US4331671A
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5-(Pyridinyl)-1H-benzimidazoles and 1-hydroxy-6-(pyridinyl)-1H-benzimidazoles and their cardiotonic use
Assignee: STWB Inc
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Filing: 1981-01-09
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Granted: 1982-05-25
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Expires: 2001-01-09
Abstract
Abstract 2-R-5-(Py-Y)-1H-benzimidazole or pharmaceutically-acceptable acid-addition salt thereof, useful as a cardiotonic, is prepared by reacting 4-(Py-Y)-1,2-benzenediamine with a tri-(lower-alkyl)ortho-(lower-alkanoate) of the formula R--C(OR 1 ) 3 , where R is hydrogen or lower-alkyl, Y is a direct linkage or lower-alkylene having one or two carbon atoms, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or with dimethylformamide dimethyl acetal or dimethylacetamide dimethyl acetal to produce said 2-R-5-(Py-Y)-1H-benzimidazole where R is methyl or ethyl respectively. The same compound where R is lower-alkyl is prepared in two steps by first reacting 4-(Py-Y)-1,2-benzenediamine with an alkanoylating agent providing alkanoyl of the formula ##STR1## to produce N 2 --[R'--C(═O)]-4-(Py-Y)-1,2-benzenediamine and heating the latter compound to produce said 2-R'-5-(Py-Y)-1H-benzimidazole, where R' is lower-alkyl. Also shown is 1-hydroxy-2-R-6-(Py-Y)-1H-benzimidazole or pharmaceutically-acceptable acid-addition salt thereof, useful as a cardiotonic and prepared by reacting 3-nitro-N-(RCO)-4-(Py-Y)-benzeneamine with hydrogen under catalytic hydrogen conditions.
Inventors
- 👤 George V. Lesher
- 👤 Baldev Singh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:48
CPC Classifications
C; C07; C07D; C07D403/00; C07D401/00; C07D401/02; C07D401/04; A; A61; A61P; A61P9/00; A61P9/04
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
46 words
2-R-5-(Py-Y)-1H-benzimidazole having the formula ##STR10## where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or a pharmaceutically-acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
46 words
2-R-5-(Py-Y)-1H-benzimidazole having the formula ##STR10## where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or a pharmaceutically-acceptable acid-addition salt thereof.
Claim 3
Dependent Claim
26 words
A compound according to claim 1 where Py is 4- or 3-pyridinyl, Y is a direct linkage or methylene, and R is hydrogen, methyl or ethyl.
Claim 4
Dependent Claim
5 words
5-(4-Pyridinyl)-1H-benzimidazole according to claim 2.
Claim 5
Dependent Claim
5 words
5-(2,6-Dimethyl-4-pyridinyl)-1H-benzimidazole according to claim 1.
Claim 6
Dependent Claim
5 words
2-Methyl-5-(4-pyridinyl)-1H-benzimidazole according to claim 2.
Claim 7
Dependent Claim
5 words
2-Ethyl-5-(4-pyridinyl)-1H-benzimidazole according to claim 2.
Claim 8
Dependent Claim
66 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, a cardiotonically-effective amount of 2-R-5-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 9
Dependent Claim
66 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, a cardiotonically-effective amount of 2-R-5-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 10
Dependent Claim
26 words
A composition according to claim 7 where Py is 4- or 3-pyridinyl, Y is a direct linkage or methylene, and R is hydrogen, methyl or ethyl.
Claim 11
Independent Claim
64 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering to such patient a cardiotonically-effective amount of 2-R-5-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 12
Independent Claim
64 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering to such patient a cardiotonically-effective amount of 2-R-5-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 13
Dependent Claim
26 words
The method according to claim 9 where Py is 4- or 3-pyridinyl, Y is a direct linkage or methylene, and R is hydrogen, methyl or ethyl.
Claim 14
Dependent Claim
46 words
1-Hydroxy-2-R-6-(Py-Y)-1H-benzimidazole having the formula ##STR11## where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or a pharmaceutically-acceptable acid-addition salt thereof.
Claim 15
Dependent Claim
46 words
1-Hydroxy-2-R-6-(Py-Y)-1H-benzimidazole having the formula ##STR11## where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or a pharmaceutically-acceptable acid-addition salt thereof.
Claim 16
Dependent Claim
26 words
A compound according to claim 11 where Py is 4- or 3-pyridinyl, Y is a direct linkage or methylene, and R is hydrogen, methyl or ethyl.
Claim 17
Dependent Claim
5 words
1-Hydroxy-6-(4-pyridinyl)-1H-benzimidazole according to claim 12.
Claim 18
Dependent Claim
5 words
1-Hydroxy-2-methyl-6-(4-Pyridinyl)-1H-benzimidazole according to claim 12.
Claim 19
Dependent Claim
65 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, cardiotonically-effective amount of 1-hydroxy-2-R-6-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 20
Dependent Claim
65 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, cardiotonically-effective amount of 1-hydroxy-2-R-6-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 21
Dependent Claim
26 words
A composition according to claim 15 where Py is 4- or 3-pyridinyl, Y is a direct linkage or methylene, and R is hydrogen, methyl or ethyl.
Claim 22
Independent Claim
64 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering to such patient a cardiotonically-effective amount of 1-hydroxy-2-R-6-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 23
Independent Claim
64 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering to such patient a cardiotonically-effective amount of 1-hydroxy-2-R-6-(Py-Y)-1H-benzimidazole or a pharmaceutically-acceptable acid-addition salt thereof, where Y is a direct linkage or lower-alkylene having one or two carbon atoms, R is hydrogen or lower-alkyl, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
Claim 24
Dependent Claim
26 words
The method according to claim 17 where Py is 4- or 3-pyridinyl, Y is a direct linkage or methylene, and R is hydrogen, methyl or ethyl.
References Cited (Backward Citations)
US4026936A
Cited
US4188486A
Cited
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