Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1991-01-25
1993-08-17
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514618, 514619, 564162, 564163, 564164, 564165, 564167, 564168, A61K 31165
Patent
active
052369579
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to N-phenylalkyl substituted .alpha.-amino carboxamide derivatives, to their use as therapeutic agents, to a process for their preparation and to pharmaceutical compositions containing them.
Other N-substituted .alpha.-amino carboxamide derivatives are known as having pharmacological properties, for instance those described by British patent No. 1140748. The compounds according to this prior art document are useful in the treatment and prophylaxis of such diseases as coronary artery disease and atherosclerosis; moreover they are useful in the treatment of inflammatory conditions such as rheumatoid arthritis.
Further substituted amino acid derivatives are known as enkephalinase inhibitors, analgesics and hypotensives from EP-A-0038758.
Still other substituted glycine and alanine derivatives are disclosed by U.S. Pat. No. 4,049,663. The compounds according to this document have utility as oral analgesics.
It has now been found that N-phenylalkyl substituted .alpha.-amino carboxamide derivates of general formula (I), as herein defined, and the pharmaceutically acceptable salts thereof are active as anti-epileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic, and/or hypnotic agents.
Accordingly the present invention relates, as a first object, to the use of a compound of formula (I), as herein defined, or a pharmaceutically acceptable salt thereof, as an antiepileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic, and/or hypnotic agent and to the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the preparation of a pharmaceutical composition for use as an anti-epileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic and/or hypnotic agent.
The compounds of formula (I) have the following general formula: ##STR2## wherein R is C.sub.1 -C.sub.8 alkyl; a C.sub.3 -C.sub.8 cycloalkyl, furyl, thienyl or pyridyl ring; or a phenyl ring unsubstituted or substituted by 1 to 4 substituents independently chosen from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy and trifluoromethyl; group, wherein m is an integer of 1 to 4, one of p and q is zero and the other is zero or an integer of 1 to 4, and X is --O--, --S-- or --NR.sub.4 -- in which R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; alkyl; hydroxy or by a phenyl ring optionally substituted by 1 to 4 substituents independently chosen from halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy and trifluoromethyl; adjacent carbon atom form a C.sub.3 -C.sub.6 cycloalkyl ring; each of R.sub.5 and R.sub.6, independently, is hydrogen or C.sub.1 -C.sub.6 alkyl; and wherein when R is C.sub.1 -C.sub.8 alkyl, then A is a --(CH.sub.2).sub.p --X--(CH.sub.2).sub.q -- group in which p and q are both zero and X is as defined above. compounds" and as the "compounds of the invention". The present invention includes all the possible optical isomers of the compounds of formula (I) and their mixtures, as well as the metabolites of the compounds of formula (I). The present invention also includes within its scope pharmaceutically acceptable bioprecursors and prodrugs of the compounds of formula (I), i.e. compounds, which have a formula different to formula (I), but which nevertheless are directly or indirectly converted in vivo into a compound of formula (I) upon administration to a human being.
Pharmaceutically acceptable salts of the compounds of formula (I) include acid addition salts with inorganic acids, e.g. nitric, hydrochloric, hydrobromic, sulphuric, perchloric, and phosphoric acid, or organic acids, e.g. acetic, propionic, glycolic, lactic, oxalic, malonic, malic, tartaric, citric, benzoic, cinnamic, mandelic, methanesulfonic and salicyclic acids.
The alkyl, alkylamino, alkylthio and alkoxy groups may be branched or straight chain groups. When R.sub.5 and R.sub.6 are both alkyl groups, the alkyl group for R.sub.5 may be same as or different from the alkyl group for R.sub.6. A halogen atom is preferably fluorine, chlorine or bromine, in particular fluorine or
REFERENCES:
patent: 4049663 (1977-09-01), Harper et al.
patent: 4267354 (1981-05-01), Krapcho et al.
patent: 4311853 (1982-01-01), Cree
patent: 4513009 (1985-04-01), Roques et al.
patent: 4629468 (1987-01-01), Roncucci et al.
patent: 4631287 (1986-12-01), Chakraborty et al.
patent: 4715619 (1988-02-01), Chakraborty et al.
patent: 4728688 (1988-03-01), Tizzard et al.
patent: 4839369 (1989-06-01), Youssefyeh et al.
patent: 4927836 (1990-05-01), Holloway et al.
Eur. Neuropsychopharmacol, 1, pp. 317-319, "New Anticonvulsants with Selective MAO-B Inhibitory Activity", Dostert et al. (Jan. 1991).
Bonsignori Alberto
Dostert Philippe
Heidempergher Franco
Pevarello Paolo
Roncucci Romeo
Burn Brian M.
Farmitalia Carlo Erba Srl
Raymond Richard L.
LandOfFree
N-phenylalkyl substituted .alpha.-amino carboxamide derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with N-phenylalkyl substituted .alpha.-amino carboxamide derivatives , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-phenylalkyl substituted .alpha.-amino carboxamide derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2244041