7-azaindoles and the use thereof as therapeutic agents

1. A compound of formula 1

wherein

A is nitrogen,

B is N—O,

R 1

(i) is —C 1-10 -alkyl, straight-chain or branched-chain, optionally mono- or polysubstituted by —OH, —SH, —NH 2 , —NHC 1-6 -alkyl, —N(C 1-6 -alkyl) 2 , —NHC 6-14 -aryl, —N(C 6-14 -aryl) 2 , —N(C 1-6 -alkyl)(C 6-14 -aryl), —NO 2 , —CN, —F, —Cl —Br, —I, —O—C 1-6 -alkyl, —O—C 6-14 -aryl, —S—C 1-6 -alkyl, —S—C 6-14 -aryl, —SO 3 H, —SO 2 C 1-6 -alkyl, —SO 2 C 6-14 -aryl, —OSO 2 C 1-6 -alkyl, -OSO 2 C 6-14 -aryl, —COOH, —(CO)C 1-5 -alkyl, —COO—C 1-5 -alkyl, —O(CO)C 1-5 -alky, by mono-, bi- or tricyclic saturated or mono- or polyunsaturated carbocycles with 3–14 ring members or by a mono-, bi- or tricyclic saturated or mono- or polyunsaturated heterocycle with 5–15 ring members and 1–6 heteroatoms,

where the C 6-14 -aryl groups and the carbocyclic and heterocyclic substituents in turn may optionally be substituted one or more times by at least one of —C 1-6 -alkyl, —OH, —NH 2 , —NHC 1-6 -alkyl, —N(C 1-6 -alkyl) 2 , —NO 2 , —CN, —F, —Cl, —Br, —I, —O—C 1-6 -alkyl, —S —C 1-6 -alkyl, —SO 3 H, —SO 2 C 1-6 -alkyl, —OSO 2 C 1-6 -alkyl, —COOH, —(CO)C 1-5 -alkyl, —COO—C 1-5 -alkyl or —O(CO)C 1-5 -alkyl, and where the alkyl groups on the carbocyclic and heterocyclic substituents in turn may optionally be substituted one or more times by —OH, —SH, —NH 2 , —F, —Cl, —Br, —I, —SO 3 H or —COOH, or

(ii)is —C 2-10 -alkenyl, mono- or polyunsaturated, straight-chain or branched-chain, optionally mono- or polysubstituted by —OH, —SH, —NH 2 , —NHC 1-6 -alkyl, —N(C 1-6 -alkyl) 2 , —NHC 0-14 -aryl, —N(C 6-14 -aryl) 2 , —N(C 1-6 -alkyl)(C 6-14 -aryl), —NO 2 , —CN, —F, —Cl, —Br, —I, —O—C 1-6 -alkyl, —O—C 6-14 -aryl, —S—C 1-6 -aIkyl, —S—C 6-14 -aryl, —SO 3 H —SO 2 C 1-6 -alkyl, —SO 2 C 6-14 -aryl, —OSO 2 C 1-6 -aIkyl, —OSO 2 C 6-14 -aryl, —COOH, -(CO)C 1-5 alkyl, —COO—C 1-5 -alkyl, —O(CO)C 1-5 alkyl, by mono-, bi- or tricyclic saturated or mono- or polyunsaturated carbocycles with 3–14 ring members or/and by mono-, bi- or tricyclic saturated or mono- or polyunsaturated heterocycles with 5–15 ring members and 1–6 heteroatoms,

where the C 6-14 -aryl groups and the carbocyclic and heterocyclic substituents in turn may optionally be substituted one or more times by at least one of —C 1-6 -alkyl, —OH, —NH 2 , —NHC 1-6 -alkyl, —N(C 1-6 -alkyl) 2 , —NO 2 , —CN, —F, —Cl, —Br, —I, —O—C 1-6 -alkyl, —S—C 1-6 -alkyl, —SO 3 H, —SO 2 C 1-6 -alkyl, -OSO 2 C 1-6 -alkyl, —COOH, —(CO)C 1-5 -alkyl, —COO—C 1-5 -alkyl or —O(CO)C 1-5 -alkyl,

and where the alkyl groups on the carbocyclic and heterocylic substituents in turn may optionally be substituted one or more times by at least one of —OH, —SH, —NH 2 , —F, —Cl, —Br, —I, —SO 3 H or —COOH,

R 2 is hydrogen or —C 1-3 -alkyl,

R 3 and R 4 may be identical or different and are hydrogen, —C 1-6 -alkyl, —OH, —SH, —NH 2 , —NHC 1-6 -alkyl, —N(C 1-6 -alkyl) 2 , —NO 2 , —CN, —SO 3 H, —SO 3 —C 1-6 -alkyl, —COOH, -COO-C 1-6 -alkyl, —O(CO)—C 1-5 -alkyl, —F, —Cl, —Br, —I, —O—C 1-6 -alkyl, —S—C 1-6 -alkyl, -phenyl or -pyridyl, where the phenyl or pyridyl substituents in turn may optionally be substituted one or more times by at least one of —C 1-3 -alkyl, —OH, —SH, —NH 2 , —NHC 1-3 -alkyl, —N(C 1-3 -alkyl) 2 , —NO 2 , —CN, —SO 3 H, —SO 3 C 1-3 -alkyl, —COOH, —COOC 1-3 -alkyl, —F, —Cl, —Br, —I, —O—C 1-3 -alkyl, —S—C 1-3 -alkyl, or/and —O(CO)C 1-3 -alkyl, and where the alkyl substituents in turn may optionally be substituted one or more times by —OH, —SH, —NH 2 , —F, —Cl, —Br, —I, —SO 3 H, —SO 3 C 1-3 -alkyl, —COOH, —COOC 1-3 -alkyl, —O—C 1-3 -alkyl, —S—C 1-3 -alkyl or/and —O(CO)—C 1-3 -alkyl.

or a salt thereof.

2. A compound as claimed in claim 1 having at least one asymmetric carbon atom in the D form, the L form and D,L mixtures, and in the case of a plurality of asymmetric carbon atoms also the diastereomeric forms.

3. A compound as claimed in claim 1 , wherein R 2 is —H or —CH 3—.

4. A compound as claimed in claim 1 , wherein at least one of R 3 and R 4 is a halogen atom.

5. A compound as claimed in claim 3 , wherein R 2 is —CH 3.

6. A compound as claimed in claim 2 , wherein R 2 is —H or —CH 3.

7. A compound as claimed in claim 6 , wherein at least one of R 3 and R 4 is a halogen atom.

8. A compound as claimed in claim 1 selected from the group consisting of:

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(4-flurobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2-fluorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(3-nitrobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2,6-difluorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2,4-dichlorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2-chlorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-N-methyl-[1-(2-chlorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-methyl-N-(1-oxopyridin-4-yl)-[1-(2-chlorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2,6-dichlorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2-methylbenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1(2,6-dimethylbenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-(1-hexyl-7-azaindol-3-yl)glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-(1-isobutyl-7-azaindol-3-yl)glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-(1-cyclopropylmethyl-7-azaindol-3-yl)glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-naphth-1-yl-methyl)-7-azaindol-3-yl]glyoxylaxnide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2-chloro-6-fluorobenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2-difluoromethylbenzyl)-7-azaindol-3-yl]glyoxylamide;

N-(3,5-dichloro-1-oxopyridin-4-yl)-[1-(2-cyanobenzyl)-7-azaindol-3-yl]glyoxylamide;

and physiologically tolerated salts thereof.

9. The compound of claim 1 , wherein the heteroatoms in (i) are N,O or S.

10. The compound of claim 1 , wherein the heteroatoms in (ii) are N,O or S.

11. The compound of claim 9 , wherein the heteroatoms in (ii) are N,O or S.

12. A drug product comprising a compound according to claim 1 and at least one of a conventional physiologically tolerated carrier, diluent or excipient.

13. A pharmaceutical composition comprising a compound of claim 1 and at least one other active pharmaceutical agent.

14. A process for producing a drug product as claimed in claim 12 , comprising admixing said compound with said carrier, diluent or excipient to form the drug product.