Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-07-27
2000-03-07
Davis, Zinna Northington
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514332, 514357, 546255, 546339, 546346, 546329, 546340, 546257, A61K 3144, C07D21170, C07D21172, C07D21322
Patent
active
060340908
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel 4-substituted 1-phenylalkyl-1,2,3,6-tetrahydropyridines with neurotrophic and neuroprotective activity, to a method of preparing them and to pharmaceutical compositions containing them.
EP-0 458 696 describes the use of a 1-(2-naphthylethyl)4-(3-trifluoro-methylphenyl)-1,2,3,6tetrahydropyridine for the preparation of drugs intended for the treatment of cerebral and neuronal disorders.
WO 93/11107 describes piperidines and tetrahydropyridines with protective activity against the damage caused by hypoxic/ischemic states.
It has now been found that certain phenylalyl-1,2,3,6-tetrahydropyridines substituted by a phenyl or pyridyl group exert a neurotrophic action on the nervous system which is similar to the action of nerve growth factor (NGF), and can restore the function of damaged cells or cells exhibiting anomalies in their physiological functions.
According to one of its features, the present invention therefore relates to the compounds of formula (I): ##STR1## in which: Y is --CH-- or --N--; (C.sub.1 -C.sub.4)alkoxy group; -C.sub.7)carboxyalkyl, a (C.sub.1 -C.sub.4)alkoxy-carbonyl(C.sub.1 -C.sub.6)alkyl, a (C.sub.3 -C.sub.7)carboxyalkoxy or a (C.sub.1 -C.sub.4)alkoxycarbonyl-(C.sub.1 -C.sub.6)alkoxy; -C.sub.7)cycloalkoxy, (C.sub.3 -C.sub.7)-cycloalkylmethyl, (C.sub.3 -C.sub.7)cycloalkylamino and cyclohexenyl, it being possible for said radical to be substituted by a halogen, hydroxyl, (C.sub.1 -C.sub.4)-alkoxy, carboxyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, amino or mono- or di-(C.sub.1 -C.sub.4)-alkylamino; or -C.sub.3)alkyl-phenylamino, phenylmethyl, phenylethyl, phenylcarbonyl, phenylthio, phenylsulfonyl, phenylsulfinyl and styryl, it being possible for said group to be monosubstituted or polysubstituted on the phenyl group by a halogen, CF.sub.3, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, cyano, amino, mono- or di-(C.sub.1 -C.sub.4)alkyl-amino, (C.sub.1 -C.sub.4)acylamino, carboxyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, aminocarbonyl, mono- or di-(C.sub.1 -C.sub.4)alkylaminocarbonyl, amino(C.sub.1 -C.sub.4)alkyl, hydroxy(C.sub.1 -C.sub.4)alkyl or halogeno(C.sub.1 -C.sub.4)alkyl;
In the present description the term "(C.sub.1 -C.sub.3)alkyl" denotes methyl, ethyl, n-propyl and i-propyl groups.
The term "(C.sub.1 -C.sub.4)alkyl" denotes methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl and 1-butyl groups.
The term "(C.sub.1 -C.sub.6)alkyl" denotes a hydrocarbon radical containing from 1 to 6 carbon atoms, for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, n-hexyl, i-hexyl, etc.
The term "alkoxy" denotes a hydroxyl group substituted by a (C.sub.1 -C.sub.6)alkyl, advantageously (C.sub.1 -C.sub.4)alkyl and preferably (C.sub.1 -C.sub.3)alkyl group.
If X is a phenyl group, the nomenclature used for the biphenylyl radical is in accordance with the IUPAC rules, i.e. the positions of the two rings are numbered as follows: ##STR2## and the radicals of this structure have the following names: ##STR3##
Among the compounds of formula (I) in which X is a group (c), one preferred group is represented by the compounds in which the phenyl is substituted by 1 to 3 halogens, 1 to 3 CF.sub.3, 1 to 3 (C.sub.1 -C.sub.4)alkyl, 1 to 3 (C.sub.1 -C.sub.4)alkoxy, 1 to 3 cyano, 1 to 3 amino, 1 to 3 mono- or di-(C.sub.1 -C.sub.4)alkylamino, 1 to 3 (C.sub.1 -C.sub.4)-acylamino, 1 to 3 carboxyl, 1 to 3 (C.sub.1 -C.sub.4)alkoxycarbonyl, 1 to 3 aminocarbonyl, 1 to 3 mono- or di-(C.sub.1 -C.sub.4)alkylaminocarbonyl, 1 to 3 amino(C.sub.1 -C.sub.4)alkyl, 1 to 3 hydroxy(C.sub.1 -C.sub.4)alkyl or 1 to 3 halogeno(C.sub.1 -C.sub.4)alkyl.
Another preferred group consists of the compounds of formula (I) in which Y is a group --CH-- and R.sub.1 is CF.sub.3.
Another preferred group consists of the compounds of formula (I) in which Y is a nitrogen atom and R.sub.1 is a chlorine atom.
Another preferred group consists of the compounds of formula (I) in which X is a (C.sub.1 -C.sub.6)alkyl group, especially ethyl.
Particularly
REFERENCES:
patent: 3954871 (1976-05-01), Buu-Hoi et al.
patent: 5109005 (1992-04-01), Croci et al.
patent: 5229389 (1993-07-01), Coude et al.
patent: 5270320 (1993-12-01), Coude et al.
Baroni Marco
Cardamone Rosanna
Fournier Jacqueline
Guzzi Umberto
Alexander Michael D.
Davis Zinna Northington
Robinson Binta
Sanofi-Synthlabo
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