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Substituted 1H-indazole-3-carboxamides
| Details |
Inventors: Hamminga, Derk; van Wijngaarden, Ineke;
Assignee: Duphar International Research B.V. (Weesp, NL)
Primary Examiner: Lee; Mary C.
Assistant Examiner: McKane; Joseph K.
Attorney, Agent or Firm: Stevens, Davis, Miller & Mosher
The present invention is concerned with compounds of formula 1: ##STR1## wherein R.sub.1 is straight or branched alkyl having 1-4 C-atoms, halogen or cyano; n has the value 0-1; R.sub.2 is hydrogen, (1-6 C)alkyl, (3-6 C)alkenyl, (3-6 C)alkenyl, (3-6 C)cycloalkyl, (3-6 C)cycloalkyl-(1-4 C) alkyl, phenyl, phenyl-(1-3 C)alkyl, COOR.sub.6, COR.sub.6, CONR.sub.6 R.sub.7 or SO.sub.2 --R.sub.6, wherein R.sub.6 and R.sub.7 independently of each other are hydrogen, (1-6 C)alkyl, (3-6 C)cycloalkyl, phenyl or phenyl-(1-4 C)alkyl, wherein the benzene ring is optionally substituted with a methyl group or a halogen atom, with the proviso that R.sub.6 is not hydrogen when R.sub.2 is a group COOR.sub.6 or SO.sub.2 R.sub.6 ; R.sub.3 is hydrogen, straight or branched (1-6 C)alkyl or a phenyl-(1-3 C)alkyl group optionally substituted in the benzene ring; and A is a group of formula 2 or 3 ##STR2## wherein one of the groups R.sub.8, R.sub.9 and R.sub.10 is hydrogen, (1-C)alkyl, (3-6 C)cycloalkyl, (3-4 C)alkenyl or (3-4 C)alkynyl and the two other groups, independently of each other, are hydrogen or (1-4 C)alkyl, and the pharmacologically acceptable acid addition salts thereof, which are pharmaceutically useful as strong and selective antagonists of "neuronal" 5-hydroxy tryptamine (5-HT) receptors. |
|
DETAILED DESCRIPTION We claim: 1.
Compounds of formula 1: ##STR14## wherein R.
sub.
1 is straight or branched alkyl having 1-4 C-atoms, halogen or cyano; n has the value 0-1; R.
sub.
2 is hydrogen, (1-6 C)alkyl, (3-6 C)alkenyl, (3-6 C)cycloalkyl, (3-6 C)cycloalkyl-(1-4 C)alkyl, phenyl, phenyl-(1-3 C)alkyl, COOR.
sub.
6, COR.
sub.
6, CONR.
sub.
6 R.
sub.
7 or SO.
sub.
2 --R.
sub.
6, wherein R.
sub.
6 and R.
sub.
7 independently of each other are hydrogen, (1-6 C)alkyl, (3-6 C)cycloalkyl, phenyl or phenyl-(1-4 C)alkyl, wherein the benzene ring is optionally substituted with a methyl group or a halogen atom, with the proviso that R.
sub.
6 is not hydrogen when R.
sub.
2 is a group COOR.
sub.
6 or SO.
sub.
2 R.
sub.
6 ; R.
sub.
3 is hydrogen, straight or branched (1-6 C)alkyl or a phenyl-(1-3 C)alkyl group optionally substituted in the benzene ring; and A is a group of formula 2 or 3 ##STR15## wherein one of the groups R.
sub.
8, R.
sub.
9 and R.
sub.
10 is hydrogen, (1-4 C)alkyl, (3-6 C)cycloalkyl, (3-4 C)alkenyl or (3-4 C)alkynyl and the two other groups, independently of each other, are hydrogen or (1-4 C)alkyl, or a pharmacologically acceptable acid addition salt thereof.
2.
Pharmaceutical compositions which comprise a compound as claimed in claim 1 as the active substance.
3.
A method of treating syndromes caused by serotonin, by administering an effective amount of a compound as claimed in claim 1.
Description:
The invention relates to new 1H-indazole-3-carboxamides in which the amide-nitrogen atom is substituted with an imidazolyl methyl group.
It is known, inter alia from European Patent Application 86302964.
1 (publication no.
0.
200.
444) that certain indazole carboxylic acid derivatives are 5HT-antagonists which may be used for the treatment of serotonin-induced syndromes.
It has been found surprisingly that the new compounds of formula I ##STR3## wherein R.
sub.
1 is halogen, cyano or straight or branched alkyl having 1-4 C-atoms; n has the value 0-1; R.
sub.
2 is hydrogen, (1-6 C)alkyl, (3-6 C)alkenyl, (3-6 C)alkynyl, (3-6 C)cycloalkyl, (3-6 C)cycloalkyl-(1-4 C)alkyl, phenyl, phenyl-(1-3 C)alkyl, COOR
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Vasodialators 
