Water soluble derivatives of taxol

Details Water soluble derivatives of taxol Water soluble derivatives of taxol

1990-08-28

1991-10-22

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514449, C07D30514, A61K 31335

Patent

active

050596993

ABSTRACT:
Sulfonated 2'-acryloyltaxol and sulfonated 2'-O-acyl acid taxol derivatives are synthesized which have improved water solubility and stability while maintaining bio-activity. In particular, 2'-[(3-sulfo-1-oxopropyl)oxy]taxol sodium salt is synthesized by reacting taxol with acrylic acid, and subsequently reacting the 2'-acryloyltaxol with bisulfite in a Michael reaction. 2'-{[4-((2-sulfoethyl)amino)-1,4-dioxobutyl]oxy}taxol sodium salt and 2'-{[4-((3-sulfopropyl)amino-1,4-dioxobutyl]oxy}taxol sodium salt are synthesized by reacting 2'-succinyltaxol with the tetrabutylammonium salts of taurine and 3-aminopropyl sulfonic acid, respectively, and subsequently exchanging the ammonium with sodium. Glycol derivatives of 2'-O-acyl acid taxols with improved water solubility are synthesized by reaction of a glycol with 2'-O-acyl acid taxol.

REFERENCES:
patent: 4942184 (1990-07-01), Haugwitz et al.
Wani et al., J. Am. Chem. Soc., 1971, 93, 2325.
McGuire et al., Ann. Int. Med., 1989, 111, 273-279.
Magri et al., J. Nat. Prod., vol. 51, No. 2, 298-306, Mar.-Apr. 1988.
Duetsch et al., J. Med. Chem., 1989, 32, 788-792.

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