JP2012001520A - Composition - Google Patents
Composition Download PDFInfo
- Publication number
- JP2012001520A JP2012001520A JP2010140429A JP2010140429A JP2012001520A JP 2012001520 A JP2012001520 A JP 2012001520A JP 2010140429 A JP2010140429 A JP 2010140429A JP 2010140429 A JP2010140429 A JP 2010140429A JP 2012001520 A JP2012001520 A JP 2012001520A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- ethanol
- diphenylmethyl
- triphenylmethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 102
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 150000003839 salts Chemical class 0.000 claims abstract description 102
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 70
- 230000001153 anti-wrinkle effect Effects 0.000 claims abstract description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 65
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 54
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 42
- 239000002537 cosmetic Substances 0.000 claims abstract description 34
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 24
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 229940079593 drug Drugs 0.000 claims abstract description 7
- -1 benzyl ester Chemical class 0.000 claims description 441
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 127
- 239000000419 plant extract Substances 0.000 claims description 83
- 230000009471 action Effects 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 57
- 238000002360 preparation method Methods 0.000 claims description 43
- 230000037373 wrinkle formation Effects 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 239000000835 fiber Substances 0.000 claims description 27
- 229960001727 tretinoin Drugs 0.000 claims description 27
- 102000008186 Collagen Human genes 0.000 claims description 26
- 108010035532 Collagen Proteins 0.000 claims description 26
- 229920001436 collagen Polymers 0.000 claims description 26
- 125000003107 substituted aryl group Chemical group 0.000 claims description 26
- 230000002500 effect on skin Effects 0.000 claims description 25
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 23
- 230000006872 improvement Effects 0.000 claims description 22
- 229930002330 retinoic acid Natural products 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 125000005039 triarylmethyl group Chemical group 0.000 claims description 18
- TXLIAXQCAUHQEE-UHFFFAOYSA-N 2-trityloxyethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCN)C1=CC=CC=C1 TXLIAXQCAUHQEE-UHFFFAOYSA-N 0.000 claims description 17
- GHSBJDZSBNDAGL-UHFFFAOYSA-N 2-(tritylamino)ethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCCO)C1=CC=CC=C1 GHSBJDZSBNDAGL-UHFFFAOYSA-N 0.000 claims description 16
- IUCHRJJXIZKLTA-UHFFFAOYSA-N 2-trityloxyethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCO)C1=CC=CC=C1 IUCHRJJXIZKLTA-UHFFFAOYSA-N 0.000 claims description 16
- 230000002265 prevention Effects 0.000 claims description 16
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 15
- DJMXWKUBTGMKCG-UHFFFAOYSA-N 1-benzhydrylpyrrolidine Chemical compound C1CCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 DJMXWKUBTGMKCG-UHFFFAOYSA-N 0.000 claims description 15
- NFJFUDGBWGXTHS-UHFFFAOYSA-N 2-benzhydryloxyethanamine Chemical compound C=1C=CC=CC=1C(OCCN)C1=CC=CC=C1 NFJFUDGBWGXTHS-UHFFFAOYSA-N 0.000 claims description 15
- 229940125797 compound 12 Drugs 0.000 claims description 15
- 229940125904 compound 1 Drugs 0.000 claims description 14
- 229940125773 compound 10 Drugs 0.000 claims description 14
- 229940125782 compound 2 Drugs 0.000 claims description 14
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 14
- 230000002207 retinal effect Effects 0.000 claims description 14
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 13
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 13
- 229940126214 compound 3 Drugs 0.000 claims description 13
- 229940125898 compound 5 Drugs 0.000 claims description 13
- 239000000284 extract Substances 0.000 claims description 13
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 12
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 12
- 239000003995 emulsifying agent Substances 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 235000019155 vitamin A Nutrition 0.000 claims description 12
- 239000011719 vitamin A Substances 0.000 claims description 12
- 229940045997 vitamin a Drugs 0.000 claims description 12
- MAZMHPQDNYKCOI-UHFFFAOYSA-N 1-benzhydrylimidazole Chemical compound C1=NC=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 MAZMHPQDNYKCOI-UHFFFAOYSA-N 0.000 claims description 11
- LLOQMFDCQPKSFB-UHFFFAOYSA-N 1-benzhydrylpiperidine Chemical compound C1CCCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LLOQMFDCQPKSFB-UHFFFAOYSA-N 0.000 claims description 11
- NPZDCTUDQYGYQD-UHFFFAOYSA-N 1-tritylimidazole Chemical compound C1=NC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NPZDCTUDQYGYQD-UHFFFAOYSA-N 0.000 claims description 11
- DVFDHIZVAQOEMX-UHFFFAOYSA-N 1-tritylpyrrolidine Chemical compound C1CCCN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DVFDHIZVAQOEMX-UHFFFAOYSA-N 0.000 claims description 11
- DAXRGSDCXVUHEW-UHFFFAOYSA-N 2-(benzhydrylamino)ethanol Chemical compound C=1C=CC=CC=1C(NCCO)C1=CC=CC=C1 DAXRGSDCXVUHEW-UHFFFAOYSA-N 0.000 claims description 11
- 240000004385 Centaurea cyanus Species 0.000 claims description 11
- 241000207923 Lamiaceae Species 0.000 claims description 11
- 241000208829 Sambucus Species 0.000 claims description 10
- 235000018735 Sambucus canadensis Nutrition 0.000 claims description 10
- 235000007123 blue elder Nutrition 0.000 claims description 10
- 235000007124 elderberry Nutrition 0.000 claims description 10
- 235000008995 european elder Nutrition 0.000 claims description 10
- NCYCYZXNIZJOKI-OVSJKPMPSA-N retinal group Chemical group C\C(=C/C=O)\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 claims description 10
- 229940096998 ursolic acid Drugs 0.000 claims description 10
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims description 10
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 8
- ZDTBBCYZMFEIHU-UHFFFAOYSA-N 1-tritylpiperidine Chemical compound C1CCCCN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZDTBBCYZMFEIHU-UHFFFAOYSA-N 0.000 claims description 8
- 241000219926 Myrtaceae Species 0.000 claims description 8
- 244000178231 Rosmarinus officinalis Species 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 8
- JSYRPEKHRQJXQK-UHFFFAOYSA-N 2-benzhydryloxyethanol Chemical compound C=1C=CC=CC=1C(OCCO)C1=CC=CC=C1 JSYRPEKHRQJXQK-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 6
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 6
- QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 claims description 5
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 claims description 5
- DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 claims description 5
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 claims description 5
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 claims description 5
- PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 5
- 229960005280 isotretinoin Drugs 0.000 claims description 5
- MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229930003799 tocopherol Natural products 0.000 claims description 4
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- 229960001295 tocopherol Drugs 0.000 claims description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 241000205585 Aquilegia canadensis Species 0.000 claims 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 239000003860 topical agent Substances 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 230000003750 conditioning effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 45
- 230000000694 effects Effects 0.000 description 43
- 238000004519 manufacturing process Methods 0.000 description 34
- 206010040954 Skin wrinkling Diseases 0.000 description 32
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- 125000003944 tolyl group Chemical group 0.000 description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 20
- 125000006267 biphenyl group Chemical group 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- 125000001207 fluorophenyl group Chemical group 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 13
- 230000003449 preventive effect Effects 0.000 description 13
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- 125000003118 aryl group Chemical group 0.000 description 12
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- 125000001624 naphthyl group Chemical group 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
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- 230000002829 reductive effect Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
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- 229910019142 PO4 Inorganic materials 0.000 description 10
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 10
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
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- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 9
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- 235000013402 health food Nutrition 0.000 description 5
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004166 Lanolin Substances 0.000 description 4
- 201000005702 Pertussis Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000287 crude extract Substances 0.000 description 4
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Landscapes
- Cosmetics (AREA)
Abstract
Description
本発明は、化粧料(但し、医薬部外品を含む)、食品等に好適な組成物に関し、詳しくは、1)下記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤とを含有することを特徴とする、組成物に関する。 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.
[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。]
[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. ]
他人による見た目の印象に大きな影響を与えるシワ、しみ、たるみ等の皮膚症状は、遺伝的な要因に加え、温度変化や紫外線暴露などの長年に渡る物理的刺激の蓄積により、加齢と共に顕在化する。特に、シワ、たるみは、他人が見た目の若々しさを判断するのに大きな要素となるために、シワやたるみを予防又は改善するために様々な方法が試されている。この様な方法には、美容的な方法としては、マッサ−ジ施術などの物理的な刺激による方法、ヒアルロン酸注入等の医療的な方法等が知られているが、十分な効果が得られないことが存するほかに、費用が高額であったり、施術上のトラブル等が存したりするため、効果を期待する人にとって必ずしも身近で有効な方法とは言い難い。一方、シワ形成の予防又は改善作用、抗老化作用を有する成分を配合した化粧料等が数多く市販されているが、これらにおいても、効果が不明瞭であったりする場合も多く存する。このため、シワ形成に対する予防又は改善効果を有する成分、並びに、前記成分が有する抗シワ、抗老化効果を増強させる技術が切望されている。 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.
前述の通り、皮膚老化現象、取り分け、シワ形成に対する予防又は改善に対する注目は、非常に高い。このため、シワ形成の作用機序の解析、更には、解明された作用機序に関する情報を基にした抗シワ剤の開発が盛んに行われている。シワ形成の作用機序としては、紫外線暴露などによる細胞の損傷とそれによって亢進される細胞のアポト−シス、マトリックスメタロプロテア−ゼ(MMP)等のプロテア−ゼの発現の亢進によるコラ−ゲン等の線維成分の加水分解、さらには、サイトカインの亢進による線維束の崩壊等が既に報告されている。この様な作用機序解析による情報を基に、抗シワ剤が数多く開発されている。シワ形成の予防又は改善作用を有する成分として有名なレチノイン酸(例えば、非特許文献1を参照)は、米国においてシワ、にきびの治療医薬品として認可されており、実効性も照明されている。しかしながら、レチノイン酸には、皮膚への刺激をはじめとする安全性面に大きな課題が存するため、日本においては、認可されていない。また、レチノイン酸以外のシワ形成に対する予防抗又は改善作用を有する成分としては、抗シワ剤(例えば、特許文献1を参照)、コラ−ゲン産生促進剤(例えば、特許文献2を参照)、ヒアルロン酸産生促進剤(例えば、特許文献3を参照)等が知られている。また、トリテルペン酸、又は、そのベンジル誘導体に付いては、光照射により生じる真皮コラ−ゲン線維束の崩壊に起因するシワに対して、当該真皮コラ−ゲン線維束構造を再構築し、改善効果を示すことが知られている(例えば、特許文献4を参照)。しかしながら、前記の抗シワ剤は、安全性、安定性に関す課題に加え、溶解性による製剤化への制限などが存する。また、かかる抗シワ剤には、十分な予防又は改善効果が得られない場合も存するため、新たな抗シワ剤の創出に加え、更には、既存の抗シワ剤の効果を増強させる成分、製剤技術の開発が望まれている。 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.
立体的に嵩高い芳香族基又は複素芳香族基(特に、ジフェニルメチル基またはトリフェニルメチル基)は、有機低分子化合物、ペプチド及び核酸合成における水酸基またはアミノ基の有効な保護基として広く知られている(例えば、非特許文献2及び非特許文献3を参照)。これらの保護基を利用した反応及び中間化合物(例えば、非特許文献4及び非特許文献5を参照)は、実験室から工業生産までの幅広いスケ−ルにおける有機合成に応用されている。また、その化学構造中に、前述の立体的に嵩高い置換基を有する化合物に関しては、抗腫瘍活性(例えば、非特許文献4を参照)、抗真菌作用(例えば、特許文献5を参照)、抗ヒスタミン作用(例えば、非特許文献5を参照)、ドパミン取り込み阻害作用(例えば、非特許文献6を参照)、カルシウム拮抗作用(例えば、非特許文献7を参照)等の生物活性を示すことが報告されている。しかしながら、前記一般式(1)に表される化合物を、抗シワ剤と共に組成物中に含有させることにより美肌作用、取り分け、シワ形成に対する予防又は改善作用が増強されることは全く知られていなかった。
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.
本発明は、この様な状況下において為されたものであり、化粧料(但し、医薬部外品を含む)、食品等に好適な組成物、具体的には、1)下記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤とを含有する組成物を提供することを課題とする。
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.
この様な状況を鑑みて、発明者等は、美肌用、取り分け、シワ形成に対する予防又は改善用に好適な、皮膚外用剤などの組成物を求め、鋭意努力を重ねた結果、1)前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤とを含有することを特徴とする組成物に、その様な特性が備わっていることを見出し、本発明を完成させるに至った。即ち、本発明は、以下に示す通りである。
<1> 1)下記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤とを含有することを特徴とする、組成物。
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.
[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。]
[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> 前記一般式(1)に表される化合物が、下記一般式(2)に表される化合物及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<1>に記載の組成物。 <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>.
[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。]
[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> 前記一般式(2)に表される化合物が、下記一般式(3)に表される化合物及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<1>又は<2>に記載の組成物。 <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>.
[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。]
[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> 前記一般式(2)に表される化合物が、下記一般式(4)に表される化合物及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<1>又は<2>に記載の組成物。 <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>.
[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。]
[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> 前記一般式(2)に表される化合物が、下記一般式(5)に表される化合物及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<1>又は<2>に記載の組成物。 <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>.
[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。]
[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> 前記一般式(2)に表される化合物が、下記一般式(6)に表される化合物及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<1>又は<2>に記載の組成物。 <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>.
[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。]
[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> 前記一般式(1)〜(6)に表される化合物が、1−(ジフェニルメチル)イミダゾ−ル(化合物1)、1−(トリフェニルメチル)イミダゾ−ル(化合物2)、2−[(ジフェニルメチル)オキシ]エタノ−ル(化合物3)、2−[(トリフェニルメチル)オキシ]エタノ−ル(化合物4)、2−[(ジフェニルメチル)アミノ]エタノ−ル(化合物5)、2−[(トリフェニルメチル)アミノ]エタノ−ル(化合物6)、2−[(ジフェニルメチル)オキシ]エチルアミン(化合物7)、2−[(トリフェニルメチル)オキシ]エチルアミン(化合物8)、1−(ジフェニルメチル)ピロリジン(化合物9)、1−(トリフェニルメチル)ピロリジン(化合物10)、1−(ジフェニルメチル)ピペリジン(化合物11)、1−(トリフェニルメチル)ピペリジン(化合物12)及び/又はそれらの薬理学的に許容される塩から選ばれる1種又は2種以上よりなることを特徴とする、<1>〜<6>の何れか一項に記載の組成物。 <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.
<8> 前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩が、組成物全量に対し、0.001質量%〜10質量%含有することを特徴とする、<1>〜<7>の何れか一項に記載の組成物。
<9> 前記抗シワ剤が、ビタミンA、その誘導体及び/又はそれらの薬理学的に許容される塩、トリテルペン酸、その誘導体及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<1>〜<8>の何れか一項に記載の組成物。
<10> 前記のビタミンA又はその誘導体が、レチノ−ル、レチナ−ル、レチノイン酸、トレチノイン、イソトレチノイン、レチノイン酸トコフェロ−ル、パルミチン酸レチノ−ル、酢酸レチノ−ルより選択される1種又は2種以上であることを特徴とする、<1>〜<9>の何れか一項に記載の組成物。
<11> 前記のトリテルペン酸又はその誘導体のトリテルペン酸残基が、ウルソ−ル酸、ベツリン酸又はそれらの酸の残基であることを特徴とする、<1>〜<9>の何れか一項に記載の組成物。
<12> 前記のトリテルペン酸又はその誘導体が、トリテルペン酸、トリテルペン酸ベンジルエステル、トリテルペン酸リン酸エステルであることを特徴とする、<1>〜<9>、<11>の何れか一項に記載の組成物。
<13> 前記抗シワ剤が、真皮コラ−ゲン線維束再構築作用を有する植物抽出物であることを特徴とする、<1>〜<9>の何れか一項に記載の組成物。
<14> 前記の真皮コラ−ゲン線維束再構築作用を有する植物抽出物が、下記に示す植物抽出物より選択される1種また2種以上であることを特徴とする、<1>〜<9>、<13>に記載の組成物。
<真皮コラ−ゲン線維束再構築作用を有する植物抽出物>
フトモモ科フトモモ属チョウジノキより得られる植物抽出物、オトギリソウ科オトギリソウより得られる植物抽出物、オトギリソウ科セイヨウオトギリソウより得られる植物抽出物、オトギリソウ科ヒメオトギリより得られる植物抽出物、オトギリソウ科トモエソウより得られる植物抽出物、スイカズラ科セイヨウニワトコより得られる植物抽出物、キク科ヤグルマギクより得られる植物抽出物、シソ科ロ−ズマリ−より得られる植物抽出物
<15> 前記抗シワ剤が、組成物全量に対し0.00001質量%〜15質量%含有することを特徴とする、<1>〜<14>の何れか一項に記載の組成物。
<16> 化粧料(但し、医薬部外品を含む)であることを特徴とする、<1>〜<15>の何れか一項に記載の組成物。
<17> 美肌用であることを特徴とする、<1>〜<16>の何れか一項に記載の組成物。
<18> シワ形成に対する予防又は改善用であることを特徴とする、<1>〜<17>の何れか一項に記載の組成物。
<19> 皮膚外用剤であることを特徴とする、<1>〜<17>の何れか一項に記載の組成物。
<20> 1)前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤とを含有することを特徴とする、皮膚外用剤。
<21> 前記一般式(1)に表される化合物が、前記一般式(3)に表される化合物及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<20>に記載の皮膚外用剤。
<22> 前記一般式(1)に表される化合物が、1−(ジフェニルメチル)イミダゾ−ル(化合物1)、1−(トリフェニルメチル)イミダゾ−ル(化合物2)、2−[(ジフェニルメチル)オキシ]エタノ−ル(化合物3)、2−[(トリフェニルメチル)オキシ]エタノ−ル(化合物4)、2−[(ジフェニルメチル)アミノ]エタノ−ル(化合物5)、2−[(トリフェニルメチル)アミノ]エタノ−ル(化合物6)、2−[(ジフェニルメチル)オキシ]エチルアミン(化合物7)、2−[(トリフェニルメチル)オキシ]エチルアミン(化合物8)、1−(ジフェニルメチル)ピロリジン(化合物9)、1−(トリフェニルメチル)ピロリジン(化合物10)、1−(ジフェニルメチル)ピペリジン(化合物11)、1−(トリフェニルメチル)ピペリジン(化合物12)及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<20>又は<21>に記載の皮膚外用剤。
<23> 前記抗シワ剤が、ビタミンA、その誘導体及び/又はそれらの薬理学的に許容される塩、トリテルペン酸、その誘導体及び/又はそれらの薬理学的に許容される塩であることを特徴とする、<20>〜<22>の何か一項に記載の皮膚外用剤。
<24> 前記のビタミンA又はその誘導体が、レチノ−ル、レチナ−ル、レチノイン酸、トレチノイン、イソトレチノイン、レチノイン酸トコフェロ−ル、パルミチン酸レチノ−ル、酢酸レチノ−ルより選択される1種又は2種以上であることを特徴とする、<20>〜<23>の何れか一項に記載の皮膚外用剤。
<25> 前記のトリテルペン酸又はその誘導体のトリテルペン酸残基が、ウルソ−ル酸、ベツリン酸又はそれらの酸の残基であることを特徴とする、<20>〜<23>の何れか一項に記載の皮膚外用剤。
<26> 前記のトリテルペン酸又はその誘導体が、トリテルペン酸、トリテルペン酸ベンジルエステル、トリテルペン酸リン酸エステルであることを特徴とする、<20>〜<23>、<25>の何れか一項に記載の皮膚外用剤。
<27> 前記抗シワ剤が、真皮コラ−ゲン線維束再構築作用を有する植物抽出物であることを特徴とする、<20>〜<23>の何れか一項に記載の皮膚外用剤。
<28> 前記の真皮コラ−ゲン線維束再構築作用を有する植物抽出物が、下記に示す植物抽出物より選択される1種また2種以上であることを特徴とする、<20>〜<23>、<27>に記載の皮膚外用剤。
<真皮コラ−ゲン線維束再構築作用を有する植物抽出物>
フトモモ科フトモモ属チョウジノキより得られる植物抽出物、オトギリソウ科オトギリソウより得られる植物抽出物、オトギリソウ科セイヨウオトギリソウより得られる植物抽出物、オトギリソウ科ヒメオトギリより得られる植物抽出物、オトギリソウ科トモエソウより得られる植物抽出物、スイカズラ科セイヨウニワトコより得られる植物抽出物、キク科ヤグルマギクより得られる植物抽出物、シソ科ロ−ズマリ−より得られる植物抽出物
<29> 水中油乳化剤形であることを特徴とする、<20>〜<28>の何れか一項に記載の皮膚外用剤。
<30> 更に、好ましい製剤成分を含有することを特徴とする、<20>〜<29>の何れか一項に記載の皮膚外用剤。
<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.
本発明によれば、美肌用、取り分け、シワ形成に対する予防又は改善用に好適な、皮膚外用剤などの組成物を提供することが出来る。
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.
<本発明の前記一般式(1)に表される化合物>
本発明の組成物は、前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤とを含有することを特徴とする。本発明の前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩は、後述する抗シワ剤と共に組成物に含有させることにより、優れた美肌作用、取り分け、シワ形成に対する予防又は改善作用を発揮する。本発明の組成物が有する美肌作用とは、年齢と共に顕在化する肌の美観に関する皮膚老化現象に対する予防又は改善作用を意味し、シワ形成に対する予防又は改善作用などが好適に例示出来る。また、前記のシワ形成に対する予防又は改善作用は、既に形成されたシワを目立たなくする改善作用などに加え、これから形成され顕在化するシワ、たるみなどの皮膚症状に対する予防又は改善作用を意味する。さらに、当該成分には、シワ形成に対する予防又は改善作用に加え、日焼け、シミ、くすみ等の色素沈着に起因する肌症状に対する予防又は改善作用等による総合的な肌状態を予防又は改善作用を有する。
<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. .
ここで前記一般式(1)に表される化合物に付いて述べれば、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。前記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、前記Aにおける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基に関し、好ましいものを具体に挙げれば、フェニル基、ナフチル基、ビフェニル基、ピリジル基、フリル基、チエニル基、チアゾリル基、イミダゾ−ル基、メチルフェニル基、エチルフェニル基、プロピルフェニル基、メトキシフェニル基、エトキシフェニル基、プロピルオキシフェニル基、ヒドロキシフェニル基、アミノフェニル基、N−メチルアミノフェニル基、N−エチルアミノフェニル基、N−プロピルアミノフェニル基、N,N−ジメチルアミノフェニル基、N,N−ジエチルアミノフェニル基、N,N−ジプロピルアミノフェニル基、フルオロフェニル基、ジフルオロフェニル基、トリフルオロメチルフェニル基、クロロフェニル基、ブロモフェニル基、メチルピリジル基、エチルピリジル基、プロピルピリジル基、メトキシピリジル基、エトキシピリジル基、プロピルオキシピリジル基、ヒドロキシピリジル基、アミノピリジル基、N−メチルアミノピリジル基、N−エチルアミノピリジル基、N−プロピルアミノピリジル基、N,N−ジメチルアミノピリジル基、N,N−ジエチルアミノピリジル基、N,N−ジプロピルアミノピリジル基、フルオロピリジル基、ジフルオロピリジル基、トリフルオロメチルピリジル基、クロロピリジル基、ブロモピリジル基、メチルナフチル基、エチルナフチル基、プロピルナフチル基、メトキシナフチル基、エトキシナフチル基、プロピルオキシナフチル基、ヒドロキシナフチル基、アミノナフチル基、N−メチルアミノナフチル基、N−エチルアミノナフチル基、N−プロピルアミノナフチル基、N,N−ジメチルアミノナフチル基、N,N−ジエチルアミノナフチル基、N,N−ジプロピルアミノナフチル基、フルオロナフチル基、ジフルオロナフチル基、トリフルオロメチルナフチル基、クロロナフチル基、ブロモナフチル基、イミダゾ−ル基、メチルイミダゾ−ル基、エチルイミダゾ−ル基、プロピルイミダゾ−ル基、メトキシイミダゾ−ル基、エトキシイミダゾ−ル基、プロピルオキシイミダゾ−ル基、ヒドロキシイミダゾ−ル基、アミノイミダゾ−ル基、N−メチルアミノイミダゾ−ル基、N−エチルアミノイミダゾ−ル基、N−プロピルアミノイミダゾ−ル基、N,N−ジメチルアミノイミダゾ−ル基、N,N−ジエチルアミノイミダゾ−ル基、N,N−ジプロピルアミノイミダゾ−ル基、フルオロイミダゾ−ル基、ジフルオロイミダゾ−ル基、トリフルオロメチルイミダゾ−ル基、クロロイミダゾ−ル基、ブロモイミダゾ−ル基等が好適に例示出来、より好ましくは、フェニル基、メチルフェニル基、メトキシフェニル基、ナフチル基、ビフェニル基が好適に例示出来る。前記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し、具体例を挙げれば、水酸基、アミノ基、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炭素数3〜8の環状脂肪族炭化水素基を有するモノ又はジ置換アミノ基、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炭素数3〜8の環状脂肪族炭化水素基を有するアルキルオキシ基、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炭素数1〜8、より好ましくは、炭素数1〜4の脂肪族炭化水素基を有するモノ又はジアルキル置換アミノ基、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炭素数1〜8、より好ましくは、炭素数1〜4の脂肪族炭化水素基を有するアルキルオキシ基、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炭素数3〜8の芳香族炭化水素基を有するモノ又はジ置換アミノ基、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炭素数3〜8の芳香族炭化水素基を有するアルキルオキシ基を表す。尚、前記Bが、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炭素数3〜8の環状脂肪族炭化水素基を有するジ置換アミノ基、又は、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炭素数3〜8の芳香族炭化水素基を有するジ置換アミノ基を表す場合には、環状脂肪族炭化水素基又は芳香族基の環に、AとBとの接合部位の複素原子が含まれた構造も包含する。前記一般式(1)に表される化合物の内、より好ましいものとしては、前記一般式(2)に表される化合物及び/又はそれらの薬理学的に許容される塩が好適に例示出来、さらに好ましいものとしては、前記一般式(3)〜(6)に表される化合物及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。前記一般式(1)に表される化合物の内、前記一般式(2)〜(6)に表される化合物に含まれない化合物を具体的に例示すれば、1−[フェニル(ピリジル)メチル]イミダゾ−ル、1−(ジピリジルメチル)イミダゾ−ル、1−[ジフェニル(ピリジル)メチル]イミダゾ−ル、1−[(ジピリジル)フェニルメチル]イミダゾ−ル、1−(トリピリジルメチル)イミダゾ−ル、2−{[フェニル(ピリジル)メチル]オキシ}エタノ−ル、2−[(ジピリジルメチル)オキシ]エタノ−ル、2−{[ジフェニル(ピリジル)メチル]オキシ}エタノ−ル、2−{[ジピリジル(フェニル)メチル]オキシ}エタノ−ル、2−[(トリピリジルメチル)オキシ]エタノ−ル、2−{[フェニル(ピリジル)メチル]アミノ}エタノ−ル、2−[(ジピリジルメチル)アミノ]エタノ−ル、2−{[ジフェニル(ピリジル)メチル]アミノ}エタノ−ル、2−{[ジピリジル(フェニル)メチル]アミノ}エタノ−ル、2−[(トリピリジルメチル)アミノ]エタノ−ル、2−{[フェニル(ピリジル)メチル]オキシ}エチルアミン、2−[(ジピリジルメチル)オキシ]エチルアミン、2−{[ジフェニル(ピリジル)メチル]オキシ}エチルアミン、2−{[ジピリジル(フェニル)メチル]オキシ}エチルアミン、2−[(トリピリジルメチル)オキシ]エチルアミン、1−[フェニル(ピリジル)メチル]ピロリジン、1−ジピリジルメチルピロリジン、1−[ジフェニル(ピリジル)メチル]ピロリジン、1−[(ジピリジル)フェニルメチル]ピロリジン、1−(トリピリジルメチル)ピロリジン、[フェニル(ピリジル)メチル]ピペリジン、ジピリジルメチルピペリジン、[ジフェニル(ピリジル)メチル]ピペリジン、1−[(ジピリジル)フェニルメチル]ピペリジン、1−(トリピリジルメチル)ピペリジン及び/又はそれらの薬理学的に許容される塩等が好適に例示出来る。また、前記一般式(1)に表される化合物の内、好ましいものを具体的に例示すれば、1−(ジフェニルメチル)イミダゾ−ル(化合物1)、1−(トリフェニルメチル)イミダゾ−ル(化合物2)、2−[(ジフェニルメチル)オキシ]エタノ−ル(化合物3)、2−[(トリフェニルメチル)オキシ]エタノ−ル(化合物4)、2−[(ジフェニルメチル)アミノ]エタノ−ル(化合物5)、2−[(トリフェニルメチル)アミノ]エタノ−ル(化合物6)、2−[(ジフェニルメチル)オキシ]エチルアミン(化合物7)、2−[(トリフェニルメチル)オキシ]エチルアミン(化合物8)、1−(ジフェニルメチル)ピロリジン(化合物9)、1−(トリフェニルメチル)ピロリジン(化合物10)、1−(ジフェニルメチル)ピペリジン(化合物11)、1−(トリフェニルメチル)ピペリジン(化合物12)及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。かかる化合物は、後述する抗シワ剤と共に組成物中に含有させることにより、優れた美肌作用、シワ形成に対する予防又は改善効果を発揮する。また、かかる化合物及び/又はそれらの薬理学的に許容される塩は、優れた安全性、安定性を有し、組成物に安定、且つ、安全に含有させることが出来る。 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.
ここで前記一般式(2)に表される化合物に付いて述べれば、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で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。前記Aにおける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−ルメチル基のアリ−ル基に関し、好ましいものを具体例に挙げれば、フェニル基、ナフチル基、ビフェニル基、メチルフェニル基、エチルフェニル基、プロピルフェニル基、メトキシフェニル基、エトキシフェニル基、プロピルオキシフェニル基、ヒドロキシフェニル基、アミノフェニル基、N−メチルアミノフェニル基、N−エチルアミノフェニル基、N−プロピルアミノフェニル基、N,N−ジメチルアミノフェニル基、N,N−ジエチルアミノフェニル基、N,N−ジプロピルアミノフェニル基、フルオロフェニル基、ジフルオロフェニル基、トリフルオロメチルフェニル基、クロロフェニル基、ブロモフェニル基、メチルナフチル基、エチルナフチル基、プロピルナフチル基、メトキシナフチル基、エトキシナフチル基、プロピルオキシナフチル基、ヒドロキシナフチル基、アミノナフチル基、N−メチルアミノナフチル基、N−エチルアミノナフチル基、N−プロピルアミノナフチル基、N,N−ジメチルアミノナフチル基、N,N−ジエチルアミノナフチル基、N,N−ジプロピルアミノナフチル基、フルオロナフチル基、ジフルオロナフチル基、トリフルオロメチルナフチル基、クロロナフチル基、ブロモナフチル基等が好適に例示出来、より好ましくは、フェニル基、メチルフェニル基、メトキシフェニル基、ナフチル基が好適に例示出来る。前記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し、具体例を挙げれば、水酸基、アミノ基、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炭素数3〜8の環状脂肪族炭化水素基を有するモノ又はジ置換アミノ基、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炭素数3〜8の環状脂肪族炭化水素基を有するアルキルオキシ基、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炭素数1〜8、より好ましくは、炭素数1〜4の脂肪族炭化水素基を有するモノ又はジアルキル置換アミノ基、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炭素数1〜8、より好ましくは、炭素数1〜4の脂肪族炭化水素基を有するアルキルオキシ基、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炭素数3〜8の芳香族炭化水素基を有するモノ又はジ置換アミノ基、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炭素数3〜8の芳香族炭化水素基を有するアルキルオキシ基を表す。尚、前記Bが、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炭素数3〜8の環状脂肪族炭化水素基を有するジ置換アミノ基、又は、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炭素数3〜8の芳香族炭化水素基を有するジ置換アミノ基を表す場合には、環状脂肪族炭化水素基又は芳香族基の環に、AとBとの接合部位の複素原子が含まれた構造も包含する。前記一般式(2)に表される化合物の内、より好ましいものとしては、前記一般式(3)〜(6)に表される化合物及び/又はそれらの薬理学的に許容される塩が好適に例示出来、さらに好ましい化合物を具体的に例示すれば、1−(ジフェニルメチル)イミダゾ−ル(化合物1)、1−(トリフェニルメチル)イミダゾ−ル(化合物2)、2−[(ジフェニルメチル)オキシ]エタノ−ル(化合物3)、2−[(トリフェニルメチル)オキシ]エタノ−ル(化合物4)、2−[(ジフェニルメチル)アミノ]エタノ−ル(化合物5)、2−[(トリフェニルメチル)アミノ]エタノ−ル(化合物6)、2−[(ジフェニルメチル)オキシ]エチルアミン(化合物7)、2−[(トリフェニルメチル)オキシ]エチルアミン(化合物8)、1−(ジフェニルメチル)ピロリジン(化合物9)、1−(トリフェニルメチル)ピロリジン(化合物10)、1−(ジフェニルメチル)ピペリジン(化合物11)、1−(トリフェニルメチル)ピペリジン(化合物12)及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。かかる化合物は、後述する抗シワ剤と共に組成物中に含有させることにより、優れた美肌作用、シワ形成に対する予防又は改善効果を発揮する。また、かかる化合物及び/又はそれらの薬理学的に許容される塩は、優れた安全性、安定性を有し、組成物に安定、且つ、安全に含有させることが出来る。 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.
ここで前記一般式(3)に表される化合物に付いて述べれば、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た環も包含する。前記Aにおける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芳香族メチル基のアリ−ル基に関し、このましいものを具体的に例示すれば、フェニル基、ナフチル基、ビフェニル基、メチルフェニル基、エチルフェニル基、プロピルフェニル基、メトキシフェニル基、エトキシフェニル基、プロピルオキシフェニル基、ヒドロキシフェニル基、アミノフェニル基、N−メチルアミノフェニル基、N−エチルアミノフェニル基、N−プロピルアミノフェニル基、N,N−ジメチルアミノフェニル基、N,N−ジエチルアミノフェニル基、N,N−ジプロピルアミノフェニル基、フルオロフェニル基、ジフルオロフェニル基、トリフルオロメチルフェニル基、クロロフェニル基、ブロモフェニル基、メチルナフチル基、エチルナフチル基、プロピルナフチル基、メトキシナフチル基、エトキシナフチル基、プロピルオキシナフチル基、ヒドロキシナフチル基、アミノナフチル基、N−メチルアミノナフチル基、N−エチルアミノナフチル基、N−プロピルアミノナフチル基、N,N−ジメチルアミノナフチル基、N,N−ジエチルアミノナフチル基、N,N−ジプロピルアミノナフチル基、フルオロナフチル基、ジフルオロナフチル基、トリフルオロメチルナフチル基、クロロナフチル基、ブロモナフチル基等が好適に例示出来、より好ましくは、フェニル基、メチルフェニル基、メトキシフェニル基、ナフチル基等が好適に例示出来る。前記Xは、窒素原子又はNH基を表す。前記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た環も包含する。前記R1に関し、好ましいものを具体的に例示すれば、N−シクロプロピル基、N−シクロブチル基、N−シクロペンチル基、N−シクロヘキシル基、N−シクロヘプチル基、N−シクロオクチル基、スクシンイミド基が好適に例示出来る。また、環状脂肪族炭化水素基の環が、R1のもう一方の末端がXに再び結合し形成された環構造を有する置換基(前記X部分を含む)としては、ピロリジノ基、メチルピロリジノ基、エチルピロリジノ基、プロピルピロリジノ基、メトキシピロリジノ基、エトキシピロリジノ基、プロピルオキシピロリジノ基、ヒドロキシピロリジノ基、アミノピロリジノ基、N−メチルピロリジノ基、N−エチルピロリジノ基、N−プロピルピロリジノ基、N,N−ジメチルピロリジノ基、N,N−ジエチルピロリジノ基、N,N−ジプロピルピロリジノ基、フルオロピロリジノ基、ジフルオロピロリジノ基、トリフルオロメチルピロリジノ基、クロロピロリジノ基、ピペリジル基、メチルピペリジル基、エチルピペリジル基、プロピルピペリジル基、メトキシピペリジル基、エトキシピペリジル基、プロピルオキシピペリジル基、ヒドロキシピペリジル基、アミノピペリジル基、N−メチルピペリジル基、N−エチルピペリジル基、N−プロピルピペリジル基、N,N−ジメチルピペリジル基、N,N−ジエチルピペリジル基、N,N−ジプロピルピペリジル基、フルオロピペリジル基、ジフルオロピペリジル基、トリフルオロメチルピペリジル基、クロロピペリジル基、ピペラジノ基、メチルピペラジノ基、エチルピペラジノ基、プロピルピペラジノ基、メトキシピペラジノ基、エトキシピペラジノ基、プロピルオキシピペラジノ基、ヒドロキシピペラジノ基、アミノピペラジノ基、N−メチルピペラジノ基、N−エチルピペラジノ基、N−プロピルピペラジノ基、N,N−ジメチルピペラジノ基、N,N−ジエチルピペラジノ基、N,N−ジプロピルピペラジノ基、フルオロピペラジノ基、ジフルオロピペラジノ基、トリフルオロメチルピペラジノ基、クロロピペラジノ基、モルホリノ基、メチルモルホリノ基、エチルモルホリノ基、プロピルモルホリノ基、メトキシモルホリノ基、エトキシモルホリノ基、プロピルオキシモルホリノ基、ヒドロキシモルホリノ基、アミノモルホリノ基、N−メチルモルホリノ基、N−エチルモルホリノ基、N−プロピルモルホリノ基、N,N−ジメチルモルホリノ基、N,N−ジエチルモルホリノ基、N,N−ジプロピルモルホリノ基、フルオロモルホリノ基、ジフルオロモルホリノ基、トリフルオロメチルモルホリノ基、クロロモルホリノ基等が好適に例示出来、より好ましくは、ピロリジル基、ピペリジル基、ピペラジル基、モルホリノ基等が好適に例示出来、より好ましくは、ピロリジノ基、ピペリジノ基、ピペラジノ基、モルホリノ基が好適に例示出来る。前記一般式(3)に表される化合物の内、好ましいものを具体的に例示すれば、N−(ジフェニルメチル)スクシンイミド、N−[(メチルフェニル)フェニルメチル]スクシンイミド、N−[ビス(メチルフェニル)メチル]スクシンイミド、N−[(エチルフェニル)フェニルメチル]スクシンイミド、N−[ビス(エチルフェニル)メチル]スクシンイミド、N−[(メトキシフェニル)フェニルメチル]スクシンイミド、N−[ビス(メトキシフェニル)メチル]スクシンイミド、N−[(エトキシフェニル)フェニルメチル]スクシンイミド、N−[ビス(エトキシフェニル)メチル]スクシンイミド、N−[(フルオロフェニル)フェニルメチル]スクシンイミド、N−[ビス(フルオロフェニル)メチル]スクシンイミド、N−(トリフェニルメチル)スクシンイミド、N−[ジフェニル(メチルフェニル)メチル]スクシンイミド、N−[ビス(メチルフェニル)フェニルメチル]スクシンイミド、N−[トリス(メチルフェニル)メチル]スクシンイミド、N−[ジフェニル(エチルフェニル)メチル]スクシンイミド、N−[ビス(エチルフェニル)フェニルメチル]スクシンイミド、N−[トリス(エチルフェニル)メチル]スクシンイミド、N−[ジフェニル(メトキシフェニル)メチル]スクシンイミド、N−[ビス(メトキシフェニル)フェニルメチル]スクシンイミド、N−[トリス(メトキシフェニル)メチル]スクシンイミド、N−[ジフェニル(エトキシフェニル)メチル]スクシンイミド、N−[ビス(エトキシフェニル)フェニルメチル]スクシンイミド、N−[トリス(エトキシフェニル)メチル]スクシンイミド、N−[ジフェニル(フルオロフェニル)メチル]スクシンイミド、N−[ビス(フルオロフェニル)フェニルメチル]スクシンイミド、N−[トリス(フルオロフェニル)メチル]スクシンイミド、1−(ジフェニルメチル)ピロリジン(化合物9)、1−[(メチルフェニル)フェニルメチル]ピロリジン、1−[ビス(メチルフェニル)メチル]ピロリジン、1−[(エチルフェニル)フェニルメチル]ピロリジン、1−[ビス(エチルフェニル)メチル]ピロリジン、1−[(メトキシフェニル)フェニルメチル]ピロリジン、1−[ビス(メトキシフェニル)メチル]ピロリジン、1−[(エチルフェニル)フェニルメチル]ピロリジン、1−[ビス(エチルフェニル)メチル]ピロリジン、1−[(ヒドロキシフェニル)フェニルメチル]ピロリジン、1−[ビス(ヒドロキシフェニル)メチル]ピロリジン、1−[(アミノフェニル)フェニルメチル]ピロリジン、1−[ビス(アミノフェニル)メチル]ピロリジン、1−[(フルオロフェニル)フェニルメチル]ピロリジン、1−[ビス(フルオロフェニル)メチル]ピロリジン、1−[(クロロフェニル)フェニルメチル]ピロリジン、1−[ビス(クロロフェニル)メチル]ピロリジン、1−(トリフェニルメチル)ピロリジン(化合物10)、1−[ジフェニル(メチルフェニル)メチル]ピロリジン、1−[ビス(メチルフェニル)フェニルメチル]ピロリジン、1−[トリス(メチルフェニル)メチル]ピロリジン、1−[ジフェニル(エチルフェニル)メチル]ピロリジン、1−[ビス(エチルフェニル)フェニルメチル]ピロリジン、1−[トリス(エチルフェニル)メチル]ピロリジン、1−[ジフェニル(メトキシフェニル)メチル]ピロリジン、1−[ビス(メトキシフェニル)フェニルメチル]ピロリジン、1−[トリス(メトキシフェニル)メチル]ピロリジン、1−[ジフェニル(エトキシフェニル)メチル]ピロリジン、1−[ビス(エトキシフェニル)フェニルメチル]ピロリジン、1−[トリス(エトキシフェニル)メチル]ピロリジン、1−[ジフェニル(ヒドロキシフェニル)メチル]ピロリジン、1−[ビス(ヒドロキシフェニル)フェニルメチル]ピロリジン、1−[トリス(ヒドロキシフェニル)メチル]ピロリジン、1−[(アミノフェニル)ジフェニルメチル]ピロリジン、1−[ビス(アミノフェニル)フェニルメチル]ピロリジン、1−[トリス(アミノフェニル)メチル]ピロリジン、1−[ジフェニル(フルオロフェニル)メチル]ピロリジン、1−[ビス(フルオロフェニル)フェニルメチル]ピロリジン、1−[トリス(フルオロフェニル)メチル]ピロリジン、1−(ジフェニルメチル)ピペリジン(化合物11)、1−[(メチルフェニル)フェニルメチル]ピぺリジン、1−[ビス(メチルフェニル)メチル]ピぺリジン、1−[(エチルフェニル)フェニルメチル]ピぺリジン、1−[ビス(エチルフェニル)メチル]ピぺリジン、1−[(メトキシフェニル)フェニルメチル]ピぺリジン、1−[ビス(メトキシフェニル)メチル]ピぺリジン、1−[(エチルフェニル)フェニルメチル]ピぺリジン、1−[ビス(エチルフェニル)メチル]ピぺリジン、1−[(ヒドロキシフェニル)フェニルメチル]ピペリジン、1−[ビス(ヒドロキシフェニル)メチル]ピペリジン、1−[(アミノフェニル)フェニルメチル]ピペリジン、1−[ビス(アミノフェニル)メチル]ピペリジン、1−[(フルオロフェニル)フェニルメチル]ピペリジン、1−[ビス(フルオロフェニル)メチル]ピペリジン、1−[(クロロフェニル)フェニルメチル]ピペリジン、1−[ビス(クロロフェニル)メチル]ピペリジン、1−(トリフェニルメチル)ピペリジン(化合物12)、1−[ジフェニル(メチルフェニル)メチル]ピペリジン、1−[ビス(メチルフェニル)フェニルメチル]ピペリジン、1−[トリス(メチルフェニル)メチル]ピペリジン、1−[ジフェニル(エチルフェニル)メチル]ピペリジン、1−[ビス(エチルフェニル)フェニルメチル]ピペリジン、1−[トリス(エチルフェニル)メチル]ピペリジン、1−[ジフェニル(メトキシフェニル)メチル]ピペリジン、1−[ビス(メトキシフェニル)フェニルメチル]ピペリジン、1−[トリス(メトキシフェニル)メチル]ピペリジン、1−[ジフェニル(エトキシフェニル)メチル]ピペリジン、1−[ビス(エトキシフェニル)フェニルメチル]ピペリジン、1−[トリス(エトキシフェニル)メチル]ピペリジン、1−[ジフェニル(ヒドロキシフェニル)メチル]ピペリジン、1−[ビス(ヒドロキシフェニル)フェニルメチル]ピペリジン、1−[トリス(ヒドロキシフェニル)メチル]ピペリジン、1−[(アミノフェニル)ジフェニルメチル]ピペリジン、1−[ビス(アミノフェニル)フェニルメチル]ピペリジン、1−[トリス(アミノフェニル)メチル]ピペリジン、1−[ジフェニル(フルオロフェニル)メチル]ピペリジン、1−[ビス(フルオロフェニル)フェニルメチル]ピペリジン、1−[トリス(フルオロフェニル)メチル]ピペリジン、1−(ジフェニルメチル)モルホリン、1−[(メチルフェニル)フェニルメチル]モルホリン、1−[ビス(メチルフェニル)メチル]モルホリン、1−[(エチルフェニル)フェニルメチル]モルホリン、1−[ビス(エチルフェニル)メチル]モルホリン、1−[(メトキシフェニル)フェニルメチル]モルホリン、1−[ビス(メトキシフェニル)メチル]モルホリン、1−[(エチルフェニル)フェニルメチル]モルホリン、1−[ビス(エチルフェニル)メチル]モルホリン、1−[(ヒドロキシフェニル)フェニルメチル]モルホリン、1−[ビス(ヒドロキシフェニル)メチル]モルホリン、1−[(アミノフェニル)フ
ェニルメチル]モルホリン、1−[ビス(アミノフェニル)メチル]モルホリン、1−[(フルオロフェニル)フェニルメチル]モルホリン、1−[ビス(フルオロフェニル)メチル]モルホリン、1−[(クロロフェニル)フェニルメチル]モルホリン、1−[ビス(クロロフェニル)メチル]モルホリン、1−(トリフェニルメチル)モルホリン、1−[ジフェニル(メチルフェニル)メチル]モルホリン、1−[ビス(メチルフェニル)フェニルメチル]モルホリン、1−[トリス(メチルフェニル)メチル]モルホリン、1−[ジフェニル(エチルフェニル)メチル]モルホリン、1−[ビス(エチルフェニル)フェニルメチル]モルホリン、1−[トリス(エチルフェニル)メチル]モルホリン、1−[ジフェニル(メトキシフェニル)メチル]モルホリン、1−[ビス(メトキシフェニル)フェニルメチル]モルホリン、1−[トリス(メトキシフェニル)メチル]モルホリン、1−[ジフェニル(エトキシフェニル)メチル]モルホリン、1−[ビス(エトキシフェニル)フェニルメチル]モルホリン、1−[トリス(エトキシフェニル)メチル]モルホリン、1−[ジフェニル(ヒドロキシフェニル)メチル]モルホリン、1−[ビス(ヒドロキシフェニル)フェニルメチル]モルホリン、1−[トリス(ヒドロキシフェニル)メチル]モルホリン、1−[(アミノフェニル)ジフェニルメチル]モルホリン、1−[ビス(アミノフェニル)フェニルメチル]モルホリン、1−[トリス(アミノフェニル)メチル]モルホリン、1−[ジフェニル(フルオロフェニル)メチル]モルホリン、1−[ビス(フルオロフェニル)フェニルメチル]モルホリン、1−[トリス(フルオロフェニル)メチル]モルホリン及び/又はそれらの薬理学的に許容される塩が好適に例示出来、より好ましいものとしては、1−(ジフェニルメチル)ピロリジン(化合物9)、1−(トリフェニルメチル)ピロリジン(化合物10)、1−(ジフェニルメチル)ピペリジン(化合物11)、1−(トリフェニルメチル)ピペリジン(化合物12)及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。かかる化合物は、後述する抗シワ剤と共に組成物中に含有させることにより、優れた美肌作用、シワ形成に対する予防又は改善効果を発揮する。また、かかる化合物及び/又はそれらの薬理学的に許容される塩は、優れた安全性、安定性を有し、組成物に安定、且つ、安全に含有させることが出来る。
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.
ここで前記一般式(4)に表される化合物に付いて述べれば、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より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。前記Aにおける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−ルメチル基のアリ−ル基に関し、好ましいものを具体的に例示すれば、フェニル基、ナフチル基、ビフェニル基、メチルフェニル基、エチルフェニル基、プロピルフェニル基、メトキシフェニル基、エトキシフェニル基、プロピルオキシフェニル基、ヒドロキシフェニル基、アミノフェニル基、N−メチルアミノフェニル基、N−エチルアミノフェニル基、N−プロピルアミノフェニル基、N,N−ジメチルアミノフェニル基、N,N−ジエチルアミノフェニル基、N,N−ジプロピルアミノフェニル基、フルオロフェニル基、ジフルオロフェニル基、トリフルオロメチルフェニル基、クロロフェニル基、ブロモフェニル基、メチルナフチル基、エチルナフチル基、プロピルナフチル基、メトキシナフチル基、エトキシナフチル基、プロピルオキシナフチル基、ヒドロキシナフチル基、アミノナフチル基、N−メチルアミノナフチル基、N−エチルアミノナフチル基、N−プロピルアミノナフチル基、N,N−ジメチルアミノナフチル基、N,N−ジエチルアミノナフチル基、N,N−ジプロピルアミノナフチル基、フルオロナフチル基、ジフルオロナフチル基、トリフルオロメチルナフチル基、クロロナフチル基、ブロモナフチル基等が好適に例示出来、より好ましくは、フェニル基、ナフチル基、メチルフェニル基、メトキシフェニル基等が好適に例示出来る。前記Xは、酸素原子を表す。前記R2は、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炭素数1〜8、より好ましくは、炭素数1〜4の脂肪族炭化水素を表し、具体例を挙げれば、ヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシプロピル基、ヒドロキシブチル基、ヒドロキシペンチル基、ヒドロキシヘキシル基、ヒドロキシヘプチル基、ヒドロキシオクチル基、メトキシメチル基、メトキシエチル基、メトキシプロピル基、メトキシブチル基、メトキシペンチル基、メトキシヘキシル基、メトキシヘプチル基、メトキシオクチル基、ジヒドロキシメチル基、ジヒドロキシエチル基、ジヒドロキシプロピル基、ジヒドロキシブチル基、ジヒドロキシペンチル基、ジヒドロキシヘキシル基、ジヒドロキシへプチル基、ジヒドロキシオクチル基、アミノメチル基、アミノエチル基、アミノプロピル基、アミノブチル基、アミノペンチル基、アミノヘキシル基、アミノヘプチル基、アミノオクチル基等が好適に例示出来、よりこ好ましくは、ヒドロキシエチル基、アミノエチル基、メトキシエチル基が好適に例示出来る。前記一般式(4)に表される化合物の内、好ましい化合物を具体的に例示すれば、1−(ジフェニルメチルオキシ)メタノ−ル、3−(ジフェニルメチルオキシ)プロパノ−ル、4−(ジフェニルメチルオキシ)ブタノ−ル、5−(ジフェニルメチルオキシ)ペンタノ−ル、6−(ジフェニルメチルオキシ)ヘキサノ−ル、7−(ジフェニルメチルオキシ)ヘプタノ−ル、8−(ジフェニルメチルオキシ)オクタノ−ル、1−(トリフェニルメチルオキシ)メタノ−ル、3−(トリフェニルメチルオキシ)プロパノ−ル、4−(トリフェニルメチルオキシ)ブタノ−ル、5−(トリフェニルメチルオキシ)ペンタノ−ル、6−(トリフェニルメチルオキシ)ヘキサノ−ル、7−(トリフェニルメチルオキシ)ヘプタノ−ル、8−(トリフェニルメチルオキシ)オクタノ−ル、1−(ジフェニルメチルオキシ)メチルアミン、3−(ジフェニルメチルオキシ)プロピルアミンアミン、4−(ジフェニルメチルオキシ)ブチルアミン、5−(ジフェニルメチルオキシ)ペンチルアミン、6−(ジフェニルメチルオキシ)ヘキシルアミン、7−(ジフェニルメチルオキシ)ヘプチルアミン、8−(ジフェニルメチルオキシ)オクチルアミン、1−(トリフェニルメチルオキシ)メチルアミン、3−(トリフェニルメチルオキシ)プロピルアミン、4−(トリフェニルメチルオキシ)ブチルアミン、5−(トリフェニルメチルオキシ)ペンチルアミン、6−(トリフェニルメチルオキシ)ヘキシルアミン、7−(トリフェニルメチルオキシ)ヘプチルアミン、8−(トリフェニルメチルオキシ)オクチルアミン、1−(ジフェニルメチルアミノ)メタノ−ル、3−(ジフェニルメチルアミノ)プロパノ−ル、4−(ジフェニルメチルアミノ)ブタノ−ル、5−(ジフェニルメチルアミノ)ペンタノ−ル、6−(ジフェニルメチルアミノ)ヘキサノ−ル、7−(ジフェニルメチルアミノ)ヘプタノ−ル、8−(ジフェニルメチルアミノ)オクタノ−ル、1−(トリフェニルメチルアミノ)メタノ−ル、3−(トリフェニルメチルアミノ)プロパノ−ル、4−(トリフェニルメチルアミノ)ブタノ−ル、5−(トリフェニルメチルアミノ)ペンタノ−ル、6−(トリフェニルメチルアミノ)ヘキサノ−ル、7−(トリフェニルメチルアミノ)ヘプタノ−ル、8−(トリフェニルメチルアミノ)オクタノ−ル、2−[(ジフェニルメチル)オキシ]エタノ−ル(化合物3)、2−[(メチルフェニル)フェニルメチルオキシ]エタノ−ル、2−[ビス(メチルフェニル)メチルオキシ]エタノ−ル、2−[(エチルフェニル)フェニルメチルオキシ]エタノ−ル、2−[(ビス(エチルフェニル)メチルオキシ]エタノ−ル、2−[(メトキシフェニル)フェニルメチルオキシ]エタノ−ル、2−[(ビス(メトキシフェニル)メチルオキシ]エタノ−ル、2−[(エトキシフェニル)フェニルメチルオキシ]エタノ−ル、2−[(ビス(エトキシフェニル)メチルオキシ]エタノ−ル、2−[(ヒドロキシフェニル)フェニルメチルオキシ]エタノ−ル、2−[(ビス(ヒドロキシフェニル)メチルオキシ]エタノ−ル、2−[(アミノフェニル)フェニルメチルオキシ]エタノ−ル、2−[(ビス(アミノフェニル)メチルオキシ]エタノ−ル、2−[(フルオロフェニル)フェニルメチルオキシ]エタノ−ル、2−[(ビス(フルオロフェニル)メチルオキシ]エタノ−ル、2−[(トリフェニルメチル)オキシ]エタノ−ル(化合物4)、2−[ジフェニル(メチルフェニル)メチルオキシ]エタノ−ル、2−[ビス(メチルフェニル)フェニルメチルオキシ]エタノ−ル、2−[トリス(メチルフェニル)メチルオキシ]エタノ−ル、2−[ジフェニル(エチルフェニル)メチルオキシ]エタノ−ル、2−[ビス(エチルフェニル)フェニルメチルオキシ]エタノ−ル、2−[トリス(エチルフェニル)メチルオキシ]エタノ−ル、2−[ジフェニル(メトキシフェニル)メチルオキシ]エタノ−ル、2−[ビス(メトキシフェニル)フェニルメチルオキシ]エタノ−ル、2−[トリス(メトキシフェニル)メチルオキシ]エタノ−ル、2−[ジフェニル(エトキシフェニル)メチルオキシ]エタノ−ル、2−[ビス(エトキシフェニル)フェニルメチルオキシ]エタノ−ル、2−[トリス(エトキシフェニル)メチルオキシ]エタノ−ル、2−[ジフェニル(ヒドロキシフェニル)メチルオキシ]エタノ−ル、2−[ビス(ヒドロキシフェニル)フェニルメチルオキシ]エタノ−ル、2−[トリス(ヒドロキシフェニル)メチルオキシ]エタノ−ル、2−[(アミノフェニル)ジフェニルメチルオキシ]エタノ−ル、2−[ビス(アミノフェニル)フェニルメチルオキシ]エタノ−ル、2−[トリス(アミノフェニル)メチルオキシ]エタノ−ル、2−[ジフェニル(フルオロフェニル)メチルオキシ]エタノ−ル、2−[ビス(フルオロフェニル)フェニルメチルオキシ]エタノ−ル、2−[トリス(フルオロフェニル)メチルオキシ]エタノ−ル、2−[(ジフェニルメチル)オキシ]エチルアミン(化合物7)、2−[(メチルフェニル)フェニルメチルオキシ]エチルアミン、2−[ビス(メチルフェニル)メチルオキシ]エチルアミン、2−[(エチルフェニル)フェニルメチルオキシ]エチルアミン、2−[(ビス(エチルフェニル)メチルオキシ]エチルアミン、2−[(メトキシフェニル)フェニルメチルオキシ]エチルアミン、2−[(ビス(メトキシフェニル)メチルオキシ]エチルアミン、2−[(エトキシフェニル)フェニルメチルオキシ]エチルアミン、2−[(ビス(エトキシフェニル)メチルオキシ]エチルアミン、2−[(ヒドロキシフェニル)フェニルメチルオキシ]エチルアミン、2−[(ビス(ヒドロキシフェニル)メチルオキシ]エチルアミン、2−[(アミノフェニル)フェニルメチルオキシ]エチルアミン、2−[(ビス(アミノフェニル)メチルオキシ]エチルアミン、2−[(フルオロフェニル)フェニルメチルオキシエチルアミン、2−[(ビス(フルオロフェニル)メチルオキシ]エチルアミン、2−[(トリフェニルメチル)オキシ]エチルアミン(化合物8)、2−[ジフェニル(メチルフェニル)メチルオキシ]エチルアミン、2−[ビス(メチルフェニル)フェニルメチルオキシ]エチルアミン、2−[トリス(メチルフェニル)メチルオキシ]エチルアミン、2−[ジフェニル(エチルフェニル)メチルオキシ]エチルアミン、2−[ビス(エチルフェニル)フェニルメチルオキシ]エチルアミン、2−[トリス(エチルフェニル)メチルオキシ]エチルアミン、2−[ジフェニル(メトキシフェニル)メチルオキシ]エチルアミン、2−[ビス(メトキシフェニル)フェニルメチルオキシ]エチルアミン、2−[トリス(メトキシフェニル)メチルオキシ]エチルアミン、2−[ジフェニル(エトキシフェニル)メチルオキシ]エチルアミン、2−[ビス(エトキシフェニル)フェニルメチルオキシ]エチルアミン、2−[トリス(エトキシフェニル)メチルオキシ]エチルアミン、2−[ジフェニル(ヒドロキシフェニル)メチルオキシ]エチルアミン、2−[ビス(ヒドロキシフェニル)フェニルメチルオキシ]エチルアミン、2−[トリス(ヒドロキシフェニル)メチルオキシ]エチルアミン、2−[(アミノフェニル)ジフェニルメチルオキシ]エチルアミン、2−[ビス(アミノフェニル)フェニルメチルオキシ]エチルアミン、2−[トリス(アミノフェニル)メチルオキシ]エチルアミン、2−[ジフェニル(フルオロフェニル)メチルオキシ]エチルアミン、2−[ビス(フルオロフェニル)フェニルメチルオキシ]エチルアミン、2−[トリス(フルオロフェニル)メチルオキシ]エチルアミン及び/又はそれらの薬理学的に許容される塩が好適に例示出来、より好ましくは、2−[(ジフェニルメチル)オキシ]エタノ−ル(化合物3)、2−[(トリフェニルメチル)オキシ]エタノ−ル(化合物4)、2−[(ジフェニルメチル)オキシ]エチルアミン(化合物7)、2−[(トリフェニルメチル)オキシ]エチルアミン(化合物8)及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。かかる化合物は、後述する抗シワ剤と共に組成物中に含有させることにより、優れた美肌作用、シワ形成に対する予防又は改善効果を発揮する。また、かかる化合物及び/又はそれらの薬理学的に許容される塩は、優れた安全性、安定性を有し、組成物に安定、且つ、安全に含有させることが出来る。 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.
ここで前記一般式(5)に表される化合物に付いて述べれば、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。前記Aにおける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−ルメチル基のアリ−ル基に関し、好ましいものを具体的に例示すれば、フェニル基、ナフチル基、ビフェニル基、メチルフェニル基、エチルフェニル基、プロピルフェニル基、メトキシフェニル基、エトキシフェニル基、プロピルオキシフェニル基、ヒドロキシフェニル基、アミノフェニル基、N−メチルアミノフェニル基、N−エチルアミノフェニル基、N−プロピルアミノフェニル基、N,N−ジメチルアミノフェニル基、N,N−ジエチルアミノフェニル基、N,N−ジプロピルアミノフェニル基、フルオロフェニル基、ジフルオロフェニル基、トリフルオロメチルフェニル基、クロロフェニル基、ブロモフェニル基、メチルナフチル基、エチルナフチル基、プロピルナフチル基、メトキシナフチル基、エトキシナフチル基、プロピルオキシナフチル基、ヒドロキシナフチル基、アミノナフチル基、N−メチルアミノナフチル基、N−エチルアミノナフチル基、N−プロピルアミノナフチル基、N,N−ジメチルアミノナフチル基、N,N−ジエチルアミノナフチル基、N,N−ジプロピルアミノナフチル基、フルオロナフチル基、ジフルオロナフチル基、トリフルオロメチルナフチル基、クロロナフチル基、ブロモナフチル基等が好適に例示出来、より好ましくは、フェニル基、ナフチル基、メチルフェニル基、メトキシフェニル基等が好適に例示出来る。前記Xは、窒素原子を表す。前記R3及びR4は、それぞれ独立に水素原子、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もよい炭素数1〜8、より好ましくは、炭素数1〜4の脂肪族炭化水素基を表し、R3及びR4に関し、好ましいものを具体的に例示すれば、水素原子、ヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシプロピル基、ヒドロキシブチル基、ヒドロキシペンチル基、ヒドロキシヘキシル基、ヒドロキシヘプチル基、ヒドロキシオクチル基、メトキシメチル基、メトキシエチル基、メトキシプロピル基、メトキシブチル基、メトキシペンチル基、メトキシヘキシル基、メトキシヘプチル基、メトキシオクチル基、ジヒドロキシメチル基、ジヒドロキシエチル基、ジヒドロキシプロピル基、ジヒドロキシブチル基、ジヒドロキシペンチル基、ジヒドロキシヘキシル基、ジヒドロキシへプチル基、ジヒドロキシオクチル基、アミノメチル基、アミノエチル基、アミノプロピル基、アミノブチル基、アミノペンチル基、アミノヘキシル基、アミノヘプチル基、アミノオクチル基等が好適に例示出来、よりこ好ましくは、ヒドロキシエチル基、アミノエチル基、メトキシエチル基が好適に例示出来る。前記一般式(5)に表される化合物の内、好ましい化合物を具体的に例示すれば、2−[(ジフェニルメチル)アミノ]エタノ−ル(化合物5)、2−[(メチルフェニル)フェニルメチルアミノ]エタノ−ル、2−[ビス(メチルフェニル)メチルアミノ]エタノ−ル、2−[(エチルフェニル)フェニルメチルアミノ]エタノ−ル、2−[(ビス(エチルフェニル)メチルアミノ]エタノ−ル、2−[(メトキシフェニル)フェニルメチルアミノ]エタノ−ル、2−[(ビス(メトキシフェニル)メチルアミノ]エタノ−ル、2−[(エトキシフェニル)フェニルメチルアミノ]エタノ−ル、2−[(ビス(エトキシフェニル)メチルアミノ]エタノ−ル、2−[(ヒドロキシフェニル)フェニルメチルアミノ]エタノ−ル、2−[(ビス(ヒドロキシフェニル)メチルアミノ]エタノ−ル、2−[(アミノフェニル)フェニルメチルアミノ]エタノ−ル、2−[(ビス(アミノフェニル)メチルアミノ]エタノ−ル、2−[(フルオロフェニル)フェニルメチルアミノ]エタノ−ル、2−[(ビス(フルオロフェニル)メチルアミノ]エタノ−ル、2−[(トリフェニルメチル)アミノ]エタノ−ル(化合物6)、2−[ジフェニル(メチルフェニル)メチルアミノ]エタノ−ル、2−[ビス(メチルフェニル)フェニルメチルアミノ]エタノ−ル、2−[トリス(メチルフェニル)メチルアミノ]エタノ−ル、2−[ジフェニル(エチルフェニル)メチルアミノ]エタノ−ル、2−[ビス(エチルフェニル)フェニルメチルアミノ]エタノ−ル、2−[トリス(エチルフェニル)メチルアミノ]エタノ−ル、2−[ジフェニル(メトキシフェニル)メチルアミノ]エタノ−ル、2−[ビス(メトキシフェニル)フェニルメチルアミノ]エタノ−ル、2−[トリス(メトキシフェニル)メチルアミノ]エタノ−ル、2−[ジフェニル(エトキシフェニル)メチルアミノ]エタノ−ル、2−[ビス(エトキシフェニル)フェニルメチルアミノ]エタノ−ル、2−[トリス(エトキシフェニル)メチルアミノ]エタノ−ル、2−[ジフェニル(ヒドロキシフェニル)メチルアミノ]エタノ−ル、2−[ビス(ヒドロキシフェニル)フェニルメチルアミノ]エタノ−ル、2−[トリス(ヒドロキシフェニル)メチルアミノ]エタノ−ル、2−[(アミノフェニル)ジフェニルメチルアミノ]エタノ−ル、2−[ビス(アミノフェニル)フェニルメチルアミノ]エタノ−ル、2−[トリス(アミノフェニル)メチルアミノ]エタノ−ル、2−[ジフェニル(フルオロフェニル)メチルアミノ]エタノ−ル、2−[ビス(フルオロフェニル)フェニルメチルアミノ]エタノ−ル、2−[トリス(フルオロフェニル)メチルアミノ]エタノ−ル及び/又はそれらの薬理学的に許容される塩が好適に例示出来、より好ましくは、2−[(ジフェニルメチル)アミノ]エタノ−ル(化合物5)、2−[(トリフェニルメチル)アミノ]エタノ−ル(化合物6)及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。かかる化合物は、後述する抗シワ剤と共に組成物中に含有させることにより、優れた美肌作用、シワ形成に対する予防又は改善効果を発揮する。また、かかる化合物及び/又はそれらの薬理学的に許容される塩は、優れた安全性、安定性を有し、組成物に安定、且つ、安全に含有させることが出来る。 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.
ここで前記一般式(6)に表される化合物に付いて述べれば、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。前記Aにおける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−ルメチル基のアリ−ル基に関し、好ましいものを具体的に例示すれば、フェニル基、ナフチル基、ビフェニル基、メチルフェニル基、エチルフェニル基、プロピルフェニル基、メトキシフェニル基、エトキシフェニル基、プロピルオキシフェニル基、ヒドロキシフェニル基、アミノフェニル基、N−メチルアミノフェニル基、N−エチルアミノフェニル基、N−プロピルアミノフェニル基、N,N−ジメチルアミノフェニル基、N,N−ジエチルアミノフェニル基、N,N−ジプロピルアミノフェニル基、フルオロフェニル基、ジフルオロフェニル基、トリフルオロメチルフェニル基、クロロフェニル基、ブロモフェニル基、メチルナフチル基、エチルナフチル基、プロピルナフチル基、メトキシナフチル基、エトキシナフチル基、プロピルオキシナフチル基、ヒドロキシナフチル基、アミノナフチル基、N−メチルアミノナフチル基、N−エチルアミノナフチル基、N−プロピルアミノナフチル基、N,N−ジメチルアミノナフチル基、N,N−ジエチルアミノナフチル基、N,N−ジプロピルアミノナフチル基、フルオロナフチル基、ジフルオロナフチル基、トリフルオロメチルナフチル基、クロロナフチル基、ブロモナフチル基等が好適に例示出来、より好ましくは、フェニル基、ナフチル基、メチルフェニル基、メトキシフェニル基等が好適に例示出来る。Xは、窒素原子又はNH基を表す。前記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基を表す。かかる芳香族炭化水素基に関し具体例を挙げれば、フェニル基、ピリジル基、イミダゾ−ル基、フリル基、チエニル基等が好適に例示出来、より好ましくは、イミダゾ−ル基が好適に例示出来る。前記一般式(6)に表される化合物に関し具体例を挙げれば、1−(ジフェニルメチル)イミダゾ−ル(化合物1)、1−[(メチルフェニル)メチル]イミダゾ−ル、1−[ビス(メチルフェニル)メチル]イミダゾ−ル、1−[(エチルフェニル)メチル]イミダゾ−ル、1−[ビス(エチルフェニル)メチル]イミダゾ−ル、1−[(メトキシフェニル)メチル]イミダゾ−ル、1−[ビス(メトキシフェニル)メチル]イミダゾ−ル、1−[(エトキシフェニル)メチル]イミダゾ−ル、1−[ビス(エトキシフェニル)メチル]イミダゾ−ル、1−[(ヒドロキシフェニル)メチル]イミダゾ−ル、1−[ビス(ヒドロキシフェニル)メチル]イミダゾ−ル、1−[(アミノフェニル)メチル]イミダゾ−ル、1−[ビス(アミノフェニル)メチル]イミダゾ−ル、1−[(フルオロフェニル)メチル]イミダゾ−ル、1−[ビス(フルオロフェニル)メチル]イミダゾ−ル、1−(トリフェニルメチル)イミダゾ−ル(化合物2)、1−[ジフェニル(メチルフェニル)メチル]イミダゾ−ル、1−[ビス(メチルフェニル)フェニルメチル]イミダゾ−ル、1−[トリス(メチルフェニル)メチル]イミダゾ−ル、1−[ジフェニル(エチルフェニル)メチル]イミダゾ−ル、1−[ビス(エチルフェニル)フェニルメチル]イミダゾ−ル、1−[トリス(エチルフェニル)メチル]イミダゾ−ル、1−[ジフェニル(メトキシフェニル)メチル]イミダゾ−ル、1−[ビス(メトキシフェニル)フェニルメチル]イミダゾ−ル、1−[トリス(メトキシフェニル)メチル]イミダゾ−ル、1−[ジフェニル(エトキシフェニル)メチル]イミダゾ−ル、1−[ビス(メトキシフェニル)フェニルメチル]イミダゾ−ル、1−[トリス(エトキシフェニル)メチル]イミダゾ−ル、1−[ジフェニル(ヒドロキシフェニル)メチル]イミダゾ−ル、1−[ビス(ヒドロキシフェニル)フェニルメチル]イミダゾ−ル、1−[トリス(ヒドロキシフェニル)メチル]イミダゾ−ル、1−[(アミノフェニル)ジフェニルメチル]イミダゾ−ル、1−[ビス(アミノフェニル)フェニルメチル]イミダゾ−ル、1−[トリス(アミノフェニル)メチル]イミダゾ−ル、1−[ジフェニル(フルオロフェニル)メチル]イミダゾ−ル、1−[ビス(フルオロフェニル)フェニルメチル]イミダゾ−ル、1−[トリス(フルオロフェニル)メチル]イミダゾ−ル及び/又はそれらの薬理学的に許容される塩が好適に例示出来、より好ましくは、1−(ジフェニルメチル)イミダゾ−ル(化合物1)、1−(トリフェニルメチル)イミダゾ−ル(化合物2)及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。かかる化合物は、後述する抗シワ剤と共に組成物中に含有させることにより、優れた美肌作用、シワ形成に対する予防又は改善効果を発揮する。また、かかる化合物及び/又はそれらの薬理学的に許容される塩は、優れた安全性、安定性を有し、組成物に安定、且つ、安全に含有させることが出来る。 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.
前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩は、後述する抗シワ剤と共に組成物に含有させることにより、美肌作用、取り分け、シワ形成に対する予防又は改善作用を発揮する。前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、抗シワ剤とを共に含有させることにより発揮される優れた美肌作用、並びに、シワ形成に対する予防又は改善作用、言い換えれば、美肌作用、並びに、シワ形成に対する予防又は改善効果における増強作用は、両成分の薬理学的な効果における相加又は相乗効果に加え、標的部位への送達効率向上等の薬物動態的な作用、製剤的な相加又は相乗作用によると考えられる。 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.
前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩は、市販の相当する試薬を出発原料とし、下記に示す方法に従い又は参考に合成することが出来る。前記一般式(1)に表される化合物の合成方法に関しては、本出願人により出願されたPCT/JP2009/071279号公報に記載の合成方法に従い製造することが出来る。かかる化合物は、そのまま後述する抗シワ剤と共に組成物中に含有させることにより、美肌作用、シワ形成に対する予防又は改善作用の効果増強のために使用することも出来るが、薬理学的に許容される酸又は塩基と共に処理し塩の形に変換し、塩として使用することも可能である。例えば、塩酸塩、硫酸塩、硝酸塩、リン酸塩、炭酸塩などの鉱酸塩、マレイン酸塩、フマル酸塩、シュウ酸塩、クエン酸塩、乳酸塩、酒石酸塩、メタンスルホン酸塩、パラトルエンスルホン酸塩、ベンゼンスルホン酸塩などの有機酸塩、ナトリウム塩、カリウム塩等のアルカリ金属、カルシウム塩、マグネシウム塩等のアルカリ土類金属、トリエチルアミン塩、トリエタノ−ルアミン塩、アンモニウム塩、モノエタノ−ルアミン塩、ピペリジン塩等の有機アミン塩、リジン塩、アルギン酸塩等の塩基性アミノ酸塩などが好適に例示出来る。 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.
本発明の前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩が、後述する抗シワ剤と共に働き、美肌作用、取り分け、シワ形成に対する予防又は改善作用における増強効果を奏するためには、組成物全量に対し、総量で0.001質量%〜10質量%、より好ましくは、0.01質量%〜5質量%、さらに好ましくは、0.1質量%〜3質量%含有することが好ましい。これは、少なすぎると前記効果を奏さない場合が存し、多すぎても、効果が頭打ちになり、徒に系の自由度を損なう場合が存するためである。 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.
<製造例1: 化合物1及び化合物2の製造方法>
化合物1及び化合物2は、特開昭53−16879号公報に記載された方法に従い合成した。尚、化合物2は、和光純薬工業株式会社より試薬として購入することもできる。
<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.
<製造例2: 化合物3及び化合物4の製造方法>
エチレングリコ−ル(3.10g、49.9mmol)(和光純薬)及びトリフェニルクロロメタン(1.39g、49.9mmol)(和光純薬)をピリジン(6mL)(和光純薬)に溶解し、45℃に加温し、2時間撹拌した。反応液に水(50mL)を注ぎ、トルエン(和光純薬)にて抽出した。有機層を無水硫酸ナトリム(和光純薬)で乾燥し、減圧下溶媒を留去した。得られた粗製物をシリカゲルカラムクロマトグラフィ−(クロロホルム(和光純薬):メタノ−ル(和光純薬)=9:1)にて精製し、化合物4(収量0.37g、収率24%)を得た。また、トリフェニルクロロメタンの代わりにジフェニルクロロメタンを使用し同様の操作を行うことにより、化合物3を得ることが出来る。
<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.
<化合物4の物理恒数>
mp.103−106℃
1H-HMR(CDCl3):δ3.26(t、J=4.5Hz、2H)、3.75(t、J=4.5Hz、2H)、7.23−7.54(m、15H).
IR(cm-1): 3337、1448、1093、1061.
<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.
<製造例3: 化合物5及び化合物6の製造方法>
トリフェニルクロロメタン(1.00g、3.58mmol)(和光純薬)及びアミノエタノール(2.00g、32.7mmol)をアセトニトリル(5mL)に溶解し、室温にて一晩撹拌した。反応液に水(100mL)を注ぎ、析出物を吸引濾過後、乾燥した。固形物をエタノール(和光純薬)及び水混合溶媒系にて再結晶することにより化合物6(収量0.43g、収率39%)を得た。また、トリフェニルクロロメタンの代わりにジフェニルクロロメタンを使用し同様の操作を行うことにより、化合物5を得ることが出来る。
<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.
<化合物6の物理恒数>
mp.94−97℃
1H-NMR(d6−DMSO):δ2.07(t、J=6.0Hz、2H)、3.51(t、J=6.0Hz、2H)、7.15−7.42(m、15H).
IR(cm-1): 3244、1488、1442、1025.
<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.
<製造例4: 化合物7及び化合物8の製造方法>
トリフェニルクロロメタン(1.00g、3.58mmol)(和光純薬)及び塩酸エタノ−ルアミン(1.00g、10.3mmol)(和光純薬)をピリジン(4mL)に溶解し、室温にて3日間撹拌した。反応液に水(200mL)を注ぎ、析出物を吸引濾過した。固形物をジエチルエ−テルに縣濁し、3(N)塩酸(和光純薬)を加え、室温にて15分間撹拌した後、不溶物を吸引濾過した。不溶物を酢酸エチル(和光純薬)及び飽和炭酸水素ナトリウム(和光純薬)水溶液の混合溶液に溶解し、振とう後、有機層を分離した。有機層を無水硫酸ナトリウム(和光純薬)にて乾燥した後、吸引濾過、減圧濃縮し、化合物8(収量0.31g、収率28%)を得た。また、トリフェニルクロロメタンの代わりにジフェニルクロロメタンを使用し同様の操作を行うことにより、化合物7を得ることが出来る。
<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.
<化合物8の物理恒数>
mp.87−89℃.
1H−NMR(CDCl3):δ2.88(t、J=5.1Hz、2H)、3.14(t、J=5.1Hz、2H)、7.24−7.51(m、15H).
IR(cm-1): 3378、1594、1448、1054.
<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.
<製造例5: 化合物9の製造方法>
クロロジフェニルメタン(0.50g、2.47mmol)(和光純薬)、ピロリジン(0.53g、7.45mmol)(東京化成)及びヨウ化カリウム(0.10g、0.60mmol)(和光純薬)をアセトニトリル(20mL)(和光純薬)に加え、2時間還流した。室温まで放却した後、反応液に飽和炭酸水素ナトリウム(和光純薬)水溶液を加え、酢酸エチル(和光純薬)にて抽出した。有機層を無水硫酸ナトリウム(和光純薬)にて乾燥し、減圧下溶媒を留去した。残留物をシリカゲルカラムクロマトグラフィ−(展開溶媒、クロロホルム(和光純薬):メタノール(和光純薬)=99:1)付し、化合物9(収量0.36g、収率61%)を得た。
<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).
<化合物9の物理恒数>
mp. 69−72℃
1H−NMR(CDCl3):δ1.73−1.79(m、4H)、2.40−2.44(m、4H)、4.15(s、1H)、7.12−7.47(m、10H).
IR(cm-1):2793、1452、703.
<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.
<製造例6: 化合物10の製造方法>
ピロリジン(0.26g、3.66mmol)(和光純薬)、トリフェニルクロロメタン(1.02g、3.66mmol)(和光純薬)及び炭酸カリウム(0.51g, 3.66mmol)(和光純薬)をアセトニトリル(30mL)(和光純薬)に加え、5時間還流した。反応液に、飽和炭酸水素ナトリウム(和光純薬)水溶液を加え、酢酸エチル(和光純薬)にて抽出した。有機層を無水硫酸ナトリウム(和光純薬)にて乾燥し、減圧下溶媒を留去した。残留物をシリカゲルカラムクロマトグラフィ−(展開溶媒n−ヘキサン(和光純薬):酢酸エチル(和光純薬)=9:1)に付し、化合物10(収量0.45g、収率80%)を得た。
<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.
<化合物10の物理恒数>
mp.127−129℃
1H−NMR(CDCl3):δ1.53−1.65(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.
<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.
<製造例7: 化合物11及び化合物12の製造方法>
ピペリジン(1.50g、17.6mmol)(和光純薬)、トリフェニルクロロメタン(5.40g、19.4mmol)(和光純薬)及び炭酸カリウム(2.68g、19.4mmol)(和光純薬)をアセトニトリル(30mL)(和光純薬)に加え、5時間還流した。反応液に、飽和炭酸水素ナトリウム(和光純薬)水溶液を加え、酢酸エチル(和光純薬)にて抽出した。有機層を無水硫酸ナトリウム(和光純薬)にて乾燥し、減圧下溶媒を留去した。得られた粗精製物をクロロホルム(和光純薬)及びn−ヘキサン(和光純薬)の混合溶媒を用いて再結晶し、化合物12(収量1.80g、収率31%)を得た。また、トリフェニルクロロメタンの代わりにジフェニルクロロメタンを使用し同様の操作を行うことにより、化合物11を得ることが出来る。
<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.
<化合物12の物理恒数>
mp.156−158℃
1H−NMR(CDCl3):δ0.70−3.50(m、10H)、7.14−7.80(m、15H).
IR(cm-1):2923、1485、1448、708.
<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.
<本発明の抗シワ剤>
本発明の組成物は、1)前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤とを含有することを特徴とする。本発明の抗シワ剤としては、シワ形成に対する予防又は改善作用を有する抗シワ剤であれば特段の限定なく適応することが出来、好ましいものとしては、ビタミンA又はその誘導体及び/又はそれらの薬理学的に許容される塩、トリテルペン酸またはトリテルペン酸誘導体及び/又はそれらの薬理学的に許容される塩、さらには、真皮コラ−ゲン線維束再構築作用を有する植物抽出物などが好適に例示出来る。本発明の抗シワ剤が有するシワ形成に対する予防又は改善作用には、既に形成されたシワに対する改善作用に加え、これから形成されるシワ、若しくは、形成過程にあるシワに対するシワ形成に対する予防又は改善作用が包含される。また、本発明の抗シワ剤が有する作用機序としては、ヒアルロン酸産生促進作用、コラ−ゲン産生促進作用、マトリックスメタロプロテア−ゼ阻害作用、真皮コラ−ゲン線維束再構築作用等を介する作用機序が想定される。前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩は、抗シワ剤と共に皮膚外用剤に配合することにより、抗シワ剤の有するシワ形成に対する予防又は改善作用を増強する作用を有する。前記のシワ形成に対する予防又は改善作用を有する何れの抗シワ剤に付いても、本発明の組成物中に含有させることが出来るが、シワ形成に対する予防又は改善効果を増強させる面から、特に好ましいものとしては、真皮コラ−ゲン線維束の崩壊あるいは構造の乱れを予防又は改善する作用を有する抗シワ剤、具体的には、トリテルペン酸及び/又はその薬理学的に許容される塩、トリテルペン酸誘導体及び/又はそれらの薬理学的に許容される塩、真皮コラ−ゲン線維束再構築作用を有する植物抽出物が好適に例示出来る。
<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.
また、本発明の抗シワ剤は、単純な化学物質、又は、当該化合物を含有する植物由来の抽出物等の形態が好適に例示出来る。ここで、植物由来の抽出物とは、植物抽出物自体、植物抽出物を分画、精製した分画、植物抽出物乃至は分画、精製物の溶媒除去物の総称を意味する。また、かかる抗シワ剤を前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と共に組成物に含有させる場合には、前述した抗シワ剤を唯1種のみを含有させることも出来るし、2種以上を組み合わせて含有させることも出来る。 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.
本発明の抗シワ剤に関し、特に好ましいものを挙げれば、ビタミンA、その誘導体及び/又はそれらの薬理学的に許容される塩、トリテルペン酸、その酸誘導体及び/又はそれらの薬理学的に許容される塩、真皮コラ−ゲン線維束再構築作用を有する植物抽出物などが好適に例示出来る。前記ビタミンA、その誘導体及び/又はそれらの薬理学的に許容される塩の内、好ましいものとしては、レチノ−ル、その誘導体及び/又はその薬理学的に許容される塩、レチナ−ル、その誘導体及び/又はそれらの薬理学的に許容される塩、レチノイン酸、その誘導体及び/又はそれらの薬理学的に許容される塩などが好適に例示出来、さらに好ましいものを具体的に例示すれば、レチノ−ル、その誘導体及び/又はそれらの薬理学的に許容される塩としては、レチノ−ル、酢酸レチノ−ル、プロピオン酸レチノ−ル、酪酸レチノ−ル、オクチル酸レチノ−ル、ラウリル酸レチノ−ル、パルミチン酸レチノ−ル、ステアリン酸レチノ−ル、ミリスチン酸レチノ−ル、オレイン酸レチノ−ル、リノレン酸レチノ−ル、リノ−ル酸レチノ−ル等のレチノ−ル脂肪酸エステル及び/又はそれらの薬理学的に許容される塩等が好適に例示出来、レチナ−ル、その誘導体及び/又はそれらの薬理学的に許容される塩としては、レチナ−ル及び/又はその薬理学的に許容される塩が好適に例示出来、レチノイン酸、その誘導体及び/又はそれらの薬理学的に許容される塩としては、レチノイン酸、トレチノイン(オ−ルトランスレチノイン酸)、イソトレチノイン(13−シス−レチノイン酸)、レチノイン酸メチル、レチノイン酸エチル、レチノイン酸レチノ−ル、レチノイン酸トコフェリル(トコフェリル残基は、α、β、γ、δのいずれの化学構造を有していてもよい)及び/又はそれらの薬理学的に許容される塩が好適に例示出来、さらに好ましくは、レチノ−ル、レチナ−ル、レチノイン酸、トレチノイン、イソトレチノイン、レチノイン酸トコフェリル、パルミチン酸レチノ−ル、酢酸レチノ−ル及び/又はそれらの薬理学的に許容される塩が好適に例示出来、これらの内、さらに好ましいものとしては、レチノ−ル、酢酸レチノ−ル、レチノイン酸トコフェリル及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。また、本発明において使用するビタミンA誘導体及び/又はそれらの薬理学的に許容される塩は、例えば、シグマアルドリッチ社などの試薬販売メ−カ−より購入し、使用することが出来る。 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.
さらに、前記のトリテルペン酸、その誘導体及び/又はそれらの薬理学的に許容される塩としては、化粧料などに分野で使用されているものであれば特段の限定なく適応することが出来、好ましいトリテルペン酸の具体例を挙げれば、ウルソ−ル酸、オレアノ−ル酸、ベツリン酸等が好適に例示出来、ウルソ−ル酸が特に好ましい。また、トリテルペン酸誘導体としては、トリテルペン酸の炭素数1〜20の脂肪族炭化水素エステル、トリテルペン酸の芳香族基により置換されている炭素数1〜4の炭化水素エステル、トリテルペン酸のリン酸エステル及び/又はそれらの薬理学的に許容される塩が好適に例示出来る。前記炭素数1〜20の脂肪族炭化水素エステルとしては、メチルエステル、エチルエステル、ヘキシルエステル、シクロヘキシルエステル、オクチルエステル、イソオクチルエステル、ラウリルエステル、セチルエステル、ステアリルエステル、イソステアリルエステル、オレイルエステル等の脂肪族エステルが好適に例示出来る。また、前記の芳香族基により置換されている炭素数1〜4の炭化水素エステルとしては、ベンジルエステル、フェニルエチルエステル、フェニルプロピルエステル、フェニルブチルエステル等が好適に例示出来、ベンジルエステルが特に好ましい。前述した抗シワ剤の内、特に好ましいものとしては、ウルソ−ル酸及び/又はその薬理学的に許容される塩、ウルソ−ル酸ベンジル及び/又はその薬理学的に許容される塩(例えば、特開2000−302659号公報を参照)、ウルソ−ル酸リン酸エステル及び/又はその薬理学的に許容される塩好適に例示出来る。前述した本発明の抗シワ剤は、前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と共に組成物に含有させることにより、美肌作用、取り分け、シワ形成に対する予防又は改善作用が増強される。 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.
前記の抗シワ剤は、以下に示す方法により合成することも出来るし、市販の試薬等として購入することも出来る。前記の抗シワ剤の内、トリテルペン酸の炭素数1〜20の脂肪族炭化水素エステル、トリテルペン酸の芳香族基により置換されている炭素数1〜4の炭化水素エステルは、相当するトリテルペン酸を水素化ナトリウムにて処理しナトリウム塩とした後、これにハロゲン化炭化水素を加え反応させることにより得ることが出来る。反応温度及び時間は、室温乃至は還流条件下、1〜12時間反応を行えばよい。また、前記トリテルペン酸のリン酸エステルに付いては、例えば、再表2006−132033号公報に記載の方法に従い、トリテルペン酸より誘導することが出来る。具体的には、トリテルペン酸リン酸エステルは、市販のトリテルペン酸をテトラゾ−ル存在下、1〜3倍当量のジメチル−N,N−ジエチルホスホロアミデ−トと処理し、t−ブチルハイドロパ−オキシドを反応させ、トリテルペン酸のメチルホスフェ−トとした後、更に、トリメチルシリルブロミドを作用させることにより合成することができる。 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.
前記の抗シワ剤は、そのまま抗シワ剤として使用することも出来るが、薬理学的に許容される酸又は塩基と共に処理し塩の形に変換し、塩として使用することも可能である。例えば、塩酸塩、硫酸塩、硝酸塩、リン酸塩、炭酸塩などの鉱酸塩、マレイン酸塩、フマル酸塩、シュウ酸塩、クエン酸塩、乳酸塩、酒石酸塩、メタンスルホン酸塩、パラトルエンスルホン酸塩、ベンゼンスルホン酸塩などの有機酸塩、ナトリウム塩、カリウム塩等のアルカリ金属、カルシウム塩、マグネシウム塩等のアルカリ土類金属、トリエチルアミン塩、トリエタノ−ルアミン塩、アンモニウム塩、モノエタノ−ルアミン塩、ピペリジン塩等の有機アミン塩、リジン塩、アルギン酸塩等の塩基性アミノ酸塩などが好適に例示出来る。 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.
また、本発明の抗シワ剤の内、真皮コラ−ゲン線維束再構築作用を有する植物抽出物に付いて述べる。本発明の真皮コラ−ゲン線維束再構築作用を有する成分としては、フトモモ科フトモモ属チョウジノキより得られる植物抽出物、オトギリソウ科オトギリソウより得られる植物抽出物、オトギリソウ科セイヨウオトギリソウより得られる植物抽出物、オトギリソウ科ヒメオトギリより得られる植物抽出物、オトギリソウ科トモエソウより得られる植物抽出物、カシノキ科キリンツケヤシより得られる植物抽出物、オミナエシ科オトコエシより得られる植物抽出物、バラ科ビワより得られる植物抽出物、バラ科モモより得られる植物抽出物、クロウメモドキ科ナツメより得られる植物抽出物、スイカズラ科セイヨウニワトコより得られる植物抽出物、キク科ヤグルマギクより得られる植物抽出物、シソ科タイムより得られる植物抽出物、シソ科ロ−ズマリ−より得られる植物抽出物、シソ科セ−ジより得られる植物抽出物、シソ科シソより得られる植物抽出物、シソ科オドリコソウより得られる植物抽出物、シソ科セイヨウハッカより得られる植物抽出物などが好適に例示出来、これらの内、さらに好ましいものとしては、フトモモ科フトモモ属チョウジノキより得られる植物抽出物、オトギリソウ科オトギリソウより得られる植物抽出物、オトギリソウ科セイヨウオトギリソウより得られる植物抽出物、オトギリソウ科ヒメオトギリより得られる植物抽出物、オトギリソウ科トモエソウより得られる植物抽出物、スイカズラ科セイヨウニワトコより得られる植物抽出物、キク科ヤグルマギクより得られる植物抽出物、シソ科ロ−ズマリ−より得られる植物抽出物が好適に例示出来る。前記の真皮コラ−ゲン線維束再構築作用を有する成分は、前記一般式(1)に表される化合物、その異性体及び/又はそれらの薬理学的に許容される塩と共に、組成物に含有させることにより、美肌作用、取り分け、シワ形成に対する予防又は改善作用が増強される。 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.
本発明の真皮コラ−ゲン線維束再構築作用を有する植物抽出物は、真皮コラ−ゲン線維束再構築作用を有する植物抽出物であれば、特段の限定なく適応すること出来る。本発明における植物抽出物とは、植物体それ自身、植物体を乾燥、細切、粉砕など加工した加工物、植物体乃至はその加工物に溶媒を加えて抽出した溶媒抽出物、抽出物から溶媒を除去した抽出物の溶媒除去物、それらをカラムクロマトグラフィ−や液液抽出など精製した精製物などの総称を意味する。本発明の植物抽出物に適用する植物としては、フトモモ科フトモモ属チョウジノキ、オトギリソウ科オトギリソウ、オトギリソウ科セイヨウオトギリソウ、オトギリソウ科ヒメオトギリ、オトギリソウ科トモエソウ、カシノキ科キリンツケヤシ、オミナエシ科オトコエシ、バラ科ビワ、バラ科モモ、クロウメモドキ科ナツメ、スイカズラ科セイヨウニワトコ、キク科ヤグルマギク、シソ科タイム、シソ科ロ−ズマリ−、シソ科セ−ジ、シソ科シソ、シソ科オドリコソウ、シソ科セイヨウハッカ等が好ましく例示出来、これらの内、特に、フトモモ科フトモモ属チョウジノキ、オトギリソウ科オトギリソウ、オトギリソウ科セイヨウオトギリソウ、オトギリソウ科ヒメオトギリ、オトギリソウ科トモエソウ、スイカズラ科セイヨウニワトコ、キク科ヤグルマギク、シソ科ロ−ズマリ−が好適に例示出来る。本発明の植物抽出物の調製に用いる植物体の部位としては、植物体のいずれの部位も使用できるが、特に好ましいものは全草を乾燥したものである。これはこの部位に真皮コラ−ゲン線維束を再構築する成分が多く含まれているためである。又、本発明の植物抽出物としては、極性溶媒抽出物或いはその溶媒除去物が特に好ましく例示出来、極性溶媒としては、エタノ−ルやメタノ−ルなどのアルコ−ル類、酢酸エチルや蟻酸メチルなどのエステル類、アセトンやメチルエチルケトン等のケトン類、ジエチルエ−テルやテトラヒドロフランなどのエ−テル類、クロロホルムや塩化メチレン等のハロゲン化炭化水素類、水等から選ばれる1種乃至は2種以上が好ましく例示できる。これらの内、特に好ましいものは、水及びアルコ−ルから選ばれる1種乃至は2種以上である。この様な抽出物乃至はその溶媒除去物は、植物体乃至はその加工物に1〜10倍量の溶媒を加え、室温であれば数日間、沸点付近の温度であれば、数時間浸漬すればよい。溶媒除去は、蒸発乾固、減圧濃縮、凍結乾燥いずれも可能である。もっとも好ましいものは減圧濃縮と凍結乾燥である。 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.
本発明の組成物の抗シワ剤は、唯一種を含有させることもできるし、二種以上を含有させることも出来る。また、本発明の組成物中における好ましい含有量としては、0.00001〜15重量%、より好ましくは、0.0001質量%〜10質量%、さらに好ましくは、0.001質量%〜5質量%、さらに好ましくは、0.01%〜3量%含有することが好ましい。これは、少なすぎると効果を発揮しない場合があり、多すぎても効果が頭打ちになり、処方の自由度が損なわれる場合があるからである。 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.
<製造例8:フトモモ科チョウジノキより得られる植物抽出物の製造方法>
フトモモ科チョウジノキの花蕾を乾燥させたもの500(g)に5(L)のメタノ−ルを加え、室温で1週間浸漬し、濾過して、減圧濃縮し、本発明のフトモモ科チョウジノキより得られる植物抽出物35(g)得た。
<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.
<製造例9:オトギリソウ科オトギリソウより得られる植物抽出物の製造方法>
オトギリソウ科オトギリソウの全草を乾燥したもの500(g)に5(L)のメタノ−ルを加え、室温で1週間浸漬し、濾過して、減圧濃縮し、本発明のオトギリソウ科オトギリソウより得られる植物抽出物を22g得た。同様の手順に従い、オトギリソウ科セイヨウオトギリソウより得られる植物抽出物、オトギリソウ科ヒメオトギリより得られる植物抽出物、オトギリソウ科トモエソウより得られる植物抽出物を得た。
<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.
<製造例10:スイカズラ科セイヨウニワトコより得られる植物抽出物の製造方法>
スイカズラ科セイヨウニワトコの花1(kg)に10(L)のエタノ−ルを加え2時間還流させ、濾過し濾液を取り、これを水3(L)に一気に加え析出した沈殿を濾取し、本発明のスイカズラ科セイヨウニワトコより得られる植物抽出物19(g)を得た。
<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.
<製造例11:キク科ヤグルマギクより得られる植物抽出物の製造方法>
キク科ヤグルマギクの全草1(kg)に10(L)のエタノ−ルを加え2時間還流させ、濾過し濾液を取り、これを水3(L)に一気に加え析出した沈殿を濾取し、本発明のキク科ヤグルマギクより得られる植物抽出物12(g)を得た。
<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.
<製造例12:シソ科ロ−ズマリ−より得られる植物抽出物の製造方法>
ロ−ズマリ−1(kg)に10(L)のエタノ−ルを加え2時間還流させ、濾過し濾液を取り、これを減圧濃縮し粗抽出物1 213(g)得た。粗抽出物1 100(g)を600(mL)のエタノ−ルに溶解させ、これを水200(mL)に一気に加え析出した沈殿を濾取し42gの粗抽出物2を得た。粗抽出物2の100(g)を500(mL)のノルマルブタノ−ルに溶解させ、500(mL)の水を加え液液抽出し、ブタノ−ル相を取った。この作業を3回繰り返し、ブタノ−ル相を合わせて減圧濃縮し本発明のシソ科ロ−ズマリ−より得られる植物抽出物27(g)得た。
<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.
<本発明の組成物>
本発明の組成物は、1)前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤を含有することを特徴とする。本発明の前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩は、前記の抗シワ剤と共に組成物に含有させることにより、美肌作用、取り分け、シワ形成に対する予防又は改善作用の増強効果を示す。本発明における美肌作用は、年齢と共に顕在化する肌の美観に関する皮膚老化現象に対する予防又は改善作用を意味し、シワ形成に対する予防又は改善作用が好適に例示出来、具体例を挙げれば、既に形成されたシワを目立たなくする改善作用などに加え、これから形成され顕在化するシワ、たるみなどの皮膚症状に対する予防又は改善作用などが好適に例示出来る。本発明の組成物が有する美肌作用の内、好ましいものを具体的に例示すれば、後述する「本発明のシワ改善作用評価」において、比較用の組成物(皮膚外用剤)に対し、シワ改善作用を示す成分が好適に例示出来る。また、本発明の組成物には、シワ形成に対する予防又は改善作用に加え、日焼け、シミ、くすみ等の色素沈着に起因する肌症状に対する予防又は改善作用等が存するため、総合的な肌状態を予防又は改善作用を期待することが出来る。
<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.
また、1)前記一般式(1)に表される化合物及び/又はそれらの薬理学的に許容される塩と、2)抗シワ剤を含有することを特徴とする組成物の製剤化にあたっては、通常の食品、医薬品、化粧料などの製剤化で使用される任意成分を含有することが出来る。この様な任意成分としては、経口投与組成物であれば、例えば、乳糖や白糖などの賦形剤、デンプン、セルロ−ス、アラビアゴム、ヒドロキシプロピルセルロ−スなどの結合剤、カルボキシメチルセルロ−スナトリウム、カルボキシメチルセルロ−スカルシウムなどの崩壊剤、大豆レシチン、ショ糖脂肪酸エステルなどの界面活性剤、マルチト−ルやソルビト−ルなどの甘味剤、クエン酸などの酸味剤、リン酸塩などの緩衝剤、シェラックやツェインなどの皮膜形成剤、タルク、ロウ類などの滑沢剤、軽質無水ケイ酸、乾燥水酸化アルミニウムゲルなどの流動促進剤、生理食塩水、ブドウ糖水溶液などの希釈剤、矯味矯臭剤、着色剤、殺菌剤、防腐剤、香料など好適に例示出来る。 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.
本発明の組成物としては、医薬品、化粧品、食品、飲料などが好適に例示出来、日常的に摂取出来ることから、食品、化粧品などに適応することが好ましい。その投与経路も、経口投与、経皮投与の何れもが可能であり、解毒(デトックス)の目的では、関連臓器への到達効率のよい経口投与を採用し、食品などの経口投与組成物の形態を採用することが好ましい。また、かかる成分が連続投与される場合、さらには安全性を考慮した場合、経皮的に投与されることが好ましい。皮膚に外用で適応されるものであれば特段の限定なく応用出来、例えば、医薬部外品を含む化粧料、皮膚外用医薬、皮膚外用雑貨等が好ましく例示できる。本発明の皮膚外用剤としては、皮膚に外用で適用されるものであれば、特段の限定無く使用することができ、例えば、化粧料、皮膚外用医薬、皮膚外用雑貨などが好適に例示でき、化粧料に適用することが特に好ましい。これは本発明の皮膚外用剤が、比類無き使用感の良さを有しているため、使用感が重要な化粧料に特に好適であるためである。化粧料としては、水中油乳化剤形を応用できるものであれば、特段の限定はなく、例えば、エッセンス、乳液、クリ−ム等の基礎化粧料、アンダ−メ−クアップ、ファンデ−ション、チ−クカラ−、マスカラ、アイライナ−などのメークアップ化粧料、ヘアクリ−ムなどの毛髪化粧料などが好適に例示できる。 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.
本発明の皮膚外用剤においては、かかる成分以外に、通常皮膚外用剤で使用される任意成分を含有することが出来る。この様な任意成分としては、例えば、マカデミアナッツ油、アボガド油、トウモロコシ油、オリ−ブ油、ナタネ油、ゴマ油、ヒマシ油、サフラワ−油、綿実油、ホホバ油、ヤシ油、パ−ム油、液状ラノリン、硬化ヤシ油、硬化油、モクロウ、硬化ヒマシ油、ミツロウ、キャンデリラロウ、カルナウバロウ、イボタロウ、ラノリン、還元ラノリン、硬質ラノリン、ホホバロウ等のオイル、ワックス類;流動パラフィン、スクワラン、プリスタン、オゾケライト、パラフィン、セレシン、ワセリン、マイクロクリスタリンワックス等の炭化水素類;オレイン酸、イソステアリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘン酸、ウンデシレン酸等の高級脂肪酸類;セチルアルコ−ル、ステアリルアルコ−ル、イソステアリルアルコ−ル、ベヘニルアルコ−ル、オクチルドデカノ−ル、ミリスチルアルコ−ル、セトステアリルアルコ−ル等の高級アルコール等;イソオクタン酸セチル、ミリスチン酸イソプロピル、イソステアリン酸ヘキシルデシル、アジピン酸ジイソプロピル、セバチン酸ジ−2−エチルヘキシル、乳酸セチル、リンゴ酸ジイソステアリル、ジ−2−エチルヘキサン酸エチレングリコ−ル、ジカプリン酸ネオペンチルグリコール、ジ−2−ヘプチルウンデカン酸グリセリン、トリ−2−エチルヘキサン酸グリセリン、トリ−2−エチルヘキサン酸トリメチロ−ルプロパン、トリイソステアリン酸トリメチロ−ルプロパン、テトラ−2−エチルヘキサン酸ペンタンエリトリット等の合成エステル油類;ジメチルポリシロキサン、メチルフェニルポリシロキサン、ジフェニルポリシロキサン等の鎖状ポリシロキサン;オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサンシロキサン等の環状ポリシロキサン;アミノ変性ポリシロキサン、ポリエ−テル変性ポリシロキサン、アルキル変性ポリシロキサン、フッ素変性ポリシロキサン等の変性ポリシロキサン等のシリコーン油等の油剤類;脂肪酸セッケン(ラウリン酸ナトリウム、パルミチン酸ナトリウム等)、ラウリル硫酸カリウム、アルキル硫酸トリエタノ−ルアミンエ−テル等のアニオン界面活性剤類;塩化ステアリルトリメチルアンモニウム、塩化ベンザルコニウム、ラウリルアミンオキサイド等のカチオン界面活性剤類;イミダゾリン系両性界面活性剤(2−ココイル−2−イミダゾリニウムヒドロキサイド−1−カルボキシエチロキシ2ナトリウム塩等)、ベタイン系界面活性剤(アルキルベタイン、アミドベタイン、スルホベタイン等)、アシルメチルタウリン等の両性界面活性剤類;ソルビタン脂肪酸エステル類(ソルビタンモノステアレ−ト、セスキオレイン酸ソルビタン等)、グリセリン脂肪酸類(モノステアリン酸グリセリン等)、プロピレングリコール脂肪酸エステル類(モノステアリン酸プロピレングリコ−ル等)、硬化ヒマシ油誘導体、グリセリンアルキルエ−テル、POEソルビタン脂肪酸エステル類(POEソルビタンモノオレエ−ト、モノステアリン酸ポリオキエチレンソルビタン等)、POEソルビット脂肪酸エステル類(POE−ソルビットモノラウレ−ト等)、POEグリセリン脂肪酸エステル類(POE−グリセリンモノイソステアレ−ト等)、POE脂肪酸エステル類(ポリエチレングリコ−ルモノオレ−ト、POEジステアレ−ト等)、POEアルキルエ−テル類(POE2−オクチルドデシルエ−テル等)、POEアルキルフェニルエ−テル類(POEノニルフェニルエ−テル等)、プルロニック型類、POE・POPアルキルエ−テル類(POE・POP2−デシルテトラデシルエ−テル等)、テトロニック類、POEヒマシ油・硬化ヒマシ油誘導体(POEヒマシ油、POE硬化ヒマシ油等)、ショ糖脂肪酸エステル、アルキルグルコシド等の非イオン界面活性剤類;ピロリドンカルボン酸ナトリウム、乳酸、乳酸ナトリウム等の保湿成分類;表面を処理されていても良い、マイカ、タルク、カオリン、合成雲母、炭酸カルシウム、炭酸マグネシウム、無水ケイ酸(シリカ)、酸化アルミニウム、硫酸バリウム等の粉体類、;表面を処理されていても良い、ベンガラ、黄酸化鉄、黒酸化鉄、酸化コバルト、群青、紺青、酸化チタン、酸化亜鉛の無機顔料類;表面を処理されていても良い、雲母チタン、魚燐箔、オキシ塩化ビスマス等のパ−ル剤類;レ−キ化されていても良い赤色202号、赤色228号、赤色226号、黄色4号、青色404号、黄色5号、赤色505号、赤色230号、赤色223号、橙色201号、赤色213号、黄色204号、黄色203号、青色1号、緑色201号、紫色201号、赤色204号等の有機色素類;ポリエチレン末、ポリメタクリル酸メチル、ナイロン粉末、オルガノポリシロキサンエラストマ−等の有機粉体類;パラアミノ安息香酸系紫外線吸収剤;アントラニル酸系紫外線吸収剤;サリチル酸系紫外線吸収剤、;桂皮酸系紫外線吸収剤、;ベンゾフェノン系紫外線吸収剤;糖系紫外線吸収剤;2−(2’−ヒドロキシ−5’−t−オクチルフェニル)ベンゾトリアゾ−ル、4−メトキシ−4’−t−ブチルジベンゾイルメタン等の紫外線吸収剤類;エタノ−ル、イソプロパノ−ル等の低級アルコール類;ビタミンA又はその誘導体、ビタミンB6塩酸塩、ビタミンB6トリパルミテ−ト、ビタミンB6ジオクタノエ−ト、ビタミンB2又はその誘導体、ビタミンB12、ビタミンB15又はその誘導体等のビタミンB類;α−トコフェロ−ル、β−トコフェロ−ル、γ−トコフェロ−ル、ビタミンEアセテ−ト等のビタミンE類、ビタミンD類、ビタミンH、パントテン酸、パンテチン、ピロロキノリンキノン等のビタミン類等;フェノキシエタノ−ル等の抗菌剤;ヘクトライト、ジメチルジステアリルアンモニウム変性ヘクトライトなどの有機変性粘土鉱物などが好ましく例示できる。 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.
本発明の皮膚外用剤は前記の必須成分を含有し、好ましくは、乳化剤形をとる。乳化剤形の形態としては、油中水乳化剤形でも、水中油乳化剤形でも構わないが、水中油乳化剤形が特に好ましい。ここで、油中水乳化剤形とは外相に油相を有する乳化剤形を総合して称する言葉であり、内相に水相を含有していても良いし、水中油エマルションなどの乳化物を有していても良い。同様に水中油乳化剤形とは、外相に水相を有する乳化物の総称であり、内相に油相を有していても良いし、油中水エマルションなどの乳化物を有していても良い。 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.
本発明の皮膚外用剤においては、通常の化粧料などの皮膚外用剤で使用されている非界面活性剤を含有することが出来る。更に、乳化状態を安定に保つ意味でアルキル変性カルボキシビニルポリマ−及び/又はその塩を含有させることも好ましい。かかる成分の好ましい含有量は、皮膚外用剤全量に対して、0.01〜0.5質量%であり、より好ましくは0.05〜0.3質量%である。かかる成分は、皮膚に投与後前記必須成分であるアモジメチコンと複合膜を作り、アモジメチコンの効果を増強させるので、その意味でも含有することが好ましい。かかるアルキル変性カルボキシビニルポリマ−には市販品が存し、かかる市販品を購入して使用することが出来る。好ましい市販品としては、日本サ−ファクタント工業株式会社から市販され、炭素数10〜30のアルキル基でアルキル変性されている「ペムレン(PEMUREN;登録商標)TR−1」、「ペムレン(PEMUREN;登録商標)TR−2」、BFグッドリッチ社(米)から市販されている「カ−ボポ−ル(CARBOPOL;登録商標)1382」などがあり、アルキル変性されていないカルボキシビニルポリマ−としては、BFグッドリッチ社(米)から市販されている「カ−ボポ−ル(CARBOPOL;登録商標)Ultrez10」、「カ−ボポ−ル(CARBOPOL;登録商標)940」などがある。このような親水性高分子は、唯一種を用いても、二種以上を組み合わせて用いても構わない。本発明の水中油型乳化組成物は、このような親水性高分子を、0.05〜1質量%含有することが好ましく、0.08〜0.5質量%含有することがより好ましい。これより少ないと乳化系が不安定化するし、これより多いと系の粘度が高くなりすぎて、塗布性が悪くなる。また、この様なアルキル変性カルボキシビニルポリマ−及び/又はその塩を含有させる場合、かかるポリマ−が作り出す乳化構造を強化する意味で、グリセリルアルキルエ−テル、若しくは、グリセリルアルケニルエ−テルを含有させることが好ましい。グリセリルアルキルエ−テルとしては、バチルアルコ−ルが、グリセリルアルケニルエ−テルとしては、セラキルアルコ−ルが好適に例示出来る。かかるエ−テル類は、0.1質量%〜1質量%含有させることが好ましく、かかる含有量は、アルキル変性カルボキシビニルポリマ−の含有量と等量乃至は5倍量であることが好ましい。この量範囲が、乳化剤形を強化するのに好適であるためである。 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.
また、前記の任意成分の中で特に好ましいものとしては、非イオン界面活性剤であり、中でも、親油性の界面活性剤であって、乳化状態に於いて構造形成性に優れるもの好ましく、かかる非イオン界面活性剤としては、ソルビタンステアリン酸エステル、グリセリンモノステアリン酸エステルなどが特に好適に例示できる。かかる成分の好ましい含有量は0.1〜5質量%であり、より好ましくは0.2〜3質量%である。かかる成分を加えることにより、皮膚との接着性に優れるようになる。 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.
本発明の皮膚外用剤は、前記の任意成分や必須成分を常法に従って処理することにより製造することが出来る。 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.
以下に、実施例を挙げて、更に詳細に本発明について説明を加える。
Hereinafter, the present invention will be described in more detail with reference to examples.
<製造例13: 本発明の組成物(皮膚外用剤)の製造1>
表1及び表2に示す処方に従って、本発明の組成物(皮膚外用剤)を作製した。即ち、イ、ロ及びハの成分を80℃に加熱し、ロにハを攪拌しながら徐々に加え中和した後、イを徐々に攪拌しながら加え、ホモミキサ−により乳化粒子を均一化し乳液(化粧料1〜12)を得た。同様の操作により、「本発明の前記一般式(1)に表される化合物」を「水」に置換した比較例1、「本発明の抗シワ剤」を「水」に置換した比較例2、「本発明の前記一般式(1)に表される化合物」及び「本発明の抗シワ剤」を共に「水」に置換した比較例3を製造した。
<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”.
<試験例1: 本発明のシワ改善作用評価1>
実施例1に記載の方法に従い作製された化粧料1〜12、比較例1〜3を用い、以下の方法に従いシワ改善効果を調べた。即ち、目尻のシワが気になるパネラ−120名(女性、年齢層40〜60歳)を8名ずつ15群に分け、各群に対しそれぞれ化粧料1〜12、比較例1〜3を渡し、1日朝晩2回、連日8週間使用してもらい、試験の前後の目尻のレプリカの比較からシワ改善効果を調べた。レプリカは、光を透過させない白色のものを用い、これに皮膚表面形態をうつしとり、このレプリカを実体顕微鏡の標本台に固定し、45度の角度で光を照射し、レプリカを回転させて、皮溝の陰影が強く観察される方向の陰影画像(1×1cm2)を画像解析装置に取り込んだ。この画像はシワの凹凸に従って、シワの深いところは輝度が低く、シワのないところは輝度が高く、陰影を形成する。陰影画像における輝度の分布を求め、輝度のメジアン値を境に、メジアン値以上の輝度の輝点は最大輝度に、メジアン値未満の輝度の輝点は輝度0に変換して、二値化を行い、陰影部分(輝度0の部分)の面積率を求めた。(試験前の陰影の面積率−試験後の陰影の面積率)/(試験前の陰影の面積率)×100でシワ改善度(%)を求めた。結果を各群8名の平均値±標準偏差として表3に示す。表3の結果より、本発明の化粧料1〜12は、優れたシワ改善作用を有することがわかる。
<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.
<製造例14: 本発明の皮膚外用剤の製造方法2>
実施例1に記載の化粧料9に関し、「本発明の前記一般式(1)に表される化合物(化合物12)」及び「本発明の抗シワ剤(ウルソ−ル酸リン酸エステル)」を表4に示した濃度に変更した化粧料13〜16を作製した。前記成分の増減により変化した質量%は、皮膚外用剤の成分中の「水」の質量%を変更することにより調整した。
<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.
<試験例2: 本発明のシワ改善作用評価2>
実施例1に記載の化粧料5、比較例3、実施例3に記載の処方成分を有する化粧料13〜16に付いて、実施例2に記載の評価方法に従いシワ改善作用を評価した。結果を表5に示す。表5の結果より、本発明の化粧料5、化粧料13〜15は、優れたシワ改善効果を有することがわかる。
<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.
<製造例9: 本発明の皮膚外用剤の製造方法3>
実施例1に記載の化粧料5の処方成分中、「ペムレンTR−2」をPOE(25)ステアリン酸に置換した化粧料17の作製を試みたところ、化粧料25は製造直後に分離しており、乳化物が得られなかった。
<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.
<製造例10: 本発明の健康食品の製造>
表6及び表7に示す処方に従い、健康食品(健康食品1〜8)を作製した。即ち、処方成分を10重量部の水と共に転動相造粒(不二パウダル株式会社製「ニュ−マルメライザ−」)し、打錠して錠剤状の健康食品を得た。尚、表中の数値の単位は、重量部を表す。本健康食品は、優れたシワ改善作用を有していた。
<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.
本発明の組成物は、シワ改善用の化粧料、食品等に応用することが出来る。 The composition of the present invention can be applied to wrinkle-improving cosmetics, foods, and the like.
Claims (30)
[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. 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.
[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. ]
[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。] 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.
[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. ]
[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。] 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.
[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. ]
[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。] 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.
[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. ]
[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。] 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.
[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. ]
[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。] 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.
[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. ]
<真皮コラ−ゲン線維束再構築作用を有する植物抽出物>
フトモモ科フトモモ属チョウジノキより得られる植物抽出物、オトギリソウ科オトギリソウより得られる植物抽出物、オトギリソウ科セイヨウオトギリソウより得られる植物抽出物、オトギリソウ科ヒメオトギリより得られる植物抽出物、オトギリソウ科トモエソウより得られる植物抽出物、スイカズラ科セイヨウニワトコより得られる植物抽出物、キク科ヤグルマギクより得られる植物抽出物、シソ科ロ−ズマリ−より得られる植物抽出物 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
<真皮コラ−ゲン線維束再構築作用を有する植物抽出物>
フトモモ科フトモモ属チョウジノキより得られる植物抽出物、オトギリソウ科オトギリソウより得られる植物抽出物、オトギリソウ科セイヨウオトギリソウより得られる植物抽出物、オトギリソウ科ヒメオトギリより得られる植物抽出物、オトギリソウ科トモエソウより得られる植物抽出物、スイカズラ科セイヨウニワトコより得られる植物抽出物、キク科ヤグルマギクより得られる植物抽出物、シソ科ロ−ズマリ−より得られる植物抽出物 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
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CN111803396A (en) * | 2020-06-30 | 2020-10-23 | 黑龙江省医院 | Cosmetic composition based on retinaldehyde and glycylglycine oleamide and preparation method thereof |
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JPH1121225A (en) * | 1997-06-27 | 1999-01-26 | Tanabe Seiyaku Co Ltd | Ingredient for beautifying and whitening and skin preparation for external use for beautifying and whitening containing the same ingredient |
JP2004131403A (en) * | 2002-10-09 | 2004-04-30 | Pola Chem Ind Inc | Skin care preparation for external use |
JP2005306831A (en) * | 2004-04-20 | 2005-11-04 | Sakamoto Yakusoen:Kk | Skin care preparation for external use |
JP2006219449A (en) * | 2005-02-14 | 2006-08-24 | Lion Corp | Hair shampoo composition |
JP2008081505A (en) * | 2007-11-02 | 2008-04-10 | Rohto Pharmaceut Co Ltd | External preparation for skin |
JP2009234951A (en) * | 2008-03-26 | 2009-10-15 | Univ Kanagawa | Cosmetic and method for producing the same |
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JPH1121225A (en) * | 1997-06-27 | 1999-01-26 | Tanabe Seiyaku Co Ltd | Ingredient for beautifying and whitening and skin preparation for external use for beautifying and whitening containing the same ingredient |
JP2004131403A (en) * | 2002-10-09 | 2004-04-30 | Pola Chem Ind Inc | Skin care preparation for external use |
JP2005306831A (en) * | 2004-04-20 | 2005-11-04 | Sakamoto Yakusoen:Kk | Skin care preparation for external use |
JP2006219449A (en) * | 2005-02-14 | 2006-08-24 | Lion Corp | Hair shampoo composition |
JP2008081505A (en) * | 2007-11-02 | 2008-04-10 | Rohto Pharmaceut Co Ltd | External preparation for skin |
JP2009234951A (en) * | 2008-03-26 | 2009-10-15 | Univ Kanagawa | Cosmetic and method for producing the same |
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Publication number | Priority date | Publication date | Assignee | Title |
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CN111803396A (en) * | 2020-06-30 | 2020-10-23 | 黑龙江省医院 | Cosmetic composition based on retinaldehyde and glycylglycine oleamide and preparation method thereof |
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