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Details for Patent: 6,040,466

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Details for Patent: 6,040,466

Title: Taxoids, their preparation and pharmaceutical compositions containing them
Abstract:New taxoids and methods of preparing new taxoids of general formula (I): ##STR1## in which: R.sub.4 represents an alkanoyloxy radical in which the alkanoyl portion contains 2 to 6 carbon atoms in an unbranched or branched chain, this radical unsubstituted or substituted with one or more halogen atoms, an alkoxy radical containing 1 to 4 carbon atoms, or alternatively R.sub.4 represents a cycloalkanoyloxy radical in which the cycloalkanoyl portion contains 4 to 8 carbon atoms, or alternatively R.sub.4 represents a benzoyloxy radical; R.sub.5 represents an alkoxy radical containing 1 to 4 carbon atoms, substituted by an alkylthio radical containing 1 to 4 carbon atoms; and Z represents a hydrogen atom or a radical of general formula: ##STR2## wherein such new taxoids display noteworthy anti-tumor and anti-leukemic properties.
Inventor(s): Bouchard; Herve (Thiais, FR), Bourzat; Jean-Dominique (Vincennes, FR), Commer.cedilla.on; Alain (Vitry-sur-Seine, FR)
Assignee: Rhone Poulenc Rorer SA (Antony, FR)
Filing Date:Mar 17, 1999
Application Number:09/271,300
Claims:1. A taxoid of general formula: ##STR30## in which: Z represents a hydrogen atom or a radical of general formula: ##STR31## in which: R.sub.1 represents a benzoyl radical unsubstituted or substituted with one or more identical or different atoms or radicals selected from halogen atoms, and alkyl radicals containing 1 to 4 carbon atoms, alkoxy radicals containing 1 to 4 carbon atoms or trifluoromethyl radicals, a thenoyl radical, a furoyl radical, and a radical R.sub.2 --O--C(.dbd.O)-- in which

R.sub.2 represents an alkyl radical containing 1 to 8 carbon atoms, an alkenyl radical containing 2 to 8 carbon atoms, an alkynyl radical containing 3 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, a cycloalkenyl radical containing 4 to 6 carbon atoms, a phenyl radical, which is unsubstituted or substituted with one or more atoms or radicals selected from halogen atoms, alkyl radicals containing 1 to 4 carbon atoms, and alkoxy radicals containing 1 to 4 carbon atoms, cyano radicals, carboxyl radicals, and alkoxycarbonyl radicals in which the alkyl portion contains 1 to 4 carbon atoms;

a phenyl or an .alpha.- or .beta.-naphthyl radical, which is unsubstituted or substituted with one or more atoms or radicals selected from halogen atoms, alkyl radicals containing 1 to 4 carbon atoms, alkoxy radicals containing 1 to 4 carbon atoms, and a 5-membered aromatic heterocyclic radical;

R.sub.3 represents a phenyl radical;

R.sub.4 represents an alkanoyloxy radical in which the alkanoyl portion contains 2 to 6 carbon atoms in an unbranched or branched chain, this radical unsubstituted or substituted with one or more halogen atoms, or with an alkoxy radical containing 1 to 4 carbon atoms, or alternatively, R.sub.4 represents a cycloalkanoyloxy radical in which the cycloalkanoyl portion contains 4 to 8 carbon atoms, or alternatively, R.sub.4 represents a benzoyloxy radical;

R.sub.5 represents an alkoxy radical containing 1 to 4 carbon atoms in an unbranched or branched chain, substituted by an alkylthio radical containing 1 to 4 carbon atoms.

2. The taxoid of claim 1 in which R.sub.4 represents an alkanoyloxy radical in which the alkanoyl portion contains 2 to 6 carbon atoms, or a cycloalkanoyloxy radical in which the cycloalkanoyl portion contains 4 to 8 carbon atoms.

3. A taxoid according to claim 1 for which Z represents a hydrogen atom or a radical of general formula (II) in which

R.sub.1 represents a benzoyl radical or a radical R.sub.2 --O--C(.dbd.O)-- in which R.sub.2 represents a tert-butyl radical;

R.sub.3 represents a phenyl radical;

R.sub.4 represents an alkanoyloxy radical in which the alkanoyl portion contains 2 to 4 carbon atoms; and

R.sub.5 represents an alkoxy radical containing 1 to 4 carbon atoms substituted by a methylthio radical.

4. A taxoid according to claim 1 for which Z represents a hydrogen atom or a radical of general formula (II) in which R.sub.1 represents a benzoyl radical or a radical R.sub.2 --O--C(.dbd.O)-- in which

R.sub.2 represents a tert-butyl radical;

R.sub.3 represents a phenyl radical;

R.sub.4 represents an acetoxy or methoxyacetoxy radical; and

R.sub.5 represents a methylthiomethoxy radical.

5. The taxoid of claim 4, wherein R.sub.4 is acetoxy.

6. The taxoid 4.alpha.-acetoxy-2.alpha.-benzoyloxy-5.beta.,20-epoxy-1.beta.-hydroxy-7.be ta.-methylthiomethoxy-9-oxo-10.beta.-methoxyacetoxy-11-taxen-13.alpha.-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate.

7. The taxoid 4.alpha.-acetoxy-2.alpha.-benzoyloxy-5.beta.,20-epoxy-1.beta.-hydroxy-7.be ta.-methylthiomethoxy-9-oxo-10.beta.-acetoxy-11-taxen-13.alpha.-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate.

8. A pharmaceutical composition, comprising at least one taxoid according to claim 1, in which Z represents a radical of general formula (II), and one or more pharmaceutically acceptable carriers.

9. A pharmaceutical composition, comprising the taxoid of claim 6 or claim 7 in combination with one or more pharmaceutically acceptable carriers.

10. The pharmaceutical composition of claim 6 or claim 7, wherein the pharmaceutically acceptable carrier is a diluent or adjuvant.

11. The pharmaceutical composition of claim 9, further comprising another pharmacologically active compound.

12. The pharmaceutical composition of claim 10, further comprising another pharmacologically active compound.
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