Patent US4803199A successfully refreshed from Google Patents.
US4803199A
Expired / Lapsed
US
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Pharmaceutically useful heterocyclic and carbocyclic acid esters and amides of alkylene bridged piperidines
Assignee: Novartis AG
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Filing: 1987-11-25
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Granted: 1989-02-07
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Expires: 2007-11-25
Abstract
Abstract The dicarboxylic, heterocyclic and substituted benzoic acid alkylene bridged piperidyl amides and esters are serotonin M antagonists.
Inventors
- 👤 Peter Donatsch
- 👤 Gunter Engel
- 👤 Bruno Hugi
- 👤 Brian P. Richardson
- 👤 Paul A. Stadler, deceased
- 👤 heir by Hildegard R. Stadler
- 👤 heir by Brigitte M. Stadler
- 👤 heir by Sigrid A. Stadler
- 👤 legal representative by Gerald Breuleux
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:44
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02; C07D451/04; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/42; C07D233/00; C07D233/04; C07D233/06; C07D451/06; C07D451/12; C07D451/14; C07D453/00; C07D453/02; C07D471/00; C07D471/02; C07D471/08
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
160 words
A compound in free base form of formula I: A--CO--B--D I wherein A is a group of formula II ##STR13## wherein the free valence is attached to the fused benzene ring; X is --CH 2 --, --NR 3 --, --O-- or --S--; R 1 and R 2 , independently, are hydrogen, halogen, (C 1-4 )alkyl, (C 1-4 )alkoxy, hydroxy, amino, (C 1-4 )alkylamino, di-(C 1-4 )alkylamino, mercapto or (C 1-4 )alkylthio; and R 3 is hydrogen, (C 1-4 )alkyl, (C 3-5 )alkenyl, unsubstituted phenyl, phenyl monosubstituted by (C 1-4 )alkyl, halogen, hydroxy or (C 1-4 )alkoxy, or unsubstituted phenyl (C 1-4 )alkyl; B is --O-- or --NH--; and D is a group of formula IV ##STR14## wherein n is 2, 3, or 4, and R 8 is hydrogen, (C 1-7 )alkyl, (C 3-5 )alkenyl or unsubstituted phenyl (C 1-4 )alkyl; or D is a group of formula V ##STR15## or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 2
Dependent Claim
160 words
A compound in free base form of formula I: A--CO--B--D I wherein A is a group of formula II ##STR13## wherein the free valence is attached to the fused benzene ring; X is --CH 2 --, --NR 3 --, --O-- or --S--; R 1 and R 2 , independently, are hydrogen, halogen, (C 1-4 )alkyl, (C 1-4 )alkoxy, hydroxy, amino, (C 1-4 )alkylamino, di-(C 1-4 )alkylamino, mercapto or (C 1-4 )alkylthio; and R 3 is hydrogen, (C 1-4 )alkyl, (C 3-5 )alkenyl, unsubstituted phenyl, phenyl monosubstituted by (C 1-4 )alkyl, halogen, hydroxy or (C 1-4 )alkoxy, or unsubstituted phenyl (C 1-4 )alkyl; B is --O-- or --NH--; and D is a group of formula IV ##STR14## wherein n is 2, 3, or 4, and R 8 is hydrogen, (C 1-7 )alkyl, (C 3-5 )alkenyl or unsubstituted phenyl (C 1-4 )alkyl; or D is a group of formula V ##STR15## or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 3
Dependent Claim
41 words
A compound according to claim 1 of formula I wherein A, X, R 1 , R 2 , R 3 , B, D, n and R 8 are as defined in claim 1, or a pharmaceutically acceptable acid addition salt threreof.
Claim 4
Dependent Claim
113 words
A compound according to claim 1 of formula I wherein A is a group of formula II wherein the free valence is attached to the fused benzene ring in the 4- or 5-position, R 1 and R 2 , independently, are hydrogen, halogen, (C 1-4 )alkyl of (C 1-4 )alkoxy, R 1 , is in the 4 or 5-position, R 3 is hydrogen or (C 1-4 )alkyl, and D is a group of formula IV wherein R 8 is hydrogen, (C 1-4 )alkyl or benzyl or D is a group of formula V wherein the free valence is attached to the 3-position, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 5
Dependent Claim
35 words
A compound according to claim 3 wherein A, R 1 , R 2 , R 3 , D and R 8 are as defined in claim 3, or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
21 words
A compound according to claim 1 wherein n is 4, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 7
Dependent Claim
23 words
A compound of claim 1 which is indol-4-yl carboxylic acid endo-8-methyl-8-aza-bicyclo[3.2.1.]oct-3-yl ester, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 8
Dependent Claim
20 words
A compound of claim 6 which is indol-4-yl carboxylic acid endo-8-methyl-8-aza-bicyclo[3.2.1.]oct-3-yl ester, or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
21 words
A compound according to claim 1 wherein B is --O--, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 10
Dependent Claim
25 words
A compound according to claim 1 wherein D is a group of formula IV, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 11
Dependent Claim
21 words
A compound according to claim 1 wherein n is 3, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 12
Dependent Claim
25 words
A compound according to claim 1 wherein D is a compound of formula V, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 13
Dependent Claim
21 words
A compound according to claim 1 wherein A is indolyl, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 14
Dependent Claim
17 words
A compound of claim 12 wherein A is indolyl, or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
12 words
A compound of claim 1 which is 3-iodo-indol-4-yl carboxylic acid endo-8-methyl-8-aza-bicyclo[3.2.1.]oct-3-yl ester.
Claim 16
Dependent Claim
12 words
A compound of claim 1 which is indol-4-yl carboxylic acid endo-8-methyl-8-aza-bicyclo[3.2.1.]oct-3-yl ester.
Claim 17
Dependent Claim
30 words
A compound of claim 1 wherein D is a group of formula IV, A represents indol-5-yl, B is O, n=2, R 8 is CH 3 and the configuration is endo.
Claim 18
Dependent Claim
30 words
A compound of claim 1 where D is a group of formula IV, A represents indol-4-yl, B is NH, n=2, R 8 is CH 3 and the configuration is exo.
Claim 19
Dependent Claim
30 words
A compound of claim 1 wherein D is a group of formula IV, A represents indol-4-yl, B is NH, n=2, R 8 is CH 3 and the configuration is endo.
Claim 20
Dependent Claim
30 words
A compound of claim 1 wherein D is a group of formula IV, A represents indol-5-yl, B is NH, n=2, R 8 is CH 3 and the configuration is endo.
Claim 21
Dependent Claim
41 words
A method of inducing a serotonin M receptor antagonist effect comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 22
Dependent Claim
36 words
A method of treating algesia comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 23
Dependent Claim
37 words
A method of treating migraine headaches comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 24
Dependent Claim
36 words
A method of treating arrhythmia comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 25
Dependent Claim
49 words
A pharmaceutical composition useful for inducing a serotonin M receptor antagonist effect and in treating algesia, igraine headaches and arrhythmia comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
References Cited (Backward Citations)
US3170927A
Cited
US2478134A
Cited
GB774858A
Cited
US3342826A
Cited
US3405134A
Cited
NL6807287A
Cited
US3702324A
Cited
GB1293446A
Cited
US4093734A
Cited
US4213983A
Cited
EP0013138A1
Cited
US4273778A
Cited
EP0081054A2
Cited
GB2042522A
Cited
EP0042705A1
Cited
GB2088364A
Cited
EP0067770A2
Cited
US4499099A
Cited
EP0068700A1
Cited
US4459300A
Cited
EP0076592A2
Cited
GB2125398A
Cited
FR2531083A1
Cited
DE3322574A1
Cited
EP0099789A1
Cited
US4657911A
Cited
EP0111607A1
Cited
EP0115933A2
Cited
WO1984003281A1
Cited
EP0127529A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-02-07 | 1992-08-08 | 1993-02-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-02-07 | 1996-08-08 | 1997-02-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-02-07 | 2000-08-08 | 2001-02-07 | $7700.00 | Window Closed / Lapsed |