Duphar International Research Bv

Hans H Haeck

Ineke Van Wijngaarden

Derk Hamminga

Wouter Wouters

Johannes W Jansen

The invention relates to a group of new 8,9-annelated-.beta.-carbolines and 8,9-annelated-3,4-dihydro-.beta.-carbolines having interesting fibrinolytic properties. In particular the compounds can be used as orally active fibrinolytics. The compounds have the general formulae 1 and 2 ##STR1## wherein R.sub.2 +R.sub.3 together with the carbon atom and the nitrogen atom to which they are bound and the intermediate carbon atom constitute a heterocyclic group consisting of 5-10 ring atoms.

8,9-annelated-.beta.-carbolines and 8,9-annelated

The invention relates to a group of new annelated indolo [3,2-c] lactam derivatives of the formula ##STR1## having an antagonistic activity on 5-HT receptors. The compounds can be used for the treatment of symptoms which are caused by excessive stimulation of said receptors in the gastrointestinal system, the central nervous system, the cardiovascular system, the respiratory system, and for alleviating or preventing withdrawal symptoms which are induced by abuse of drugs.

Annelated indolo [3,2,-C]lactams

1,7-Annelated esters and amides of indolecarboxylic acids having formula 2, ##STR1## wherein R.sub.1 is halogen;

1,7-annelated indolecarboxylic acid esters and amides

The invention relates to a group of new 3-N substituted carbamoyl-indole derivatives of the formula ##STR1## having an antagonistic activity on 5-HT receptors. The compounds can be used for the treatment of symptoms which are caused by excessive stimulation of said receptors in the gastrointestinal system, the central nervous system, the cardiovascular system, the respiratory system, and for alleviating or preventing withdrawal symptoms which are induced by abuse of drugs.

New 3-N substituted carbamoyl-indole derivatives

Annelated indoleketones with an imidazolylalkyl substituent having the formula (2): ##STR1## wherein R.sub.1 is alkyl or alkoxy having 1-4 C-atoms, hydroxy, halogen, trifluoromethyl, a group R.sub.5 R.sub.6 N or R.sub.5 R.sub.6 -N-CO, wherein R.sub.5 and R.sub.6 are hydrogen or alkyl having 1-4 C-atoms or wherein R.sub.5 R.sub.6 N is a saturated 5-6 ring, and n has the value 0, 1 or 2;

Annelated indoleketones with an imidazolylalkyl substituent

The invention relates to new 1,7-annelated esters and amides of indolecarboxylic acids having general formula 2, ##STR1## wherein the symbols have the meanings given in the specification. The compounds and their salts are very strong and selective antagonists of 'neuronal' 5-hydroxytryptamine (5-HT) receptors, and can be used for the treatment of symptoms which are caused by over-stimulation of these receptors.

1,7-annelated indolecarboxylic acid esters and -amides

The invention relates to a group of new substituted 1,7-annelated 1H-indazole derivatives being strong and selective antagonists of 'neuronal' 5-hydroxytryptamine (5-HT) receptors. The compounds can be represented by general formula 1: ##STR1##

Certain substituted 1,7-annelated 1h-indazoles being selective

The invention relates to a group of new substituted 1,7-annelated 1H-indazole derivatives being strong and selective antagonists of 'neuronal' 5-hydroxytryptamine (5-HT) receptors.

Substituted 1,7-annelated 1H-indazoles

The invention relates to new anellated indole derivatives of general formula 2, ##STR1## wherein p1 R.sub.0 is alkyl or alkoxy having 1-4 C-atoms, phenylalkoxy having 1-3 C-atoms in the alkoxy group, hydroxy, halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, or a group R.sub.7 S(O).sub.p, wherein R.sub.7 is alkyl having 1-4 C-atoms and p has the value 0, 1 or 2, or R.sub.0 is a group R.sub.8 R.sub.9 N, R.sub.8 R.sub.9 N--CO--CH.sub.2 -- or R.sub.8 R.sub.9 --N--CO wherein R.sub.8 and R.sub.9 are hydrogen or alkyl having 1-4 C-atoms or R.sub.8 R.sub.9 N forms a saturated 5- or 6-membered ring and n has the value 0, 1 or 2, Z together with the carbon atom and nitrogen atom to which Z is bound and the intermediate carbon atom, forms a heterocyclic group consisting of 5-8 ring atoms, in which, in addition to the nitrogen atom already present, a --CO--group or a second hetero atom from the group N, O, S, S-O or SO.sub.2 may be present, which ring may be substituted with 1-3 alkyl groups having 1-4 C-atoms, a phenyl group or a spiroalkyl group (C.sub.2 -C.sub.5), or which ring may be anellated with a saturated or non-saturated carbocyclic or heterocyclic ring which consists of 5- or 6-ring atoms and which may be substituted with halogen, alkyl or alkoxy having 1-4 C-atoms, and

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Weesp, Netherlands

Hans H Haeck