Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-01-16
1998-06-09
Chang, Ceila
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514183, 514212, 514331, 514339, 514357, 514428, 540596, 540597, 540610, 544130, 544131, 544360, 544364, 546193, 546194, 546205, 546207, 546208, 546233, 5462777, 5462824, 5462681, 5462791, 546337, 548568, 548950, A61K 31445, A61K 3155, C07D40112, C07D40514
Patent
active
057634602
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB94/01501 filed Jul. 12, 1994. This invention relates to novel heterocyclic 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.
Von R. Hiltmann et al in Arzneim-Forsch. (Drug Res.), 1974, 24, 584-600 discloses certain 2-acylaminopyridine derivatives having morphine agonistic or antagonistic properties.
The novel compounds of the invention are those of general formula ##STR2## and the pharmaceutically acceptable acid addition salts thereof.
In formula I the ring, provided that a is at least 1, or more lower alkyl groups, is not an unsubstituted phenyl group,
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, tert.-butyl, pentyl and isopentyl.
A cycloalkyl or cycloalkenyl group can contain 3 to 12 (e.g. 3 to 8) carbon atoms. Preferably a cycloalkyl group is cyclopentyl, cyclohexyl or cycloheptyl, most preferably cyclohexyl. Preferably a cycloalkenyl group is cyclohex-3-enyl.
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 alkenyl, lower alkynyl, lower alkoxy (e.g. methoxy, ethoxy, propoxy, butoxy), hydroxy, halogen (e.g. chlorine), halo(lower)alkyl (e.g. trifluoromethyl), nitro, nitrile, carbamoyl, (lower)alkylcarbamoyl, di(lower)alkyl carbamoyl, (lower)alkylcarbonyl, (lower)alkoxycarbonyl, amino, (lower)alkylamino and di(lower)alkylamino.
Two substituents on the aromatic ring may be connected together to form another ring system. For example R may be a bicyclic oxygen-containing radical of the formula ##STR3## wherein R.sup.3 represents hydrogen or one or more same or different substituents selected from lower alkyl, halogen, hydroxy, (lower)alkoxy, hydroxy(lower)alkyl, (lower)alkoxy(lower alkyl), lower alkanoyloxy(lower alkyl), (lower)alkylcarbonyl, (lower)alkylcarbonyl-(lower)alkyl, (lower)alkylcarbonylamino, amino, (lower)alkylamino or di(lower)alkylamino and the heterocyclic ring containing the oxygen atom contains a total of 5 to 7 ring members, said heterocyclic ring being saturated or unsaturated, being optionally substituted (e.g. by one or more substituents R.sup.4 where R.sup.4 has the meaning given for R.sup.3 above) and optionally containing one or more hetero ring members (e.g. --O--, --S--, --SO.sub.2 -- or --NR.sup.5 -- where R.sup.5 is hydrogen or lower alkyl) in addition to the oxygen atom illustrated
A preferred example of such a bicyclic oxygen radical is a radical of the formula ##STR4## where R.sup.3 and R.sup.4 are as defined above; preferably R.sup.3 and R.sup.4 are both hydrogen.
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 atoms. The heteroaryl radical may be 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, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl and indolyl each of which may be optionally substituted as mentioned above.
A particularly preferred R.sup.1 group is pyridinyl, particularly 2-pyridyl.
When R is a heteroaryl radical it is preferably optionally substituted pyrimidyl (particularly 2-pyrimidyl), 1,2-benzisothiazolyl, indolyl (lower)alkox
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Hiltmann et al. "2-Acylamino pyridine derivatives with morphine agonistic and morphine antagonistic properties" CA 81:37463b, 1974.
Alan Chapman White
Cliffe Ian Anthony
Mark Antony Ashwell
Reinhardt Bernhard Baudy
Ward Terence James
American Home Products Corporation
Chang Ceila
John Wyeth & Brother Limited
Seifert Arthur G.
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