EP0322582A2
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EP
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4-Heteroaryl-1,3-Benzodiazepines and 2-substituted-alpha-(heteroaryl)benzeneethanamines, a process for their preparation and their use us medicaments
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1988-11-30
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Granted: —
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Expires: 2008-11-30
Abstract
Abstract The present invention relates to 4-heteroaryl-1,3-benzodiazapines and 2-substituted-a-(heteroaryl)-benzeneethanamines and processes for the preparation thereof. The compounds have antidepressant and anticonvulsant activity and can, therefore, be used as medicaments.
Inventors
- 👤 Lawrence Leo Martin
- 👤 Joseph Francis Payack
- 👤 Salvatore Brucato
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 00:22
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26; C07D213/38; C07D213/54; C07D213/56; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/20; C07D333/24; C07D401/00; C07D401/02; C07D401/04; C07D409/00; C07D409/02; C07D409/04; C07D409/12
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
190 words
A process for the preparation of a compound of the formula I wherein Ar is a radical of the following formulae of wherein R 2 is hydrogen, loweralkyl or loweralkanoyl, Y is halogen, hydroxyl, loweralkyl, loweralkoxy, or trifluoromethyl, n is an integer having a value from 0 to 3 inclusive, p is an integer having a value of 0 or 1, and q is an integer having a value from 0 to 4 inclusive; X is halogen, hydroxyl, nitro, loweralkyl, loweralkoxy, or trifluoromethyl; m is an integer having a value from 0 to 2 inclusive; R is hydrogen, loweralkyl, aryl, aralkyl, cycloalkylloweralkyl, loweralkenyl, or loweralkynyl; and R 1 is hydrogen, loweralkyl, or aralkyl, wherein for each value of m, n, p, or q each X or Y may be the same or different; the optical antipodes, geometrical isomers and pharmaceutically acceptable acid addition salts thereof, which comprises reacting a compound of the formula 5 wherein R' and Ar are as defined in claim 3, with a compound of the formula wherein R is as defined in claim 1 and x is an integer having a value of 1 or 2.
Claim 2
Dependent Claim
40 words
A process as defined in claim 1 wherein R' is methyl, m is 0 or 1 and Ar is a radical of the formulae wherein Y is loweralkyl and n is an integer having a value of 0 or 1.
Claim 3
Dependent Claim
11 words
A process as defined in claim 2 wherein R is loweralkyl.
Claim 4
Dependent Claim
19 words
The process as defined in claim 3 wherein 4,5-dihydro-2-ethyl-3-methyl-4-(2-thienyl)-3H-1,3benzodiazepine, or a pharmaceutically acceptable acid addition salt thereof is prepared.
Claim 5
Dependent Claim
19 words
The process as defined in claim 3 wherein 4,5-dihydro-2-ethyl-3-methyl-4-(3-methyl-2-thienyl)-3H-1,3-benzodiazepine, or a pharmaceutically acceptable acid addition salt thereof, is prepared.
Claim 6
Dependent Claim
18 words
Use of a compound as defined in claim 1 for the preparation of a medicament having antidepressant activity.
Claim 7
Dependent Claim
708 words
A process for the preparation of a compound of the formula II wherein Ar is a radical of the formulae wherein R 2 is hydrogen, loweralkyl or loweralkanoyl, Y is halogen, hydroxyl, loweralkyl, loweralkoxy, or trifluoromethyl, n is an integer having a value from 0 to 3 inclusive, p is an integer having a value of 0 or 1, and q is an integer having a value from 0 to 4 inclusive; X is halogen, hydroxyl, nitro, loweralkyl, loweralkoxy, or trifluoromethyl; m is an integer having a value from 0 to 3 inclusive; R 1 is hydrogen, loweralkyl, or aralkyl; R 3 is hydroxy, loweralkoxy, amino, loweralkylamino, diloweralkylamino or NR 6 C(O)R 4 wherein R 4 and R 6 are independently hydrogen or loweralkyl; and R 5 is hydrogen, loweralkyl or C(O)R 7 where R 7 is hydrogen or loweralkyl; wherein for each value of m, n, p, or q each X or Y may be the same or different; the geometrical isomers, optical antipodes and pharmaceutically acceptable acid addition salts thereof, which comprises a) reacting a compound of the formula 2 wherein X and m are as defined, with a compound of the formula ArCH = NR' where Ar and R 1 are as defined in claim 8 to afford a compound of the formula 4 b) hydrolyzing the compound obtained to afford a compound of the formula II, where R 3 is amino, R 1 and Ar are as defined and R 5 is hydrogen, c) optionally reacting a compound of the formula II, wherein R 3 is amino, R 5 is hydrogen and R 1 and Ar are as defined, with an alcanoic acid anhydride to afford a compound of the formula II, wherein R 3 is amino or the group -NR 6 C(O)R 4 , where R 6 is hydrogen and R 4 is hydrogen or loweralkyl, R 5 is the group where R 7 is hydrogen or loweralkyl, and R 1 and Ar are as defined, d) optionally reducing a compound as obtained in step c) to afford a compound of the formula II, where R 3 is the group -NHR' where R is hydrogen or loweralkyl, R 5 is loweralkyl and R 1 and Ar are as defined, e) optionally treating a compound of the formula II wherein R 3 is amino, R 5 is the group where R 7 is hydrogen or loweralkyl and R 1 and Ar are as defined, with formaldehyde and succinimide followed by reduction of the resultant dioxo-pyrrolidinyl substituted compound of the formula 6c to afford a compound of the formula II where R 3 is -NHCH 3 R 5 is the group where R 7 is hydrogen or loweralkyl, and R 1 and Ar are as defined, f) optionally hydrolyzing the compound as obtained in step c) to afford a compound of the formula II where R 3 is -NHCH 3 , R 5 is hydrogen or loweralkyl and R 1 and Ar are as defined, g) optionally diazotizing a compound of the formula II, where R 3 is amino, R 1 is loweralkyl, R 5 is the group where R 7 is hydrogen or loweralkyl and Ar is as defined above, followed by quenching the resultant compound into aqueous copper sulfate solution, to afford a compound of the formula II, where R 3 is hydroxy, R 1 is loweralkyl, R 5 is the group where R 7 is hydrogen or loweralkyl and Ar is as defined above, h) optionally hydrolyzing a compound as obtained in step g) to afford a compound of the formula II where R 3 is hydroxy, R 1 is loweralkyl, R 5 is hydrogen and Ar is as defined, or i) reducing a compound of the formula 9 wherein Ar, X and m are as defined above, and R 8 is a C 1 -C 5 -alkanoyl, to afford a compound of the formula II, where R 3 is NH 2 and R' and R 5 are both hydrogen. 8. A process as defined in claim 7 wherein R 3 is amino, m is 0 or 1 and Ar is a radical of the formulae wherein Y is loweralkyl and n is an integer having a value of 0 or 1.
Claim 8
Dependent Claim
19 words
The process as defined in claim 9 wherein 2-amino-N-methyl-a-(3-methyl-2-thienyl)-benzeneethanamine or a pharmaceutically acceptable acid addition salt thereof, is prepared.
Claim 9
Dependent Claim
19 words
The process as defined in claim 9 wherein 2-amino-5-bromo-N-methyl-a-(3-methyl-2-thienyl)-benzeneethanamine or a pharmaceutically acceptable acid addition salt thereof, is prepared.
Claim 10
Dependent Claim
18 words
Use of a compound as defined in claim 7 for the preparation of a medicament having anticonvulsant activity.
References Cited (Backward Citations)
No citation records indexed.
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