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US5059699A Expired / Lapsed US ⏱️ 0.0 years remaining

Water soluble derivatives of taxol

Assignee: Virginia Tech Intellectual Properties Inc
•
Filing: 1990-08-28
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Granted: 1991-10-22
•
Expires: 2010-08-28
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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 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.

Inventors

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

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 17:26
CPC Classifications
C; C07; C07D; C07D305/00; C07D305/14; A; A61; A61P; A61P35/00

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 21 words
A taxol compound having the following structure: ##STR9## wherein: X is selected from the group consisting of H, alkyls, and aryls.
Claim 2
Dependent Claim 21 words
A taxol compound having the following structure: ##STR9## wherein: X is selected from the group consisting of H, alkyls, and aryls.
Claim 3
Dependent Claim 10 words
A compound according to claim 1, wherein: X is H.
Claim 4
Dependent Claim 38 words
A water soluble taxol compound having the following structure: ##STR10## wherein: X is selected from the group consisting of H, alkyls, and aryls; and M is selected from the group consisting of H, alkaline metals, and ammonio groups.
Claim 5
Dependent Claim 38 words
A water soluble taxol compound having the following structure: ##STR10## wherein: X is selected from the group consisting of H, alkyls, and aryls; and M is selected from the group consisting of H, alkaline metals, and ammonio groups.
Claim 6
Dependent Claim 14 words
A compound according to claim 3, wherein: X is H, and M is Na.
Claim 7
Dependent Claim 79 words
A water soluble taxol compound having the following structure: ##STR11## wherein: R is selected from the group consisting of: --(CH y ) n --CO--NH--(CH 2 ) z --SO 2 O--M, and --(CH y ) n --CO--O--(CH 2 ) z --OH; wherein: M is selected from the group consisting of H, alkaline metals, and ammonio groups, n is 1 to 3, y is 1 to 2, provided y is not 1 when is 1, and z is 2 to 3.
Claim 8
Dependent Claim 79 words
A water soluble taxol compound having the following structure: ##STR11## wherein: R is selected from the group consisting of: --(CH y ) n --CO--NH--(CH 2 ) z --SO 2 O--M, and --(CH y ) n --CO--O--(CH 2 ) z --OH; wherein: M is selected from the group consisting of H, alkaline metals, and ammonio groups, n is 1 to 3, y is 1 to 2, provided y is not 1 when is 1, and z is 2 to 3.
Claim 9
Dependent Claim 17 words
A compound according to claim 5, wherein: Y is 2, n is 2, and z is 2.
Claim 10
Dependent Claim 17 words
A compound according to claim 5, wherein: Y is 2, n is 2, and z is 3.
Claim 11
Dependent Claim 12 words
A compound according to claim 5, wherein: M is a quaternary ammonium.

References Cited (Backward Citations)

US4942184A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-10-21 1995-04-22 1995-10-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-10-21 1999-04-22 1999-10-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-10-21 2003-04-22 2003-10-22 $7700.00 Window Closed / Lapsed

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