Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-09-27
1996-04-16
Ivy, C. Warren
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546300, 546304, 546306, 546309, 546311, 546312, 546315, 546318, 546322, 546326, 546330, C07D21382, A61K 3144
Patent
active
055082939
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP 93/00103, filed Jan. 28, 1993.
TECHNICAL FIELD
The present invention relates to novel pyridinecarboximidamide compounds having a vasodilating effect.
BACKGROUND ART
Prior to the accomplishment of the present invention, we found that various N-cyano-carboximidamide compounds had a hypotensive activity, a vasodilating effect and the like (as described in Japanese Laid-Open Patent Publications Nos. 163061/1991 and 218343/1991). However, more excellent novel antihypertensive or antianginal agents are strongly demanded when the various conditions of diseases, the quality of life, that is, the support and improvement of patients' daily life, side effects of drugs and the like are taken into consideration.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide novel compounds having a vasodilating effect, and more specifically compounds having an antihypertensive effect or an antianginal effect. The present invention has been accomplished on the basis of the finding that novel pyridinecarboximidamide compounds have a vasodilating effect.
The pyridinecarboximidamide compounds according to the present invention are represented by the following formula (I): ##STR2## wherein
when R.sup.1 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl R.sup.2 represents a hydrogen atom and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group; and
when R.sup.1 represents a hydrogen atom, represents R.sup.2 represents a hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl group and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group.
The present invention also relates to use of the compounds mentioned above. That is, the antihypertensive agent according to the present invention comprises as an active ingredient a pyridinecarboximidamide represented by formula (I) above or an acid adduct salt thereof, and the antianginal agent comprises as an active ingredient a pyridinecarboximidamide represented by formula (I) above wherein R.sup.3 is a nitroxyl group or an acid adduct salt thereof.
The present invention further relates to a method for treatment of hypertension characterized in that a pyridinecarboximidamide represented by formula (I) or an acid adduct salt thereof is administered to a patient who needs the treatment of hypertension and to a method for treatment of angina pectoris characterized in that a pyridinecarboximidamide represented by formula (I) wherein R.sup.3 is a nitroxy group or an acid adduct salt thereof is administered to a patient of angina pectoris.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a reaction scheme for producing the compound of the present invention represented by the formula (I) and illustrates the production of the N-cyano-pyridinecarboximidamide compound represented by the formula (I) in which R.sup.1 represents an alkyl group, a hydroxyalkyl group, a carboxyl group, an amino group, an alkylamino group, a dialkylamino group, an aralkylamino group or a hydroxyl group, and R.sup.2 represents a hydrogen atom; or R.sup.1 represents a hydrogen atom, and R.sup.2 represents an amino group or a dialkylamino group, and an acid adduct salt thereof.
FIG. 2 is a reaction scheme for the production of the compound of the present invention represented by the formula (I) and illustrates the production of the N-ecyano-pyridinecarboximidamide compound in which R.sup.1 represents an acylamino group, an alkylsulfonamide group or bisalkylsulfonylamino group, and an acid adduct salt thereof.
BEST MODE FOR CARRYING OUT THE INVENTION PYRIDINECARBOXIMIDAMIDE COMPOUNDS
As described above, the pyridinecarboximidamide compounds according to the present invention are represented by the following formula (I): ##STR3## wherein
when R.sup.1 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide,
REFERENCES:
Kashiwabara, T. et al., Eur. J. Pharmacol., 196(1), 1-7 (1991).
Okada, Y. et al., Br. J. Pharmacol., 104(4), 829-838 (1991).
Ohta, H. et al., Eur. J. Pharmacol., 204(2), 171-177 (1991).
Sakuta, H. et al., Br. J. Pharmacol., 107(4), 1061-1067 (1992).
Ishibashi, T. et al., Naunyn-Schmiedebergs Arch Pharmacol, 346(1), 94-101 (1992).
Jinno, Y. et al., Br. J. Pharmacol, 106(4), 906-909 (1992).
Ogawa, N. et al., J. Cardiovasc. Pharmacol., 20(1), 11-17 (1992).
Ogawa, N. et al., Arch. Int. Parmacodyn Ther., 318, 36-46 (1992).
Kaneta, S. et al., Arch Int. Pharmacodyn Ther., 318, 21-35 (1992).
Yamagishi, T. et al., Naunyn-Schmiedebergs Arch Pharmacol., 346(6), 691-700 (1992).
Kaneta Soichiro
Kashiwabara Tomoko
Nakajima Tatsuo
Ogawa Nobuyuki
Okawara Hideki
Davis Zinna N.
Ivy C. Warren
Kirin Beer Kabushiki Kaisha
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