Dicarboxylic acid derivatives and their use

1. A compound of formula (I-A)

in which

A 1 is (C 1 -C 7 )-alkanediyl

and

A 2 is hydrogen or a group of the formula

in which * is the point of linkage to the group A 1 and

R 4 A is hydrogen, fluorine, chlorine, methyl, tert-butyl, trifluoromethyl, methoxy or trifluoromethoxy,

or the salts, solvates and solvates of the salts thereof.

2. A compound of formula (I-B)

in which

A 1 is (C 1 -C 7 )-alkanediyl

and

A 2 is hydrogen or a group of the formula

in which * is the point of linkage to the group A 1 and

R 4 A is hydrogen, fluorine, chlorine, methyl, tert-butyl, trifluoromethyl, methoxy or trifluoromethoxy,

or the salts, solvates and solvates of the salts thereof.

3. A method for preparing a compound of formula (I-A) as defined in claim 1 , comprising:

reacting a compounds of formula (II)

in which

R 2 and R 3 are independently of one another a substituent selected from the series halogen, (C 1 -C 6 )-alkyl, trifluoromethyl, (C 1 -C 6 )-alkoxy, trifluoromethoxy, cyano and nitro,

where in the case where R 2 or R 3 occur more than once, their meanings may in each case be identical or different,

o and p are in each case independently of one another the number 0, 1, 2, 3, or 4, and

T 1 and T 2 are identical or different and are cyano or (C 1 -C 4 )-alkoxycarbonyl,

either

[A] in an inert solvent in the presence of a base with a compound of formula (III-A)

in which A is a group of formula —O-A 1 -A 2 , and A 1 and A 2 each have the meanings indicated in claim 1 ,

R 1 is a substituent selected from the series halogen, (C 1 -C 6 )-alkyl, trifluoromethyl, (C 1 -C 6 )-alkoxy, trifluoromethoxy, cyano and nitro, and in the case where R 1 occurs more than once, its meaning in each case may be identical or different,

n is the number 0, 1, 2, 3 or 4,

L is phenyl or o-, m- or p-tolyl

and

X is halide or tosylate,

to give a compound of formula (IV-A)

in which A, R 1 , R 2 , R 3 , n, o, p, T 1 and T 2 each have the meanings indicated above,

or

[B] in an inert solvent in the presence of a base with a compound of formula (III-B)

in which R 1 , n, L and X each have the meanings indicated above,

to give a compound of formula (IV-B)

in which R 1 , R 2 , R 3 , n, o, p, T 1 and T 2 each have the meanings indicated above,

and alkylating the compound of formula (IV-B) in an inert solvent in the presence of a base with a compound of formula (V)

A 2 -A 1A Q  (V),

in which A 2 has the meaning indicated in claim 1 ,

A 1A has the meaning indicated in claim 1 , for A 1 but is not a bond,

and

Q is a leaving group,

to give a compound of the formula (IV-C)

in which A 1A , A 2 , R 1 , R 2 , R 3 , n, o, p, T 1 and T 2 each have the meanings indicated above,

and converting the resulting compound of the formula (IV-A) or (IV-C) by hydrolysis of the ester or nitrile groups T 1 and T 2 into a compound of formula (I-A),

and optionally reacting the compound of formula (I-A) with an appropriate (i) solvent and/or (ii) base or acid to give a salt thereof.

4. A pharmaceutical composition comprising a compound of claim 1 or 2 and an inert, non-toxic, pharmaceutically suitable excipient.

5. The pharmaceutical composition according to claim 4 , further comprising an active ingredient selected from the group consisting of an organic nitrate, an NO donor, a cGMP-PDE inhibitor, a stimulator of guanylate cyclase, an agent having antithrombotic activity, an agent lowering blood pressure, and an agent altering lipid metabolism.

6. A method for preparing a compound of formula (I-B) as defined in claim 2 , comprising:

reacting a compound of formula (II)

in which R 2 and R 3 are independently of one another a substituent selected from the series halogen, (C 1 -C 6 )-alkyl, trifluoromethyl, (C 1 -C 6 )-alkoxy, trifluoromethoxy, cyano and nitro,

where in the case where R 2 or R 3 occur more than once, their meanings may in each case be identical or different,

o and p are in each case independently of one another the number 0, 1, 2, 3, or 4, and

T 1 and T 2 are identical or different and are cyano or (C 1 -C 4 )-alkoxycarbonyl,

either

[A] in an inert solvent in the presence of a base with a compound of formula (III-A)

in which A is a group of formula —O-A 1 -A 2 , and A 1 and A 2 each have the meanings indicated in claim 2

R 1 is a substituent selected from the series halogen, (C 1 -C 6 )-alkyl, trifluoromethyl, (C 1 -C 6 )-alkoxy, trifluoromethoxy, cyano and nitro, and in the case where R 1 occurs more than once, its meaning in each case may be identical or different,

n is the number 0, 1, 2, 3 or 4,

L is phenyl or o-, m- or p-tolyl

and

X is halide or tosylate,

to give a compound of formula (IV-A)

in which A, R 1 , R 2 , R 3 , n, o, p, T 1 and T 2 each have the meanings indicated above,

or

[B] in an inert solvent in the presence of a base with a compound of formula (III-B)

in which R 1 , n, L and X each have the meanings indicated above,

to give a compound of formula (IV-B)

in which R 1 , R 2 , R 3 , n, o, p, T 1 and T 2 each have the meanings indicated above,

and alkylating the compound of formula (IV-B) in an inert solvent in the presence of a base with a compound of formula (V)

A 2 -A 1A -Q  (V),

in which A 2 has the meaning indicated in claim 2 ,

A 1A has the meaning indicated in claim 2 for A 1 but is not a bond,

and

Q is a leaving group,

to give a compound of the formula (IV-C)

in which A 1A , A 2 , R 1 , R 2 , R 3 , n, o, p, T 1 and T 2 each have the meanings indicated above,

and converting the resulting compound of the formula (IV-A) or (IV-C) by hydrolysis of the ester or nitrile groups T 1 and T 2 into a compound of formula (1-B),

and optionally reacting the compound of formula (I-B) with an appropriate (i) solvent and/or (ii) base or acid to give a salt thereof.

7. A compound of formula:

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

8. The compound of claim 7 , wherein the compound is enantiomer I of the formula.

9. A compound of formula:

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