（化合物１）

1- (Diphenylmethyl) imidazole (Compound 1)

１−（トリフェニルメチル）イミダゾ−ル（化合物２）、

1- (triphenylmethyl) imidazole (compound 2),

２−[（ジフェニルメチル）オキシ]エタノ−ル（化合物３）

2-[(Diphenylmethyl) oxy] ethanol (Compound 3)

２−[（トリフェニルメチル）オキシ]エタノ−ル（化合物４）

2-[(Triphenylmethyl) oxy] ethanol (compound 4)

２−[（ジフェニルメチル）アミノ]エタノ−ル（化合物５）

2-[(Diphenylmethyl) amino] ethanol (Compound 5)

２−[（トリフェニルメチル）アミノ]エタノ−ル（化合物６）

2-[(Triphenylmethyl) amino] ethanol (Compound 6)

２−[（ジフェニルメチル）オキシ]エチルアミン（化合物７）

2-[(Diphenylmethyl) oxy] ethylamine (Compound 7)

２−[（トリフェニルメチル）オキシ]エチルアミン（化合物８）

2-[(Triphenylmethyl) oxy] ethylamine (Compound 8)

１−（ジフェニルメチル）ピロリジン（化合物９）

1- (Diphenylmethyl) pyrrolidine (Compound 9)

１−（トリフェニルメチル）ピロリジン（化合物１０）

1- (Triphenylmethyl) pyrrolidine (Compound 10)

１−（ジフェニルメチル）ピペリジン（化合物１１）

1- (Diphenylmethyl) piperidine (Compound 11)

１−（トリフェニルメチル）ピペリジン（化合物１２）

1- (Triphenylmethyl) piperidine (Compound 12)

<8> The compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof is 0.001% by mass to 10% by mass with respect to the total amount of the composition. The composition according to any one of <1> to <7>.
<9> The anti-wrinkle agent is vitamin A, a derivative thereof and / or a pharmacologically acceptable salt thereof, triterpenic acid, a derivative thereof and / or a pharmacologically acceptable salt thereof. The composition according to any one of <1> to <8>, which is characterized.
<10> One type wherein the vitamin A or a derivative thereof is selected from retinal, retinal, retinoic acid, tretinoin, isotretinoin, retinoic tocopherol, retinoic palmitate, and retinoic acetate Or it is 2 or more types, The composition as described in any one of <1>-<9> characterized by the above-mentioned.
<11> The triterpenic acid residue of the triterpenic acid or derivative thereof is ursolic acid, betulinic acid or a residue of those acids, any one of <1> to <9> The composition according to item.
<12> The triterpenic acid or derivative thereof is triterpenic acid, triterpenic acid benzyl ester, or triterpenic acid phosphoric ester, <1> to <9>, <11> The composition as described.
<13> The composition according to any one of <1> to <9>, wherein the anti-wrinkle agent is a plant extract having a dermal collagen fiber bundle reconstructing action.
<14> The above-described plant extract having a dermal collagen fiber bundle reconstructing action is one or more selected from the following plant extracts, <1> to <1 9>, The composition as described in <13>.
<Plant extract having dermal collagen fiber bundle restructuring action>
A plant extract obtained from the Myrtaceae spp. Extract, plant extract obtained from honeysuckle elderberry, plant extract obtained from Asteraceae cornflower, plant extract obtained from Lamiaceae rosemary <15> The anti-wrinkle agent is based on the total amount of the composition The composition according to any one of <1> to <14>, which is contained in an amount of 0.00001% by mass to 15% by mass.
<16> The composition according to any one of <1> to <15>, which is a cosmetic (including a quasi-drug).
<17> The composition according to any one of <1> to <16>, wherein the composition is for beautiful skin.
<18> The composition according to any one of <1> to <17>, which is used for prevention or improvement against wrinkle formation.
<19> The composition according to any one of <1> to <17>, which is an external preparation for skin.
<20> 1) A skin external preparation characterized by containing a compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent.
<21> The compound represented by the general formula (1) is a compound represented by the general formula (3) and / or a pharmacologically acceptable salt thereof, <20 > The external preparation for skin described in>.
<22> The compound represented by the general formula (1) is 1- (diphenylmethyl) imidazole (compound 1), 1- (triphenylmethyl) imidazole (compound 2), 2-[(diphenyl). Methyl) oxy] ethanol (compound 3), 2-[(triphenylmethyl) oxy] ethanol (compound 4), 2-[(diphenylmethyl) amino] ethanol (compound 5), 2- [ (Triphenylmethyl) amino] ethanol (Compound 6), 2-[(Diphenylmethyl) oxy] ethylamine (Compound 7), 2-[(Triphenylmethyl) oxy] ethylamine (Compound 8), 1- (Diphenyl) Methyl) pyrrolidine (compound 9), 1- (triphenylmethyl) pyrrolidine (compound 10), 1- (diphenylmethyl) piperidine (compound 11), 1- (triphenylmethyl) pi The external preparation for skin according to <20> or <21>, which is peridine (compound 12) and / or a pharmacologically acceptable salt thereof.
<23> The anti-wrinkle agent is vitamin A, a derivative thereof and / or a pharmacologically acceptable salt thereof, triterpenic acid, a derivative thereof and / or a pharmacologically acceptable salt thereof. The skin external preparation according to any one of <20> to <22>, which is characterized.
<24> One type wherein the vitamin A or a derivative thereof is selected from retinal, retinal, retinoic acid, tretinoin, isotretinoin, tocopherol retinoic acid, retinoic palmitate, and retinoic acetate. Or it is 2 or more types, The skin external preparation as described in any one of <20>-<23> characterized by the above-mentioned.
<25> Any one of <20> to <23>, wherein the triterpenic acid residue of the triterpenic acid or a derivative thereof is ursolic acid, betulinic acid or a residue of those acids. The external preparation for skin according to Item.
<26> The above-mentioned triterpenic acid or a derivative thereof is triterpenic acid, triterpenic acid benzyl ester, or triterpenic acid phosphoric ester, <20> to <23>, any one of <25> The skin external preparation as described.
<27> The skin external preparation according to any one of <20> to <23>, wherein the anti-wrinkle agent is a plant extract having a dermal collagen fiber bundle reconstructing action.
<28> The above-described plant extract having a dermal collagen fiber bundle reconstructing action is one or more selected from the following plant extracts: <20> to <20 23>, <27> The external preparation for skin.
<Plant extract having dermal collagen fiber bundle restructuring action>
A plant extract obtained from the Myrtaceae spp. Extract, plant extract obtained from honeysuckle elderberry, plant extract obtained from Asteraceae cornflower, plant extract obtained from Lamiaceae rosemary <29> oil-in-water emulsifier form <20>-<28> The skin external preparation according to any one of <20> to <28>.
<30> The skin external preparation according to any one of <20> to <29>, further comprising a preferable formulation component.

ADVANTAGE OF THE INVENTION According to this invention, compositions, such as an external preparation for skin, suitable for skin beautification, especially, prevention or improvement with respect to wrinkle formation can be provided.

<Compound represented by the general formula (1) of the present invention>
The composition of the present invention comprises the compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent. The compound represented by the general formula (1) of the present invention and / or a pharmacologically acceptable salt thereof is incorporated into the composition together with an anti-wrinkle agent to be described later, thereby providing an excellent skin beautifying effect, in particular, Demonstrate or prevent wrinkle formation. The skin beautifying action of the composition of the present invention means a preventive or ameliorating action against the skin aging phenomenon related to the aesthetic appearance of the skin that becomes apparent with age, and examples thereof include a preventive or improving action against wrinkle formation. Moreover, the prevention or improvement action with respect to the wrinkle formation means a prevention or improvement action against skin symptoms such as wrinkles and sagging that are formed and manifested in addition to an improvement action that makes the wrinkles already formed inconspicuous. Furthermore, in addition to the prevention or improvement action against wrinkle formation, the component has an action to prevent or improve the overall skin condition due to the prevention or improvement action against skin symptoms caused by pigmentation such as sunburn, spots and dullness. .

  Here, the compound represented by the general formula (1) will be described. In the formula, A is an unsubstituted or substituted aryl group and / or an unsubstituted or substituted heteroaromatic ring. Each represents a di- or triaromatic methyl group independently selected from the group consisting of B and B is a hetero atom at the bonding site to A, even if a hydrogen atom, a hydrogen atom or a carbon atom is substituted by a hetero atom Represents a good cyclic or acyclic aliphatic or aromatic hydrocarbon group. A represents a di- or triaromatic methyl group independently selected from the group consisting of an unsubstituted or substituted aryl group and / or a unsubstituted or substituted heteroaromatic ring; Specific examples of the unsubstituted or substituted aryl group and / or the unsubstituted or substituted heteroaromatic group in FIG. 5 include a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, and a furyl group. , Thienyl group, thiazolyl group, imidazole group, methylphenyl group, ethylphenyl group, propylphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, hydroxyphenyl group, aminophenyl group, N-methylaminophenyl Group, N-ethylaminophenyl group, N-propylaminophenyl group, N, N-dimethylaminophenyl group, N N-diethylaminophenyl group, N, N-dipropylaminophenyl group, fluorophenyl group, difluorophenyl group, trifluoromethylphenyl group, chlorophenyl group, bromophenyl group, methylpyridyl group, ethylpyridyl group, propylpyridyl group, methoxy Pyridyl group, ethoxypyridyl group, propyloxypyridyl group, hydroxypyridyl group, aminopyridyl group, N-methylaminopyridyl group, N-ethylaminopyridyl group, N-propylaminopyridyl group, N, N-dimethylaminopyridyl group, N, N-diethylaminopyridyl group, N, N-dipropylaminopyridyl group, fluoropyridyl group, difluoropyridyl group, trifluoromethylpyridyl group, chloropyridyl group, bromopyridyl group, methylnaphthyl group, ethylnaphthyl group, propylnaphthyl Tyl group, methoxynaphthyl group, ethoxynaphthyl group, propyloxynaphthyl group, hydroxynaphthyl group, aminonaphthyl group, N-methylaminonaphthyl group, N-ethylaminonaphthyl group, N-propylaminonaphthyl group, N, N-dimethyl Aminonaphthyl group, N, N-diethylaminonaphthyl group, N, N-dipropylaminonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, chloronaphthyl group, bromonaphthyl group, imidazole group, methyl Imidazole group, ethyl imidazole group, propyl imidazole group, methoxy imidazole group, ethoxy imidazole group, propyloxy imidazole group, hydroxy imidazole group, amino imidazole group, N- Methylaminoimidazole group, N-ethylaminoimidazole Group, N-propylaminoimidazole group, N, N-dimethylaminoimidazole group, N, N-diethylaminoimidazole group, N, N-dipropylaminoimidazole group, fluoroimidazole group, Difluoroimidazole group, trifluoromethylimidazole group, chloroimidazole group, bromoimidazole group and the like can be suitably exemplified, and more preferably, phenyl group, methylphenyl group, methoxyphenyl group, naphthyl group, A biphenyl group can be suitably exemplified. B represents a cyclic atom or a non-cyclic aliphatic or aromatic hydrocarbon group in which the bonding site to A is a hetero atom, a hydrogen atom, a hydrogen atom or a carbon atom optionally substituted with a hetero atom; For example, a mono- or di-substituted amino group, a hydrogen atom or a carbon having a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms in which a hydroxyl group, an amino group, a hydrogen atom or a carbon atom may be substituted by a hetero atom An alkyloxy group having a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms in which an atom may be substituted by a hetero atom, a hydrogen atom or a carbon atom having 1 to 8 carbon atoms in which the carbon atom may be substituted by a hetero atom, More preferably, a mono- or dialkyl-substituted amino group having an aliphatic hydrocarbon group having 1 to 4 carbon atoms, a hydrogen atom or a carbon atom having 1 to 8 carbon atoms in which the carbon atom may be substituted with a hetero atom, more preferably. Is a mono or di having an alkyloxy group having a C 1-4 aliphatic hydrocarbon group, a hydrogen atom or a C 3-8 aromatic hydrocarbon group in which the carbon atom may be substituted by a hetero atom. A substituted amino group, a hydrogen atom or an alkyloxy group having an aromatic hydrocarbon group having 3 to 8 carbon atoms which may be substituted with a hetero atom. The B is a hydrogen atom or a disubstituted amino group having a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms in which a carbon atom may be substituted with a heteroatom, or a hydrogen atom or a carbon atom is a heteroatom. In the case of representing a disubstituted amino group having an aromatic hydrocarbon group having 3 to 8 carbon atoms which may be substituted by, bonding of A and B to a ring of a cyclic aliphatic hydrocarbon group or an aromatic group The structure including the hetero atom of the site is also included. Among the compounds represented by the general formula (1), more preferable examples include the compounds represented by the general formula (2) and / or pharmacologically acceptable salts thereof. More preferable examples include compounds represented by the general formulas (3) to (6) and / or pharmacologically acceptable salts thereof. Specific examples of the compounds represented by the general formula (1) that are not included in the compounds represented by the general formulas (2) to (6) include 1- [phenyl (pyridyl) methyl. ] Imidazole, 1- (dipyridylmethyl) imidazole, 1- [diphenyl (pyridyl) methyl] imidazole, 1-[(dipyridyl) phenylmethyl] imidazole, 1- (tripyridylmethyl) imidazole 2-{[phenyl (pyridyl) methyl] oxy} ethanol, 2-[(dipyridylmethyl) oxy] ethanol, 2-{[diphenyl (pyridyl) methyl] oxy} ethanol, 2- { [Dipyridyl (phenyl) methyl] oxy} ethanol, 2-[(tripyridylmethyl) oxy] ethanol, 2-{[phenyl (pyridyl) methyl] amino} ethanol, 2-[(dipyridylmethyl) Amino] eta -Nor, 2-{[diphenyl (pyridyl) methyl] amino} ethanol, 2-{[dipyridyl (phenyl) methyl] amino} ethanol, 2-[(tripyridylmethyl) amino] ethanol, 2-{[phenyl (pyridyl) methyl] oxy} ethylamine, 2-[(dipyridylmethyl) oxy] ethylamine, 2-{[diphenyl (pyridyl) methyl] oxy} ethylamine, 2-{[dipyridyl (phenyl) methyl] oxy } Ethylamine, 2-[(tripyridylmethyl) oxy] ethylamine, 1- [phenyl (pyridyl) methyl] pyrrolidine, 1-dipyridylmethylpyrrolidine, 1- [diphenyl (pyridyl) methyl] pyrrolidine, 1-[(dipyridyl) phenyl Methyl] pyrrolidine, 1- (tripyridylmethyl) pyrrolidine, [phenyl (pyridyl) methyl] piperidine, dipyridyl Preferred examples include methylpiperidine, [diphenyl (pyridyl) methyl] piperidine, 1-[(dipyridyl) phenylmethyl] piperidine, 1- (tripyridylmethyl) piperidine and / or their pharmacologically acceptable salts. . Specific examples of preferred compounds among the compounds represented by the general formula (1) include 1- (diphenylmethyl) imidazole (compound 1) and 1- (triphenylmethyl) imidazole. (Compound 2), 2-[(Diphenylmethyl) oxy] ethanol (Compound 3), 2-[(Triphenylmethyl) oxy] ethanol (Compound 4), 2-[(Diphenylmethyl) amino] ethanol -L (compound 5), 2-[(triphenylmethyl) amino] ethanol (compound 6), 2-[(diphenylmethyl) oxy] ethylamine (compound 7), 2-[(triphenylmethyl) oxy] Ethylamine (Compound 8), 1- (Diphenylmethyl) pyrrolidine (Compound 9), 1- (Triphenylmethyl) pyrrolidine (Compound 10), 1- (Diphenylmethyl) piperidine (Compound 1) ), 1- (triphenylmethyl) piperidine (Compound 12) and / or their pharmacologically acceptable salts are suitably be exemplified. When such a compound is contained in the composition together with the anti-wrinkle agent described later, it exhibits an excellent skin beautifying effect and an effect of preventing or improving wrinkle formation. Further, such compounds and / or pharmacologically acceptable salts thereof have excellent safety and stability, and can be contained stably and safely in the composition.

  Here, the compound represented by the general formula (2) will be described. In the formula, A is di- or triarylmethyl independently selected from the group consisting of unsubstituted or substituted aryl groups. B represents a cyclic or acyclic aliphatic or aromatic hydrocarbon group in which the bonding site to A is a hetero atom, a hydrogen atom, a hydrogen atom or a carbon atom may be substituted with a hetero atom. To express. Specific examples of the aryl group of the di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups in A include a phenyl group and a naphthyl group. , Biphenyl group, methylphenyl group, ethylphenyl group, propylphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, hydroxyphenyl group, aminophenyl group, N-methylaminophenyl group, N-ethylaminophenyl group N-propylaminophenyl group, N, N-dimethylaminophenyl group, N, N-diethylaminophenyl group, N, N-dipropylaminophenyl group, fluorophenyl group, difluorophenyl group, trifluoromethylphenyl group, chlorophenyl Group, bromophenyl group, methylnaphthyl group, Tylnaphthyl group, propylnaphthyl group, methoxynaphthyl group, ethoxynaphthyl group, propyloxynaphthyl group, hydroxynaphthyl group, aminonaphthyl group, N-methylaminonaphthyl group, N-ethylaminonaphthyl group, N-propylaminonaphthyl group, N , N-dimethylaminonaphthyl group, N, N-diethylaminonaphthyl group, N, N-dipropylaminonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, chloronaphthyl group, bromonaphthyl group, etc. are preferable More preferred examples include a phenyl group, a methylphenyl group, a methoxyphenyl group, and a naphthyl group. B represents a cyclic atom or a non-cyclic aliphatic or aromatic hydrocarbon group in which the bonding site to A is a hetero atom, a hydrogen atom, a hydrogen atom or a carbon atom optionally substituted with a hetero atom; For example, a mono- or di-substituted amino group, a hydrogen atom or a carbon having a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms in which a hydroxyl group, an amino group, a hydrogen atom or a carbon atom may be substituted by a hetero atom An alkyloxy group having a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms in which an atom may be substituted by a hetero atom, a hydrogen atom or a carbon atom having 1 to 8 carbon atoms in which the carbon atom may be substituted by a hetero atom, More preferably, a mono- or dialkyl-substituted amino group having an aliphatic hydrocarbon group having 1 to 4 carbon atoms, a hydrogen atom or a carbon atom having 1 to 8 carbon atoms in which the carbon atom may be substituted with a hetero atom, more preferably. Is a mono or di having an alkyloxy group having a C 1-4 aliphatic hydrocarbon group, a hydrogen atom or a C 3-8 aromatic hydrocarbon group in which the carbon atom may be substituted by a hetero atom. A substituted amino group, a hydrogen atom or an alkyloxy group having an aromatic hydrocarbon group having 3 to 8 carbon atoms which may be substituted with a hetero atom. The B is a hydrogen atom or a disubstituted amino group having a cyclic aliphatic hydrocarbon group having 3 to 8 carbon atoms in which a carbon atom may be substituted with a heteroatom, or a hydrogen atom or a carbon atom is a heteroatom. In the case of representing a disubstituted amino group having an aromatic hydrocarbon group having 3 to 8 carbon atoms which may be substituted by, bonding of A and B to a ring of a cyclic aliphatic hydrocarbon group or an aromatic group The structure including the hetero atom of the site is also included. Of the compounds represented by the general formula (2), more preferred are the compounds represented by the general formulas (3) to (6) and / or pharmacologically acceptable salts thereof. Specific examples of preferred compounds are 1- (diphenylmethyl) imidazole (compound 1), 1- (triphenylmethyl) imidazole (compound 2), 2-[(diphenylmethyl). ) Oxy] ethanol (compound 3), 2-[(triphenylmethyl) oxy] ethanol (compound 4), 2-[(diphenylmethyl) amino] ethanol (compound 5), 2-[( Triphenylmethyl) amino] ethanol (compound 6), 2-[(diphenylmethyl) oxy] ethylamine (compound 7), 2-[(triphenylmethyl) oxy] ethylamine (compound 8), 1- (diphenylmethyl) L) pyrrolidine (compound 9), 1- (triphenylmethyl) pyrrolidine (compound 10), 1- (diphenylmethyl) piperidine (compound 11), 1- (triphenylmethyl) piperidine (compound 12) and / or their Preferred examples include pharmacologically acceptable salts. When such a compound is contained in the composition together with the anti-wrinkle agent described later, it exhibits an excellent skin beautifying effect and an effect of preventing or improving wrinkles. Further, such compounds and / or pharmacologically acceptable salts thereof have excellent safety and stability, and can be contained stably and safely in the composition.

Here, the compound represented by the general formula (3) will be described. In the formula, A is di- or triarylmethyl independently selected from the group consisting of unsubstituted or substituted aryl groups. Represents a group, X represents a nitrogen atom or an NH group, and R1 represents a C3-8 cyclic aliphatic hydrocarbon group in which a hydrogen atom, a hydrogen atom or a carbon atom may be substituted with a hetero atom. The ring of the cycloaliphatic hydrocarbon group also includes a ring formed by bonding the other end of R1 to X again. Specific examples of the aryl group of the di- or triaromatic methyl group independently selected from the group consisting of unsubstituted or substituted aryl groups in A include phenyl. Group, naphthyl group, biphenyl group, methylphenyl group, ethylphenyl group, propylphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, hydroxyphenyl group, aminophenyl group, N-methylaminophenyl group, N- Ethylaminophenyl group, N-propylaminophenyl group, N, N-dimethylaminophenyl group, N, N-diethylaminophenyl group, N, N-dipropylaminophenyl group, fluorophenyl group, difluorophenyl group, trifluoromethyl Phenyl group, chlorophenyl group, bromophenyl group, methylnaphthyl group, Ethyl naphthyl group, propyl naphthyl group, methoxy naphthyl group, ethoxy naphthyl group, propyloxy naphthyl group, hydroxy naphthyl group, amino naphthyl group, N-methylamino naphthyl group, N-ethylamino naphthyl group, N-propylamino naphthyl group, N, N-dimethylaminonaphthyl group, N, N-diethylaminonaphthyl group, N, N-dipropylaminonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, chloronaphthyl group, bromonaphthyl group, etc. A preferred example is a phenyl group, a methylphenyl group, a methoxyphenyl group, a naphthyl group, and the like. X represents a nitrogen atom or an NH group. R1 represents a hydrogen atom, a hydrogen atom or a C3-C8 cyclic aliphatic hydrocarbon group in which a carbon atom may be substituted with a hetero atom, and the ring of the cyclic aliphatic hydrocarbon group is represented by R1 A ring formed by bonding the other end to X again is also included. Specific examples of preferred R1 include N-cyclopropyl group, N-cyclobutyl group, N-cyclopentyl group, N-cyclohexyl group, N-cycloheptyl group, N-cyclooctyl group, and succinimide group. It can illustrate suitably. Examples of the substituent having a ring structure in which the ring of the cyclic aliphatic hydrocarbon group is formed by rebonding the other end of R1 to X (including the X moiety) include a pyrrolidino group, a methylpyrrolidino group , Ethylpyrrolidino group, propylpyrrolidino group, methoxypyrrolidino group, ethoxypyrrolidino group, propyloxypyrrolidino group, hydroxypyrrolidino group, aminopyrrolidino group, N-methylpyrrolidino group, N-ethylpyrrolidino group N-propylpyrrolidino group, N, N-dimethylpyrrolidino group, N, N-diethylpyrrolidino group, N, N-dipropylpyrrolidino group, fluoropyrrolidino group, difluoropyrrolidino group, trifluoromethylpyrrole Dino group, chloropyrrolidino group, piperidyl group, methylpiperidyl group, ethylpiperidyl group, propylpiperidyl group, methoxypiperidyl group Group, ethoxypiperidyl group, propyloxypiperidyl group, hydroxypiperidyl group, aminopiperidyl group, N-methylpiperidyl group, N-ethylpiperidyl group, N-propylpiperidyl group, N, N-dimethylpiperidyl group, N, N-diethyl Piperidyl group, N, N-dipropylpiperidyl group, fluoropiperidyl group, difluoropiperidyl group, trifluoromethylpiperidyl group, chloropiperidyl group, piperazino group, methylpiperazino group, ethylpiperazino group, propylpiperazino group, methoxypiperazino group , Ethoxypiperazino group, propyloxypiperazino group, hydroxypiperazino group, aminopiperazino group, N-methylpiperazino group, N-ethylpiperazino group, N-propylpiperazino group, N, N-dimethylpiperazino group N, N-diethylpiperazino group N, N-dipropylpiperazino group, fluoropiperazino group, difluoropiperazino group, trifluoromethylpiperazino group, chloropiperazino group, morpholino group, methylmorpholino group, ethylmorpholino group, propylmorpholino group, methoxy Morpholino group, ethoxymorpholino group, propyloxymorpholino group, hydroxymorpholino group, aminomorpholino group, N-methylmorpholino group, N-ethylmorpholino group, N-propylmorpholino group, N, N-dimethylmorpholino group, N, N- A diethylmorpholino group, an N, N-dipropylmorpholino group, a fluoromorpholino group, a difluoromorpholino group, a trifluoromethylmorpholino group, a chloromorpholino group and the like can be suitably exemplified, and more preferably, a pyrrolidyl group, a piperidyl group, a piperazyl group, Preferably morpholino groups A pyrrolidino group, a piperidino group, a piperazino group, and a morpholino group can be preferably exemplified. Specific examples of preferable compounds among the compounds represented by the general formula (3) include N- (diphenylmethyl) succinimide, N-[(methylphenyl) phenylmethyl] succinimide, and N- [bis (methyl Phenyl) methyl] succinimide, N-[(ethylphenyl) phenylmethyl] succinimide, N- [bis (ethylphenyl) methyl] succinimide, N-[(methoxyphenyl) phenylmethyl] succinimide, N- [bis (methoxyphenyl) Methyl] succinimide, N-[(ethoxyphenyl) phenylmethyl] succinimide, N- [bis (ethoxyphenyl) methyl] succinimide, N-[(fluorophenyl) phenylmethyl] succinimide, N- [bis (fluorophenyl) methyl] Succinimide, N- (triphenylmethyl) succinimide, N- [ Diphenyl (methylphenyl) methyl] succinimide, N- [bis (methylphenyl) phenylmethyl] succinimide, N- [tris (methylphenyl) methyl] succinimide, N- [diphenyl (ethylphenyl) methyl] succinimide, N- [bis (Ethylphenyl) phenylmethyl] succinimide, N- [tris (ethylphenyl) methyl] succinimide, N- [diphenyl (methoxyphenyl) methyl] succinimide, N- [bis (methoxyphenyl) phenylmethyl] succinimide, N- [tris (Methoxyphenyl) methyl] succinimide, N- [diphenyl (ethoxyphenyl) methyl] succinimide, N- [bis (ethoxyphenyl) phenylmethyl] succinimide, N- [tris (ethoxyphenyl) methyl] succinimide, N- [diphenyl ( F Olophenyl) methyl] succinimide, N- [bis (fluorophenyl) phenylmethyl] succinimide, N- [tris (fluorophenyl) methyl] succinimide, 1- (diphenylmethyl) pyrrolidine (compound 9), 1-[(methylphenyl) Phenylmethyl] pyrrolidine, 1- [bis (methylphenyl) methyl] pyrrolidine, 1-[(ethylphenyl) phenylmethyl] pyrrolidine, 1- [bis (ethylphenyl) methyl] pyrrolidine, 1-[(methoxyphenyl) phenylmethyl ] Pyrrolidine, 1- [bis (methoxyphenyl) methyl] pyrrolidine, 1-[(ethylphenyl) phenylmethyl] pyrrolidine, 1- [bis (ethylphenyl) methyl] pyrrolidine, 1-[(hydroxyphenyl) phenylmethyl] pyrrolidine , 1- [bis (hydroxyphenyl) methyl Ru] pyrrolidine, 1-[(aminophenyl) phenylmethyl] pyrrolidine, 1- [bis (aminophenyl) methyl] pyrrolidine, 1-[(fluorophenyl) phenylmethyl] pyrrolidine, 1- [bis (fluorophenyl) methyl] Pyrrolidine, 1-[(chlorophenyl) phenylmethyl] pyrrolidine, 1- [bis (chlorophenyl) methyl] pyrrolidine, 1- (triphenylmethyl) pyrrolidine (compound 10), 1- [diphenyl (methylphenyl) methyl] pyrrolidine, 1 -[Bis (methylphenyl) phenylmethyl] pyrrolidine, 1- [tris (methylphenyl) methyl] pyrrolidine, 1- [diphenyl (ethylphenyl) methyl] pyrrolidine, 1- [bis (ethylphenyl) phenylmethyl] pyrrolidine, 1 -[Tris (ethylphenyl) methyl] pyrrolidine, 1- [di Phenyl (methoxyphenyl) methyl] pyrrolidine, 1- [bis (methoxyphenyl) phenylmethyl] pyrrolidine, 1- [tris (methoxyphenyl) methyl] pyrrolidine, 1- [diphenyl (ethoxyphenyl) methyl] pyrrolidine, 1- [bis (Ethoxyphenyl) phenylmethyl] pyrrolidine, 1- [tris (ethoxyphenyl) methyl] pyrrolidine, 1- [diphenyl (hydroxyphenyl) methyl] pyrrolidine, 1- [bis (hydroxyphenyl) phenylmethyl] pyrrolidine, 1- [tris (Hydroxyphenyl) methyl] pyrrolidine, 1-[(aminophenyl) diphenylmethyl] pyrrolidine, 1- [bis (aminophenyl) phenylmethyl] pyrrolidine, 1- [tris (aminophenyl) methyl] pyrrolidine, 1- [diphenyl ( Fluorophenyl) methyl] Loridine, 1- [bis (fluorophenyl) phenylmethyl] pyrrolidine, 1- [tris (fluorophenyl) methyl] pyrrolidine, 1- (diphenylmethyl) piperidine (compound 11), 1-[(methylphenyl) phenylmethyl] pi Peridine, 1- [bis (methylphenyl) methyl] piperidine, 1-[(ethylphenyl) phenylmethyl] piperidine, 1- [bis (ethylphenyl) methyl] piperidine, 1-[(methoxy Phenyl) phenylmethyl] piperidine, 1- [bis (methoxyphenyl) methyl] piperidine, 1-[(ethylphenyl) phenylmethyl] piperidine, 1- [bis (ethylphenyl) methyl] piperidine 1-[(hydroxyphenyl) phenylmethyl] piperidine, 1- [bis (hydroxyphenyl) methyl] piperidine, 1-[(aminophenyl) Nyl) phenylmethyl] piperidine, 1- [bis (aminophenyl) methyl] piperidine, 1-[(fluorophenyl) phenylmethyl] piperidine, 1- [bis (fluorophenyl) methyl] piperidine, 1-[(chlorophenyl) phenyl Methyl] piperidine, 1- [bis (chlorophenyl) methyl] piperidine, 1- (triphenylmethyl) piperidine (compound 12), 1- [diphenyl (methylphenyl) methyl] piperidine, 1- [bis (methylphenyl) phenylmethyl ] Piperidine, 1- [tris (methylphenyl) methyl] piperidine, 1- [diphenyl (ethylphenyl) methyl] piperidine, 1- [bis (ethylphenyl) phenylmethyl] piperidine, 1- [tris (ethylphenyl) methyl] Piperidine, 1- [diphenyl (methoxyphenyl) methyl L] piperidine, 1- [bis (methoxyphenyl) phenylmethyl] piperidine, 1- [tris (methoxyphenyl) methyl] piperidine, 1- [diphenyl (ethoxyphenyl) methyl] piperidine, 1- [bis (ethoxyphenyl) phenyl Methyl] piperidine, 1- [tris (ethoxyphenyl) methyl] piperidine, 1- [diphenyl (hydroxyphenyl) methyl] piperidine, 1- [bis (hydroxyphenyl) phenylmethyl] piperidine, 1- [tris (hydroxyphenyl) methyl ] Piperidine, 1-[(aminophenyl) diphenylmethyl] piperidine, 1- [bis (aminophenyl) phenylmethyl] piperidine, 1- [tris (aminophenyl) methyl] piperidine, 1- [diphenyl (fluorophenyl) methyl] Piperidine, 1- [bis (fluoro Enyl) phenylmethyl] piperidine, 1- [tris (fluorophenyl) methyl] piperidine, 1- (diphenylmethyl) morpholine, 1-[(methylphenyl) phenylmethyl] morpholine, 1- [bis (methylphenyl) methyl] morpholine 1-[(ethylphenyl) phenylmethyl] morpholine, 1- [bis (ethylphenyl) methyl] morpholine, 1-[(methoxyphenyl) phenylmethyl] morpholine, 1- [bis (methoxyphenyl) methyl] morpholine, -[(Ethylphenyl) phenylmethyl] morpholine, 1- [bis (ethylphenyl) methyl] morpholine, 1-[(hydroxyphenyl) phenylmethyl] morpholine, 1- [bis (hydroxyphenyl) methyl] morpholine, 1- [ (Aminophenyl) phenylmethyl] morpholine, 1- [bis ( Minophenyl) methyl] morpholine, 1-[(fluorophenyl) phenylmethyl] morpholine, 1- [bis (fluorophenyl) methyl] morpholine, 1-[(chlorophenyl) phenylmethyl] morpholine, 1- [bis (chlorophenyl) methyl] Morpholine, 1- (triphenylmethyl) morpholine, 1- [diphenyl (methylphenyl) methyl] morpholine, 1- [bis (methylphenyl) phenylmethyl] morpholine, 1- [tris (methylphenyl) methyl] morpholine, [Diphenyl (ethylphenyl) methyl] morpholine, 1- [bis (ethylphenyl) phenylmethyl] morpholine, 1- [tris (ethylphenyl) methyl] morpholine, 1- [diphenyl (methoxyphenyl) methyl] morpholine, 1- [ Bis (methoxyphenyl) phenylmethyl] Ruphorin, 1- [tris (methoxyphenyl) methyl] morpholine, 1- [diphenyl (ethoxyphenyl) methyl] morpholine, 1- [bis (ethoxyphenyl) phenylmethyl] morpholine, 1- [tris (ethoxyphenyl) methyl] morpholine 1- [diphenyl (hydroxyphenyl) methyl] morpholine, 1- [bis (hydroxyphenyl) phenylmethyl] morpholine, 1- [tris (hydroxyphenyl) methyl] morpholine, 1-[(aminophenyl) diphenylmethyl] morpholine, 1- [bis (aminophenyl) phenylmethyl] morpholine, 1- [tris (aminophenyl) methyl] morpholine, 1- [diphenyl (fluorophenyl) methyl] morpholine, 1- [bis (fluorophenyl) phenylmethyl] morpholine, 1- [Tris (fluoroph Nyl) methyl] morpholine and / or a pharmacologically acceptable salt thereof can be suitably exemplified, and more preferable examples include 1- (diphenylmethyl) pyrrolidine (Compound 9), 1- (triphenylmethyl) pyrrolidine Preferred examples include (Compound 10), 1- (diphenylmethyl) piperidine (Compound 11), 1- (triphenylmethyl) piperidine (Compound 12) and / or pharmacologically acceptable salts thereof. When such a compound is contained in the composition together with the anti-wrinkle agent described later, it exhibits an excellent skin beautifying effect and an effect of preventing or improving wrinkle formation. Further, such compounds and / or pharmacologically acceptable salts thereof have excellent safety and stability, and can be contained stably and safely in the composition.

  Here, the compound represented by the general formula (4) will be described. In the formula, A is a di- or triaryl independently selected from the group consisting of unsubstituted or substituted aryl groups. Represents a group, X represents an oxygen atom, R2 represents a hydrogen atom, a hydrogen atom or an aliphatic hydrocarbon having 1 to 8 carbon atoms in which a carbon atom may be substituted with a hetero atom. Specific examples of the aryl group of the di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups in A include a phenyl group and a naphthyl group. Group, biphenyl group, methylphenyl group, ethylphenyl group, propylphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, hydroxyphenyl group, aminophenyl group, N-methylaminophenyl group, N-ethylaminophenyl Group, N-propylaminophenyl group, N, N-dimethylaminophenyl group, N, N-diethylaminophenyl group, N, N-dipropylaminophenyl group, fluorophenyl group, difluorophenyl group, trifluoromethylphenyl group, Chlorophenyl group, bromophenyl group, methylnaphthyl group, Ethyl naphthyl group, propyl naphthyl group, methoxy naphthyl group, ethoxy naphthyl group, propyloxy naphthyl group, hydroxy naphthyl group, amino naphthyl group, N-methylamino naphthyl group, N-ethylamino naphthyl group, N-propylamino naphthyl group, N, N-dimethylaminonaphthyl group, N, N-diethylaminonaphthyl group, N, N-dipropylaminonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, chloronaphthyl group, bromonaphthyl group, etc. A preferred example is a phenyl group, a naphthyl group, a methylphenyl group, a methoxyphenyl group, and the like. X represents an oxygen atom. R2 represents a hydrogen atom, a hydrogen atom, or a C1-C8 aliphatic hydrocarbon in which a carbon atom may be substituted with a heteroatom, more preferably a C1-C4 aliphatic hydrocarbon. , Hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxypentyl group, hydroxyhexyl group, hydroxyheptyl group, hydroxyoctyl group, methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, methoxy Pentyl group, methoxyhexyl group, methoxyheptyl group, methoxyoctyl group, dihydroxymethyl group, dihydroxyethyl group, dihydroxypropyl group, dihydroxybutyl group, dihydroxypentyl group, dihydroxyhexyl group, dihydroxyheptyl group, dihydroxyoctyl Group, aminomethyl group, aminoethyl group, aminopropyl group, aminobutyl group, aminopentyl group, aminohexyl group, aminoheptyl group, aminooctyl group and the like can be suitably exemplified, more preferably hydroxyethyl group, aminoethyl Preferred examples include a group and a methoxyethyl group. Of the compounds represented by the general formula (4), specific examples of preferred compounds include 1- (diphenylmethyloxy) methanol, 3- (diphenylmethyloxy) propanol, 4- (diphenyl). Methyloxy) butanol, 5- (diphenylmethyloxy) pentanol, 6- (diphenylmethyloxy) hexanol, 7- (diphenylmethyloxy) heptanol, 8- (diphenylmethyloxy) octanol 1- (triphenylmethyloxy) methanol, 3- (triphenylmethyloxy) propanol, 4- (triphenylmethyloxy) butanol, 5- (triphenylmethyloxy) pentanol, 6 -(Triphenylmethyloxy) hexanol, 7- (triphenylmethyloxy) heptanol, 8- (triphenyl) Methyloxy) octanol, 1- (diphenylmethyloxy) methylamine, 3- (diphenylmethyloxy) propylamineamine, 4- (diphenylmethyloxy) butylamine, 5- (diphenylmethyloxy) pentylamine, 6- ( Diphenylmethyloxy) hexylamine, 7- (diphenylmethyloxy) heptylamine, 8- (diphenylmethyloxy) octylamine, 1- (triphenylmethyloxy) methylamine, 3- (triphenylmethyloxy) propylamine, 4 -(Triphenylmethyloxy) butylamine, 5- (triphenylmethyloxy) pentylamine, 6- (triphenylmethyloxy) hexylamine, 7- (triphenylmethyloxy) heptylamine, 8- (triphenylmethyloxy) ) Octylamine, 1- (diphenylmethylamino) methanol, 3- (diphenylmethylamino) propanol, 4- (diphenylmethylamino) butanol, 5- (diphenylmethylamino) pentanol, 6- (Diphenylmethylamino) hexanol, 7- (diphenylmethylamino) heptanol, 8- (diphenylmethylamino) octanol, 1- (triphenylmethylamino) methanol, 3- (triphenylmethylamino) ) Propanol, 4- (triphenylmethylamino) butanol, 5- (triphenylmethylamino) pentanol, 6- (triphenylmethylamino) hexanol, 7- (triphenylmethylamino) heptanol -L, 8- (triphenylmethylamino) octanol, 2-[(diphenylmethyl) Xyl] ethanol (compound 3), 2-[(methylphenyl) phenylmethyloxy] ethanol, 2- [bis (methylphenyl) methyloxy] ethanol, 2-[(ethylphenyl) phenylmethyloxy ] Ethanol, 2-[(bis (ethylphenyl) methyloxy] ethanol, 2-[(methoxyphenyl) phenylmethyloxy] ethanol, 2-[(bis (methoxyphenyl) methyloxy] ethanol 2-[(ethoxyphenyl) phenylmethyloxy] ethanol, 2-[(bis (ethoxyphenyl) methyloxy] ethanol, 2-[(hydroxyphenyl) phenylmethyloxy] ethanol, 2- [(Bis (hydroxyphenyl) methyloxy] ethanol, 2-[(aminophenyl) phenylmethyloxy] ethanol, 2-[(bis (aminophenyl) L) methyloxy] ethanol, 2-[(fluorophenyl) phenylmethyloxy] ethanol, 2-[(bis (fluorophenyl) methyloxy] ethanol, 2-[(triphenylmethyl) oxy] Ethanol (compound 4), 2- [diphenyl (methylphenyl) methyloxy] ethanol, 2- [bis (methylphenyl) phenylmethyloxy] ethanol, 2- [tris (methylphenyl) methyloxy] Ethanol, 2- [diphenyl (ethylphenyl) methyloxy] ethanol, 2- [bis (ethylphenyl) phenylmethyloxy] ethanol, 2- [tris (ethylphenyl) methyloxy] ethanol, 2- [diphenyl (methoxyphenyl) methyloxy] ethanol, 2- [bis (methoxyphenyl) phenylmethyloxy] ethanol, 2- [to (Methoxyphenyl) methyloxy] ethanol, 2- [diphenyl (ethoxyphenyl) methyloxy] ethanol, 2- [bis (ethoxyphenyl) phenylmethyloxy] ethanol, 2- [tris (ethoxyphenyl) ) Methyloxy] ethanol, 2- [diphenyl (hydroxyphenyl) methyloxy] ethanol, 2- [bis (hydroxyphenyl) phenylmethyloxy] ethanol, 2- [tris (hydroxyphenyl) methyloxy] Ethanol, 2-[(aminophenyl) diphenylmethyloxy] ethanol, 2- [bis (aminophenyl) phenylmethyloxy] ethanol, 2- [tris (aminophenyl) methyloxy] ethanol, 2- [diphenyl (fluorophenyl) methyloxy] ethanol, 2- [bis (fluorophenyl) phenyl Nylmethyloxy] ethanol, 2- [tris (fluorophenyl) methyloxy] ethanol, 2-[(diphenylmethyl) oxy] ethylamine (compound 7), 2-[(methylphenyl) phenylmethyloxy] ethylamine 2- [bis (methylphenyl) methyloxy] ethylamine, 2-[(ethylphenyl) phenylmethyloxy] ethylamine, 2-[(bis (ethylphenyl) methyloxy] ethylamine, 2-[(methoxyphenyl) phenylmethyl Oxy] ethylamine, 2-[(bis (methoxyphenyl) methyloxy] ethylamine, 2-[(ethoxyphenyl) phenylmethyloxy] ethylamine, 2-[(bis (ethoxyphenyl) methyloxy] ethylamine, 2-[(hydroxy Phenyl) phenylmethyloxy] ethylamine, 2- [ Bis (hydroxyphenyl) methyloxy] ethylamine, 2-[(aminophenyl) phenylmethyloxy] ethylamine, 2-[(bis (aminophenyl) methyloxy] ethylamine, 2-[(fluorophenyl) phenylmethyloxyethylamine, 2 -[(Bis (fluorophenyl) methyloxy] ethylamine, 2-[(triphenylmethyl) oxy] ethylamine (compound 8), 2- [diphenyl (methylphenyl) methyloxy] ethylamine, 2- [bis (methylphenyl) Phenylmethyloxy] ethylamine, 2- [tris (methylphenyl) methyloxy] ethylamine, 2- [diphenyl (ethylphenyl) methyloxy] ethylamine, 2- [bis (ethylphenyl) phenylmethyloxy] ethylamine, 2- [tris (Ethylphenyl) Methyloxy] ethylamine, 2- [diphenyl (methoxyphenyl) methyloxy] ethylamine, 2- [bis (methoxyphenyl) phenylmethyloxy] ethylamine, 2- [tris (methoxyphenyl) methyloxy] ethylamine, 2- [diphenyl ( Ethoxyphenyl) methyloxy] ethylamine, 2- [bis (ethoxyphenyl) phenylmethyloxy] ethylamine, 2- [tris (ethoxyphenyl) methyloxy] ethylamine, 2- [diphenyl (hydroxyphenyl) methyloxy] ethylamine, 2- [Bis (hydroxyphenyl) phenylmethyloxy] ethylamine, 2- [tris (hydroxyphenyl) methyloxy] ethylamine, 2-[(aminophenyl) diphenylmethyloxy] ethylamine, 2- [bis (aminophenyl) phenyl Phenylmethyloxy] ethylamine, 2- [tris (aminophenyl) methyloxy] ethylamine, 2- [diphenyl (fluorophenyl) methyloxy] ethylamine, 2- [bis (fluorophenyl) phenylmethyloxy] ethylamine, 2- [tris (Fluorophenyl) methyloxy] ethylamine and / or a pharmacologically acceptable salt thereof can be suitably exemplified, more preferably 2-[(diphenylmethyl) oxy] ethanol (compound 3), 2- [(Triphenylmethyl) oxy] ethanol (compound 4), 2-[(diphenylmethyl) oxy] ethylamine (compound 7), 2-[(triphenylmethyl) oxy] ethylamine (compound 8) and / or The pharmacologically acceptable salt of can be illustrated suitably. When such a compound is contained in the composition together with the anti-wrinkle agent described later, it exhibits an excellent skin beautifying effect and an effect of preventing or improving wrinkle formation. Further, such compounds and / or pharmacologically acceptable salts thereof have excellent safety and stability, and can be contained stably and safely in the composition.

  Here, the compound represented by the general formula (5) will be described. In the formula, A is di- or triarylmethyl independently selected from the group consisting of unsubstituted or substituted aryl groups. Represents a group, X represents a nitrogen atom, and R3 and R4 each independently represent a C1-C8 aliphatic hydrocarbon in which a hydrogen atom, a hydrogen atom, or a carbon atom may be substituted with a heteroatom. To express. Specific examples of the aryl group of the di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups in A include a phenyl group and a naphthyl group. Group, biphenyl group, methylphenyl group, ethylphenyl group, propylphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, hydroxyphenyl group, aminophenyl group, N-methylaminophenyl group, N-ethylaminophenyl Group, N-propylaminophenyl group, N, N-dimethylaminophenyl group, N, N-diethylaminophenyl group, N, N-dipropylaminophenyl group, fluorophenyl group, difluorophenyl group, trifluoromethylphenyl group, Chlorophenyl group, bromophenyl group, methylnaphthyl group, Ethyl naphthyl group, propyl naphthyl group, methoxy naphthyl group, ethoxy naphthyl group, propyloxy naphthyl group, hydroxy naphthyl group, amino naphthyl group, N-methylamino naphthyl group, N-ethylamino naphthyl group, N-propylamino naphthyl group, N, N-dimethylaminonaphthyl group, N, N-diethylaminonaphthyl group, N, N-dipropylaminonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, chloronaphthyl group, bromonaphthyl group, etc. A preferred example is a phenyl group, a naphthyl group, a methylphenyl group, a methoxyphenyl group, and the like. X represents a nitrogen atom. R3 and R4 each independently represent a hydrogen atom, a hydrogen atom, a hydrogen atom or a carbon atom having 1 to 8 carbon atoms, more preferably an aliphatic hydrocarbon group having 1 to 4 carbon atoms, which may be substituted with a hetero atom. Specific examples of preferred R3 and R4 are as follows: hydrogen atom, hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxypentyl group, hydroxyhexyl group, hydroxyheptyl group, hydroxy Octyl group, methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, methoxypentyl group, methoxyhexyl group, methoxyheptyl group, methoxyoctyl group, dihydroxymethyl group, dihydroxyethyl group, dihydroxypropyl group, dihydroxybutyl group , Dihydroxy pliers Group, dihydroxyhexyl group, dihydroxyheptyl group, dihydroxyoctyl group, aminomethyl group, aminoethyl group, aminopropyl group, aminobutyl group, aminopentyl group, aminohexyl group, aminoheptyl group, aminooctyl group, etc. are preferred A hydroxyethyl group, an aminoethyl group, and a methoxyethyl group can be preferably exemplified. Of the compounds represented by the general formula (5), specific examples of preferred compounds include 2-[(diphenylmethyl) amino] ethanol (compound 5), 2-[(methylphenyl) phenylmethyl. Amino] ethanol, 2- [bis (methylphenyl) methylamino] ethanol, 2-[(ethylphenyl) phenylmethylamino] ethanol, 2-[(bis (ethylphenyl) methylamino] ethanol 2-[(methoxyphenyl) phenylmethylamino] ethanol, 2-[(bis (methoxyphenyl) methylamino] ethanol, 2-[(ethoxyphenyl) phenylmethylamino] ethanol, 2- [(Bis (ethoxyphenyl) methylamino] ethanol, 2-[(hydroxyphenyl) phenylmethylamino] ethanol, 2-[(bis (hydroxyphenyl) methyl) Amino] ethanol, 2-[(aminophenyl) phenylmethylamino] ethanol, 2-[(bis (aminophenyl) methylamino] ethanol, 2-[(fluorophenyl) phenylmethylamino] ethanol 2-[(bis (fluorophenyl) methylamino] ethanol, 2-[(triphenylmethyl) amino] ethanol (compound 6), 2- [diphenyl (methylphenyl) methylamino] ethanol 2- [bis (methylphenyl) phenylmethylamino] ethanol, 2- [tris (methylphenyl) methylamino] ethanol, 2- [diphenyl (ethylphenyl) methylamino] ethanol, 2- [ Bis (ethylphenyl) phenylmethylamino] ethanol, 2- [tris (ethylphenyl) methylamino] ethanol, 2- [diphenyl (methoxyphenyl) Nyl) methylamino] ethanol, 2- [bis (methoxyphenyl) phenylmethylamino] ethanol, 2- [tris (methoxyphenyl) methylamino] ethanol, 2- [diphenyl (ethoxyphenyl) methylamino ] Ethanol, 2- [bis (ethoxyphenyl) phenylmethylamino] ethanol, 2- [tris (ethoxyphenyl) methylamino] ethanol, 2- [diphenyl (hydroxyphenyl) methylamino] ethanol 2- [bis (hydroxyphenyl) phenylmethylamino] ethanol, 2- [tris (hydroxyphenyl) methylamino] ethanol, 2-[(aminophenyl) diphenylmethylamino] ethanol, 2- [ Bis (aminophenyl) phenylmethylamino] ethanol, 2- [tris (aminophenyl) methylamino] ethanol Nor, 2- [diphenyl (fluorophenyl) methylamino] ethanol, 2- [bis (fluorophenyl) phenylmethylamino] ethanol, 2- [tris (fluorophenyl) methylamino] ethanol and And / or a pharmacologically acceptable salt thereof can be suitably exemplified. More preferably, 2-[(diphenylmethyl) amino] ethanol (compound 5), 2-[(triphenylmethyl) amino] ethanol -(Compound 6) and / or pharmacologically acceptable salts thereof can be preferably exemplified. When such a compound is contained in the composition together with the anti-wrinkle agent described later, it exhibits an excellent skin beautifying effect and an effect of preventing or improving wrinkle formation. Further, such compounds and / or pharmacologically acceptable salts thereof have excellent safety and stability, and can be contained stably and safely in the composition.

  Here, the compound represented by the general formula (6) will be described. In the formula, A is di- or triarylmethyl independently selected from the group consisting of unsubstituted or substituted aryl groups. X represents a nitrogen atom or an NH group, R5 represents a hydrogen atom or an aromatic hydrocarbon group having 3 to 8 carbon atoms in which a carbon atom may be substituted with a hetero atom, and the aromatic carbonization The hydrogen group also includes a group in which X is present in the ring. Specific examples of the aryl group of the di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups in A include a phenyl group and a naphthyl group. Group, biphenyl group, methylphenyl group, ethylphenyl group, propylphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, hydroxyphenyl group, aminophenyl group, N-methylaminophenyl group, N-ethylaminophenyl Group, N-propylaminophenyl group, N, N-dimethylaminophenyl group, N, N-diethylaminophenyl group, N, N-dipropylaminophenyl group, fluorophenyl group, difluorophenyl group, trifluoromethylphenyl group, Chlorophenyl group, bromophenyl group, methylnaphthyl group, Ethyl naphthyl group, propyl naphthyl group, methoxy naphthyl group, ethoxy naphthyl group, propyloxy naphthyl group, hydroxy naphthyl group, amino naphthyl group, N-methylamino naphthyl group, N-ethylamino naphthyl group, N-propylamino naphthyl group, N, N-dimethylaminonaphthyl group, N, N-diethylaminonaphthyl group, N, N-dipropylaminonaphthyl group, fluoronaphthyl group, difluoronaphthyl group, trifluoromethylnaphthyl group, chloronaphthyl group, bromonaphthyl group, etc. A preferred example is a phenyl group, a naphthyl group, a methylphenyl group, a methoxyphenyl group, and the like. X represents a nitrogen atom or an NH group. R5 represents a hydrogen atom or an aromatic hydrocarbon group having 3 to 8 carbon atoms in which a carbon atom may be substituted with a hetero atom, and the aromatic hydrocarbon group may be a group in which X is present in the ring. Represents an included group. Specific examples of the aromatic hydrocarbon group include a phenyl group, a pyridyl group, an imidazole group, a furyl group, a thienyl group, and the like, and more preferably an imidazole group. Specific examples of the compound represented by the general formula (6) include 1- (diphenylmethyl) imidazole (compound 1), 1-[(methylphenyl) methyl] imidazole, 1- [bis ( Methylphenyl) methyl] imidazole, 1-[(ethylphenyl) methyl] imidazole, 1- [bis (ethylphenyl) methyl] imidazole, 1-[(methoxyphenyl) methyl] imidazole, 1 -[Bis (methoxyphenyl) methyl] imidazole, 1-[(ethoxyphenyl) methyl] imidazole, 1- [bis (ethoxyphenyl) methyl] imidazole, 1-[(hydroxyphenyl) methyl] imidazole 1- [bis (hydroxyphenyl) methyl] imidazole, 1-[(aminophenyl) methyl] imidazole, 1- [bis (aminophenyl) methyl] imidazole, -[(Fluorophenyl) methyl] imidazole, 1- [bis (fluorophenyl) methyl] imidazole, 1- (triphenylmethyl) imidazole (compound 2), 1- [diphenyl (methylphenyl) methyl ] Imidazole, 1- [bis (methylphenyl) phenylmethyl] imidazole, 1- [tris (methylphenyl) methyl] imidazole, 1- [diphenyl (ethylphenyl) methyl] imidazole, 1- [Bis (ethylphenyl) phenylmethyl] imidazole, 1- [tris (ethylphenyl) methyl] imidazole, 1- [diphenyl (methoxyphenyl) methyl] imidazole, 1- [bis (methoxyphenyl) phenyl Methyl] imidazole, 1- [tris (methoxyphenyl) methyl] imidazole, 1- [diphenyl (ethoxyphenyl) methyl ] Imidazole, 1- [bis (methoxyphenyl) phenylmethyl] imidazole, 1- [tris (ethoxyphenyl) methyl] imidazole, 1- [diphenyl (hydroxyphenyl) methyl] imidazole, 1- [Bis (hydroxyphenyl) phenylmethyl] imidazole, 1- [tris (hydroxyphenyl) methyl] imidazole, 1-[(aminophenyl) diphenylmethyl] imidazole, 1- [bis (aminophenyl) phenyl Methyl] imidazole, 1- [tris (aminophenyl) methyl] imidazole, 1- [diphenyl (fluorophenyl) methyl] imidazole, 1- [bis (fluorophenyl) phenylmethyl] imidazole, 1 -[Tris (fluorophenyl) methyl] imidazole and / or their pharmacologically acceptable salts are preferred examples More preferably, 1- (diphenylmethyl) imidazole (compound 1), 1- (triphenylmethyl) imidazole (compound 2) and / or pharmacologically acceptable salts thereof are preferred. It can be illustrated. When such a compound is contained in the composition together with the anti-wrinkle agent described later, it exhibits an excellent skin beautifying effect and an effect of preventing or improving wrinkles. Further, such compounds and / or pharmacologically acceptable salts thereof have excellent safety and stability, and can be contained stably and safely in the composition.

  The compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof is included in the composition together with an anti-wrinkle agent to be described later, thereby preventing skin beautifying, especially, preventing wrinkle formation or Demonstrate improvement. An excellent skin beautifying effect obtained by including the compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof together with an anti-wrinkle agent, and prevention of wrinkle formation Or, the improvement action, in other words, the skin beautification action, and the enhancement action in the prevention or improvement effect against wrinkle formation, in addition to the additive or synergistic effect in the pharmacological effects of both components, the improvement in the delivery efficiency to the target site, etc. It is thought to be due to pharmacokinetic effects, pharmaceutical additive or synergistic effects.

  The compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof can be synthesized according to the method shown below or with reference, using commercially available corresponding reagents as starting materials. Regarding the synthesis method of the compound represented by the general formula (1), it can be produced according to the synthesis method described in PCT / JP2009 / 071279 filed by the present applicant. Such a compound can be used as it is in the composition together with the anti-wrinkle agent described later as it is, and can be used to enhance the effect of preventing or improving wrinkle formation, wrinkle formation, but is pharmacologically acceptable. It can also be treated with an acid or base to convert it to a salt form and used as a salt. For example, mineral salts such as hydrochloride, sulfate, nitrate, phosphate, carbonate, maleate, fumarate, oxalate, citrate, lactate, tartrate, methanesulfonate, para Organic acid salts such as toluene sulfonate and benzene sulfonate, alkali metals such as sodium salt and potassium salt, alkaline earth metals such as calcium salt and magnesium salt, triethylamine salt, triethanolamine salt, ammonium salt, monoethanol Preferred examples include organic amine salts such as ruamine salt and piperidine salt, and basic amino acid salts such as lysine salt and alginate.

  The compound represented by the general formula (1) of the present invention and / or a pharmacologically acceptable salt thereof works together with an anti-wrinkle agent to be described later, in beautifying skin action, particularly, preventing or improving wrinkle formation. In order to exert an enhancing effect, the total amount is 0.001% to 10% by weight, more preferably 0.01% to 5% by weight, and still more preferably 0.1% to It is preferable to contain 3 mass%. This is because if the amount is too small, the above effect may not be achieved, and if the amount is too large, the effect may reach its peak and the degree of freedom of the system may be impaired.

<Production Example 1: Method for producing Compound 1 and Compound 2>
Compound 1 and Compound 2 were synthesized according to the method described in JP-A-53-16879. Compound 2 can also be purchased as a reagent from Wako Pure Chemical Industries, Ltd.

１−（ジフェニルメチル）イミダゾ−ル（化合物１）

1- (Diphenylmethyl) imidazole (Compound 1)

１−（トリフェニルメチル）イミダゾ−ル（化合物２）

1- (Triphenylmethyl) imidazole (Compound 2)

<Production Example 2: Production Method of Compound 3 and Compound 4>
Dissolve ethylene glycol (3.10 g, 49.9 mmol) (Wako Pure Chemical) and triphenylchloromethane (1.39 g, 49.9 mmol) (Wako Pure Chemical) in pyridine (6 mL) (Wako Pure Chemical). The mixture was heated to 45 ° C. and stirred for 2 hours. Water (50 mL) was poured into the reaction solution and extracted with toluene (Wako Pure Chemical Industries). The organic layer was dried over anhydrous sodium sulfate (Wako Pure Chemical Industries), and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (chloroform (Wako Pure Chemical): methanol (Wako Pure Chemical) = 9: 1) to obtain Compound 4 (Yield 0.37 g, Yield 24%). Obtained. Moreover, the compound 3 can be obtained by performing the same operation using diphenyl chloromethane instead of triphenyl chloromethane.

<Physical constant of compound 4>
mp. 103-106 ° C
¹ H-HMR (CDCl ₃ ): δ 3.26 (t, J = 4.5 Hz, 2H), 3.75 (t, J = 4.5 Hz, 2H), 7.23-7.54 (m, 15H ).
IR (cm ⁻¹ ): 3337, 1448, 1093, 1061.

２−[（ジフェニルメチル）オキシ]エタノ−ル（化合物３）

2-[(Diphenylmethyl) oxy] ethanol (Compound 3)

２−[（トリフェニルメチル）オキシ]エタノ−ル（化合物４）

2-[(Triphenylmethyl) oxy] ethanol (compound 4)

<Production Example 3: Production Method of Compound 5 and Compound 6>
Triphenylchloromethane (1.00 g, 3.58 mmol) (Wako Pure Chemical Industries) and aminoethanol (2.00 g, 32.7 mmol) were dissolved in acetonitrile (5 mL) and stirred overnight at room temperature. Water (100 mL) was poured into the reaction solution, and the precipitate was suction filtered and dried. The solid was recrystallized with ethanol (Wako Pure Chemical Industries) and water mixed solvent system to obtain compound 6 (yield 0.43 g, yield 39%). Moreover, the compound 5 can be obtained by performing the same operation using diphenylchloromethane instead of triphenylchloromethane.

<Physical constant of compound 6>
mp. 94-97 ° C
¹ H-NMR (d ₆ -DMSO): δ 2.07 (t, J = 6.0 Hz, 2H), 3.51 (t, J = 6.0 Hz, 2H), 7.15-7.42 (m , 15H).
IR (cm ^-1 ): 3244, 1488, 1442, 1025.

２−[（ジフェニルメチル）アミノ]エタノ−ル（化合物５）

2-[(Diphenylmethyl) amino] ethanol (Compound 5)

２−[（トリフェニルメチル）アミノ]エタノ−ル（化合物６）

2-[(Triphenylmethyl) amino] ethanol (Compound 6)

<Production Example 4: Production Method of Compound 7 and Compound 8>
Triphenylchloromethane (1.00 g, 3.58 mmol) (Wako Pure Chemical Industries) and ethanolamine hydrochloride (1.00 g, 10.3 mmol) (Wako Pure Chemical Industries) were dissolved in pyridine (4 mL) and dissolved at room temperature. Stir for days. Water (200 mL) was poured into the reaction solution, and the precipitate was filtered with suction. The solid was suspended in diethyl ether, 3 (N) hydrochloric acid (Wako Pure Chemical Industries) was added, and the mixture was stirred at room temperature for 15 minutes. The insoluble material was dissolved in a mixed solution of ethyl acetate (Wako Pure Chemical Industries) and saturated aqueous sodium bicarbonate (Wako Pure Chemical Industries) and shaken, and then the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate (Wako Pure Chemical Industries), then suction filtered and concentrated under reduced pressure to obtain compound 8 (yield 0.31 g, yield 28%). Moreover, the compound 7 can be obtained by performing the same operation using diphenyl chloromethane instead of triphenyl chloromethane.

<Physical constant of compound 8>
mp. 87-89 ° C.
¹ H-NMR (CDCl ₃ ): δ 2.88 (t, J = 5.1 Hz, 2H), 3.14 (t, J = 5.1 Hz, 2H), 7.24-7.51 (m, 15H ).
IR (cm ⁻¹ ): 3378, 1594, 1448, 1054.

２−[（ジフェニルメチル）オキシ]エチルアミン（化合物７）

2-[(Diphenylmethyl) oxy] ethylamine (Compound 7)

２−[（トリフェニルメチル）オキシ]エチルアミン（化合物８）

2-[(Triphenylmethyl) oxy] ethylamine (Compound 8)

<Production Example 5: Method for producing Compound 9>
Chlorodiphenylmethane (0.50 g, 2.47 mmol) (Wako Pure Chemical), pyrrolidine (0.53 g, 7.45 mmol) (Tokyo Kasei) and potassium iodide (0.10 g, 0.60 mmol) (Wako Pure Chemical) In addition to acetonitrile (20 mL) (Wako Pure Chemical Industries, Ltd.), the mixture was refluxed for 2 hours. After leaving to room temperature, a saturated aqueous solution of sodium bicarbonate (Wako Pure Chemical Industries) was added to the reaction solution, and the mixture was extracted with ethyl acetate (Wako Pure Chemical Industries). The organic layer was dried over anhydrous sodium sulfate (Wako Pure Chemical Industries), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent, chloroform (Wako Pure Chemical Industries): methanol (Wako Pure Chemical Industries) = 99: 1) to obtain Compound 9 (Yield 0.36 g, 61% yield).

<Physical constant of compound 9>
mp. 69-72 ° C
¹ H-NMR (CDCl ₃ ): δ 1.73-1.79 (m, 4H), 2.40-2.44 (m, 4H), 4.15 (s, 1H), 7.12-7. 47 (m, 10H).
IR (cm ⁻¹ ): 2793, 1452, 703.

１−（ジフェニルメチル）ピロリジン（化合物９）

1- (Diphenylmethyl) pyrrolidine (Compound 9)

<Production Example 6: Method for producing Compound 10>
Pyrrolidine (0.26 g, 3.66 mmol) (Wako Pure Chemical), triphenylchloromethane (1.02 g, 3.66 mmol) (Wako Pure Chemical) and potassium carbonate (0.51 g, 3.66 mmol) (Wako Pure Chemical) ) Was added to acetonitrile (30 mL) (Wako Pure Chemical Industries, Ltd.) and refluxed for 5 hours. A saturated aqueous solution of sodium bicarbonate (Wako Pure Chemical Industries) was added to the reaction liquid, and the mixture was extracted with ethyl acetate (Wako Pure Chemical Industries). The organic layer was dried over anhydrous sodium sulfate (Wako Pure Chemical Industries), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent n-hexane (Wako Pure Chemical Industries): ethyl acetate (Wako Pure Chemical Industries) = 9: 1) to obtain compound 10 (yield 0.45 g, yield 80%). It was.

<Physical constant of compound 10>
mp. 127-129 ° C
¹ H-NMR (CDCl ₃ ): δ 1.53-1.65 (m, 4H), 2.00-2.30 (m, 4H), 7.11-7.28 (m, 5H), 7. 48-7.52 (m, 10H).
IR (cm ^-1 ): 2961, 2819, 1486, 1448, 711.

１−（トリフェニルメチル）ピロリジン（化合物１０）

1- (Triphenylmethyl) pyrrolidine (Compound 10)

<Production Example 7: Production Method of Compound 11 and Compound 12>
Piperidine (1.50 g, 17.6 mmol) (Wako Pure Chemicals), triphenylchloromethane (5.40 g, 19.4 mmol) (Wako Pure Chemicals) and potassium carbonate (2.68 g, 19.4 mmol) (Wako Pure Chemicals) ) Was added to acetonitrile (30 mL) (Wako Pure Chemical Industries, Ltd.) and refluxed for 5 hours. A saturated aqueous solution of sodium bicarbonate (Wako Pure Chemical Industries) was added to the reaction liquid, and the mixture was extracted with ethyl acetate (Wako Pure Chemical Industries). The organic layer was dried over anhydrous sodium sulfate (Wako Pure Chemical Industries), and the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized using a mixed solvent of chloroform (Wako Pure Chemicals) and n-hexane (Wako Pure Chemicals) to obtain Compound 12 (yield 1.80 g, yield 31%). Moreover, the compound 11 can be obtained by performing the same operation using diphenyl chloromethane instead of triphenyl chloromethane.

<Physical constant of compound 12>
mp. 156-158 ° C
¹ H-NMR (CDCl ₃ ): δ 0.70-3.50 (m, 10H), 7.14-7.80 (m, 15H).
IR (cm < ^-1 >): 2923, 1485, 1448, 708.

１−（ジフェニルメチル）ピペリジン（化合物１１）

1- (Diphenylmethyl) piperidine (Compound 11)

１−（トリフェニルメチル）ピペリジン（化合物１２）

1- (Triphenylmethyl) piperidine (Compound 12)

<Anti-wrinkle agent of the present invention>
The composition of the present invention comprises 1) a compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent. The anti-wrinkle agent of the present invention can be applied without particular limitation as long as it is an anti-wrinkle agent having a preventive or ameliorating action against wrinkle formation. Preferred is vitamin A or a derivative thereof and / or a drug thereof. Preferable examples include physically acceptable salts, triterpenic acid or triterpenic acid derivatives and / or pharmacologically acceptable salts thereof, and plant extracts having a dermal collagen fiber bundle remodeling action. I can do it. The preventive or ameliorating action for wrinkle formation possessed by the anti-wrinkle agent of the present invention includes a preventive or ameliorating action for wrinkles formed from wrinkles that are formed or wrinkles that are in the process of forming, in addition to the improving action for wrinkles that have already been formed. Is included. The action mechanism of the anti-wrinkle agent of the present invention includes hyaluronic acid production promoting action, collagen production promoting action, matrix metalloproteinase inhibitory action, dermal collagen fiber bundle restructuring action, etc. A mechanism is assumed. The compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, together with an anti-wrinkle agent, is added to a skin external preparation, thereby preventing or improving wrinkle formation of the anti-wrinkle agent. Has the effect of enhancing the action. Any anti-wrinkle agent having an effect of preventing or improving wrinkle formation can be contained in the composition of the present invention, but is particularly preferable from the viewpoint of enhancing the effect of preventing or improving wrinkle formation. Examples thereof include an anti-wrinkle agent having an action of preventing or improving the collapse of the dermal collagen fiber bundle or the disorder of the structure, specifically, triterpenic acid and / or a pharmacologically acceptable salt thereof, triterpenic acid Preferable examples include derivatives and / or pharmacologically acceptable salts thereof, and plant extracts having a dermal collagen fiber bundle remodeling action.

  In addition, the anti-wrinkle agent of the present invention can be preferably exemplified by forms such as simple chemical substances or plant-derived extracts containing the compound. Here, the plant-derived extract means a generic name of the plant extract itself, a fraction obtained by fractionating and purifying the plant extract, a plant extract or fraction, and a solvent-removed product of the purified product. Further, when such an anti-wrinkle agent is contained in the composition together with the compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, only one kind of the above-described anti-wrinkle agent is used. Can be contained alone, or two or more kinds can be contained in combination.

  Regarding the anti-wrinkle agent of the present invention, vitamin A, its derivatives and / or their pharmacologically acceptable salts, triterpenic acid, their acid derivatives and / or their pharmacologically acceptable ones are particularly preferred. Preferred examples thereof include salts and plant extracts having a dermal collagen fiber bundle reconstructing action. Among the vitamin A, derivatives thereof and / or pharmacologically acceptable salts thereof, retinal, derivatives thereof and / or pharmacologically acceptable salts thereof, retinal, Its derivatives and / or their pharmacologically acceptable salts, retinoic acid, their derivatives and / or their pharmacologically acceptable salts can be preferably exemplified, and more preferred ones are specifically exemplified. Examples of retinoyl, its derivatives and / or pharmacologically acceptable salts thereof include retinoic acid, retinoic acetate, retinoic propionate, retinoic butyrate, retinoic octylate, Retinol laurate, retinoyl palmitate, retanol stearate, retanol myristic acid, retinoic oleate, retinoic linolenic acid, retinoic linoleic acid, etc. Retinol fatty acid esters and / or pharmacologically acceptable salts thereof can be preferably exemplified, and retinal, derivatives thereof and / or pharmacologically acceptable salts thereof are retinal. And / or a pharmacologically acceptable salt thereof can be suitably exemplified. Examples of retinoic acid, a derivative thereof and / or a pharmacologically acceptable salt thereof include retinoic acid, tretinoin (all-trans retinoic acid). ), Isotretinoin (13-cis-retinoic acid), methyl retinoic acid, ethyl retinoic acid, retinoic retinoic acid, tocopheryl retinoic acid (tocopheryl residues have any chemical structure of α, β, γ, δ) And / or pharmacologically acceptable salts thereof can be preferably exemplified, and more preferably, retinal, retinal, retinoic Acids, tretinoin, isotretinoin, tocopheryl retinoic acid, retinoic palmitate, retinoic acetate and / or pharmacologically acceptable salts thereof can be preferably exemplified, and among these, more preferred are: Preferred examples include retinoic acid, retinoic acetate, tocopheryl retinoic acid and / or pharmacologically acceptable salts thereof. The vitamin A derivatives and / or pharmacologically acceptable salts thereof used in the present invention can be purchased and used from, for example, a reagent sales manufacturer such as Sigma Aldrich.

  Furthermore, the above-mentioned triterpenic acid, its derivative and / or pharmacologically acceptable salt thereof can be applied without particular limitation as long as it is used in the field of cosmetics and the like, and is preferable. Specific examples of triterpenic acid include ursolic acid, oleanolic acid, betulinic acid and the like, and ursolic acid is particularly preferable. Further, as the triterpenic acid derivative, an aliphatic hydrocarbon ester having 1 to 20 carbon atoms of triterpenic acid, a hydrocarbon ester having 1 to 4 carbon atoms substituted by an aromatic group of triterpenic acid, a phosphate ester of triterpenic acid And / or pharmacologically acceptable salts thereof can be preferably exemplified. Examples of the aliphatic hydrocarbon ester having 1 to 20 carbon atoms include methyl ester, ethyl ester, hexyl ester, cyclohexyl ester, octyl ester, isooctyl ester, lauryl ester, cetyl ester, stearyl ester, isostearyl ester, oleyl ester and the like. The aliphatic ester is preferably exemplified. Moreover, as a C1-C4 hydrocarbon ester substituted by the said aromatic group, benzyl ester, phenylethyl ester, phenylpropyl ester, phenylbutyl ester etc. can be illustrated suitably, and benzyl ester is especially preferable. Among the aforementioned anti-wrinkle agents, particularly preferred are ursolic acid and / or pharmacologically acceptable salts thereof, benzylursolic acid and / or pharmacologically acceptable salts thereof (for example, JP-A-2000-302659), ursolic acid phosphate ester and / or a pharmacologically acceptable salt thereof. The above-described anti-wrinkle agent of the present invention contains the compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof in a composition, thereby improving skin beautifying, especially wrinkle formation. The preventive or ameliorating action is enhanced.

ウルソ−ル酸ベンジル

Benzyl ursolate

ウルソ−ル酸リン酸エステル

Ursolic acid phosphate

  The anti-wrinkle agent can be synthesized by the following method, or can be purchased as a commercially available reagent. Among the above-mentioned anti-wrinkle agents, C1-C20 aliphatic hydrocarbon esters of triterpenic acid and C1-C4 hydrocarbon esters substituted with an aromatic group of triterpenic acid include the corresponding triterpenic acid. It can be obtained by treating with sodium hydride to obtain a sodium salt, and then adding a halogenated hydrocarbon to this to react. The reaction temperature and time may be one to 12 hours at room temperature or under reflux conditions. The phosphate ester of triterpenic acid can be derived from triterpenic acid, for example, according to the method described in Table No. 2006-132033. Specifically, triterpenic acid phosphate is obtained by treating commercially available triterpenic acid with 1 to 3 equivalents of dimethyl-N, N-diethyl phosphoramidate in the presence of tetrazole, It can be synthesized by reacting peroxide to form methyl phosphate of triterpenic acid and then further reacting with trimethylsilyl bromide.

  The above-mentioned anti-wrinkle agent can be used as an anti-wrinkle agent as it is, but it can also be treated with a pharmacologically acceptable acid or base, converted into a salt form, and used as a salt. For example, mineral salts such as hydrochloride, sulfate, nitrate, phosphate, carbonate, maleate, fumarate, oxalate, citrate, lactate, tartrate, methanesulfonate, para Organic acid salts such as toluene sulfonate and benzene sulfonate, alkali metals such as sodium salt and potassium salt, alkaline earth metals such as calcium salt and magnesium salt, triethylamine salt, triethanolamine salt, ammonium salt, monoethanol Preferred examples include organic amine salts such as ruamine salt and piperidine salt, and basic amino acid salts such as lysine salt and alginate.

  In addition, among the anti-wrinkle agents of the present invention, a plant extract having a dermal collagen fiber bundle restructuring action will be described. As the component having a dermal collagen fiber bundle reconstructing action of the present invention, a plant extract obtained from the Myrtaceae genus Crestaceae, a plant extract obtained from the Hypericaceae family Hypericum, a plant extract obtained from the Hypericum perforatum hypericum , A plant extract obtained from Hypericumaceae, a plant extract obtained from Hypericum spp., A plant extract obtained from Oenaceae giraffe, a plant extract obtained from Otocosi, a plant extract obtained from Rosaceae Biwa , Plant extract obtained from rosaceae peach, plant extract obtained from Chrysanthemum jujube, plant extract obtained from honeysuckle family elderberry, plant extract obtained from asteraceae cornflower, plant extract obtained from Labiatae time Thing, Lamiaceae -Plant extract obtained from Zumari, plant extract obtained from Lamiaceae sage, plant extract obtained from Lamiaceae perilla, plant extract obtained from Lamiaceae perilla, plant obtained from Labiatae Extracts and the like can be suitably exemplified, and among these, more preferable examples include plant extracts obtained from the genus Myrtaceae spp., Plant extracts obtained from Hypericum pertussis, and plant extracts obtained from Hypericum perforatum Extract, plant extract obtained from Hypericaceae, plant extract obtained from Hypericum pertussis, plant extract obtained from Honeysuckle family Elderberry, plant extract obtained from Chrysanthemum cornflower, Lamiaceae rosemary The obtained plant extract can be exemplified suitably.The component having an action of reconstructing dermal collagen fiber bundle is contained in the composition together with the compound represented by the general formula (1), its isomer and / or a pharmacologically acceptable salt thereof. By doing so, the effect of beautifying the skin, particularly, preventing or improving wrinkle formation is enhanced.

  The plant extract having a dermal collagen fiber bundle restructuring action of the present invention can be applied without particular limitation as long as it is a plant extract having a dermal collagen fiber bundle restructuring action. The plant extract in the present invention refers to a plant body itself, a processed product obtained by drying, shredding, pulverizing the plant body, a solvent extract obtained by adding a solvent to the plant body or the processed product, and an extract. It means a general term for a solvent-removed product of an extract from which a solvent has been removed, a purified product obtained by purifying such a product by column chromatography, liquid-liquid extraction or the like. Examples of the plant to be applied to the plant extract of the present invention include Ascortisaceae, Aspergillus, Aspergillus, Aspergillus, Aspergillus, Aspergillus, Aspergillus, Asperidae, Asperidae, Asperidae, Peach, buckthorn jujube, honeysuckle family elderberry, chrysanthemum cornflower, perilla family thyme, perilla family rosemary, perilla family sage, perilla family perilla, persimmon family persimmon, perilla family mint, etc. Among these, in particular, Myrtaceae genus Crestedeaceae, Hypericumaceae Hypericum, Hypericumaceae Hypericum perforatum, Hypericumaceae Giantaceae, Hypericumaceae Tomoezo, Lonicera spp. Family cornflower, Shisokaro - Zumari - is suitably be exemplified. As the plant part used for the preparation of the plant extract of the present invention, any part of the plant body can be used, but a particularly preferable one is a dried whole plant. This is because the site contains many components for reconstructing the dermal collagen fiber bundle. Further, as the plant extract of the present invention, a polar solvent extract or a solvent-removed product thereof can be particularly preferably exemplified. Examples of the polar solvent include alcohols such as ethanol and methanol, ethyl acetate and methyl formate. One or more selected from esters such as acetone, ketones such as acetone and methyl ethyl ketone, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as chloroform and methylene chloride, and water Preferred examples can be given. Of these, particularly preferred are one or more selected from water and alcohol. Such an extract or its solvent-removed product is soaked in a plant or processed product by 1 to 10 times the amount of solvent and immersed for several days at room temperature or for several hours at a temperature near the boiling point. That's fine. The solvent can be removed by evaporation to dryness, concentration under reduced pressure, or lyophilization. Most preferred are vacuum concentration and lyophilization.

  The anti-wrinkle agent of the composition of the present invention can contain only one species or two or more species. Moreover, as preferable content in the composition of this invention, it is 0.00001-15 mass%, More preferably, it is 0.0001 mass%-10 mass%, More preferably, it is 0.001 mass%-5 mass%. More preferably, the content is preferably 0.01% to 3% by weight. This is because if the amount is too small, the effect may not be exhibited, and if the amount is too large, the effect reaches a peak and the degree of freedom of prescription may be impaired.

<Manufacture example 8: The manufacturing method of the plant extract obtained from Myrtaceae cinnamon>
5 (L) of methanol is added to 500 (g) of the dried floret of Chrysantaceae, soaked at room temperature for 1 week, filtered, and concentrated under reduced pressure. A plant extract 35 (g) was obtained.

<Production Example 9: Method for producing a plant extract obtained from Hypericumaceae>
Obtained from 500 g of dried Hypericum perforatum hyperthermia, added 5 (L) methanol, soaked at room temperature for 1 week, filtered, concentrated under reduced pressure, and obtained from Hypericum pertussis of the present invention. 22 g of plant extract was obtained. According to the same procedure, a plant extract obtained from Hypericum perforaceae, a plant extract obtained from Hypericum pertussis, and a plant extract obtained from Hypericum perforatum were obtained.

<Manufacture example 10: The manufacturing method of the plant extract obtained from the honeysuckle family elderberry>
Add 10 (L) of ethanol to 1 (kg) of honeysuckle family elderberry flower, reflux for 2 hours, filter and remove the filtrate. Add this to water 3 (L) all at once and collect the deposited precipitate by filtration. The plant extract 19 (g) obtained from the honeysuckle family elderberry of this invention was obtained.

<Production Example 11: Method for producing plant extract obtained from asteraceae cornflower>
Add 10 (L) of ethanol to 1 (kg) of Asteraceae cornflower and reflux for 2 hours, filter and remove the filtrate, add it to water 3 (L) at once and collect the deposited precipitate by filtration. A plant extract 12 (g) obtained from the asteraceae cornflower of the present invention was obtained.

<Production Example 12: Method for producing plant extract obtained from Labiatae Rosemary>
10 (L) ethanol was added to rosemary-1 (kg), and the mixture was refluxed for 2 hours. The filtrate was filtrated and the filtrate was concentrated under reduced pressure to obtain crude extract 1 213 (g). 100 (g) of the crude extract 1 was dissolved in 600 (mL) of ethanol, and this was added to 200 (mL) of water all at once, and the deposited precipitate was collected by filtration to obtain 42 g of a crude extract 2. 100 (g) of the crude extract 2 was dissolved in 500 (mL) normal butanol, 500 (mL) water was added, liquid-liquid extraction was performed, and a butanol phase was obtained. This operation was repeated three times, and the butanol phases were combined and concentrated under reduced pressure to obtain a plant extract 27 (g) obtained from the Labiatae rosemary of the present invention.

<Composition of the present invention>
The composition of the present invention comprises 1) a compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent. The compound represented by the general formula (1) of the present invention and / or a pharmacologically acceptable salt thereof is included in the composition together with the anti-wrinkle agent, so that the skin beautifying action, particularly, wrinkle formation. The effect of enhancing the preventive or ameliorating action against The skin beautifying effect in the present invention means a preventive or ameliorating action against the skin aging phenomenon relating to the aesthetic appearance of the skin that becomes apparent with age, and the prevention or improving action against wrinkle formation can be suitably exemplified. In addition to an improving action that makes wrinkles less noticeable, a preventive or improving action for skin symptoms such as wrinkles and sagging that are formed and become apparent can be preferably exemplified. Of the skin beautifying effects of the composition of the present invention, specific examples of preferable skin wrinkles will improve wrinkle improvement over the comparative composition (skin external preparation) in the “wrinkle improving action evaluation of the present invention” described below. The component which shows an effect | action can illustrate suitably. In addition, the composition of the present invention has a preventive or ameliorating action against skin formation caused by pigmentation such as sunburn, spots and dullness in addition to a preventive or ameliorating action against wrinkle formation. Prevention or improvement can be expected.

  In formulating a composition comprising 1) a compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent. It can contain optional components used in formulating normal foods, pharmaceuticals, cosmetics and the like. Examples of such optional components include oral excipients such as excipients such as lactose and white sugar, binders such as starch, cellulose, gum arabic, and hydroxypropyl cellulose, carboxymethyl cellulose, Disintegrants such as sodium and carboxymethylcellulose calcium, surfactants such as soy lecithin and sucrose fatty acid ester, sweeteners such as malt and sorbitol, sour agents such as citric acid, phosphates, etc. Buffering agents, film forming agents such as shellac and zein, lubricants such as talc and wax, glidants such as light anhydrous silicic acid and dry aluminum hydroxide gel, diluents such as physiological saline and aqueous glucose solution, Suitable examples include flavoring agents, coloring agents, bactericides, preservatives, and fragrances.

  As the composition of the present invention, pharmaceuticals, cosmetics, foods, beverages and the like can be suitably exemplified, and since they can be taken on a daily basis, it is preferable to adapt to foods, cosmetics and the like. The administration route can be either oral administration or transdermal administration. For the purpose of detoxification (detox), oral administration with high efficiency in reaching the relevant organ is adopted, and forms of oral administration compositions such as foods Is preferably adopted. Moreover, when such a component is continuously administered, and further considering safety, it is preferably administered transdermally. As long as it can be applied to the skin for external use, it can be applied without particular limitation. For example, cosmetics including quasi-drugs, external preparations for skin, miscellaneous items for external use, etc. can be preferably exemplified. The external skin preparation of the present invention can be used without particular limitation as long as it is applied externally to the skin, for example, cosmetics, skin external medicine, skin external goods and the like can be suitably exemplified, It is particularly preferable to apply to cosmetics. This is because the external preparation for skin of the present invention has an unparalleled feeling of use and is particularly suitable for cosmetics where the feeling of use is important. The cosmetics are not particularly limited as long as the oil-in-water emulsifier form can be applied. For example, basic cosmetics such as essences, milky lotions, creams, under-makeups, foundations, teasers, etc. Suitable examples include makeup cosmetics such as kukara, mascara, and eyeliner, and hair cosmetics such as hair cream.

  The external preparation for skin of the present invention can contain, in addition to such components, optional components that are usually used in external preparations for skin. Such optional ingredients include, for example, macadamia nut oil, avocado oil, corn oil, olive oil, rapeseed oil, sesame oil, castor oil, safflower oil, cottonseed oil, jojoba oil, palm oil, palm oil, liquid Lanolin, hydrogenated coconut oil, hydrogenated oil, molasses, hydrogenated castor oil, beeswax, candelilla wax, carnauba wax, ibotarou, lanolin, reduced lanolin, hard lanolin, jojoba wax, oils, waxes; liquid paraffin, squalane, pristane, ozokerite, Hydrocarbons such as paraffin, ceresin, petrolatum, microcrystalline wax; higher fatty acids such as oleic acid, isostearic acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, undecylenic acid; cetyl alcohol, stearyl alcohol -Le, Isosteari Higher alcohols such as alcohol, behenyl alcohol, octyl decanol, myristyl alcohol, cetostearyl alcohol; cetyl isooctanoate, isopropyl myristate, hexyldecyl isostearate, diisopropyl adipate, sebacic acid Di-2-ethylhexyl, cetyl lactate, diisostearyl malate, ethylene glycol di-2-ethylhexanoate, neopentyl glycol dicaprate, glycerin di-2-heptylundecanoate, glycerin tri-2-ethylhexanoate Synthetic ester oils such as trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, pentane erythritol tetra-2-ethylhexanoate; dimethylpolysiloxane, methylphenylpoly Chain polysiloxanes such as Loxane and diphenylpolysiloxane; Cyclic polysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexanesiloxane; Amino-modified polysiloxane, polyether-modified polysiloxane, and alkyl-modified polysiloxane , Oil agents such as silicone oils such as modified polysiloxane such as fluorine-modified polysiloxane; anionic surfactants such as fatty acid soap (sodium laurate, sodium palmitate, etc.), potassium lauryl sulfate, triethanolamine alkyl sulfate ; Cationic surfactants such as stearyltrimethylammonium chloride, benzalkonium chloride, laurylamine oxide; imidazoline-based amphoteric surfactants (2-cocoyl-2-imida) Zolinium hydroxide-1-carboxyethyloxy disodium salt, etc.), betaine surfactants (alkyl betaine, amide betaine, sulfobetaine, etc.), and amphoteric surfactants such as acylmethyltaurine; sorbitan fatty acid esters (sorbitan) Monostearate, sorbitan sesquioleate, etc.), glycerin fatty acids (such as glyceryl monostearate), propylene glycol fatty acid esters (such as propylene glycol monostearate), hardened castor oil derivatives, glycerin alkyl ether POE sorbitan fatty acid esters (POE sorbitan monooleate, polyoxyethylene sorbitan monostearate, etc.), POE sorbite fatty acid esters (POE-sorbitol monolaurate, etc.), POE glycerin fatty acid ester Tells (POE-glycerol monoisostearate, etc.), POE fatty acid esters (polyethylene glycol monooleate, POE distearate, etc.), POE alkyl ethers (POE2-octyldodecyl ether, etc.), POE alkylphenyl ethers (POE nonylphenyl ether, etc.), Pluronic types, POE / POP alkyl ethers (POE / POP2-decyltetradecyl ether, etc.), Tetronics, POE castor oil, Hardened castor oil derivatives (POE castor oil, POE hardened castor oil, etc.), nonionic surfactants such as sucrose fatty acid ester, alkyl glucoside; moisturizing ingredients such as sodium pyrrolidone carboxylate, lactic acid, sodium lactate; surface treatment May be mica, talc, kaolin, synthetic mica, Powders such as calcium oxide, magnesium carbonate, anhydrous silicic acid (silica), aluminum oxide, barium sulfate; surface may be treated, bengara, yellow iron oxide, black iron oxide, cobalt oxide, ultramarine, bitumen Inorganic pigments such as titanium oxide and zinc oxide; surfaces may be treated; pearling agents such as titanium mica, fish phosphorus foil, bismuth oxychloride; red 202 which may be laked , Red 228, Red 226, Yellow 4, Blue 404, Yellow 5, Red 505, Red 230, Red 223, Orange 201, Red 213, Yellow 204, Yellow 203, Blue Organic dyes such as No. 1, Green No. 201, Purple No. 201, Red No. 204; Organic powders such as polyethylene powder, polymethyl methacrylate, nylon powder, organopolysiloxane elastomer; Paraaminobenzoic acid UV absorbers; Anthranilic acid UV absorbers; Salicylic acid UV absorbers; Cinnamic acid UV absorbers; Benzophenone UV absorbers; Sugar UV absorbers; 2- (2'-hydroxy- UV absorbers such as 5′-t-octylphenyl) benzotriazole and 4-methoxy-4′-t-butyldibenzoylmethane; lower alcohols such as ethanol and isopropanol; vitamin A or a derivative thereof Vitamin B6 such as vitamin B6 hydrochloride, vitamin B6 tripalmitate, vitamin B6 dioctanoate, vitamin B2 or a derivative thereof, vitamin B12, vitamin B15 or a derivative thereof; α-tocopherol, β-tocopherol, Vitamin E such as γ-tocopherol, vitamin E acetate, vitamin D, vitamin H, punt Phosphate, pantethine, vitamins pyrroloquinoline quinone such like; phenoxyethanol - antibacterial agents such as Le; hectorite, and organic-modified clay minerals such as dimethyl distearyl ammonium modified hectorite may be preferably exemplified.

  The skin external preparation of the present invention contains the essential components described above, and preferably takes the form of an emulsifier. The form of the emulsifier form may be either the water-in-oil emulsifier form or the oil-in-water emulsifier form, but the oil-in-water emulsifier form is particularly preferred. Here, the water-in-oil emulsifier form is a term collectively referred to as an emulsifier form having an oil phase in the outer phase, and may contain an aqueous phase in the inner phase or may have an emulsion such as an oil-in-water emulsion. You may do it. Similarly, the oil-in-water emulsifier form is a general term for an emulsion having an aqueous phase in the outer phase, and may have an oil phase in the inner phase or an emulsion such as a water-in-oil emulsion. good.

  The skin external preparation of the present invention can contain a non-surfactant used in skin external preparations such as ordinary cosmetics. Furthermore, it is also preferable to contain an alkyl-modified carboxyvinyl polymer and / or a salt thereof in the sense of keeping the emulsified state stable. The preferable content of such components is 0.01 to 0.5 mass%, more preferably 0.05 to 0.3 mass%, based on the total amount of the external preparation for skin. Such a component is preferably contained also in that sense because it forms a composite film with the essential ingredient amodimethicone after administration to the skin and enhances the effect of amodimethicone. Such alkyl-modified carboxyvinyl polymers include commercially available products, which can be purchased and used. Preferable commercial products are “Pemuren (registered trademark) TR-1” and “Pemuren (registered trademark)” which are commercially available from Nippon Surfactant Kogyo Co., Ltd. and are alkyl-modified with an alkyl group having 10 to 30 carbon atoms. (Trademark) TR-2 "," Carbopol (registered trademark) 1382 "commercially available from BF Goodrich (USA), and the like. There are “Carbopol (registered trademark) Ultrez 10”, “Carbopol (registered trademark) 940” and the like which are commercially available from BF Goodrich (USA). Such hydrophilic polymers may be used alone or in combination of two or more. The oil-in-water emulsion composition of the present invention preferably contains 0.05 to 1% by mass of such a hydrophilic polymer, and more preferably 0.08 to 0.5% by mass. When less than this, an emulsification system will become unstable, and when more than this, the viscosity of a system will become high too much and applicability | paintability will worsen. Further, when such an alkyl-modified carboxyvinyl polymer and / or a salt thereof is contained, a glyceryl alkyl ether or a glyceryl alkenyl ether is contained for the purpose of reinforcing the emulsion structure produced by such a polymer. It is preferable. Suitable examples of the glyceryl alkyl ether include batyl alcohol, and preferred examples of the glyceryl alkenyl ether include ceralkyl alcohol. Such ethers are preferably contained in an amount of 0.1% by mass to 1% by mass, and the content is preferably equivalent to or 5 times the content of the alkyl-modified carboxyvinyl polymer. This is because this amount range is suitable for strengthening the emulsifier form.

  Further, among the above optional components, nonionic surfactants are particularly preferable, and among them, lipophilic surfactants that are excellent in structure formation in an emulsified state are preferable. As the ionic surfactant, sorbitan stearate, glycerin monostearate and the like can be particularly preferably exemplified. The preferable content of such components is 0.1 to 5% by mass, and more preferably 0.2 to 3% by mass. By adding such a component, the adhesiveness with the skin becomes excellent.

  The external preparation for skin of the present invention can be produced by treating the above-mentioned optional components and essential components according to a conventional method.

Hereinafter, the present invention will be described in more detail with reference to examples.

<Production Example 13: Production 1 of composition of the present invention (skin external preparation)>
According to the formulations shown in Tables 1 and 2, the composition of the present invention (external preparation for skin) was prepared. That is, the components of A, B, and C are heated to 80 ° C., and after neutralizing and adding C to B, the emulsion particles are homogenized and homogenized with a homomixer. Cosmetics 1-12) were obtained. In the same manner, Comparative Example 1 in which “the compound represented by the general formula (1) of the present invention” was replaced with “water”, and Comparative Example 2 in which “the anti-wrinkle agent of the present invention” was replaced with “water” Comparative Example 3 was prepared by substituting “water” for both the “compound represented by the general formula (1) of the present invention” and the “anti-wrinkle agent of the present invention”.

<Test Example 1: Wrinkle improving action evaluation 1 of the present invention>
Using cosmetics 1 to 12 and Comparative Examples 1 to 3 prepared according to the method described in Example 1, the wrinkle improvement effect was examined according to the following method. That is, 120 panelists (women, 40-60 years old) who are worried about wrinkles on the corners of the eyes are divided into 15 groups of 8 persons, and cosmetics 1-12 and Comparative Examples 1-3 are passed to each group. The wrinkle-improving effect was examined by comparing the eye corner replicas before and after the test. The replica is a white one that does not transmit light, and the surface shape of the skin is transferred to this, and this replica is fixed to the sample stage of the stereomicroscope, irradiated with light at an angle of 45 degrees, and the replica is rotated, A shadow image (1 × 1 cm ² ) in the direction in which the shadow of the skin groove is strongly observed was taken into the image analysis apparatus. According to the wrinkles, the image has low brightness at deep wrinkles and high brightness at no wrinkles, forming a shadow. The luminance distribution in the shadow image is obtained, and with the median value of the luminance as a boundary, the bright spot with the luminance higher than the median value is converted to the maximum luminance, and the bright spot with the luminance less than the median value is converted to the luminance 0, and binarization is performed. The area ratio of the shaded portion (the portion with 0 luminance) was obtained. The wrinkle improvement degree (%) was determined by (area ratio of shadow before test−area ratio of shadow after test) / (area ratio of shadow before test) × 100. The results are shown in Table 3 as the average value ± standard deviation of 8 people in each group. From the results of Table 3, it can be seen that the cosmetics 1 to 12 of the present invention have an excellent wrinkle improving action.

<Manufacture example 14: Manufacturing method 2 of the skin external preparation of this invention>
Regarding the cosmetic 9 described in Example 1, “the compound represented by the general formula (1) of the present invention (Compound 12)” and “the anti-wrinkle agent of the present invention (ursolic acid phosphate ester)” Cosmetics 13 to 16 having the concentrations changed to those shown in Table 4 were prepared. The mass% changed by the increase / decrease of the component was adjusted by changing the mass% of “water” in the component of the external preparation for skin.

<Test Example 2: Wrinkle improving action evaluation 2 of the present invention>
The wrinkle-improving action was evaluated according to the evaluation method described in Example 2 on cosmetics 5 described in Example 1, cosmetics 13 to 16 having the formulation components described in Comparative Example 3, and Example 3. The results are shown in Table 5. From the results in Table 5, it can be seen that the cosmetic 5 and the cosmetics 13 to 15 of the present invention have an excellent wrinkle improving effect.

<Production Example 9: Method 3 for producing skin external preparation of the present invention>
An attempt was made to prepare cosmetic 17 in which “Pemlen TR-2” was replaced with POE (25) stearic acid in the ingredients of cosmetic 5 described in Example 1, and cosmetic 25 was separated immediately after production. Thus, an emulsion was not obtained.

<Production Example 10: Production of health food of the present invention>
Health foods (health foods 1 to 8) were prepared according to the formulations shown in Tables 6 and 7. That is, the prescription ingredients were tumbled phase granulated with 10 parts by weight of water (“New Malmerizer” manufactured by Fuji Powder Co., Ltd.) and tableted to obtain a tablet-like health food. In addition, the unit of the numerical value in a table | surface represents a weight part. This health food had an excellent wrinkle improving action.

  The composition of the present invention can be applied to wrinkle-improving cosmetics, foods, and the like.

Claims (30)

1. A composition comprising 1) a compound represented by the following general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent.

(1)
[Wherein, A represents a di- or tri-aromatic methyl group independently selected from the group consisting of an unsubstituted or substituted aryl group and / or an unsubstituted or substituted heteroaromatic ring. , B represents a cyclic or acyclic aliphatic or aromatic hydrocarbon group in which the bonding site to A is a hetero atom, and a hydrogen atom, a hydrogen atom, or a carbon atom may be substituted with a hetero atom. ] The compound represented by the general formula (1) is a compound represented by the following general formula (2) and / or a pharmaceutically acceptable salt thereof. Composition.

(2)
[In the formula, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, and B is a hetero atom at the bonding site with A. It represents a cyclic or acyclic aliphatic or aromatic hydrocarbon group in which a hydrogen atom, a hydrogen atom or a carbon atom may be substituted with a hetero atom. ] The compound represented by the general formula (2) is a compound represented by the following general formula (3) and / or a pharmaceutically acceptable salt thereof. A composition according to 1.

(3)
[In the formula, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents a nitrogen atom or NH group, and R1 represents A hydrogen atom, a hydrogen atom, or a C 3-8 cyclic aliphatic hydrocarbon group that may be substituted with a hetero atom, and the ring of the cyclic aliphatic hydrocarbon group is the other end of R 1 Includes a ring formed by re-bonding to X. ] The compound represented by the general formula (2) is a compound represented by the following general formula (4) and / or a pharmacologically acceptable salt thereof. A composition according to 1.

(4)
[Wherein, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents an oxygen atom, R2 represents a hydrogen atom, It represents a C1-C8 aliphatic hydrocarbon in which a hydrogen atom or a carbon atom may be substituted with a hetero atom. ] The compound represented by the general formula (2) is a compound represented by the following general formula (5) and / or a pharmaceutically acceptable salt thereof. A composition according to 1.

(5)
[Wherein, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents a nitrogen atom, and R3 and R4 each represent Independently, the C1-C8 aliphatic hydrocarbon in which the hydrogen atom, the hydrogen atom, or the carbon atom may be substituted by the hetero atom is represented. ] The compound represented by the general formula (2) is a compound represented by the following general formula (6) and / or a pharmaceutically acceptable salt thereof. A composition according to 1.

(6)
[Wherein, A represents a di- or triarylmethyl group independently selected from the group consisting of unsubstituted or substituted aryl groups, X represents a nitrogen atom or NH group, and R5 represents A hydrogen atom or a C3-C8 aromatic hydrocarbon group in which a carbon atom may be substituted with a hetero atom is represented, and the aromatic hydrocarbon group includes a group in which X is present in the ring. ] The compounds represented by the general formulas (1) to (6) are 1- (diphenylmethyl) imidazole (compound 1), 1- (triphenylmethyl) imidazole (compound 2), 2-[( Diphenylmethyl) oxy] ethanol (compound 3), 2-[(triphenylmethyl) oxy] ethanol (compound 4), 2-[(diphenylmethyl) amino] ethanol (compound 5), 2- [(Triphenylmethyl) amino] ethanol (Compound 6), 2-[(Diphenylmethyl) oxy] ethylamine (Compound 7), 2-[(Triphenylmethyl) oxy] ethylamine (Compound 8), 1- ( Diphenylmethyl) pyrrolidine (compound 9), 1- (triphenylmethyl) pyrrolidine (compound 10), 1- (diphenylmethyl) piperidine (compound 11), 1- (triphenylmethyl) pi It consists of 1 type, or 2 or more types chosen from lysine (compound 12) and / or their pharmacologically acceptable salt, The composition as described in any one of Claims 1-6 characterized by the above-mentioned. .

1- (Diphenylmethyl) imidazole (Compound 1)

1- (triphenylmethyl) imidazole (compound 2),

2-[(Diphenylmethyl) oxy] ethanol (Compound 3)

2-[(Triphenylmethyl) oxy] ethanol (compound 4)

2-[(Diphenylmethyl) amino] ethanol (Compound 5)

2-[(Triphenylmethyl) amino] ethanol (Compound 6)

2-[(Diphenylmethyl) oxy] ethylamine (Compound 7)

2-[(Triphenylmethyl) oxy] ethylamine (Compound 8)

1- (Diphenylmethyl) pyrrolidine (Compound 9)

1- (Triphenylmethyl) pyrrolidine (Compound 10)

1- (Diphenylmethyl) piperidine (Compound 11)

1- (Triphenylmethyl) piperidine (Compound 12) The compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof is contained in an amount of 0.001% by mass to 10% by mass with respect to the total amount of the composition. Item 8. The composition according to any one of Items 1 to 7. The anti-wrinkle agent is vitamin A, a derivative thereof and / or a pharmacologically acceptable salt thereof, triterpenic acid, a derivative thereof and / or a pharmacologically acceptable salt thereof, The composition as described in any one of Claims 1-8. 1 type or 2 types in which said vitamin A or its derivative (s) is selected from retinal, retinal, retinoic acid, tretinoin, isotretinoin, retinoic acid tocopherol, retinoic palmitate, retinoic acetate It is the above, The composition as described in any one of Claims 1-9 characterized by the above-mentioned. The composition according to any one of claims 1 to 9, wherein the triterpenic acid residue of the triterpenic acid or a derivative thereof is ursolic acid, betulinic acid or a residue of those acids. object. The composition according to any one of claims 1 to 9, wherein the triterpenic acid or a derivative thereof is triterpenic acid, triterpenic acid benzyl ester, or triterpenic acid phosphoric ester. The composition according to any one of claims 1 to 9, wherein the anti-wrinkle agent is a plant extract having a dermal collagen fiber bundle reconstructing action. The plant extract having the dermal collagen fiber bundle restructuring action is one or more selected from the following plant extracts, The composition as described.
<Plant extract having dermal collagen fiber bundle restructuring action>
A plant extract obtained from the Myrtaceae spp. Extracts, plant extracts obtained from honeysuckle, elderberry, plant extracts obtained from Asteraceae cornflower, plant extracts obtained from Lamiaceae rosemary The said anti-wrinkle agent contains 0.00001 mass%-15 mass% with respect to the composition whole quantity, The composition as described in any one of Claims 1-14 characterized by the above-mentioned. The composition according to any one of claims 1 to 15, wherein the composition is a cosmetic (however, including a quasi-drug). It is an object for beautiful skin, The composition as described in any one of Claims 1-16 characterized by the above-mentioned. The composition according to any one of claims 1 to 17, which is used for prevention or improvement of wrinkle formation. It is a skin external preparation, The composition as described in any one of Claims 1-17 characterized by the above-mentioned. A skin external preparation characterized by comprising 1) a compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof, and 2) an anti-wrinkle agent. The compound represented by the general formula (1) is a compound represented by the general formula (3) and / or a pharmacologically acceptable salt thereof. Topical skin preparation. The compound represented by the general formula (1) is 1- (diphenylmethyl) imidazole (compound 1), 1- (triphenylmethyl) imidazole (compound 2), 2-[(diphenylmethyl) oxy. ] Ethanol (compound 3), 2-[(triphenylmethyl) oxy] ethanol (compound 4), 2-[(diphenylmethyl) amino] ethanol (compound 5), 2-[(triphenyl) Methyl) amino] ethanol (compound 6), 2-[(diphenylmethyl) oxy] ethylamine (compound 7), 2-[(triphenylmethyl) oxy] ethylamine (compound 8), 1- (diphenylmethyl) pyrrolidine (Compound 9), 1- (Triphenylmethyl) pyrrolidine (Compound 10), 1- (Diphenylmethyl) piperidine (Compound 11), 1- (Triphenylmethyl) piperidine Compound 12) and / or, characterized in that their pharmacologically acceptable salts, skin external preparation according to claim 20 or 21. The anti-wrinkle agent is vitamin A, a derivative thereof and / or a pharmacologically acceptable salt thereof, triterpenic acid, a derivative thereof and / or a pharmacologically acceptable salt thereof, The skin external preparation as described in any one of Claims 20-22. 1 type or 2 types in which said vitamin A or its derivative (s) is selected from retinal, retinal, retinoic acid, tretinoin, isotretinoin, retinoic acid tocopherol, retinoic palmitate, retinoic acetate It is the above, The skin external preparation as described in any one of Claims 20-23 characterized by the above-mentioned. 24. The skin according to any one of claims 20 to 23, wherein the triterpenic acid residue of the triterpenic acid or a derivative thereof is ursolic acid, betulinic acid or a residue of those acids. Topical agent. The skin external preparation according to any one of claims 20 to 23 and 25, wherein the triterpenic acid or a derivative thereof is triterpenic acid, triterpenic acid benzyl ester, or triterpenic acid phosphoric ester. The external preparation for skin according to any one of claims 20 to 23, wherein the anti-wrinkle agent is a plant extract having a dermal collagen fiber bundle reconstructing action. The plant extract having the dermal collagen fiber bundle reconstructing action is one or more selected from the following plant extracts, according to claim 20 to 23, 27 The skin external preparation as described.
<Plant extract having dermal collagen fiber bundle restructuring action>
A plant extract obtained from the Myrtaceae spp. Extracts, plant extracts obtained from honeysuckle, elderberry, plant extracts obtained from Asteraceae cornflower, plant extracts obtained from Lamiaceae rosemary It is an oil-in-water emulsifier form, The skin external preparation as described in any one of Claims 20-28 characterized by the above-mentioned. Furthermore, the skin external preparation as described in any one of Claims 20-29 characterized by including a preferable formulation component.