Patent US2140885A successfully refreshed from Google Patents.
Patent US3381049A successfully refreshed from Google Patents.
US4789673A
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Heterocyclic carboxylic acid amides and esters
Assignee: Novartis AG
•
Filing: 1987-11-10
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Granted: 1988-12-06
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Expires: 2007-11-10
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
- 👤 Hildegard R. Stadler
- 👤 Brigitte M. Stadler
- 👤 Sigrid A. Stadler
- 👤 Gerald Breuleux
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 20:55
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02; C07D451/04; A; A61; A61P; A61P25/00; A61P25/04; A61P25/06; A61P43/00; A61P9/00; A61P9/06; 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: 35
Claim 1
Independent Claim
133 words
A compound of formula I: A--CO--B--D I wherein A is a group of formula II ##STR7## wherein the free valence is attached to the fused ring X; 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; R 3 is hydrogen or (C 1-4 )alkyl; B is --O-- or --NH--; and D is a group of formula IV ##STR8## 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 ##STR9## or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 2
Dependent Claim
133 words
A compound of formula I: A--CO--B--D I wherein A is a group of formula II ##STR7## wherein the free valence is attached to the fused ring X; 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; R 3 is hydrogen or (C 1-4 )alkyl; B is --O-- or --NH--; and D is a group of formula IV ##STR8## 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 ##STR9## 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 13, or a pharmaceutically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
88 words
A compound according to claim 1 wherein A is a group of formula II wherein the free valence is attached to the fused ring X in the 3-position, R 1 and R 2 , independently, are hydrogen, halogen, (C 1-4 )alkyl or (C 1-4 )alkoxy, R 1 is in the 4- or 5-position, and D is a group of formula IV wherein R 8 is hydrogen, (C 1-4 )alkyl or benzyl, or a group of formula V, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 5
Dependent Claim
32 words
A compound according to claim 3 of formula I wherein R 1 , R 2 and R 8 are as defined in claim 15, or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
23 words
A compound of claim 1 which is N-(endo-9-methyl-aza-bicyclo [3.3.1]non-3-yl)indol-3-yl carboxylic acid amide, 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-3-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-3-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
24 words
A compound of claim 1 which is 1-methyl-N-(endo-9-methyl-aza-bicyclo[3.3.1.]non-3-y 1) indol-3-yl carboxylic acid amide, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 10
Dependent Claim
24 words
A compound of 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
20 words
A compound of claim 1 wherein n is 3, or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 12
Dependent Claim
24 words
A compound of claim 1 wherein D is a group of formula V or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 13
Dependent Claim
20 words
A compound of 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
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 16
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 17
Dependent Claim
38 words
A method of treating heart circulation disorders 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 18
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 19
Dependent Claim
50 words
A pharmaceutical composition useful for inducing a serotonin M receptor antagonist effect and in treating algesia, heart circulation disorders 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.
Claim 20
Dependent Claim
12 words
A compound of claim 1 which is 2-methoxy-indol-3-yl carboxylic acid (endo-8-methyl-8-aza-bicyclo[3.2.1.]oct-3-yl) ester.
Claim 21
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 5-chloro-indol-3-yl, B is 0, R 8 is CH 3 and the configuration is endo.
Claim 22
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 4-methoxy-indol-3-yl, B is 0, R 8 is CH 3 and the configuration is endo.
Claim 23
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 5-methoxy-indol-3-yl, B is 0, R 8 is CH 3 and the configuration is endo.
Claim 24
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 1-methyl-indol-3-yl, B is 0, R 8 is CH 3 and the configuration is endo.
Claim 25
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is indol-3-yl, B is 0, R 8 is CH 3 and the configuration is exo.
Claim 26
Dependent Claim
35 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is indol-3-yl, B is 0, R 8 is n-C 3 H 7 and the configuration is endo.
Claim 27
Dependent Claim
32 words
A compound of claim 1 wherein D is a group of formula IV, and n=2 and where A is indol-3-yl, B is 0, R 8 is benzyl and the configuration is exo.
Claim 28
Dependent Claim
32 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is indol-3-yl, B is 0, R 8 is benzyl and the configuration is endo.
Claim 29
Dependent Claim
32 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is indol-3-yl, B is 0, R 8 is H and the configuration is endo.
Claim 30
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 5-fluoro-indol-3-yl, B is NH, R 8 is CH 3 and the configuration is endo.
Claim 31
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 1-methyl-indol-3-yl, B is NH, R 8 is CH 3 and the configuration is endo.
Claim 32
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 2-methyl-indol-3-yl, B is NH, R 8 is CH 3 and the configuration is endo.
Claim 33
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is indol-3-yl, B is NH, R 8 is CH 3 and the configuration is exo.
Claim 34
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is indol-3-yl, B is NH, R 8 is CH 3 and the configuration is endo.
Claim 35
Dependent Claim
33 words
A compound of claim 1 where D is a group of formula IV, and n=2 and where A is 5-chloro-indol-3-yl, B is NH, R 8 is CH 3 and the configuration is endo.
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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) | 1991-12-06 | 1992-06-06 | 1992-12-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-12-06 | 1996-06-06 | 1996-12-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-12-06 | 2000-06-06 | 2000-12-06 | $7700.00 | Window Closed / Lapsed |