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 21:28
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.
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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 |