US4239684A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,5'-Benzodiazepine-2-ones, pharmaceutical compositions thereof and method of use thereof
Assignee: Abbott GmbH and Co KG
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Filing: 1978-06-02
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Granted: 1980-12-16
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Expires: 1998-06-02
Abstract
Abstract 1-Aryl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-ones of the general formula ##STR1## wherein: R 1 is hydrogen, lower alkyl, preferably of 1-3 carbons, or unsaturated lower alkyl preferably of 2-3 carbons R 2 , R 3 , R 4 , R 5 are the same or different and are each hydrogen, halogen, lower alkyl, preferably methyl, lower alkoxy, preferably methoxy, or trifluoromethyl, and R 6 , R 7 , R 8 , R 9 are the same or different and are each hydrogen or lower alkyl, preferably methyl. The compounds are prepared by dehydrohalogenating substituted 2-(3'-halogenopropionylamino)-diphenyl amines of the general formula ##STR2## wherein R 2 to R 9 are the same as defined above and X is halogen, in the presence of a solvent and a base, to cyclize the amines and then alkylating to introduce the unsaturated lower alkyl radical R 1 on the nitrogen in the 5 position, if necessary. The compounds possess anticonvulsant, sedative and muscle relaxant properties.
Inventors
- 👤 Oskar Bub
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:38
CPC Classifications
C; C07; C07D; C07D243/00; C07D243/06; C07D243/10; C07D243/12
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
98 words
A 1-aryl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one of the formula ##STR5## wherein R 1 is hydrogen, lower alkyl, or unsaturated lower aliphatic hydrocarbon; R 4 and R 5 are the same or different and each is hydrogen, halogen, lower alkyl, lower alkoxy, or trifluoromethyl, but if one of R 4 and R 5 is halogen or trifluoromethyl and the other of R 4 and R 5 is hydrogen, then the halogen or trifluoromethyl substituent is in the para-position; and R 6 , R 7 , R 8 , and R 9 are the same or different and each is hydrogen or lower alkyl.
Claim 2
Dependent Claim
98 words
A 1-aryl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one of the formula ##STR5## wherein R 1 is hydrogen, lower alkyl, or unsaturated lower aliphatic hydrocarbon; R 4 and R 5 are the same or different and each is hydrogen, halogen, lower alkyl, lower alkoxy, or trifluoromethyl, but if one of R 4 and R 5 is halogen or trifluoromethyl and the other of R 4 and R 5 is hydrogen, then the halogen or trifluoromethyl substituent is in the para-position; and R 6 , R 7 , R 8 , and R 9 are the same or different and each is hydrogen or lower alkyl.
Claim 3
Dependent Claim
53 words
A compound as in claim 1 wherein R 1 is hydrogen, lower alkyl having 1 to 3 carbon atoms, or unsaturated aliphatic hydrocarbon having 2 to 3 carbon atoms and R 6 , R 7 , R 8 , and R 9 are the same or different and each is hydrogen or methyl.
Claim 4
Dependent Claim
67 words
A compound as in claim 1 wherein R 1 is hydrogen, methyl, ethyl, or allyl; R 4 is hydrogen, fluoro, chloro, bromo, methyl, methoxy, or trifluoromethyl; R 5 is hydrogen or chloro; and R 6 , R 7 , R 8 , and R 9 are the same or different and each is hydrogen or methyl but at least two of R 6 -R 9 are hydrogen.
Claim 5
Dependent Claim
15 words
A compound as in claim 2 wherein R 4 and R 5 are both hydrogen.
Claim 6
Dependent Claim
16 words
A compound as in claim 2 wherein R 4 is hydrogen and R 5 is chlorine.
Claim 7
Dependent Claim
15 words
A compound as in claim 2 wherein R 4 and R 5 are both methyl.
Claim 8
Dependent Claim
16 words
A compound as in claim 2 wherein R 4 is hydrogen and R 5 is methoxy.
Claim 9
Dependent Claim
11 words
A compound as in claim 1 which has the formula ##STR6##
Claim 10
Dependent Claim
9 words
A compound as in claim 1 which is 8-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one.
Claim 11
Dependent Claim
9 words
A compound as in claim 1 which is 8-chloro-5-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one.
Claim 12
Dependent Claim
9 words
A compound as in claim 1 which is 8-chloro-4-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one.
Claim 13
Dependent Claim
9 words
A compound as in claim 1 which is 8-chloro-4,5-dimethyl-1-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one.
Claim 14
Dependent Claim
9 words
A compound as in claim 1 which is 8-chloro-1-(4'-methoxyphenyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one.
Claim 15
Dependent Claim
24 words
A sedative composition comprising an effective sedative amount of a compound as in claim 1 and an inert pharmaceutical carrier, in dosage unit form.
Claim 16
Dependent Claim
24 words
A sedative composition comprising an effective sedative amount of a compound as in claim 2 and an inert pharmaceutical carrier, in dosage unit form.
Claim 17
Dependent Claim
28 words
The method of producing a sedative sedative effect in a patient which comprises orally administering to said patient an effective amount of a compound as in claim 1.
Claim 18
Dependent Claim
28 words
The method of producing a sedative sedative effective in a patient which comprises orally administering to said patient an effective amount of a compound as in claim 2.
References Cited (Backward Citations)
US3321468A
Cited
US3816409A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-12-16 | 1984-06-16 | 1984-12-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-16 | 1988-06-16 | 1988-12-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-16 | 1992-06-16 | 1992-12-16 | $7700.00 | Window Closed / Lapsed |