JP6246993B2 - 皮膚外用剤 - Google Patents

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Publication number

JP6246993B2

JP6246993B2 JP2011248310A JP2011248310A JP6246993B2 JP 6246993 B2 JP6246993 B2 JP 6246993B2 JP 2011248310 A JP2011248310 A JP 2011248310A JP 2011248310 A JP2011248310 A JP 2011248310A JP 6246993 B2 JP6246993 B2 JP 6246993B2

Authority

JP

Japan

Prior art keywords

group

methyl

compound

skin

external preparation

Prior art date

2011-11-14

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.)

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• 238000002360 preparation method Methods 0.000 title claims description 130
• 230000000699 topical effect Effects 0.000 title claims description 7
• -1 piperazino group Chemical group 0.000 claims description 266
• 150000001875 compounds Chemical class 0.000 claims description 173
• 150000003839 salts Chemical class 0.000 claims description 86
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 69
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
• 125000004432 carbon atom Chemical group C* 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 53
• 239000002537 cosmetic Substances 0.000 claims description 48
• 239000000419 plant extract Substances 0.000 claims description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 230000002087 whitening effect Effects 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 241000196324 Embryophyta Species 0.000 claims description 33
• 125000004122 cyclic group Chemical group 0.000 claims description 30
• MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical class C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims description 25
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 23
• 235000018185 Betula X alpestris Nutrition 0.000 claims description 21
• 235000018212 Betula X uliginosa Nutrition 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• 125000006267 biphenyl group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 16
• DJMXWKUBTGMKCG-UHFFFAOYSA-N 1-benzhydrylpyrrolidine Chemical compound C1CCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 DJMXWKUBTGMKCG-UHFFFAOYSA-N 0.000 claims description 13
• 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 13
• 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 13
• 229940079593 drug Drugs 0.000 claims description 13
• 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 12
• 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 12
• 235000010290 biphenyl Nutrition 0.000 claims description 12
• 239000004305 biphenyl Substances 0.000 claims description 12
• 229940125904 compound 1 Drugs 0.000 claims description 12
• 229940125773 compound 10 Drugs 0.000 claims description 12
• 229940125797 compound 12 Drugs 0.000 claims description 12
• 229940125782 compound 2 Drugs 0.000 claims description 12
• 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 12
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
• 229940126214 compound 3 Drugs 0.000 claims description 11
• 229940125898 compound 5 Drugs 0.000 claims description 11
• 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 10
• 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 9
• 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 8
• MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 claims description 8
• 241000758791 Juglandaceae Species 0.000 claims description 8
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• LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims description 8
• 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 7
• 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 7
• 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 7
• 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
• 235000001453 Glycyrrhiza echinata Nutrition 0.000 claims description 7
• 235000006200 Glycyrrhiza glabra Nutrition 0.000 claims description 7
• 235000017382 Glycyrrhiza lepidota Nutrition 0.000 claims description 7
• VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 claims description 7
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
• LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims description 7
• 239000001685 glycyrrhizic acid Substances 0.000 claims description 7
• 229960004949 glycyrrhizic acid Drugs 0.000 claims description 7
• UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims description 7
• 235000019410 glycyrrhizin Nutrition 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 229940010454 licorice Drugs 0.000 claims description 7
• 240000005528 Arctium lappa Species 0.000 claims description 6
• 235000007866 Chamaemelum nobile Nutrition 0.000 claims description 6
• 235000007232 Matricaria chamomilla Nutrition 0.000 claims description 6
• 241000208838 Asteraceae Species 0.000 claims description 5
• 240000001548 Camellia japonica Species 0.000 claims description 4
• 235000018597 common camellia Nutrition 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000002168 glycyrrhetinic acid group Chemical group 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 244000042664 Matricaria chamomilla Species 0.000 claims 3
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
• 241000202807 Glycyrrhiza Species 0.000 claims 2
• QRMSROOBWUTQPH-UHFFFAOYSA-N n-benzhydryloxyethanamine Chemical compound C=1C=CC=CC=1C(ONCC)C1=CC=CC=C1 QRMSROOBWUTQPH-UHFFFAOYSA-N 0.000 claims 2
• 235000003130 Arctium lappa Nutrition 0.000 claims 1
• 235000008078 Arctium minus Nutrition 0.000 claims 1
• 241000219429 Betula Species 0.000 claims 1
• 241000220485 Fabaceae Species 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
• 241000219784 Sophora Species 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 239000001257 hydrogen Substances 0.000 claims 1
• 229910052739 hydrogen Inorganic materials 0.000 claims 1
• 125000002883 imidazolyl group Chemical group 0.000 claims 1
• 210000003491 skin Anatomy 0.000 description 145
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
• 208000012641 Pigmentation disease Diseases 0.000 description 77
• 230000019612 pigmentation Effects 0.000 description 65
• XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 56
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• 238000009825 accumulation Methods 0.000 description 21
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• 230000006872 improvement Effects 0.000 description 18
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 18
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• 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 description 16
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