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US4826838A
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Analgesic carbocyclic and heterocyclic carbonylmethylene-and carbonylmethypipidines and-pyrrolidines
Assignee: Sandoz AG
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Filing: 1987-07-07
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Granted: 1989-05-02
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Expires: 2007-07-07
Abstract
Abstract Carbocyclic and heterocyclic carbonylmethylene- and carbonylmethylpiperidines and -pyrrolidines are serotonin antagonists.
Inventors
- 👤 Brian P. Richardson
- 👤 Rudolf K. A. Giger
- 👤 Gunter Engel
- 👤 Roland Furler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:32
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
229 words
A compound of formula Ic: A--CO--B'" Ic wherein A is a group of formula II, ##STR23## wherein the free valence is attached to either fused 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; or a group of formula III, ##STR24## wherein R 4 to R 7 , independently, are hydrogen, amino, nitro, (C 1-4 )alkylamino, di(C 1-4 )alkylamino, halogen, (C 1-4 )alkoxy, (C 1-4 )alkyl, (C 1-4 )alkanoylamino or pyrrolyl; and B'" is one of the groups of formulae XII to XVIII, ##STR25## wherein n is 1, 2 or 3; Z is hydrogen or (C 1-4 )alkoxy; R 8 is hydrogen, (C 1-7 )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; R 9 is hydrogen or (C 1-4 )alkyl; m is 2 or 3; and the bond in the group of formula XVII is in position 3- or 4-; or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 2
Dependent Claim
229 words
A compound of formula Ic: A--CO--B'" Ic wherein A is a group of formula II, ##STR23## wherein the free valence is attached to either fused 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; or a group of formula III, ##STR24## wherein R 4 to R 7 , independently, are hydrogen, amino, nitro, (C 1-4 )alkylamino, di(C 1-4 )alkylamino, halogen, (C 1-4 )alkoxy, (C 1-4 )alkyl, (C 1-4 )alkanoylamino or pyrrolyl; and B'" is one of the groups of formulae XII to XVIII, ##STR25## wherein n is 1, 2 or 3; Z is hydrogen or (C 1-4 )alkoxy; R 8 is hydrogen, (C 1-7 )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; R 9 is hydrogen or (C 1-4 )alkyl; m is 2 or 3; and the bond in the group of formula XVII is in position 3- or 4-; or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 3
Dependent Claim
98 words
A compound of formula I: A--CO--B I wherein A is a group of formula II, ##STR26## wherein the free valence is attached to the 3-position; X is --NH-- or --S--; R 1 is hydrogen; R 2 is hydrogen or (C 1-4 )alkyl; and B is either a group of formula IV, ##STR27## wherein n is 1; Z is hydrogen; R 8 is (C 1-4 )alkyl; and X-Y is ##STR28## or a group of formula XII, ##STR29## wherein n, Z and R 8 are as defined above; or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 4
Dependent Claim
98 words
A compound of formula I: A--CO--B I wherein A is a group of formula II, ##STR26## wherein the free valence is attached to the 3-position; X is --NH-- or --S--; R 1 is hydrogen; R 2 is hydrogen or (C 1-4 )alkyl; and B is either a group of formula IV, ##STR27## wherein n is 1; Z is hydrogen; R 8 is (C 1-4 )alkyl; and X-Y is ##STR28## or a group of formula XII, ##STR29## wherein n, Z and R 8 are as defined above; or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 5
Dependent Claim
20 words
A compound of claim 2 which is indol-3-yl-carbonylmethylenyl-3-(8-methyl-8-azabicyclo[3.2.1]octane), or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 6
Dependent Claim
20 words
A compound of claim 2 which is 2-methyl-benzothiophen-3-yl-carbonyl-methylenyl-3-(8-methyl-8-azabicyclo[3.2.1]octane), or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 7
Dependent Claim
20 words
A compound of claim 2 which is indol-3-yl-carbonyl-methyl-3s-(8-methyl-8-azabicyclo[3.2.1]octane), or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 8
Dependent Claim
20 words
A compound of claim 2 which is indol-3-yl-carbonyl-methyl-3-(8-methyl-8-azabicyclo[3.2.1]oct-2,3-ene), or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 9
Dependent Claim
20 words
A compound of claim 2 which is 2-methyl-benzothiophen-3-yl-carbonyl-methyl-3s-(8-methyl-8-azabicyclo[3.2.1]octane), or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 10
Dependent Claim
20 words
A compound of claim 2 which is (+)-indol-3-yl-carbonylmethylenyl-3-(8-methyl-8-azabicyclo[3.2.1]octane), or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 11
Dependent Claim
20 words
A compound of claim 2 which is (-)indol-3-yl-carbonylmethylenyl-3-(8-methyl-8-azabicyclo[3.2.1]octane), or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 12
Dependent Claim
41 words
A pharmaceutical composition useful for treating algesia, arrhytmia and gastrointestinal disorders comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 13
Dependent Claim
41 words
A pharmaceutical composition useful for treating algesia, arrhythmia and gastrointestinal disorders comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 2, or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 14
Dependent Claim
37 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 salt or quaternary ammonium salt thereof.
Claim 15
Dependent Claim
37 words
A method for 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 salt or quaternary ammonium salt thereof.
Claim 16
Dependent Claim
38 words
A method of treating gastrointestinal 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 salt or quaternary ammonium salt thereof.
Claim 17
Dependent Claim
37 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 2, or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 18
Dependent Claim
37 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 2, or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
Claim 19
Dependent Claim
38 words
A method of treating gastrointestinal disorders comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 2, or a pharmaceutically acceptable acid addition salt or quaternary ammonium salt thereof.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1992-05-01 | 1992-10-31 | 1993-05-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-01 | 1996-10-31 | 1997-05-02 | $3760.00 | Window Closed / Lapsed |
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