US4075225A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pyrrolo[2,1-b][3]benzazepines
Assignee: Merck and Co Inc
•
Filing: 1976-06-29
•
Granted: 1978-02-21
•
Expires: 1996-06-29
Abstract
Abstract 6,11-Dihydro-5H-Pyrrolo[2,1-b][3]benzazepin-11-one and derivatives thereof are generally prepared by Friedel-Crafts ring closure of a N-phenethylpyrrole-2-carboxylic acid halide. They are useful intermediates in the synthesis of skeletal muscle relaxants and tranquilizers such as 11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benza zepine.
Inventors
- 👤 Joshua Rokach
- 👤 Joseph G. Atkinson
- 👤 Clarence S. Rooney
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 07:28
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/337; C07C; C07C229/00; C07C229/38; C07D207/34; C07D217/00; C07D217/22; C07D217/24; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
136 words
A compound of structural formula: ##STR15## wherein n is [3, 2, ]1, or 0 (X is hydrogen); m is [4, 3, 2,[1 or 0 (Y is hydrogen); and X and Y are independently selected from (1) hydrogen, (2) halo, (3) formyl, (4) lower alkanoyl, (5) lower alkyl, (6) lower alkoxycarbonyl, (7) hydroxy-lower alkyl, (8) perhalo-lower alkyl, (9) lower alkoxy, (10) cyano, (11) perhalo-lower alkylthio, (12) lower alkylthio, (13) lower alkylsulfonyl, (14) perhalo-lower alkylsulfonyl, (15) lower alkylsulfinyl, (16) perhalo-alkylsulfinyl, (17) amino, (18) lower alkanoylamino, (19) lower alkylamino, (20)di(lower alkyl)amino, (21) hydroxy, (22) N-lower alkylcarbamoyl, (23) N,N-di(lower alkyl)carbamoyl, (24) nitro, (25) di(lower alkyl)sulfamoyl, (26) lower alkoxycarbonylamino, (27) N-loweralkyl-carbamoyloxy, (28) carboxy, and (29) carbamoyl; with the proviso that if m is 0 (Y is hydrogen), n is 1 and X is --CN, X is in the 2 or 3-position.
Claim 2
Dependent Claim
136 words
A compound of structural formula: ##STR15## wherein n is [3, 2, ]1, or 0 (X is hydrogen); m is [4, 3, 2,[1 or 0 (Y is hydrogen); and X and Y are independently selected from (1) hydrogen, (2) halo, (3) formyl, (4) lower alkanoyl, (5) lower alkyl, (6) lower alkoxycarbonyl, (7) hydroxy-lower alkyl, (8) perhalo-lower alkyl, (9) lower alkoxy, (10) cyano, (11) perhalo-lower alkylthio, (12) lower alkylthio, (13) lower alkylsulfonyl, (14) perhalo-lower alkylsulfonyl, (15) lower alkylsulfinyl, (16) perhalo-alkylsulfinyl, (17) amino, (18) lower alkanoylamino, (19) lower alkylamino, (20)di(lower alkyl)amino, (21) hydroxy, (22) N-lower alkylcarbamoyl, (23) N,N-di(lower alkyl)carbamoyl, (24) nitro, (25) di(lower alkyl)sulfamoyl, (26) lower alkoxycarbonylamino, (27) N-loweralkyl-carbamoyloxy, (28) carboxy, and (29) carbamoyl; with the proviso that if m is 0 (Y is hydrogen), n is 1 and X is --CN, X is in the 2 or 3-position.
Claim 3
Dependent Claim
1 words
2,3-Dichloro-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 4
Dependent Claim
1 words
2,3-Dichloro-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 5
Dependent Claim
17 words
The compound of claim 1 of structural formula: ##STR16## wherein X and Y are as defined therein.
Claim 6
Dependent Claim
23 words
The compound of claim 3, wherein one of X and Y is hydrogen and the other is hydrogen, cyano, or C 2-6 alkanoyl.
Claim 7
Dependent Claim
8 words
The compound of claim 4 which is 6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 8
Dependent Claim
8 words
The compound of claim 4 which is 2-cyano-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 9
Dependent Claim
8 words
The compound of claim 4 which is 2-pentanoyl-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 10
Dependent Claim
1 words
9-Chloro-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 11
Dependent Claim
1 words
9-Chloro-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 12
Dependent Claim
2 words
2,3-Dibromo-6,11-dihydro-5H-pyrrolo[2,1-b] [3]benzazepin-11-one.
Claim 13
Dependent Claim
2 words
2,3-Dibromo-6,11-dihydro-5H-pyrrolo[2,1-b] [3]benzazepin-11-one.
Claim 14
Dependent Claim
1 words
2,3-Dibromo-9-N-methylcarbamoyloxy-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 15
Dependent Claim
1 words
2,3-Dibromo-9-N-methylcarbamoyloxy-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 16
Dependent Claim
1 words
2,3-Dibromo-9-methoxycarbonylamino-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 17
Dependent Claim
1 words
2,3-Dibromo-9-methoxycarbonylamino-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 18
Dependent Claim
1 words
2,3-Dibromo-9-methyl-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 19
Dependent Claim
1 words
2,3-Dibromo-9-methyl-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 20
Dependent Claim
1 words
1,2,3-Tribromo-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 21
Dependent Claim
1 words
1,2,3-Tribromo-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 22
Dependent Claim
2 words
1,3-Dibromo-2-methyl-6,11-dihydro-5H-pyrrolo [2,1-b][3]benzazepin-11-one.
Claim 23
Dependent Claim
2 words
1,3-Dibromo-2-methyl-6,11-dihydro-5H-pyrrolo [2,1-b][3]benzazepin-11-one.
Claim 24
Dependent Claim
1 words
1,2,3-Tribromo-9-acetylamino-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 25
Dependent Claim
1 words
1,2,3-Tribromo-9-acetylamino-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 26
Dependent Claim
1 words
2,3-Dibromo-9-isopropyl-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 27
Dependent Claim
1 words
2,3-Dibromo-9-isopropyl-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one.
Claim 28
Dependent Claim
2 words
2,3-Dibromo-9-metylthio-6,11-dihydro-5H-pyrrolo [2,1-b][3]benzazepin-11-one.
Claim 29
Dependent Claim
2 words
2,3-Dibromo-9-metylthio-6,11-dihydro-5H-pyrrolo [2,1-b][3]benzazepin-11-one.
Claim 30
Dependent Claim
2 words
2-Cyano-8,9-dimethyl-6,11-dihydro-5H-pyrrolo [2,1-b]benzazepin-11-one.
Claim 31
Dependent Claim
2 words
2-Cyano-8,9-dimethyl-6,11-dihydro-5H-pyrrolo [2,1-b]benzazepin-11-one.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-20 | 1981-08-22 | 1982-02-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-20 | 1985-08-22 | 1986-02-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-20 | 1989-08-22 | 1990-02-21 | $7700.00 | Window Closed / Lapsed |