JP6284730B2 - 外用組成物 - Google Patents
外用組成物 Download PDFInfo
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- JP6284730B2 JP6284730B2 JP2013198248A JP2013198248A JP6284730B2 JP 6284730 B2 JP6284730 B2 JP 6284730B2 JP 2013198248 A JP2013198248 A JP 2013198248A JP 2013198248 A JP2013198248 A JP 2013198248A JP 6284730 B2 JP6284730 B2 JP 6284730B2
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- 239000000203 mixture Substances 0.000 title claims description 80
- 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 description 100
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 22
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 8
- 125000005427 anthranyl group Chemical group 0.000 claims description 7
- 239000006096 absorbing agent Substances 0.000 claims description 6
- 150000002461 imidazolidines Chemical class 0.000 claims description 5
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- QZMUBZJJJKIXKV-UHFFFAOYSA-N pyrroloquinoline quinol Chemical compound N1=C(C(O)=O)C=C(C(O)=O)C2=C(NC(C(=O)O)=C3)C3=C(O)C(O)=C21 QZMUBZJJJKIXKV-UHFFFAOYSA-N 0.000 claims 1
- -1 imidazolopyrroloquinoline compound Chemical class 0.000 description 30
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- FDATWRLUYRHCJE-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O FDATWRLUYRHCJE-UHFFFAOYSA-N 0.000 description 3
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- SOXAGEOHPCXXIO-DVOMOZLQSA-N menthyl anthranilate Chemical group CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 description 3
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- 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 compound 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 description 2
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- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 2
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 2
- MJBPWNFFVIYFNJ-UHFFFAOYSA-N 2-ethylhexyl 3-(4-benzylidene-3,5-dimethoxy-2-oxoimidazolidin-1-yl)propanoate Chemical group COC1C(N(C(N1CCC(=O)OCC(CCCC)CC)=O)OC)=CC1=CC=CC=C1 MJBPWNFFVIYFNJ-UHFFFAOYSA-N 0.000 description 2
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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。
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、及び(b)紫外線吸収剤を含む外用組成物。
項2. (b)紫外線吸収剤が、トリアジン誘導体、ジベンゾイルメタン誘導体、安息香酸誘導体、アントラニル誘導体、イミダゾリジン誘導体からなる群より選ばれる少なくとも1種の紫外線吸収剤を含む項1に記載の外用組成物。
項3. トリアジン誘導体が、2,4−ビス−〔{4−(2−エチルヘキシルオキシ)−2−ヒドロキシ}−フェニル〕−6−(4−メトキシフェニル)−1,3,5−トリアジン、2,2’-メチレンビス(6-(2H-ベンゾトリアゾール-2-イル)-4-(1,1,3,3-テトラメチルブチル)フェノールである項1〜2に記載の外用組成物。
項4. ジベンゾイルメタン誘導体が、4−tert−ブチル−4’−メトキシジベンゾイルメタンである項1又は2に記載の外用組成物。
項5. 安息香酸誘導体が、2−〔4−(ジエチルアミノ)−2−ヒドロキシベンゾイル〕安息香酸ヘキシルである項1〜2に記載の外用組成物。
項6. アントラニル誘導体が、アントラニル酸メンチルである項1又は2に記載の外用組成物。
項7. イミダゾリジン誘導体が、ジメトキシベンジリデンオキソイミダゾリジンプロピオン酸2−エチルヘキシルである項1又は2に記載の外用組成物。
項8. (b)紫外線吸収剤を、組成物の全量に対して、0.01〜30重量%含む項1〜7の何れかに記載の外用組成物。
項9. 紫外線からの皮膚又は毛髪の保護用である項1〜8の何れかに記載の外用組成物。
本発明の外用組成物は、(a)PQQ又はその塩、(b)紫外線吸収剤を含む外用組成物である。
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。
また、組成物中のPQQ又はその塩の含有量は、組成物の全量に対して、1重量%以下が好ましく、0.3重量%以下がより好ましく、0.1重量%以下がさらにより好ましく、0.05重量%以下がさらにより好ましく、0.03重量%以下がさらにより好ましい。上記範囲であれば、製剤中での溶解性が良好で、また外用組成物としての外観の点で優れたものとなる。
紫外線吸収剤としては、トリアジン誘導体、ジベンゾイルメタン誘導体、安息香酸誘導体、アントラニル誘導体、イミダゾリン誘導体等の有機紫外線吸収剤が挙げられる。
中でも、安息香酸誘導体、ジベンゾイルメタン誘導体、トリアジン誘導体が好ましく、2−〔4−(ジエチルアミノ)−2−ヒドロキシベンゾイル〕安息香酸ヘキシル、4−tert−ブチル−4’−メトキシジベンゾイルメタン、2,4−ビス−〔{4−(2−エチルヘキシルオキシ)−2−ヒドロキシ}−フェニル〕−6−(4−メトキシフェニル)−1,3,5−トリアジンがより好ましい。
また、外用組成物中の紫外線吸収剤の含有量は、組成物の全量に対して、30重量%以下が好ましく、10重量%以下がより好ましく、7重量%以下がさらにより好ましい。上記範囲であれば、べたつき、きしみが発生せず、使用感が良好な組成物となる。
また、PQQ又はその塩の含有量に対する紫外線吸収剤の含有量の比率は、PQQ又はその塩1重量部に対して、30000重量部以下が好ましく、10000重量部以下がより好ましく、7000重量部以下がさらにより好ましい。上記範囲であれば、PQQ又はその塩の熱安定性が良好になる。
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及びその誘導体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)紫外線吸収剤を含む紫外線吸収剤を、医薬品、医薬部外品、又は化粧品等の外用組成物に使用できる、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使用でき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。
医薬品、医薬部外品、又は化粧品等の外用組成物に使用される、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、スクワラン、ワセリン、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;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;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、トリエチルヘキサノイン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、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。
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、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。
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、PQQ又はその塩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。
PQQ又はその塩以外の薬理活性成分又は生理活性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、ペプチド又はその誘導体、アミノ酸又はその誘導体、角質軟化成分、及び収斂成分等が挙げられる。
質のような脂質などが挙げられる。
紫外線防御成分としては、例えば、ケイ酸亜鉛、ケイ酸セリウム、ケイ酸チタン、酸化亜鉛、酸化ジルコニウム、酸化セリウム、酸化チタン、酸化鉄等の無機化合物、それらの無機化合物を含水ケイ酸、無水ケイ酸、水酸化アルミニウム、マイカやタルク等の無機粉体で被覆したり、ポリアミド、ポリエチレン、ポリエステル、ポリスチレン、ナイロン等の樹脂粉体に複合化したもの、さらにシリコーン油や脂肪酸アルミニウム塩等で処理したものなどが挙げられる。
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、例えば以下の方法で使用すればよい。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)を皮膚に塗布、貼付、又は噴霧などにより適用すればよい。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塗布すればよい。また、塗布期間は、特に制限はないが、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、特に光老化による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。
本発明の外用組成物は、紫外線からの皮膚や毛髪の保護、日焼け予防などのための日焼け止め化粧料、紫外線防御用化粧料としても好適に使用することができる。
本発明は、(a)PQQ又はその塩を含む組成物(特に、外用組成物)に、(b)紫外線吸収剤を添加することによって、PQQ又はその塩の熱安定性を向上させる方法を包含する。
この方法において、各成分の種類、各成分の含有量、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。
表1の組成に従い、(アクリレーツ/アクリル酸(C10−30))クロスポリマーを秤りとり、攪拌しながら水に分散させ、トリエタノールアミンで膨潤し水層とした。一方で、表1の(B)欄に示す紫外線吸収剤をトリエチルヘキサノイン及びポリオキシエチレン硬化ヒマシ油60に80℃で加熱して溶解し、油層とした。ディスパーで水層を攪拌しながら、油層を投入し、T.K.ROBOMICS(PRIMIX社製)を用いて3000rpmで5分間攪拌した。最後にPQQ-2Naを添加し、トリエタノールアミンを用いてpHを調整した後、攪拌した(実施例1〜3)。比較例1は紫外線吸収剤を入れる以外は、実施例1〜3と同様に作製した。実施例1〜3および比較例1の各外用組成物を10mL容量のヘッドスペースバイアルに5gずつ分注し、密閉後、70℃にて2週間保存した。保存前と保存後のサンプル中のPQQ-2Na含有量を、高速液体クロマトグラフィーを用いて定量した。さらに以下に示す式1を用いて残存率を算出し、結果を図1に示した。
PQQ-2Na残存率(%)=(加速試験後のPQQ-2Na含有量/加速試験前のPQQ-2Na含有量)×100 (式1)
PQQ-2Naを含む組成物である比較例1においては、PQQ-2Naは75%しか残存していなかった。一方で、PQQ-2Naを含む組成物に、紫外線吸収剤である4−tert−ブチル−4’−メトキシジベンゾイルメタン(パルソール1789)を配合するとPQQ-2Naの残存率は98%まで向上し、殆ど分解しない熱に安定な組成物を作ることに成功した(実施例1)。また、2,4−ビス−{[4−(2−エチル−ヘキシルオキシ)−2−ヒドロキシ]−フェニル}−6−(4−メトキシフェニル)−1,3,5−トリアジン(チノソーブS)、2−[−4−(ジエチルアミノ)−2−ヒドロキシベンゾイル]安息香酸ヘキシルエステル(ユビナールAPlus)を配合することにより、PQQ-2Naの残存率が、それぞれ91%(実施例2)、89%(実施例3)まで上昇した。
Claims (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、及び(b)紫外線吸収剤を含む外用組成物であり、(b)紫外線吸収剤が、トリアジン誘導体、ジベンゾイルメタン誘導体、安息香酸誘導体、アントラニル誘導体、イミダゾリジン誘導体からなる群より選ばれた少なくとも1種の紫外線吸収剤を含む外用組成物(ただし、前記ピロロキノリンキノンは還元型ピロロキノリンキノンでない)。
- (b)紫外線吸収剤を、組成物の全量に対して、0.01〜30重量%含む請求項1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含有量に対する(b)紫外線吸収剤の含有量の比率が、(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1重量部に対して、0.2重量部以上、30000重量部以下である請求項1又は2に記載の外用組成物。
- 紫外線からの皮膚又は毛髪の保護用である請求項1〜3の何れかに記載の外用組成物。
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JPH02142713A (ja) * | 1988-11-25 | 1990-05-31 | Shiseido Co Ltd | 皮膚外用剤 |
JPH03112912A (ja) * | 1989-09-27 | 1991-05-14 | Sanko Seibutsu Kagaku Kenkyusho:Kk | 化粧料組成物 |
JP3625493B2 (ja) * | 1994-07-07 | 2005-03-02 | 三菱瓦斯化学株式会社 | 紫外線吸収剤及び皮膚外用剤 |
JPH0899856A (ja) * | 1994-09-29 | 1996-04-16 | Shiseido Co Ltd | 皮膚外用剤 |
JPH09249545A (ja) * | 1996-03-12 | 1997-09-22 | Shiseido Co Ltd | 皮膚外用剤 |
JP2009221154A (ja) * | 2008-03-17 | 2009-10-01 | Pola Chem Ind Inc | インタ−ロイキン−6産生抑制剤 |
JP4657323B2 (ja) * | 2008-07-02 | 2011-03-23 | 株式会社資生堂 | 含水組成物 |
JP2011026226A (ja) * | 2009-07-23 | 2011-02-10 | Mitsubishi Gas Chemical Co Inc | ピロロキノリンキノン類を含む液体の保存方法 |
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JP2012097020A (ja) * | 2010-11-01 | 2012-05-24 | Mitsubishi Gas Chemical Co Inc | 一重項酸素の消去方法 |
CN102688155A (zh) * | 2011-03-23 | 2012-09-26 | 日本乐敦制药株式会社 | 外用组合物 |
WO2012137932A1 (ja) * | 2011-04-07 | 2012-10-11 | ロート製薬株式会社 | 外用組成物 |
JP2013151480A (ja) * | 2011-12-26 | 2013-08-08 | Rohto Pharmaceutical Co Ltd | 外用組成物の安定化方法 |
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