Taxol derivatives
AssigneeBristol-Myers Squibb Company
InventorsShu-Hui Chen, Vittorio Farina
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Abstract
The present invention relates to 10-desacetoxy-11,12-dihydrotaxol-10,12(18)-diene derivatives which are useful as antitumor agents and as intermediates for the preparation of 10-desacetoxytaxol. Also disclosed is a novel process for the preparation of 10-desacetoxytaxol which comprises treating hydroxy protected 10-deacetyltaxol with 1,1,2-trifluoro-2-chlorotriethylamine followed by catalytic hydrogenation.
Claims7
A compound of the formula ##STR25## wherein R.sup.2 is hydrogen and R.sup.3 is hydroxy;
- or R.sup.3 is hydrogen and R.sup.2 is hydroxy, chlorofluoroacetoxy, or a protected hydroxy group;
- R.sup.4 is hydrogen or a hydroxy protecting group;
- and the dash bonds together represent 10,12-diene or 11-ene;
- with the proviso that when R.sup.3 is hydroxy and R.sup.2 is hydrogen, or when R.sup.3 is hydrogen and R.sup.2 is hydroxy or a protected hydroxy group, the dash bonds together represent 10,12-diene.
A compound selected from the group consisting of 2'-O-allyloxycarbonyl-7-O-chlorofluoroacetyl-10-desacetoxy-11,12-dihydrota xol-10,12(18)-diene;
- 7-O-chlorofluoroacetyl-10-desacetoxy-11,12(18)-dihydrotaxol-10,12(18)-dien e;
- 7-O-chlorofluoroacetyl-10-desacetoxytaxol;
- and 2'-O-benzyloxycarbonyl-7-chlorofluoroacetyl-10-desacetoxy-11,12-dihydrotax ol-10,12(18)-diene.
A compound selected from the group consisting of 2',7-bis-O-(2,2,2-trichloroethoxycarbonyl)-10-desacetoxy-11,12-dihydrotaxo l-10,12(18)-diene;
- 10-desacetoxy-11,12-dihydrotaxol-10,12(18)-diene;
- 2'-O-benzyloxycarbonyl-10-desacetoxy-11,12-dihydrotaxol-10,12(18)-diene;
- 2'-O-allyloxycarbonyl-10-desacetoxy-11,12-dihydro-7-epitaxol-10,12(18)-die ne;
- and 10-desacetoxy-11,12-dihydro-7-epitaxol-10,12(18)-diene.
Dependencies are inferred from the claim text.