1,2,3,4-tetrahydro-benzofuro[3,2-C]pyridine derivatives

Details 1,2,3,4-tetrahydro-benzofuro[3,2-C]pyridine derivatives 1,2,3,4-tetrahydro-benzofuro[3,2-C]pyridine derivatives

1999-10-04

2000-12-05

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

546 89, 544278, 544281, 544282, 544268, 544331, 544250, 514267, 514265, 514274, 514291, C07D49104, C07D49804, C07D51304, A61K 31435

Patent

active

061567574

DESCRIPTION:

BRIEF SUMMARY
The present invention concerns 1,2,3,4-tetrahydro-benzofuro[3,2-c]pyridine derivatives having central .alpha..sub.2 -adrenoceptor antagonist activity. It further relates to their preparation, compositions comprising them and their use as a medicine. Central .alpha..sub.2 -adrenoceptor antagonists are known to increase noradrenaline release by blocking presynaptic .alpha..sub.2 -receptors which exert an inhibiting control over the release of the neurotransmitter. By increasing the noradrenaline concentrations, .alpha..sub.2 -antagonists can be used clinically for the treatment or prophylaxis of depression, cognitive disturbances, Parkinson's disease, diabetes mellitus, sexual dysfunction and impotence, elevated intraocular pressure, and diseases related to disturbed enterokinesia, since all these conditions are associated with a deficiency of noradrenaline in the central or peripheral nervous system.
The compounds of the present invention are novel and have a specific and selective binding affinity for the different known subtypes of the .alpha..sub.2 -adrenoceptors, i.e. the .alpha..sub.2A, .alpha..sub.2B and .alpha..sub.2C -adrenoceptor.
The present invention concerns the compounds of formula ##STR2## the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein: hydroxy or C.sub.1-4 alkyloxy; formula ##STR3## wherein each X independently represents O, S or NR.sup.12 ; alkylthio, amino or mono- or di(C.sub.1-6 alkyl)amino; R.sup.12 each independently are hydrogen or C.sub.1-6 alky --R.sup.4 -- of formula independently may be replaced by halo, C.sub.1-6 alkyl, aryC.sub.1-6 alkyl, trifluoromethyl, amino, hydroxy, C.sub.1-6 alkyloxy or C.sub.1-10 alkylcarbonyloxy; or where possible, two geminal hydrogen atoms may be replaced by C.sub.1-6 alkylidene or arylC.sub.1-6 alkylidene; or (a-6) to (a-14) each independently may be replaced by C.sub.1-6 alkyl or aryl; and
As used in the foregoing definitions the term halogen is generic to fluoro, chloro, romo and iodo. The term C.sub.1-6 alkyl defines straight and branched saturated hydrocarbons, having from 1 to 6 carbon atoms such as, for example, methyl, ethyl, propyl, butyl, 1-methylethyl, 1,1-dimethylethyl, 2-methylpropyl, pentyl, hexyl and the like. The term C.sub.1-10 alkyl is meant to include C.sub.1-6 alkyl radicals and the higher homologues thereof having 7 to 10 carbon atoms such as, for example, heptyl, octyl, nonyl, decyl and the like. The term C.sub.1-6 alkanediyl defines bivalent straight or branch chained alkanediyl radicals having from 1 to 6 carbon atoms such as, for example, methylene, 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5-pentanediyl, 1,6-hexanediyl and the like; the term C.sub.1-6 alkylidene defines bivalent straight or branch chained alkylidene radicals having from 1 to 6 carbon atoms such as, for example, methylene, ethylidene, 1-propylidene, 1-butylidene, 1-pentylidene, 1-hexylidene and the like.
The addition salts as mentioned herein are meant to comprise the therapeutically active addition salt forms which the compounds of formula (I) are able to form with appropriate acids, such as, for example, inorganic acids such as hydrohalic acids, e.g. hydrochloric or hydrobromic acid; sulfuric; nitric; phosphoric and the like acids; or organic acids such as, for example, acetic, propanoic, hydroxyacetic, lactic, pyruvic, oxalic, malonic, succinic, maleic, fumaric, malic, tartaric, citric, methanesulfonic, ethanesulfonic, benzenesulfonic, p-toluenesulfonic, cyclamic, salicylic, p-aminosalicylic, pamoic and the like acids.
The pharmaceutically acceptable addition salts as mentioned hereinabove are also meant to comprise the therapeutically active non-toxic base, in particular, a metal or amine addition salt forms which the compounds of formula (I) are able to form. Said salts can conveniently be obtained by treating the compounds of formula (I) containing acidic hydrogen atoms with appropriate organic and inorganic bases such as, for example, the ammonium salts, the alkali and ea

REFERENCES:
patent: 4661498 (1987-04-01), Wick et al.
Printout for Aksanova et al. Khim.-Farm. Zh. (1975), 9, 7-9, 1975.

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