Isophthalic acid derivatives

1. A compound of the formula

in which

A is a 6-membered nitrogen-containing saturated heterocycle which is bonded via the nitrogen atom to the keto group and which optionally has a carbonyl group adjacent to a nitrogen atom,

m 0,1 or 2,

n is 1, 2, 3 or 4,

R 1 is hydrogen or (C 1 -C 6 )-alkyl,

R 2 is hydrogen or (C 1 -C 6 )-alkyl,

X is a bond, —CH═CH—, —C≡C— or O,

Y is O, *—NH—C(═O)— or NH,

in which

* is the point of linkage to the phenyl ring,

and

Z is located in the position meta or para to the substituent X and is either (C 6 -C 10 )-alkoxy which may comprise 1 or 2 further oxygen atoms in the chain,

or

a radical

 in which

G is a bond, O or S,

L is (C 1 -C 6 )-alkanediyl, (C 3 -C 6 )-alkenediyl or (C 3 -C 6 )-alkynediyl,

M is a bond, O or S,

R 4 is (C 6 -C 10 )-aryl, biphenylyl, phenoxyphenyl, benzyloxyphenyl, (E)-phenylvinylphenyl, 2-phenylethyiphenyl, tetrahydronaphthyl, benzyl, heteroaryl, 5- to 10-membered heterocyclyl, (C 3 -C 7 )-cycloalkyl or (C 3 -C 7 )-cycloalkylmethyl, where aryl, biphenylyl, phenoxyphenyl, benzyloxyphenyl, (E)-phenylvinylphenyl, 2-phenylethyiphenyl, tetrahydronaphthyl, benzyl, heteroaryl, heterocyclyl, cycloalkyl and cycloalkylmethyl in turn may be substituted up to three times independently of one another by halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyl, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkylmethoxy, (C 5 -C 7 )-cyclo-alkenyl, (C 3 -C 7 )-cycloalkoxy or (C 5 -C 7 )-cycloalkenyloxy, and

* is the point of linkage to the phenyl ring,

or a salt thereof.

2. The compound of claim 1 ,

in which

A is a 6-membered nitrogen-containing saturated heterocycle which is bonded via the nitrogen atom to the keto group,

m is 0 or 1,

n is 1, 2 or 3,

R 1 is hydrogen,

R 2 is hydrogen,

X is a bond or O,

Y is O or *—NH—C(═O)—,

in which

* is the point of linkage to the phenyl ring,

and

Z is located in the position meta or para to the substituent X and is either (C 7 -C 9 )-alkoxy, which may comprise 1 further oxygen atom in the chain,

or

a radical

 in which

G is a bond or O,

L is (C 1 -C 6 )-alkanediyl or (C 3 -C 6 )-alkenediyl,

M is a bond, O or S,

R 4 is phenyl, naphthyl, biphenylyl, phenoxyphenyl, benzyloxyphenyl, (E)-phenylvinylphenyl, 2-phenylethylphenyl, tetrahydronaphthyl, benzyl, 1,3-dioxanyl, 1,4-dioxanyl, dimethyl- 1,3-dioxanyl, tetrahydro-2H-pyranyl, (C 3 -C 7 )-cycloalkyl or (C 3 -C 7 )-cycloalkylmethyl, where phenyl, naphthyl, biphenylyl, phenoxyphenyl, benzyloxyphenyl, (E)-phenylvinylphenyl, 2-phenylethylphenyl, tetrahydronaphthyl, benzyl, cycloalkyl and cycloalkylmethyl in turn may be substituted up to three times independently of one another by halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkylmethoxy or (C 3 -C 7 )-cycloalkoxy, and

* is the point of linkage to the phenyl ring,

or a salt thereof.

3. The compound of claim 1 ,

in which

A—[CH 2 ] m —CO 2 R 1 is a radical

in which

* is the point of linkage to the keto group,

n is 3,

R 2 is hydrogen,

X is a bond,

Y is O,

and

Z is located in the position pam to the substituent X and is either n-octyloxy, n-heptyloxy,

or

a radical

 in which

* is the point of linkage to the phenyl ring,

or

a radical

 in which

G is O,

L is methanediyl, n-propanediyl or n-butanediyl,

M is a bond or O,

R 4 is phenyl, 4-biphenylyl, 4-phenoxyphenyl, 4-benzyloxyphenyl, 1,2,3,4-tetrahydronaphth-6-yl, 5,5-dimethyl-1,3-dioxan-2-yl or cyclohexyl, where phenyl in turn may be substituted once by halogen, trifluoromethoxy, (C 3 -C 4 )-alkyl, (C 3 -C 4 )-alkoxy, cyclopentyl, cyclohexyl or (C 3 -C 6 )-cycloalkylmethoxy, and

* is the point of linkage to the phenyl ring,

or a salt thereof.

4. The compound of claim 1 ,

in which

A—[CH 2 ] m —CO 2 R 1 is a radical

in which

* is the point of linkage to the keto group,

n is 3,

R 2 is hydrogen,

X is a bond,

Y is O,

and

Z is located in the position para to the substituent X, and is either n-octyloxy, n-heptyloxy,

or

a radical

 in which

* is the point of linkage to the phenyl ring,

or

a radical *—O—CH 2 R 4 ,

in which

R 4 is phenyl, 4-biphenylyl, 4-phenoxyphenyl, 4-benzyloxyphenyl or 1,2,3,4-tetrahydronaphth-6-yl, where phenyl in turn may be substituted once by trifluoromethoxy, n-propyl, n-butyl, tert-butyl, n-propyloxy, isopropyloxy, isobutyloxy, cyclohexyl or cyclopropylmethoxy, and

* is the point of linkage to the phenyl ring,

or

a radical *—O—CH 2 —CH 2 —CH 2 —R 4 ,

in which

R 4 is 4-chlorophenyl, 5,5-dimethyl-1,3-dioxan-2-yl or cyclohexyl, and

* is the point of linkage to the phenyl ring,

or

a radical *—O—CH 2 —CH 2 —CH 2 —CH 2 —O—R 4 ,

in which

R 4 is phenyl or cyclohexyl, and

* is the point of linkage to the phenyl ring,

or a salt thereof.

5. The compound of claim 1 ,

in which

A—[CH 2 ] m —CO 2 R 1 is a radical

in which

* is the point of linkage to the keto group,

n is 3,

R 2 is hydrogen,

X is a bond,

Y is O,

and

Z is located in the position para to the substituent X and is a radical

in which

* is the point of linkage to the phenyl ring,

or a salt thereof.

6. The compound of claim 1 , wherein the compound is 1-(5-carboxy-2-{3-[4-(3-cyclohexylpropoxy)phenyl]propoxy}benzoyl)piperidine-4-carboxylic acid, or a salt thereof.

7. A process for preparing a compound of claim 1 , comprising

either

[A] reacting a compound of the formula (II)

in which

R 2 is (C 1 -C 6 )-alkyl and

n, X, Y and Z have the meaning indicated in claim 1 ,

with a compound of the formula (III)

in which

R 1 is (C 1 -C 6 )-alkyl, and

m and A have the meaning indicated in claim 1 ,

or

[B1] reacting a compound of the formula (IVa)

in which

Q 1 is a leaving group and

n, X and Z have the meaning indicated in claim 1 ,

with a compound of the formula (Va)

in which

R 1 and R 2 are (C 1 -C 6 )-alkyl, and

A and m have the meaning indicated in claim 1 ,

or

[B2] reacting a compound of the formula (IVb)

in which

Q 2 is an acid chloride group, and

n, X and Z have the meaning indicated in claim 1 ,

with a compound of the formula (Vb)

in which

R 1 and R 2 are (C 1 -C 6 )-alkyl, and

A and m have the meaning indicated in claim 1 ,

or

[B3] reacting a compound of the formula (IVa)

in which

Q 1 is a leaving group and

n, X and Z have the meaning indicated in claim 1 ,

with a compound of the formula (Vb)

in which

R 1 and R 2 are (C 1 -C 6 )-alkyl, and

A and m have the meaning indicated in claim 1 ,

or

[C] reacting a compound of the formula (XII)

in which

R 1 and R 2 are (C 1 -C 6 )-alkyl, and

n, m, X, Y and A have the meaning indicated in claim 1 ,

with a compound of the formula (XIII)

R 4 -M-L-Q 3 (XIII),

in which

Q 3 is a leaving group and

R 4 , M and L have the meaning indicated in claim 1 ,

or

[D] hydrolysing the two ester groups in the compound prepared by process step [A], [B1], [B2], [B3] or [C].

8. A pharmaceutical composition comprising at least one compound of claim 1 and at least one excipient.

9. A pharmaceutical composition comprising at least one compound of claim 1 and at least one further active ingredient.