JP2013542944A - ピリチオン及び鉄キレート化剤を含むパーソナルケア組成物 - Google Patents
ピリチオン及び鉄キレート化剤を含むパーソナルケア組成物 Download PDFInfo
- Publication number
- JP2013542944A JP2013542944A JP2013536873A JP2013536873A JP2013542944A JP 2013542944 A JP2013542944 A JP 2013542944A JP 2013536873 A JP2013536873 A JP 2013536873A JP 2013536873 A JP2013536873 A JP 2013536873A JP 2013542944 A JP2013542944 A JP 2013542944A
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- JP
- Japan
- Prior art keywords
- pyrithione
- iron
- personal care
- care composition
- metal salt
- 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 41
- 229960002026 pyrithione Drugs 0.000 title claims abstract description 39
- OEUUFNIKLCFNLN-LLVKDONJSA-N chembl432481 Chemical compound OC(=O)[C@@]1(C)CSC(C=2C(=CC(O)=CC=2)O)=N1 OEUUFNIKLCFNLN-LLVKDONJSA-N 0.000 title claims abstract description 27
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 title claims abstract 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229910052751 metal Inorganic materials 0.000 claims abstract description 40
- 239000002184 metal Substances 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 34
- 229910052742 iron Inorganic materials 0.000 claims abstract description 25
- 239000003112 inhibitor Substances 0.000 claims abstract description 12
- 229940043810 zinc pyrithione Drugs 0.000 claims description 17
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical group [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 11
- -1 iron ions Chemical class 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002738 chelating agent Substances 0.000 claims description 8
- 150000003751 zinc Chemical class 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
- 238000005194 fractionation Methods 0.000 claims description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 3
- 229940075525 iron chelating agent Drugs 0.000 claims description 3
- 239000000797 iron chelating agent Substances 0.000 claims description 3
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 2
- CLCDXJPGDBNBMT-UHFFFAOYSA-N 1-oxo-2h-thiopyran-2-ol Chemical class OC1C=CC=CS1=O CLCDXJPGDBNBMT-UHFFFAOYSA-N 0.000 claims description 2
- LIPRKYKMVQPYPG-UHFFFAOYSA-N 3-Hydroxy-2H-pyran-2-one Chemical class OC1=CC=COC1=O LIPRKYKMVQPYPG-UHFFFAOYSA-N 0.000 claims description 2
- MLAWEJCHWVGJBZ-UHFFFAOYSA-N 3-hydroxysulfanyl-1h-pyridin-2-one Chemical class OSC1=CC=CNC1=O MLAWEJCHWVGJBZ-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 159000000009 barium salts Chemical class 0.000 claims description 2
- 150000001621 bismuth Chemical class 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 150000002815 nickel Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- FNXKBSAUKFCXIK-UHFFFAOYSA-M sodium;hydrogen carbonate;8-hydroxy-7-iodoquinoline-5-sulfonic acid Chemical class [Na+].OC([O-])=O.C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 FNXKBSAUKFCXIK-UHFFFAOYSA-M 0.000 claims description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 2
- QHNCWVQDOPICKC-UHFFFAOYSA-N copper;1-hydroxypyridine-2-thione Chemical group [Cu].ON1C=CC=CC1=S.ON1C=CC=CC1=S QHNCWVQDOPICKC-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 25
- 239000004094 surface-active agent Substances 0.000 description 11
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- CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 4
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
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- SFJPGSCMZIUEDJ-UHFFFAOYSA-N 2-[2-[[carboxy-(2-hydroxy-4-methylphenyl)methyl]amino]ethylamino]-2-(2-hydroxy-4-methylphenyl)acetic acid Chemical compound OC1=CC(C)=CC=C1C(C(O)=O)NCCNC(C(O)=O)C1=CC=C(C)C=C1O SFJPGSCMZIUEDJ-UHFFFAOYSA-N 0.000 description 3
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- SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical class ON1C=CC=CC1=O SNUSZUYTMHKCPM-UHFFFAOYSA-N 0.000 description 2
- WSFIDIJAAUEJLT-UHFFFAOYSA-N 2-(2-hydroxy-4-methylphenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C(O)=C1 WSFIDIJAAUEJLT-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 102000008133 Iron-Binding Proteins Human genes 0.000 description 2
- 108010035210 Iron-Binding Proteins Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
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- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
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- MARYDOMJDFATPK-UHFFFAOYSA-N 3-hydroxy-1h-pyridine-2-thione Chemical class OC1=CC=CN=C1S MARYDOMJDFATPK-UHFFFAOYSA-N 0.000 description 1
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
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Abstract
Description
本発明において、鉄キレート化剤類は、以下の特徴を有し得るが、これらに限定されない。
1.第1鉄(鉄II)又は第2鉄(III)のいずれかの形態の鉄イオンに対する親和性、
2.2以上の配位座数を有する記述1(上述)の材料(配位座数とは、鉄イオンに結合する分子の群の数である)、
3.記述2のサブセットである化学的記載:
a.天然材料又は合成(例えばDFO、DFT)材料のいずれか、
b.以下の化学的部類の物質:
i.カテコール類及びフェノール類
ii.ヒドロキサメート類(デスフェリオキサミン(DFO))
iii.チオヒドロキサメート類
iv.ヒドロキシピリドン類(CP20、ピロクトン、シクロピロックス、HP−101)
v.ヒドロキシチオピリドン類
vi.ヒドロキシピリジンチオン類
vii.アミノカルボキシレート類(EDTA、DTPA)
viii.ピリジン類(2,2’−ビピリジン、1,10−フェナトリン、TPEN)
ix.ヒドロキシカルボキシレート類
x.アロイルヒドラゾン類(PIH)
xi.ヒドロキシキノリン類(8−ヒドロキシキノリン)
xii.ヒドロキシピロン類(マルトール、エチルマルトール)
xiii.ヒドロキシチオピロン類
及びこれらの化学的部類の組み合わせを表す分子。
一実施形態では、本発明は、ピリチオン又はピリチオンの多価金属塩を含んでもよい。血小板状及び針晶構造などの、いかなる形態の多価金属のピリチオン塩類も用いてよい。一実施形態では、本明細書で用いるための塩には、多価金属類のマグネシウム、バリウム、ビスマス、ストロンチウム、銅、亜鉛、カドミウム、ジルコニウム及びこれらの混合物、更なる実施形態では亜鉛から形成されるものが挙げられる。更なる実施形態では、本明細書で使用されるのは、1−ヒドロキシ−2−ピリジンチオンの亜鉛塩(「亜鉛ピリチオン」又は「ZPT」として知られている)、更に別の実施形態では、小板状粒子の形態のZPTであり、この粒子は最大約20μmの平均寸法を有し、一実施形態では、最大約5μmの平均寸法を有し、更に別の実施形態では、最大約2.5μmの平均寸法を有する。
本発明の一実施形態では、鉄キレート化剤は疎水性である。物質が菌類の細胞膜を越えてその効果を発揮する確率を増大させるために、十分な疎水性が必要とされる。AlogPは、物質の疎水性の評価基準となり得るが、これは化学的フラグメントの方法を基に計算される。数字が正であるほど分子は疎水性であり、膜の透過性を高めるためには、その最小値が必要とされると考えられている。孤立分子の固有の疎水性をAlogPとして計算できる。荷電基を有する物質は、はるかに疎水性が小さい傾向があり、更には極めて水溶性になることが多い。
配位子と金属(この場合は鉄)との間の結合の強さを、鉄親和性と呼ぶことができる。理論に束縛されるわけではないが、最小の鉄親和性を満たす物質は、鉄細胞代謝を妨害する可能性を有し、それによって、細胞生理に圧力を加えている他の物質と組み合わされたときに抗菌活性を増大させる。
IC50値は、成長阻害を起こす阻害物質濃度であり、培養物の光学密度は、未処置の対照の1/2増加した。
分画阻害物質濃度(FIC)は、抗菌相互作用を評価するための従来からの手法である。本発明の一実施形態では、FICを使用して、組織培養設定における抗マラセチア活性に対する2つの化学物質類の組み合わせ効果を判断する。
1.各FICアッセイを2回行う。
2.低濃度のマラセチアフルフール7982細胞を96ウェルプレートの各ウェルに植菌する。
3.化学物質#1(我々のアッセイでは、これは常にZPT)を、最終濃度12.5ppmから始まって0ppmで終わるように、右から左にプレートの各列を横切って滴定する(2x濃度減少)。
4.化学物質#2を、最終濃度400ppm又は800ppm(効力に応じて)から始まって0ppmで終わるように、プレートの各行を下に向かって滴定する(2x濃度減少)。
5.プレートを33℃、RH60%で2日間、攪拌しながらインキュベートする。
6.次いで、分光光度計を使用して光学密度(OD)を測定する。
1.OD<=0.6であるなら成長の阻害が判定され(これは、ウェルでの成長が、可能である最大濃度の少なくとも50%に達しなかったことを示す)、ウェルは「−」で印される。
2.OD>0.6であるなら、成長の阻害がないことが判定され、ウェルは「+」で印される。
3.成長を阻害する化学物質#1の最低濃度値(単独で、及び化学物質#2の効力を促進させる化学物質#1の最低濃度の両方)が判定される(付録1を参照)。
4.同様に、成長を阻害する化学物質#2の最低濃度(単独で、及び化学物質#1の効力を促進させる化学物質#2の最低濃度の両方)が判定される(付録1を参照)。
5.以下の計算を使って、2つのプレートのFIC値を算出する。
以下は、仮定的なFICを解釈するプロセスの例であるが、全ての数値は、試験された化学物質の最終濃度を100万分の1の単位で表している。
(0.20/6.25)+(3.13/400.00)=0.04
(0.04+0.04)/2=0.04
(2)Arch Chemicals,Inc.より
*分画阻害濃度、FIC≦0.5は相乗活性を表し、0.5<FIC≦1.0は付加を表す(1.0超のFICは、中性又は拮抗のいずれか)。参考文献:R.Bharadwajら、Indian J Pharmacol 2003,35,220。
Claims (12)
- a)有効量のピリチオン又はピリチオンの多価金属塩と、
b)有効量の鉄キレート化剤又は鉄をキレート化する物質と、
を含み、
前記鉄キレート化剤と前記ピリチオン又はピリチオンの多価金属塩との組み合わせが、1以下の分画阻害物質濃度を有する、パーソナルケア組成物。 - 前記鉄キレート化剤が疎水性である、請求項1に記載のパーソナルケア組成物。
- 前記鉄キレート化剤が、0.4以上のAlogP値を有する、請求項1又は2に記載のパーソナルケア組成物。
- 前記鉄キレート化剤が、log K1>3.5である、請求項1〜3のいずれか一項に記載のパーソナルケア組成物。
- 前記ピリチオン又はピリチオンの多価金属塩が亜鉛ピリチオンである、請求項1〜4のいずれか一項に記載のパーソナルケア組成物。
- 前記ピリチオン又はピリチオンの多価金属塩が銅ピリチオンである、請求項1〜5のいずれか一項に記載のパーソナルケア組成物。
- 前記鉄キレート化剤が、第1鉄(鉄II)又は第2鉄(III)のいずれかの形態の鉄イオンに対する親和性を有する材料、2以上の配位座数を形成する第1鉄(鉄II)又は第2鉄(III)のいずれかの鉄イオンに対する親和性を有する材料、カテコール類及びフェノール類、ヒドロキサメート類、チオヒドロキサメート類、ヒドロキシピリドン類、ヒドロキシチオピリドン類、ヒドロキシピリジンチオン類、アミノカルボキシレート類、ピリジン類、ヒドロキシカルボキシレート類、アロイルヒドラゾン類、ヒドロキシキノリン類、ヒドロキシピロン類、ヒドロキシチオピロン類、並びにこれらの混合物からなる群から選択される、請求項1〜6のいずれか一項に記載のパーソナルケア組成物。
- 前記鉄キレート化剤が、天然キレート化剤、合成キレート化剤、及びこれらの混合物を含む群から選択される、請求項1〜7のいずれか一項に記載のパーソナルケア組成物。
- 前記鉄キレート化剤が、金属塩、好ましくは亜鉛塩、カルシウム塩、銀塩、ニッケル塩、マグネシウム塩、バリウム塩、ビスマス塩、及びこれらの混合物からなる群から選択される金属塩であり、より好ましくは前記鉄キレート化剤が、亜鉛の金属塩である、請求項1〜8のいずれか一項に記載のパーソナルケア組成物。
- 前記ピリチオン又はピリチオンの多価金属塩が、0.01%〜5%で存在する、請求項1〜9のいずれか一項に記載のパーソナルケア組成物。
- 前記鉄キレート化剤が、0.01%〜5%で存在する、請求項1〜10のいずれか一項に記載のパーソナルケア組成物。
- 前記鉄キレート化剤と前記ピリチオン又はピリチオンの多価金属塩との組み合わせが、0.5以下の分画阻害物質濃度を有する、請求項1〜11のいずれか一項に記載のパーソナルケア組成物。
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JP2013543847A (ja) * | 2010-10-28 | 2013-12-09 | ザ プロクター アンド ギャンブル カンパニー | アコニターゼ阻害による微生物増殖の阻害 |
JP2020522523A (ja) * | 2017-06-30 | 2020-07-30 | ザ プロクター アンド ギャンブル カンパニーThe Procter & Gamble Company | 2−ピリジノール−n−オキシド材料及び鉄キレート剤を含むヘアケア組成物 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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BR112015008046A2 (pt) * | 2012-10-12 | 2017-07-04 | Arch Chem Inc | composições biocidais que compreendem quelantes de ferro |
WO2014169464A1 (en) | 2013-04-18 | 2014-10-23 | The Procter & Gamble Company | Personal care compositions containing zinc pyrithione and zinc-phosphonate complex |
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CN112118824B (zh) * | 2018-05-15 | 2023-05-23 | 宝洁公司 | 协同抗氧化剂组合物 |
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JP7288092B2 (ja) | 2019-06-28 | 2023-06-06 | ザ プロクター アンド ギャンブル カンパニー | 相乗的抗炎症性組成物 |
WO2020264076A1 (en) * | 2019-06-28 | 2020-12-30 | The Procter & Gamble Company | Light augmented treatment method |
CN110839633B (zh) * | 2019-08-30 | 2021-04-30 | 苏州科技大学 | 2-巯基吡啶-n-氧化物三价钴盐配合物的抗菌应用 |
US11980612B2 (en) | 2020-06-26 | 2024-05-14 | The Procter & Gamble Company | Synergistic anti-inflammatory compositions |
US11701316B2 (en) | 2020-12-18 | 2023-07-18 | The Procter & Gamble Company | Synergistic anti-inflammatory compositions |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001516359A (ja) * | 1997-03-14 | 2001-09-25 | アーチ ケミカルズ,インコーポレイテッド | ピリチオン塩粒子の製造方法 |
JP2003503333A (ja) * | 1999-06-25 | 2003-01-28 | ザ、プロクター、エンド、ギャンブル、カンパニー | 局所用抗菌組成物 |
WO2003088965A1 (en) * | 2002-04-22 | 2003-10-30 | The Procter & Gamble Company | Use of materials having zinc ionophoric behavior |
JP2005524690A (ja) * | 2002-04-22 | 2005-08-18 | ザ プロクター アンド ギャンブル カンパニー | 水性界面活性剤組成物中に亜鉛含有物質を含むパーソナルケア組成物 |
JP2005535667A (ja) * | 2002-07-15 | 2005-11-24 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 毛髪および/または頭皮トリートメント用組成物 |
JP2006045127A (ja) * | 2004-08-05 | 2006-02-16 | Lion Corp | フケ・痒み防止組成物 |
JP2006045126A (ja) * | 2004-08-05 | 2006-02-16 | Lion Corp | フケ・痒み防止組成物 |
JP2007223917A (ja) * | 2006-02-21 | 2007-09-06 | Nippon Chem Ind Co Ltd | 抗菌剤 |
JP2010524888A (ja) * | 2007-04-18 | 2010-07-22 | ピエール、ファブレ、デルモ‐コスメティーク | シクロピロクスオラミンおよび亜鉛ピリチオンを含む抗真菌泡ならびにその医療用途および化粧用途 |
JP2010534063A (ja) * | 2007-07-20 | 2010-11-04 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | ランチビオティックス及びこれらの使用 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE406221A (ja) | 1933-11-15 | |||
US2438091A (en) | 1943-09-06 | 1948-03-16 | American Cyanamid Co | Aspartic acid esters and their preparation |
BE498391A (ja) | 1944-10-16 | |||
BE498392A (ja) | 1945-11-09 | |||
US2528378A (en) | 1947-09-20 | 1950-10-31 | John J Mccabe Jr | Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same |
US2658072A (en) | 1951-05-17 | 1953-11-03 | Monsanto Chemicals | Process of preparing amine sulfonates and products obtained thereof |
US2809971A (en) | 1955-11-22 | 1957-10-15 | Olin Mathieson | Heavy-metal derivatives of 1-hydroxy-2-pyridinethiones and method of preparing same |
US3236733A (en) | 1963-09-05 | 1966-02-22 | Vanderbilt Co R T | Method of combatting dandruff with pyridinethiones metal salts detergent compositions |
US3332880A (en) | 1965-01-04 | 1967-07-25 | Procter & Gamble | Detergent composition |
US3761418A (en) | 1967-09-27 | 1973-09-25 | Procter & Gamble | Detergent compositions containing particle deposition enhancing agents |
US3753196A (en) | 1971-10-05 | 1973-08-14 | Kulite Semiconductor Products | Transducers employing integral protective coatings and supports |
US3929678A (en) | 1974-08-01 | 1975-12-30 | Procter & Gamble | Detergent composition having enhanced particulate soil removal performance |
US4379753A (en) | 1980-02-07 | 1983-04-12 | The Procter & Gamble Company | Hair care compositions |
US4345080A (en) | 1980-02-07 | 1982-08-17 | The Procter & Gamble Company | Pyridinethione salts and hair care compositions |
US4323683A (en) | 1980-02-07 | 1982-04-06 | The Procter & Gamble Company | Process for making pyridinethione salts |
US4470982A (en) * | 1980-12-22 | 1984-09-11 | The Procter & Gamble Company | Shampoo compositions |
GB8407999D0 (en) * | 1984-03-28 | 1984-05-10 | Procter & Gamble Ltd | Hair care compositions |
US4835149A (en) * | 1986-11-13 | 1989-05-30 | Basf Corporation | Solubilization of salts of pyridine-2-thiol-1-oxide |
US5886031A (en) * | 1997-01-27 | 1999-03-23 | Pacific Corporation | Hair-care cosmetic compositions having dandruff formation-suppressing effect |
US5968539A (en) * | 1997-06-04 | 1999-10-19 | Procter & Gamble Company | Mild, rinse-off antimicrobial liquid cleansing compositions which provide residual benefit versus gram negative bacteria |
WO2007106622A2 (en) * | 2006-02-03 | 2007-09-20 | Carl Lawyer | Fungicidal formulation and method of use |
WO2009053163A1 (en) * | 2007-10-25 | 2009-04-30 | Unilever Plc | Hair care composition |
WO2011000566A2 (en) * | 2009-06-30 | 2011-01-06 | Savira Pharmaceuticals Gmbh | Compounds and pharmaceutical compositions for the treatment of negative-sense ssrna virus infections |
CA2779147A1 (en) * | 2009-10-28 | 2011-05-12 | Eugene B. Guthery | Rosacea topical skin treatment method and formulation |
-
2011
- 2011-10-28 BR BR112013010241-1A patent/BR112013010241B1/pt active IP Right Grant
- 2011-10-28 MX MX2013004557A patent/MX350993B/es active IP Right Grant
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- 2011-10-28 WO PCT/US2011/058313 patent/WO2012058557A2/en active Application Filing
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Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001516359A (ja) * | 1997-03-14 | 2001-09-25 | アーチ ケミカルズ,インコーポレイテッド | ピリチオン塩粒子の製造方法 |
JP2003503333A (ja) * | 1999-06-25 | 2003-01-28 | ザ、プロクター、エンド、ギャンブル、カンパニー | 局所用抗菌組成物 |
JP2007284459A (ja) * | 1999-06-25 | 2007-11-01 | Procter & Gamble Co | 局所用抗菌組成物 |
WO2003088965A1 (en) * | 2002-04-22 | 2003-10-30 | The Procter & Gamble Company | Use of materials having zinc ionophoric behavior |
JP2005524690A (ja) * | 2002-04-22 | 2005-08-18 | ザ プロクター アンド ギャンブル カンパニー | 水性界面活性剤組成物中に亜鉛含有物質を含むパーソナルケア組成物 |
JP2005526111A (ja) * | 2002-04-22 | 2005-09-02 | ザ プロクター アンド ギャンブル カンパニー | 亜鉛イオノフォア性を有する物質の使用 |
JP2005535667A (ja) * | 2002-07-15 | 2005-11-24 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 毛髪および/または頭皮トリートメント用組成物 |
JP2006045127A (ja) * | 2004-08-05 | 2006-02-16 | Lion Corp | フケ・痒み防止組成物 |
JP2006045126A (ja) * | 2004-08-05 | 2006-02-16 | Lion Corp | フケ・痒み防止組成物 |
JP2007223917A (ja) * | 2006-02-21 | 2007-09-06 | Nippon Chem Ind Co Ltd | 抗菌剤 |
JP2010524888A (ja) * | 2007-04-18 | 2010-07-22 | ピエール、ファブレ、デルモ‐コスメティーク | シクロピロクスオラミンおよび亜鉛ピリチオンを含む抗真菌泡ならびにその医療用途および化粧用途 |
JP2010534063A (ja) * | 2007-07-20 | 2010-11-04 | リージェンツ オブ ザ ユニバーシティ オブ ミネソタ | ランチビオティックス及びこれらの使用 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013543847A (ja) * | 2010-10-28 | 2013-12-09 | ザ プロクター アンド ギャンブル カンパニー | アコニターゼ阻害による微生物増殖の阻害 |
JP2016006105A (ja) * | 2010-10-28 | 2016-01-14 | ザ プロクター アンド ギャンブルカンパニー | アコニターゼ阻害による微生物増殖の阻害 |
JP2020522523A (ja) * | 2017-06-30 | 2020-07-30 | ザ プロクター アンド ギャンブル カンパニーThe Procter & Gamble Company | 2−ピリジノール−n−オキシド材料及び鉄キレート剤を含むヘアケア組成物 |
JP7071407B2 (ja) | 2017-06-30 | 2022-05-18 | ザ プロクター アンド ギャンブル カンパニー | 2-ピリジノール-n-オキシド材料及び鉄キレート剤を含むヘアケア組成物 |
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JP5746357B2 (ja) | 2015-07-08 |
CN103347524B (zh) | 2016-03-16 |
MX350993B (es) | 2017-09-27 |
BR112013010241A2 (pt) | 2016-07-05 |
EP2632470A2 (en) | 2013-09-04 |
WO2012058557A3 (en) | 2013-09-12 |
EP2632470B1 (en) | 2018-02-28 |
BR112013010241B1 (pt) | 2018-03-20 |
WO2012058557A2 (en) | 2012-05-03 |
MX2013004557A (es) | 2013-06-07 |
CN103347524A (zh) | 2013-10-09 |
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