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US 6,080,739 AGranted
Colchicine-skeleton compounds, their use as medicaments and compositions containing them
AssigneeIndena S.p.A.
InventorEzio Bombardelli
Life of this patent
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Abstract
The present invention relates to colchicine and thiocolchicine derivatives which can be obtained from these molecules by functionalization of the C-7 to ketone or functionalization of the amino group. Said compounds have a marked antiblastic activity both on the normal cancer cells and on the chemoresistant phenotype. The compounds of the invention can be administered both by injection and orally.
Claims13
A compound of formula I:
- ##STR3## wherein R is methoxy or methylthio;
- and R.sub.1 is a straight chain or branched alkyl group having 1 to 6 carbon atoms, a straight chain or branched alkenyl group having 1 to 6 carbon atoms, a cyclic aliphatic moiety, a heterocyclic moiety, a saturated or unsaturated monocarboxylic acyl residue, a saturated or unsaturated dicarboxylic acyl residue, a saturated or unsaturated amino acid acyl residue, a .beta.-D-glucose residue, or a 6-deoxylgalactose residue, with the proviso that, when R is methoxy, R.sub.1 is other than methyl or acetyl.
The compound of formula II:
- ##STR4## wherein R is methoxy or methylthio;
- and R.sub.1 is a straight chain or branched alkyl group having 1 to 6 carbon atoms, a straight chain or branched alkenyl group having 1 to 6 carbon atoms, a cyclic aliphatic moiety, a heterocyclic moiety, a saturated or unsaturated monocarboxylic acyl residue, a saturated or unsaturated dicarboxylic acyl residue, a saturated or unsaturated amino acid acyl residue, a .beta.-D-glucose residue, or a 6-deoxylgalactose residue.
A method of preparing a compound of formula I:
- ##STR5## wherein R is methoxy or methylthio;
- and R.sub.1 is a straight chain or branched alkyl group having 1 to 6 carbon atoms, a straight chain or branched alkenyl group having 1 to 6 carbon atoms, a cyclic aliphatic moiety, a heterocyclic moiety, a saturated or unsaturated monocarboxylic acyl residue, a saturated or unsaturated dicarboxylic acyl residue, a saturated or unsaturated amino acid acyl residue, a .beta.-D-glucose residue, or a 6-deoxylgalactose residue, with the proviso that, when R is methoxy, R.sub.1 is other than methyl or acetyl;
- comprising:
- selecting a first compound from the group consisting of N-deacetylcolchicine and N-deacetylthiocolchicine;
- and
- reacting said first compound with 4-formyl-1-methylpyridinium p-toluenesulfonate and 1,8-diazabicyclo[5.4.0]undec-7-ene at a temperature and for a time sufficient to form the compound of formula I.
3 more elements
A method of preparing a compound of formula II:
- ##STR6## wherein R is methoxy or methylthio;
- and R.sub.1 is a straight chain or branched alkyl group having 1 to 6 carbon atoms, a straight chain or branched alkenyl group having 1 to 6 carbon atoms, a cyclic aliphatic moiety, a heterocyclic moiety, a saturated or unsaturated monocarboxylic acyl residue, a saturated or unsaturated dicarboxylic acyl residue, a saturated or unsaturated amino acid acyl residue, a .beta.-D-glucose residue, or a 6-deoxylgalactose residue;
- comprising:
- selecting a first compound from the group consisting of N-deacetylcolchicine and N-deacetylthiocolchicine;
- and
- reacting said first compound with 3,5-ditert-buty-1,2-benzoquinone at a temperature and for a time sufficient to form the compound of formula II.
3 more elements
Dependencies are inferred from the claim text.