US4130663A
Expired / Lapsed
US
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Styrylamidines
Assignee: Mead Johnson and Co LLC
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Filing: 1978-04-10
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Granted: 1978-12-19
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Expires: 1998-04-10
Abstract
Abstract Styrylamidines are prepared by treating styrylsulfonylamidines with base. The styrylamidines are effective in the prevention of aggregation of blood platelets and as analgesics. Compounds of the invention are also useful as anticonvulsants, diuretics, and antihypertensive agents. The styrylsulfonylamidines of the invention which serve as precursors to the styrylamidines also have analgesic properties. Illustrative of the styrylamidines of the present invention are 4-amino-N-(4-aminostyryl)benzamidine and N-(3,4-dichlorostyryl)acetamidine. An example of a styrylsulfonylamidine is N-(styrylsulfonyl)acetamidine.
Inventors
- 👤 William L. Matier
- 👤 William T. Comer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 09:00
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/13; A61K31/155
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
226 words
A method for preventing aggregation of blood platelets in a mammal having a thromboembolic condition which comprises administering to said mammal an antithrombogenic effective dose of a styrylamidine or a salt thereof of a pharmaceutically acceptable acid to provide a blood level of from 0.5 to 90 mcg. of said styrylamidine per 0.5 ml. blood, said styrylamidine being selected from the group consisting of the compounds having the formula ##STR9## wherein R 1 is selected from lower alkyl of 1 to 4 carbon atoms inclusive, hydrogen, nitro, amino, halogen, cyclohexyl, carbamoyl, lower alkylsulfonyl from 1 to 4 carbon atoms inclusive, sulfamoyl or lower alkanoylamido of from 2 to 4 carbon atoms inclusive; R 2 is selected from hydrogen or halogen with the proviso that when R 1 is halogen, R 2 can represent up to two additional halogen; R 3 is hydrogen, cyclopropyl or lower alkyl of 1 to 4 carbon atoms inclusive; A is selected from lower alkyl of from 1 to 8 carbon atoms inclusive, di(lower)alkylaminophenyl, phenyl, benzyl, β-naphthyl, styryl, phenylbutadienyl, cycloalkyl of 3 to 6 carbon atoms inclusive, or a substituted phenyl radical represented by the symbol ##STR10## wherein X is selected from (lower) alkoxy from 1 to 4 carbon atoms inclusive, halogen, nitro, amino, lower alkanoylamido of from 2 to 4 carbon atoms inclusive, and n represents the integer 1 or 2.
Claim 2
Independent Claim
226 words
A method for preventing aggregation of blood platelets in a mammal having a thromboembolic condition which comprises administering to said mammal an antithrombogenic effective dose of a styrylamidine or a salt thereof of a pharmaceutically acceptable acid to provide a blood level of from 0.5 to 90 mcg. of said styrylamidine per 0.5 ml. blood, said styrylamidine being selected from the group consisting of the compounds having the formula ##STR9## wherein R 1 is selected from lower alkyl of 1 to 4 carbon atoms inclusive, hydrogen, nitro, amino, halogen, cyclohexyl, carbamoyl, lower alkylsulfonyl from 1 to 4 carbon atoms inclusive, sulfamoyl or lower alkanoylamido of from 2 to 4 carbon atoms inclusive; R 2 is selected from hydrogen or halogen with the proviso that when R 1 is halogen, R 2 can represent up to two additional halogen; R 3 is hydrogen, cyclopropyl or lower alkyl of 1 to 4 carbon atoms inclusive; A is selected from lower alkyl of from 1 to 8 carbon atoms inclusive, di(lower)alkylaminophenyl, phenyl, benzyl, β-naphthyl, styryl, phenylbutadienyl, cycloalkyl of 3 to 6 carbon atoms inclusive, or a substituted phenyl radical represented by the symbol ##STR10## wherein X is selected from (lower) alkoxy from 1 to 4 carbon atoms inclusive, halogen, nitro, amino, lower alkanoylamido of from 2 to 4 carbon atoms inclusive, and n represents the integer 1 or 2.
Claim 3
Dependent Claim
18 words
The method as claimed in claim 1 employing N-(3,4-dichlorostyryl)acetamidine or a salt thereof of a pharmaceutically acceptable acid.
Claim 4
Dependent Claim
18 words
The method as claimed in claim 1 employing N-(3,4-dichlorostyryl)cyclopropanecarboxamidine or a salt thereof of a pharmaceutically acceptable acid.
Claim 5
Independent Claim
52 words
A method of producing an antihypertensive effect comprising systemic administration to a mammal in need thereof an effective dose of a styrylamidine of from about 0.01 to 100 mg./kg. body weight of said mammal to provide an antihypertensive effect, said styrylamidine selected from the group consisting of N-(2,6-dichlorostyryl)acetamidine, N-2,6-dichlorostyryl)propionamidine, N-(2,6-dichlorostyryl)cyclopropanecarboxamidine and N-methyl-N-(2,6-dichlorostyryl)acetamidine.
Claim 6
Independent Claim
52 words
A method of producing an antihypertensive effect comprising systemic administration to a mammal in need thereof an effective dose of a styrylamidine of from about 0.01 to 100 mg./kg. body weight of said mammal to provide an antihypertensive effect, said styrylamidine selected from the group consisting of N-(2,6-dichlorostyryl)acetamidine, N-2,6-dichlorostyryl)propionamidine, N-(2,6-dichlorostyryl)cyclopropanecarboxamidine and N-methyl-N-(2,6-dichlorostyryl)acetamidine.
Claim 7
Dependent Claim
191 words
An antithrombogenic or an antihypertensive composition in dosage unit form comprising a pharmaceutical carrier and a compound selected from the group consisting of styrylamidines having the formula ##STR11## and a salt thereof of a pharmaceutically acceptable acid wherein R 1 is selected from lower alkyl of 1 to 4 carbon atoms inclusive, hydrogen, nitro, amino, halogen, cyclohexyl, carbamoyl, lower alkylsulfonyl from 1 to 4 carbon atoms inclusive, sulfamoyl or lower alkanoylamido of from 2 to 4 carbon atoms inclusive; R 2 is hydrogen or halogen with the proviso that when R 1 is halogen, R 2 can represent up to two additional halogen; R 3 is hydrogen, cyclopropyl or lower alkyl of 1 to 4 carbon atoms inclusive; A is selected from lower alkyl of from 1 to 8 carbon atoms inclusive, di(lower)alkylaminophenyl, phenyl, benzyl, β-naphthyl, styryl, phenylbutadienyl, cycloalkyl of 3 to 5 carbon atoms inclusive, or a substituted phenyl radical represented by the symbol ##STR12## wherein X is selected from (lower)alkoxy from 1 to b 4 carbon atoms inclusive, halogen, nitro, amino, lower alkanoylamido of from 2 to 4 carbon atoms inclusive, and n represents the integer 1 or 2.
Claim 8
Dependent Claim
191 words
An antithrombogenic or an antihypertensive composition in dosage unit form comprising a pharmaceutical carrier and a compound selected from the group consisting of styrylamidines having the formula ##STR11## and a salt thereof of a pharmaceutically acceptable acid wherein R 1 is selected from lower alkyl of 1 to 4 carbon atoms inclusive, hydrogen, nitro, amino, halogen, cyclohexyl, carbamoyl, lower alkylsulfonyl from 1 to 4 carbon atoms inclusive, sulfamoyl or lower alkanoylamido of from 2 to 4 carbon atoms inclusive; R 2 is hydrogen or halogen with the proviso that when R 1 is halogen, R 2 can represent up to two additional halogen; R 3 is hydrogen, cyclopropyl or lower alkyl of 1 to 4 carbon atoms inclusive; A is selected from lower alkyl of from 1 to 8 carbon atoms inclusive, di(lower)alkylaminophenyl, phenyl, benzyl, β-naphthyl, styryl, phenylbutadienyl, cycloalkyl of 3 to 5 carbon atoms inclusive, or a substituted phenyl radical represented by the symbol ##STR12## wherein X is selected from (lower)alkoxy from 1 to b 4 carbon atoms inclusive, halogen, nitro, amino, lower alkanoylamido of from 2 to 4 carbon atoms inclusive, and n represents the integer 1 or 2.
Claim 9
Dependent Claim
20 words
The composition of claim 5 in which the active ingredient is N-(3,4-dichlorostyryl)cyclopropanecarboxamidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
20 words
The composition of claim 5 in which the active ingredient is N-(3,4-dichlorostyryl)acetamidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
20 words
The composition of claim 5 in which the active ingredient is N-(2,6-dichlorostyryl)acetamidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
20 words
The composition of claim 5 in which the active ingredient is N-(2,3,6-trichlorostyryl)acetamidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Dependent Claim
20 words
The composition of claim 5 in which the active ingredient is N-(2-chloro-6-methylstyryl)acetamidine or a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
US3413345A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-18 | 1982-06-19 | 1982-12-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-18 | 1986-06-19 | 1986-12-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-18 | 1990-06-19 | 1990-12-19 | $7700.00 | Window Closed / Lapsed |