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Details for Patent: 5,034,398

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Details for Patent: 5,034,398

Title: 1H-indazole-3-carboxamide-N-2-azabicyclo[2.2.2]octanes useful for treating anxiety, psychosis, neuralgia, migraine and cluster headaches
Abstract:Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein X is CO and Y is NH or O, or X is NH and Y is CO; Z is CH.sub.2, O, S or NR.sub.3 wherein R.sub.3 is hydrogen, C.sub.1-6 alkyl, C.sub.3-7 alkenyl-methyl, phenyl or phenyl C.sub.1-4 alkyl either of which phenyl moieties may be substituted by one or two of halogen, CF.sub.3, C.sub.1-6 alkoxy or C.sub.1-6 alkyl; and R.sub.a is not present; or Z is CH or N and R.sub.a is as defined for R.sub.3 above; R.sub.b is present when X--Y--R.sub.2 is attached at the phenyl ring and is selected from hydrogen, halogen, CF.sub.3, hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl; R.sub.1 is hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-7 acyl, C.sub.1-7 acylamino, C.sub.1-6 alkylsulphonylamino, N-(C.sub.1-6 alkylsulphonyl)-N-C.sub.1-4 alkylamino, C.sub.1-6 alkylsulphinyl, hydroxy, nitro or amino, aminocarbonyl, aminosulphonyl, aminosulphonylamino or N-(aminosulphonyl)-C.sub.1-4 alkylamino optionally N-substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl C.sub.1-4 alkyl, phenyl or phenyl C.sub.1-4 alkyl groups or optionally N-disubstituted by C.sub.4-5 polymethylene; R.sub.2 is a group of formula (a), (b) or (c) ##STR2## wherein n is 2 or 3; p and q are independently 1 to 3; and R.sub.4 or R.sub.5 is C.sub.1-7 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-2 alkyl, or a group (CH.sub.2).sub.t R.sub.6 where t is 1 or 2 and R.sub.6 is thienyl, pyrrolyl or furyl optionally substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C.sub.1-4 alkyl optionally substituted by hydroxy, C.sub.1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolysable acyloxy, having 5-HT antagonist activity and/or gastric motility enhancing activity, a process for their preparation and their use as pharmaceuticals.
Inventor(s): King; Francis D. (Bishop's Stortford, GB2)
Assignee: Beecham Group p.l.c. (Middlesex, GB)
Filing Date:Oct 03, 1989
Application Number:07/416,501
Claims:1. A compound of formula (I), or a pharmaceutically acceptable salt thereof: ##STR23## wherein X is CO and Y is NH;

Z is NR.sub.3 wherein R.sub.3 is hydrogen, C.sub.1-6 alkyl, C.sub.3-7 alkenyl-methyl, phenyl or phenyl C.sub.1-4 alkyl either of which phenyl moieties may be substituted by one or two of halogen, CF.sub.3, C.sub.1-6 alkoxy or C.sub.1-6 alkyl;

R.sub.b is present when X--Y--R.sub.2 is attached at the phenyl ring and is selected from hydrogen, halogen, CF.sub.3, hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl;

R.sub.1 is hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-7 acyl, C.sub.1-7 acylamino, C.sub.1-6 alkylsulphonylamino, N-(C.sub.1-6 alkylsulphonyl)-N-C.sub.1-4 alkylamino, C.sub.1-6 alkylsulphinyl, hydroxy, nitro, amino, aminocarbonyl, aminosulphonyl, aminosulphonylamino or N-(aminosulphonyl)-C.sub.1-4 alkylamino optionally N-substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl C.sub.1-4 alkyl, phenyl or phenyl C.sub.1-4 alkyl groups or optionally N-disubstituted by C.sub.4-5 polymethylene;

R.sub.2 is a group of formula (c) ##STR24## wherein q is 2; and R.sub.5 is C.sub.1-7 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-2 alkyl, or a group (CH.sub.2).sub.t R.sub.6 where t is 1 or 2 and R.sub.6 is thienyl, pyrrolyl or furyl optionally substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, C.sub.1-4 alkoxycarbonyl, phenoxycarbonyl or benzyloxycarbonyl optionally substituted in the phenyl ring by one or two substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, halogen or nitro, and C.sub.1-4 alkyl optionally substituted by hydroxy, C.sub.1-4 alkoxy, carboxy, C.sub.1-4 alkoxycarbonyl, phenoxycarbonyl or benzyloxycarbonyl optionally substituted in the phenyl ring by one or two substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, halogen or nitro, or C.sub.1-6 alkanoyloxy, benzoyloxy or benzenesulphonyloxy either being optionally substituted in the phenyl ring by one or two substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro or sulphonyloxy.

2. A compound according to claim 1 wherein the X--Y--R.sub.2 side chain is attached at position 3, as depicted in formula (I) in claim 1.

3. A compound according to claim 1 wherein R.sub.1 is hydrogen or 5-halo.

4. A compound according to claim 1 wherein R.sub.5 is C.sub.1-7 alkyl.

5. A compound according to claim 4 wherein R.sub.5 is methyl.

6. A compound according to claim 1 wherein Y--R.sub.2 is in the endo configuration.

7. 5.alpha.-N-( 2-Methyl-2-azabicyclo[2.2.2]oct-5-yl)-1-methylindazole-3-carboxamide or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition for the treatment of migraine or cluster headache, comprising an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

9. A pharmaceutical composition for the treatment of trigeminal neuralgia, comprising an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

10. A pharmaceutical composition for the treatment of emesis, comprising an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

11. A pharmaceutical composition for the treatment of anxiety, comprising an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

12. A pharmaceutical composition for the treatment of psychosis, comprising an effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

13. A method of treatment or prophylaxis of migraine or cluster headache in mammals, which comprises administration to a mammal in need of such treatment an effective amount of a compound according to claim 1.

14. A method of treatment or prophylaxis of trigeminal neuralgia in mammals, which comprises administration to a mammal in need of such treatment an effective amount of a compound according to claim 1.

15. A method of treatment or prophylaxis of emesis in mammals, which comprises administration to a mammal in need of such treatment an effective amount of a compound according to claim 1.

16. A method of treatment or prophylaxis of anxiety in mammals, which comprises administration to a mammal in need of such treatment an effective amount of a compound according to claim 1.

17. A method of treatment or prophylaxis of psychosis in mammals, which comprises administration to a mammal in need of such treatment an effective amount of a compound according to claim 1.
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