JP2014131993A - 外用組成物 - Google Patents
外用組成物 Download PDFInfo
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- JP2014131993A JP2014131993A JP2013249996A JP2013249996A JP2014131993A JP 2014131993 A JP2014131993 A JP 2014131993A JP 2013249996 A JP2013249996 A JP 2013249996A JP 2013249996 A JP2013249996 A JP 2013249996A JP 2014131993 A JP2014131993 A JP 2014131993A
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- 239000000203 mixture Substances 0.000 title claims abstract description 104
- MMXZSJMASHPLLR-UHFFFAOYSA-N pyrroloquinoline quinone Chemical compound C12=C(C(O)=O)C=C(C(O)=O)N=C2C(=O)C(=O)C2=C1NC(C(=O)O)=C2 MMXZSJMASHPLLR-UHFFFAOYSA-N 0.000 claims abstract description 199
- 150000003839 salts Chemical class 0.000 claims abstract description 73
- 108010035532 Collagen Proteins 0.000 claims abstract description 43
- 102000008186 Collagen Human genes 0.000 claims abstract description 43
- 229920001436 collagen Polymers 0.000 claims abstract description 43
- 229920002683 Glycosaminoglycan Polymers 0.000 claims abstract description 41
- 229940088594 vitamin Drugs 0.000 claims abstract description 37
- 229930003231 vitamin Natural products 0.000 claims abstract description 37
- 235000013343 vitamin Nutrition 0.000 claims abstract description 37
- 239000011782 vitamin Substances 0.000 claims abstract description 37
- 150000001413 amino acids Chemical class 0.000 claims abstract description 33
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 59
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical group CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 36
- 239000011668 ascorbic acid Substances 0.000 claims description 34
- 229920002674 hyaluronan Polymers 0.000 claims description 33
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- 235000010323 ascorbic acid Nutrition 0.000 claims description 29
- 229960005070 ascorbic acid Drugs 0.000 claims description 29
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 6
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 6
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 5
- 229940059329 chondroitin sulfate Drugs 0.000 claims description 5
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 3
- 230000000699 topical effect Effects 0.000 claims description 2
- -1 imidazolopyrroloquinoline compound Chemical class 0.000 description 68
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 12
- 229920002385 Sodium hyaluronate Polymers 0.000 description 12
- 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 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
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- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 12
- 239000012085 test solution Substances 0.000 description 12
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 229940014041 hyaluronate Drugs 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- 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 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 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 description 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 230000001766 physiological effect Effects 0.000 description 7
- 238000013112 stability test Methods 0.000 description 7
- 229960003495 thiamine Drugs 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229940072107 ascorbate Drugs 0.000 description 6
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 102000004196 processed proteins & peptides Human genes 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
- 241000218657 Picea Species 0.000 description 5
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 5
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
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- 239000003795 chemical substances by application Substances 0.000 description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
- KXKPYJOVDUMHGS-OSRGNVMNSA-N chondroitin sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O1 KXKPYJOVDUMHGS-OSRGNVMNSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 5
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004811 liquid chromatography Methods 0.000 description 5
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 4
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 4
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- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 4
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- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
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- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 4
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- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 4
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Landscapes
- Cosmetics (AREA)
Abstract
【解決手段】(a)ピロロキノリンキノン、又は薬学的若しくは生理的に許容されるその塩、(b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種、並びに(c)ムコ多糖類を含む外用組成物。
【選択図】なし
Description
PQQには、多くの生理活性があることが知られており、医薬品、医薬部外品、化粧品、又はサプリメントの有効成分としての使用が期待されている。このような生理活性として、活性酸素及びラジカルの消去作用、細胞増殖促進作用、紫外線吸収作用、神経成長因子産生促進作用、脳機能改善作用、育毛作用、顔色改善作用、メラニン産生抑制又は美白作用、ミトコンドリア賦活作用、及び抗疲労作用などが知られている。
また、PQQは、光安定性が悪く、特に、紫外線照射によって分解が促進される。 PQQの分解により、製剤中のPQQ含量が低下すると、PQQの所期の効果が得られない。また、PQQの分解により、製剤が桃色から黄色に変色したり、製剤の性状が変化して使用感に悪影響を及ぼす場合がある。例えば、クリームや乳液では、製剤の変色、液だれ、成分の分離などが発生し、視覚的に、また使用感の点で、商品の価値を損ねる。
従って、本発明は、PQQ又はその塩と、ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる成分とを含む外用組成物であって、PQQ又はその塩の安定性に優れる組成物を提供することを課題とする。
項1. (a)ピロロキノリンキノン、又は薬学的若しくは生理的に許容されるその塩、(b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種、並びに(c)ムコ多糖類を含む外用組成物。
項2. (c)ムコ多糖類が、ヒアルロン酸、低分子ヒアルロン酸、アセチル化ヒアルロン酸、若しくはコンドロイチン硫酸、又はそれらの塩である項1に記載の外用組成物。
項3. (b)のビタミン類が、アスコルビン酸、ニコチンアミド、それらの誘導体、又はそれらの塩である項1又は2に記載の外用組成物。
項4. (a)ピロロキノリンキノン、又は薬学的若しくは生理的に許容されるその塩の1重量部に対して、(c)ムコ多糖類を0.1〜1000重量部含む項1〜3の何れかに記載の外用組成物。
項5. (b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種の1重量部に対して、(c)ムコ多糖類を0.0001〜1000重量部含む項1〜4の何れかに記載の外用組成物。
項6. (c)ムコ多糖類を、組成物の全量に対して、0.001〜10重量%含む項1〜5の何れかに記載の外用組成物。
項7. (b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種を、組成物の全量に対して、0.0001〜20重量%含む項1〜6の何れかに記載の外用組成物。
項8. (a)ピロロキノリンキノン、又は薬学的若しくは生理的に許容されるその塩を、組成物の全量に対して、0.00001〜1重量%含む項1〜7の何れかに記載の外用組成物。
本発明の外用組成物は、ビタミン類、アミノ酸、及び低分子コラーゲンからなる群より選ばれる化合物に加えて、さらに、ムコ多糖類を含むため、PQQ又はその塩が安定に保たれる。また、PQQ又はその塩は光照射により一層変色や分解が促進されるが、本発明の外用組成物は、光照射した場合にも、PQQ又はその塩が安定に保たれる。
ムコ多糖類は、保湿作用や皮膚弾力の向上作用などが期待されるため、外用組成物の成分として汎用されている成分である。本発明によれば、汎用の成分を加えるだけで、簡単にPQQ又はその塩の安定性を向上させることができる。
本発明の外用組成物は、(a)PQQ又はその塩、(b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種、並びに(c)ムコ多糖類を含む組成物である。
PQQは動物、植物、及び細菌など多様な生物体内に存在するので、種々の生物から抽出できる。また、PQQは、市販品を購入できる。
PQQの生理学的又は薬学的に許容されるその塩としては、ナトリウム塩、カリウム塩、及びリチウム塩のようなアルカリ金属塩;カルシウム塩、及びマグネシウム塩のようなアルカリ土類金属塩などが挙げられる。塩の中では、ナトリウム塩、カリウム塩、リチウム塩、カルシウム塩、及びマグネシウム塩が好ましい。
ビタミン類の種類は、薬学的又は生理学的に許容され得る限り、特に制限されない。具体的には、ビタミンA類;ビタミンB類;ビタミンC類;エルゴカルシフェロール(ビタミンD2)、コレカルシフェロール(ビタミンD3)などのビタミンD類、7−デヒドロコレステロール、エルゴステロールなどのプロビタミンD類;ビタミンE類;フィロキノン(ビタミンK1)、メナキノン(ビタミンK2)、メナジオン(ビタミンK3)などのビタミンK類;ユビキノン、グルクロラクトン、グルクロン酸アミド、オロチン酸、L-カルニチン、フェルラ酸、α−リポ酸、オロット酸等のビタミン類似物質(ビタミン様作用因子)などが挙げられる。
また、ビタミン類の中では、ビタミンB類も好ましく、中でも、ニコチンアミドがより好ましい。
ビタミン類は、1種を単独で、又は2種以上を組み合わせて使用できる。
アミノ酸類は1種を単独で使用してもよく、また2種以上を任意に組合わせて使用してもよい。
低分子コラーゲンの調製方法を例示すれば、魚や動物の組織を粉砕し、熱水などによりコラーゲンを抽出した後、酸又はアルカリや、ペプシン、トリプシンのようなタンパク質加水分解酵素で処理し、さらに必要に応じて、塩析や透析等の公知の精製手段を施すことにより調製できる。また、市販のコラーゲン(例えば、新田ゼラチン社製「マリンジェンSP−03(PF)」)を、コラーゲンペプチドの出発原料とすることもできる。
低分子コラーゲンは市販品を用いることもできる。市販品として、成和化成製の「プロモイスW−32」、「プロモイスW−32LS」、「プロモイスW−32NO」、「プロモイスW−32R」(以上、重量平均分子量400)、成和化成製の「プロモイスW−52」、「プロモイスW−52P」、「プロモイスW−52Q」(以上、重量平均分子量2000)、一丸ファルコス社製の「ファルコニックスCTP−F(BG)」(重量平均分子量5000)、株式会社ニッピの「ニッピコラーゲン−AFD」、「ニッピコラーゲン−FCP」、「ニッピコラーゲン−FCP-G」(重量平均分子量3000〜5000)等が挙げられる。低分子コラーゲンの重量平均分子量は、約200〜20000が好ましく、約1000〜10000がより好ましく、約2000〜5000がさらに好ましい。
ムコ多糖類は、鶏冠、臍の緒、眼球、皮膚、軟骨などの動物組織、ストレプトコッカス属微生物などのムコ多糖類生産微生物、動物細胞又は植物細胞の培養物から常法により抽出したもの等が知られている。本発明では、ムコ多糖類の由来は限定されず、医薬品、医薬部外品、又は化粧品の分野で使用され得るものであれば使用できる。また、天然物からの抽出物から調製した塩や誘導体も用いることができる。ムコ多糖類は、市販品を購入することもできる。
アルケニル基としては、炭素数2〜12のアルケニル基が挙げられ、好ましくは炭素数2〜6のアルケニル基である。具体例としては、ビニル基、アリル基等が挙げられる。
アルキル基及びアルケニル基は置換されていても良く、その置換基としては、炭素数1〜6のアルコキシ基(メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、s−ブトキシ基、t−ブトキシ基、イソブトキシ基、ペンチルオキシ基、ヘキシルオキシ基等)、ハロゲン原子(フッ素原子、塩素原子、臭素原子、ヨウ素原子等)、アミノ基、ヒドロキシ基等が挙げられる。
アリールカルボニル基としては炭素数7〜15のアリールカルボニル基が挙げられ、好ましくは炭素数7〜12のアリールカルボニル基である。具体例としては、ベンゾイル基、ナフチルカルボニル基(1−ナフチルカルボニル基、2−ナフチルカルボニル基)等が挙げられる。また、アリールカルボニル基は置換されていても良く、その置換基としては、炭素数1〜6のアルキル基(メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、s−ブチル基、t−ブチル基、イソブチル基、ペンチル基、ヘキシル基等)、炭素数1〜6のアルコキシ基(メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、s−ブトキシ基、t−ブトキシ基、イソブトキシ基、ペンチルオキシ基、ヘキシルオキシ基等)、ハロゲン原子(フッ素原子、塩素原子、臭素原子、ヨウ素原子等)、アミノ基、ヒドロキシ基等が挙げられる。
例えば、ヒアルロン酸誘導体としては、天然のヒアルロン酸(高分子ヒアルロン酸)を、例えば、塩酸のような酸の存在下で加水分解したり、ヒアルロニダーゼなどの酵素を用いて処理したり、又は超音波や剪断によって物理的に切断することにより、調製した分解ないしは低分子ヒアルロン酸も挙げられる。分解ないしは低分子ヒアルロン酸は、ヒアロオリゴ(キユーピー(株))などの市販品を購入することもできる。
中でも、保水性が良好である点で、ヒアルロン酸、アセチル化ヒアルロン酸、低分子ヒアルロン酸、コンドロイチン硫酸、及びこれらの塩(ヒアルロン酸の塩としては、ヒアルロン酸ナトリウム等)がより好ましい。
但し、例えば、分解ないしは低分子ヒアルロン酸のような分解ないしは低分子ムコ多糖類の場合、重量平均分子量は、例えば100万以下、好ましくは10万以下、より好ましくは2万以下、さらにより好ましくは1万以下であればよい。分解ないしは低分子ヒアルロン酸のような分解ないしは低分子ムコ多糖類の重量平均分子量の下限値は、通常、10000程度とすればよい。
本発明の組成物のpHは、2.5以上が好ましく、3以上がより好ましく、4以上がさらにより好ましい。また、9以下が好ましく、8.5以下がより好ましく、8以下がさらにより好ましい。上記範囲であれば、PQQ又はその塩が安定に保たれる。
本発明の外用組成物は、(a)PQQ又はその塩、(b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種、並びに(c)ムコ多糖類を、医薬品、医薬部外品、又は化粧品等の外用組成物に通常使用される、薬学的又は生理学的に許容される基剤又は担体、及び必要に応じて医薬品、医薬部外品、又は化粧品等の外用組成物に通常使用される添加剤と共に混合して、医薬品、医薬部外品、又は化粧品用の外用組成物とすることができる。
医薬部外品又は化粧品用の外用組成物とする場合も、上記の医薬品と同様の形態にすることができる。また、それ以外にも、スティック剤、及び不織布に薬液を含浸させたシート剤等が挙げられる。
剤も挙げられる。
医薬品、医薬部外品、又は化粧品等の外用組成物に通常使用される、薬学的又は生理学的に許容される基剤又は担体としては、流動パラフィン、スクワラン、ワセリン、ゲル化炭化水素(プラスチベースなど)、オゾケライト、α−オレフィンオリゴマー、及び軽質流動パラフィンのような炭化水素;メチルポリシロキサン、架橋型メチルポリシロキサン、高重合メチルポリシロキサン、環状シリコーン、アルキル変性シリコーン、架橋型アルキル変性シリコーン、アミノ変性シリコーン、ポリエーテル変性シリコーン、ポリグリセリン変性シリコーン、架橋型ポリエーテル変性シリコーン、架橋型アルキルポリエーテル変性シリコーン、シリコーン・アルキル鎖共変性ポリエーテル変性シリコーン、シリコーン・アルキル鎖共変性ポリグリセリン変性シリコーン、ポリエーテル変性分岐シリコーン、ポリグリセリン変性分岐シリコーン、アクリルシリコン、フェニル変性シリコーン、及びシリコーンレジンのようなシリコーン油;セタノール、セトステアリルアルコール、ステアリルアルコール、及びベヘニルアルコールのような高級アルコール;コレステロール、フィトステロール、及びヒドロキシステアリン酸フィトステリルのようなステロール類;ホホバ油、メドフォーム油、ヒマワリ油、ブドウ種子油、椿油、スクワラン、シアバター、及びコメ胚芽油のような植物油;ラノリン、オレンジラフィー油、スクワラン、及び馬油のような動物油;エチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、カチオン化グアガム、及びアセチル化ヒアルロン酸のような天然高分子誘導体;ポリビニルピロリドン、カルボキシビニルポリマー、及びアクリル酸メタクリル酸アルキル共重合体のような合成高分子;カラギーナン、アルギン酸、セルロース、グアーガム、クインスシード、デキストラン、ジェランガム、及びヒアルロン酸のような天然高分子;ミリスチン酸イソプロピル、ミリスチン酸オクチルドデシル、パルミチン酸イソプロピル、パルミチン酸セチル、イソノナン酸イソノニル、テトラ2−エチルヘキサン酸ペンタエリスリット、ホホバ油、及びトリ(カプリル酸/カプリン酸)グリセリルのようなエステル類;デキストリン、及びマルトデキストリンのような多糖類;エタノール、及びイソプロパノールのような低級アルコール;エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピル
エーテル、ジプロピレングリコールモノエチルエーテル、及びジプロピレングリコールモノプロピルエーテルのようなグリコールエーテル;ポリエチレングリコール、プロピレングリコール、1,3-ブチレングリコール、グリセリン、イソプレングリコール、ジグリセリン、及びジプロピレングリコールなどの多価アルコール;コハク酸、グリコール酸、グルコン酸、及びクエン酸などの有機酸;並びに水などの水系基剤などが挙げられる。
中でも、多価アルコール、高級アルコール、炭化水素、エステル類、シリコーン油、及び有機酸が好ましく、多価アルコールがより好ましい。多価アルコールの中では、1,3-ブチレングリコール、プロピレングリコール、イソプレングリコール、グリセリン、ジグリセリン、及びジプロピレングリコールが好ましく、1,3-ブチレングリコール、プロピレングリコール、グリセリン、及びジグリセリンがさらに好ましい。本発明の組成物の好ましい例として、基剤として低級アルコール及び/又は多価アルコールを含む液剤、ローション剤、クリーム剤、ゲル剤、乳剤、及び軟膏が挙げられる。
基剤又は担体は、1種を単独で、又は2種以上を組み合わせて使用できる。
本発明の組成物には、本発明の効果を損なわない範囲で、医薬品、医薬部外品、又は化粧品等の外用組成物に添加される添加剤、例えば、酸化防止剤、界面活性剤、増粘剤、保存剤、pH調整剤、安定化剤、刺激軽減剤、防腐剤、着色剤、香料、及び/又はパール光沢付与剤等を添加することができる。
刺激低減剤としては、甘草エキス、及びアルギン酸ナトリウムなどが挙げられる。
本発明の外用組成物は、本発明の効果を損なわない範囲で、その他の有効成分((a)PQQ又はその塩、(b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種、並びに(c)ムコ多糖類以外の薬理活性成分又は生理活性成分)を含むことができる。
その他の有効成分の具体例としては、例えば、保湿成分、抗炎症成分、抗菌又は殺菌成分、ビタミン類、ペプチド又はその誘導体、アミノ酸又はその誘導体、細胞賦活化成分、老化防止成分、血行促進成分、角質軟化成分、及び収斂成分などが挙げられる。
質のような脂質;並びにカミツレエキス、ハマメリスエキス、チャエキス、及びシソエキスのような植物抽出エキスなどが挙げられる。
ボフラビンテトラ酪酸エステル、リボフラビン5’−リン酸エステルナトリウム、及びリボフラビンテトラニコチン酸エステル等のビタミンB2類;ニコチン酸dl−α−トコフェロール、ニコチン酸ベンジル、ニコチン酸メチル、ニコチン酸β−ブトキシエチル、及びニコチン酸1−(4−メチルフェニル)エチル等のニコチン酸類;アスコルビゲン−A、アスコルビン酸ステアリン酸エステル、アスコルビン酸パルミチン酸エステル、及びジパルミチン酸L−アスコルビルなどのビタミンC類;メチルヘスペリジン、エルゴカルシフェロール、及びコレカルシフェロールなどのビタミンD類;フィロキノン、及びファルノキノン等のビタミンK類;ジベンゾイルチアミン、ジベンゾイルチアミン塩酸塩、チアミン塩酸塩、チアミンセチル塩酸塩、チアミンチオシアン酸塩、チアミンラウリル塩酸塩、チアミン硝酸塩、チアミンモノリン酸塩、チアミンリジン塩、チアミントリリン酸塩、チアミンモノリン酸エステルリン酸塩、チアミンモノリン酸エステル、チアミンジリン酸エステル、チアミンジリン酸エステル塩酸塩、チアミントリリン酸エステル、及びチアミントリリン酸エステルモノリン酸塩等のビタミンB1類;塩酸ピリドキシン、酢酸ピリドキシン、塩酸ピリドキサール、5’−リン酸ピリドキサール、及び塩酸ピリドキサミン等のビタミンB6類;シアノコバラミン、ヒドロキソコバラミン、及びデオキシアデノシルコバラミン等のビタミンB12類;葉酸、及びプテロイルグルタミン酸等の葉酸類;ニコチン酸、及びニコチンアミドなどのニコチン酸類;パントテン酸、パントテン酸カルシウム、パントテニルアルコール(パンテノール)、D−パンテサイン、D−パンテチン、補酵素A、及びパントテニルエチルエーテル等のパントテン酸類;ビオチン、及びビオチシン等のビオチン類;アスコルビン酸、アスコルビン酸ナトリウム、デヒドロアスコルビン酸、アスコルビン酸リン酸エステルナトリウム、及びアスコルビン酸リン酸エステルマグネシウム等のアスコルビン酸誘導体のようなビタミンC類;並びにカルニチン、フェルラ酸、α−リポ酸、オロット酸、γ−オリザノール等のビタミン様作用因子などが挙げられる。
老化防止成分としては、例えば、パンガミン酸、カイネチン、ウルソール酸、ウコンエキス、スフィンゴシン誘導体、ケイ素、ケイ酸、N−メチル−L−セリン、及びメバロノラクトン等が挙げられる。
収斂成分としては、例えば、パラフェノールスルホン酸亜鉛、酸化亜鉛、メントール、及びエタノールなどが挙げられる。
本発明の外用組成物(皮膚外用剤)は、使用対象の皮膚の状態、年齢、性別などによって異なるが、例えば以下の方法とすればよい。即ち、1日数回(例えば、約1〜5回、好ましくは1〜3回)、1回当たり適量(例えば、約0.05〜5g)を皮膚に適用(塗布、噴霧、貼付など)すればよい。また、PQQ又はその塩の1日使用量が、例えば、約0.0005〜0.05g、好ましくは約0.001〜0.02g、より好ましくは約0.002〜0.01gとなるように組成物を適用すればよい。
また、適用期間は、例えば、約2週間〜6ヶ月、好ましくは約1〜6ヶ月間とすればよい。
本発明の外用組成物は、PQQ又はその塩の生理活性を期待して、種々の皮膚疾患や皮膚トラブルを有する人に好適に使用できる。特に、シワ、タルミを有する人、肌のキメが乱れている人、敏感肌の人が好適な対象となる。また、皮膚トラブルの予防のため、正常な肌を有する人も好適な使用対象となる。
本発明は、(a)PQQ若しくはその塩、並びに(b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種を含む組成物に、(c)ムコ多糖類を添加する、PQQ若しくはその塩の安定性の向上方法、PQQ若しくはその塩の含有量低下防止方法、又は組成物の変色防止方法を包含する。
各成分の種類、各成分の使用量、組成物のpH、組成物の性状などは、上記説明した本発明の外用組成物の場合と同じである。
(1)調製直後の色味変化の評価
後掲の表1に示す組成に従い、各試験液を調製後、ガラス製スクリューバイアル(容量10mL)に7mLずつ充填した。すなわち、実施例1〜2の組成物については、PQQ・2Naにヒアルロン酸ナトリウムを加えた後に、(b)成分である3-O-アスコルビン酸エチル、又は低分子コラーゲン(ニッピコラーゲン−FCP、ニッピ社、重量平均分子量:3000〜5000)を容器に加え、比較例1〜2の組成物については、PQQ・2Naに、(b)成分である3-O-アスコルビン酸エチル、又は低分子コラーゲン(ニッピコラーゲン−FCP、ニッピ社、重量平均分子量:3000〜5000)を容器中で加えた。参考例1の組成物については、PQQ・2Naにヒアルロン酸ナトリウムを加えた。
調製した試験液について、目視にて色味判定(色調評価)を行った結果を表1に示す。
上記(1)「調製直後の色味変化の評価」で作製した実施例、比較例、又は参考例の組成物に対して、D65ランプで5000lxを約60時間(合計30万lx・hr)の条件下で光照射を行った後に、目視でこれらの組成物の色味を判定(色調評価)した。結果を表1に示す。
後掲の表2に示す組成に従い、各試験液を調製後、ガラス製スクリューバイアル(容量10mL)に7mLずつ充填した。すなわち、実施例3〜6の組成物については、PQQ・2Naにヒアルロン酸ナトリウムを加えた後に、(b)成分である3−O−アスコルビン酸エチルを容器に加え、比較例3〜5の組成物については、PQQ・2Naに、(b)成分である3−O−アスコルビン酸エチルを容器中で加えた。
これらの試験液に対して、D65ランプで5000lxで約120時間(合計60万lx・hr)の光照射を行った。光照射の後に目視でこれらの組成物の色味を判定した結果を表2に示す。
以上より、ムコ多糖の添加により、PQQ又はその塩と、ビタミン類、アミノ酸類又は低分子コラーゲンを含む組成物の変色が防止されたことが分かる。
表3に示す試験液を定法に従い調製し、室温にて24時間遮光保管した後に、下記条件の液体クロマトグラフィーでPQQ・2Na残存量を測定し、式1を用いて残存率を算出した。
検出器:紫外吸光光度計(測定波長;350nm)
カラム:Inertsil ODS-3(4.6×150mm,5μm) GLサイエンス
カラム温度:40℃
移動相:テトラブチルアンモニウムを15mMとなるように水1000mLに溶かし、リン酸でpH3.5に調製した液とメタノール混液(容量比1:1)
流量:PQQの保持時間が約6〜8分になるように調整する。(c.f. 1.0mL/min)
<式1>
残存率(%)=
(PQQ・2Na含有量/対応する参考例のPQQ・2Na含有量)×100
表6に示す試験液を定法に従い調製し、室温にて24時間遮光保管した後に、「(4)調製直後のPQQ・2Na含有量変化の評価(No.1)」と同様にしてPQQ・2Naの残存率を算出した。
表7〜8に示す試験液を定法に従い調製し、容量10mLのガラスバイアルに各試験液を10mLずつ充填した。次いで、D65ランプで、5000lxで約120時間(合計60万lx・hr)の光照射を行った。照射前後で、PQQ・2Naの含有量を前述の条件の液体クロマトグラフィーで定量し、式2を用いてPQQ・2Na残存率を算出した。
<式2>
残存率(%)=
(光照射後のPQQ・2Na含有量/光照射前のPQQ・2Na含有量)×100
表8に示す試験液を定法に従い調製し、容量10mLのガラスバイアルに各試験液を10mLずつ充填した。次いで、D65ランプで、5000lxで約120時間(合計60万lx・hr)の光照射を行った。照射前後で、PQQ・2Naの含有量を前述の条件の液体クロマトグラフィーで定量し、「(6)光安定性試験(光照射後のPQQ含量)(No.1)」と同様の方法でPQQ・2Naの残存率を算出した。
表9に示す試験液を定法に従い調製し、容量10mLのガラスバイアルに各試験液を10mLずつ充填した。次いで、D65ランプで、5000lxで約60時間(合計30万lx・hr)の光照射を行った。照射前後で、PQQ・2Naの含有量を前述と同様にして液体クロマトグラフィーで定量し、「(6)光安定性試験(光照射後のPQQ含量)(No.1)」と同様の方法でPQQ・2Naの残存率を算出した。
Claims (8)
- (a)ピロロキノリンキノン、又は薬学的若しくは生理的に許容されるその塩、(b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種、並びに(c)ムコ多糖類を含む外用組成物。
- (c)ムコ多糖類が、ヒアルロン酸、低分子ヒアルロン酸、アセチル化ヒアルロン酸、若しくはコンドロイチン硫酸、又はそれらの塩である請求項1に記載の外用組成物。
- (b)のビタミン類が、アスコルビン酸、ニコチンアミド、それらの誘導体、又はそれらの塩である請求項1又は2に記載の外用組成物。
- (a)ピロロキノリンキノン、又は薬学的若しくは生理的に許容されるその塩の1重量部に対して、(c)ムコ多糖類を0.1〜1000重量部含む請求項1〜3の何れかに記載の外用組成物。
- (b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種の1重量部に対して、(c)ムコ多糖類を0.0001〜1000重量部含む請求項1〜4の何れかに記載の外用組成物。
- (c)ムコ多糖類を、組成物の全量に対して、0.001〜10重量%含む請求項1〜5の何れかに記載の外用組成物。
- (b)ビタミン類、アミノ酸類、及び低分子コラーゲンからなる群より選ばれる少なくとも1種を、組成物の全量に対して、0.0001〜20重量%含む請求項1〜6の何れかに記載の外用組成物。
- (a)ピロロキノリンキノン、又は薬学的若しくは生理的に許容されるその塩を、組成物の全量に対して、0.00001〜1重量%含む請求項1〜7の何れかに記載の外用組成物。
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JP2021524495A (ja) * | 2018-07-10 | 2021-09-13 | ヌチド リミテッド | 酸化的ストレスおよびミトコンドリアストレスから,細胞を保護する組成物 |
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