Novel intermediates for use in retinoid synthesis
AssigneeCentre National de la Recherche Scientifique (CNRS)
InventorsAlain Valla, Dominique Cartier, Roger Labia, Pierre Potier
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Abstract
The invention concerns compounds of formula (I) wherein in particular G represents the —N(CH3)2—, —N(C2H5)2-group or N-pyrrolidine: n is an integer equal to 1 or 2: R1, R2 and R3, independently of one another, represent a hydrogen atom or a methyl group, the successive unsaturated units capable of being moreover identical or different, provided that at least one of the substituents R1, R2, and R3 is different from H: and Y1 and Y2 represent each a —COOCH3 group or a COOC2H5 group.
Claims9
1-19. (canceled)
A method for synthesizing a compound of formula (1)
- wherein
- G represents a —NR4R5 group where R4 and R5, which are identical or different, are each a linear or branched alkyl group of 1 to 5 carbon atoms, or a cycloalkyl group of 3 to 7 carbon atoms, or R4 and R5 together with the nitrogen atom carrying them form a ring,
- R1 represents a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms,
- n is an integer equal to 1 or 2,
- R2 and R3 represent identical or different substituent in each unsaturated unit, successive unsaturated units being identical or different, R2 and R3 being hydrogen or a linear or branched alkyl group of 1 to 5 carbon atoms, and provided that at least one of the substituents RI, R2 and R3 is different from hydrogen, and
- Y1 and Y2 each represent a COOR7 group where R7 is an alkyl group of 1 to 5 carbon atoms, having n+1 units from a compound of formula (1) having n units, comprising reacting an organometallic in a solvent with the compound of formula (1) having n units to obtain a compound of formula (3)
- in which R1, R2 and R3, Y1 and Y2 are as defined above and R represents a corresponding alkyl group of 1 or 2 carbon atoms,
- and treating the compound of formula (3) with an N,N-dimethylformaide or acetamide derivative.
A method for synthesizing a compound of formula (1)
- wherein
- G represents a —NR4R5 group where R4 and R5, which are identical or different, are each a linear or branched alkyl group of 1 to 5 carbon atoms, or a cycloalkyl group of 3 to 7 carbon atoms, or R4 and R5 together with the nitrogen atom carrying them form a ring,
- R1 represents a hydrogen atom or a linear or branched alkyl group of 1 to 5 carbon atoms,
- n is an integer equal to 1 or 2,
- R2 and R3 represent an identical or different substituent in each unsaturated unit, successive unsaturated units being identical or different, R2 and R3 being hydrogen or a linear or branched alkyl group of 1 to 5 carbon atoms, and provided that at least one of the subsituents R1, R2 and R3 is different from hydrogen, and
- Y1 and Y2 each represent a COOR7 group where R7 is an alkyl group of 1 to 5 carbon atoms having n+2 units from a compound of formula (1) having n units, comprising reacting the compound of formula (1) having n units in a solvent with an enolate of a ketone, said enolate being generated by a base, and then adding an organometallic to obtain a compound of formula (3):
- in which R1, R2 and R3, Y1 and Y2 are defined above and R represents a corresponding alkyl group of I or 2 carbon atoms and treating the compound of formula (3) with an N,N-dimethylformamide or acetamide derivative.
Dependencies are inferred from the claim text.