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US5278324A Expired / Lapsed US ⏱️ 0.0 years remaining

Water soluble derivatives of taxol

Assignee: VA POLYTECHNIC INSTITUTE & STATE UNIV
•
Filing: 1991-10-15
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Granted: 1994-01-11
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Expires: 2011-10-15
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Abstract

Abstract Sulfonated 2'-acryloyltaxol and sulfonated 2'-O-acyl acid taxol derivatives are synthesized which have improved water solubility and stability while maintaining bioactivity. 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.

Inventors

  • 👤 David G. I. Kingston
  • 👤 Zhi-Yang Zhao

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 09:35
CPC Classifications
C; C07; C07D; C07D305/00; C07D305/14

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 49 words
A taxol compound having the following structure: ##STR9## wherein: X, Y, and Z are selected from the group consisting of H, alkyl, and aryl; provided that when Y is H, X is not the same as Z; and when Z is H, Y is not the same as X.
Claim 2
Dependent Claim 49 words
A taxol compound having the following structure: ##STR9## wherein: X, Y, and Z are selected from the group consisting of H, alkyl, and aryl; provided that when Y is H, X is not the same as Z; and when Z is H, Y is not the same as X.
Claim 3
Dependent Claim 10 words
The taxol compound of claim 1, wherein X is H.
Claim 4
Dependent Claim 23 words
The taxol compound of claim 2, wherein Y is selected from the group consisting of CH 3 and C 6 H 5 .
Claim 5
Dependent Claim 82 words
A water soluble taxol compound having the following structure: ##STR10## wherein: W, X, Y, and Z are selected from the group consisting of H, alkyl, and aryl; provided that when W and Y are H, X is not the same as Z; when X and Y are H, W is not the same as Z; when W and Z are H, X is not the same as Y; and when X and Z are H, W is not the same as Y.
Claim 6
Dependent Claim 82 words
A water soluble taxol compound having the following structure: ##STR10## wherein: W, X, Y, and Z are selected from the group consisting of H, alkyl, and aryl; provided that when W and Y are H, X is not the same as Z; when X and Y are H, W is not the same as Z; when W and Z are H, X is not the same as Y; and when X and Z are H, W is not the same as Y.
Claim 7
Dependent Claim 24 words
A compound according to claim 4, wherein said compound is more water soluble than taxol, and retains at least some of taxol's antineoplastic activity.
Claim 8
Dependent Claim 11 words
The compound of claim 4, wherein W and X are H.
Claim 9
Dependent Claim 26 words
The compound of claim 6, wherein Y is H and Z is selected from the group consisting of CH 3 and C 6 H 5 .

References Cited (Backward Citations)

US4942184A Cited
US5059699A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1997-01-10 1997-07-12 1998-01-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-01-10 2001-07-12 2002-01-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-01-10 2005-07-12 2006-01-11 $7700.00 Window Closed / Lapsed

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