EP0212802A1
Expired / Lapsed
EP
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Substituted benzamides
Assignee: Beecham Group PLC
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Filing: 1986-06-24
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Granted: —
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Expires: 2006-06-24
Abstract
Abstract Compounds of formula (I) or a pharmaceutically acceptable salt thereof: wherein: R 1 is C 1-6 alkyl; R 2 is amino or C 1-7 acylamino; R 3 is halo or C 1-6 alkylthio; R 4 and R 5 are independently selected from hydrogen, C 1-6 alkyl, phenyl or phenyl C 1-4 alkyl any of which phenyl moieties may be substituted by one or two of halo, CF 3 , C 1-6 alkoxy or C 1-6 alkyl; R 6 is C 1-7 alkyl, -(CH 2 ) s R 7 , s being 0 to 2 and R 7 being C 3-8 cycloalkyl, -(CH 2 ) t R B , t being 1 or 2 and R 8 being thienyl or phenyl optionally substituted by one or two substituents selected from C 1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy and C 1-4 alkyl optionally substituted by hydroxy, C 1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolysable acyloxy; and n is 0 to 3; having gashic motility enhancing activity and anti-emetic activity, a process for their preparation and their use as pharmaceuticals.
Inventors
- 👤 Francis David Beecham Pharmaceuticals King
- 👤 Michael Stewart Beecham Pharmaceuticals Hadley
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-28 03:51
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/22; A; A61; A61P; A61P1/00; A61P1/08; A61P1/14; A61P43/00; C07D221/24
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
169 words
A compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein: R 1 is C 1-6 alkyl; R 2 is amino or C 1-7 acylamino; R 3 is halo or C l - 6 alkylthio; R 4 and R 5 are independently selected from hydrogen, C 1-6 -alkyl, phenyl or phenyl C 1-4 alkyl any of which phenyl moieties may be substituted by one or two of halo, CF 3 , C l - 6 alkoxy or C 1-6 alkyl; R 6 is C 1-7 alkyl, -(CH 2 ) s R 7 , s being 0 to 2 and R 7 being C 3 - 8 cycloalkyl, -(CH 2 ) t R 8 , t being 1 or 2 and Rg being thienyl or phenyl optionally substituted by one or two substituents selected from C 1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy and C 1-4 alkyl optionally substituted by hydroxy, C 1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolysable acyloxy; and n is 0 to 3.
Claim 2
Dependent Claim
169 words
A compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein: R 1 is C 1-6 alkyl; R 2 is amino or C 1-7 acylamino; R 3 is halo or C l - 6 alkylthio; R 4 and R 5 are independently selected from hydrogen, C 1-6 -alkyl, phenyl or phenyl C 1-4 alkyl any of which phenyl moieties may be substituted by one or two of halo, CF 3 , C l - 6 alkoxy or C 1-6 alkyl; R 6 is C 1-7 alkyl, -(CH 2 ) s R 7 , s being 0 to 2 and R 7 being C 3 - 8 cycloalkyl, -(CH 2 ) t R 8 , t being 1 or 2 and Rg being thienyl or phenyl optionally substituted by one or two substituents selected from C 1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy and C 1-4 alkyl optionally substituted by hydroxy, C 1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolysable acyloxy; and n is 0 to 3.
Claim 3
Dependent Claim
11 words
A compound according to claim 1 wherein R 1 is methyl.
Claim 4
Dependent Claim
14 words
A compound according to claim 1 or 2 wherein Rg is amino or acetylamino.
Claim 5
Dependent Claim
16 words
A compound according to claim 1, 2 or 3 wherein R 3 is chloro or bromo.
Claim 6
Dependent Claim
43 words
A compound according to claim 1 of formula (II): wherein Rg is hydrogen or acetyl; R 4 1 is hydrogen or C l - 6 alkyl; R 6 1 is C l - 7 alkyl; and n is as defined in claim 1.
Claim 7
Dependent Claim
12 words
(±) (8p)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-azabicyclo[3,2,1]octan-8-yl)benzamide, ±) (8a)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-azabicyclo[3,2,1]octan-8-yl)benzamide, (±)(10α)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-aza-bicyclo[4,3,1]decan-10-yl)benzamide, (±)(8α)-4-amino-5-chloro-2-methoxy-N-(3-ethyl-3-aza-bicyclo[3,2,1]octan-8-yl)benzamide, (±)(8β)-4-amino-5-chloro-2-methoxy-N-(3-ethyl-3-aza-bicyclo[3,2,1]octan-8-yl)benzamide, (±)(8β)-4-amino-5-chloro-2-methoxy-N-(3-benzyl -3-aza-bicyclo[3,2,1]octan-8-yl)benzamide, (±)(9β)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-aza-bicyclo[3,3,1]nonan-9-yl)benzamide, or (±)(9α)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-aza-bicyclo[3,3,1]nonan-9-yl)benzamide,
Claim 8
Dependent Claim
12 words
(±) (8p)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-azabicyclo[3,2,1]octan-8-yl)benzamide, ±) (8a)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-azabicyclo[3,2,1]octan-8-yl)benzamide, (±)(10α)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-aza-bicyclo[4,3,1]decan-10-yl)benzamide, (±)(8α)-4-amino-5-chloro-2-methoxy-N-(3-ethyl-3-aza-bicyclo[3,2,1]octan-8-yl)benzamide, (±)(8β)-4-amino-5-chloro-2-methoxy-N-(3-ethyl-3-aza-bicyclo[3,2,1]octan-8-yl)benzamide, (±)(8β)-4-amino-5-chloro-2-methoxy-N-(3-benzyl -3-aza-bicyclo[3,2,1]octan-8-yl)benzamide, (±)(9β)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-aza-bicyclo[3,3,1]nonan-9-yl)benzamide, or (±)(9α)-4-amino-5-chloro-2-methoxy-N-(3-methyl-3-aza-bicyclo[3,3,1]nonan-9-yl)benzamide,
Claim 9
Dependent Claim
80 words
7 . A process for the preparation of a compound according to claim 1, or a pharmaceutically acceptable salt thereof which process comprises reacting a compound of formula (III): with a compound of formula (IV): wherein Q is a leaving group; R 10 is R 2 or nitro; and the remaining variables are as defined in claim 1, and thereafter optionally converting R 10 to R 2 , R 6 to other R 6 and/or forming a pharmaceutically acceptable salt.
Claim 10
Dependent Claim
67 words
A process for the preparation of a compound according to claim 1 which process comprises reacting a compound of formula (V): wherein the variable groups are as defined in claim 1, with Q 2 R 6 wherein Q 2 is a leaving group and R 6 is as defined in formula (I), and thereafter optionally forming a pharmaceutically acceptable salt of the resulting compound of formula (I).
Claim 11
Dependent Claim
10 words
A compound of formula (V) as defined in claim 8.
Claim 12
Dependent Claim
27 words
A pharmaceutical composition comprising a compound according to any one of claims 1 to 6 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
25 words
A compound according to any one of claims 1 to 6 for use in the treatment of disorders relating to impaired gastro-intestinal motility and/or emesis.
References Cited (Backward Citations)
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