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1. US6288066 - Polyhydroxybutylpyrazines, their preparation and medicaments comprising them

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What is claimed is:

1. A pharmaceutical composition comprising a compound of formula:

(MOL) (CDX)   in which either (A) R9 and R10 are identical and each is a —CH2OH radical and either
a) R 3 is a methylene radical, R 4 is a —CHOH— radical and one of the R 1, R 2, R 5 and R 6 radicals is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical and each of the others is a —CHOH— radical, or
b) R 2 and R 5 each is a —CHOH— radical, R 3 is a methylene radical and R 1, R 4 and R 6 are identical and each is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical, or
c) R 1, and R 6 each is a —CHOH— radical, R 3 is a methylene radical and R 2, R 4 and R 5 are identical and each is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical, or
d) R 1, R 4, R 5 and R 6 each is a —CHOH— radical and —R 2—R 3— is a —CH═CH— radical,
or (B) R1, R2, R4, R5 and R6 each is a —CHOH— radical, R3 is a methylene radical, R9 is a —CH2F or —CH2OH radical, R10 is a —CH2F or —CH2OH radical, R9 and R10 not both being a —CH2OH radical, R7 is a hydrogen atom or an alkyl, —CO—alk, —CO—Ar or —CO—Het radical,R8 is an alkyl, —alk—COOH or —alk—OH radical, alk being an alkyl radical,Ar is a phenyl radical or a phenyl radical substituted by one or more substituents selected from a halogen atom and alkyl, alkoxy, alkoxycarbonyl, amino, monoalkylamino and dialkylamino radicals,Het is a saturated or unsaturated, mono-, di- or tricyclic heterocycle comprising 1 to 9 carbon atoms and one or more heteroatoms selected from oxygen, sulphur and nitrogen,the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or its stereoisomers or, for a compound in which —R2—R3— represents a —CH═CH— radical, its cis or trans forms, or its salts with a pharmaceutically acceptable inorganic or organic acid.
 
2. A pharmaceutical composition according to claim 1, wherein Het is a heterocycle selected from the 2-, 3- and 4-pyridyl, imidazolyl, thiazolyl and oxazolyl rings.
 
3. A pharmaceutical composition according to claim 1, wherein said compound is selected from the group consisting of:
1-[5-(3R,4-Dihydroxy-2-oxobutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S,4-Dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-Fluoro-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-Fluoro-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-Amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-Amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(N-Methyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(N-Methyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(N-Ethyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(N-Ethyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(N-n-Butyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(N-n-Butyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(N-Benzyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(N-Benzyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(N-Acetyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(N-Acetyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(N-Butanoyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(N-Butanoyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(N-Benzoyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(N-Benzoyl)amino-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-Methoxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-Methoxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-Ethoxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-Ethoxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-n-Butoxy-3S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-n-Butoxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(2-Hydroxyethyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(2-Hydroxyethyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(3-Hydroxy-n-propyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(3-Hydroxy-n-propyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(Carboxymethyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(Carboxymethyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-(3-Carboxy-n-propyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-(3-Carboxy-n-propyl)oxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S,4-Dihydroxy-3-oxobutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S,4-Dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-Fluoro-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-Fluoro-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-Amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-Amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(N-Methyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(N-Methyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(N-Ethyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(N-Ethyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(N-n-Butyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(N-n-Butyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(N-Benzyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(N-Benzyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(N-Acetyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(N-Acetyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(N-Butanoyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(N-Butanoyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(N-Benzoyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(N-Benzoyl)amino-2R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-Methoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-Methoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-Ethoxy-2S, 4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-Ethoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-n-Butoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-n-Butoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(2-Hydroxyethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(2-Hydroxyethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(3-Hydroxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(3-Hydroxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(Carboxymethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-(5-(3S-(Carboxymethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3R-(3-Carboxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S-(3-Carboxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
4-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-1,3S,4R-trihydroxybutane-2-one,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]butane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-fluorobutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-fluorobutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-(N-methyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-(N-methyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-(N-ethyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-(N-ethyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-(N-n-butyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-(N-n-butyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-(N-benzyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-(N-benzyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-(N-acetyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-(N-acetyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-(N-butanoyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-(N-butanoyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-(N-benzoyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-(N-benzoyl)aminobutane-1R,2R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-methoxybutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-methoxybutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-ethoxybutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-ethoxybutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-n-butoxybutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-n-butoxybutane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-[(2-hydroxyethyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-[(2-hydroxyethyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-[(3-hydroxy-n-propyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-[(3-hydroxy-n-propyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-[(carboxymethyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-[(carboxymethyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3R-[(3-carboxy-n-propyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-3S-[(3-carboxy-n-propyl)oxy]butane-1R,2S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-1R,3R,4-trihydroxybutane-2-one,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-fluorobutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-fluorobutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-(N-methyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-(N-methyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-(N-ethyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-(N-ethyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-(N-n-butyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-(N-n-butyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-(N-benzyl)aminbutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-(N-benzyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-(N-acetyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-(N-acetyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-(N-butanoyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-(N-butanoyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-(N-benzoyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-(N-benzoyl)aminobutane-1S,3S,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-methoxybutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-methoxybutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-ethoxybutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-ethoxybutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-n-butoxybutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-n-butoxybutane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-[(2-hydroxyethyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-[(2-hydroxyethyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-[(3-hydroxy-n-propyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-[(3-hydroxy-n-propyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-[(carboxymethyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-[(carboxymethyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2R-[(3-carboxy-n-propyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,3R,4-Trihydroxybutyl)pyrazin-2-yl]-2S-[(3-carboxy-n-propyl)oxy]butane-1R,3R,4-triol,
1-[5-(2S,4-Dihydroxy-3-oxobutyl)pyrazin-2-yl]-2S,4-dihydroxybutane-1,3-diane,
4-[5-(2S,4-Dihydroxybutyl)pyrazin-2-yl]butane-1,3S-diol,
4-[5-(3R-Fluoro-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-difluorobutane-1,3S-diol,
4-[5-(3S-Fluoro-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-difluorobutane-1,3S-diol,
1-[5-(3R-Amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-diaminobutane-1,3S-diol,
1-[5-(3S-Amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-diaminobutane-1,3S-diol,
1-[5-(3R-(N-Methyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-methyl)amino]butane-1,3S-diol,
1-[5-(3S-(N-Methyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-methyl)amino]butane-1,3S-diol,
1-[5-(3R-(N-Ethyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-ethyl)amino]butane-1,3S-diol,
1-[5-(3S-(N-Ethyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-ethyl)amino]butane-1,3S-diol,
1-[5-(3R-(N-n-Butyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-n-butyl)amino]butane-1,3S-diol,
1-[5-(3S-(N-n-Butyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-n-butyl)amino]butane-1,3S-diol,
1-[5-(3R-(N-Benzyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-benzyl)amino]butane-1,3S-diol,
1-[5-(3S-(N-Benzyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-benzyl)amino]butane-1,3S-diol,
1-[5-(3R-(N-Acetyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-acetyl)amino]butane-1,3S-diol,
1-[5-(3S-(N-Acetyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-acetyl)amino]butane-1,3S-diol,
1-[5-(3R-(N-Butanoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-butanoyl)amino]butane-1,3S-diol,
1-[5-(3S-(N-Butanoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-butanoyl)amino]butane-1,3S-diol,
1-[5-(3R-(N-Benzoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-benzoyl)amino]butane-1,3S-diol,
1-[5-(3S-(N-Benzoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-benzoyl)amino]butane-1,3S-diol,
1-[5-(3R-Methoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-dimethoxybutane-1,3S-diol,
1-[5-(3S-Methoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-dimethoxybutane-1,3S-diol,
1-[5-(3R-Ethoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-diethoxybutane-1,3S-diol,
1-[5-(3S-Ethoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-diethoxybutane-1,3S-diol,
1-[5-(3R-n-Butoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di-n-butoxybutane-1,3S-diol,
1-[5-(3S-n-Butoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di-n-butoxybutane-1,3S-diol,
1-[5-(3R-(2-Hydroxyethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(2-hydroxyethyl)oxy]butane-1,3S-diol,
1-[5-(3S-(2-Hydroxyethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(2-hydroxyethyl)oxy]butane-1,3S-diol,
1-[5-(3R-(3-Hydroxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(3-hydroxy-n-propyl)oxy]butane-1,3S-diol,
1-[5-(3S-(3-Hydroxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(3-hydroxy-n-propyl)oxy]butane-1,3S-diol,
1-[5-(3R-(Carboxymethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(carboxymethyl)oxy]butane-1,3S-diol,
1-[5-(3S-(Carboxymethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(carboxymethyl)oxy]butane-1,3S-diol,
1-[5-(3R-(3-Carboxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(3-carboxy-n-propyl)oxy]butane-1,3S-diol,
1-[5-(3S-(3-Carboxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(3-carboxy-n-propyl)oxy]butane-1,3S-diol,
1-[5-(3R,4-Dihydroxy-2-oxobutyl)pyrazin-2-yl]-3R,4-dihydroxybutane-1,2-dione,
4-[5-(2S,4-Dihydroxybutyl)pyrazin-2-yl]butane-1,3S-diol,
4-[5-(3R-Fluoro-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-difluorobutane-1,3S-diol,
4-[5-(3S-Fluoro-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-difluorobutane-1,3S-diol,
4-[5-(3R-Amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-diaminobutane-1,3S-diol,
4-[5-(3S-Amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-diaminobutane-1,3S-diol,
4-[5-(3R-(N-Methyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-methyl)amino]butane-1,3S-diol,
4-[5-(3S-(N-Methyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-methyl)amino]butane-1,3S-diol,
4-[5-(3R-(N-Ethyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-ethyl)amino]butane-1,3S-diol,
4-[5-(3S-(N-Ethyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-ethyl)amino]butane-1,3S-diol,
4-[5-(3R-(N-n-Butyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-n-butyl)amino]butane-1,3S-diol,
4-[5-(3S-(N-n-Butyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-n-butyl)amino]butane-1,3S-diol,
4-[5-(3R-(N-Benzyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-benzyl)amino]butane-1,3S-diol,
4-[5-(3S-(N-Benzyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-benzyl)amino]butane-1,3S-diol,
4-[5-(3R-(N-Acetyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-acetyl)amino]butane-1,3S-diol,
4-[5-(3S-(N-Acetyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-acetyl)amino]butane-1,3S-diol,
4-[5-(3R-(N-Butanoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-butanoyl)amino]butane-1,3S-diol,
4-[5-(3S-(N-Butanoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-butanoyl)amino]butane-1,3S-diol,
4-[5-(3R-(N-Benzoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(N-benzoyl)amino]butane-1,3S-diol,
4-[5-(3S-(N-Benzoyl)amino-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(N-benzoyl)amino]butane-1,3S-diol,
4-[5-(3R-Methoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-dimethoxybutane-1,3S-diol,
4-[5-(3S-Methoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-dimethoxybutane-1,3S-diol,
4-[5-(3R-Ethoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-diethoxybutane-1,3S-diol,
4-[5-(3S-Ethoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-diethoxybutane-1,3S-diol,
4-[5-(3R-n-Butoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di-n-butoxybutane-1,3S-diol,
4-[5-(3S-n-Butoxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di-n-butoxybutane-1,3S-diol,
4-[5-(3R-(2-Hydroxyethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(2-hydroxyethyl)oxy]butane-1,3S-diol,
4-[5-(3S-(2-Hydroxyethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(2-hydroxyethyl)oxy]butane-1,3S-diol,
4-[5-(3R-(3-Hydroxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(3-hydroxy-n-propyl)oxy]butane-1,3S-diol,
4-[5-(3S-(3-Hydroxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(3-hydroxy-n-propyl)oxy]butane-1,3S-diol,
4-[5-(3R-(Carboxymethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(carboxymethyl)oxy]butane-1,3S-diol,
4-[5-(3S-(Carboxymethyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(carboxymethyl)oxy]butane-1,3S-diol,
4-[5-(3R-(3-Carboxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2R,4R-di[(3-carboxy-n-propyl)oxy]butane-1,3S-diol,
4-[5-(3S-(3-Carboxy-n-propyl)oxy-2S,4-dihydroxybutyl)pyrazin-2-yl]-2S,4S-di[(3-carboxy-n-propyl)oxy]butane-1,3S-diol,
1-[5-(3S,4-Dihydroxy-1E-butenyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
4-Fluoro-1-[5-(2S,3R,4-trihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3S-triol,
1-[5-(4-Fluoro-2S,3S-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol
and their salts with a pharmaceutically acceptable inorganic or organic acid.
 
4. A pharmaceutical composition according to claim 1 in which, either (A) R9 and R10 each is a —CH2OH radical, and either
a) R 3 is a methylene radical, R 4 is a —CHOH— radical and one of the R 1, R 2, R 5 and R 6 radicals is a —CHF or —CH(OR 8) radical and each of the others is a —CHOH— radical, or
b) R 2 and R 5 each is a —CHOH— radical, R 3 is a methylene radical and R 1, R 4 and R 6 are identical and each is a —CH(OR 8) radical, or
c) R 1 and R 6 each is a —CHOH— radical, R 3 is a methylene radical and R 2, R 4 and R 5 are identical and each is a —CH(OR 8) radical, or
d) R 1, R 4, R 5 and R 6 each is a —CHOH— radical and —R 2—R 3— is a —CH═CH— radical,
or (B) R1, R2, R4, R5 and R6 each is a —CHOH— radical, R3 is a methylene radical, R9 is a —CH2OH radical, R10 is a —CH2F radical, and R8 is an alkyl radical.
 
5. A pharmaceutical composition comprising, as an active ingredient, at least one compound according to claim 1 selected from the group consisting of:
1-[5-(3S,4-Dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(3S,4-Dihydroxy-1E-butenyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S-Methoxy-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2R-Fluoro-3R,4-dihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
1-[5-(2S,4-Dihydroxy-3R-methoxybutyl)pyrazin-2-yl]butane-1R,2S,3R,4-tetraol,
4-[5-(3R,4-Dihydroxy-2S-methoxybutyl)]pyrazin-2-yl]-3R,4R-dimethoxybutane-1,2-diol,
4-Fluoro-1-[5-(2S,3R,4-trihydroxybutyl)pyrazin-2-yl]butane-1R,2S,3R-triol,
and their salts with a pharmaceutically acceptable inorganic or organic acid.
 
6. A compound of formula:

(MOL) (CDX)   in which either (A) R9 and R10 each is a —CH2OH radical, and either
a) R 3 is a methylene radical, R 4 is a —CHOH— radical and one of the R 1, R 2, R 5 and R 6 radicals is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical and each of the others is a —CHOH— radical, or
b) R 2 and R 5 each is a —CHOH— radical, R 3 is a methylene radical and R 1, R 4 and R 6 are identical and each is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical, or
c) R 1 and R 6 each is a —CHOH— radical, R 3 is a methylene radical and R 2, R 4 and R 5 are identical and each is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical, or
d) R 1, R 4, R 5 and R 6 each is a —CHOH— radical and —R 2—R 3— is a —CH═CH— radical,
or (B) R1, R2, R4, R5 and R6 each is a —CHOH— radical, R3 is a methylene radical, R9 is a —CH2F or —CH2OH radical, R10 is a —CH2F or —CH2OH radical, R9 and R10 not both being a —CH2OH radical, R7 is a hydrogen atom or an alkyl, —CO—alk, —CO—Ar or —CO—Het radical,R8 is an alkyl, —alk—COOH or —alk—OH radical, alk is an alkyl radical,Ar is a phenyl radical or a phenyl radical substituted by one or more substituents selected from a halogen atom and the alkyl, alkoxy, alkoxycarbonyl, amino, monoalkylamino and dialkylamino radicals,Het is a saturated or unsaturated, mono-, di- or tricyclic heterocycle comprising 1 to 9 carbon atoms and one or more heteroatoms selected from oxygen, sulphur and nitrogen,the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or one of its stereoisomers or, for a compound in which —R2—R3— represents a —CH═CH— radical, its cis or trans forms, or one of its salts with an organic or inorganic acid, provided, however, that said compound is not the compound of formula:

(MOL) (CDX)  
 
7. A process for the preparation of a compound according to claim 6 in which R9 and R10 each is a —CH2OH radical and either R3 is a methylene radical, R4 is a —CHOH— radical and one of the R1, R2, R5 and R6 radicals is a carbonyl radical and each of the others is a —CHOH— radical or R1 and R6 each is a —CHOH— radical, R3 is a methylene radical and R2, R4 and R5 are identical and each is a carbonyl radical or R2 and R5 each is a —CHOH— radical, R3 is a methylene radical and R1, R4 and R6 are identical and each is a carbonyl radical, in which process a compound selected from compounds of the formulae:

(MOL) (CDX)

(MOL) (CDX)   in which Ra is a trialkylsilyl, alkyldiphenylsilyl or dialkylphenylsilyl radical, Rb is a phenyl radical optionally substituted with least one alkoxy radical and Rc is an alkyl or phenyl radical, the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or a stereoisomer of such a derivative, is oxidized, the hydroxyls are then deprotected and the product is isolated and optionally converted to a salt.
 
8. A process for the preparation of a compound according to claim 6 in which (i) R9 and R10 each is a —CH2OH radical and R3 is a methylene radical, R4 is a —CHOH— radical and one of the R1, R2, R5 and R6 radicals is a methylene radical and each of the others is a —CHOH— radical or (ii) R1 and R6 each is a —CHOH— radical, R3 is a methylene radical and R2, R4 and R5 are identical and each is a methylene radical or (iii) R2 and R5 each is a —CHOH— radical and R1, R3, R4 and R6 each is a methylene radical, in which process an alkyl or phenyl chlorothionocarbonate is condensed with a compound selected from compounds of the following formulae:

(MOL) (CDX)

(MOL) (CDX)   in which Ra is a trialkylsilyl, alkyldiphenylsilyl or dialkylphenylsilyl radical, Rb is a phenyl radical optionally substituted by at least one alkoxy radical and Rc is an alkyl or phenyl radical, the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or a stereoisomer of such a compound, the hydroxyls are then deprotected and the product is isolated and optionally converted to a salt.
 
9. A process for the preparation of a compound obtained product is reduced and the according to claim 6 in which either (A) R9 and R10 each is a —CH2OH radical and either R3 is a methylene radical, R4 is a —CHOH— radical and one of the R1, R2, R5 and R6 radicals is a —CHF— radical and each of the others is a —CHOH— radical or R1 and R6 each is a —CHOH— radical, R3 is a methylene radical and R2, R4 and R5 are identical and each is a —CHF— radical or R2 and R5 each is a —CHOH— radical, R3 is a methylene radical and R1, R4 and R6 are identical and each is a —CHF— radical or (B) R1, R2, R4, R5 and R6 each is a —CHOH— radical, R3 is a methylene radical, R9 is a —CH2F or —CH2OH radical, R10 is a —CH2F or —CH2OH radical, R9 and R10 not both being a —CH2OH radical, in which process a compound selected from compounds of the formulae:

(MOL) (CDX)

(MOL) (CDX)   in which Ra is a trialkylsilyl, alkyldiphenylsilyl or dialkylphenylsilyl radical, Rb is a phenyl radical optionally substituted with at least one alkoxy radical and Rc is an alkyl or phenyl radical, the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or a stereoisomer of such a derivative is fluorinated, the hydroxyls are then deprotected and the product is isolated and optionally converted to a salt.
 
10. A process for the preparation of a compound according to claim 6 in which R9 and R10 each is a —CH2OH radical and either R3 is a methylene radical, R4 is a —CHOH— radical and one of the R1, R2, R5 and R6 radicals is a —CH(NHR7)— radical and each of the others is a —CHOH— radical or R1 and R6 each is a —CHOH— radical, R3 is a methylene radical and R2, R4 and R5 are identical and each is a —CH(NHR7)— radical or R2 and R5 each is a —CHOH— radical, R3 is a methylene radical and R1, R4 and R6 are identical and each is a —CH(NHR7)— radical, said process comprising reducing a compound selected from compounds of the formulae:

(MOL) (CDX)

(MOL) (CDX)   in which Ra is a trialkylsilyl, alkyldiphenylsilyl or dialkylphenylsilyl radical, Rb is a phenyl radical optionally substituted with at least one alkoxy radical, Rc is an alkyl or phenyl radical and Rd is an azido radical, the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or a stereoisomer of such a compound, optionally followed by reacting the product with a compound of formula HalR7, in which R7 has the same meanings as in claim 6, except that R7 is not hydrogen, and Hal is a halogen atom, deprotecting the hydroxyls and isolating the product and optionally converting it to a salt.
 
11. A process for the preparation of a compound according to claim 6 in which R9 and R11 each is a —CH2OH radical and either R3 is a methylene radical, R4 is a —CHOH— radical and one of the R1, R2, R5 and R6 radicals is a —CH(OR8) radical and each of the others is a —CHOH— radical or R1 and R6 each is a —CHOH— radical, R3 is a methylene radical and R2, R4 and R5 are identical and each is a —CH(OR8) radical or R2 and R5 each is a —CHOH— radical, R3 is a methylene radical and R1, R4 and R6 are identical and each is a —CH(OR8) radical, said process comprising reacting a compound of formula:

(MOL) (CDX)

(MOL) (CDX)   in which Ra is a trialkylsilyl, alkyldiphenylsilyl or dialkylphenylsilyl radical, Rb is a phenyl radical optionally substituted with at least one alkoxy radical and Rc is an alkyl or phenyl radical, the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or a stereoisomer of such a derivative, with a compound of formula HalR8, in which R8 has the same meanings as in claim 6, and Hal is a halogen, then deprotecting the hydroxyls and isolating the product and optionally converting it to a salt.
 
12. A process for the preparation of a compound according to claim 6 in which R9 and R10 each is a —CH2OH radical and R1, R4, R5 and R6 each is a —CHOH— radical and —R2—R3— is a —CH═CH— radical, in which process a compound of formula:

(MOL) (CDX)   in which Rd is an —OSO2—Re radical and Re is a methyl, trifluoromethyl or 4-methylphenyl radical, or a stereoisomer of such a derivative, is dehydrated, the hydroxyls are then deprotected and the product is isolated and optionally converted to a salt.
 
13. A method for the treatment or prevention of diabetes, or complications thereof, this method comprising administering to a patient in need of such treatment an effective amount of a compound of general formula:

(MOL) (CDX)   in which either (A) R9 and R10 are identical and each is a —CH2OH radical and either
a) R 3 is a methylene radical, R 4 is a —CHOH— radical and one of the R 1, R 2, R 5 and R 6 radicals is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical and each of the others each is a —CHOH— radical, or
b) R 2 and R 5 each is a —CHOH— radical, R 3 is a methylene radical and R 1, R 4 and R 6 are identical and each is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CHOR(OR 8) radical, or
c) R 1 and R 6 each is a —CHOH— radical, R 3 is a methylene radical and R 2, R 4 and R 5 are identical and each is a carbonyl, methylene, —CHF—, —CH(NHR 7)— or —CH(OR 8) radical, or
d) R 1, R 4, R 5 and R 6 each is a —CHOH— radical and —R 2—R 3— is a —CH═CH— radical,
or (B) R1, R2, R4, R5 and R6 each is a —CHOH— radical, R3 is a methylene radical, R9 is a —CH2F or —CH2OH radical and R10 is a —CH2F or —CH2OH radical, R9 and R10 not both being a —CH2OH radical, R7 is a hydrogen atom or an alkyl, —CO—alk, —CO—Ar or —CO—Het radical,R8 is an alkyl, —alk—COOH or —alk—OH radical, alk is an alkyl radical,Ar is a phenyl radical or a phenyl radical substituted with one or more substituents selected from a halogen atom and the alkyl, alkoxy, alkoxycarbonyl, amino, monoalkylamino and dialkylamino radicals,Het is a saturated or unsaturated, mono-, di- or tricyclic heterocycle comprising 1 to 9 carbon atoms and one or more heteroatoms selected from oxygen, sulphur and nitrogen,the alkyl and alkoxy radicals comprising 1 to 6 carbon atoms in a straight or branched chain, or one of its stereoisomers or, for a compound in which —R2—R3— represents a —CH═CH— radical, its cis or trans forms, or its salt with a pharmaceutically acceptable inorganic or organic acid in a pharmaceutically acceptable vehicle.
 
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