Pyrimidine derivatives as endothelin antagonists

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

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514211, 514218, 514255, 514269, 514272, 540544, 540575, 544123, 544298, 544319, 544321, C07D41304, C07D40304, A61K 31505, A61K 31535

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active

058830928

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to novel pyrimidine derivatives and their salts, and to pharmaceuticals containing these compounds as active ingredients.


BACKGROUND ART

Endothelin, having potent vasoconstrictive effect and blood pressure elevating effect, is considered to be a substance that contributes to various diseases and disorders including heart diseases such as ischemic heart infarction, congestive heart failure, arrhythmia, and unstable angina; airway diseases such as asthma; hypertonia such as pulmonary hypertension and renal hypertension; hypofunctions of organs which may occur in association with operation or transplantation thereof; circulatory diseases such as subarachnoid hemorrhage, post-PTCA reconstriction, and vasospasm; kidney diseases such as acute and chronic renal failure; diabetes, hyperlipemia, and other diseases that are accompanied by vascular lesion; arteriosclerosis; liver diseases such as alcohol-induced liver disorders; gastrointestinal disorders such as those of gastric mucosa; bone diseases; prostatic hypertrophy; and urinary Up-to-date"), 94, 335-431 (1994), Igaku-no-Ayumi (may be translated to "Progress of Medicine"), 168, 675-692 (1994), Igaku-no-Ayumi, 170, 357 (1994)!.
It has come to be elucidated that a variety of actions of endothelin are triggered upon binding of endothelin to its receptors in organs of the body, and that the vasoconstriction caused by endothelin is induced by the mediation of at least two different receptors (ET.sub.A and ET.sub.B receptors). Therefore, a compound that prevents endothelin from binding to these two receptors should be useful as a preventive and therapeutic agent for the above-mentioned diseases in which endothelin participates. Heretofore, a number of compounds have been reported as exhibiting (1993), Circulation, 88, 1-316 (1994), Saishin-Igaku, 94, 424-431 (1994), J. Med. Chem. 37, 1553 (1994), and Japanese Patent Application Laid-Open (kokai) Nos. 5-222003, 6-211810, 7-17972, and 8-99961)!.
However, no compound has yet been found to exhibit satisfactory endothelin antagonism.
Accordingly, the present invention is directed to the discovery of a compound that has potent endothelin antagonism, as well as to the provision of pharmaceuticals containing such a compound as the active ingredient.


DISCLOSURE OF THE INVENTION

Under the above circumstances, the present inventors carried out careful studies, and found that the pyrimidine derivatives represented by the following formula (1) and their salts exhibit excellent endothelin antagonism and thus are useful as medicines--particularly those for circulatory diseases. The present invention was accomplished based on this finding.
Accordingly, the present invention provides a pyrimidine derivative of the following formula (1) or a salt thereof: ##STR2## phenyloxy group which may have a substituent, an aralkyloxy group which may have a substituent, or --NR.sup.2 R.sup.3 ; X represents an oxygen atom or N--R.sup.4 ; m is 2 or 3; and n is 1 or 2 (wherein each of R.sup.2 and R.sup.3, which are identical to or different from each other, represents a hydrogen atom, a hydroxyl group, a lower alkyl group which may have a substituent, a phenyl group which may have a substituent, an aralkyl group which may have a substituent, or a heterocyclic group which may have a substituent; R.sup.4 represents a lower alkyl group, a phenyl group, a formyl group, or a lower alkoxycarbonyl group)!.
The present invention also provides a medicine containing a pyrimidine derivative of formula (1) or a salt thereof as an active ingredient.
The present invention also provides a pharmaceutical composition containing a pyrimidine derivative of formula (1) or a salt thereof and a pharmaceutically acceptable carrier.
The present invention also provides use as a medicine of a pyrimidine derivative of formula (1) or a salt thereof.
The present invention also provides a method for treating and preventing diseases induced by endothelin, wherein the method is characterized by administering to a patient an ef

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