Substituted 2-thio-3,5-dicyano-4-aryl-6-aminopyridines and the use thereof

1. A compound of the formula (I)

wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 8 )-alkyl;

optionally substituted (C 6 –C 10 )-aryl;

optionally substituted (C 1 –C 8 )-alkoxy;

—O(CH 2 ) n —CH═CH 2 where n=0, 1 or 2;

halogen;

nitro;

cyano;

—C(O)—R 5 ;

—C(O)—NR 6 R 7 ;

—NR 6 R 7 ;

—NR 6 —C(O)—R 8 ;

—O—C(O)—R 8 ;

—SO 2 —NR 6 R 7 ; and

—NR 6 —SO 2 R 8 ,

where:

R 5 denotes:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 8 )-alkyl;

optionally substituted (C 3 –C 7 )-cycloalkyl;

optionally substituted (C 1 –C 8 )-alkoxy;

optionally substituted (C 6 –C 10 )-aryl;

optionally substituted (C 6 –C 10 )-aryloxy; or

—O—(CH 2 ) n —[(C 6 –C 10 )-aryl] where n=1, 2 or 3,

where the (C 6 –C 10 )-aryl group may be fused via two adjacent ring atoms to optionally substituted (C 4 –C 7 )-cycloalkyl,

or

R 5 represents a 5- to 7-membered saturated or unsaturated heterocycle which may be mono- or polysubstituted by

an oxo group (═O);

halogen;

optionally substituted (C 1 –C 8 )-alkyl;

nitro;

cyano;

hydroxyl;

optionally substituted (C 6 –C 10 )-aryl; or

by (C 1 –C 8 -alkoxy,

or

R 5 represents optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted (C 6 –C 10 )-aryl or optionally substituted (C 4 –C 7 )-cycloalkyl,

and

R 6 and R 7 are identical or different and represent

hydrogen;

optionally substituted (C 1 –C 8 )-alkyl;

optionally substituted (C 6 –C 10 )-aryl; or

represent optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S

or

R 6 and R 7 together with the nitrogen atom to which they are optionally attached form a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of

an oxo group (═O);

halogen;

(C 1 –C 8 )-alkyl;

cyano;

hydroxyl;

(C 6 –C 10 )-aryl; and

(C 1 –C 8 )-alkoxy,

and

R 8 represents hydroxyl;

NR 6 R 7 where R 6 and R 7 are as defined above;

optionally substituted (C 1 –C 8 )-alkyl;

(C 1 –C 8 )-alkoxy;

optionally substituted (C 6 –C 10 )-aryl;

(C 6 –C 10 )-aryloxy; or

—O—(CH 2 ) n —[(C 6 –C 10 )-aryl] where n=1, 2 or 3,

and

R 4 represents straight-chain or branched (C 1 –C 8 )-alkyl or (C 2 –C 8 alkenyl which are optionally mono- or polysubstituted by

optionally substituted (C 6 –C 10 )-aryloxy;

optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S;

optionally substituted (C 6 –C 10 )-aryl; or

by a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of an oxo group (═O); halogen; (C 1 –C 8 )alkyl; nitro; cyano; hydroxyl; (C 6 –C 10 )-aryl; and or by (C 1 –C 8 )-alkoxy,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted (C 6 –C 10 )-aryl,

or a tautomer, salt, hydrate, or alkoxide thereof,

except for the following compounds of the formula (I), in which the radicals R 1 , R 2 , R 3 and R 4 are as defined below:

R 1 ═R 2 ═H; R 3 =para-OH; R 4 ═—CH_—Z where Z═CN, C(O)—OC 2 H 5 , 4-Br—C 6 H 4 —CO, 4-n-butyl-C 6 H 4 —CO, H, C 6 H 5 , C(O)—O—CH 2 —C 6 H 5 , C(O)—OCH 3 , C(O)—OH, 2-oxo-benzo-pyranyl-3-carbonyl, 4-Cl—C 6 H 4 —CO, 3-Br—C 6 H 4 —CO, 4-C 6 H 5 —C 6 H 4 —CO, 4-CH 3 —C 6 H 4 —CO, 3,4-Cl 2 —C 6 H 3 —CO, or C(O)—NH 2 ;

R 1 ═R 2 ═H; R 3 =meta-OH; R 4 ═—CH 2 —Z where Z═4-Br—C 6 H 4 —NH—CO, 2-oxo-benzo-pyranyl-3-carbonyl, 4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =para-O—C(O)—CH 3 ; R 4 ═—CH 2 —Z where Z═4-CH 3 —C 6 H 4 —CO, H, 2-oxo-benzopyranyl-3-carbonyl, (CH 2 ) 3 —CH 3 , 4-C 6 H 5 —C 6 H 4 , (CH 2 ) 4 —CH 3 , CH 3 , or 2-CH 3 —C 6 H 4 ;

R 1 ═R 2 ═R 3 ═H; R 4 ═—CH 2 —Z where Z═CH 3 , CN, 2-naphthyl, 4-Br—C 6 H 4 —CO, C(O)—OCH 3 , C(O)—OCH 2 —CH 5 , H, C(O)—C 6 H 5 , or 4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =para-butoxy; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 5 , C(O)—OCH 3 , C(O)—C 6 H 5 , CH═CH 2 , C(O)—NH 2 , H, 4-Br—C 6 H 4 —CO, 4-Cl—C 6 H 4 —CO, C(O)—OC 2 H 5 , C(O)—O—CH 2 —C 6 H 5 , 2-oxo-benzopyranyl-3-carbonyl, C(O)—NH—C 6 H 5 , CN;

R 1 ═R 2 ═H; R 3 =para-bromo; R 4 ═—CH 2 —Z where Z=4-Br—C 6 H 4 —CO, 4-Cl—C 6 H 4 —CO, C(O)—NH 2 , C(O)—OCH 3 , 4-Cl—C 6 H 5 , 4-Br—C 6 H 4 —NH—CO;

R 1 ═R 2 ═H; R 3 =meta-fluoro; R 4 ═—CH 2 —Z where Z=4-Br—C 6 H 4 —CO, C(O)—NH 2 , C(O)—O—CH 2 —C 6 H 5 , CN;

R 1 ═R 2 ═H; R 3 =para-chloro; R 4 ═—CH 2 —Z where Z=2-naphthyl, CH 3 , 4-Cl—C 6 H 4 —CO, or C 6 H 5 —CO;

R 1 ═R 2 ═H; R 3 =para-OCH 3 ; R 4 ═—CH 2 —Z where Z=2-naphthyl, CH 3 ;

R 1 ═R 2 ═H; R 3 =meta-NO 2 ; R 4 =—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 ═H; R 3 =ortho-OCH 3 ; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =ortho-chloro; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 4 —CO, C 6 H 5 —CO, or CH═CH 2 ;

R 1 ═R 2 ═H; R 3 =ortho-iodo; R 4 ═—CH 2 —Z where Z═CH═CH 2 .

2. The compound of the formula (I) as claimed in claim 1 , wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 6 )-alkyl;

optionally substituted phenyl or naphthyl;

optionally substituted (C 1 –C 6 )-alkoxy;

—O—(CH 2 ) n —CH═CH 2 where n=1 or 2;

fluorine, chlorine, bromine;

nitro;

cyano;

—C(O)—R 5 ;

—C(O)—NR 6 R 7 ;

—NR 6 R 7 ;

—NR 6 —C(O)—R 8 ;

—O—C(O)—R 8 ;

—SO 2 —NR 6 R 7 ; and

—NR 6 —SO 2 R 8 ,

where:

R 5 denotes:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 6 )-alkyl;

optionally substituted (C 3 –C 7 )-cycloalkyl;

optionally substituted (C 1 –C 6 )-alkoxy;

optionally substituted phenyl or naphthyl;

optionally substituted phenyloxy or naphthyloxy; or

—O—(CH 2 ) n -phenyl where n=1, 2 or 3,

where the phenyl or naphthyl group may be fused via two adjacent ring atoms to optionally substituted (C 4 –C 7 )-cycloalkyl,

or

R 5 represents a 5- to 7-membered saturated or unsaturated heterocycle which may be mono- or polysubstituted by

an oxo group (═O);

fluorine, chlorine, bromine;

optionally substituted (C 1 –C 6 )-alkyl;

nitro;

cyano;

hydroxyl;

optionally substituted phenyl or naphthyl; or

by (C 1 –C 6 )-alkoxy,

or

R 5 represents optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted phenyl or naphthyl or optionally substituted (C 4 –C 7 )-cycloalkyl,

and

R 6 and R 7 are identical or different and represent

hydrogen;

optionally substituted (C 1 –C 6 )-alkyl;

optionally substituted phenyl or naphthyl; or

represent optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S

or

R 6 and R 7 together with the nitrogen atom to which they are optionally attached form a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of

an oxo group (═O);

fluorine, chlorine, bromine;

(C 1 –C 6 )-alkyl;

nitro;

cyano;

hydroxyl;

phenyl or naphthyl; and

(C 1 –C 6 )-alkoxy,

and

R 8 represents NR 6 R 7 where R 6 and R 7 are as defined above;

optionally substituted (C 1 –C 6 )-alkyl;

(C 1 –C 6 )-alkoxy;

optionally substituted phenyl or naphthyl;

phenyloxy or naphthyloxy; or

—O—(CH 2 ) n -phenyl where n=1, 2 or 3,

and

R 4 represents straight chain or branched (C 1 –C 6 )-alkyl or (C 2 –C 6 )-alkenyl which are optionally mono- or polysubstituted by

optionally substituted phenyloxy or naphthyloxy;

optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S;

optionally substituted phenyl or naphthyl; or

by a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of an oxo group (═O); fluorine, chlorine, bromine; (C 1 –C 6 )-alkyl; nitro; cyano; hydroxyl; phenyl or naphthyl; or by (C 1 –C 6 )-alkoxy,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted phenyl or naphthyl,

or a tautomer, salt, hydrate, or alkoxide thereof,

except for the following compounds of the formula (I), in which the radicals R 1 , R 2 , R 3 and R 4 are as defined below:

R 1 ═R 2 ═H; R 3 =para-OH; R 4 ═—CH 2 —Z where Z═CN, C(O)—OC 2 H 5 , 4-Br—C 6 H 4 —CO, 4-n-butyl-C 6 H 4 —CO, H, C 6 H 5 , C(O)—O—CH 2 —C 6 H 5 , C(O)—OCH 3 , C(O)—OH, 2-oxo-benzo-pyranyl-3-carbonyl, 4-Cl—C 6 H 4 —CO, 3-Br—C 6 H 4 —CO, 4-C 6 H 5 —C 6 H 4 —CO, 4-CH 3 —C 6 H 4 —CO, 3,4-Cl 2 —C 6 H 3 —CO, C(O)—NH 2 ;

R 1 ═R 2 ═H; R 3 =meta-OH; R 4 ═—CH 2 —Z where Z=4-Br—C 6 H 4 —NH—CO, 2-oxo-benzo-pyranyl-3-carbonyl, 4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =para-O—C(O)—CH 3 ; R 4 ═—CH 2 —Z where Z=4-CH 3 —C 6 H 4 —CO, H, 2-oxo-benzopyranyl-3-carbonyl, (CH 2 ) 3 —CH 3 , 4-C 6 H 5 —C 6 H 4 , (CH 2 ) 4 —CH 3 , CH 3 , 2-CH 3 —C 6 H 4 ;

R 1 ═R 2 ═R 3 ═H; R 4 ═—CH 2 —Z where Z═CH 3 , CN, 2-naphthyl, 4-Br—C 6 H 4 —CO, C(O)—OCH 3 , C(O)—OCH 2 —C 6 H 5 , H, C(O)—C 6 H 5 , 4-Cl—C 6 H 4 —CO;

R 1 ═R 2 =H; R 3 =para-butoxy; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 5 , C(O)—OCH 3 , C(O)—C 6 H 5 , CH═CH 2 , C(O)—NH 2 , H, 4-Br—C 6 H 4 —CO, 4-Cl—C 6 H 4 —CO, C(O)—OC 3 H 5 , C(O)—O—CH 2 —CH 5 , 2-oxo-benzopyranyl-3-carbonyl, C(O)—NH—C 6 H 5 , CN;

R 1 ═R 2 ═H; R 3 =para-bromo; R 4 ═—CH 2 —Z where Z=4-Br—C 6 H 4 —CO, 4-Cl—C 6 H 4 —CO, C(O)—NH 2 , C(O)—OCH 3 , 4-Cl—C 6 H 5 , 4-Br—C 6 H 4 —NH—CO;

R 1 ═R 2 ═H; R 3 =meta-fluoro; R 4 ═—CH 2 —Z where Z=4-Br—C 6 H 4 —CO, C(O)—NH 2 , C(O)—O—CH 2 —C 6 H 5 , CN;

R 1 ═R 2 ═H; R 3 =para-chloro; R 4 ═—CH 2 —Z where Z=2-naphthyl, CH 3 , 4-Cl—C 6 H 4 —CO, C 6 H 5 —CO;

R 1 ═R 2 ═H; R 3 =para-OCH 3 ; R 4 ═—CH 2 —Z where Z=2-naphthyl, CH 3 ;

R 1 ═R 2 H; R 3 =meta-NO 2 ; R 4 ═—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 ═H; R 3 =ortho-OCH 3 ; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =ortho-chloro; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 4 —CO, C 6 H 5 —CO, or CH═CH 2 .

3. The compound of the formula (I) as claimed in claim 1 , wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 4 )-alkyl;

optionally substituted phenyl;

optionally substituted (C 1 –C 4 )-alkoxy;

—O—(CH 2 ) n —CH═CH 2 where n=1;

fluorine, chlorine;

nitro;

cyano;

—C(O)—R 5 ;

—C(O)—NR 6 R 7 ;

—N 6 R 7 ;

—NR 6 —C(O)—R 8 ;

—O—C(O)—R 8 ;

—SO 2 —NR 6 R 7 ; and

where:

R 5 denotes:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 4 )-alkyl;

optionally substituted (C 3 –C 7 )-cycloalkyl;

optionally substituted (C 1 –C 4 )-alkoxy;

optionally substituted phenyl;

optionally substituted phenyloxy; or

—O—(CH 2 ) n -phenyl where n=1,

where the phenyl group may be fused via two adjacent ring atoms to optionally substituted (C 5 –C 6 )-cycloalkyl,

or

R 5 represents a 5- to 7-membered saturated or unsaturated heterocycle which for its part may be mono- or polysubstituted by

an oxo group (═O);

fluorine, chlorine;

optionally substituted (C 1 –C 4 )-alkyl;

nitro;

cyano;

hydroxyl;

optionally substituted phenyl; or

by (C 1 –C 4 )-alkoxy,

or

R 5 represents optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S, selected from the group consisting of furanyl, pyrrolyl, thienyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, pyridyl, pyrimidyl and pyridazinyl,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted phenyl or optionally substituted (C 5 –C 6 )-cycloalkyl,

and

R 6 and R 7 are identical or different and represent

hydrogen;

optionally substituted (C 1 –C 4 )-alkyl;

optionally substituted phenyl; or

represent optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S selected from the group consisting of furanyl, pyrrolyl, thienyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, pyridyl, pyrimidyl and pyridazinyl,

or

R 6 and R 7 together with the nitrogen atom to which they are optionally attached form a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of

an oxo group (═O);

fluorine, chlorine;

(C 1 –C 4 )-alkyl;

nitro;

cyano;

hydroxyl;

phenyl; and

(C 1 –C 4 )-alkoxy,

and

R 8 represents NR 6 R 7 where R 6 and R 7 are as defined above;

optionally substituted (C 1 –C 4 )-alkyl;

(C 1 –C 4 )-alkoxy;

optionally substituted phenyl;

phenyloxy; or

—O—(CH 2 ) n -phenyl where n=1,

and

R 4 represents straight-chain or branched (C 1 –C 4 )-alkyl or (C 2 –C 4 )-alkenyl which are optionally mono- or polysubstituted by

optionally substituted phenyloxy;

optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S selected from the group consisting of furanyl, pyrrolyl, thienyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, pyridyl pyrimidyl and pyridazinyl;

optionally substituted phenyl; or

by a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of an oxo group (═O); fluorine, chlorine; (C 1 –C 4 )-alkyl; nitro; cyano; hydroxyl; phenyl; or by (C 1 –C 4 )-alkoxy,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent rings atoms to optionally substituted phenyl,

or a tautomer, salt, hydrate, or alkoxide thereof,

except for the following compounds of the formula (I), in which the radicals R 1 , R 2 , R 3 and R 4 are as defined below:

R 1 ═R 2 ═H; R 3 =para-OH; R 4 ═—CH 2 —Z where Z═CN, C(O)—OC 2 H 5 , 4-Br—C 6 H 4 —CO, 4-n-butyl-C 6 H 4 —CO, H, C 6 H 5 , C(O)—O—CH 2 —C 6 H 5 , C(O)—OCH 3 , C(O)—OH, 2-oxo-benzo-pyranyl-3-carbonyl, 4-Cl—C 6 H 4 —CO, 3-Br—C 6 H 4 —CO, 4-C 6 H 5 —C 6 H 4 —CO, 4-CH 3 —C 6 H 4 —CO, 3,4-Cl 2 —C 6 H 3 —CO, or C(O)—NH 2 ;

R 1 ═R 2 ═H; R 3 =meta-OH; R 4 ═—CH 2 —Z where Z=4-Br—C 6 H 4 —NH—CO, 2-oxo-benzo-pyranyl-3-carbonyl, 4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =para-O—C(O)—CH 3 ; R 4 ═—CH 2 —Z where Z=4-CH 3 —C 6 H 4 —CO, H, 2-oxo-benzopyranyl-3-carbonyl, 4-C 6 H 5 —C 6 H 4 , CH 3 , 2-CH 3 —C 6 H 4 ;

R 1 ═R 2 ═R 3 ═H; R 4 ═—CH 2 —Z where Z═CH 3 , CN, 4-Br—C 6 H 4 —CO, C(O)—OCH 3 , C(O)—OCH 2 —C 6 H 5 , H, C(O)—C 6 H 5 , 4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =para-butoxy; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 5 , C(O)—OCH 3 , C(O)—C 6 H 5 , CH═CH 2 , C(O)—NH 2 , H, 4-Br—C 6 H 4 —CO, 4-Cl—C 6 H 4 —CO, C(O) —OC 2 H 5 , C(O)—O—CH 2 —C 6 H 5 , 2-oxo-benzopyranyl-3-carbonyl, C(O)—NH—C 6 H 5 , CN;

R 1 ═R 2 ═H; R 3 =meta-fluoro; R 4 ═—CH 2 —Z where Z=4-Br—C 6 H 4 —CO, C(O)—NH 2 , C(O)—O—CH 2 —C 6 H 5 , CN;

R 1 ═R 2 ═H; R 3 para-chloro; R 4 ═—CH 2 —Z where Z═CH 3 , 4-Cl—C 6 H 4 —CO, or C 6 H 5 —CO;

R 1 ═R 2 ═H; R 3 =para-OCH 3 ; R 4 ═—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 ═H; R 3 =meta-NO 2 ; R 4 ═—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 ═H; R 3 =ortho-OCH 3 ; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 4 —CO;

R 1 ═R 2 ═H; R 3 =ortho-chloro; R 4 ═—CH 2 —Z where Z=4-Cl—C 6 H 4 —CO, C 6 H 5 —CO, or CH═CH 2 .

4. The compound of the formula (I) as claimed in any of claims 1 to 3 , wherein

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

methyl;

trifluoromethyl;

methoxy;

radicals of the formulae —O—CH 2 —CH 2 —OH, —O—CH 2 —COOH or —O—CH 2 —CH═CH 2 ;

fluorine, chlorine or bromine;

nitro;

cyano;

—C(O)OH or C(O)OCH 3 ;

—C(O)NH 2 ;

—NH 2 ;

—NH—C(O)—CH 3 ;

—O—C(O)—CH 3 or —O—C(O)—C 2 H 5 ;

radicals of the formulae

 or

and

—NH—SO 2 CH 3 or —NH—SO 2 C 6 H 5 ,

and

R 4 represents straight-chain or branched (C 1 –C 4 )-alkyl which is optionally mono- or polysubstituted by

phenyl, which may be substituted by nitro, cyano, fluorine, methoxy, difluoromethoxy, methoxycarbonyl or p-tolylsulfonylmethyl;

pyridyl, furyl, imidazolyl, benzimidazolyl or thiazolyl, which may in each case be mono- or disubstituted by identical or different substituents from the group consisting of methyl, nitro and chlorine;

oxadiazolyl which may be substituted by phenyl or methoxyphenyl;

or

a radical of the formula

or a tautomer, salt, hydrate, or alkoxide thereof,

except for the following compounds of the formula (I), in which the radicals R 1 , R 2 , R 3 and R 4 are as defined below:

R 1 ═R 2 ═H; R 3 =para-H; R 4 ═—CH 2 —Z where Z═H, C 6 H 5 , C(O)—OCH 3 , or C(O)—NH 2 ;

R 1 ═R 2 ═H; R 3 =para-O—C(O)—CH 3 ; R 4 ═—CH 2 —Z where Z═H, or CH 3 ;

R 1 ═R 2 ═R 3 ═H; R 4 ═—CH 2 —Z where Z═CH 3 , or C(O)—OCH 3 ;

R 1 ═R 2 ═H; R 3 =meta-fluoro; R 4 ═—CH 2 —Z where Z═C(O)—NH 2 ;

R 1 ═R 2 ═H; R 3 =para-chloro; R 4 ═—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 ═H; R 3 =para-OCH 3 ; R 4 ═—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 ═H; R 3 =meta-NO 2 ; R 4 ═—CH 2 —Z where Z═CH 3 .

5. The compound of the formula (I) as claimed in any of claims 1 to 3 , wherein

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

methyl;

methoxy;

radicals of the formulae —O—CH 2 —CH 2 —OH, —O—CH 2 —COOH or —O—CH 2 CH═CH 2 ;

fluorine or chlorine;

nitro;

cyano;

—C(O)OH or —C(O)OCH 3 ;

—C(O)NH 2 ;

—NH 2 ;

—NH—C(O)CH 3 ;

—O—C(O)—CH 3 or —O—C(O)—C 2 H 5 ;

radicals of the formulae

 or

and

—NH—SO 2 CH 3 or —NH—SO 2 C 6 H 5 ,

and

R 4 represents straight-chain or branched (C 1 –C 4 )-alkyl which is optionally mono- or polysubstituted by

phenyl;

ortho-nitrophenyl; or

a radical of the formula

 or

or a tautomer, salt, hydrate, or alkoxide thereof,

except for the following compounds of the formula (I), in which the radicals R 1 , R 2 , R 3 and R 4 are as defined below:

R 1 ═R 2 ═H; R 3 =para-OH; R 4 ═—CH 2 —Z where Z═H, C 6 H 5 , C(O)—OCH 3 , or C(O)—NH 2 ;

R 1 ═R 2 ═H; R 3 =para-O—C(O)—CH 3 ; R 4 ═—CH 2 —Z where Z═H, or CH 3 ;

R 1 ═R 2 ═R 3 ═H; R 4 ═—CH 2 —Z where Z═CH 3 , or C(O)—OCH 3 ;

R 1 ═R 2 ═H; R 3 =meta-fluoro; R 4 ═—CH 2 —Z where Z═C(O)—NH 2 ;

R 1 ═R 2 ═H; R 3 =para-chloro; R 4 ═—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 H; R 3 =para-OCH 3 ; R 4 ═—CH 2 —Z where Z═CH 3 ;

R 1 ═R 2 ═H; R 3 =meta-NO 2 ; R 4 ═—CH 2 —Z where Z═CH 3 .

6. A process for preparing the compounds of the formula (I) as claimed in claim 1 ,

wherein:

a compound of the formula (II)

in which the radicals R 1 , R 2 and R 3 are as defined above in claim 1 ,

is reacted with a compound of the formula (III)

R 4 —X  (III),

in which R 4 is as defined above in claim 1

and

X represents a nucleofugic group,

in an inert solvent, if appropriate in the presence of a base.

7. The process of claim 6 wherein said nucleofugic group is selected from the group consisting of halogen, mesylate, tosylate, triflate, and 1-imidazolyl.

8. The process of claim 7 wherein said halogen is selected from the group consisting of chlorine, bromine, and iodine.

9. A method of treating a cardiovascular disorder comprising administering to a host in need thereof an effective amount of a compound of the formula (I)

wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 8 )-alkyl;

optionally substituted (C 6 –C 10 )-aryl;

optionally substituted (C 1 –C 8 )-alkoxy;

—O—(CH 2 ) n —CH═CH 2 where n=0, 1 or 2;

halogen;

nitro;

cyano;

—C(O)—R 5 ;

—C(O)—NR 6 R 7 ;

—NR 6 R 7 ;

—NR 6 —C(O)—R 8 ;

—O—C(O)—R 8 ;

—SO 2 —NR 6 R 7 ; and

—NR 6 —SO 2 R 8 ,

where:

R 5 denotes:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 8 )-alkyl;

optionally substituted (C 3 –C 7 )-cycloalkyl;

optionally substituted (C 1 –C 8 )-alkoxy;

optionally substituted (C 6 –C 10 )-aryl;

optionally substituted (C 6 –C 10 )-aryloxy; or

—O—(CH 2 ) n —[(C 6 –C 10 )-aryl] where n=1, 2 or 3,

where the (C 6 –C 10 )-aryl group may be fused via two adjacent ring atoms to optionally substituted (C 4 –C 7 )-cycloalkyl,

or

R 5 represents a 5- to 7-membered saturated or unsaturated heterocycle which may be mono- or polysubstituted by

an oxo group (═O);

halogen;

optionally substituted (C 1 –C 8 )-alkyl:

nitro;

cyano;

hydroxyl;

optionally substituted (C 6 –C 10 )-aryl; or

by (C 1 –C 8 )-alkoxy,

or

R 5 represents optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted (C 6 –C 10 )-aryl or optionally substituted (C 4 –C 7 )-cycloalkyl,

and

R 6 and R 7 are identical or different and represent

hydrogen;

optionally substituted (C 1 –C 8 )-alkyl;

optionally substituted (C 6 –C 10 )-aryl; or

represent optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S

or

R 6 and R 7 together with the nitrogen atom to which they are optionally attached form a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of

an oxo group (═O);

halogen;

(C 1 –C 8 )-alkyl;

nitro;

cyano;

hydroxyl;

(C 6 –C 10 )-alkyl; and

(C 1 –C 8 )-alkoxy,

and

R 8 represents hydroxyl;

NR 6 R 7 where R 6 and R 7 are as defined above;

optionally substituted (C 1 –C 8 )-alkyl;

(C 1 –C 8 )-alkoxy;

optionally substituted (C 6 –C 10 )-aryl;

(C 6 –C 10 )-aryloxy; or

—O—(CH 2 ) n —[(C 6 –C 10 )-aryl] where n=1, 2 or 3,

and

R 4 represents straight-chain or branched (C 1 –C 8 )-alkyl or (C 2 –C 8 )-alkenyl which are optionally mono- or polysubstituted by

optionally substituted (C 6 –C 10 )-aryloxy;

optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S;

optionally substituted (C 6 –C 10 )-aryl; or

by a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of an oxo group (═O); halogen; (C 1 –C 8 )-alkyl; nitro; cyano: hydroxyl; (C 6 –C 10 )-aryl; or by (C 1 –C 8 )-alkoxy,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted (C 6 –C 10 )-aryl,

or a tautomer, salt, hydrate, or alkoxide thereof.

10. A method of treating a cardiovascular disorder comprising administering to a host in need thereof an effective amount of the compound of the formula (I) as claimed in claim 9 ,

wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 6 )-alkyl;

optionally substituted phenyl or naphthyl;

optionally substituted (C 1 –C 6 )-alkoxy;

—O—(CH 2 ) n —CH═CH 2 where n=1 or 2;

fluorine, chlorine, bromine;

nitro;

cyano;

—C(O)—R 5 ;

—C(O)—NR 6 R 7 ;

—NR 6 R 7 ;

—NR 6 —C(O)—R 8 ;

—O—C(O)—R 8 ;

—SO 2 —NR 6 R 7 ; and

—NR 6 —SO 2 R 8 ,

where:

R 5 denotes:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 6 )-alkyl;

optionally substituted (C 3 –C 7 )-cycloalkyl;

optionally substituted (C 1 –C 6 )-alkoxy;

optionally substituted phenyl or naphthyl;

optionally substituted phenyloxy or naphthyloxy; or

—O—(CH 2 ) n -phenyl where n=1, 2 or 3,

where the phenyl or naphthyl group may be fused via two adjacent ring atoms to optionally substituted (C 4 –C 7 )-cycloalkyl,

or

R 5 represents a 5- to 7-membered saturated or unsaturated heterocycle which may be mono- or polysubstituted by

an oxo group (═O);

fluorine, chlorine, bromine;

optionally substituted (C 1 –C 6 )-alkyl;

nitro;

cyano;

hydroxyl;

optionally substituted phenyl or naphthyl; or

by (C 1 –C 6 )-alkoxy,

or

R 5 represents optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted phenyl or naphthyl or optionally substituted (C 4 –C 7 )-cycloalkyl,

and

R 6 and R 7 are identical or different and represent

hydrogen;

optionally substituted (C 1 –C 6 )-alkyl;

optionally substituted phenyl or naphthyl; or

represent optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S

or

R 6 and R 7 together with the nitrogen atom to which they are optionally attached form a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of

an oxo group (═O);

fluorine, chlorine, bromine;

(C 1 –C 6 )-alkyl;

nitro;

cyano;

hydroxyl;

phenyl or naphthyl; and

(C 1 —C 6 )-alkoxy,

and

R 8 represents NR 6 R 7 where R 6 and R 7 are as defined above;

optionally substituted (C 1 –C 6 )-alkyl;

(C 1 –C 6 )-alkoxy;

optionally substituted phenyl or naphthyl;

phenyloxy or naphthyloxy; or

—O—(CH 2 ) n -phenyl where n=1, 2 or 3,

and

R 4 represents straight-chain or branched (C 1 –C 6 )-alkyl or (C 2 –C 6 )-alkenyl which are optionally mono- or polysubstituted by

optionally substituted phenyloxy or naphthyloxy;

optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S;

optionally substituted phenyl or naphthyl; or

by a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of an oxo group (═O); fluorine, chlorine, bromine; (C 1 –C 6 )-alkyl; nitro; cyano; hydroxyl; phenyl or naphthyl; or by (C 1 –C 6 )-alkoxy,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted phenyl or naphthyl,

or a tautomer, salt, hydrate, or alkoxide thereof.

11. A method of treating cardiovascular disorder comprising administering to a host in need thereof an effective amount of the compound of the formula (I) as claimed in claim 10 ,

wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 4 )-alkyl;

optionally substituted phenyl;

optionally substituted (C 1 –C 4 )-alkoxy;

—O—(CH 2 ) n —CH═CH 2 where n=1;

fluorine, chlorine;

nitro;

cyano;

—C(O)—R 5 ;

—C(O)—NR 6 R 7 ;

—NR 6 R 7 ;

—NR 6 —C(O)—R 8 ;

—O—(O)—R 8 ;

—SO 2 —NR 6 R 7 ; and

—NR 6 —SO 2 R 8 ,

where:

R 5 denotes:

hydrogen;

hydroxyl;

optionally substituted (C 1 –C 4 )-alkyl;

optionally substituted (C 3 –C 7 )-cycloalkyl;

optionally substituted (C 1 –C 4 )-alkoxy;

optionally substituted phenyl;

optionally substituted phenyloxy; or

—O—(CH 2 ) n -phenyl where n=1,

where the phenyl group may be fused via two adjacent ring atoms to optionally substituted (C 5 –C 6 )-cycloalkyl,

or

R 5 represents a 5- to 7-membered saturated or unsaturated heterocycle which may be mono- or polysubstituted by

an oxo group (═O);

fluorine, chlorine;

optionally substituted (C 1 –C 4 alkyl;

nitro;

cyano;

hydroxyl;

optionally substituted phenyl; or

by (C 1 –C 4 )-alkoxy,

or

R 5 represents optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S, selected from the group consisting of furanyl, pyrrolyl, thienyl, thiazolyl, oxazolyl, imidazolyl triazolyl, pyridyl, pyrimidyl and pyridazinyl,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent ring atoms to optionally substituted phenyl or optionally substituted (C 5 –C 6 )-cycloalkyl,

and

R 6 and R 7 are identical or different and represent

hydrogen;

optionally substituted (C 1 –C 4 )-alkyl;

optionally substituted phenyl; or

represent optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S selected from the group consisting of furanyl, pyrrolyl, thienyl thiazolyl, oxazolyl, imidazolyl, triazolyl, pyridyl, pyrimidyl and pyridazinyl,

or

R 6 and R 7 together with the nitrogen atom to which they are optionally attached form a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of

an oxo group (═O);

fluorine, chlorine;

(C 1 –C 4 )-alkyl;

nitro;

cyano;

hydroxyl;

phenyl; and

(C 1 –C 4 )-alkoxy,

and

R 8 represents NR 6 R 7 where R 6 and R 7 are as defined above;

optionally substituted (C 1 –C 4 )-alkyl;

(C 1 –C 4 )-alkoxy;

optionally substituted phenyl;

phenyloxy; or

—O—(CH 2 ) n -phenyl where n=1,

and

R 4 represents straight-chain or branched (C 1 –C 4 )-alkyl or (C 2 –C 4 )-alkenyl which are optionally mono- or polysubstituted by

optionally substituted phenyloxy;

optionally substituted 5- to 6-membered heteroaryl having up to 3 heteroatoms from the group consisting of N, O and S selected from the group consisting of furanyl, pyrrolyl, thienyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, pyridyl, pyrimidyl and pyridazinyl;

optionally substituted phenyl; or

by a 5- to 7-membered saturated or unsaturated heterocycle having up to 3 heteroatoms from the group consisting of N, O and S, which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of an oxo group (═O); fluorine, chlorine; (C 1 –C 4 )-alkyl; nitro; cyano; hydroxyl; phenyl; or by (C 1 –C 4 )-alkoxy,

where the heterocycle and the heteroaryl ring may each optionally be fused via two adjacent rings atoms to optionally substituted phenyl,

or a tautomer, salt, hydrate, or alkoxide thereof.

12. A method of treating a cardiovascular disorder comprising administering to a host in need thereof an effective amount of the compound of the formula (I) as claimed in claim 11 , wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

methyl;

trifluoromethyl;

methoxy;

radicals of the formulae —O—CH 2 —CH 2 —OH, —O—CH 2 —COOH or —O—CH 2 —CH═CH 2 ;

fluorine, chlorine or bromine;

nitro;

cyano;

—C(O)OH or —C(O)OCH 3 ;

—C(O)NH 2 ;

—NH 2 ;

—NH—C(O)—CH 3 ;

—O—C(O)—CH 3 or —O—C(O)—C 2 H 5 ;

radicals of the formulae

 or

and

—NH—SO 2 CH 3 or —NH—SO 2 C 6 H 5 ,

and

R 4 represents straight-chain or branched (C 1 –C 4 )-alkyl which is optionally mono- or polysubstituted by

phenyl, which may be substituted by nitro, cyano, fluorine, methoxy, difluoromethoxy, methoxycarbonyl or p-tolylsulfonylmethyl;

pyridyl, furyl, imidazolyl, benzimidazolyl or thiazolyl, which may in each case be mono- or disubstituted by identical or different substituents from the group consisting of methyl, nitro and chlorine;

oxadiazolyl which may be substituted by phenyl or methoxyphenyl;

or

a radical of the formula

or a tautomer, salt, hydrate, or alkoxide thereof.

13. A method of treating a cardiovascular disorder comprising administering to a host in need thereof an effective amount of the compound of the formula (I) as claimed in claim 12 , wherein:

R 1 , R 2 , R 3 are identical or different and independently of one another are selected from the group consisting of the following substituents:

hydrogen;

hydroxyl;

methyl;

methoxy;

radicals of the formulae —O—CH 2 —CH 2 —OH, —O—CH 2 —COOH or —CH 2 —CH═CH 2 ;

fluorine or chlorine;

nitro;

cyano;

—C(O)OH or —C(O)OCH 3 ;

—C(O)NH 2 ;

—NH 2 ;

—NH—C(O)CH 3 ;

—O—C(O)—CH 3 or —O—C(O)—C 2 H 5 ;

radicals of the formulae

 or

and

—NH—SO 2 CH 3 or —NH—SO 2 C 6 H 5 ,

and

R 4 represents straight-chain or branched (C 1 –C 4 )-alkyl which is optionally mono- or polysubstituted by

phenyl;

ortho-nitrophenyl; or

a radical of the formula

 or

or a tautomer, salt, hydrate, or alkoxide thereof.

14. A pharmaceutical composition, comprising at least one compound of the formula (I) as defined in claim 1 plus a pharmaceutically acceptable carrier or excipient.

15. A pharmaceutical composition, comprising at least one selective adenosine receptor ligand of claim 1 selected from the group consisting of an adenosine A1 receptor ligand, adenosine A2a receptor ligand and adenosine A2b receptor ligand, plus a pharmaceutically acceptable carrier or excipient.

16. A method of treating a cardiovascular disorder comprising administering to a host in need thereof an effective amount of a pharmaceutical composition as claimed in claim 14 or 15 .

17. A method of treating a cardiovascular disorder comprising administering to a host in need thereof an effective amount of a selective adenosine receptor ligand of claim 1 selected from the group consisting of adenosine A1 receptor ligand, adenosine A2a receptor ligand, and adenosine A2b receptor ligand.