US4150139A
Expired / Lapsed
US
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Triazolobenzazepine derivatives
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1977-08-03
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Granted: 1979-04-17
•
Expires: 1997-08-03
Abstract
Abstract Novel triazolobenzazepine derivatives of the formula ##STR1## (wherein R 1 and R 2 are hydrogen or alkyl, X is ##STR2## wherein R 3 and R 4 are hydrogen, alkyl, aryl or aralkyl, and R 5 is hydrogen or alkyl), Z is --SR 6 , --S(O) n R 6 or --OR 7 (wherein R 6 and R 7 are alkyl or aralkyl, and n is 1 or 2), and Ring A is unsubstituted or substituted with at least one of halogen, lower alkyl, lower alkoxy and trifluoromethyl, and their physiologically acceptable salts have excellent pharmacological activities and are useful as medicines such as muscle-relaxants, analgesics and antiinflammatory drugs.
Inventors
- 👤 Yutaka Kuwada
- 👤 Hiroyuki Tawada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 22:22
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/12
Claims Analysis
Total Claims: 63
Claim 1
Independent Claim
115 words
A compound of the formula ##STR19## wherein R 1 and R 2 are hydrogen or alkyl having 1 to 4 carbon atoms, X is ##STR20## wherein R 3 and R 4 are hydrogen, alkyl having 1 to 4 carbon atoms, phenyl, or phenyl-C 1-4 alkyl, and R 5 is hydrogen or alkyl having 1 to 4 carbon atoms, Z is --SR 6 , --S(O)nR 6 or --OR 7 wherein R 6 and R 7 are alkyl having 1-4 carbon atoms or phenyl-C 1-4 alkyl, and n is 1 or 2, and Ring A is unsubstituted or substituted with from one to four of halogen, lower alkyl, lower alkoxy and trifluoromethyl, or its physiologically acceptable salts.
Claim 2
Dependent Claim
115 words
A compound of the formula ##STR19## wherein R 1 and R 2 are hydrogen or alkyl having 1 to 4 carbon atoms, X is ##STR20## wherein R 3 and R 4 are hydrogen, alkyl having 1 to 4 carbon atoms, phenyl, or phenyl-C 1-4 alkyl, and R 5 is hydrogen or alkyl having 1 to 4 carbon atoms, Z is --SR 6 , --S(O)nR 6 or --OR 7 wherein R 6 and R 7 are alkyl having 1-4 carbon atoms or phenyl-C 1-4 alkyl, and n is 1 or 2, and Ring A is unsubstituted or substituted with from one to four of halogen, lower alkyl, lower alkoxy and trifluoromethyl, or its physiologically acceptable salts.
Claim 3
Dependent Claim
32 words
The compound according to claim 1, wherein X is ##STR21## wherein R 3 and R 4 are defined as above, and Z is --SR 6 wherein R 6 is defined as above.
Claim 4
Dependent Claim
17 words
The compound according to claim 2, wherein R 6 is alkyl having 1 to 4 carbon atoms.
Claim 5
Dependent Claim
13 words
The compound according to claim 2, wherein R 6 is phenyl-C 1-4 alkyl.
Claim 6
Dependent Claim
20 words
The compound according to claim 1, wherein Z is --S(O)nR 6 (wherein R 6 and n are defined as above).
Claim 7
Dependent Claim
17 words
The compound according to claim 5, wherein R 6 is alkyl having 1 to 4 carbon atoms.
Claim 8
Dependent Claim
13 words
The compound according to claim 5, wherein R 6 is phenyl-C 1-4 alkyl.
Claim 9
Dependent Claim
18 words
The compound according to claim 1, wherein Z is --OR 7 wherein R 7 is defined as above.
Claim 10
Dependent Claim
17 words
The compound according to claim 8, wherein R 7 is alkyl having 1 to 4 carbon atoms.
Claim 11
Dependent Claim
13 words
The compound according to claim 8, wherein R 7 is phenyl-C 1-4 alkyl.
Claim 12
Dependent Claim
14 words
The compound according to claim 1, wherein R 1 and R 2 are hydrogen.
Claim 13
Dependent Claim
20 words
The compound according to claim 1, wherein R 1 and R 2 are alkyl having 1 to 4 carbon atoms.
Claim 14
Dependent Claim
20 words
The compound according to claim 1, wherein X is ##STR22## wherein R 3 and R 4 are defined as above.
Claim 15
Dependent Claim
14 words
The compound according to claim 13, wherein R 3 and R 4 are hydrogen.
Claim 16
Dependent Claim
20 words
The compound according to claim 13, wherein R 3 and R 4 are alkyl having 1 to 4 carbon atoms.
Claim 17
Dependent Claim
14 words
The compound according to claim 13, wherein R 3 and R 4 are phenyl.
Claim 18
Dependent Claim
16 words
The compound according to claim 13, wherein R 3 and R 4 are phenyl-C 1-4 alkyl.
Claim 19
Dependent Claim
10 words
The compound according to claim 1, wherein X is ##STR23##
Claim 20
Dependent Claim
17 words
The compound according to claim 1, wherein X is ##STR24## wherein R 5 is defined as above.
Claim 21
Dependent Claim
11 words
The compound according to claim 19, wherein R 5 is hydrogen.
Claim 22
Dependent Claim
17 words
The compound according to claim 19, wherein R 5 is alkyl having 1 to 4 carbon atoms.
Claim 23
Dependent Claim
11 words
The compound according to claim 1, wherein Ring A is unsubstituted.
Claim 24
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 25
Dependent Claim
8 words
The compound according to claim 1, namely, 3-ethylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 26
Dependent Claim
8 words
The compound according to claim 1, namely, 6-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 27
Dependent Claim
8 words
The compound according to claim 1, namely, 11-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 28
Dependent Claim
8 words
The compound according to claim 1, namely, 8-chloro-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 29
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methylthio-11-phenyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 30
Dependent Claim
8 words
The compound according to claim 1, namely, 8-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 31
Dependent Claim
8 words
The compound according to claim 1, namely, 8-methoxy-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 32
Dependent Claim
8 words
The compound according to claim 1, namely, 9-methoxy-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 33
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methylthio-11H-s-triazolo[3,4-b][3]benzazepin-11-one.
Claim 34
Dependent Claim
8 words
The compound according to claim 1, namely, 8-chloro-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepin-11-one.
Claim 35
Dependent Claim
8 words
The compound according to claim 1, namely, 8-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepin-11-one.
Claim 36
Dependent Claim
8 words
The compound according to claim 1, namely, 11-methylene-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 37
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 38
Dependent Claim
8 words
The compound according to claim 1, namely, 8-methyl-3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 39
Dependent Claim
8 words
The compound according to claim 1, namely 8-chloro-3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 40
Dependent Claim
8 words
The compound according to claim 1, namely, 8-methoxy-3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 41
Dependent Claim
8 words
The compound according to claim 1, namely, 9-methoxy-3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 42
Dependent Claim
8 words
The compound according to claim 1, namely, 3-ethylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 43
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methylsulfonyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 44
Dependent Claim
8 words
The compound according to claim 1, namely, 8-methyl-3-methylsulfonyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 45
Dependent Claim
8 words
The compound according to claim 1, namely, 8-chloro-3-methylsulfonyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 46
Dependent Claim
8 words
The compound according to claim 1, namely, 8-methoxy-3-methylsulfonyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 47
Dependent Claim
8 words
The compound according to claim 1, namely, 9-methoxy-3-methylsulfonyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 48
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methylsulfonyl-11-phenyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 49
Dependent Claim
8 words
The compound according to claim 1, namely, 11-methyl-3-methylsulfonyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 50
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepin-11-one.
Claim 51
Dependent Claim
8 words
The compound according to claim 1, namely, 11-methylene-3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 52
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methoxy-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 53
Dependent Claim
8 words
The compound according to claim 1, namely, 3-ethoxy-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 54
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methoxy-8-methyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 55
Dependent Claim
8 words
The compound according to claim 1, namely, 8-chloro-3-methoxy-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 56
Dependent Claim
8 words
The compound according to claim 1, namely, 3,8-dimethoxy-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 57
Dependent Claim
8 words
The compound according to claim 1, namely, 3,9-dimethoxy-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 58
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methoxy-11-phenyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 59
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methoxy-11-methyl-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 60
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methoxy-11-methylene-11H-s-triazolo[3,4-b][3]benzazepine.
Claim 61
Dependent Claim
8 words
The compound according to claim 1, namely, 3-methoxy-11H-s-triazolo[3,4-b][3]benzazepin-11-one.
Claim 62
Dependent Claim
151 words
A pharmaceutical composition which comprises (A) as the active ingredient, an analgesically, antiinflammatory- or muscle relaxant-effective amount of at least one compound selected from the group consisting of compounds of the formula ##STR25## wherein R 1 and R 2 are hydrogen or alkyl having 1 to 4 carbon atoms, X is ##STR26## wherein R 3 and R 4 are hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or phenyl-C 1-4 alkyl, and R 5 is hydrogen or alkyl having 1 to 4 carbon atoms, Z is --SR 6 , --S(O)nR 6 or --OR 7 wherein R 6 and R 7 are alkyl having 1 to 4 carbon atoms or phenyl-C 1-4 -alkyl, and n is 1 or 2, and Ring A is unsubstituted or substituted with from one to four of halogen, lower alkyl, lower alkoxy and trifluoromethyl, and physiologically acceptable salts thereof, and (B) a pharmaceutically acceptable carrier therefor.
Claim 63
Dependent Claim
151 words
A pharmaceutical composition which comprises (A) as the active ingredient, an analgesically, antiinflammatory- or muscle relaxant-effective amount of at least one compound selected from the group consisting of compounds of the formula ##STR25## wherein R 1 and R 2 are hydrogen or alkyl having 1 to 4 carbon atoms, X is ##STR26## wherein R 3 and R 4 are hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or phenyl-C 1-4 alkyl, and R 5 is hydrogen or alkyl having 1 to 4 carbon atoms, Z is --SR 6 , --S(O)nR 6 or --OR 7 wherein R 6 and R 7 are alkyl having 1 to 4 carbon atoms or phenyl-C 1-4 -alkyl, and n is 1 or 2, and Ring A is unsubstituted or substituted with from one to four of halogen, lower alkyl, lower alkoxy and trifluoromethyl, and physiologically acceptable salts thereof, and (B) a pharmaceutically acceptable carrier therefor.
References Cited (Backward Citations)
DE2442987A1
Cited
US4002638A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-16 | 1982-10-16 | 1983-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-16 | 1986-10-16 | 1987-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-16 | 1990-10-16 | 1991-04-17 | $7700.00 | Window Closed / Lapsed |