Halogen-substituted amino dicarboxylic acid derivatives as medicaments for treating cardiovascular diseases

1. A compound of the general formula (I)

wherein

R 1 is located in the meta- or para-position to the ethylamino radical and represents halogen;

R 2 represents H or halogen;

R 3 represents H or halogen;

R 4 represents C 3-8 -cycloalkyl or phenyl, where the phenyl radical may additionally carry a substituent from the group consisting of halogen, CN, OMe, CF 3 ;

with the proviso that R 4 does not represent phenyl which carries a substituent CF 3 or OMe in the para-position to the point of attachment if, simultaneously, R 1 is in the meta-position to the ethylamino radical and represents F and R 2 and R 3 each represent H;

or a pharmaceutically acceptable salt or stereoisomer thereof.

2. The compound as claimed in claim 1 , characterized in that

R 1 is located in the meta- or para-position to the ethylamino radical and represents F, Cl or Br;

R 2 represents H or F or Cl;

R 3 represents H;

R 4 represents cyclohexyl or phenyl, where the phenyl radical may additionally carry a substituent from the group consisting of F, Cl, Br, CN, OMe, CF 3 ;

with the proviso that R 4 does not represent phenyl which carries a substituent CF 3 or OMe in the para-position to the point of attachment if, simultaneously, R 1 is in the meta-position to the ethylamino radical and represents F and R 2 and R 3 each represent H;

or a pharmaceutically acceptable salt or stereoisomer thereof.

3. The compound as claimed in claim 1 , characterized in that

R 1 is located in the meta-position to the ethylamino radical and represents Cl;

R 2 represents H or Cl;

R 3 represents H;

R 4 represents cyclohexyl or phenyl, where the phenyl radical may additionally carry a substituent from the group consisting of F, Cl, CN, OMe, CF 3 ;

or a pharmaceutically acceptable salt or stereoisomer thereof.

4. The compound as claimed in claim 1 , characterized in that

R 1 is located in the para-position to the ethylamino radical and represents Cl or F;

R 2 represents H or Cl;

R 3 represents H;

R 4 represents cyclohexyl or phenyl, where the phenyl radical may additionally carry a substituent from the group consisting of F, Cl, CN, OMe, CF 3 ;

or a pharmaceutically acceptable salt or stereoisomer thereof.

5. A process for preparing compounds of the general formula (I), characterized in that

compounds of the formula (II)

in which

R 1 , R 2 , R 3 and R 4 are as defined in claim 1 ,

is reacted with a C 1-6 -alkyl 4-formylbenzoate in an organic solvent with heating and with simultaneous or subsequent addition of a reducing agent to give compounds of the formula (III)

wherein

R 1 , R 2 , R 3 and R 4 are as defined above and Q represents a C 1-6 -alkyl radical,

then reacted with a C 1-6 -alkyl ω-halovalerate in an organic solvent in the presence of a base with heating to give compounds of the formula (IV)

wherein

R 1 , R 2 , R 3 and R 4 and Q are as defined above and Q′ represents a C 1-6 -alkyl radical,

and the compounds of the formula (IV) is then hydrolyzed under alkaline conditions to give the compounds of the formula (I).

6. A pharmaceutical composition comprising a compound of claim 1 and a phramceutically acceptable carrier.

7. A method for treating angina pectoris or ischemias comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .

8. A method for treating hypertension, or arteriosclerosis comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .

9. A method for treating fibrosis of the liver comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .