Azabicyclic derivatives
AssigneeJohn Wyeth & Brother Limited
InventorIan A. Cliffe
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Abstract
Azabicyclic compounds of formula ##STR1## and their pharmaceutically acceptable acid addition salts are disclosed. In the formula, ##STR2## is an optionally substituted heteroaryl group containing at least one hetero atom X; n is 2, 3 or 4; m is 1 or 2; R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.3-5 -alkenyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-C.sub.1-2 alkyl or aryl- or heteroaryl-C.sub.1-2 -alkyl; and the --(CH.sub.2).sub.m ##STR3## moiety is ortho to the hetero atom X. The compounds exhibit activity as 5-HT.sub.3 -antagonists and can be used, inter alia, for the treatment of neuropsychiatric disorders.
Claims8
An azabicyclic compound of formula ##STR15## or a pharmaceutically acceptable acid addition salt thereof, wherein ##STR16## represents an N-heteroaryl group containing 5 to 12 ring atoms and 0-2 other heteroatoms selected from the group consisting of N, O and S, optionally substituted by one or more C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino, C.sub.1-4 alkylamino, di(C.sub.1-4 -alkyl)amino, halogen, trifluoromethyl, phenyl, halophenyl, C.sub.1-4 -alkylphenyl, C.sub.1-4 -alkoxyphenyl, carboxy, carb oxamido, nitro, thiol, C.sub.1-4 -alkylthio or C.sub.1-4 -alkoxycarbonyl substituents;
- n represents 2, 3 or 4;
- m represents 1 or 2;
- R.sup.1 is hydrogen, C.sub.1-6 -alkyl, C.sub.3-5 -alkenyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 alkyl or aryl- or heteroaryl-C.sub.1-2 -alkyl, where the aryl group is a phenyl or napthyl radical optionally substituted by one or more halogen, C.sub.1-4 -alkoxy or C.sub.1-4 -alkyl groups and the heteroaryl group is a mono- or bicyclic heteroaryl radical containing 5 to 12 ring atoms and one or two hetero atoms selected from oxygen, nitrogen and sulphur, and ##STR17## moiety is ortho to the hetero atom X.
A process for preparing an azabicyclic compound of formula ##STR20## or a pharmaceutically acceptable acid addition salt thereof, wherein ##STR21## represents an N-heteroaryl group containing 5 to 12 ring atoms and 0-2 other heteroatoms selected from the group consisting of N, O and S, optionally substituted by one or more C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino, C.sub.1-4 alkylamino, di(C.sub.1-4 -alkyl)amino, halogen, trifluoromethyl, phenyl, halophenyl, C.sub.1-4 -alkylphenyl, C.sub.1-4 -alkoxyphenyl, carboxy, carb oxamido, nitro, thiol, C.sub.1-4 -alkylthio or C.sub.1-4 -alkoxycarbonyl substituents;
- n represents 2, 3 or 4;
- m represents 1 or 2;
- R.sup.1 is hydrogen, C.sub.1-6 -alkyl, C.sub.3-5 -alkenyl, C.sub.3-6 -cycloalkyl, C.sub.3-6 -cycloalkyl-C.sub.1-2 alkyl or aryl- or heteroaryl-C.sub.1-2 -alkyl, where the aryl group is a phenyl or napthyl radical optionally substituted by one or more halogen, C.sub.1-4 -alkoxy or C.sub.1-4 -alkyl groups and the heteroaryl group is a mono- or bicyclic heteroaryl radical containing 5 to 12 ring atoms and one or two hetero atoms selected from oxygen, nitrogen and sulphur;
- and ##STR22## moiety is ortho to the hetero atom N, which process comprises dehydrating a compound of formula ##STR23## or an acid addition salt thereof, wherein m, n, ##STR24## and R.sup.1 are as defined above.
Dependencies are inferred from the claim text.