US4289787A
Expired / Lapsed
US
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Quaternary ammonium antiarrhythmic drugs
Assignee: Eli Lilly and Co
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Filing: 1979-12-10
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Granted: 1981-09-15
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Expires: 1999-12-10
Abstract
Abstract Quaternary ammonium salts of certain phenylbutylamines are useful antiarrhythmic drugs. A method for treating arrhythmia and prolonging the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such quaternary ammonium salts are disclosed.
Inventors
- 👤 Bryan B. Molloy
- 👤 Mitchell I. Steinberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 16:50
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/13; A61K31/135
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
84 words
A compound having the general formula ##STR3## wherein: R 1 is hydrogen or C 1 -C 2 alkyl; R 2 is hydrogen or C 1 -C 3 alkyl; R 3 is C 1 -C 4 alkyl or phenyl C 1 -C 4 alkyl; R 4 is C 1 -C 8 alkyl; R 5 is C 6 -C 10 alkyl; R 6 is hydrogen, hydroxy, halogen, nitro, C 1 -C 3 alkoxy, or C 1 -C 3 alkyl; and X is a therapeutically acceptable anion.
Claim 2
Dependent Claim
84 words
A compound having the general formula ##STR3## wherein: R 1 is hydrogen or C 1 -C 2 alkyl; R 2 is hydrogen or C 1 -C 3 alkyl; R 3 is C 1 -C 4 alkyl or phenyl C 1 -C 4 alkyl; R 4 is C 1 -C 8 alkyl; R 5 is C 6 -C 10 alkyl; R 6 is hydrogen, hydroxy, halogen, nitro, C 1 -C 3 alkoxy, or C 1 -C 3 alkyl; and X is a therapeutically acceptable anion.
Claim 3
Dependent Claim
31 words
The compound of claim 1 wherein R 3 is C 1 -C 4 alkyl and R 6 is halogen, nitro, C 1 -C 3 alkoxy, or C 1 -C 3 alkyl.
Claim 4
Dependent Claim
11 words
The compound according to claim 1, said compound being N,N-diethyl-N-n-heptyl-4-phenylbutylammonium bromide.
Claim 5
Dependent Claim
11 words
The compound according to claim 1, said compound being N,N-dimethyl-N-n-octyl-4-phenylbutylammonium bromide.
Claim 6
Dependent Claim
11 words
The compound according to claim 1, said compound being N,N-dimethyl-N-n-hexyl-4-phenylbutylammonium bromide.
Claim 7
Dependent Claim
11 words
The compound according to claim 1, said compound being N,N-dimethyl-N-n-heptyl-1-methyl-4-phenylbutylammonium bromide.
Claim 8
Dependent Claim
11 words
The compound according to claim 1, said compound being N,N-dimethyl-N-sec-octyl-4-phenylbutylammonium bromide.
Claim 9
Dependent Claim
12 words
The compound of claim 1 wherein R 6 is halogen or nitro.
Claim 10
Dependent Claim
11 words
The compound according to claim 8, said compound being N,N-diethyl-N-n-heptyl-4-(4-chlorophenyl)butylammonium bromide.
Claim 11
Dependent Claim
11 words
The compound according to claim 8, said compound being N,N-diethyl-N-n-heptyl-4-(4-(4-nitrophenyl)butylammonium bromide.
Claim 12
Dependent Claim
11 words
The compound according to claim 8, said compound being N,N-diethyl-N-n-heptyl-4-(4-chlorophenyl)butylammonium phosphate.
Claim 13
Dependent Claim
18 words
The compound of claim 1 wherein R 3 and R 4 both are C 1 -C 2 alkyl.
Claim 14
Dependent Claim
21 words
The compound of claim 1 wherein R 3 and R 4 both are methyl and R 5 is n-hexyl or n-heptyl.
Claim 15
Dependent Claim
21 words
The compound of claim 1 wherein R 3 and R 4 both are ethyl and R 5 is n-hexyl or n-heptyl.
Claim 16
Dependent Claim
23 words
The compound of claim 1 wherein R 3 is C 1 -C 2 alkyl and R 4 is C 4 -C 5 alkyl.
Claim 17
Dependent Claim
19 words
The compound of claim 1 wherein R 1 is C 1 -C 2 alkyl and R 2 is hydrogen.
Claim 18
Dependent Claim
40 words
The compound of claim 1 wherein R 1 is methyl, R 2 is hydrogen, R 3 and R 4 are C 1 -C 2 alkyl, R 5 is C 6 -C 7 alkyl and R 6 is other than hydrogen.
Claim 19
Dependent Claim
36 words
The compound of claim 1 wherein R 1 and R 2 are hydrogen, R 3 and R 4 independently are C 1 -C 2 alkyl, R 6 is halogen or nitro, and X - is phosphate.
Claim 20
Dependent Claim
24 words
A method of treating re-entrant arrhythmias comprising administering to a subject in need thereof an antiarrhythmically effective dose of a compound of claim 1.
Claim 21
Dependent Claim
36 words
The method according to claim 19 employing the compound wherein R 3 is C 1 -C 4 alkyl and R 6 is hydrogen, halogen, nitro, C 1 -C 3 alkoxy, or C 1 -C 3 alkyl.
Claim 22
Dependent Claim
43 words
The method according to claim 19 employing the compound wherein R 1 is hydrogen or methyl, R 2 is hydrogen, R 3 is C 1 -C 2 alkyl, R 4 is C 1 -C 2 alkyl, and R 6 is other than hydrogen.
Claim 23
Dependent Claim
13 words
The method according to claim 19 wherein the compound administered is N,N-diethyl-N-n-heptyl-4-(4-chlorophenyl)butylammonium bromide.
Claim 24
Dependent Claim
13 words
The method according to claim 19 wherein the compound administered is N,N-diethyl-N-n-heptyl-4-(4-chlorophenyl)butylammonium phosphate.
Claim 25
Dependent Claim
40 words
A pharmaceutical formulation useful in the treatment of re-entrant arrhythmias in humans comprising as active ingredient an antiarrhythmic amount of a quaternary ammonium salt defined in claim 1 in combination with one or more pharmaceutically acceptable diluents or carriers thereof.
Claim 26
Dependent Claim
36 words
The formulation of claim 24 employing the active ingredient wherein R 3 is C 1 -C 4 alkyl, and R 6 is hydrogen, halogen, nitro, C 1 -C 3 alkoxy or C 1 -C 3 alkyl.
Claim 27
Dependent Claim
62 words
The formulation according to claim 25 employing the active ingredient of the formula R 1 is hydrogen or methyl; R 2 is hydrogen; R 3 is C 1 -C 2 alkyl; R 4 is C 1 -C 2 alkyl; R 6 is hydrogen, C 1 -C 3 alkoxy, C 1 -C 3 alkyl or nitro, and X is a therapeutically acceptable anion.
Claim 28
Dependent Claim
13 words
The formulation according to claim 25 wherein the active ingredient is N,N-diethyl-N-n-heptyl-4-(4-chlorophenyl)butylammonium bromide.
Claim 29
Dependent Claim
13 words
The formulation according to claim 25 wherein the active ingredient is N,N-diethyl-N-n-heptyl-4-(4-chlorophenyl)butylammonium phosphate.
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) | 1984-09-14 | 1985-03-16 | 1985-09-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-14 | 1989-03-16 | 1989-09-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-14 | 1993-03-16 | 1993-09-15 | $7700.00 | Window Closed / Lapsed |