Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
AssigneeFlorida State University
InventorsRobert A. Holton, Kasthuri Rengan, Hossain Nadizadeh
Life of this patent
Estimating the term…
Abstract
Taxane derivatives of the formula ##STR1## wherein R.sub.1 is phenyl or p-nitrophenyl, R.sub.3 is furyl or thienyl, T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2, T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or monocylic aryl, Ac is acetyl, and E.sub.1 and E.sub.2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.
Claims6
A taxane derivative of the formula ##STR16## wherein R.sub.1 is phenyl or p-nitrophenyl,
- R.sub.3 is furyl or thienyl,
- T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2,
- T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or monocylic aryl,
- Ac is acetyl, and
- E.sub.1 and E.sub.2 are independently selected from hydrogen and hydroxyl protecting groups.
A taxane derivative of the formula ##STR17## wherein R.sub.1 is phenyl or p-nitrophenyl,
- R.sub.3 is furyl or thienyl,
- T.sub.1 is hydrogen, hydroxyl protecting group, or --COT.sub.2,
- T.sub.2 is H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or monocylic aryl,
- Ac is acetyl, and
- E.sub.1 and E.sub.2 are independently selected from hydrogen, and --COGCOR.sup.1 wherein
- G is ethylene, propylene, CH.dbd.CH, 1,2-cyclohexane, or 1,2-phenylene,
- R.sup.1 =OH base, NR.sup.2 R.sup.3, OR.sup.3, SR.sup.3, OCH.sub.2 CONR.sup.4 R.sup.5, OH
- R.sup.2 =hydrogen, methyl
- R.sup.3 =(CH.sub.2).sub.n NR.sup.6 R.sup.7 ;
- (CH.sub.2).sub.n N.sup..sym. R.sup.6 R.sup.7 R.sup.8 X.sup..crclbar.
- n=1 to 3
- R.sup.4 =hydrogen, lower alkyl containing 1 to 4 carbons
- R.sup.5 =hydrogen, lower alkyl containing 1 to 4 carbons, benzyl, hydroxyethyl, CH.sub.2 CO.sub.2 H, dimethylaminoethyl
- R.sup.6 R.sup.7 =lower alkyl containing 1 or 2 carbons, benzyl or R.sup.6 and
- R.sup.7 together with the nitrogen atom of NR.sup.6 R.sup.7 form the following rings ##STR18## R.sup.8 =lower alkyl containing 1 or 2 carbons, benzyl X.sup..crclbar. =halide
- base=NH.sub.3, (HOC.sub.2 H.sub.4).sub.3 N, N(CH.sub.3).sub.3, CH.sub.3 N(C.sub.2 H.sub.4 OH).sub.2, NH.sub.2 (CH.sub.2).sub.6 NH.sub.2, N-methylglucamine, NaOH, KOH.
A taxane derivative of the formula ##STR19## wherein Ph is phenyl, and
- Ac is acetyl.
Dependencies are inferred from the claim text.