US5283253A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
Assignee: Florida State University
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Filing: 1992-11-13
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Granted: 1994-02-01
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Expires: 2012-11-13
Abstract
Abstract Taxane derivatives of the formula ##STR1## wherein R 1 is phenyl or p-nitrophenyl, R 3 is furyl or thienyl, 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, 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
- 👤 Kasthuri Rengan
- 👤 Hossain Nadizadeh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 04:47
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; A; A61; A61P; A61P35/00; A61P35/02; C07C; C07C227/00; C07C227/22; C07C231/00; C07C231/12; C07C233/00; C07C233/64; C07C233/81; C07C233/82; C07C233/87; C07D305/00; C07D305/14; C07D409/00; C07D409/02; C07D409/12; C07F; C07F7/00; 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; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
71 words
A taxane derivative of the formula ##STR16## wherein R 1 is phenyl or p-nitrophenyl, R 3 is furyl or thienyl, 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, Ac is acetyl, and E 1 and E 2 are independently selected from hydrogen and hydroxyl protecting groups.
Claim 2
Dependent Claim
71 words
A taxane derivative of the formula ##STR16## wherein R 1 is phenyl or p-nitrophenyl, R 3 is furyl or thienyl, 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, Ac is acetyl, and E 1 and E 2 are independently selected from hydrogen and hydroxyl protecting groups.
Claim 3
Dependent Claim
241 words
A taxane derivative of the formula ##STR17## wherein R 1 is phenyl or p-nitrophenyl, R 3 is furyl or thienyl, 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, Ac is acetyl, and E 1 and E 2 are independently selected from hydrogen, and --COGCOR 1 wherein 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 or 2 carbons, benzyl or R 6 and R 7 together with the nitrogen atom of NR 6 R 7 form the following rings ##STR18## R 8 =lower alkyl containing 1 or 2 carbons, benzyl X.sup.⊖ =halide 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, KOH.
Claim 4
Dependent Claim
241 words
A taxane derivative of the formula ##STR17## wherein R 1 is phenyl or p-nitrophenyl, R 3 is furyl or thienyl, 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, Ac is acetyl, and E 1 and E 2 are independently selected from hydrogen, and --COGCOR 1 wherein 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 or 2 carbons, benzyl or R 6 and R 7 together with the nitrogen atom of NR 6 R 7 form the following rings ##STR18## R 8 =lower alkyl containing 1 or 2 carbons, benzyl X.sup.⊖ =halide 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, KOH.
Claim 5
Dependent Claim
21 words
The taxane derivative of claim 1 wherein T 1 is --COCH 3 , and E 1 and E 2 are hydrogen.
Claim 6
Dependent Claim
15 words
The taxane derivative of claim 1 wherein the taxane derivative has the 2'R, 3'S configuration.
Claim 7
Dependent Claim
15 words
A taxane derivative of the formula ##STR19## wherein Ph is phenyl, and Ac is acetyl.
Claim 8
Dependent Claim
15 words
A taxane derivative of the formula ##STR19## wherein Ph is phenyl, and Ac is acetyl.
Claim 9
Dependent Claim
24 words
A pharmaceutical composition which contains the taxane derivative of claim 1 and one or more pharmacologically acceptable, inert or physiologically active diluents or adjuvants.
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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) | 1997-01-31 | 1997-08-02 | 1998-02-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-01-31 | 2001-08-02 | 2002-02-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-01-31 | 2005-08-02 | 2006-02-01 | $7700.00 | Window Closed / Lapsed |