US5194635A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Rearranged taxol compounds and method of using in testing of in vivo activity
Assignee: Virginia Tech Intellectual Properties Inc
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Filing: 1992-02-24
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Granted: 1993-03-16
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Expires: 2012-02-24
Abstract
Abstract In a preferred embodiment, taxol is treated with mesyl chloride to prepare a taxol derivative with a contracted A-ring, which has comparable activity to taxol in a tubulin depolymerization assay, and which shows cytotoxicity against KB cells in a cell culture assay. In an alternate preferred embodiment, taxol is treated with triethyloxonium tetrafluoroborate (Meerwein's reagent) to produce a taxol derivative with an opened oxetane ring. In another alternate preferred embodiment, reaction of taxol with acetyl chloride yields a taxol derivative in which the oxetane ring is opened and the A-ring is contracted. All of the aforementioned products show in vivo activity in KB cell culture assays. Further, the preferred compounds have different in vivo activities, which makes them ideal to form a range of standards for use in biological testing of other compounds.
Inventors
- 👤 David G. I. Kingston
- 👤 Gamini Samaranyake
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 17:30
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/44; C07D317/70; C07D305/00; C07D305/14
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
38 words
A rearranged taxol compound having the following structure: ##STR1## wherein R1 is C(O)CH 3 , R2 is H or Si(CH 2 CH 3 ) 3 , and R3 is H or Si(CH 2 CH 3 ) 3 .
Claim 2
Dependent Claim
38 words
A rearranged taxol compound having the following structure: ##STR1## wherein R1 is C(O)CH 3 , R2 is H or Si(CH 2 CH 3 ) 3 , and R3 is H or Si(CH 2 CH 3 ) 3 .
Claim 3
Dependent Claim
24 words
A rearranged taxol compound having the following structure: ##STR2## Wherein R1 is H or C(O)CH 3 , R2 is H or C(O)CH 3 .
Claim 4
Dependent Claim
24 words
A rearranged taxol compound having the following structure: ##STR2## Wherein R1 is H or C(O)CH 3 , R2 is H or C(O)CH 3 .
Claim 5
Dependent Claim
33 words
A process for producing taxol compounds with an A-ring contracted to five members, comprising the steps of: (a) protecting hydroxylated positions on taxol; and (b) reacting said protected taxol with a mesyl halide.
Claim 6
Dependent Claim
33 words
A process for producing taxol compounds with an A-ring contracted to five members, comprising the steps of: (a) protecting hydroxylated positions on taxol; and (b) reacting said protected taxol with a mesyl halide.
Claim 7
Dependent Claim
18 words
A process according to claim 3, further comprising the step of deprotecting said protected taxol to form A-Nor-taxol.
Claim 8
Dependent Claim
41 words
A process for producing taxol compounds with an A-ring contracted to five members, comprising the steps of: (a) reacting taxol with a trialkylsilyl halide to form a taxol silyl ether; and (b) reacting said taxol silyl ether with a mesyl halide.
Claim 9
Dependent Claim
41 words
A process for producing taxol compounds with an A-ring contracted to five members, comprising the steps of: (a) reacting taxol with a trialkylsilyl halide to form a taxol silyl ether; and (b) reacting said taxol silyl ether with a mesyl halide.
Claim 10
Dependent Claim
26 words
A process according to claim 5, further comprising the step of: (c) following step (b) removing sily groups on said taxol silyl ether to yield A-Nor-taxol.
Claim 11
Dependent Claim
14 words
The process of claim 5, wherein said reaction is carried out in basic conditions.
Claim 12
Dependent Claim
19 words
The process of claim 5, wherein said trialkylsilyl halide is triethylsilyl chloride, and said mesyl halide is mesyl chloride.
Claim 13
Dependent Claim
19 words
The process of claim 6, wherein step (c) is carried out by reacting said silylated A-Nor-taxol with pyridinium hydrofluoride.
Claim 14
Dependent Claim
14 words
A cytotoxic agent comprising a taxol compound having an A-ring contracted to five members.
Claim 15
Dependent Claim
14 words
A cytotoxic agent comprising a taxol compound having an A-ring contracted to five members.
Claim 16
Dependent Claim
15 words
The cytotoxic agent of claim 10, wherein said taxol compound has an intact oxetane D-ring.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-03-15 | 1996-09-14 | 1997-03-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-03-15 | 2000-09-14 | 2001-03-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-03-15 | 2004-09-14 | 2005-03-16 | $7700.00 | Window Closed / Lapsed |