US4064139A
Expired / Lapsed
US
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Substituted 9,10-dihydroanthracen-9,10-imines
Assignee: Merck and Co Inc
•
Filing: 1976-10-28
•
Granted: 1977-12-20
•
Expires: 1996-10-28
Abstract
Abstract Substituted 9,10-dihydroanthracen-9,10-imines are disclosed to be minor tranquilizers, anticonvulsnts, muscle relaxants, and to be useful in the treatment of extrapyramidal disorders such as Parkinson's disease; also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions.
Inventors
- 👤 Paul S. Anderson
- 👤 Marcia E. Christy
- 👤 Gerald S. Ponticello
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 07:58
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/12; C07D471/18; C07D487/00; C07D487/02; C07D487/08
Claims Analysis
Total Claims: 58
Claim 1
Independent Claim
26 words
A compound selected from the group consisting of: 2-bromo-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-methoxy-11-methyl-9,10-dihydroanthracen-9,10-imine; 9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-iodo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-iodo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine 2-iodo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 9,10-dihydro-2,11-dimethyl-9,10-diethylanthracen-9,10-imine; 2-chloro-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine; 9,10-dihydro-1-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine; 9,10-dihydro-2-methoxy-9,10-diethyl-11-methylanthracen-9,10-imine; 9,10-dihydro-9,10-diethyl-1,11-dimethylanthracen-9,10-imine; 9,10-dihydro-2-trifluoromethyl-9,10-diethyl-11-methylanthracen-9,10-imine;
Claim 2
Dependent Claim
26 words
A compound selected from the group consisting of: 2-bromo-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-methoxy-11-methyl-9,10-dihydroanthracen-9,10-imine; 9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-iodo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-iodo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine 2-iodo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine; 9,10-dihydro-2,11-dimethyl-9,10-diethylanthracen-9,10-imine; 2-chloro-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine; 9,10-dihydro-1-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine; 9,10-dihydro-2-methoxy-9,10-diethyl-11-methylanthracen-9,10-imine; 9,10-dihydro-9,10-diethyl-1,11-dimethylanthracen-9,10-imine; 9,10-dihydro-2-trifluoromethyl-9,10-diethyl-11-methylanthracen-9,10-imine;
Claim 3
Dependent Claim
37 words
10-dihydro-2-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine; 2-bromo-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine; 2-cyano-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine; 2-methylthio-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 1-isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-(N,N-dimethylsulfamoyl)-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-diethoxymethyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 11-benzyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 10-ethyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 11-benzyl-2,9-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-(3-hydroxypropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-propyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-butyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 1-chloro-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-allyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-cyclopropylmethyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 2-iodo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 10-vinyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 2-methoxy-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-nitro-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-amino-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 3,9,11-trimethyl-9,10-dihydroanthracen-9,10-imine; 2,9,11-trimethyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 9,10-bis(trifluoromethyl)-11-methyl-9,10-dihydroanthracen-9,10-imine; 11-methyl-9,10-dipropyl-9,10-dihydroanthracen-9,10-imine; 11-methyl-9-ethyl-10-propyl-9,10-dihydroanthracen-9,10-imine; 2-carboxaldehyde-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; and 9,10,11-triethyl-9,10-dihydroanthracen-9,10-imine.
Claim 4
Dependent Claim
37 words
10-dihydro-2-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine; 2-bromo-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine; 2-cyano-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine; 2-methylthio-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 1-isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-(N,N-dimethylsulfamoyl)-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-diethoxymethyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 11-benzyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 10-ethyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 11-benzyl-2,9-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-(3-hydroxypropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-propyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-butyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 1-chloro-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-allyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-cyclopropylmethyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 2-iodo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 10-vinyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 2-methoxy-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 2-bromo-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-nitro-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 2-amino-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; 3,9,11-trimethyl-9,10-dihydroanthracen-9,10-imine; 2,9,11-trimethyl-9,10-dihydroanthracen-9,10-imine; 2-chloro-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 9,11-dimethyl-9,10-dihydroanthracen-9,10-imine; 9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine; 9,10-bis(trifluoromethyl)-11-methyl-9,10-dihydroanthracen-9,10-imine; 11-methyl-9,10-dipropyl-9,10-dihydroanthracen-9,10-imine; 11-methyl-9-ethyl-10-propyl-9,10-dihydroanthracen-9,10-imine; 2-carboxaldehyde-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; and 9,10,11-triethyl-9,10-dihydroanthracen-9,10-imine.
Claim 5
Dependent Claim
5 words
2-Bromo-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 6
Dependent Claim
5 words
2-Methoxy-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 7
Dependent Claim
5 words
9,10-Diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 8
Dependent Claim
5 words
2-Chloro-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 9
Dependent Claim
5 words
2-Iodo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 10
Dependent Claim
5 words
2-Bromo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 11
Dependent Claim
5 words
2-Chloro-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 12
Dependent Claim
5 words
2-Iodo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 13
Dependent Claim
5 words
2-Bromo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 14
Dependent Claim
5 words
2-Chloro-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 15
Dependent Claim
5 words
2-Iodo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 16
Dependent Claim
5 words
2-Bromo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 17
Dependent Claim
5 words
9,10-Dihydro-2,11-dimethyl-9,10-diethyl-anthracen-9,10-imine according to claim 1.
Claim 18
Dependent Claim
5 words
2-Chloro-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1.
Claim 19
Dependent Claim
5 words
9,10-Dihydro-1-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1.
Claim 20
Dependent Claim
5 words
9,10-Dihydro-2-methoxy-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1.
Claim 21
Dependent Claim
5 words
9,10-Dihydro-9,10-diethyl-1,11-dimethyl-anthracen-9,10-imine according to claim 1.
Claim 22
Dependent Claim
5 words
9,10-dihydro-2-trifluoromethyl-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1.
Claim 23
Dependent Claim
5 words
9,10-Dihydro-2-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1.
Claim 24
Dependent Claim
5 words
2-Bromo-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1.
Claim 25
Dependent Claim
5 words
2-Cyano-9,10-dihydro-9,10-diethyl-11-methyl-anthracen-9,10-imine according to claim 1.
Claim 26
Dependent Claim
5 words
2-Methylthio-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 27
Dependent Claim
5 words
1-Isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 28
Dependent Claim
5 words
2-Isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 29
Dependent Claim
5 words
2-(N,N-Dimethylsulfamoyl)-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 30
Dependent Claim
5 words
2-Diethoxymethyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 31
Dependent Claim
5 words
11-Benzyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 32
Dependent Claim
5 words
10-Ethyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 33
Dependent Claim
5 words
11-Benzyl-2,9-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 34
Dependent Claim
5 words
11-(3-Hydroxypropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 35
Dependent Claim
5 words
11-Propyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 36
Dependent Claim
5 words
11-Butyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 37
Dependent Claim
5 words
1-Chloro-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 38
Dependent Claim
5 words
11-Allyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 39
Dependent Claim
5 words
11-Cyclopropylmethyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 40
Dependent Claim
5 words
11-(3-Dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 41
Dependent Claim
5 words
2-Iodo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 42
Dependent Claim
5 words
2-Bromo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 43
Dependent Claim
5 words
9-Methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 44
Dependent Claim
5 words
10-Vinyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 45
Dependent Claim
5 words
2-Methoxy-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 46
Dependent Claim
5 words
2-Bromo-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 47
Dependent Claim
5 words
2-Nitro-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 48
Dependent Claim
5 words
2-Amino-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 49
Dependent Claim
5 words
3,9,11-Trimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 50
Dependent Claim
5 words
2,9,11-Trimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 51
Dependent Claim
5 words
2-Chloro-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 52
Dependent Claim
5 words
9,11-Dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 53
Dependent Claim
5 words
9,11-Dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 54
Dependent Claim
5 words
9,10-Bis(trifluoromethyl)-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 55
Dependent Claim
5 words
11-Methyl-9,10-dipropyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 56
Dependent Claim
5 words
11-Methyl-9-ethyl-10-propyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 57
Dependent Claim
5 words
2-Carboxaldehyde-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
Claim 58
Dependent Claim
5 words
9,10,11-Triethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.
References Cited (Backward Citations)
US3726897A
Cited
US3678072A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-19 | 1981-06-20 | 1981-12-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-19 | 1985-06-20 | 1985-12-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-19 | 1989-06-20 | 1989-12-20 | $7700.00 | Window Closed / Lapsed |