N-benzylindole and benzopyrazole derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunemodulating effect
AssigneeAsta Medica Aktiengesellschaft
InventorsGuillaume Lebaut, Fabienne Fouchard, Bernhard Kutscher, Peter Emig, Ilona Fleischhauer, Jurgen Schmidt, Stefan Szelenyi
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Abstract
The N-benzylindole- and benzopyrazole derivatives of the general formula 1 ##STR1## possess anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effect and are suitable for the preparation of medicaments.
Claims17
A compound of formula 1:
- ##STR398## wherein R.sup.1 represents hydrogen, a straight-chained (C.sub.1 -C.sub.6)alkyl group, which is optionally substituted by phenyl or halogen-substituted phenyl;
- R.sup.2 represents hydrogen or a branched (C.sub.1 -C.sub.6) alkyl group;
- R.sup.3 represents hydrogen;
- W represents CH;
- X represents CH;
- Y represents a single bond in such a manner that the heterocyclic system is directly associated with the group ##STR399## wherein n is 1-6 and R.sup.4 represents hydrogen;
- G represents ##STR400## wherein m is 1, Z represents O or two hydrogen atoms, R.sup.5 represents the radical ##STR401## wherein R.sup.6 represents hydrogen and R.sup.7 represents a pyridine skeleton, which is linked to one of the ring carbon atoms and is optionally substituted with radicals R.sup.8 and R.sup.9 which may be identical or different and represent straight-chained (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6)alkoxy, or ethoxycarbonylamino, and wherein ##STR402## may also include one --CH.dbd.CH-- unit when n is equal to or greater than two;
- and pharmaceutically usable acid addition salts thereof.
N-(4-pyridyl)-[1-(4-fluorobenzyl)indole-3-yl]acetamine and the physiologically acceptable acid addition salts thereof.
N-(3-pyridyl)-2-[1-(4-fluorobenzyl)indole-3-yl]ethylamine and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-2-(1-benzyl-2-methyl-5-isopropylindole-3-yl)acetamide, and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-2-(5-isopropyl-1H-indole-3-yl)acetamine and the physiologically acceptable acid addition salts thereof.
N-(2-pyridyl)-2-[1-(4-fluorobenzyl)indole-3-yl]ethylamine, and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-2-[1-(4-fluorobenzyl)6-hydroxyindole-3-yl]acetamide, and the physiologically acceptable acid addition salts thereof.
N-(4,6-dimethyl-2-pyridyl)-3-[1-(4-fluorobenzyl)indole-3-yl)]propenamide and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-2-(1-benzylindole-3-yl)ethylamine and the physiologically acceptable acid addition salts thereof.
N-(3-pyridyl)-3-[1-(4-fluorobenzyl)-indole-3-yl)propylamine and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-3-(1-p-fluorobenzylindole-3-yl)propylamine and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-3-(1-methylindole-3-yl)propylamine and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-2-[1-(4-fluorobenzyl)indole-3-yl]ethylamine and the physiologically acceptable acid addition salts thereof.
N-(4-pyridyl)-(1-ethylindole-3-yl)acetamide and the physiologically acceptable acid addition salts thereof.
N-(3-ethoxycarbonylamino-6-methoxy-2 -pyridyl)-2-(1-benzylindole-3-yl)ethylamine and the physiologically acceptable acid addition salts thereof.
N-(3-ethoxycarbonylamino-6-methoxy-2 -pyridyl)-3-(1-(4-fluorobenzyl)indole-3-yl)propylamine and the physiologically acceptable acid addition salts thereof.
Dependencies are inferred from the claim text.