US4272537A
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US
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3-Amino-5-substituted-6-halo-N-(4,4-disubstituted-6-substituted-1,3,5-triazin-2-yl)-2-pyrazinecarboxamides
Assignee: Merck and Co Inc
•
Filing: 1980-07-02
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Granted: 1981-06-09
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Expires: 2000-07-02
Abstract
Abstract This invention relates to 3-amino-5-substituted-6-halo-N-(4,4-disubstituted-6-substituted-1,3,5- triazin-2-yl)-2-pyrazinecarboxamides and processes for preparing same. The compounds are eukalemic/saluretic agents useful in the treatment of edema and hypertension.
Inventors
- 👤 Otto W. WOLTERSDORF, Jr.
- 👤 S. Jane deSolms
- 👤 Robert L. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:27
CPC Classifications
C; C07; C07D; C07D251/00; C07D251/02; C07D251/10
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
127 words
A compound of the formula or the tautomeric form thereof ##STR5## wherein R is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 1 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 2 is C 1-5 alkyl; R 3 is C 1-5 alkyl; R 2 and R 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 1-5 alkoxy, C 1-5 alkylthio and NR 4 R 5 wherein R 4 is hydrogen or C 1-5 alkyl and R 5 is hydrogen, C 1-5 alkyl, CN, CONH 2 , ##STR6## NO 2 or NH 2 and the pharmaceutical acid addition salts thereof.
Claim 2
Dependent Claim
127 words
A compound of the formula or the tautomeric form thereof ##STR5## wherein R is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 1 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 2 is C 1-5 alkyl; R 3 is C 1-5 alkyl; R 2 and R 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 1-5 alkoxy, C 1-5 alkylthio and NR 4 R 5 wherein R 4 is hydrogen or C 1-5 alkyl and R 5 is hydrogen, C 1-5 alkyl, CN, CONH 2 , ##STR6## NO 2 or NH 2 and the pharmaceutical acid addition salts thereof.
Claim 3
Dependent Claim
51 words
A compound of the formula ##STR7## wherein R is hydrogen or C 1-5 alkyl, R 1 is hydrogen or C 1-5 alkyl, R 2 is methyl, R 3 is methyl, X is chloro, Y is OH, SH, C 1-5 alkoxy, C 1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
51 words
A compound of the formula ##STR7## wherein R is hydrogen or C 1-5 alkyl, R 1 is hydrogen or C 1-5 alkyl, R 2 is methyl, R 3 is methyl, X is chloro, Y is OH, SH, C 1-5 alkoxy, C 1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
8 words
A compound of claim 2 which is 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-methylthio-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide.
Claim 6
Dependent Claim
9 words
A compound of claim 2 which is 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-mercapto-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide hydrochloride.
Claim 7
Dependent Claim
8 words
A compound of claim 2 which is 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-cyanoamino-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide.
Claim 8
Dependent Claim
8 words
A compound of claim 2 which is 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-ethoxy-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide.
Claim 9
Dependent Claim
8 words
A compound of claim 2 which is 3,5-diamino-6-chloro-N-(3,4-dihydro-4,4-dimethyl-6-hydroxy-1,3,5-triazin-2-yl)-2-pyrazinecarboxamide.
Claim 10
Dependent Claim
146 words
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 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 1 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 2 is C 1-5 alkyl; R 3 is C 1-5 alkyl; R 2 and R 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 1-5 alkoxy, C 1-5 alkylthio and NR 4 R 5 wherein R 4 is hydrogen or C 1-5 alkyl and R 5 is hydrogen, C 1-5 alkyl, CN, CONH 2 , ##STR9## NO 2 or NH 2 and the pharmaceutical acid addition salts thereof.
Claim 11
Dependent Claim
146 words
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 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 1 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 2 is C 1-5 alkyl; R 3 is C 1-5 alkyl; R 2 and R 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 1-5 alkoxy, C 1-5 alkylthio and NR 4 R 5 wherein R 4 is hydrogen or C 1-5 alkyl and R 5 is hydrogen, C 1-5 alkyl, CN, CONH 2 , ##STR9## NO 2 or NH 2 and the pharmaceutical acid addition salts thereof.
Claim 12
Dependent Claim
75 words
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 1-5 alkyl, R 1 is hydrogen or C 1-5 alkyl, R 2 is methyl, R 3 is methyl, X is chloro, Y is OH, SH, C 1-5 alkoxy, C 1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
75 words
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 1-5 alkyl, R 1 is hydrogen or C 1-5 alkyl, R 2 is methyl, R 3 is methyl, X is chloro, Y is OH, SH, C 1-5 alkoxy, C 1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
Claim 14
Independent Claim
145 words
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 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 1 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 2 is C 1-5 alkyl; R 3 is C 1-5 alkyl; R 2 and R 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 1-5 alkoxy, C 1-5 alkylthio and NR 4 R 5 wherein R 4 is hydrogen or C 1-5 alkyl and R 5 is hydrogen, C 1-5 alkyl, CN, CONH 2 , ##STR12## NO 2 or NH 2 and the pharmaceutical acid addition salts thereof.
Claim 15
Independent Claim
145 words
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 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 1 is hydrogen, C 1-5 alkyl, C 2-5 alkenyl or C 3-6 cycloalkyl; R 2 is C 1-5 alkyl; R 3 is C 1-5 alkyl; R 2 and R 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 1-5 alkoxy, C 1-5 alkylthio and NR 4 R 5 wherein R 4 is hydrogen or C 1-5 alkyl and R 5 is hydrogen, C 1-5 alkyl, CN, CONH 2 , ##STR12## NO 2 or NH 2 and the pharmaceutical acid addition salts thereof.
Claim 16
Independent Claim
74 words
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 1-5 alkyl, R 1 is hydrogen or C 1-5 alkyl, R 2 is methyl, R 3 is methyl, X is chloro, Y is OH, SH, C 1-5 alkoxy, C 1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
Claim 17
Independent Claim
74 words
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 1-5 alkyl, R 1 is hydrogen or C 1-5 alkyl, R 2 is methyl, R 3 is methyl, X is chloro, Y is OH, SH, C 1-5 alkoxy, C 1-5 alkylthio or cyanoamino and the pharmaceutically acceptable salts thereof.
References Cited (Backward Citations)
US3840538A
Cited
US4085211A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-06-08 | 1984-12-08 | 1985-06-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-08 | 1988-12-08 | 1989-06-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-08 | 1992-12-08 | 1993-06-09 | $7700.00 | Window Closed / Lapsed |