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US 2004/0106641 A1Published application
Novel 7-azaindoles, use thereof as phosphodiesterase 4 inhibitors and method for producing the same
AssigneeElbion AG
InventorsNorbert Hofgen, Ute Egerland, Thomas Kronbach, Degenhard Marx, Stefan Szelenyi, Hildegard Kuss, Emmanuel Polymeropoulos
Life of this patent
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Abstract
The invention relates to new 7-azaindoles, their use as inhibitors of phosphodiesterase 4 and to methods for their synthesis.
Claims18
7-Azaindoles of the general formula 1
- 25
- in which
- n can be 1 or 2 and
- R1 represents
- a —C1 to —C10 linear or branched alkyl, unsubstituted or substituted one or more times with —OH, —SH, —NH2, —NHC1 to —NHC6 alkyl, —N(C1 to C6-alkyl)2, —NHC6 to —NHC14 aryl, —N(C6 to C14 aryl)2, —N(C1 to C6 alkyl)(C6 to C14 aryl), —NO2, —CN, —F, —Cl, —Br, —I, —O—C1 to —O—C6 alkyl, —O—C6 to —O—C14 aryl, —S—C1 to —S—C6 alkyl, —S—C6 to —S—C14 aryl, —SO3H, —SO2C1 to —SO2C6 alkyl, —SO2C6 to —SO2C14 aryl, —OSO2C1 to —OSO2C6 alkyl, —OSO2C6 to —OSO2C14 aryl, —COOH, —(CO)C1 to —(CO)C5 alkyl, with mono-, bi- or tricyclic, 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, which preferably are N, O and S,
- the C6 to C14 aryl groups and the carbocyclic and heterocyclic substituents, in turn, may be unsubstituted or monosubstituted or multi-substituted with R4,
- —C2 to C10 alkenyl, monounsaturated or multi-unsaturated, linear or branched, unsubstituted or monosubstituted or multi-substituted with —OH, —SH, —NH2, —NHC1 to —NHC6 alkyl, —N(C1 to C6-alkyl)2, —NHC6 to —NHC14 aryl, —N(C6 to C14 aryl)2, —N(C1 to C6 alkyl)(C6 to C14 aryl), —NO2, —CN, —F, —Cl, —Br, —I, —O—C1 to —O—C6 alkyl, —O—C6 to —O—C14 aryl, —S—C1 to —S—C6 alkyl, —S—C6 to —S—C14 aryl, —SO3H, —SO2C1 to —SO2C6 alkyl, —SO2C6 to —SO2C14 aryl, —OSO2C1 to —OSO2C6 alkyl, —OSO2C6 to —OSO2C14 aryl, —COOH, —(CO)C1 to —(CO)C5 alkyl, with mono-, bi- or tricyclic, 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, which preferably are N, O and S,
- the C6 to C14 being aryl groups and the carbocyclic and heterocyclic substituents, in turn, may be unsubstituted or monosubstituted or multi-substituted with R4,
- R2 and R3 may be the same or different, only one of the two representing hydrogen and furthermore, R2 and R3 can represent
- —C1-C5 alkyl,
- unsubstituted or monosubstituted or multi-substituted with —OH, —SH, —NH2, —NHC1 to —NHC6 alkyl, —N(C1 to C6-alkyl)2, —NO2, —CN, —F, —Cl, —Br—, —I, —O—C1 to —O—C6 alkyl, —S—C1 to —S—C6 alkyl-phenyl, -pyridyl
- -phenyl,
- unsubstituted or monosubstituted or multi-substituted with —OH, —SH, —NH2, —NHC1 to —NHC3 alkyl, —N(C1 to C3-alkyl)2, —NO2, —CN, —COOH, —COOC1 to —COOC3 alkyl, —F, —Cl, —Br—, —O—C1 to —O—C3 alkyl, —S—C1 to —S—C3 alkyl,
- -pyridyl,
- unsubstituted or monosubstituted or multi-substituted with —NO2, —CN, —COOH, —COOC1 to —COOC3 alkyl, —Cl, —Br—, —O—C1 to —O—C3 alkyl, —S—C1 to —S—C3 alkyl
- as well as
- 26
- furthermore, the —NR2R3 group can represent together
- 27
- and R4 represents
- —H, —OH, —SH, —NH2, —NHC1 to —NHC6 alkyl, —N(C1 to C6 alkyl)2, NHC6 to NHC14 aryl, N(C6 to C14 aryl)2, —N(C1 to C6 alkyl)(C6 to C14 aryl), —NHCOC1 to —NHCOC6 alkyl, —NO2, —CN, —COOH, —COOC1 to —COOC6 alkyl, —(CO)C1 to —(CO)C6 alkyl, —(CS)C1 to —(CS)C6 alkyl, —F, —Cl, —Br, —I, —O—C1 to —O—C6 alkyl, —O—C6 to —O—C14 aryl, —S—C1 to —S—C6 alkyl, —S—C6 to —S—C14 aryl, —SOC1 to —SOC6 alkyl, —SO2C1 to —SO2C6 alkyl.
18 more elements
Dependencies are inferred from the claim text.