# US 5,352,805 A · Water soluble derivatives of taxol

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- Number: US 5,352,805 A
- Document ID: US5352805A
- Status: Granted
- Kind: A
- Application number: 07/694,077
- Filed: 1991-05-01
- Granted: 1994-10-04
- Earliest claimed: 1990-08-28
- Assignees: Virginia Tech Intellectual Properties, Inc.
- Inventors: David G. I. Kingston; Zhi-Yang Zhao
- Web page: https://patentgrep.com/patent/US5352805A

## CPC

- C07D 305/14: condensed with carbocyclic rings or ring systems
- A61P 35/00: Antineoplastic agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## 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)-l,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.

## Claims

### Claim 1

A process, comprising the reaction of a 2'-O-acyl acid taxol with a glycol.