US4052455A
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Styrylamidines
Assignee: Mead Johnson and Co LLC
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Filing: 1975-08-04
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Granted: 1977-10-04
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Expires: 1995-08-04
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 10:57
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/13; A61K31/155
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
175 words
A compound selected from the group consisting of styrylamidines having the formula ##STR9## 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 cabon 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## 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
Dependent Claim
175 words
A compound selected from the group consisting of styrylamidines having the formula ##STR9## 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 cabon 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## 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
29 words
The compound according to claim 1 being a member selected from the group consisting of N-styrylamidines wherein A is methyl and a salt thereof of a pharmaceutically acceptable acid.
Claim 4
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(4-chlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 5
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 6
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)propionamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 7
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)butyramidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 8
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)pentanamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 9
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)-2-methylpropionamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 10
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorophenyl)-3-methylbutyramidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 11
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)-2,2-dimethylpropionamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 12
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)cyclopropane-carboxamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 13
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 14
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)propionamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 15
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)butyramidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 16
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)-2-methylpropionamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 17
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)-2,2-dimethylpropionamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 18
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)cyclopropane-carboxamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 19
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,4-dichlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 20
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(4-nitrostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 21
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2-nitrostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 22
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3-bromo-4-cyclohexylstyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 23
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(styryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 24
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)phenylacetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 25
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)phenylacetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 26
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-styrylbenzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 27
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 28
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,6-dichlorostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 29
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(3,4-dichlorostyryl)-3,4-dimethoxy-benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 30
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(4-acetamidostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 31
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2-aminostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 32
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 33
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(4-aminostyryl)sbenzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 34
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(4-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 35
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 3-nitro-N-(4-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 36
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 3-amino-N-(4-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 37
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 3-amino-N-(4-aminostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 38
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 4-nitro-N-(4-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 39
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 4-amino-N-(4-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 40
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 4-amino-N-(4-aminostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 41
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 3,5-diamino-N-(4-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 42
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 3,5-diamino-N-(4-aminostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 43
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of 4-(dimethylamino)-N-(4-nitrostyryl)-benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 44
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-methyl-N-(4-nitrostyryl)benzamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 45
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(4-aminostyryl)-2-naphthamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 46
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(4-nitrostyryl)cinnamamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 47
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-methyl-N-(2,6-dichlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 48
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-methyl-N-(3,4-dichlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 49
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2-chlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 50
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2-chloro-6-methylstyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
Claim 51
Dependent Claim
25 words
The compound according to claim 1 being a member selected from the group consisting of N-(2,3,6-trichlorostyryl)acetamidine and a salt thereof of a pharmaceutically acceptable acid.
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) | 1980-10-03 | 1981-04-04 | 1981-10-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-03 | 1985-04-04 | 1985-10-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-03 | 1989-04-04 | 1989-10-04 | $7700.00 | Window Closed / Lapsed |