US4459300A
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Pharmaceutically active aza-bicyclo benzamide derivatives
Assignee: Beecham Group PLC
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Filing: 1982-06-17
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Granted: 1984-07-10
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Expires: 2002-06-17
Abstract
Abstract Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: n, p and q independently are 0 to 2; R 5 is hydrogen or C 1-6 alkyl; R 6 is C 1-7 alkyl or a group --(CH 2 ) s R 7 where s is 0 to 2 and R 7 is a C 3-8 cycloalkyl group, or a group --(CH 2 ) t R 8 where t is 1 or 2 and R 8 is C 2-5 alkenyl or a phenyl group optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-4 alkoxy, trifluoromethyl and halogen, or a thienyl group; R 12 is C 1-6 alkylsulphonyl; and either R 1 is C 1-6 alkoxy or C 1-6 alkylthio; and one of R 2 and R 11 is hydrogen and the other is C 1-6 alkoxy, C 1-6 alkyl or hydroxy; or R 1 and R 2 together are C 1-3 alkylenedioxy; and R 11 is hydrogen, halogen, CF 3 , C 1-6 alkoxy, hydroxy, nitro, C 1-7 acyl, amino, C 1-7 acylamino, aminocarbonyl optionally substituted by one or two C 1-6 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl C 1-4 alkyl, phenyl or phenyl C 1-4 alkyl groups any of which phenyl moieties may be substituted by one or more halogen, trifluoromethyl, C 1-6 alkoxy or nitro groups or N-disubstituted by C 4-6 polymethylene, having useful pharmacological activity, e.g. in the treatment of impaired gastric motility, a process for their preparation and their use.
Inventors
- 👤 Eric A. Watts
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:07
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02; C07D451/04; A; A61; A61P; A61P1/00; A61P1/08; A61P1/14; A61P43/00; C07D319/00; C07D319/10; C07D319/14; C07D319/16; C07D319/18; C07D451/14
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
228 words
A compound of formula (I) and pharmaceutically acceptable salts thereof: ##STR50## wherein: n, p and q independently are 0 to 2; R 5 is hydrogen or C 1-6 alkyl; R 6 is C 1-7 alkyl or a group --(CH 2 ) s R 7 where s is 0 to 2 and R 7 is a C 3-8 cycloalkyl group, or a group --(CH 2 ) t R 8 where t is 1 or 2 and R 8 is C 2-5 alkenyl or a phenyl group optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-4 alkoxy, trifluoromethyl and halogen, or a thienyl group; R 12 is C 1-6 alkylsulphonyl; and either R 1 is C 1-6 alkoxy or C 1-6 alkylthio; and one of R 2 and R 11 is hydrogen and the other is C 1-6 alkoxy, or hydroxy; or R 1 and R 2 together are C 1-3 alkylenedioxy; and R 11 is hydrogen, halogen, CF 3 , C 1-6 alkoxy, hydroxy, nitro, C 1-7 acyl, amino, C 1-7 acylamino, aminocarbonyl optionally substituted by one or two C 1-6 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl C 1-4 alkyl, phenyl or phenyl C 1-4 alkyl groups any of which phenyl moieties may be substituted by one or more halogen, trifluoromethyl, C 1-6 alkoxy or nitro groups or N-disubstituted by C 4-6 polymethylene.
Claim 2
Dependent Claim
228 words
A compound of formula (I) and pharmaceutically acceptable salts thereof: ##STR50## wherein: n, p and q independently are 0 to 2; R 5 is hydrogen or C 1-6 alkyl; R 6 is C 1-7 alkyl or a group --(CH 2 ) s R 7 where s is 0 to 2 and R 7 is a C 3-8 cycloalkyl group, or a group --(CH 2 ) t R 8 where t is 1 or 2 and R 8 is C 2-5 alkenyl or a phenyl group optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-4 alkoxy, trifluoromethyl and halogen, or a thienyl group; R 12 is C 1-6 alkylsulphonyl; and either R 1 is C 1-6 alkoxy or C 1-6 alkylthio; and one of R 2 and R 11 is hydrogen and the other is C 1-6 alkoxy, or hydroxy; or R 1 and R 2 together are C 1-3 alkylenedioxy; and R 11 is hydrogen, halogen, CF 3 , C 1-6 alkoxy, hydroxy, nitro, C 1-7 acyl, amino, C 1-7 acylamino, aminocarbonyl optionally substituted by one or two C 1-6 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl C 1-4 alkyl, phenyl or phenyl C 1-4 alkyl groups any of which phenyl moieties may be substituted by one or more halogen, trifluoromethyl, C 1-6 alkoxy or nitro groups or N-disubstituted by C 4-6 polymethylene.
Claim 3
Dependent Claim
45 words
A compound according to claim 1 of formula (II): ##STR51## wherein: R 1 1 is C 1-6 alkoxy; R 14 is C 1-6 alkyl; R 15 is C 1-6 alkoxy, or hydroxy; and R 6 , p and q are as defined in claim 1.
Claim 4
Dependent Claim
49 words
A compound according to claim 2 of formula (IV): ##STR52## wherein: R 6 2 is C 5-7 alkyl; a group --(CH 2 ) t R 8 1 wherein t is 1 or 2 and R 8 1 is optionally substituted phenyl as defined in claim 1; cyclohexylmethyl, or 2-thienylmethyl.
Claim 5
Dependent Claim
17 words
A compound according to claim 2 wherein R 1 1 is methoxy and R 15 is methoxy.
Claim 6
Dependent Claim
11 words
A compound according to claim 2 wherein R 14 is methyl.
Claim 7
Dependent Claim
12 words
A compound according to claim 3 wherein R 6 2 is benzyl.
Claim 8
Dependent Claim
4 words
2,3-Ethylenedioxy-5-methylsulphonyl N-[3,β-(8-benzyl-8-azabicyclo[3.2.1]octyl]benzamide or 2,4-Dimethoxy-5-methylsulphonyl-N[3]-(8-benzyl-8-azabicyclo[3.2.1]octyl)benzamide.
Claim 9
Dependent Claim
4 words
2,3-Ethylenedioxy-5-methylsulphonyl N-[3,β-(8-benzyl-8-azabicyclo[3.2.1]octyl]benzamide or 2,4-Dimethoxy-5-methylsulphonyl-N[3]-(8-benzyl-8-azabicyclo[3.2.1]octyl)benzamide.
Claim 10
Dependent Claim
17 words
A compound according to claim 3, wherein R 1 1 is methoxy and R 15 is methoxy.
Claim 11
Dependent Claim
11 words
A compound according to claim 1, wherein R 12 is methylsulphonyl.
Claim 12
Dependent Claim
11 words
A compound according to claim 3, wherein R 14 is methyl.
Claim 13
Dependent Claim
102 words
A compound of the formula (XII): ##STR53## wherein R 6 is C 1-7 alkyl or a group --(CH 2 ) s R 7 where s is 0 to 2 and R 7 is a C 3-8 cycloalkyl group, or a group --(CH 2 ) t R 8 where t is 1 or 2 and R 8 is C 2-5 alkenyl or a phenyl group optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-4 alkoxy, trifluoromethyl and halogen, or a thienyl group; R 14 is C 1-6 alkyl; and p and q are independently 0, 1 or 2.
Claim 14
Dependent Claim
102 words
A compound of the formula (XII): ##STR53## wherein R 6 is C 1-7 alkyl or a group --(CH 2 ) s R 7 where s is 0 to 2 and R 7 is a C 3-8 cycloalkyl group, or a group --(CH 2 ) t R 8 where t is 1 or 2 and R 8 is C 2-5 alkenyl or a phenyl group optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-4 alkoxy, trifluoromethyl and halogen, or a thienyl group; R 14 is C 1-6 alkyl; and p and q are independently 0, 1 or 2.
Claim 15
Dependent Claim
56 words
A compound of the formula (XIV) ##STR54## wherein R 6 2 is C 5-7 alkyl; --(CH 2 ) t R 8 1 , wherein t is 1 or 2 and R 8 1 is phenyl optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-4 alkoxy, trifluoromethyl and halogen; cyclohexylmethyl; or 2-thienylmethyl.
Claim 16
Dependent Claim
56 words
A compound of the formula (XIV) ##STR54## wherein R 6 2 is C 5-7 alkyl; --(CH 2 ) t R 8 1 , wherein t is 1 or 2 and R 8 1 is phenyl optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-4 alkoxy, trifluoromethyl and halogen; cyclohexylmethyl; or 2-thienylmethyl.
Claim 17
Dependent Claim
11 words
A compound according to claim 11, wherein R 6 is benzyl.
Claim 18
Dependent Claim
12 words
A compound according to claim 12, wherein R 6 2 is benzyl.
Claim 19
Dependent Claim
11 words
A compound according to claim 11, wherein R 14 is methyl.
Claim 20
Dependent Claim
11 words
A compound according to claim 12, wherein R 14 is methyl.
Claim 21
Dependent Claim
51 words
A pharmaceutical composition for the treatment of impaired gastric motility and/or for treatment of disorders of the central nervous system comprising an amount effective to improve gastric motility or an antipsychotic effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Claim 22
Dependent Claim
37 words
A method of treating impaired gastric motility in mammals including humans comprising the administration to the sufferer of an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof to the sufferer.
Claim 23
Dependent Claim
38 words
A method of treatment of disorders of the central nervous system in mammals including humans, comprising the administration to the sufferer of an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
EP0013138A1
Cited
US4273778A
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FR2446823A1
Cited
GB2042522A
Cited
FR2476088A2
Cited
EP0031219A1
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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) | 1987-07-10 | 1988-01-09 | 1988-07-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-10 | 1992-01-09 | 1992-07-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-10 | 1996-01-09 | 1996-07-10 | $7700.00 | Window Closed / Lapsed |