Pyrazine derivatives, their preparation and medicaments...

Details Pyrazine derivatives, their preparation and medicaments... Pyrazine derivatives, their preparation and medicaments...

2000-01-14

2002-06-04

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S336000, C544S387000, C514S183000

Reexamination Certificate

active

06399613

ABSTRACT:

The present invention relates to medicaments containing, as active principle, a compound of formula:
a stereoisomer or a salt of such a compound with an inorganic or organic acid, to the novel compounds of formula (I) and to a process for their preparation.
In formula (I) either
R represents a nitrogen atom, R
1
represents a radical —CO—NR
5
R
6
, —CO—N(CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
OH)
2
, —CO—N(CH
2
—CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
—(CHOH)
n
—CH
2
OH)
2
in which n is equal to 0, 1, 2, 3 or 4, —CH
2
—O—R
6
, —NR
5
—CO—R
6
, —CH
2
—NR
5
R
6
, —CH
2
—N (CH
2
OH)
2
, —CH
2
—N(CH
2
—(CHOH)
y
—CH
2
OH)
2
in which y is equal to 0, 1, 2, 3 or 4, —CH
2
—N(CH(CH
2
OH)
2
)
2
or —CH
2
—N(CH
2
—CH(CH
2
OH)
2
)
2
and one of the substituents R
3
or R
4
represents a hydrogen atom and the other is identical to R
1
and R
2
represents a hydrogen atom, or R represents a CH residue, R
1
and R
4
are identical and each represent a radical —CO—NR
5
R
6
, —CO—N(CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
OH)
2
, —CO—N(CH
2
—CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
—(CHOH)
n
—CH
2
OH)
2
in which n is equal to 0, 1, 2, 3 or 4, —CH
2
—O—R
6
, —NR
5
—CO—R
6
, —CH
2
—NR
5
R
6
, —CH
2
—N(CH
2
OH)
2
, —CH
2
—N(CH
2
—(CHOH)
y
—CH
2
OH)
2
in which y is equal to 0, 1, 2, 3 or 4, —CH
2
—N(CH(CH
2
OH)
2
)
2
or —CH
2
—N(CH
2
—CH(CH
2
OH)
2
)
2
and R
2
and R
3
each represent a hydrogen atom, or R represents a CH residue, R
1
and R
3
are identical and each represent a radical —CO—NR
5
R
6
, —CO—N(CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
OH)
2
, —CO—N(CH
2
—CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
—(CHOH)
n
—CH
2
OH)
2
in which n is equal to 0, 1, 2, 3 or 4, —CH
2
—O—R
6
, —NR
5
—CO—R
6
, —CH
2
—NR
5
R
6
, —CH
2
—N(CH
2
OH)
2
, —CH
2
—N(CH
2
—(CHOH)
y
—CH
2
OH)
2
in which y is equal to 0, 1, 2, 3 or 4, —CH
2
—N(CH(CH
2
OH)
2
)
2
or —CH
2
—N(CH
2
—CH(CH
2
OH)
2
)
2
and R
2
and R
4
each represent a hydrogen atom,
or R represents a CH residue, R
2
and R
3
are identical and each represent a radical —CO—NR
5
R
6
, —CO—N(CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
OH)
2
, —CO—N(CH
2
—CH(CH
2
OH)
2
)
2
, —CO—N(CH
2
—(CHOH)
n
—CH
2
OH)
2
in which n is equal to 0, 1, 2, 3 or 4, —CH
2
—O—R
6
, —NR
5
—CO—R
6
, —CH
2
—NR
5
R
6
, —CH
2
—N(CH
2
OH)
2
, —CH
2
—N(CH
2
—(CHOH)
y
—CH
2
OH)
2
in which y is equal to 0, 1, 2, 3 or 4, —CH
2
—N(CH(CH
2
OH)
2
)
2
or —CH
2
—N(CH
2
—CH(CH
2
OH)
2
)
2
and R
1
and R
4
each represent a hydrogen atom,
R
5
represents a hydrogen atom or an alkyl radical,
R
6
represents a radical —CH
2
—(CHOH)m—CH
2
OH in which m is equal to 0, 1, 2, 3 or 4, -alk-O-alk-CH
2
OH, -alk-O-alk, —CH(CH
2
OH)
2
, —C(CH
2
OH)
3
, —C(CH
3
) (CH
2
OH)
2
, —CH
2
—CH(CH
2
OH)
2
or —CH(CH
2
OH)—(CHOH)
x
—CH
2
OH in which x is equal to 1, 2, 3 or 4,
alk represents an alkyl radical.
In the definitions hereinabove and in those hereinbelow, the alkyl radicals contain 1 to 6 carbon atoms in a straight or branched chain.
The compounds of formula (I) containing asymmetric carbon atoms have stereoisomeric forms. These stereoisomers form part of the invention.
The preferred medicaments are those which contain a compound of formula (I) chosen from the following compounds:
N,N′-bis(2-hydroxyethyl)pyrazine-2,5-dicarboxamide,
N,N′-bis(2-hydroxyethyl)pyrazine-2,6-dicarboxamide,
N-methyl-N-(2-hydroxyethyl-N′-methyl-N′(2-hydroxyethyl)pyrazine-2,5-dicarboxamide,
N-methyl-N-(2-hydroxyethyl)-N′-methyl-N′(2-hydroxyethyl)pyrazine-2,6-dicarboxamide,
N,N,N′,N′-tetrakis(2-hydroxyethyl)pyrazine-2,5-dicarboxamide,
N,N,N′,N′-tetrakis(2-hydroxyethyl)pyrazine-2,6-dicarboxamide,
N,N′-bis(2,3-dihydroxy-1-propyl)pyrazine-2,5-dicarboxamide,
N,N′-bis(2,3-dihydroxy-1-propyl)pyrazine-2,6-dicarboxamide,
N-methyl-N-(2,3-dihydroxy-1-propyl)-N′-methyl-N′-(2,3-dihydroxy-1-propyl)pyrazine-2,5-dicarboxamide,
N-methyl-N-(2,3-dihydroxy-1-propyl)-N′-methyl-N′-(2,3-dihydroxy-1-propyl)pyrazine-2,6-dicarboxamide,
N,N,N′,N′-tetrakis(2,3-dihydroxy-1-propyl)pyrazine-2,5-dicarboxamide,
N,N,N′,N′-tetrakis(2,3-dihydroxy-1-propyl)pyrazine-2,6-dicarboxamide,
N,N′-bis(1,3-dihydroxy-2-propyl)pyrazine-2,5-dicarboxamide,
N,N′-bis(1,3-dihydroxy-2-propyl)pyrazine-2,6-dicarboxamide,
N-methyl-N-(1,3-dihydroxy-2-propyl)-N′-methyl-N′-(1,3-dihydroxy-2-propyl)pyrazine-2,5-dicarboxamide,
N-methyl-N-(1,3-dihydroxy-2-propyl)-N′-methyl-N′-(1,3-dihydroxy-2-propyl)pyrazine-2,6-dicarboxamide,
N,N,N′,N′-tetrakis(1,3-dihydroxy-2-propyl)pyrazine-2,5-dicarboxamide,
N,N,N′,N′-tetrakis(1,3-dihydroxy-2-propyl)pyrazine-2,6-dicarboxamide,
N,N′-bis(2,3,4-trihydroxy-1-butyl)pyrazine-2,5-dicarboxamide,
N,N′-bis(2,3,4-trihydroxy-1-butyl)pyrazine-2,6-dicarboxamide,
N-methyl-N-(2,3,4-trihydroxy-1-butyl)-N′-methyl-N′-(2,3,4-trihydroxy-1-butyl)pyrazine-2,5-dicarboxamide,
N-methyl-N-(2,3,4-trihydroxy-1-butyl)-N′-methyl-N′-(2,3,4-trihydroxy-1-butyl)pyrazine-2,6-dicarboxamide,
N,N′-bis(1,3,4-trihydroxy-2-butyl)pyrazine-2,5-dicarboxamide,
N,N′-bis(1,3,4-trihydroxy-2-butyl)pyrazine-2,6-dicarboxamide,
N-methyl-N-(1,3,4-trihydroxy-2-butyl)-N′-methyl-N′-(1,3,4-trihydroxy-2-butyl)pyrazine-2,5-dicarboxamide,
N-methyl-N-(1,3,4-trihydroxy-2-butyl)-N′-methyl-N′-(1,3,4-trihydroxy-2-butyl)pyrazine-2,6-dicarboxamide,
N,N′-bis[2-(hydroxymethyl)-3-hydroxy-1-propyl]-pyrazine-2,5-dicarboxamide,
N,N′-bis[2-(hydroxymethyl)-3-hydroxy-1-propyl]-pyrazine-2,6-dicarboxamide,
N-methyl-N-[2-(hydroxymethyl)-3-hydroxy-1-propyl]-N′-methyl-N′-[2-(hydroxymethyl)-3-hydroxy-1-propyl]-pyrazine-2,5-dicarboxamide,
N-methyl-N-[2-(hydroxymethyl)-3-hydroxy-1-propyl]-N′-methyl-N′-[2-(hydroxymethyl)-3-hydroxy-1-propyl]-pyrazine-2,6-dicarboxamide,
N,N,N′,N′-tetrakis[2-(hydroxymethyl)-3-hydroxy-1-propyl]pyrazine-2,5-dicarboxamide,
N,N,N′,N′-tetrakis[2-(hydroxymethyl)-3-hydroxy-1-propyl]pyrazine-2,6-dicarboxamide,
N,N′-bis[1,1,1-tri(hydroxymethyl)methyl]pyrazine-2,5-dicarboxamide,
N,N′-bis[1,1,1-tri(hydroxymethyl)methyl]pyrazine-2,6-dicarboxamide,
N-methyl-N-[1,1,1-tri(hydroxymethyl)methyl]-N′-methyl-N′-[1,1,1-tri(hydroxymethyl)methyl]pyrazine-2,5-dicarboxamide,
N-methyl-N-[1,1,1-tri(hydroxymethyl)methyl]-N′-methyl-N′-[1,1,1-tri(hydroxymethyl)methyl]pyrazine-2,6-dicarboxamide,
N,N′-bis[1,1-di(hydroxymethyl)-1-ethyl]pyrazine-2,5-dicarboxamide,
N,N′-bis[1,1-di(hydroxymethyl)-1-ethyl]pyrazine-2,6-dicarboxamide,
N-methyl-N-[1,1-di(hydroxymethyl)-1-ethyl]-N′-methyl-N′-[1,1-di(hydroxymethyl)-1-ethyl]pyrazine-2,5-dicarboxamide,
N-methyl-N-[1,1-di(hydroxymethyl)-1-ethyl]-N′-methyl-N′-[1,1-di(hydroxymethyl)-1-ethyl]pyrazine-2,6-dicarboxamide,
N,N′-bis(2-hydroxyethyl)pyridine-2,5-dicarboxamide,
N,N′-bis(2-hydroxyethyl)pyridine-2,6-dicarboxamide,
N,N′-bis(2-hydroxyethyl)pyridine-3,5-dicarboxamide,
N-methyl-N-(2-hydroxyethyl)-N′-methyl-N′-(2-hydroxyethyl)pyridine-2,5-dicarboxamide,
N-methyl-N-(2-hydroxyethyl)-N′-methyl-N′-(2-hydroxyethyl)pyridine-2,6-dicarboxamide,
N-methyl-N-(2-hydroxyethyl)-N′-methyl-N′-(2-hydroxyethyl)pyridine-3,5-dicarboxamide,
N,N,N′,N′-tetrakis(2-hydroxyethyl)pyridine-2,5-dicarboxamide,
N,N,N′,N′-tetrakis(2-hydroxyethyl)pyridine-2,6-dicarboxamide,
N,N,N′,N′-tetrakis(2-hydroxyethyl)pyridine-3,5-dicarboxamide,
N,N′-bis(2,3-dihydroxy-1-propyl)pyridine-2,5-dicarboxamide,
N,N′-bis(2,3-dihydroxy-1-propyl)pyridine-2,6-dicarboxamide,
N,N′-bis(2,3-dihydroxy-1-propyl)pyridine-3,5-dicarboxamide,
N-methyl-N-(2,3-dihydroxy-1-propyl)-N′-methyl-N′-(2,3-dihydroxy-1-propyl)pyridine-2,5-dicarboxamide,
N-methyl-N-(2,3-dihydroxy-1-propyl)-N′-methyl-N′-(2,3-dihydroxy-1-propyl)pyridine-2,6-

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