Process for the preparation of taxane derivatives, new derivativ

Details Process for the preparation of taxane derivatives, new derivativ Process for the preparation of taxane derivatives, new derivativ

1995-05-23

1997-02-25

Trinh, Ba K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549511, C07D30514

Patent

active

056060831

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION OF THE INVENTION

This application is a 371 of PCT/FR93/01145, dated Nov. 22, 1993.
The present invention relates to the preparation of taxane derivatives of general formula: ##STR2## to the new products thus obtained and to the pharmaceutical compositions which contain them.
In the general formula (I), R represents a hydrogen atom or an acetyl radical, R.sub.1 represents a benzoyl radical or a radical R.sup.2 --O--CO-- in which R.sub.2 represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, phenyl or heterocyclyl radical, and Het represents an optionally substituted aromatic heterocyclyl radical having 5 members and containing one or a number of heteroatoms, which are identical or different, chosen from nitrogen, oxygen and sulphur.
More particularly, the present invention relates to the preparation of the products of general formula (I) in which: benzoyl radical or a radical R.sub.2 --O--CO in which R.sup.2 represents: 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 or a bicycloalkyl radical containing 7 to 10 carbon atoms, these radicals optionally being substituted by one or a number of substituents, which are identical or different, chosen from the halogen atoms and the hydroxyl radical, alkoxy radical containing 1 to 4 carbon atoms, dialkylamino radical, each alkyl part of which contains 1 to 4 carbon atoms, piperidino radical, morpholino radical, 1-piperazinyl radical (optionally substituted in the 4-position by an alkyl radical containing 1 to 4 carbon atoms or by a phenylalkyl radical, the alkyl part of which contains 1 to 4 carbon atoms), cycloalkyl radical containing 3 to 6 carbon atoms, cycloalkenyl radical containing 4 to 6 carbon atoms, phenyl radical, cyano radical, nitro radical, carboxyl radical or alkoxycarbonyl radical, the alkyl part of which contains 1 to 4 carbon atoms, which are identical or different, chosen from the alkyl radicals containing 1 to 4 carbon atoms or the alkoxy radicals containing 1 to 4 carbon atoms, containing 5 or 6 members, optionally substituted by one or a number of alkyl radicals containing 1 to 4 carbon atoms, it being understood that the cycloalkyl, cycloalkenyl or bicycloalkyl radicals may optionally be substituted by one or a number of alkyl radicals containing 1 to 4 carbon atoms, and containing one or a number of atoms, which are identical or different, chosen from the nitrogen, oxygen or sulphur atoms, such as thiophene, thiazole, furan, pyrrole, imidazole, isoxazole or pyrazole, optionally substituted by one or a number of substituents, which are identical or different, chosen from the halogen atoms (fluorine, chlorine) and the alkyl, containing 1 to 4 carbon atoms, aryl, containing 6 to 10 carbon atoms, alkoxy, containing 1 to 4 carbon atoms, aryloxy, containing 6 to 10 carbon atoms, amino, alkylamino, containing 1 to 4 carbon atoms, dialkylamino, each alkyl part of which contains 1 to 4 carbon atoms, acylamino, the acyl part of which contains 1 to 4 carbon atoms, alkoxycarbonylamino, containing 1 to 4 carbon atoms, acyl, containing 1 to 4 carbon atoms, arylcarbonyl, the aryl part of which contains 6 to 10 carbon atoms, cyano, nitro, hydroxyl, carboxyl, carbamoyl, alkylcarbamoyl, the alkyl part of which contains 1 to 4 carbon atoms, dialkylcarbamoyl, each alkyl part of which contains 1 to 4 carbon atoms, or alkoxycarbonyl, the alkoxy part of which contains 1 to 4 carbon atoms, radicals.
The preparation of the products of general formula (I) in which R represents a hydrogen atom or an acetyl radical, R.sub.1 represents a benzoyl radical or a radical R.sub.2 --O--CO-- in which R.sup.2 represents a t-butyl radical and Het represents a 2- or 3-thienyl or 2- or 3-furyl radical is very particularly advantageous.
According to the present invention, the derivatives of general formula (I) can be obtained from a product of general formula: ##STR3## in which Het and R.sub.1

REFERENCES:
patent: 4814470 (1989-03-01), Colin et al.
patent: 5229526 (1993-07-01), Holton
Commergan et al, "Tetrahedron Letters", 33(36), pp. 5185-5188, 1992.

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