US4335132A
Expired / Lapsed
US
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5-(Py-Y)-1H-benzimidazol-2-ols and 5-(Py-Y-)-1H-benzimidazole-2-thiols
Assignee: STWB Inc
•
Filing: 1980-12-29
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Granted: 1982-06-15
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Expires: 2000-12-29
Abstract
Abstract 5-(Py-Y)-1H-benzimidazol-2-ol or 5-(Py-Y)-1H-benzimidazole-2-thiol or lower-alkyl ethers or thioethers thereof or pharmaceutically-acceptable acid-addition salts thereof, useful as cardiotonics, are prepared by reacting 4-(Py-Y)-1,2-benzenediamine with urear or carbonyldiimidazole to produce 5-(Py-Y)-1H-benzimidazol-2-ol or with thiourea, an alkali metal lower-alkyl xanthate or thiocarbonyldiimidazole to produce 5-(Py-Y)-1H-benzimidazole-2-thiol and by reacting 5-(Py-Y)-1H-benzimidazole-2-thiol with a lower-alkylating agent to produce 2-(lower-alkylthio)-5-(Py-Y)-1H-benzimidazole. 2-(Lower-alkoxy)-5-(Py-Y)-1H-benzimidazole is prepared by reacting 4-(Py-Y)-1,2-benzenediamine with tetra-(lower-alkoxy)methane.
Inventors
- 👤 George Y. Lesher
- 👤 Baldev Singh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:55
CPC Classifications
C; C07; C07D; C07D401/00; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; A; A61; A61P; A61P9/00; A61P9/04; C07D213/38
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
61 words
5-(Py-Y)-1H-benzimidazol-2-ol or 5-(Py-Y)-1H-benzimidazole-2-thiol or lower-alkyl ether or thioether thereof having the formula ##STR6## where Z is O or S, 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 1-oxide thereof, or pharmaceutically-acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
61 words
5-(Py-Y)-1H-benzimidazol-2-ol or 5-(Py-Y)-1H-benzimidazole-2-thiol or lower-alkyl ether or thioether thereof having the formula ##STR6## where Z is O or S, 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 1-oxide thereof, or 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-benzimidazol-2-ol according to claim 2.
Claim 5
Dependent Claim
6 words
5-(4-Pyridinyl)-1H-benzimidazol-2-ol N(py)oxide according to claim 1.
Claim 6
Dependent Claim
5 words
5-[(4-Pyridinyl)methyl]-1H-benzimidazol-2-ol according to claim 2.
Claim 7
Dependent Claim
5 words
5-(4-Pyridinyl)-1H-benzimidazole-2-thiol according to claim 2.
Claim 8
Dependent Claim
5 words
2-Ethoxy-5-(4-pyridinyl)-1H-benzimidazole according to claim 2.
Claim 9
Dependent Claim
5 words
2-(Ethylthio)-5-(4-pyridinyl)-1H-benzimidazole according to claim 2.
Claim 10
Dependent Claim
80 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 5-(Py-Y)-1H-benzimidazol-2-ol, 5-(Py-Y)-1H-benzimidazole-2-thiol or lower-alkyl ether or thioether thereof or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, 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 1-oxide thereof.
Claim 11
Dependent Claim
80 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 5-(Py-Y)-1H-benzimidazol-2-ol, 5-(Py-Y)-1H-benzimidazole-2-thiol or lower-alkyl ether or thioether thereof or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, 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 1-oxide thereof.
Claim 12
Dependent Claim
26 words
A composition 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 13
Independent Claim
79 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering to such patient a cardiotonically-effective amount of 5-(Py-Y)-1H-benzimidazol-2-ol, 5-(Py-Y)-1H-benzimidazole-2-thiol or lower-alkyl ether or thioether thereof or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, 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 1 oxide thereof.
Claim 14
Independent Claim
79 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering to such patient a cardiotonically-effective amount of 5-(Py-Y)-1H-benzimidazol-2-ol, 5-(Py-Y)-1H-benzimidazole-2-thiol or lower-alkyl ether or thioether thereof or pharmaceutically-acceptable acid-addition salt thereof, where Z is O or S, 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 1 oxide thereof.
Claim 15
Dependent Claim
26 words
The method 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.
References Cited (Backward Citations)
US3338916A
Cited
US3914310A
Cited
US3842098A
Cited
US3920683A
Cited
US3907822A
Cited
US4026936A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-06-14 | 1985-12-14 | 1986-06-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-06-14 | 1989-12-14 | 1990-06-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-06-14 | 1993-12-14 | 1994-06-15 | $7700.00 | Window Closed / Lapsed |