Patent US4264136A successfully refreshed from Google Patents.
Patent US4139533A successfully refreshed from Google Patents.
US4139533A
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Bicyclo[2,2,1]heptane-2,3-diendo carboxylic acid imide esters of quinoline carboxylic acid
Assignee: Bristol Myers Co
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Filing: 1976-08-19
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Granted: 1979-02-13
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Expires: 1996-08-19
Abstract
Abstract A series of 5-endo-(quinoline-carbonyloxy)-,(benzothiophene-carbonyloxy)- and (quinoxaline-carbonyloxy)-N[amino-(lower)alkyl]bicyclo[2.2.1]-heptane-2,3-di-endo-carboxylic acid imides has been found to possess excellent prophylactic and therapeutic activity as anti-arrhythmic agents.
Inventors
- 👤 Ronald L. Buchanan
- 👤 John T. Woolever
- 👤 Alex M. Jelenevsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 17:05
CPC Classifications
C; C07; C07D; C07D409/00; C07D409/02; C07D409/12; C07D401/00; C07D401/02; C07D401/12; C07D403/00; C07D403/02; C07D403/12; C07D413/00; C07D413/14
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
102 words
A compound having the formula ##STR61## wherein R is a group of the formula ##STR62## in which R 1 and R 2 are alike or different and are each hydrogen, chloro, bromo, fluoro, (lower)alkyl, nitro, trifluoromethyl, hydroxy or (lower)alkoxy, R 3 is hydrogen, chloro, bromo, fluoro, (lower)alkyl, hydroxy 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 hydrogen, (lower)alkyl or, when taken together with the nitrogen, a heterocyclic ring of the formula ##STR63## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
102 words
A compound having the formula ##STR61## wherein R is a group of the formula ##STR62## in which R 1 and R 2 are alike or different and are each hydrogen, chloro, bromo, fluoro, (lower)alkyl, nitro, trifluoromethyl, hydroxy or (lower)alkoxy, R 3 is hydrogen, chloro, bromo, fluoro, (lower)alkyl, hydroxy 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 hydrogen, (lower)alkyl or, when taken together with the nitrogen, a heterocyclic ring of the formula ##STR63## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
11 words
The essentially pure dextrorotatory isomers of the compounds of claim 1.
Claim 4
Dependent Claim
11 words
The essentially pure levorotatory isomers of the compounds of claim 1.
Claim 5
Dependent Claim
103 words
A compound having the formula ##STR64## wherein R is a group of the formula ##STR65## in which R 1 is hydrogen, chloro, bromo, fluoro, (lower)alkyl, nitro, trifluoromethyl, hydroxy or (lower)alkoxy with the proviso that the quinoline ring may not be substituted at positions 2, 3 or 4 by nitro or trifluoromethyl, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and are each hydrogen, (lower)alkyl or, when taken together with the nitrogen, a heterocyclic ring of the formula ##STR66## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
103 words
A compound having the formula ##STR64## wherein R is a group of the formula ##STR65## in which R 1 is hydrogen, chloro, bromo, fluoro, (lower)alkyl, nitro, trifluoromethyl, hydroxy or (lower)alkoxy with the proviso that the quinoline ring may not be substituted at positions 2, 3 or 4 by nitro or trifluoromethyl, n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and are each hydrogen, (lower)alkyl or, when taken together with the nitrogen, a heterocyclic ring of the formula ##STR66## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
11 words
The essentially pure levorotatory isomers of the compounds of claim 4.
Claim 8
Dependent Claim
11 words
The essentially pure dextrorotatory isomers of the compounds of claim 4.
Claim 9
Dependent Claim
29 words
A compound of claim 4 wherein R 4 and R 5 are alike or different and each is hydrogen or (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
26 words
A compound of claim 4 wherein n is 3 and R 4 and R 5 are each methyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
67 words
A compound having the formula ##STR67## wherein R is a group of the formula ##STR68## n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and are each hydrogen, (lower)alkyl or, when taken together with the nitrogen, a heterocyclic ring of the formula ##STR69## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
67 words
A compound having the formula ##STR67## wherein R is a group of the formula ##STR68## n is an integer of 2 to 4 inclusive and R 4 and R 5 are alike or different and are each hydrogen, (lower)alkyl or, when taken together with the nitrogen, a heterocyclic ring of the formula ##STR69## in which R 6 is (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Dependent Claim
11 words
The essentially pure levorotatory isomers of the compounds of claim 9.
Claim 14
Dependent Claim
11 words
The essentially pure dextrorotatory isomers of the compounds of claim 9.
Claim 15
Dependent Claim
17 words
A compound of claim 9 wherein R is ##STR70## or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
17 words
A compound of claim 9 wherein R is ##STR71## or a pharmaceutically acceptable acid addition salt thereof.
Claim 17
Dependent Claim
17 words
A compound of claim 9 wherein R is ##STR72## or a pharmaceutically acceptable acid addition salt thereof.
Claim 18
Dependent Claim
17 words
A compound of claim 9 wherein R is ##STR73## or a pharmaceutically acceptable acid addition salt thereof.
Claim 19
Dependent Claim
29 words
A compound of claim 9 wherein R 4 and R 5 are alike or different and each is hydrogen or (lower)alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 20
Dependent Claim
26 words
A compound of claim 9 wherein n is 3 and R 4 and R 5 are each methyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 21
Dependent Claim
11 words
The compound having the formula ##STR74## or the hydrochloride salt thereof.
Claim 22
Dependent Claim
11 words
The compound having the formula ##STR74## or the hydrochloride salt thereof.
Claim 23
Dependent Claim
13 words
The essentially pure levorotatory isomer of the compound or salt of claim 18.
Claim 24
Dependent Claim
13 words
The essentially pure dextrorotatory isomer of the compound or salt of claim 18.
Claim 25
Dependent Claim
11 words
The compound having the formula ##STR75## or the hydrochloride salt thereof.
Claim 26
Dependent Claim
11 words
The compound having the formula ##STR75## or the hydrochloride salt thereof.
Claim 27
Dependent Claim
13 words
The essentially pure levorotatory isomer of the compound or salt of claim 21.
Claim 28
Dependent Claim
13 words
The essentially pure dextrorotatory isomer of the compound or salt of claim 21.
Claim 29
Dependent Claim
11 words
The compound having the formula ##STR76## or the hydrochloride salt thereof.
Claim 30
Dependent Claim
11 words
The compound having the formula ##STR76## or the hydrochloride salt thereof.
Claim 31
Dependent Claim
13 words
The essentially pure levorotatory isomer of the compound or salt of claim 24.
Claim 32
Dependent Claim
13 words
The essentially pure dextrorotatory isomer of the compound or salt of claim 24.
Claim 33
Dependent Claim
11 words
The compound having the formula ##STR77## or the hydrochloride salt thereof.
Claim 34
Dependent Claim
11 words
The compound having the formula ##STR77## or the hydrochloride salt thereof.
Claim 35
Dependent Claim
13 words
The essentially pure levorotatory isomer of the compound or salt of claim 27.
Claim 36
Dependent Claim
13 words
The essentially pure dextrorotatory isomer of the compound or salt of claim 27.
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) | 1982-02-12 | 1982-08-14 | 1983-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-12 | 1986-08-14 | 1987-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-12 | 1990-08-14 | 1991-02-13 | $7700.00 | Window Closed / Lapsed |