US4588727A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Intermediates for pyrrolo[1,2-b][1,2,5]triazepines
Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1985-02-04
•
Granted: 1986-05-13
•
Expires: 2005-02-04
Abstract
Abstract There are described novel pyrrolo[1,2-b][1,2,5]triazepines of the general formula <IMAGE> where R is hydrogen, loweralkyl, loweralkylaminoloweralkyl or diloweralkylaminoloweralkyl; X is hydrogen, halogen (fluorine, chlorine, bromine or iodine), trifluoromethyl or nitro; and Y is hydrogen, halogen or loweralkyl. Also described are derivatives of 1-amino-2-benzoylpyrrole having the general formula <IMAGE> (II) where R, X and Y are as defined above, and R1 is hydrogen, <IMAGE> <IMAGE> <IMAGE> <IMAGE> +TR <IMAGE> Compounds I and II are useful as analgesic, anxiolytic and/or anticonvulsant agents, and many of Compounds II are useful as intermediates for synthesizing Compounds I.
Inventors
- 👤 Richard C. Effland
- 👤 Joseph T. Klein
- 👤 R. Richard L. Hamer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:23
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D207/00; C07D207/46; C07D207/50
Claims Analysis
Total Claims: 86
Claim 1
Independent Claim
44 words
A compound of the formula ##STR34## where X is hydrogen, halogen, loweralkyl, CF 3 or NO 2 ; Y is hydrogen, halogen or loweralkyl; R is hydrogen, loweralkyl, loweralkylaminoloweralkyl, diloweralkylaminoloweralkyl; and R 1 is hydrogen, ##STR35## or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
44 words
A compound of the formula ##STR34## where X is hydrogen, halogen, loweralkyl, CF 3 or NO 2 ; Y is hydrogen, halogen or loweralkyl; R is hydrogen, loweralkyl, loweralkylaminoloweralkyl, diloweralkylaminoloweralkyl; and R 1 is hydrogen, ##STR35## or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
12 words
The compound as defined in claim 1, where R 1 is aminoacetyl.
Claim 4
Dependent Claim
11 words
The compound as defined in claim 2, where R is methyl.
Claim 5
Dependent Claim
11 words
The compound as defined in claim 3, where Y is hydrogen.
Claim 6
Dependent Claim
14 words
The compound as defined in claim 4, where X is hydrogen, which is 1-(N-methyl-aminoacetamido)-2-benzoylpyrrole.
Claim 7
Dependent Claim
11 words
The compound as defined in claim 4, where X is chlorine.
Claim 8
Dependent Claim
14 words
The compound as defined in claim 6, where X is 2-chloro, which is 1-(N-methyl-aminoacetamido)-2-(2-chlorobenzoyl)pyrrole.
Claim 9
Dependent Claim
11 words
The compound as defined in claim 4, where X is fluorine.
Claim 10
Dependent Claim
14 words
The compound as defined in claim 8, where X is 2-fluoro, which is 1-(N-methyl-aminoacetamido)-2-(2-fluorobenzoyl)pyrrole.
Claim 11
Dependent Claim
12 words
The compound as defined in claim 1, where R 1 is ##STR36##
Claim 12
Dependent Claim
11 words
The compound as defined in claim 10, where R is methyl.
Claim 13
Dependent Claim
11 words
The compound as defined in claim 11, where Y is hydrogen.
Claim 14
Dependent Claim
11 words
The compound as defined in claim 12, where X is hydrogen.
Claim 15
Dependent Claim
11 words
The compound as defined in claim 12, where X is chlorine.
Claim 16
Dependent Claim
14 words
The compound as defined in claim 14, where X is 2-chloro, which is 1-[N-methyl-(t-butoxycarbonylamino)acetamido]-2-(2-chlorobenzoyl)pyrrole.
Claim 17
Dependent Claim
11 words
The compound as defined in claim 12, where X is fluorine.
Claim 18
Dependent Claim
14 words
The compound as defined in claim 16, where X is 2-fluoro, which is 1-[N-methyl-(t-butoxycarbonylamino)acetamido]-2-(2-fluorobenzoyl)pyrrole.
Claim 19
Dependent Claim
11 words
The compound as defined in claim 10, where R is hydrogen.
Claim 20
Dependent Claim
11 words
The compound as defined in claim 18, where Y is hydrogen.
Claim 21
Dependent Claim
11 words
The compound as defined in claim 19, where X is chlorine.
Claim 22
Dependent Claim
14 words
The compound as defined in claim 20, where X is 2-chloro, which is 1-[(t-butoxycarbonylamino)acetamido]-2-(2-chlorobenzoyl)pyrrole.
Claim 23
Dependent Claim
14 words
The compound as defined in claim 19, where X is 2-fluoro, which is 1-[(t-butoxycarbonylamino)acetamido]-2-(2-fluorobenzoyl)pyrrole.
Claim 24
Dependent Claim
12 words
The compound as defined in claim 1, where R 1 is bromoacetyl.
Claim 25
Dependent Claim
11 words
The compound as defined in claim 23, where R is methyl.
Claim 26
Dependent Claim
11 words
The compound as defined in claim 24, where Y is hydrogen.
Claim 27
Dependent Claim
14 words
The compound as defined in claim 25, where X is hydrogen, which is 1-(N-methyl-bromoacetamido)-2-benzoylpyrrole.
Claim 28
Dependent Claim
14 words
The compound as defined in claim 25, where X is 2-chloro, which is 1-(N-methyl-bromoacetamido)-2-(2-chlorobenzoyl)-5-methylpyrrole.
Claim 29
Dependent Claim
11 words
The compound as defined in claim 23, where R is hydrogen.
Claim 30
Dependent Claim
11 words
The compound as defined in claim 28, where Y is hydrogen.
Claim 31
Dependent Claim
14 words
The compound as defined in claim 9, where X is hydrogen, which is 1-bromoacetamido-2-benzoylpyrrole.
Claim 32
Dependent Claim
14 words
The compound as defined in claim 9, where X is 2-fluoro, which is 1-bromoacetamido-2-(2-fluorobenzoyl)pyrrole.
Claim 33
Dependent Claim
18 words
The compound as defined in claim 29, where Y is methyl and X is 2-fluoro, which is 1-bromoacetamido-2-(2-fluorobenzoyl)-5-methylpyrrole.
Claim 34
Dependent Claim
12 words
The compound as defined in claim 1, where R 1 is chloroacetyl.
Claim 35
Dependent Claim
11 words
The compound as defined in claim 33, where R is methyl.
Claim 36
Dependent Claim
18 words
The compound as defined in claim 34, where Y is hydrogen and X is 2-fluoro, which is 1-chloroacetamido-2-(2-fluorobenzoyl)pyrrole.
Claim 37
Dependent Claim
16 words
The compound as defined in claim 1, where R is hydrogen and R 1 is hydrogen.
Claim 38
Dependent Claim
11 words
The compound as defined in claim 36, where Y is hydrogen.
Claim 39
Dependent Claim
14 words
The compound as defined in claim 37, where X is hydrogen, which is 1-amino-2-benzoylpyrrole.
Claim 40
Dependent Claim
14 words
The compound as defined in claim 37, where X is 2-fluoro, which is 1-amino-2-(2-fluorobenzoyl)pyrrole.
Claim 41
Dependent Claim
14 words
The compound as defined in claim 37, where X is 2-chloro, which is 1-amino-2-(2-chlorobenzoyl)pyrrole.
Claim 42
Dependent Claim
11 words
The compound as defined in claim 36, where Y is methyl.
Claim 43
Dependent Claim
14 words
The compound as defined in claim 41, where X is 2-fluoro, which is 1-amino-2-(2-fluorobenzoyl)-5-methylpyrrole.
Claim 44
Dependent Claim
14 words
The compound as defined in claim 41, where X is 2-chloro, which is 1-amino-2-(2-chlorobenzoyl)-5-methylpyrrole.
Claim 45
Dependent Claim
16 words
The compound as defined in claim 1, where R is methyl and R 1 is hydrogen.
Claim 46
Dependent Claim
11 words
The compound as defined in claim 44, where Y is hydrogen.
Claim 47
Dependent Claim
15 words
The compound as defined in claim 45, where X is hydrogen, which is 2-benzoyl-1-methylaminopyrrole hydrobromide.
Claim 48
Dependent Claim
14 words
The compound as defined in claim 45, where X is 2-chloro, which is 2-(2-chlorobenzoyl)-1-methylaminopyrrole.
Claim 49
Dependent Claim
18 words
The compound as defined in claim 44, where Y is methyl and X is 2-chloro, which is 2-(2-chlorobenzoyl)-1-methylamino-5-methylpyrrole.
Claim 50
Dependent Claim
18 words
The compound as defined in claim 1, where R is methyl and R 1 is --CO 2 Et.
Claim 51
Dependent Claim
11 words
The compound as defined in claim 49, where Y is hydrogen.
Claim 52
Dependent Claim
17 words
The compound as defined in claim 50, where X is hydrogen, which is (2-benzoyl-1H-pyrrol-1-yl)-methyl-carbamic acid, ethyl ester.
Claim 53
Dependent Claim
17 words
The compound as defined in claim 50, where X is 2-chloro, which is [2-(2-chlorobenzoyl)-1H-pyrrol-1-yl]-methyl-carbamic acid, ethyl ester.
Claim 54
Dependent Claim
17 words
The compound as defined in claim 50, where X is 2-fluoro, which is [2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]-methyl-carbamic acid, ethyl ester.
Claim 55
Dependent Claim
18 words
The compound as defined in claim 1, where R is hydrogen and R 1 is --CO 2 Et.
Claim 56
Dependent Claim
11 words
The compound as defined in claim 54, where Y is hydrogen.
Claim 57
Dependent Claim
17 words
The compound as defined in claim 55, where X is hydrogen, which is (2-benzoyl-1H-pyrrol-1-yl)-carbamic acid, ethyl ester.
Claim 58
Dependent Claim
17 words
The compound as defined in claim 55, where X is 2-fluoro, which is [2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]-carbamic acid, ethyl ester.
Claim 59
Dependent Claim
17 words
The compound as defined in claim 55, where X is 2-chloro, which is [2-(2-chlorobenzoyl)-1H-pyrrol-1-yl]-carbamic acid, ethyl ester.
Claim 60
Dependent Claim
21 words
The compound as defined in claim 54, where Y is methyl and X is 2-chloro, which is [2-(2-chlorobenzoyl)-5-methyl-1H-pyrrol-1-yl]-carbamic acid, ethyl ester.
Claim 61
Dependent Claim
18 words
The compound as defined in claim 1, where R is dimethylaminoethyl and R 1 is --CO 2 Et.
Claim 62
Dependent Claim
21 words
The compound as defined in claim 60, where Y is hydrogen and X is 2-chloro, which is [2-(2-chlorobenzoyl)-1H-pyrrol-1-yl]-2-[(dimethylamino)ethyl]carbamic acid, ethyl ester.
Claim 63
Dependent Claim
16 words
The compound as defined in claim 1, where R is dimethylaminoethyl and R 1 is hydrogen.
Claim 64
Dependent Claim
11 words
The compound as defined in claim 62, where Y is hydrogen.
Claim 65
Dependent Claim
14 words
The compound as defined in claim 63, where X is hydrogen, which is (2-benzoyl-1H-pyrrol-1-yl)-2-(dimethylamino)ethylamine.
Claim 66
Dependent Claim
14 words
The compound as defined in claim 34, where X is 2-chloro, which is [2-(2-chlorobenzoyl)-1H-pyrrol-1-yl]-2-(dimethylamino)ethylamine.
Claim 67
Dependent Claim
11 words
The compound as defined in claim 2, where R is hydrogen.
Claim 68
Dependent Claim
11 words
The compound as defined in claim 66, where Y is hydrogen.
Claim 69
Dependent Claim
14 words
The compound as defined in claim 67, where X is hydrogen, which is 1-aminoacetamido-2-benzoylpyrrole.
Claim 70
Dependent Claim
14 words
The compound as defined in claim 67, where X is 2-fluoro, which is 1-aminoacetamido-2-(2-fluorobenzoyl)pyrrole.
Claim 71
Dependent Claim
16 words
The compound as defined in claim 1, where R is hydrogen and R 1 is ##STR37##
Claim 72
Dependent Claim
18 words
The compound as defined in claim 70, where Y is hydrogen and X is hydrogen, which is 1-(phthaloyliminoacetamido)-2-benzoylpyrrole.
Claim 73
Dependent Claim
16 words
The compound as defined in claim 1, where R is hydrogen and R 1 is ##STR38##
Claim 74
Dependent Claim
18 words
The compound as defined in claim 72, where Y is hydrogen and X is hydrogen, which is 1-[(carbobenzyloxyamino)acetamido]-2-benzoylpyrrole.
Claim 75
Dependent Claim
25 words
The compound as defined in claim 1, where R is hydrogen, R 1 is ##STR39## Y is hydrogen and X is 2-fluoro, which is 2-(2-fluorobenzoyl)-1-(4-phenylpiperazin-1-ylacetamido)pyrrole.
Claim 76
Dependent Claim
26 words
The compound as defined in claim 1, where R is hydrogen, R 1 is ##STR40## Y is methyl and X is 2-fluoro, which is di-[(2-(2-fluorobenzoyl)-5-methyl-1H-pyrrol-1-yl)-2-acetamido]amine hydrochloride.
Claim 77
Dependent Claim
26 words
The compound as defined in claim 1, where R is methyl and R 1 is ##STR41## Y is methyl and X is 2-chloro, which is 1-(N-methyl-acetylaminoacetylamido)-2-(2-chlorobenzoyl)-5-methylpyrrole.
Claim 78
Dependent Claim
24 words
A compound of the formula ##STR42## where X is hydrogen, halogen, loweralkyl, CF 3 or NO 2 and Y is hydrogen, halogen or loweralkyl.
Claim 79
Dependent Claim
24 words
A compound of the formula ##STR42## where X is hydrogen, halogen, loweralkyl, CF 3 or NO 2 and Y is hydrogen, halogen or loweralkyl.
Claim 80
Dependent Claim
11 words
The compound as defined in claim 77, where Y is hydrogen.
Claim 81
Dependent Claim
14 words
The compound as defined in claim 78, where X is hydrogen, which is 2-benzoyl-1-phthalimidopyrrole.
Claim 82
Dependent Claim
14 words
The compound as defined in claim 78, where X is 2-fluoro, which is 2-(2-fluorobenzoyl)-1-phthalimidopyrrole.
Claim 83
Dependent Claim
14 words
The compound as defined in claim 78, where X is 2-chloro, which is 2-(2-chlorobenzoyl)-1-phthalimidopyrrole.
Claim 84
Dependent Claim
18 words
The compound as defined in claim 77, where Y is methyl and X is 2-chloro, which is 2-(2-chlorobenzoyl)-5-methyl-1-phthalimidopyrrole.
Claim 85
Dependent Claim
58 words
A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of the formula ##STR43## where X is hydrogen, halogen, loweralyl, CF 3 or NO 2 ; Y is hydrogen, halogen or loweralyl; R is hydrogen, loweralkyl, loweralkylaminoloweralkyl, or diloweralylaminoloweralkyl; and R 1 is hydrogen, ##STR44## or a pharmaceutically acceptable acid addition salt thereof and a carrier therefor.
Claim 86
Dependent Claim
58 words
A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of the formula ##STR43## where X is hydrogen, halogen, loweralyl, CF 3 or NO 2 ; Y is hydrogen, halogen or loweralyl; R is hydrogen, loweralkyl, loweralkylaminoloweralkyl, or diloweralylaminoloweralkyl; and R 1 is hydrogen, ##STR44## or a pharmaceutically acceptable acid addition salt thereof and a carrier therefor.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-05-12 | 1989-11-11 | 1990-05-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-05-12 | 1993-11-11 | 1994-05-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-05-12 | 1997-11-11 | 1998-05-13 | $7700.00 | Window Closed / Lapsed |