Adenosine receptor selective modulators

1. A compound of the formula (I)

in which

R 1 , R 2 and R 3 independently of one another represent (C 1 -C 8 )-alkyl which may be substituted up to three times, independently of one another, by hydroxyl, (C 1 -C 4 )-alkoxy, (C 3 -C 7 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, halogen or (C 6 -C 10 )-aryloxy,

(C 6 -C 10 )-aryl which may be substituted up to three times, independently of one another, by halogen, nitro, (C 1 -C 4 )-alkoxy, carboxyl, (C 1 -C 4 )-alkoxycarbonyl or mono- or di-(C 1 -C 4 )-alkylamino,

(C 1 -C 8 )-alkoxy which may be substituted by hydroxyl, (C 1 -C 4 )-alkoxy, (C 3 -C 7 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 6 -C 10 )-aryl, 5- or 6-membered heteroaryl having up to three heteroatoms from the group consisting of N, O and/or S, (C 6 -C 10 )-aryloxy, halogen, cyano, (C 1 -C 4 )-alkoxycarbonyl, amino or mono- or di-(C 1 -C 4 )-alkylamino,

hydrogen, hydroxyl, halogen, nitro, cyano, or —NH—C(O)—R 7 ,

in which

R 7 represents (C 1 -C 8 )-alkyl which may be substituted by hydroxyl or (C 1 -C 4 )-alkoxy, (C 3 -C 7 )-cycloalkyl or (C 6 -C 10 )-aryl which may be substituted up to three times, independently of one another, by halogen, nitro, (C 1 -C 4 )-alkoxy, carboxyl, (C 1 -C 4 )-alkoxycarbonyl or mono- or di-(C 1 -C 4 )-alkylamino,

or

R 1 and R 2 are attached to adjacent phenyl ring atoms and, together with the two ring carbon atoms, form a 5- to 7-membered saturated or partially unsaturated heterocycle having one or two heteroatoms from the group consisting of N, O and/or S which may be substituted by (C 1 -C 4 )-alkyl or oxo,

R 4 represents (C 1 -C 8 )-alkyl which may be substituted by hydroxyl, —NH—CO—R 8 , (C 1 -C 4 )-alkoxy, (C 3 -C 7 )-cycloalkyl, (C 6 -C 10 )-aryl, 5- or 6-membered saturated or partially unsaturated heterocyclyl having up to three heteroatoms from the group consisting of N, O and/or S or 5- or 6-membered heteroaryl having up to three heteroatoms from the group consisting of N, O and/or S, or (C 3 -C 7 )-cycloalkyl which may be substituted by hydroxyl or (C 1 -C 8 )-alkyl,

in which

R 8 represents (C 1 -C 8 )-alkyl which may be substituted by hydroxyl or (C 1 -C 4 )-alkoxy, (C 3 -C 7 )-cycloalkyl or (C 6 -C 10 )-aryl which may be substituted up to three times, independently of one another, by halogen, nitro, (C 1 -C 4 )-alkoxy, carboxyl, (C 1 -C 4 )-alkoxycarbonyl or mono- or di-(C 1 -C 4 )-alkylamino,

R 5 represents hydrogen or (C 1 -C 4 )-alkyl which may be substituted by hydroxyl, (C 1 -C 4 )-alkoxy or (C 3 -C 7 )-cycloalkyl,

or

R 4 and R 5 together with the nitrogen atom to which they are attached form a 5- to 7-membered saturated or partially unsaturated heterocycle which may contain one or two further heteroatoms from the group consisting of N, O and/or S in the ring and which may be mono- to trisubstituted, independently of one another, by oxo, fluorine, chlorine, bromine, hydroxyl, (C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkoxy,

and

R 6 represents (C 3 -C 7 )-cycloalkyl or (C 1 -C 8 )-alkyl, where alkyl may be substituted up to three times, independently of one another, by (C 3 -C 7 )-cycloalkyl, hydroxyl, —CO—NH—R 9 , (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyl, (C 6 -C 10 )-aryl or 5- to 10-membered heteroaryl having up to three heteroatoms from the group consisting of N, O and/or S,

where

aryl and heteroaryl for their part may be substituted by halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, amino, mono- or di-(C 1 -C 4 )-alkylamino, nitro, cyano or hydroxyl,

and

R 9 represents hydrogen, (C 1 -C 8 )-alkyl which may be substituted by hydroxyl or (C 1 -C 4 )-alkoxy, (C 3 -C 7 )-cycloalkyl or (C 6 -C 10 )-aryl which may be substituted up to three times, independently of one another, by halogen, nitro, (C 1 -C 4 )-alkoxy, carboxyl, (C 1 -C 4 )-alkoxycarbonyl or mono- or di-(C 1 -C 4 )-alkylamino,

or a salt, a hydrate, a hydrate of a salt or a solvate thereof.

2. A compound of the formula (I)

in which

R 1 , R 2 and R 3 independently of one another represent hydrogen, hydroxyl, (C 1 -C 4 )-alkyl, trifluoromethyl, trifluoromethoxy, fluorine, chlorine, (C 1 -C 4 )-alkoxy which may be substituted by hydroxyl, (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyl or (C 3 -C 6 )-cycloalkyl, —NH—C(O)—CH 3 or —NH—C(O)—C 2 H 5 ,

or

R 1 and R 2 are attached to adjacent phenyl ring atoms and represent a group —O—CH 2 —O— or —O—CH 2 —CH 2 —O—,

R 4 represents (C 1 -C 6 )-alkyl which may be substituted by hydroxyl, (C 1 -C 4 )-alkoxy, (C 3 -C 6 )-cycloalkyl, 13 NH—C(O)—CH 3 , phenyl, furyl, pyridyl, imidazolyl, thienyl or hexahydropyranyl, or (C 3 -C 6 )-cycloalkyl,

R 5 represents hydrogen or (C 1 -C 4 )-alkyl which may be substituted by hydroxyl, (C 1 -C 4 )-alkoxy or (C 3 -C 6 )-cycloalkyl,

or

R 4 and R 5 together with the nitrogen atom to which they are attached form a 5- to 7-membered saturated or partially unsaturated heterocycle which may contain a further heteroatom from the group consisting of N, O or S in the ring and which may be mono- to trisubstituted, independently of one another, by hydroxyl, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy,

and

R 6 represents (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkyl which may be substituted up to two times, independently of one another, by (C 3 -C 6 )-cycloalkyl, —CO—NH—R 9 , hydroxyl, (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyl, phenyl or 5- or 6-membered heteroaryl having up to three heteroatoms from the group consisting of N, O and/or S,

where

phenyl and heteroaryl for their part may be substituted by halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, amino, mono- or di-(C 1 -C 4 )-alkylamino, nitro, cyano or hydroxyl,

and

R 9 represents hydrogen or (C 1 -C 4 )-alkyl,

or a salt, a hydrate, a hydrate of a salt or a solvate thereof.

3. A compound of the formula (I)

in which

R 1 and R 2 independently of one another represent hydrogen, 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 or cyclopropyl,

or

R 1 and R 2 are attached to adjacent phenyl ring atoms and represent a group —O—CH 2 —O—,

R 3 represents hydrogen,

R 4 represents methyl, ethyl, n-propyl, isopropyl, where the alkyl radicals for their part may be substituted by hydroxyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, cyclopropyl, —NH—C(O)—CH 3 , furyl, pyridyl, imidazolyl or hexahydropyranyl, or cyclopropyl,

R 5 represents hydrogen or methyl,

or

R 4 and R 5 together with the nitrogen atom to which they are attached represent pyrrolidinyl, morpholinyl, piperidinyl or 4-hydroxypiperidinyl

and

R 6 represents methyl, ethyl or n-propyl, where the alkyl radicals for their part may be substituted up to two times, independently of one another, by hydroxyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, imidazolyl, nitrofuranyl, pyridyl, phenyl which for its part may in turn be substituted by cyano, nitro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or amino, —C(O)—NH 2 or —C(O)—NH—CH 3 ,

or a salt, a hydrate, a hydrate of a salt or a solvate thereof.

4. A process for preparing compounds of the formula (I) as defined in 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 with a compounds of the formula (III)

R 6 —X  (III)

in which

R 6 is as defined in claim 1 and X represents a leaving group.

5. A composition, comprising at least one compounds of the formula (I) as defined in claim 1 and at least one further auxiliary.