US4411908A
Expired / Lapsed
US
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Imidazoline derivatives as presynaptic α2 -adrenoreceptor antagonists
Assignee: Pierre Fabre Medicament SA
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Filing: 1982-07-13
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Granted: 1983-10-25
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Expires: 2002-07-13
Abstract
Abstract Imidazoline derivatives of the formula ##STR1## wherein R 1 is hydrogen or alkyl C 1-6 ; R 2 is hydrogen, methyl, chloro, bromo or fluoro; R 3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; and their non-toxic salts. Processes for their preparation and pharmaceutical compositions thereof. The compounds exhibit presynaptic α 2 -adrenoreceptor antagonist activity.
Inventors
- 👤 Christopher B. Chapleo
- 👤 Peter L. Myers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 16:36
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; A; A61; A61P; A61P25/00; A61P25/02; A61P25/04; A61P25/06; A61P25/24; A61P25/26; A61P9/00; A61P9/06; C07D303/00; C07D303/02; C07D303/12; C07D303/14; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C07D307/80; C07D307/82; C07D307/84; C07D307/85
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
41 words
A compound of the formula ##STR13## wherein R 1 is hydrogen or alkyl C 1-6 ; R 2 is hydrogen, methyl, chloro, bromo or fluoro; R 3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; or a non-toxic salt thereof.
Claim 2
Dependent Claim
41 words
A compound of the formula ##STR13## wherein R 1 is hydrogen or alkyl C 1-6 ; R 2 is hydrogen, methyl, chloro, bromo or fluoro; R 3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; or a non-toxic salt thereof.
Claim 3
Dependent Claim
55 words
A compound of formula I given in claim 1 wherein R 1 is hydrogen or alkyl C 1-6 ; R 2 is hydrogen and R 3 is methyl, hydroxy, methoxy, fluoro, chloro or bromo; or R 2 and R 3 are the same and both are hydrogen, methyl or chloro; or a non-toxic salt thereof.
Claim 4
Dependent Claim
6 words
2-[2-(2-Methyl-2,3-dihydrobenzofuranyl)]-2-imidazoline or a non-toxic salt thereof.
Claim 5
Dependent Claim
6 words
2-[2-(2-Methyl-2,3-dihydrobenzofuranyl)]-2-imidazoline or a non-toxic salt thereof.
Claim 6
Dependent Claim
6 words
2-[2-(5-Chloro-2,3-dihydrobenzofuranyl)]-2-imidazoline or a non-toxic salt thereof.
Claim 7
Dependent Claim
6 words
2-[2-(5-Chloro-2,3-dihydrobenzofuranyl)]-2-imidazoline or a non-toxic salt thereof.
Claim 8
Dependent Claim
6 words
2-[2-(2,3-Dihydrobenzofuranyl)]-2-imidazoline or a non-toxic salt thereof.
Claim 9
Dependent Claim
6 words
2-[2-(2,3-Dihydrobenzofuranyl)]-2-imidazoline or a non-toxic salt thereof.
Claim 10
Dependent Claim
40 words
A compound according to claim 1 which is selected from the group consisting of 2-[2-(4-chloro-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(7-methyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5-chloro-7-methyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5-fluoro-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5-methoxy-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5-hydroxy-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(4-methyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5-methyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5-bromo-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(6-methyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(6-methoxy-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(7-methoxy-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(7-chloro-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(4,7-dimethyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5,6-dimethyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5,7-dimethyl-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(5,7-dichloro-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(6,7-dichloro-2,3-dihydrobenzofuranyl)]-2-imidazoline, 2-[2-(6-hydroxy-2,3-dihydrobenzofuranyl)]-2-imidazoline and 2-[2-(7-hydroxy-2,3-dihydrobenzofuranyl)]-2-imidazoline or a non-toxic salt thereof.
Claim 11
Dependent Claim
38 words
A pharmaceutical composition for presynaptic α 2 -adrenoreceptor antagonist use comprising a compound as claimed in claim 1, or a non-toxic salt thereof in an amount effective for said use together with a pharmaceutically acceptable diluent or carrier.
Claim 12
Dependent Claim
14 words
A pharmaceutical composition as claimed in claim 7 which is in unit dosage form.
Claim 13
Dependent Claim
32 words
A pharmaceutical composition as claimed in claim 8 for oral administration wherein each unit dosage contains from 1 to 200 mg of the compound of formula I or a non-toxic salt thereof.
Claim 14
Dependent Claim
29 words
A pharmaceutical composition as claimed in claim 9 wherein each unit dosage contains from 10 to 50 mg of the compound of formula I or a non-toxic salt thereof.
Claim 15
Dependent Claim
38 words
A pharmaceutical composition as claimed in claim 8 for parenteral administration wherein each unit dosage contains from 0.1 to 10 mg of the compound of formula I or a non-toxic salt thereof per 1 ml of the composition.
Claim 16
Dependent Claim
28 words
A method of treating depression which comprises administering to a human an antidepressant effective amount of a compound as claimed in claim 1 or a non-toxic salt thereof.
Claim 17
Dependent Claim
28 words
A method of treating migraine which comprises administering to a human an antimigraine effective amount of a compound as claimed in claim 1 or a non-toxic salt thereof.
References Cited (Backward Citations)
US3927023A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-24 | 1987-04-25 | 1987-10-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-24 | 1991-04-25 | 1991-10-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-24 | 1995-04-25 | 1995-10-25 | $7700.00 | Window Closed / Lapsed |