3-Amino-5-substituted-6-halo-N-(4,4-disubs tituted-6-substituted-1,3,5-triazin-2-yl)-2-pyrazinecarboxamides
AssigneeMerck & Co., Inc.
InventorsOtto W. Woltersdorf, Jr., S. Jane deSolms, Robert L. Smith
Life of this patent
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Abstract
This invention relates to 3-amino-5-substituted-6-halo-N-(4,4-disubstituted-6-substituted-1,3,5-tria zin-2-yl)-2-pyrazinecarboxamides and processes for preparing same. The compounds are eukalemic/saluretic agents useful in the treatment of edema and hypertension.
Claims11
A compound of the formula or the tautomeric form thereof ##STR5## wherein R is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl;
- R.sup.1 is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl;
- R.sup.2 is C.sub.1-5 alkyl;
- R.sup.3 is C.sub.1-5 alkyl;
- R.sup.2 and R.sup.3 can be joined with the carbon atom to which they are attached to form a 3-7 membered carbon ring;
- X is halo;
- Y is OH, SH, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio and NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen or C.sub.1-5 alkyl and R.sup.5 is hydrogen, C.sub.1-5 alkyl, CN, CONH.sub.2, ##STR6## NO.sub.2 or NH.sub.2 and the pharmaceutical acid addition salts thereof.
A compound of the formula ##STR7## wherein R is hydrogen or C.sub.1-5 alkyl,
- R.sup.1 is hydrogen or C.sub.1-5 alkyl,
- R.sup.2 is methyl,
- R.sup.3 is methyl,
- X is chloro,
- Y is OH, SH, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
A pharmaceutical composition useful in the treatment of edema and hypertension which comprises in combination with a pharmaceutically acceptable carrier, a compound or the tautomeric form of the formula:
- ##STR8## wherein R is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl;
- R.sup.1 is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl;
- R.sup.2 is C.sub.1-5 alkyl;
- R.sup.3 is C.sub.1-5 alkyl;
- R.sup.2 and R.sup.3 can be joined with the carbon atom to which they are attached to form a 3-7 membered carbon ring;
- X is halo;
- Y is OH, SH, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio and NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen or C.sub.1-5 alkyl and R.sup.5 is hydrogen, C.sub.1-5 alkyl, CN, CONH.sub.2, ##STR9## NO.sub.2 or NH.sub.2 and the pharmaceutical acid addition salts thereof.
A pharmaceutical composition useful in the treatment of edema and hypertension which comprises in combination with a pharmaceutically acceptable carrier, a compound or the tautomeric form of the formula:
- ##STR10## wherein R is hydrogen or C.sub.1-5 alkyl,
- R.sup.1 is hydrogen or C.sub.1-5 alkyl,
- R.sup.2 is methyl,
- R.sup.3 is methyl,
- X is chloro,
- Y is OH, SH, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
A method of treating edema or hypertension which comprises administering to a patient in need of such treatment a pharmaceutically effective amount of a compound of the formula:
- ##STR11## wherein R is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl;
- R.sup.1 is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl or C.sub.3-6 cycloalkyl;
- R.sup.2 is C.sub.1-5 alkyl;
- R.sup.3 is C.sub.1-5 alkyl;
- R.sup.2 and R.sup.3 can be joined with the carbon atom to which they are attached to form a 3-7 membered carbon ring;
- X is halo;
- Y is OH, SH, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio and NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen or C.sub.1-5 alkyl and R.sup.5 is hydrogen, C.sub.1-5 alkyl, CN, CONH.sub.2, ##STR12## NO.sub.2 or NH.sub.2 and the pharmaceutical acid addition salts thereof.
A method of treating edema or hypertension which comprises administering to a patient in need of such treatment a pharmaceutically effective amount of a compound of the formula:
- ##STR13## wherein R is hydrogen or C.sub.1-5 alkyl,
- R.sup.1 is hydrogen or C.sub.1-5 alkyl,
- R.sup.2 is methyl,
- R.sup.3 is methyl,
- X is chloro,
- Y is OH, SH, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.