EP0068700A1
Expired / Lapsed
EP
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Azobicycloalkylbenzamides, process for their preparation and pharmaceutical compositions containing them
Assignee: Beecham Group PLC
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Filing: 1982-06-14
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Granted: —
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Expires: 2002-06-14
Abstract
Abstract Compounds of formula [1], and pharmaceutically acceptable salts and solvent adducts and N-oxides thereof: wherein: n, p and q independently are 0 to 2; R s is hydrogen or C 1-6 alkyl; R, 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 3-7 cycloalkyl group, or a group (CH 2 ),R a where t is 1 or 2 and R, 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 aminosulphonyl optionally substituted by one or two C 1-6 alkyl or 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- disubstiuted by C 1-6 polymethylene; and either R, is C 1-6 alkoxy or C 1-6 alkylthio; and one of R 2 and R,, is hydrogen and the other is C 1-6 alkoxy, C 1-6 alkyl or hydroxy; or R, and R 2 together are C,. 3 alkylenedioxy; and R,, is hydrogen, halogen, CF 3 , C,. 6 alkyl, C 1-6 alkoxy, C 1-7 acyl, hydroxy, nitro, C 1-7 acylamino, amino or 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.
Inventors
- 👤 Eric Alfred Watts
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 23:00
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: 14
Claim 1
Independent Claim
292 words
A compound of formula (I)and pharmaceutically acceptable salts and solvent adducts and N-oxides thereof: 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 O 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 R8 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 aminosulphonyl optionally substituted by one or two C 1-6 alkyl or 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 on or more halogen, trifluoromethyl, C 1-6 alkoxy or nitro groups,or N- disubstituted by C 4-6 polymethylene; 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 alkyl, C 1-6 alkox y, C 1-7 acyl, hydroxy, nitro, C l-7 acylamino, amino or 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
292 words
A compound of formula (I)and pharmaceutically acceptable salts and solvent adducts and N-oxides thereof: 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 O 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 R8 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 aminosulphonyl optionally substituted by one or two C 1-6 alkyl or 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 on or more halogen, trifluoromethyl, C 1-6 alkoxy or nitro groups,or N- disubstituted by C 4-6 polymethylene; 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 alkyl, C 1-6 alkox y, C 1-7 acyl, hydroxy, nitro, C l-7 acylamino, amino or 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
58 words
A compound according to claim 1 of formula (II): wherein: R i is C 1-6 alkoxy; R 14 is hydrogen, C 1-6 alkyl or C 3-8 cycloalkyl; R 15 is hydrogen or C 1-6 alkyl; R16 is C 1-6 alkoxy, C 1-6 alkyl or hydroxy; and R 6 , p and q are as defined in claim 1.
Claim 4
Dependent Claim
59 words
A compound according to claim 1 or 2 of formula (IV): wherein: R 2 6 is C 5-7 alkyl; a group -(CH 2 ) t R1 8 wherein t is 1 or 2 and R 1 8 is optionally substituted phenyl as defined in claim 1; cyclohexylmethyl, or 2-thienylmethyl; and the remaining variables are as- defined in claim 1.
Claim 5
Dependent Claim
19 words
A compound according to claim 2 or 3 wherein R 1 1 is methoxy and R 16 is methoxy.
Claim 6
Dependent Claim
19 words
A compound according to claim 1 of formula (XII): wherein the variable groups are as defined in claim 1.
Claim 7
Dependent Claim
19 words
A compound according to claim 5 of formula (XIV): wherein the variable groups are as defined in claim 3.
Claim 8
Dependent Claim
23 words
A compound according to any one of the claims 1 to 6 wherein R 14 and R 15 are independently hydrogen or methyl.
Claim 9
Dependent Claim
18 words
A compound according to any one of the claims 3 to 7 wherein R 2 6 is benzyl.
Claim 10
Dependent Claim
3 words
2,3-Ethylenedioxy-5-methylaminosulphonyl-N(3β-(8-benzyl-8-azabicyclo[3.2.1]octyl)]benzamide or 2,3-dimethoxy-5-dimethylaminosulphonyl-N(3β(8-benzyl-8-azabicylo[3.2.1]octyl(]benzamide.
Claim 11
Dependent Claim
3 words
2,3-Ethylenedioxy-5-methylaminosulphonyl-N(3β-(8-benzyl-8-azabicyclo[3.2.1]octyl)]benzamide or 2,3-dimethoxy-5-dimethylaminosulphonyl-N(3β(8-benzyl-8-azabicylo[3.2.1]octyl(]benzamide.
Claim 12
Dependent Claim
90 words
A process for the preparation of a compound of formula (I) which process comprises reacting a compound of formula (XIX): with a compound of formula (XX): wherein Q is a leaving group and the remaining variable groups being as defined in claim 1; and thereafter if necessary converting a group R 11 or R 12 in the thus formed compound to another group R 11 or R 12 respectively; converting R 6 to another R6; and optionally forming a pharmaceutically acceptable salt of the resultant compound of the formula (I).
Claim 13
Dependent Claim
31 words
A pharmaceutical composition comprising a compound according to any one of the claims 1 to 9 or a pharmaceutically acceptable salt, solvent adduct or N-oxide thereof and a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
22 words
A compound according to any one of the claims 1 to 9 for use in treating disorders related to impaired gastric motility.
References Cited (Backward Citations)
EP0013138A1
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FR2446823A1
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GB2042522A
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FR2476088A2
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EP0031219A1
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EP0042705A1
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