Title:
【発明の名称】アジュバントおよび免疫刺激活性を有するトリテルペンサポニンアナログ
Document Type and Number:
Japanese Patent JP2002504099
Kind Code:
A
Abstract:
The present invention is directed to novel chemical compounds in which a lipophilic moiety such as a lipid, fatty acid, polyethylene glycol or terpene is covalently attached to a non-acylated or desacylated triterpene saponin via a carboxyl group present on the 3-O-glucuronic acid of the triterpene saponin. The attachment of a lipophile moiety to the 3-O-glucuronic acid of a saponin such as Quillaja desacylsaponin, lucyoside P, or saponin from Gypsophila, Saponaria and Acanthophyllum enhances their adjuvant effects on humoral and cell mediated immunity. Additionally, the attachment of a lipophile moiety to the 3-O-glucuronic acid residue of non- or des-acylsaponin yields a saponin analog that is easier to purify, less toxic, chemically more stable, and possesses equal or better adjuvant properties than the original saponin.
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Inventors:
Marsani, Dante Jay.
Application Number:
JP55055598A
Publication Date:
February 05, 2002
Filing Date:
May 20, 1998
Export Citation:
Assignee:
Galenica Pharmaceuticals, Inc.
International Classes:
A61K31/704; A61K36/00; A61K39/39; A61K47/48; A61P37/04; A61P43/00; C07H15/256; A61K31/56; C07J63/00; (IPC1-7): C07J63/00; A61K31/56; A61K31/704; A61K35/78; A61P37/04; A61P43/00
Domestic Patent References:
| JPH07509440A | 1995-10-19 | |||
| JPH07504156A | 1995-05-11 | |||
| JPH04501714A | 1992-03-26 |
Other References:
JPN6009013310, ＳＯＬＴＹＳＩＫ， Ｓ． ｅｔ ａｌ．, "Ｓｔｒｕｃｔｕｒｅ／ｆｕｎｃｔｉｏｎ ｓｔｕｄｉｅｓ ｏｆ ＱＳ−２１ ａｄｊｕｖａｎｔ： ａｓｓｅｓｓｍｅｎｔ ｏｆ ｔｒｉｔｅｒｐｅｎｅ ａｌｄｅｈｙｄｅ ａｎｄ ｇｌｕｃｕｒｏｎｉｃ ａｃｉｄ", Ｖａｃｃｉｎｅ, 1995, Ｖｏｌｕｍｅ １３， Ｉｓｓｕｅ １５, Ｐａｇｅｓ １４０３−１４１０
JPN6009013311, ＢＯＭＦＯＲＤ， Ｒ． ｅｔ ａｌ．, "Ａｄｊｕｖａｎｔｉｃｉｔｙ ａｎｄ ＩＳＣＯＭ ｆｏｒｍａｔｉｏｎ ｂｙ ｓｔｒｕｃｔｕｒａｌｌｙ ｄｉｖｅｒｓｅ ｓａｐｏｎｉｎｓ", Ｖａｃｃｉｎｅ, 1992, Ｖｏｌｕｍｅ １０， Ｉｓｓｕｅ ９，, Ｐａｇｅｓ ５７２−５７７
JPN6009013312, ＳＡＩＴＯ， Ｓ． ｅｔ ａｌ．, "Ｓｙｎｔｈｅｔｉｃ ｓｔｕｄｉｅｓ ｏｎ ｔｈｅ ｒｅｌａｔｉｏｎｓｈｉｐ ｂｅｔｗｅｅｎ ａｎｔｉ−ＨＩＶ ａｃｔｉｖｉｔｉｅｓ ａｎｄ ｍｉｃｅｌｌｅ ｆｏｒｍｉｎｇ ａｂｉｌｉｔｉｅｓ ｏｆ ｖ", Ｅｕｒｏｐｅａｎ Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ, 1996, Ｖｏｌｕｍｅ ３１， Ｉｓｓｕｅ ５, Ｐａｇｅｓ ３６５−３８１
JPN6009013311, ＢＯＭＦＯＲＤ， Ｒ． ｅｔ ａｌ．, "Ａｄｊｕｖａｎｔｉｃｉｔｙ ａｎｄ ＩＳＣＯＭ ｆｏｒｍａｔｉｏｎ ｂｙ ｓｔｒｕｃｔｕｒａｌｌｙ ｄｉｖｅｒｓｅ ｓａｐｏｎｉｎｓ", Ｖａｃｃｉｎｅ, 1992, Ｖｏｌｕｍｅ １０， Ｉｓｓｕｅ ９，, Ｐａｇｅｓ ５７２−５７７
JPN6009013312, ＳＡＩＴＯ， Ｓ． ｅｔ ａｌ．, "Ｓｙｎｔｈｅｔｉｃ ｓｔｕｄｉｅｓ ｏｎ ｔｈｅ ｒｅｌａｔｉｏｎｓｈｉｐ ｂｅｔｗｅｅｎ ａｎｔｉ−ＨＩＶ ａｃｔｉｖｉｔｉｅｓ ａｎｄ ｍｉｃｅｌｌｅ ｆｏｒｍｉｎｇ ａｂｉｌｉｔｉｅｓ ｏｆ ｖ", Ｅｕｒｏｐｅａｎ Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ, 1996, Ｖｏｌｕｍｅ ３１， Ｉｓｓｕｅ ５, Ｐａｇｅｓ ３６５−３８１
Attorney, Agent or Firm:
Shusaku Yamamoto