7-azaindoles, their use as inhibitors of phosphodiesterase 4, and a method for synthesizing them

1. A method comprising administering a therapeutically effective amount of a 7-azaindole of the formula 1

or a physiologically tolerated salt thereof

wherein n is 2;

R 1 is a —C 1 to —C 10 linear or branched alkyl; which may be unsubstituted or substituted with at least one of —OH, —SH, —NH 2 , —NHC 1 to —NHC 6 alkyl,

—N(C 1 to C 6 -alkyl) 2 , —NHC 6 to —NHC 14 aryl, —N(C 6 to C 14 aryl) 2 , —N(C 1 to C 6 alkyl)(C 6 to C 14 aryl), —NO 2 , —CN, —F, —Cl, —Br, —I, —O—C 1 to —O—C 6 alkyl, —O—C 6 to —O—C 14 aryl, —S—C 1 to —S—C 6 alkyl, —S—C 6 to —S—C 14 aryl, —SO 3 H, —SO 2 C 1 to —SO 2 C 6 alkyl, —SO 2 C 6 to —SO 2 C 14 aryl, —OSO 2 C 1 to —OSO 2 C 6 alkyl, —OSO 2 C 6 to —OSO 2 C 14 aryl —COOH, —(CO)C 1 to —(CO)C 5 alkyl, with mono-, bi- or tri-cyclic, saturated or monounsaturated or multi-unsaturated carbocyclic compounds with 3 to 14 ring elements, with mono-, bi- or tricyclic saturated or monounsaturated or multi-unsaturated heterocyclic groups with 5 to 15 ring elements and 1 to 6 hetero atoms selected from the group consisting of N, O and S, or a —C 2 to —C 10 alkenyl, monounsaturated, multiunsaturated, linear, branched, unsubstituted, monosubstituted or multi-substituted with at least one of —OH, —SH, —NH 2 , to —NHC 1 to —NHC 6 alkyl, —N(C 1 to C 6 -alkyl) 2 , —NHC 6 to —NHC 14 aryl, —N(C 6 to C 14 aryl) 2 , —N(C 1 to C 6 alkyl)(C 6 to C 14 aryl), —NO 2 , —CN, —F, —Cl, —Br, —I, —O—C 1 to —O—C 6 alkyl, —O—C 6 to —O—C 14 aryl, —S—C 1 to —S—C 6 alkyl, —S—C 6 to —S—C 14 aryl, —SO 3 H, —SO 2 C 1 to —SO 2 C 6 alkyl, —SO 2 C 6 to —SO 2 C 14 aryl, —OSO 2 C 1 to —OSO 2 C 6 alkyl, —OSO 2 C 6 to —OSO 2 C 14 aryl, —COOH, —(CO)C 1 to —(CO)C 5 alkyl, with mono-, bi- or tri-cyclic, saturated or monounsaturated or multi-unsaturated carbocyclic compounds with 3 to 14 ring elements, with mono-, bi- or tri-cyclic saturated or monounsaturated or multi-unsaturated heterocyclic groups with 5 to 15 ring elements and 1 to 6 hetero atoms selected from N, O and S, wherein said C 6 to C 14 aryl groups and the carbocyclic and heterocyclic substituents may optionally be substituted at least once with R 4 ;

R 2 and R 3 are independently selected from the group consisting of —H, —C 1 -C 5 alkyl, unsubstituted or monosubstituted or multi-substituted with —OH, —SH, —NH 2 , —NHC 1 to —NHC 6 alkyl, —N(C 1 to C 3 -alkyl) 2 , —NO 2 , —CN, —F, —Cl, —Br—, —I, —O—C 1 to —O—C 6 alkyl, —S—C 1 to —S—C 6 alkyl, -phenyl, -pyridyl, or -phenyl, unsubstituted or monosubstituted or multi-substituted with —OH, —SH, NH 2 , —NHC 1 , to —NHC 3 alkyl, —N(C 1 to C 3 -alkyl) 2 , —NO 2 , —CN, —COOH, to —COOC 1 — alkyl, —F, —Cl, —Br—, —O—C 1 to —O—C 3 alkyl, —S—C 1 to —S—C 3 alkyl,

or pyridyl, unsubstituted or monosubstituted or multisubstituted with NO2, —CN 1 —COOH 1 —COOC 1 to —COOC 3 alkyl, —C 1 , —Br, —O—C 1 to —OC 3 alkyl, —S—C 1 to S—C 3 alkyl, or

wherein —NR 2 R 3 can be

R 4 is —H, —OH, —NH 2 , —NHC 1 to —NHC 6 alkyl, —N(C 1 to C 6 alkyl) 2 , —NHC 6 to —NHC 14 aryl,

—N(C 6 to C 14 aryl) 2 , —N(C 1 to C 6 alkyl)(C 6 to C 14 aryl), —NHCOC 1 to —NHCOC 6 alkyl, —NO 2 , —CN, —COOH, —COOC 1 to —COOC 6 alkyl, —(CO)C 1 to —(CO)C 6 alkyl, —(CS)C 1 to —(CS)C 6 alkyl, —F, —Cl, —Br, —I, —O—C 1 to —O—C 6 alkyl, —O—C 6 to —O—C 14 aryl, —S—C 1 to —S—

C 6 alkyl, —S—C 6 to —S—C 14 aryl, —SOC 1 to SOC 6 alkyl, —SO 2 C 1 to —SO 2 C 6 alkyl

to a subject afflicted with at least one condition selected from the group of inflammation of the joints, arthritis, arthritic diseases, rheumatoid arthritis, rheumatoid spondylitis, and osteoarthritis to treat the condition.

2. The method of claim 1 , wherein the 7-azaindole is N-(3,5-dichloropyridine-4-yl)-[(1-(4-fluorobenzyl)-7-azaindole-3-yl]glyoxylic acid amide.

3. The method of claim 1 , wherein the condition is inflammation of the joints.

4. The method of claim 1 , wherein the condition is arthritis.

5. The method of claim 1 , wherein the condition is arthritic diseases.

6. The method of claim 1 , wherein the condition is rheumatoid arthritis.

7. The method of claim 1 , wherein the condition is rheumatoid spondylitis.

8. The method of claim 1 , wherein the condition is osteoarthritis.

9. The method of claim 2 , wherein the condition is inflammation of the joints.

10. The method of claim 2 , wherein the condition is arthritis.

11. The method of claim 2 , wherein the condition is arthritic diseases.

12. The method of claim 2 , wherein the condition is rheumatoid arthritis.

13. The method of claim 2 , wherein the condition is rheumatoid spondylitis.

14. The method of claim 2 , wherein the condition is osteoarthritis.