US4264612A
Expired / Lapsed
US
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Lower-alkyl 2-halo-5-(pyridinyl)nicotinates, their preparation and use as cardiotonics
Assignee: Sanofi SA
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Filing: 1980-03-17
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Granted: 1981-04-28
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Expires: 2000-03-17
Abstract
Abstract Cardiotonic composition and method for increasing cardiac contractility using an effective amount of a cardiotonic lower-alkyl 2-halo-5-PY-6-Q'-nicotinate or pharmaceutically-acceptable acid-addition salt thereof, where halo is chloro or bromo, Q' is hydrogen or lower-alkyl and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents. Also shown are novel lower-alkyl 2-halo-5-PY-6-(lower-alkyl)nicotinates or pharmaceutically-acceptable acid-addition salt thereof, useful as intermediates or cardiotonics and preparation thereof.
Inventors
- 👤 George Y. Lesher
- 👤 Monte D. Gruett
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:59
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/53; C07D213/46; C07D213/50; C07D213/60; C07D213/78; C07D213/79; C07D213/80; C07D213/84; C07D213/85; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
75 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, an effective amount for increasing cardiac contractility of the cardiotonic lower-alkyl 2-halo-5-PY-6-Q'-nicotinate or pharmaceutically-acceptable acid-addition salt thereof where halo is chloro or bromo, Q' is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 2
Dependent Claim
75 words
A cardiotonic composition for increasing cardiac contractility, said composition comprising a pharmaceutically-acceptable inert carrier and, as the active component thereof, an effective amount for increasing cardiac contractility of the cardiotonic lower-alkyl 2-halo-5-PY-6-Q'-nicotinate or pharmaceutically-acceptable acid-addition salt thereof where halo is chloro or bromo, Q' is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 3
Dependent Claim
11 words
The composition of claim 1 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 4
Dependent Claim
9 words
The composition of claim 1 where halo is chloro.
Claim 5
Dependent Claim
11 words
The composition of claim 1 where Q' is methyl or ethyl.
Claim 6
Dependent Claim
9 words
The composition of claim 1 wherein Q' is hydrogen.
Claim 7
Independent Claim
82 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering orally or parenterally in a solid or liquid dosage form to such patient an effective amount for increasing cardiac contractility of the cardiotonic 2-halo-5-PY-6-Q'-nicotinate or pharmaceutically-acceptable acid-addition salt thereof where halo is chloro or bromo, Q' is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 8
Independent Claim
82 words
The method for increasing cardiac contractility in a patient requiring such treatment which comprises administering orally or parenterally in a solid or liquid dosage form to such patient an effective amount for increasing cardiac contractility of the cardiotonic 2-halo-5-PY-6-Q'-nicotinate or pharmaceutically-acceptable acid-addition salt thereof where halo is chloro or bromo, Q' is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 9
Dependent Claim
11 words
The method of claim 6 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 10
Dependent Claim
9 words
The method of claim 6 where halo is chloro.
Claim 11
Dependent Claim
11 words
The method of claim 6 where Q' is methyl or ethyl.
Claim 12
Dependent Claim
9 words
The method of claim 6 where Q' is hydrogen.
Claim 13
Dependent Claim
50 words
Lower-alkyl 2-halo-5-PY-6-(lower-alkyl)nicotinate having the formula ##STR3## where Q and R' are each lower-alkyl, X is chloro or bromo, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition salt thereof, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 14
Dependent Claim
50 words
Lower-alkyl 2-halo-5-PY-6-(lower-alkyl)nicotinate having the formula ##STR3## where Q and R' are each lower-alkyl, X is chloro or bromo, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically-acceptable acid-addition salt thereof, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 15
Dependent Claim
11 words
The compound of claim 11 where PY is 4-pyridinyl or 3-pyridinyl.
Claim 16
Dependent Claim
9 words
The compound of claim 11 where X is chloro.
Claim 17
Dependent Claim
11 words
The compound of claim 11 where Q is methyl or ethyl.
Claim 18
Dependent Claim
87 words
The process which comprises the steps of heating 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-PY-nicotinonitrile with an aqueous mineral acid to produce 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-PY-nicotinic acid, reacting said acid with an inorganic halogenating agent selected from POCl 3 , PCl 3 , PBr 3 or PCl 5 to produce 2-halo-6-(lower-alkyl)-5-PY-nicotinoyl halide and heating the halide with a lower-alkanol to produce lower-alkyl 2-halo-6-(lower-alkyl)-5-PY-nicotinate, where halo is chloro or bromo, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 19
Dependent Claim
87 words
The process which comprises the steps of heating 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-PY-nicotinonitrile with an aqueous mineral acid to produce 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-PY-nicotinic acid, reacting said acid with an inorganic halogenating agent selected from POCl 3 , PCl 3 , PBr 3 or PCl 5 to produce 2-halo-6-(lower-alkyl)-5-PY-nicotinoyl halide and heating the halide with a lower-alkanol to produce lower-alkyl 2-halo-6-(lower-alkyl)-5-PY-nicotinate, where halo is chloro or bromo, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, and where lower-alkyl, all occurrences, contains from one to six carbon atoms.
Claim 20
Dependent Claim
28 words
The process according to claim 15 where halo is chloro, the lower-alkyl portion of the resulting ester is methyl or ethyl and the 6-substituent is methyl or ethyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-27 | 1984-10-27 | 1985-04-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-27 | 1988-10-27 | 1989-04-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-27 | 1992-10-27 | 1993-04-28 | $7700.00 | Window Closed / Lapsed |