Amide derivatives as 5-HT.sub.1A ligands

Details Amide derivatives as 5-HT.sub.1A ligands Amide derivatives as 5-HT.sub.1A ligands

1995-05-25

1997-05-13

Springer, David B.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514352, 514338, 514339, 546171, 5462774, 5462024, 546330, 546336, 546338, 546342, 546329, 546339, 546346, 546348, C07D40112, C07D21375, C07D40712, A61K 3147, A61K 3144

Patent

active

056293232

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/61394/00455 filed Mar. 9, 1994.
This invention relates to novel amide derivatives, to processes for their preparation, to their use and to pharmaceutical compositions containing them. The novel compounds act on the central nervous system by binding to 5-HT receptors (as more fully explained below) and hence can be used as medicaments for treating humans and other mammals.
The novel compounds of the invention are those of general formula (I) ##STR2## and the pharmaceutically acceptable salts thereof.
In formula (I) ##STR3## where X is --(CH.sub.2).sub.n --, --OCH.sub.2 -- or --SCH.sub.2 --, m is 0 or 1, n is 1, 2 or 3 and p is 0 or 1 such that (m+p) is 1 and that (m+n) is 1, 2 or 3, trifluoromethyl, (lower)alkoxycarbonyl, carboxamido, nitro, cyano, amino, (lower)alkylamino, di(lower)alkylamino or (lower) alkylcarbonyl, R.sup.6' is hydrogen when X is --OCH.sub.2 -- or --SCH.sub.2 --, ##STR4## where Y is --O--, --S-- or --CH.sub.2 --, Z represents a heteroaromatic ring fused on to the non-aromatic ring containing the Y group attached to the heteroaromatic ring and/or the non-aromatic ring or ##STR5## where R.sup.6 is as defined above and the indicated 7, 8 positions may optionally be fused with a heteroaromatic ring or a further aromatic ring or
The term "lower" as used herein means that the radical referred to contains 1 to 6 carbon atoms. Preferably such radicals contain 1 to 4 carbon atoms. Examples of "lower alkyl" radicals are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl and isopentyl.
Examples of cycloalkyl groups are groups containing 3 to 8 carbon atoms e.g. cyclopentyl, cyclohexyl and cycloheptyl.
When used herein "aryl" means an aromatic radical having 6 to 12 carbon atoms (e.g. phenyl or naphthyl) which optionally may be substituted by one or more substituents. Preferred substituents are lower alkyl, lower alkoxy (e.g. methoxy, ethoxy, propoxy, butoxy), halogen (e.g. chlorine), halo(lower)alkyl (e.g. trifluoromethyl), nitro, nitrile, amido, (lower)alkoxycarbonyl, amino, (lower)alkylamino and di(lower)alkylamino.
The term "heteroaryl" refers to an aromatic radical containing one or more (e.g. 1, 2 or 3) hetero ring atoms (e.g. oxygen, nitrogen, sulphur) and which may be optionally substituted by one or more substituents. Examples of suitable substituents are given above in connection with "aryl" radicals. The heteroaryl radical may, for example, contain 5 to 10 ring atom. Unless specified otherwise the heteroaryl radical is preferably mono- or bicyclic. A monocyclic radical may, for example, contain 5 to 7 ring atoms. Preferably the hetero ring contains a nitrogen atom with or without one or more further hetero atoms. Examples of heteroaryl groups include, for example, pyridinyl, pyfimidinyl, pyrazinyl, quinolinyl, isoquinolinyl and indolyl each of which may be optionally substituted as mentioned above.
When a "heteroaromatic ring" is fused on to a non-aromatic ring (as in formula B) or is fused on to an aromatic ring (as in formula D) the "heteroaromatic ring" may be a fused "heteroaryl" group where heteroaryl is defined above.
Examples of the preferred meanings of the various substituents in formula (I) are given below: ##STR6## where R.sup.6 is as defined above, particularly lower alkoxy, B is preferably a group of formula: ##STR7## where R.sup.6 is as defined above, C is preferably a group of formula ##STR8## where R.sup.6 is as defined above, particularly lower alkoxy, D is preferably a group of formula ##STR9## E is preferably a group of formula ##STR10## where R.sup.6 is as defined above, F is preferably a group of formula ##STR11## The compounds of the invention may be prepared by methods known in the art from known starting materials or starting materials that may be prepared by conventional methods.
One method of preparing the compounds of the invention comprises the reductive amination of a compound of formula formula ##STR12## (where R.sup.1, R.sup.2, R.sup.3 and R.sup.3' are as defined above) eg by reacting the compounds of formu

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