US3980668A
Expired / Lapsed
US
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Anti-arrhythimic 5-endo-(3-indolecarbonyloxy)-N-[amino-(lower)alkyl]bicyclo[2,2,1]heptane-2,3-di-endo-carboxylic acid imides
Assignee: Bristol Myers Co
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Filing: 1975-07-10
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Granted: 1976-09-14
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Expires: 1995-07-10
Abstract
Abstract A series of 5-endo-(3-indolecarbonyloxy)-N-[amino-(lower)alkyl]bicyclo[2.2.1]hepta ne-2,3-di-endo-carboxylic acid imides having the formula WHEREIN R1 is H, Cl, Br, F or (lower)alkyl, R7 is H or methyl, R2 and R3 are alike or different and each is H, Cl, Br, F, (lower)alkyl, nitro, CF3, OH or (lower)alkoxy, n is an integer of 2 to 4 inclusive and R4 and R5 are alike or different and each is H, (lower)alkyl or when taken together with the nitrogen a radical of the formula IN WHICH R6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof have been found to possess unique prophylactic and therapeutic activity as anti-arrhythmia agents. An example of such a compound possessing excellent activity is 5-endo-(3-indolecarbonyloxy)-N-(3-dimethylaminopropyl)bicyclo-[2.2.1]h eptane-2,3-di-endo-carboxylic acid imide hydrochloride.
Inventors
- 👤 Ronald Leslie Buchanan
- 👤 Alex Michael Jelenevsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 00:28
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/02; C07D403/12; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/40; A61P; A61P9/00; A61P9/06
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
97 words
A compound having the formula ##SPC56## wherein R 1 is H, Cl, Br, F or (lower)alkyl, R 7 is H or methyl, R 2 and R 3 are alike or different and each is H, Cl, Br, F, (lower)alkyl, nitro, CF 3 , OH or (lower)alkoxy, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and each is H, (lower)alkyl or when taken together with the nitrogen a radical of the formula ##SPC57## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
97 words
A compound having the formula ##SPC56## wherein R 1 is H, Cl, Br, F or (lower)alkyl, R 7 is H or methyl, R 2 and R 3 are alike or different and each is H, Cl, Br, F, (lower)alkyl, nitro, CF 3 , OH or (lower)alkoxy, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and each is H, (lower)alkyl or when taken together with the nitrogen a radical of the formula ##SPC57## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
97 words
A compound having the formula ##SPC58## wherein R 1 is H, Cl, Br, F or (lower)alkyl, R 7 is H or methyl, R 2 and R 3 are alike or different and each is H, Cl, Br, F, (lower)alkyl, nitro, CF 3 , OH or (lower)alkoxy, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and each is H, (lower)alkyl or when taken together with the nitrogen a radical of the formula ##SPC59## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
97 words
A compound having the formula ##SPC58## wherein R 1 is H, Cl, Br, F or (lower)alkyl, R 7 is H or methyl, R 2 and R 3 are alike or different and each is H, Cl, Br, F, (lower)alkyl, nitro, CF 3 , OH or (lower)alkoxy, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and each is H, (lower)alkyl or when taken together with the nitrogen a radical of the formula ##SPC59## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
89 words
A compound of claim 2 having the formula ##SPC60## wherein R 1 is Cl, Br, F, H or (lower)alkyl, R 7 is H or methyl, R 2 is H, Cl, Br, F, CF 3 , (lower)alkyl, OH or (lower)alkoxy, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and each is H, (lower)alkyl or when taken together with the nitrogen radical of the formula ##SPC61## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
88 words
A compound of claim 2 having the formula ##SPC62## wherein R 1 and R 2 are alike or different and each is H, Cl, Br, F, or (lower)alkyl, and R 2 can also be CF 3 , n is an integer of 2 to 4 inclusive and R 4 and R 5 are like or diferent and each is H, (lower)alkyl or when taken together with the nitrogen a radical of the formula ##SPC63## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
71 words
A compound of claim 2 having the formula ##SPC64## wherein R 1 is H, F, Cl, methoxy, ethoxy or n-propoxy, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and each is H, (lower)-alkyl or when taken together with the nitrogen a radical of the formula ##SPC65## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
53 words
A compound of claim 2 having the formula ##SPC66## wherein R 1 is H, F, Cl, methoxy, ethoxy or n-propoxy, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and each is H or (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
42 words
A compound of claim 2 having the formula ##SPC67## in which R 1 is H, Cl, methoxy or ethoxy, and R 4 and R 5 are alike or different and are H or (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
33 words
A compound having the formula ##SPC68## in which R 4 and R 5 are alike or different and each is H, methyl, ethyl or isopropyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
33 words
A compound having the formula ##SPC68## in which R 4 and R 5 are alike or different and each is H, methyl, ethyl or isopropyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
11 words
The compound having the formula ##SPC69## or the hydrochloride salt thereof.
Claim 13
Dependent Claim
11 words
The compound having the formula ##SPC69## or the hydrochloride salt thereof.
Claim 14
Dependent Claim
11 words
The compound having the formula ##SPC70## or the hydrochloride salt thereof.
Claim 15
Dependent Claim
11 words
The compound having the formula ##SPC70## or the hydrochloride salt thereof.
Claim 16
Dependent Claim
11 words
The essentially pure levorotatory isomer of the compound of claim 9.
Claim 17
Dependent Claim
11 words
The essentially pure dextrorotatory isomer of the compound of claim 9.
Claim 18
Dependent Claim
11 words
The essentially pure dextrorotatory isomers of the compounds of claim 1.
Claim 19
Dependent Claim
11 words
The essentially pure levorotatory isomers of the compounds of claim 1.
Claim 20
Dependent Claim
11 words
The essentially pure levorotatory isomers of the compounds of claim 2.
Claim 21
Dependent Claim
11 words
The essentially pure dextrorotatory isomers of the compounds of claim 2.
Claim 22
Dependent Claim
11 words
The essentially pure levorotatory isomers of the compounds of claim 6.
Claim 23
Dependent Claim
11 words
The essentially pure dextrorotatory isomers of the compounds of claim 6.
References Cited (Backward Citations)
US3850922A
Cited
US3850921A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-14 | 1980-03-15 | 1980-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-14 | 1984-03-15 | 1984-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-14 | 1988-03-15 | 1988-09-14 | $7700.00 | Window Closed / Lapsed |