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US4485112A
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N-[(Benzofuran-2-yl)(phenyl)methyl]-alkylene diamines useful in treating arrhythmic, histaminic and tussive conditions
Assignee: A Menarini SAS
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Filing: 1983-02-22
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Granted: 1984-11-27
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Expires: 2003-02-22
Abstract
Abstract A 2-substituted benzofuran derivative of general formula I or II <IMAGE> (I) <IMAGE> (II) in which R1 and R2, can be the same or different, and are a hydrogen atom, a halogen atom, an alkyl group containing 1 to 4 carbon atoms, an arylalkyl group, an aryl group, a hydroxyl group, an alkoxy group, or an NH2, NH-alkyl, N(alkyl)2, NH(CO-alkyl), NH(CO-aryl) or NO2 group, or R1 and R2 can together form a ring of 5-8 carbon atoms; R3 is a hydrogen atom, an alkyl group containing 1 to 4 carbon atoms or an aryl group; R4 is a hydrogen atom, an alkyl group, an aryl or an arylalkyl group, R5 is a hydroxyl group, an alkoxy group, an OCO-aryl an OCO-alkyl, OCONH-alkyl or OCONH-aryl group, <IMAGE> <IMAGE> where n is a number between 1 and 4, R7 is a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, and R8 and R9, which can be the same or different, represent a hydrogen atom, an alkyl group, an aryl group, an alkoyl group, arylalkoyl group or an aroyl group, or can together form a heterocyclic ring which can contain supplementary heteratoms, and R6 is a hydrogen or halogen atom, an alkyl group, an arylalkyl group, an aryl group, a hydroxyl group, an alkoxy group, or an NH2, NH-alkyl, N(alkyl)2, NHCO-alkyl, NHCO-aryl or NO2 group. The compounds are useful for treating arrhythmic, histaminic and tussive conditions.
Inventors
- 👤 Vittorio Pestellini
- 👤 Mario Ghelardoni
- 👤 Carlo Alberto Maggi
- 👤 Gabrio Roncucci
- 👤 Alberto Meli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 15:21
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/92; A; A61; A61P; A61P21/00; A61P21/02; A61P25/00; A61P25/02; A61P3/00; A61P3/06; A61P43/00; A61P9/00; A61P9/06; C07D307/78; C07D307/79; C07D307/80; C07D307/81; C07D307/86
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
332 words
A compound selected from the group consisting of compounds having the formula ##STR28## and pharmaceutically acceptable salts thereof, in which: R 1 and R 2 are selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group containing 1 to 4 carbon atoms, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl group, a naphthyl group, a hydroxyl group, a lower alkoxy group, an NH 2 group, an NH-lower alkyl group, an N(lower alkyl) 2 group, an NH(CO-lower alkyl) group, an NH(CO-phenyl) group, an NH(CO-naphthyl) group, and an NO 2 group, and a ring of 5-8 carbon atoms including both R 1 and R 2 ; R 3 is selected from the group consisting of a hydrogen atom, an alkyl group containing 1 to 4 carbon atoms, a phenyl group and a naphthyl group; R 4 is selected from the group consisting of a hydrogen atom, a lower alkyl group, a phenyl group, a naphthyl group, a phenyl lower alkyl group and a naphthyl lower alkyl group; R 5 is an ##STR29## group in which n is an integer of from 1 to 4, R 7 is selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 4 carbon atoms, and R 8 and R 9 are selected from the group consisting of a hydrogen atom, a lower alkyl group, a phenyl group, a naphthyl group, a lower alkanoyl group, a phenyl lower alkanoyl group, a naphthyl lower alkanoyl group, a benzoyl group and a naphthoyl group; and R 6 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl group, a naphthyl group, a hydroxyl group, a lower alkoxy group, an NH 2 group, an NH-lower alkyl group, an N(lower alkyl) 2 group, an NHCO-lower alkyl group, an NHCO-phenyl group, and NHCO-naphthyl group and an NO 2 group.
Claim 2
Dependent Claim
332 words
A compound selected from the group consisting of compounds having the formula ##STR28## and pharmaceutically acceptable salts thereof, in which: R 1 and R 2 are selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group containing 1 to 4 carbon atoms, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl group, a naphthyl group, a hydroxyl group, a lower alkoxy group, an NH 2 group, an NH-lower alkyl group, an N(lower alkyl) 2 group, an NH(CO-lower alkyl) group, an NH(CO-phenyl) group, an NH(CO-naphthyl) group, and an NO 2 group, and a ring of 5-8 carbon atoms including both R 1 and R 2 ; R 3 is selected from the group consisting of a hydrogen atom, an alkyl group containing 1 to 4 carbon atoms, a phenyl group and a naphthyl group; R 4 is selected from the group consisting of a hydrogen atom, a lower alkyl group, a phenyl group, a naphthyl group, a phenyl lower alkyl group and a naphthyl lower alkyl group; R 5 is an ##STR29## group in which n is an integer of from 1 to 4, R 7 is selected from the group consisting of a hydrogen atom and an alkyl group containing from 1 to 4 carbon atoms, and R 8 and R 9 are selected from the group consisting of a hydrogen atom, a lower alkyl group, a phenyl group, a naphthyl group, a lower alkanoyl group, a phenyl lower alkanoyl group, a naphthyl lower alkanoyl group, a benzoyl group and a naphthoyl group; and R 6 is selected from the group consisting of a hydrogen atom, a halogen atom, a lower alkyl group, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl group, a naphthyl group, a hydroxyl group, a lower alkoxy group, an NH 2 group, an NH-lower alkyl group, an N(lower alkyl) 2 group, an NHCO-lower alkyl group, an NHCO-phenyl group, and NHCO-naphthyl group and an NO 2 group.
Claim 3
Dependent Claim
119 words
A compound according to claim 1, wherein R 1 and R 2 are each selected from the group consisting of hydrogen, halogen and lower alkoxy, and when R 1 and R 2 are taken together they form a ring of 5-8 carbon atoms, R 3 is selected from the group consisting of hydrogen and alkyl containing 1 to 4 carbon atoms, R 4 is selected from the group consisting of hydrogen, lower alkyl, phenyl lower alkyl, and naphthyl lower alkyl, R 8 and R 9 are each selected from the group consisting of hydrogen and lower alkyl, and R 6 is selected from the group consisting of hydrogen, halogen, lower alkyl, phenyl, naphthyl, lower alkoxy and NO 2 .
Claim 4
Dependent Claim
15 words
A compound according to claim 1, wherein R 1 and R 2 are the same.
Claim 5
Dependent Claim
14 words
A compound according to claim 1, wherein R 1 and R 2 are different.
Claim 6
Dependent Claim
15 words
A compound according to claim 1, wherein R 8 and R 9 are the same.
Claim 7
Dependent Claim
14 words
A compound according to claim 1, wherein R 8 and R 9 are different.
Claim 8
Dependent Claim
18 words
A compound according to claim 1, which contain one or more asymmetric carbon atoms, in optically active form.
Claim 9
Dependent Claim
90 words
A compound according to claim 1, selected from the group consisting of N,N-diethyl-N'-[(benzofuran-2-yl)(p-chlorophenyl) methyl]ethylenediamine and pharmaceutically acceptable salts thereof, N,N-diethyl-N'-[(benzofuran-2-yl)(phenyl) methyl]ethylenediamine and pharmaceutically acceptable salts thereof, N,N-dimethyl-N'-[(benzofuran-2-yl)(p-chlorophenyl)methyl]ethylenediamine and pharmaceutically acceptable salts thereof, N,N-dimethyl-N'-[(benzofuran-2-yl)(p-chlorophenyl) methyl]propylene-diamine and pharmaceutically acceptable salts thereof, N,N-dimethyl-N'[(benzofuran-2-yl)(phenyl) methyl]ethylenediamine and pharmaceutically acceptable salts thereof, N-[(benzofuran-2-yl)(p-chlorophenyl)methyl)]2-(diethylmethylammonium)ethylamine bromide and other pharmaceutically acceptable salts thereof, N-[(5-bromo-benzofuran-2-yl)(phenyl)methyl]-N', N'-diethylethylenediamine and pharmaceutically acceptable salts thereof, N-[(benzofuran-2-yl)(p-tolyl)methyl]-N',N'-diethylenediamine and pharmaceutically acceptable salts thereof, N,N-dimethyl-N'-[(benzofuran-2-yl)(p-fluorophenyl) methyl]ethylenediamine and pharmaceutically acceptable salts thereof, N,N-dimethyl-N'-[(5-bromobenzofuran-2-yl) (phenyl) methyl]ethylenediamine and pharmaceutically acceptable salts thereof, and N,N,N'-trimethyl-N'-[(benzofuran-2-yl) (p-chlorophenyl)methyl]ethylenediamine and pharmaceutically acceptable salts thereof.
Claim 10
Dependent Claim
62 words
A compound according to claim 1, wherein R 1 and R 2 are each selected from the group consisting of hydrogen and halogen, R 3 and R 4 are both hydrogen, R 8 and R 9 are selected from the group consisting of hydrogen and lower alkyl, and R 6 is selected from the group consisting of hydrogen, halogen and lower alkyl.
Claim 11
Dependent Claim
13 words
A compound according to claim 1, wherein the compound is N,N-diethyl-N'-[(benzofuran-2-yl)(p-chlorophenyl) methyl]ethylenediamine dihydrochloride.
Claim 12
Dependent Claim
38 words
A pharmaceutical composition comprising an anti-arrhythmic, or anti-histaminic, or anti-tussive, amount of at least one compound as claimed in claim 1 as active ingredient, in association with a member selected from the group consisting of carriers and excipients.
Claim 13
Dependent Claim
25 words
A composition according to claim 11, in suitable form for administration by a method selected from the group consisting of oral, parenteral and rectal administration.
Claim 14
Dependent Claim
13 words
A composition according to claim 12, in the form of a unit dose.
Claim 15
Dependent Claim
13 words
A composition according to claim 11, in the form of a unit dose.
Claim 16
Dependent Claim
32 words
A method of treating an arrhythmic, histaminic or tussive condition, which comprises administering to a mammal suffering from such a condition a correspondingly effective amount of a composition according to claim 11.
Claim 17
Dependent Claim
30 words
A method of treating a tussive condition, which comprises administering to a mammal suffering from such a condition a muscle relaxant effective amount of a composition according to claim 11.
References Cited (Backward Citations)
GB1160925A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-11-27 | 1988-05-28 | 1988-11-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-27 | 1992-05-28 | 1992-11-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-27 | 1996-05-28 | 1996-11-27 | $7700.00 | Window Closed / Lapsed |