Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-03-01
1995-12-12
Springer, David B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D47108, A61K 3141
Patent
active
054751144
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to novel pyrazolotriazole derivatives or salts thereof which show an angiotensin II (to be referred to as AII hereinafter) antagonism.
BACKGROUND ART
AII, a physiologically active peptide which shows a strong pressor reaction, has been regarded as a causal substance of hypertension in various mammalian species.
There are a few known pathways for the formation of AII in the living body, including a typical pathway in which angiotensin I is formed from angiotensinogen by the action of an enzyme, renin, and then converted into AII by the action of an angiotensin converting enzyme (ACE). Since the compound of the present invention inhibits expression of functions AII by acting on the AII receptor, it is useful as an AII antagonist.
Examples of known AII antagonists include imidazole derivatives disclosed in European Patent No. 253,310.
DISCLOSURE OF THE INVENTION
The inventors of the present invention have created various types of compounds and subjected them to screening and, as the result, found pyrazolotriazole derivatives which have excellent anti-AII activity and whose chemical structure is different from those of the prior art compounds.
The pyrazolotriazole derivative of the present invention is represented by the following general formula. ##STR2## (Each symbol in the above formula means as follows; R.sup.1, R.sup.3 and R.sup.4 : one of them represents a hydrogen atom, a biphenylmethyl group having a tetrazolyl group which may be substituted by aralkyl, or a lower alkyl group, and each of the remaining two has no substituent, which may be substituted by aralkyl, a cycloalkyl group, or a lower alkyl group which may be substituted by hydroxyl, lower alkoxy, carboxyl or lower alkoxycarbonyl, and and each represents a hydrogen atom, a halogen atom, a biphenylmethyl group having a tetrazolyl group which may be substituted by aralkyl, a formyl group, a carboxyl group, an esterified carboxyl group, a cycloalkyl group, a lower alkoxy group, or a lower alkyl group which may be substituted by hydroxyl, formyl, carboxyl, lower alkoxy or lower alkoxycarbonyl, having a tetrazolyl group which may be substituted by aralkyl and the broken lines mean that the pyrazolotriazole ring forms three double bonds.)
The following describes the compound of the present invention in detail.
Unless otherwise indicated, the term "lower" as defined in the general formula means a straight or branched carbon chain having 1 to 6 carbon atoms.
In consequence, illustrative examples of the "lower alkyl group" include methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, tert-butyl, pentyl (amyl), iso-pentyl, neo-pentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1,2-dimethylpropyl, hexyl, iso-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and the like groups.
The lower alkyl group may be substituted with other substituent group. In the case of R.sup.2, such a substituent group is hydroxyl, a lower alkoxy, carboxyl or a lower alkoxycarbonyl.
In the case of R.sup.5 and R.sup.6, the substituent group is hydroxyl, formyl, carboxyl, a lower alkoxy or a lower alkoxycarbonyl.
An optional position of a lower alkyl group can be substituted with one or two of these substituent groups. Typical examples of substituent-containing lower alkyl groups include methoxymethyl, ethoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, methoxycarbonylmethyl, 1-methoxycarbonylethyl, ethoxycarbonylmethyl, 1-ethoxycarbonylethyl, carboxymethyl, 1-carboxyethyl, 2-carboxyethyl, 1-carboxypropyl, 2-carboxypropyl, 3-carboxypropyl, dimethoxymethyl, diethoxymethyl, 2,2-dimethoxyethyl, 2,2-diethoxyethyl, 3,3-dimethoxypropyl, 3,3-diethoxypropyl, 3,3-dipropoxypropyl, 4,4-dimethoxybutyl, 4,4-diethoxybutyl, 4,4-dipropoxybutyl, 5,5-dimethoxypentyl, 5,5-diethoxypentyl
Inagaki Osamu
Kikuchi Kazumi
Okazaki Toshio
Suga Akira
Watanabe Toshihiro
Springer David B.
Yamanouchi Pharmaceutical Co. Ltd.
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