US4232016A
Expired / Lapsed
US
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3-Fluorobenzodiazepines
Assignee: Merck Patent GmbH
•
Filing: 1975-12-09
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Granted: 1980-11-04
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Expires: 1995-12-09
Abstract
Abstract 3-Fluoro-2,3-dihydro-1H-1,4-benzodiazepin-2-ones of the formula ##STR1## wherein R 1 is H, alkyl or fluorinated alkyl of 1-4 carbon atoms and up to 9 fluorine atoms or cycloalkylalkyl of 4-8 carbon atoms; R 2 is phenyl; monohalophenyl or pyridyl; R 3 is F, Cl, Br or NO 2 , and physiologically acceptable acid addition salts thereof, are central nervous system depressants.
Inventors
- 👤 Eike Poetsch
- 👤 Jurgen Uhl
- 👤 Dieter Marx
- 👤 Wighard Strehlow
- 👤 Helmut Muller-Calgan
- 👤 Giuliano Dolce
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:28
CPC Classifications
C; C07; C07D; C07D243/00; C07D243/06; C07D243/10; C07D243/14; C07D243/16; C07D243/18; C07D243/24
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
55 words
A 3-fluorobenzodiazepine of the formula ##STR12## wherein R 1 is H, alkyl or fluorinated alkyl of 1-4 carbon atoms and up to 9 fluorine atoms or cycloalkylalkyl of 4-8 carbon atoms; R 2 is phenyl, monohalophenyl or pyridyl; R 3 is F, Cl, Br or NO 2 , and physiologically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
55 words
A 3-fluorobenzodiazepine of the formula ##STR12## wherein R 1 is H, alkyl or fluorinated alkyl of 1-4 carbon atoms and up to 9 fluorine atoms or cycloalkylalkyl of 4-8 carbon atoms; R 2 is phenyl, monohalophenyl or pyridyl; R 3 is F, Cl, Br or NO 2 , and physiologically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
15 words
A compound of claim 1, wherein R 1 is H, methyl, ethyl, 2,2,2-trifluoroethyl or cyclopropylmethyl.
Claim 4
Dependent Claim
14 words
A compound of claim 1, wherein R 2 is phenyl, o-fluorophenyl, o-chlorophenyl or 2-pyridyl.
Claim 5
Dependent Claim
15 words
A compound of claim 1, wherein R 3 is F, Cl or NO 2 .
Claim 6
Dependent Claim
24 words
A compound of claim 1, wherein R 1 is H, methyl, ethyl, 2,2,2-trifluoroethyl or cyclopropylmethyl and R 2 is phenyl, o-fluorophenyl, o-chlorophenyl or 2-pyridyl.
Claim 7
Dependent Claim
22 words
A compound of claim 1, wherein R 1 is H, methyl or ethyl and R 2 is phenyl, o-fluorophenyl, o-chlorophenyl or 2-pyridyl.
Claim 8
Dependent Claim
21 words
A compound of claim 1, wherein R 1 is H or methyl and R 2 is phenyl, o-fluorophenyl, o-chlorophenyl or 2-pyridyl.
Claim 9
Dependent Claim
29 words
A compound of claim 1, wherein R 1 is H or methyl, R 2 is phenyl, o-fluorophenyl or o-chlorophenyl and R 3 is F, Cl or NO 2 .
Claim 10
Dependent Claim
19 words
A compound of claim 1, wherein R 1 is H or methyl and R 2 is phenyl or o-chlorophenyl.
Claim 11
Dependent Claim
19 words
A compound of claim 1, wherein R 1 is H and R 2 is phenyl, o-fluorophenyl, o-chlorophenyl or 2-pyridyl.
Claim 12
Dependent Claim
28 words
A compound of claim 1, wherein R 1 is H or methyl, R 2 is phenyl or o-chlorophenyl and R 3 is F, Cl or NO 2 .
Claim 13
Dependent Claim
25 words
A compound of claim 1, wherein R 1 is H or methyl, R 2 is phenyl or o-chlorophenyl and R 3 is F or Cl.
Claim 14
Dependent Claim
6 words
3-Fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 15
Dependent Claim
6 words
1-Methyl-3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 16
Dependent Claim
6 words
1-(2,2,2-Trifluoroethyl)-3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 17
Dependent Claim
6 words
1-Cyclopropylmethyl-3-fluoro-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 18
Dependent Claim
6 words
3-Fluoro-5-o-chlorophenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 19
Dependent Claim
6 words
1-Methyl-3-fluoro-5-o-chlorophenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 20
Dependent Claim
6 words
3-Fluoro-5-(2-pyridyl)-7-bromo-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 21
Dependent Claim
6 words
1-Methyl-3-fluoro-5-(2-pyridyl)-7-bromo-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 22
Dependent Claim
6 words
3-Fluoro-5-phenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 23
Dependent Claim
6 words
3-Fluoro-5-o-fluorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 24
Dependent Claim
6 words
1-Methyl-3-fluoro-5-o-fluorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 25
Dependent Claim
6 words
3-Fluoro-5-o-chlorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 26
Dependent Claim
6 words
1-Methyl-3-fluoro-5-o-chlorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 27
Dependent Claim
6 words
3,7-Difluoro-5-o-chlorophenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 28
Dependent Claim
6 words
1-Methyl-3,7-difluoro-5-o-chlorophenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one, a compound of claim 1.
Claim 29
Dependent Claim
31 words
A pharmaceutical composition in unit dosage form comprising a central nervous system depressant effective amount per unit dosage of a compound of claim 1, in admixture with a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
40 words
A method of depressing central nervous system activity in mammals comprising administering to a patient a daily dosage of a compound of claim 1, in admixture with a pharmaceutically acceptable carrier, effective to induce a muscle-relaxing, anticonvulsive or anxiolytic effect.
Claim 31
Dependent Claim
17 words
The method of claim 29, wherein the daily dosage is 0.002 to 1.0 mg./kg. of body weight.
Claim 32
Dependent Claim
10 words
A pharmaceutical composition of claim 28 adapted for oral administration.
Claim 33
Dependent Claim
12 words
A pharmaceutical composition of claim 31 in tablet, dragee or capsule form.
Claim 34
Dependent Claim
17 words
A pharmaceutical composition of claim 31 wherein the unit dosage amount is between 1 and 20 mg.
Claim 35
Dependent Claim
11 words
A method according to claim 29 wherein the administration is oral.
Claim 36
Dependent Claim
43 words
A compound of the formula: ##STR13## wherein R 1 is hydrogen or alkyl having 1 to 4 carbon atoms; R 2 is phenyl, monohalophenyl or pyridyl; R 3 is F, Cl, Br or NO 2 , and pharmaceutically acceptable acid addition salts thereof.
Claim 37
Dependent Claim
43 words
A compound of the formula: ##STR13## wherein R 1 is hydrogen or alkyl having 1 to 4 carbon atoms; R 2 is phenyl, monohalophenyl or pyridyl; R 3 is F, Cl, Br or NO 2 , and pharmaceutically acceptable acid addition salts thereof.
Claim 38
Dependent Claim
28 words
A muscle-relaxing, anti-convulsive and anxiolytic composition which comprises an amount effective for the aforesaid uses of a compound of claim 35 in admixture with a pharmaceutically acceptable carrier.
Claim 39
Dependent Claim
26 words
A method for producing muscle relaxation in mammals which comprises administering an effective skeletal muscle relaxant amount of a compound of claim 35 to the mammal.
Claim 40
Dependent Claim
23 words
A method for relieving anxiety in mammals which comprises administering an effective anxiolytic amount of a compound of claim 35 to the mammal.
Claim 41
Dependent Claim
49 words
A compound of the formula ##STR14## wherein R 1 is hydrogen, alkyl having 1 to 4 carbon atoms or --CH 2 CF 3 ; R 2 is phenyl, monohalophenyl or pyridyl; R 3 is F, Cl, Br or NO 2 , and the pharmaceutically acceptable acid addition salts thereof.
Claim 42
Dependent Claim
49 words
A compound of the formula ##STR14## wherein R 1 is hydrogen, alkyl having 1 to 4 carbon atoms or --CH 2 CF 3 ; R 2 is phenyl, monohalophenyl or pyridyl; R 3 is F, Cl, Br or NO 2 , and the pharmaceutically acceptable acid addition salts thereof.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-04 | 1984-05-05 | 1984-11-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-04 | 1988-05-05 | 1988-11-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-04 | 1992-05-05 | 1992-11-04 | $7700.00 | Window Closed / Lapsed |