US4057636A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antihypertensive pyridylguanidine compounds
Assignee: Leo Pharma AS
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Filing: 1975-12-01
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Granted: 1977-11-08
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Expires: 1995-12-01
Abstract
Abstract The invention relates to a series of new compounds, to methods for preparing the compounds, to compositions containing said compounds which are useful in the human and veterinary medical practice, and to methods for treating patients suffering from certain illnesses with said compounds, the new compounds having the general formula I <IMAGE> I or the tautomeric forms thereof in which the R1-substituted cyano-guanidyl radical is placed in the 2-, 3- or 4-position of the pyridine ring, and in which R1 stands for a straight or branched, saturated or unsaturated, aliphatic hydrocarbon radical having from 1 to 8 carbon atoms, a cycloalkyl or cycloalkenyl radical having from 3 to 7 carbon atoms, an aryl or an aralkyl radical, and R2 stands for hydrogen, halogen, hydroxy, lower alkyl or alkoxy radicals; and in the case of the present compounds containing one or more asymmetric carbon atoms, also the stereoisomers thereof and racemic mixtures of same; and salts of the compounds of formula I with nontoxic, pharmaceutically acceptable acids.
Inventors
- 👤 Hans Jorgen Petersen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 02:01
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/38; A; A61; A61P; A61P9/00; A61P9/12; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/75
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
84 words
A compound of the formula I ##STR9## or the tautomeric forms thereof in which the R 1 -substituted cyano-guanidyl radical is placed in the 2-, 3- or 4-position of the pyridine ring, and in which R 1 stands for aliphatic hydrocarbon having from 1 to 8 carbon atoms, cycloalkyl having from 3 to 8 carbon atoms, phenyl, benzyl or phenethyl, and R 2 stands for hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy radicals, or a salt thereof with a non-toxic, pharmaceutically acceptable acid.
Claim 2
Dependent Claim
84 words
A compound of the formula I ##STR9## or the tautomeric forms thereof in which the R 1 -substituted cyano-guanidyl radical is placed in the 2-, 3- or 4-position of the pyridine ring, and in which R 1 stands for aliphatic hydrocarbon having from 1 to 8 carbon atoms, cycloalkyl having from 3 to 8 carbon atoms, phenyl, benzyl or phenethyl, and R 2 stands for hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy radicals, or a salt thereof with a non-toxic, pharmaceutically acceptable acid.
Claim 3
Dependent Claim
23 words
A compound according to claim 1 in which the R 1 -substituted cyano-guanidyl radical is placed in the 3-position of the pyridine ring.
Claim 4
Dependent Claim
23 words
A compound according to claim 1, in which the R 1 -substituted cyano-guanidyl radical is placed in the 4-position of the pyridine ring.
Claim 5
Dependent Claim
28 words
A compound according to claim 1, in which R 1 is selected from the group consisting of isopropyl, isobutyl, sec-butyl, tert-butyl, branched pentyl, branched hexyl and branched heptyl.
Claim 6
Dependent Claim
17 words
A compound as defined in claim 1 which is N-tert-butyl-N"-cyano-N'-3-pyridylguanidine; or a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.
Claim 7
Dependent Claim
17 words
A compound as defined in claim 1 which is N"-cyano-N-tert-pentyl-N'-3-pyridylguanidine; or a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.
Claim 8
Dependent Claim
17 words
A compound as defined in claim 1 which is N"-cyano-N-(1-ethyl-1-methylpropyl)-N'-3-pyridylguanidine; or a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.
Claim 9
Dependent Claim
17 words
A compound as defined in claim 1 which is N"-cyano-N-3-pyridyl-N'-1,1,2-trimethylpropylguanidine; or a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.
Claim 10
Dependent Claim
17 words
A compound as defined in claim 1 which is N"-cyano-N-(1,1-diethylpropyl)-N'-3-pyridylguanidine; or a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.
Claim 11
Dependent Claim
17 words
A compound as defined in claim 1 which is N"-cyano-N-neopentyl-N'-3-pyridylguanidine; or a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.
Claim 12
Dependent Claim
15 words
A compound according to claim 1 wherein R 1 is either saturated hydrocarbon or ##STR10##
Claim 13
Dependent Claim
29 words
A composition for the treatment of hypertension containing as an active component, an effective amount of at least one compound according to claim 1, together with a carrier therefor.
Claim 14
Dependent Claim
15 words
A composition according to claim 12, which contains at least 0.1% of the active compound.
Claim 15
Dependent Claim
30 words
A composition according to claim 12 containing at least 0.1% of said compound in combination with another therapeutic compound applied in the treatment of hypertension, together with a pharmaceutical carrier.
Claim 16
Dependent Claim
21 words
A composition according to claim 14, which also contains an effective amount of a β-adrenergic blocker, a diuretic, reserpine, or α-methyldopa.
Claim 17
Dependent Claim
15 words
A composition according to claim 14, which contains an effective amount of a β-adrenergic blocker.
Claim 18
Independent Claim
100 words
A method of treating a human suffering from hypertension which comprises administering an effective amount of a compound of the formula I ##STR11## or the tautomeric forms thereof in which the R 1 -substituted cyano-guanidyl radical is placed in the 2-, 3- or 4-position of the pyridine ring, and in which R 1 stands for aliphatic hydrocarbon having from 1 to 8 carbon atoms, cycloalkyl having from 3 to 8 carbon atoms, phenyl, benzyl or phenethyl, and R 2 stands for hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy radicals; or a salt thereof with a non-toxic, pharmaceutically acceptable acid.
Claim 19
Independent Claim
100 words
A method of treating a human suffering from hypertension which comprises administering an effective amount of a compound of the formula I ##STR11## or the tautomeric forms thereof in which the R 1 -substituted cyano-guanidyl radical is placed in the 2-, 3- or 4-position of the pyridine ring, and in which R 1 stands for aliphatic hydrocarbon having from 1 to 8 carbon atoms, cycloalkyl having from 3 to 8 carbon atoms, phenyl, benzyl or phenethyl, and R 2 stands for hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy radicals; or a salt thereof with a non-toxic, pharmaceutically acceptable acid.
Claim 20
Dependent Claim
30 words
A method as claimed in claim 17, in which the compound is administered to an adult in dosage units containing not less than 0.01 mg and up to 1000 mg.
Claim 21
Dependent Claim
22 words
A method as claimed in claim 18 wherein the compound is administered in a dosage unit of from 0.02 to 200 mg.
References Cited (Backward Citations)
US3036083A
Cited
US3897444A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-11-07 | 1981-05-09 | 1981-11-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-07 | 1985-05-09 | 1985-11-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-07 | 1989-05-09 | 1989-11-08 | $7700.00 | Window Closed / Lapsed |