Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-09-28
1999-12-14
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546 21, C07F 960, C07F 96558, C07D21514, C07D40506
Patent
active
060020067
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE
This application is a 5371 of PCT/PR97/00352 filed Feb. 27, 1997.
The present invention relates to new derivatives of 1(2H) quinoline carboxylic acid, their preparation process and their use for the synthesis of products endowed with antibiotic properties.
A subject of the invention is the compounds of formula (I): ##STR3## in which alc.sub.1, alc.sub.2 and alc.sub.3 identical to or different from each other represent an alkyl radical containing up to 8 carbon atoms, n represents an integer which can vary from 0 to 8, R.sub.1 and R.sub.2 represent an O-alkyl radical containing up to 8 carbon atoms, or form together with the carbon atom to which they are linked a cyclic acetal.
The alkyl radical is preferably a methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl or terbutyl radical.
When R.sub.1 and R.sub.2 form with the carbon atom to which they are linked a cyclic acetal, it is preferably a: ##STR4## group in which p represents the number 1, 2, 3 or 4.
A quite particular subject of the invention is the compounds of formula (I) in which n represents the number 2, as well as those in which alc.sub.1, alc.sub.2 and alc.sub.3 represent an ethyl radical.
Among the preferred compounds of the invention there can be mentioned the compounds of formula (I) in which R.sub.1 and R.sub.2 form together with the carbon atom to which they are linked a 1,3-dioxolane: ##STR5## or 1,3-dioxane radical ##STR6##
A quite particular subject of the invention is the compound of formula (I) the preparation of which is given hereafter in the experimental part.
A subject of the invention is also a preparation process for compounds of formula (I), characterized in that a compound of formula (II): ##STR7## in which alc.sub.1, alc.sub.2 and alc.sub.3 retain their previous meaning is subjected to the action of a compound of formula (III): ##STR8## in which Hal represents a halogen atom and R.sub.1, R.sub.2 and n retain their previous meaning, in order to obtain the corresponding compound of formula (I).
The compounds of formula (II) used as starting products for the process of the invention can be prepared according to the processes described in Tetrah. Lett. 23(16), 1709-12 (1982) or in the Japanese Patent Application 1221-102.
In a preferred implementation of the process of the invention, Hal is a bromine or chlorine atom.
A particular subject of the invention is a process characterized in that the operation is carried out in the presence of a strong base.
The base used is butyllithium, or an alkaline or alkali earth alcoholate, for example lithium, sodium, or potassium terbutylate or teramylate or also lithium hydroxide. Sodium or potassium terbutylate or teramylate is preferably used.
Furthermore a subject of the invention is the use characterized in that a compound of formula (I) is subjected to the action of a strong base in order to obtain the corresponding compound of formula (IV): ##STR9## in which n, R.sub.1 and R.sub.2 retain their previous meaning.
A more particular subject of the invention is the use characterized in that the strong base can be soda or preferably sodium ethylate.
The operation can also be carried out in the presence of an alkaline iodide such as sodium iodide in an aprotic polar solvent at high temperature.
Advantageously, and in particular when R.sub.1 and R.sub.2 form together with the carbon atom to which they are linked a cyclic acetal, the product of formula (IV) is purified in the form of the hydrochloride but it can also be in the form of the aldehyde hydrate.
A more particular subject of the invention is the use of the compound of Example 1 or 2, for the preparation of the products of formula (IV) described in the experimental part.
The compounds of formula (IV) are products known in a general fashion; they can also be prepared according to the process described in European Patent Application 676409.
The products of formula (IV) can be converted into the corresponding aldehydes: ##STR10## and then be converted into products having antibiotic properties according to the process descri
REFERENCES:
Kin-ya Akiba et al. Tetrahedron Letters,vol.23, No. 16, pp.-1709-1712, 1982.
Akiba et al, "Regioselective . . . -2-Phosphonates", Tetrahedron Letters vol. 23, No. 16, pp. 1709-1712, 1982, XP 000611889.
Akiba et al. "Quinolinephosphonate Derivatives", Chemical Abstracts, vol. 106, No. 13, Mar. 30, 1987, p. 684 XP 002018371.
Bonnet Alain
Bouchet Raphael
Guilmard Daniel
Mazurie Alain
Hoechst Marion Roussel
Rotman Alan L.
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