Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-03-10
1999-10-19
Owens, Amelia
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D31304
Patent
active
059691611
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new derivatives of 5-O-desosaminyl 6-O-methyl erythronolide A, their preparation process and their use for the preparation of biologically-active products.
A subject of the invention is the compounds of formula (I): ##STR2## in which: either R.sub.1 represents an alkyl radical containing up to 8 carbon atoms substituted by one or more alkyl radicals containing up to 8 carbon atoms, or by one or more aryl radicals containing up to 14 carbon atoms, optionally substituted by one or more alkyl, alkenyl or alkynyl radicals containing up to 8 carbon atoms, alkoxy or alkylthio radicals containing up to 8 carbon atoms, nitro, CF.sub.3 radicals or by one or more halogen atoms, ##STR3## in which Ra represents an alkyl or alkoxy radical containing up to 8 carbon atoms, substituted by a heteroatom, atoms, radical in which the alkyl radical contains up to 8 carbon atoms, ##STR4## in which R'a, R'b, R'c and Rd represent an alkyl radical containing up to 8 carbon atoms, or an aralkyl radical containing up to 8 carbon atoms, optionally substituted by one or or more of the substituents indicated above for R.sub.1.
In the definition of compounds of the invention: radicals: methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, terbutyl, decyl or dodecyl, vinyl, allyl, ethynyl, propynyl, cyclobutyl, cyclopentyl or cyclohexyl, radical, a being an integer comprised between 1 and 6, for example the number 1, 2, 3 or 4; the aralkyl radical can be for example, an optionally substituted benzyl radical or a trityl radical, ethoxy, propyloxy isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, sec-pentyloxy, tert-pentyloxy, neopentyloxy, n-hexyloxy, sec-hexyloxy, tert-hexyloxy, and replacing the oxygen atom with a sulphur atom, for example: methylthio, ethylthio. Furthermore, the sulphur atom can be oxidized, for example: methylsulphinyl, methylsulphonyl.
The compounds of the invention can be used for the preparation of compounds of formula (VI): ##STR5## in which Z represents a hydrogen atom or a protective group such as the remainder of a carboxylic acid containing up to 8 carbon atoms, a trialkylsilyl or terbutyl radical. The compounds of formula (VI) are described and claimed in the European Patent Application 0,487,411, as intermediates useful in particular for the preparation of antibiotic products.
A more particular subject of the invention is the compounds of formula (I) in which R.sub.1 represents a ##STR6## radical in which Ra, Rb and Rc retain the same meaning as previously and in particular those in which Ra, Rb and Rc represent a methyl radical as well as the compounds of formula (I) in which R.sub.2 and R.sub.3 both represent a trialkylsilyl radical and in particular those in which R.sub.2 and R.sub.3 represent a trimethylsilyl radical.
A more particular subject of the invention is the compound of formula (I) whose preparation is given hereafter in the experimental part.
A subject of the invention is also a preparation process for the compounds of formula (I) as defined previously, characterized in that the compound of formula (II): ##STR7## is subjected to the action of an agent blocking the oxime in position 9, in order to obtain a compound of formula (III): ##STR8## in which R.sub.1 retains its previous meaning, which is subjected to the action of an agent blocking the hydroxyl in position 3 and/or in position 2' in order to obtain the compound of formula (IV): ##STR9## in which R.sub.1, R.sub.2 and R.sub.3 retain their previous meaning, which is subjected to the action of a methylation agent of the hydroxyl in position 6, in order to obtain the corresponding compound of formula (I).
The compound of formula (II) used as starting product is a known product described by Le Mahieu et al. in J. Med. Chem. 17 (9) 953-956 (1974).
In a preferred implementation of the process of the invention: base for example potash, soda, a hydride such as sodium hydride, an alkali metal terbutylate such as for example potassium terbutylate or also in the presence of 1,5-diazabicy
Bonnet Alain
Delthil Michel
Mazurie Alain
Hoechst Marion Roussel
Owens Amelia
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