Substituted 2, 6-diamino-3, 5-dicyano-4-arylpyridines and their use as adenosine-receptor-selective ligands
View Patent ↗The present invention relates to substituted 2,6-diamino-3,5-dicyano-4-arylpyridines of the formula (I) wherein the definitions of substituent groups R 1 -R 7 are as provided in the specification and claims, to a pharmaceutical composition containing such a compound, to a process for preparation of such materials, and to their use as medicaments for the treatment of cardiovascular disorders and diabetes.
1. A compound of formula (I):
in which
R 1 represents hydrogen, hydroxyl, chlorine, nitro, methyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or —NH—C(O)—CH 3 , where the alkoxy radicals for their part may be substituted by hydroxyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, —O—C(O)—CH 3 or cyclopropyl,
R 2 and R 3 represent hydrogen,
R 4 represents hydrogen, methyl, ethyl, n-propyl or isopropyl, where the alkyl radicals for their part may be substituted by pyridyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or mono- or disubstituted by hydroxyl,
R 5 represents hydrogen,
R 6 represents methyl, ethyl n-propyl, isopropyl, where the alkyl radicals for their part may be mono- or disubstituted, independently of one another, by cyclopropyl, pyridyl, furyl, thienyl, benzimidazolyl, pyrrolidinonyl, N-methylpyrrolidinonyl, N-methylpyrrolidinyl, N-ethylpyrrolidinyl, N-methylimidazolidinonyl, or cyclopropyl
and
R 7 represents hydrogen
or a salt thereof.
2. A process for preparing the compound of claim 1 characterized in that
a compound of the formula (II)
in which
R 1 , R 2 , R 3 , R 4 and R 5 are as defined in claim 1 ,
is reacted in a solvent with a compound of the formula (III)
R 6 —NH—R 7 (III)
in which
R 6 and R 7 are as defined in claim 1 .
3. A pharmaceutical composition, comprising at least one compound of the formula (I) as defined in claim 1 and at least one further auxiliary.
4. The compound of claim 1 , wherein
R 1 represents hydrogen, hydroxyl, chlorine, nitro, methyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, or NH—C(O)—CH 3 , where the alkoxy radicals for their part may be substituted by hydroxyl, or —O—C(O)—CH 3 or cyclopropyl,
R 2 and R 3 represent hydrogen,
R 4 represents hydrogen, methyl, ethyl, n-propyl or isopropyl, where the alkyl radicals for their part may be mono-substituted by hydroxyl,
R 5 represents hydrogen,
R 6 represents methyl, ethyl n-propyl, isopropyl, where the alkyl radicals for their part may be mono- or disubstituted, independently of one another, by cyclopropyl, pyridyl, furyl, thienyl, benzimidazolyl, pyrrolidinonyl, N-methylpyrrolidinonyl, N-methylpyrrolidinyl, N- ethylpyrrolidinyl, N-methylimidazolidinonyl, or cyclopropyl
and
R 7 represents hydrogen
or a salt thereof.
5. The compound of claim 4 , wherein the compound is