Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-01-18
2001-09-11
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S336000
Reexamination Certificate
active
06288066
ABSTRACT:
The present invention relates to medicaments comprising, as active principle, at least one compound of formula:
or one of its stereoisomers or one of its salts, to novel compounds of formula (I), their stereoisomers and their salts, and to their process of preparation.
In the formula (I) either (A) R
9
and R
10
each represent a —CH
2
OH radical, and either
a) R
3
represents a methylene radical, R
4
represents a —CHOH— radical and one of the R
1
, R
2
, R
5
and R
6
radicals represents a carbonyl, methylene, —CHF—, —CH(NHR
7
)— or —CH(OR
8
) radical and the others each represent a —CHOH— radical,
b) R
2
and R
5
each represent a —CHOH— radical, R
3
represents a methylene radical and R
1
, R
4
and R
6
are identical and each represent a carbonyl, methylene, —CHF—, —CH(NHR
7
)— or —CH(OR
8
) radical,
c) R
1
and R
6
each represent a —CHOH— radical, R
3
represents a methylene radical and R
2
, R
4
and R
5
are identical and each represent a carbonyl, methylene, —CHF—, —CH(NHR
7
)— or —CH(OR
8
) radical,
d) R
1
, R
4
, R
5
and R
6
each represent a —CHOH— radical and —R
2
—R
3
— represents a —CH═CH— radical,
or (B) R
1
, R
2
, R
4
, R
5
and R
6
each represent a —CHOH— radical, R
3
represents a methylene radical, R
9
represents a —CH
2
F or —CH
2
OH radical, R
10
represents a —CH
2
F or —CH
2
OH radical, R
9
and R
10
not both being a —CH
2
OH radical,
R
7
represents a hydrogen atom or an alkyl, —CO—alk, —CO—Ar or —CO—Het radical,
R
8
represents an alkyl, —alk—COOH or —alk—OH radical, alk represents an alkyl radical,
Ar represents a phenyl radical or a phenyl radical substituted by one or more substituents chosen from a halogen atom or an alkyl, alkoxy, alkoxycarbonyl, amino, monoalkylamino or dialkylamino radical,
Het represents a saturated or unsaturated, mono-, di- or tricyclic heterocycle comprising 1 to 9 carbon atoms and one or more heteroatoms chosen from oxygen, sulphur and nitrogen.
In the preceding and succeeding definitions, the alkyl and alkoxy radicals and portions comprise 1 to 6 carbon atoms in a straight or branched chain and the halogen atoms are chlorine, fluorine, iodine and bromine atoms.
As the compounds of formula (I) comprise several asymmetric carbons, [lacuna] exhibit stereoisomeric forms. These various stereoisomers form part of the invention. In addition, the compounds in which —R
2
—R
3
— represents a —CH═CH— radical can exist in the cis or trans form; these forms also form part of the invention.
Het preferably represents a heterocycle chosen from 2-, 3- or 4-pyridyl, imidazolyl, thiazolyl and oxazolyl rings.
In other words, the compounds of formula (I) correspond to the following formulae: in which R represents represents a carbonyl, methylene, —CHF—, —CH(NHR
7
)— or —CH(OR
8
) radical, R
7
, R
8
, R
9
and R
10
having the same meanings as above, their stereoisomeric forms and the cis and trans forms of the compounds comprising a CH═CH chain.
The preferred medicaments are those which comprise, as active principle, at least one compound of formula (I) chosen from the following compounds:
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-y]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-Met
Bashiardes Georges
Carry Jean-Christophe
Evers Michel
Filoche Bruno
Mignani Serge
Aventis Pharma S.A.
Balasubramanian Venkataraman
Newman Irving
Shah Mukund J.
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