JP2006265104A - 皮膚外用剤用リン脂質誘導体、皮膚外用剤、リポソームおよび脂肪乳剤 - Google Patents
皮膚外用剤用リン脂質誘導体、皮膚外用剤、リポソームおよび脂肪乳剤 Download PDFInfo
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- JP2006265104A JP2006265104A JP2005080986A JP2005080986A JP2006265104A JP 2006265104 A JP2006265104 A JP 2006265104A JP 2005080986 A JP2005080986 A JP 2005080986A JP 2005080986 A JP2005080986 A JP 2005080986A JP 2006265104 A JP2006265104 A JP 2006265104A
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005080986A JP2006265104A (ja) | 2005-03-22 | 2005-03-22 | 皮膚外用剤用リン脂質誘導体、皮膚外用剤、リポソームおよび脂肪乳剤 |
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| JP2005080986A JP2006265104A (ja) | 2005-03-22 | 2005-03-22 | 皮膚外用剤用リン脂質誘導体、皮膚外用剤、リポソームおよび脂肪乳剤 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008088133A (ja) * | 2006-10-04 | 2008-04-17 | Kose Corp | ベシクル組成物、及びそれを用いた皮膚外用剤 |
| WO2010143970A3 (en) * | 2009-06-08 | 2011-11-03 | Epitarget As | Acoustically sensitive drug delivery particles comprising non-lamellar forming phosphatidylcholine |
| EP3165591B1 (en) * | 2014-07-02 | 2024-05-22 | Nissui Corporation | Method for producing marine product-derived monovalent unsaturated free fatty acids or lower alcohol esters thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03153628A (ja) * | 1989-11-13 | 1991-07-01 | Nippon Oil & Fats Co Ltd | 高度不飽和脂肪酸含有脂質の可溶化組成物 |
| JP2000247987A (ja) * | 1998-12-28 | 2000-09-12 | Ymc Co Ltd | 高度水素添加レシチン |
| JP2000281688A (ja) * | 1999-03-29 | 2000-10-10 | Nof Corp | 混合酸型１，２−ジアシル−３−グリセロリン脂質の製造方法 |
| JP2002275187A (ja) * | 2001-03-21 | 2002-09-25 | Nof Corp | ホスファチジルコリンの製造方法 |
| JP2003169692A (ja) * | 2001-12-07 | 2003-06-17 | Meito Sangyo Co Ltd | リン脂質誘導体又はその塩の製造方法 |
| JP2004529875A (ja) * | 2001-02-15 | 2004-09-30 | マックス−プランク−ゲゼルシャフト・ツア・フェルデルング・デア・ヴィッセンシャフテン・エー・ファオ | 制御された放出温度を有する熱不安定性リポソーム |
-
2005
- 2005-03-22 JP JP2005080986A patent/JP2006265104A/ja active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03153628A (ja) * | 1989-11-13 | 1991-07-01 | Nippon Oil & Fats Co Ltd | 高度不飽和脂肪酸含有脂質の可溶化組成物 |
| JP2000247987A (ja) * | 1998-12-28 | 2000-09-12 | Ymc Co Ltd | 高度水素添加レシチン |
| JP2000281688A (ja) * | 1999-03-29 | 2000-10-10 | Nof Corp | 混合酸型１，２−ジアシル−３−グリセロリン脂質の製造方法 |
| JP2004529875A (ja) * | 2001-02-15 | 2004-09-30 | マックス−プランク−ゲゼルシャフト・ツア・フェルデルング・デア・ヴィッセンシャフテン・エー・ファオ | 制御された放出温度を有する熱不安定性リポソーム |
| JP2002275187A (ja) * | 2001-03-21 | 2002-09-25 | Nof Corp | ホスファチジルコリンの製造方法 |
| JP2003169692A (ja) * | 2001-12-07 | 2003-06-17 | Meito Sangyo Co Ltd | リン脂質誘導体又はその塩の製造方法 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008088133A (ja) * | 2006-10-04 | 2008-04-17 | Kose Corp | ベシクル組成物、及びそれを用いた皮膚外用剤 |
| WO2010143970A3 (en) * | 2009-06-08 | 2011-11-03 | Epitarget As | Acoustically sensitive drug delivery particles comprising non-lamellar forming phosphatidylcholine |
| EP3165591B1 (en) * | 2014-07-02 | 2024-05-22 | Nissui Corporation | Method for producing marine product-derived monovalent unsaturated free fatty acids or lower alcohol esters thereof |
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