1H- and 2H- indazole derivatives

Details 1H- and 2H- indazole derivatives 1H- and 2H- indazole derivatives

1982-04-28

1984-03-13

Schwartz, Richard A.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

424251, 424273R, 544298, 544320, 544321, 544331, 548371, 548372, C07D40312

Patent

active

044369131

DESCRIPTION:

BRIEF SUMMARY
SUMMARY OF THE INVENTION

This invention relates to 1H- and 2H-indazole derivatives of the formula ##STR2## and their acid addition salts wherein formula I, R1 represents hydrogen, a lower alkyl, a lower aralkyl or an aryl group and is bound to one or both nitrogen atoms in the 1 or 2 position, wherein the aryl group and the aryl portion or the aralkyl group may be individually or multiply substituted, uniformly or differently, with a R4 group. group, a lower alkyl group, a lower alkoxy group or a lower alkylthio group, and the secondary or tertiary amino groups ##STR3## provided that at least one of the R or R4 groups is one of the aforementioned secondary or tertiary amino groups and R, in the 4 or 7 position, also represents one of the noted secondary or tertiary amino groups for the 1H-indazole derivatives only when the R1 group is simultaneously an aryl oraralkyl group, and wherein R5 represents hydrogen, an hydroxyl group or a lower alkyl or alkoxy group.
This invention further relates to the utilization of the aforementioned substances as active blood-pressure lowering substances for the manufacture of pharmaceuticals for animal and human medicine.


DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The way of writing the indazole ring system in formula I means that the 1H-indazole derivatives ##STR4## as well as the 2H-indazole derivatives ##STR5## are to be understood by formula I.
The expression "lower" in combination with alkyl groups or alkyl portions in other groups, especially in the alkoxy and aralkyl groups, designates alkyl groups or alkyl portions with up to 6 carbon atoms, wherein these alkyls may also be cycloalkyls. Preferably, the expression "lower", in this connection, represents saturated, branched or unbranched acyclical carbon groups with up to 4 carbon atoms total.
Of course, only pharmacologically acceptable acid addition salts, especially hydrochlorides and nitrates, are employed in the manufacture of medicines.
Tautomerism is observed with respect to the R group for the 2-imidazolin-2-yl-derivatives and the imidazolidine derivatives as well as for the 3,4,5,6-tetrahydropyrimidine derivatives and the hexahydropyrimidine derivatives.
The R group is preferably a 2-imidazolin-2-yl-amino group (or its tautomers) or a chlorine atom, wherein in the latter case, the R4 group may be a 2-imidazolin-2-yl-phenyl- or -benzyl group that may be additionally substituted by chlorine. The R1 group is preferably a methyl group or possibly a substituted benzyl group, while the R2 and R3 groups preferably each represent one hydrogen atom.
The following substances and their addition salts have special significance: 6-(2-imidazolin-2-yl-amino)-1-methyl-1H-indazole, 4-(2-imidazolin-2-yl-amino)-2-methyl-2H-indazole, 4-(2-imidazolin-2-yl-amino)-2-benzyl-2H-indazole and 5-(2-imidazolin-2-yl-amino)-1-methyl-1H-indazole.
The indazoles of formula I can be produced by many different processes.
One method for producing the indazoles of formula I, when R is not a halogen, is characterized in that a correspondingly substituted indazole, which carries an amino group in the position of the benzene ring into which the R group is to be introduced, is condensed with a compound of the formula ##STR6## wherein X is a group that is splittable with hydrogen under condensation conditions, preferably a halogen, especially chlorine, and Ac is an acyl group, especially a lower alkyl acyl group or a substituted or unsubstituted phenyl acyl group. Q represents an ethylene or propylene group herein.
If a compound of formula IIa is used as a starting substance for this condensation, then such substance is preferably introduced in the form of a free base in the presence of a polar or non-polar solvent. Alcohols, ether or chlorinated hydrocarbons serve as solvents. Condensation proceeds in a temperature range between room temperature and about 150.degree. C. The precipitated product, in the form of a salt, is separated and worked up.
When substituent X in formula IIa is an alkylthio group or a nitroamino group, then the substan

REFERENCES:
patent: 3847934 (1974-11-01), Neumann
patent: 4036976 (1977-07-01), Neumann

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