Method for preparing taxane derivatives

Details Method for preparing taxane derivatives Method for preparing taxane derivatives

1995-04-28

1997-11-11

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544172, 544369, 544209, C07D41312, C07D30514, C07D26304

Patent

active

056866232

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/FR93/01058 filed Oct. 28, 1993.


DESCRIPTION OF THE INVENTION

The present invention relates to a process for the preparation of taxane derivatives of general formula: ##STR2## which are particularly advantageous intermediates for preparing taxol, Taxotere and their analogues which have notable antileukaemic and antitumour properties.
In the general formula (I), 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 11 carbon atoms, these radicals optionally being substituted by one or a number of substituents 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 cyano radical, carboxyl radical or alkoxycarbonyl radical, the alkyl part of which contains 1 to 4 carbon atoms, radicals chosen from the halogen atoms and the alkyl radicals containing 1 to 4 carbon atoms or the alkoxy radicals containing 1 to 4 carbon atoms, containing 4 to 6 members and 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, atom or an alkyl, phenylalkyl, phenyl, alkoxyphenyl or dialkoxyphenyl radical or else R.sub.1 and R.sub.2 form, together with the carbon atom to which they are bonded, a ring having from 4 to 7 members, functional group and
More particularly, Ar represents a phenyl or .alpha.- or .beta.-naphthyl radical optionally substituted by one or a number of atoms or radicals, identical or different, chosen from the halogen atoms (fluorine, chlorine, bromine, iodine) and the alkyl, alkenyl, alkynyl, aryl, aralkyl, alkoxy, alkylthio, aryloxy, arylthio, hydroxyl, hydroxyalkyl, mercapto, formyl, acyl, acylamino, aroylamino, alkoxycarbonylamino, amino, alkylamino, dialkylamino, carboxyl, alkoxycarbonyl, carbamoyl, dialkylcarbamoyl, cyano, nitro and trifluoromethyl radicals, it being understood that the alkyl radicals and the alkyl portions of the other radicals contain 1 to 4 carbon atoms, that the alkenyl and alkynyl radicals contain 3 to 8 carbon atoms and that the aryl radicals are phenyl or .alpha.- or .beta.-naphthyl radicals, or else Ar represents an aromatic heterocyclic radical having 5 members and containing one or a number of atoms, identical or different, chosen from the nitrogen, oxygen or sulphur atoms, optionally substituted by one or a number of substituents, identical or different, chosen from the halogen atoms (fluorine, chlorine, bromine, iodine) and the alkyl radicals containing 1 to 4 carbon atoms, aryl radicals containing 6 to 10 carbon atoms, alkoxy radical containing 1 to 4 carbon atoms, aryloxy radical containing 6 to 10 carbon atoms, amino radical, alkylamino radical containing 1 to 4 carbon atoms, dialkylamino radical, in which each alkyl part contains 1 to 4 carbon atoms, acylamino radical, the acyl part of which contains 1 to 4 carbon atoms, alkoxycarbonylamino radical containing 1 to 4 carbon atoms, acyl radical containing 1 to 4 carbon atoms, arylcarbonyl, the aryl part of which contains 6 to 10 carbon atoms, cyano radical, carboxyl radical, carbamoyl radical, alkylcarbamoyl radical, the alkyl part of which contains 1 to 4 carbon atoms, dialkylcarbamoyl radical, each alkyl part of which contains 1 to 4 carbon atoms, or alkoxycarbonyl radical, the alkoxy part of which contains 1 to 4

REFERENCES:
Tetrahedron Letters, vol. 33, No. 36, 1 Sep. 1992, Oxford, GB pp. 5185-5188, A. Commercon et al.

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