EP0158265A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Benzamide and anilide derivatives
Assignee: Beecham Group PLC
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Filing: 1985-04-02
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Granted: —
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Expires: 2005-04-02
Abstract
Abstract Compounds of formula (I), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of either of the foregoing: wherein one of X and Y is CO and the other is NH; p and q each independently are 0 to 2; R 1 , R 2 and R 3 are each independently hydrogen, C 1-6 alkyl, hydroxy, C 1-6 alkoxy, C 1-6 alkylthio or halo; or any two on adjacent carbon atoms together are C 1-2 alkylenedioxy and the third is hydrogen, C 1-6 alkyl, C 1-6 alkoxy or halo; and R 4 is C 1-7 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl-C 1-2 alkyl, or a group (CH 2 ) t R 5 where t is 1 or 2 and R s is thienyl or furyl optionally substituted by one or two substituents selected from C 1-6 alkyl, C 1-6 alkoxy, trifluoromethyl or halogen, or is 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, having 5-HT antagonist activity, a process for their preparation and their use as pharmaceuticals.
Inventors
- 👤 Gordon Wootton
- 👤 Gareth John Sanger
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-02 13:21
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02; C07D451/04
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
195 words
A compound of formula (I), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of either of the foregoing: wherein one of X and Y is CO and the other is NH; p and q each independently are 0 to 2; R l , R2 and R3 are each independently hydrogen, C 1-6 alkyl, hydroxy, C 1-6 alkoxy, Cl-6 alkylthio or halo; or any two on adjacent carbon atoms together are C I - 2 alkylenedioxy and the third is hydrogen, C l - 6 alkyl, C l - 6 alkoxy or halo; and R 4 is C 1-7 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl-C 1-2 alkyl, or a group (CH 2 ) t R 5 where t is 1 or 2 and R5 is thienyl or furyl optionally substituted by one or two substituents selected from C l - 6 alkyl, C 1-6 alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C 1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C l - 4 alkyl optionally substituted by hydroxy, C l - 4 alkoxy, carboxy, esterified carboxy or in vivo hydrolysable acyloxy.
Claim 2
Dependent Claim
195 words
A compound of formula (I), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of either of the foregoing: wherein one of X and Y is CO and the other is NH; p and q each independently are 0 to 2; R l , R2 and R3 are each independently hydrogen, C 1-6 alkyl, hydroxy, C 1-6 alkoxy, Cl-6 alkylthio or halo; or any two on adjacent carbon atoms together are C I - 2 alkylenedioxy and the third is hydrogen, C l - 6 alkyl, C l - 6 alkoxy or halo; and R 4 is C 1-7 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl-C 1-2 alkyl, or a group (CH 2 ) t R 5 where t is 1 or 2 and R5 is thienyl or furyl optionally substituted by one or two substituents selected from C l - 6 alkyl, C 1-6 alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C 1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C l - 4 alkyl optionally substituted by hydroxy, C l - 4 alkoxy, carboxy, esterified carboxy or in vivo hydrolysable acyloxy.
Claim 3
Dependent Claim
14 words
A compound according to claim 1 wherein X is CO and Y is NH.
Claim 4
Dependent Claim
17 words
A compound according to claim 1 or 2 wherein p and q are independently O or 1.
Claim 5
Dependent Claim
23 words
A compound according to claim 1,2 or 3 wherein the group Y and the heterobicycle nitrogen atom are separated by 3 carbon atoms.
Claim 6
Dependent Claim
48 words
A compound according to claim 1 of formula (II) wherein R 1 1 is halo or C l - 6 alkoxy; R 2 1 is hydrogen or C 1-6 alkoxy; R 3 1 is halo or C 1-6 alkoxy; and R 4 is as defined in claim 1.
Claim 7
Dependent Claim
27 words
A compound according to claim 5 wherein R 1 1 is chloro, R 2 1 is hydrogen or chloro and R 3 1 is hydrogen or chloro.
Claim 8
Dependent Claim
15 words
A compound according to-any one of claims 1 to 6 wherein R4 is Cl-7 alkyl.
Claim 9
Dependent Claim
16 words
. 3,,5-Dichloro-N-[3p-(8-(2,2-dimethylpropyl) -8-azabicyclo (3.2.1)octyl)]benzamide, 3,5-dichloro-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide, 3, 5-dichloro-N-[3β-(8-benzyl-8-azabicyclo (3.2.1)octyl)]benzamide, 3,5-trimethoxy-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide, 3,4-dichloro-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide or 3,4-dichloro-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide.
Claim 10
Dependent Claim
16 words
. 3,,5-Dichloro-N-[3p-(8-(2,2-dimethylpropyl) -8-azabicyclo (3.2.1)octyl)]benzamide, 3,5-dichloro-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide, 3, 5-dichloro-N-[3β-(8-benzyl-8-azabicyclo (3.2.1)octyl)]benzamide, 3,5-trimethoxy-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide, 3,4-dichloro-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide or 3,4-dichloro-N-[3β-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide.
Claim 11
Dependent Claim
2 words
3,5-Dichloro-N-[3α-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide.
Claim 12
Dependent Claim
2 words
3,5-Dichloro-N-[3α-(8-methyl-8-azabicyclo (3.2.1)octyl)]benzamide.
Claim 13
Dependent Claim
114 words
A process for the preparation of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate of any of the foregoing, which process comprises reacting a compound of formula (III): with a compound of formula (IV): wherein one of G and L is COOl where Q 1 is a group displaceable by a nucleophile, and the other is NH 2 ; and thereafter optionally converting any R l , R 2 , R 3 or R 4 group to another R 1 , R 2 , R 3 or R 4 group respectively, and optionally forming a pharmaceutically acceptable salt of the resultant compound of formula (I).
Claim 14
Dependent Claim
26 words
A pharmaceutical composition comprising a compound according to any one of claims 1 to 9 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
24 words
A compound according to any one of claims 1 to 9 or a pharmaceutically acceptable salt thereof for use as an active therapeutic substance.
Claim 16
Dependent Claim
24 words
A compound according to any one of claims 1 to 9 for use in the treatment of migraine, cluster headache, trigerminal neuralgia and/or emesis.
References Cited (Backward Citations)
No citation records indexed.
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