US5227400A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Furyl and thienyl substituted taxanes and pharmaceutical compositions containing them
Assignee: Florida State University
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Filing: 1992-04-03
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Granted: 1993-07-13
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Expires: 2012-04-03
Abstract
Abstract A taxane derivative of the formula ##STR1## wherein ##STR2## Z is --OT 1 , T 1 is hydrogen, hydroxyl protecting group, or --COT 2 , T 2 is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkynyl or monocylic aryl, R 3 is benzoyl, substituted benzoyl or C 1 -C 6 alkoxycarbonyl, Ac is acetyl, and E 1 and E 2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.
Inventors
- 👤 Robert A. Holton
- 👤 Hossain Nadizadeh
- 👤 Ronald J. Beidiger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 09:19
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; A; A61; A61P; A61P35/00; C07D305/00; C07D305/14; C07D409/00; C07D409/02; C07D409/12; C07F; C07F7/00; C07F7/003; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
276 words
A taxane derivative of the formula ##STR22## wherein ##STR23## Z is --OT 1 , T 1 is hydrogen, hydroxyl protecting group, or --COT 2 , T 2 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or monocylic aryl, R 3 is benzoyl, substituted benzoyl or C 1 -C 6 alkoxycarbonyl wherein the substitution is on the para-position of the benzoyl group and the substituent is selected from the group consisting of Cl, Br, F, NO 2 -- and CH 3 O--, Ac is acetyl, E 1 and E 2 are independently hydrogen or --COGCOR 1 G is ethylene, propylene, CH═CH, 1,2-cyclohexane, or 1,2-phenylene, R 1 =OH base, NR 2 R 3 , OR 3 , SR 3 , OCH 2 CONR 4 R 5 , OH R 2 =hydrogen, methyl R 3 =(CH 2 ) n NR 6 R 7 ; (CH 2 ) n N.sup.⊕ R 6 R 7 R 8 X.sup.⊖ n=1 to 3 R 4 =hydrogen, lower alkyl containing 1 to 4 carbons R 5 =hydrogen, lower alkyl containing 1 to 4 carbons, benzyl, hydroxyethyl, CH 2 CO 2 H, dimethylaminoethyl R 6 R 7 =lower alkyl containing 1 to 2 carbons, benzyl or R 6 and R 7 together with the nitrogen atom of NR 6 R 7 form the following rings ##STR24## R 8 =lower alkyl containing 1 to 2 carbons, benzyl X.sup.⊖ =halide and base=NH 3 , (HOC 2 H 4 ) 3 N, N(CH 3 ) 3 , CH 3 N(C 2 H 4 OH) 2 , NH 2 (CH 2 ) 6 NH 2 , N-methylglucamine, NaOH, or KOH.
Claim 2
Dependent Claim
276 words
A taxane derivative of the formula ##STR22## wherein ##STR23## Z is --OT 1 , T 1 is hydrogen, hydroxyl protecting group, or --COT 2 , T 2 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or monocylic aryl, R 3 is benzoyl, substituted benzoyl or C 1 -C 6 alkoxycarbonyl wherein the substitution is on the para-position of the benzoyl group and the substituent is selected from the group consisting of Cl, Br, F, NO 2 -- and CH 3 O--, Ac is acetyl, E 1 and E 2 are independently hydrogen or --COGCOR 1 G is ethylene, propylene, CH═CH, 1,2-cyclohexane, or 1,2-phenylene, R 1 =OH base, NR 2 R 3 , OR 3 , SR 3 , OCH 2 CONR 4 R 5 , OH R 2 =hydrogen, methyl R 3 =(CH 2 ) n NR 6 R 7 ; (CH 2 ) n N.sup.⊕ R 6 R 7 R 8 X.sup.⊖ n=1 to 3 R 4 =hydrogen, lower alkyl containing 1 to 4 carbons R 5 =hydrogen, lower alkyl containing 1 to 4 carbons, benzyl, hydroxyethyl, CH 2 CO 2 H, dimethylaminoethyl R 6 R 7 =lower alkyl containing 1 to 2 carbons, benzyl or R 6 and R 7 together with the nitrogen atom of NR 6 R 7 form the following rings ##STR24## R 8 =lower alkyl containing 1 to 2 carbons, benzyl X.sup.⊖ =halide and base=NH 3 , (HOC 2 H 4 ) 3 N, N(CH 3 ) 3 , CH 3 N(C 2 H 4 OH) 2 , NH 2 (CH 2 ) 6 NH 2 , N-methylglucamine, NaOH, or KOH.
Claim 3
Dependent Claim
101 words
A taxane derivative of the formula ##STR25## wherein ##STR26## Z is --OT 1 , T 1 is hydrogen, hydroxyl protecting group, or --COT 2 , T 2 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or monocylic aryl, R 3 is benzoyl, substituted benzoyl or C 1 -C 6 alkoxycarbonyl wherein the substitution is on the para-position of the benzoyl group and the substituent is selected from the group consisting of Cl, Br, F, NO 2 -- and CH 3 O--, Ac is acetyl, and E 1 and E 2 are hydrogen.
Claim 4
Dependent Claim
101 words
A taxane derivative of the formula ##STR25## wherein ##STR26## Z is --OT 1 , T 1 is hydrogen, hydroxyl protecting group, or --COT 2 , T 2 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or monocylic aryl, R 3 is benzoyl, substituted benzoyl or C 1 -C 6 alkoxycarbonyl wherein the substitution is on the para-position of the benzoyl group and the substituent is selected from the group consisting of Cl, Br, F, NO 2 -- and CH 3 O--, Ac is acetyl, and E 1 and E 2 are hydrogen.
Claim 5
Dependent Claim
10 words
The taxane of claim 2 wherein R 1 is ##STR27##
Claim 6
Dependent Claim
18 words
The taxane of claim 2 wherein R 1 is ##STR28## and the taxane has the 2'R, 3'S configuration.
Claim 7
Dependent Claim
10 words
The taxane of claim 2 wherein R 1 is ##STR29##
Claim 8
Dependent Claim
18 words
The taxane of claim 2 wherein R 1 is ##STR30## and the taxane has the 2'R, 3'S configuration.
Claim 9
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 10
Dependent Claim
10 words
The composition of claim 7 wherein R 1 is ##STR31##
Claim 11
Dependent Claim
18 words
The composition of claim 7 wherein R 1 is ##STR32## and the taxane has the 2'R, 3'S configuration.
Claim 12
Dependent Claim
10 words
The composition of claim 7 wherein R 1 is ##STR33##
Claim 13
Dependent Claim
18 words
The composition of claim 7 wherein R 1 is ##STR34## and the taxane has the 2'R, 3'S configuration.
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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) | 1996-07-12 | 1997-01-11 | 1997-07-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-07-12 | 2001-01-11 | 2001-07-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-07-12 | 2005-01-11 | 2005-07-13 | $7700.00 | Window Closed / Lapsed |