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US5489601A
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Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them
Assignee: Florida State University
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Filing: 1993-07-20
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Granted: 1996-02-06
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Expires: 2013-07-20
Abstract
Abstract Taxane derivatives having a 3' pyridyl substituted C13 side chain.
Inventors
- 👤 Robert A. Holton
- 👤 Kasthuri Rengan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 08:27
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; C07C; C07C227/00; C07C227/22; C07C231/00; C07C231/12; C07C233/00; C07C233/64; C07C233/81; C07C233/82; C07C233/87; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D305/00; C07D305/14; C07D407/00; C07D407/02; C07D407/12; C07D409/00; C07D409/02; C07D409/12; C07F; C07F7/00; C07F7/003; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07C2601/00; C07C2601/12; C07C2601/14; C07C2601/16; C07C2603/00; C07C2603/56; C07C2603/58; C07C2603/60; C07C2603/62
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
329 words
A taxane having the formula ##STR27## wherein X 1 is --OX 6 , --SX 7 , or --NX 8 X 9 ; X 2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; X 3 is hydrogen; X 4 is pyridyl; X 5 is --CO 10 , --COOX 10 , --COSX 10 , --CONX 8 X 10 , or --SO 2 X 11 ; X 6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxy protecting group; X 7 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or sulfhydryl protecting group; X 8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl or heteroaryl; X 9 is an amino protecting group; X 10 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl alkynyl, aryl or heteroaryl; X 11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, --OX 10 , or --NX 8 X 14 ; X 14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R 1 is hydroxy, protected hydroxy or together with R 14 forms a carbonate; R 2 is hydroxy, or --OCOR 31 ; R 2a is hydrogen; R 4a is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cyano, hydroxy, or --OCOR 30 ; R 5 is hydrogen, R 6 is hydrogen; R 6a is hydrogen; R 7 is hydrogen; R 7a is hydrogen, halogen, or --OR 28 ; R 9 is hydrogen or together with R 9a forms an oxo, R 9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R 9 forms an oxo; R 10 is hydrogen or together with R 10a forms an oxo, R 10a is hydrogen, --OCOR 29 , hydroxy, or protected hydroxy, or together with R 10 forms an oxo; R 14 is hydrogen, hydroxy, protected hydroxy or together with R 1 forms a carbonate; R 14a is hydrogen; R 28 is hydrogen, acyl, or hydroxy protecting group; and R 29 , R 30 , and R 31 are independently hydrogen, alkyl, alkenyl, alkynyl, monocyclic aryl or monocyclic heteroaryl.
Claim 2
Dependent Claim
329 words
A taxane having the formula ##STR27## wherein X 1 is --OX 6 , --SX 7 , or --NX 8 X 9 ; X 2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; X 3 is hydrogen; X 4 is pyridyl; X 5 is --CO 10 , --COOX 10 , --COSX 10 , --CONX 8 X 10 , or --SO 2 X 11 ; X 6 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxy protecting group; X 7 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or sulfhydryl protecting group; X 8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl or heteroaryl; X 9 is an amino protecting group; X 10 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl alkynyl, aryl or heteroaryl; X 11 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, --OX 10 , or --NX 8 X 14 ; X 14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R 1 is hydroxy, protected hydroxy or together with R 14 forms a carbonate; R 2 is hydroxy, or --OCOR 31 ; R 2a is hydrogen; R 4a is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cyano, hydroxy, or --OCOR 30 ; R 5 is hydrogen, R 6 is hydrogen; R 6a is hydrogen; R 7 is hydrogen; R 7a is hydrogen, halogen, or --OR 28 ; R 9 is hydrogen or together with R 9a forms an oxo, R 9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R 9 forms an oxo; R 10 is hydrogen or together with R 10a forms an oxo, R 10a is hydrogen, --OCOR 29 , hydroxy, or protected hydroxy, or together with R 10 forms an oxo; R 14 is hydrogen, hydroxy, protected hydroxy or together with R 1 forms a carbonate; R 14a is hydrogen; R 28 is hydrogen, acyl, or hydroxy protecting group; and R 29 , R 30 , and R 31 are independently hydrogen, alkyl, alkenyl, alkynyl, monocyclic aryl or monocyclic heteroaryl.
Claim 3
Dependent Claim
18 words
The taxane of claim 1 wherein X 5 is --COX 10 and X 10 is heteroaryl or alkoxy.
Claim 4
Dependent Claim
18 words
The taxane of claim 1 wherein X 5 is --COX 10 and X 10 is furyl or thienyl.
Claim 5
Dependent Claim
20 words
The taxane of claim 1 wherein X 5 is --COS 10 and X 10 is ethoxy, t-butoxy, n-butoxy, or i-propoxy.
Claim 6
Dependent Claim
25 words
The taxane of claim 1 wherein X 5 is --COOX 10 , X 10 is alkyl, R 9 is hydrogen and R 9a is hydroxy.
Claim 7
Dependent Claim
37 words
The taxane of claim 1 wherein R 9a is hydrogen, acyloxy or together with R 9 forms an oxo; R 4 is hydrogen, hydroxy, acetoxy or --OCOR 30 ; and R 1 is hydroxy, or protected hydroxy.
Claim 8
Dependent Claim
37 words
The taxane of claim 2 wherein R 9a is hydrogen, acyloxy or together with R 9 forms an oxo; R 4a is hydrogen, hydroxy, acetoxy or --OCOR 30 ; and R 1 is hydroxy, or protected hydroxy.
Claim 9
Dependent Claim
294 words
A taxane having the formula ##STR28## wherein X 1 is --OX 6 ; X 2 is hydrogen; X 3 is hydrogen; X 4 is pyridyl; X 5 is --COX 10 , --COOX 10 , --COSX 10 , --CONX 8 X 10 , or --SO 2 X 11 ; X 6 is hydrogen or hydroxy protecting group; X 8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl or heteroaryl; X 9 is an amino protecting group; X 10 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl alkynyl, aryl or heteroaryl; X 11 is alkyl, alkenyl, alkynyl, heteroaryl, --OX 10 , or --NX 8 X 14 ; X 14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R 1 is hydroxy, protected hydroxy or together with forms a carbonate; R 2 is hydroxy, or --OCOR 31 ; R 2a is hydrogen; R 4a is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cyano, hydroxy, or --OCOR 30 ; R 5 is hydrogen, R 6 is hydrogen; R 6a is hydrogen; R 7 is hydrogen; R 7a is hydrogen, halogen, or --OR 28 ; R 9 is hydrogen or together with R 9a forms an oxo, R 9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R 9 forms an oxo; R 10 is hydrogen or together with R 10a forms an oxo, R 10a is hydrogen, --OCOR 29 , hydroxy, or protected hydroxy, or together with R 10 forms an oxo; R 14 is hydrogen, hydroxy, protected hydroxy or together with R 1 forms a carbonate; R 14a is hydrogen; R 28 is hydrogen, acyl, or hydroxy protecting group; and R 29 , R 30 , and R 31 are independently hydrogen, alkyl, alkenyl, alkynyl, monocyclic aryl or monocyclic heteroaryl.
Claim 10
Dependent Claim
294 words
A taxane having the formula ##STR28## wherein X 1 is --OX 6 ; X 2 is hydrogen; X 3 is hydrogen; X 4 is pyridyl; X 5 is --COX 10 , --COOX 10 , --COSX 10 , --CONX 8 X 10 , or --SO 2 X 11 ; X 6 is hydrogen or hydroxy protecting group; X 8 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl, alkynyl, aryl or heteroaryl; X 9 is an amino protecting group; X 10 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or heterosubstituted alkyl, alkenyl alkynyl, aryl or heteroaryl; X 11 is alkyl, alkenyl, alkynyl, heteroaryl, --OX 10 , or --NX 8 X 14 ; X 14 is hydrogen, alkyl, alkenyl, alkynyl, aryl, or heteroaryl; R 1 is hydroxy, protected hydroxy or together with forms a carbonate; R 2 is hydroxy, or --OCOR 31 ; R 2a is hydrogen; R 4a is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cyano, hydroxy, or --OCOR 30 ; R 5 is hydrogen, R 6 is hydrogen; R 6a is hydrogen; R 7 is hydrogen; R 7a is hydrogen, halogen, or --OR 28 ; R 9 is hydrogen or together with R 9a forms an oxo, R 9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R 9 forms an oxo; R 10 is hydrogen or together with R 10a forms an oxo, R 10a is hydrogen, --OCOR 29 , hydroxy, or protected hydroxy, or together with R 10 forms an oxo; R 14 is hydrogen, hydroxy, protected hydroxy or together with R 1 forms a carbonate; R 14a is hydrogen; R 28 is hydrogen, acyl, or hydroxy protecting group; and R 29 , R 30 , and R 31 are independently hydrogen, alkyl, alkenyl, alkynyl, monocyclic aryl or monocyclic heteroaryl.
Claim 11
Dependent Claim
47 words
The taxane of claim 8 wherein X 5 is --COX 10 and X 10 is furyl, thienyl, alkyl substituted furyl or thienyl, tert-, iso- or n-butoxy, ethoxy, iso- or n-propoxy, cyclohexyloxy, allyloxy, crotyloxy, 1,3-diethoxy-2-propoxy, 2-methoxyethoxy, amyloxy, neopentyloxy, PhCH 2 O--, --NPh 2 , --NHnPr, --NHPh, or --NHEt.
Claim 12
Dependent Claim
23 words
A pharmaceutical composition which contains the taxane of claim 1 and one or more pharmacologically acceptable, inert or physiologically active diluents or adjuvants.
Claim 13
Dependent Claim
88 words
A taxane having the formula ##STR29## wherein X 1 , R 1 and R 7 are hydroxy; X 3 is pyridyl; X 5 is --COX 10 ; X 10 is butoxy or phenyl; R 2 is benzoyloxy; R 4a is acetoxy; R 6 is hydrogen; R 6a is hydrogen; R 10a together with R 9a form an oxo; R 10a is acetoxy; and X 2 , X 4 , R 2a , R 5 , R 7a , R 10 , R 14 and R 14a are hydrogen.
Claim 14
Dependent Claim
88 words
A taxane having the formula ##STR29## wherein X 1 , R 1 and R 7 are hydroxy; X 3 is pyridyl; X 5 is --COX 10 ; X 10 is butoxy or phenyl; R 2 is benzoyloxy; R 4a is acetoxy; R 6 is hydrogen; R 6a is hydrogen; R 10a together with R 9a form an oxo; R 10a is acetoxy; and X 2 , X 4 , R 2a , R 5 , R 7a , R 10 , R 14 and R 14a are hydrogen.
Claim 15
Dependent Claim
10 words
The taxane of claim 11 wherein X 10 is t-butoxy.
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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) | 1999-02-05 | 1999-08-07 | 2000-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-02-05 | 2003-08-07 | 2004-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-02-05 | 2007-08-07 | 2008-02-06 | $7700.00 | Window Closed / Lapsed |