5-cyanothienopyridines for the treatment of tumours

1. A compound of the formula I

in which

R 1 denotes Het

R 2 , R 3 each, independently of one another, denote H, A, AlkNH 2 , AlkNHA, AlkNAA′, AlkNHSO 2 A, AlkOH, AlkOA, AlkCyc, AlkCycAlkOH, AlkCycAlkOA, AlkCycAlkCOOA, AlkCycAlkCOOH, AlkHet 1 , AlkOAlkOH, AlkOAlkOA, AlkOAlkNH 2 , AlkOAlkNHA, AlkOAlkNAA′, AlkCHOH(CH 2 ) n OH, AlkO(CH 2 ) m Het 1 or AlkAr, where one of the substituents R 2 and R 3 is not H,

R 2 and R 3 together may also be an alkylene chain having 1 to 6 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by N and/or O atoms and/or in which 1 to 6 H atoms may be replaced by A, OH, OA, (CH 2 ) n Het 1 , SO 2 A and/or Hal,

Alk denotes alkylene having 1 to 6 C atoms, in which 1 to 4 H atoms may be replaced by F, Cl and/or Br,

Cyc denotes cycloalkyl having 3 to 7 C atoms, in which 1 to 4 H atoms may be replaced by A, Hal, OH and/or OA,

Het denotes a benzofuranyl group, which may be mono- or disubstituted by A and/or Hal,

Het 1 denotes a monocyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which may be mono-, di- or trisubstituted by A, OH, OA, Hal, SO 2 A and/or ═O (carbonyl oxygen),

Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by A, OH, OA, Hal, SO 2 NH 2 , SO 2 NA and/or SO 2 NAA′,

A, A′ each, independently of one another, denote unbranched or branched alkyl having 1-10 C atoms, in which 1-5 H atoms may be replaced by F, Cl and/or Br,

Hal denotes F, Cl, Br or I,

m denotes 1, 2, 3, 4,

n denotes 0, 1, 2, 3, 4,

or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

2. A compound according to claim 1

in which

R 2 denotes H, A, AlkNH 2 , AlkNHA, AlkNAA′, AlkNHSO 2 A, AlkOH, AlkOA, AlkCyc, AlkCycAlkOH, AlkCycAlkOA, AlkCycAlkCOOA, AlkCycAlkCOOH, AlkHet 1 , AlkOAlkOH, AlkOAlkOA, AlkOAlkNH 2 , AlkOAlkNHA, AlkOAlkNAA′, AlkCHOH(CH 2 ) n OH, AlkO(CH 2 ) m Het 1 or AlkAr and

R 3 denotes H and

or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

3. A compound according to claim 1 in which

R 2 and R 3 together may also be an alkylene chain having 1 to 5 C atoms, in which one non-adjacent CH 2 group may be replaced by an N or O atom and/or in which 1 or 2 H atoms may be replaced by A, OH, OA, (CH 2 ) n Het 1 , and/or SO 2 A,

or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

4. A compound according to claim 1

in which

Het denotes a mono- or bicyclic unsaturated and/or aromatic heterocycle having 1 to 3 N, O and/or S atoms, which may be mono-, di- or trisubstituted by A, Hal and/or Ar,

or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

5. A compound according to claim 1

in which

Het 1 a monocyclic saturated or unsaturated heterocycle having 1 to 3 N, O and/or S atoms, which may be mono-, di- or trisubstituted by A, Hal, SO 2 A and/or ═O(carbonyl oxygen),

or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

6. A compound according to claim 1

in which

Ar denotes phenyl which is monosubstituted by SO 2 NH 2 , SO 2 NA or SO 2 NAA′

or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

7. The compound:

3,6-diamino-5-cyano-4-(5-methylfuran-2-yl)thieno[2,3-b]pyridine-2-carboxamide,

or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

8. Process for the preparation of a compound of the formula I according to claim 1 or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios, comprising:

a) for the preparation of a compound of the formula I in which R 2 , R 3 ═H, reacting a compound of the formula II

in which R 1 has the meaning indicated in claim 1 ,

with a compound of the formula III

H 2 N—CO—CH 2 —Z  III

in which

Z denotes Cl, Br, I or a free or reactive functionally modified OH group,

to give a compound of the formula IV

in which R 1 has the meaning indicated in claim 1 ,

and subsequently cyclizing the resultant compound of the formula IV to give the compound of the formula I,

or

b) for the preparation of the compound of the formula I in which at least one of the two radicals R 2 , R 3 is ≠H,

replacing the free amino group in a compound of the formula IV by Hal, giving a compound of the formula V

in which R 1 has the meaning indicated in claim 1 ,

then reacting the compound of the formula V with a compound of the formula VI

in which R 2 and R 3 have the meanings indicated in claim 1 , but at least one of the two radicals R 2 , R 3 is ≠H,

to give a compound of the formula VII

in which R 1 , R 2 , R 3 have the meanings indicated in claim 1 , but at least one of the two radicals R 2 , R 3 is ≠H,

and subsequently cyclizing the resultant compound of the formula VII to give the compound of the formula I,

and/or p 1 c) converting a base or acid of the formula I into one of its salts.

9. A composition comprising at least one compound according to claim 1 or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios, and at least one excipient and/or adjuvant.

10. A composition comprising, as a medicament, at least one compound according to claim 1 or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios, and at least one further medicament active compound.

11. Set (kit) consisting of separate packs of

(a) as a medicament, an effective amount of a compound of the according to claim 1 or a pharmaceutically usable salt, mono- or di-hydrate, alcoholate, tautomer or stereoisomer thereof, including mixtures thereof in all ratios,

and

(b) an effective amount of a further medicament active compound.