Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
First Claim
1. A taxane derivative of the formula ##STR16## wherein R1 is phenyl or p-nitrophenyl,R3 is furyl or thienyl,T1 is hydrogen, hydroxyl protecting group, or --COT2,T2 is H, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl or monocylic aryl,Ac is acetyl, andE1 and E2 are independently selected from hydrogen and hydroxyl protecting groups.
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Abstract
Taxane derivatives of the formula ##STR1## wherein R1 is phenyl or p-nitrophenyl,
R3 is furyl or thienyl,
T1 is hydrogen, hydroxyl protecting group, or --COT2,
T2 is H, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl or monocylic aryl,
Ac is acetyl, and
E1 and E2 are independently selected from hydrogen and functional groups which increase the water solubility of the taxane derivative are useful as antitumor agents.
169 Citations
6 Claims
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1. A taxane derivative of the formula ##STR16## wherein R1 is phenyl or p-nitrophenyl,
R3 is furyl or thienyl, T1 is hydrogen, hydroxyl protecting group, or --COT2, T2 is H, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl or monocylic aryl, Ac is acetyl, and E1 and E2 are independently selected from hydrogen and hydroxyl protecting groups.
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2. A taxane derivative of the formula ##STR17## wherein R1 is phenyl or p-nitrophenyl,
R3 is furyl or thienyl, T1 is hydrogen, hydroxyl protecting group, or --COT2, T2 is H, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl or monocylic aryl, Ac is acetyl, and E1 and E2 are independently selected from hydrogen, and --COGCOR1 wherein G is ethylene, propylene, CH═ - CH, 1,2-cyclohexane, or 1,2-phenylene,
R1 =OH base, NR2 R3, OR3, SR3, OCH2 CONR4 R5, OH R2 =hydrogen, methyl R3 =(CH2)n NR6 R7 ;
(CH2)n N.sup.⊕
R6 R7 R8 X.sup.⊖n=1 to 3 R4 =hydrogen, lower alkyl containing 1 to 4 carbons R5 =hydrogen, lower alkyl containing 1 to 4 carbons, benzyl, hydroxyethyl, CH2 CO2 H, dimethylaminoethyl R6 R7 =lower alkyl containing 1 or 2 carbons, benzyl or R6 and R7 together with the nitrogen atom of NR6 R7 form the following rings ##STR18## R8 =lower alkyl containing 1 or 2 carbons, benzyl X.sup.⊖
=halidebase=NH3, (HOC2 H4)3 N, N(CH3)3, CH3 N(C2 H4 OH)2, NH2 (CH2)6 NH2, N-methylglucamine, NaOH, KOH.
- CH, 1,2-cyclohexane, or 1,2-phenylene,
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5. A taxane derivative of the formula ##STR19## wherein Ph is phenyl, and
Ac is acetyl.
Specification
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- Resources
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Current AssigneeFlorida State University (State University System of Florida)
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Original AssigneeFlorida State University (State University System of Florida)
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InventorsRengan, Kasthuri, Holton, Robert A., Nadizadeh, Hossain
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Primary Examiner(s)Ivy, C. Warren
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Assistant Examiner(s)Trinh, Ba K.
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Application NumberUS07/975,723Time in Patent Office445 DaysField of Search549/510, 549/511, 549/60, 549/473, 549/214, 544/60, 544/147, 544/375, 546/196, 546/207, 548/525, 514/444, 514/449, 514/471US Class Current514/444CPC Class CodesA61P 35/00 Antineoplastic agentsA61P 35/02 specific for leukemiaC07C 227/22 from lactams, cyclic ketone...C07C 231/12 by reactions not involving ...C07C 233/87 of a carbon skeleton contai...C07C 2601/14 The ring being saturatedC07C 2601/16 the ring being unsaturatedC07C 2603/62 containing three- or four-m...C07D 305/14 condensed with carbocyclic ...C07D 407/12 linked by a chain containin...C07D 409/12 linked by a chain containin...C07F 7/1804 Compounds having Si-O-C lin...Y02P 20/55 Design of synthesis routes,...
