Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1999-06-14
2000-07-25
Killos, Paul J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
A01N 3302
Patent
active
060937475
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION
The present invention relates to new 1,7,7-trimethyl-bicyclo[2.2.1]heptane derivatives, a process for the preparation thereof and the use of said compounds as pharmaceutical active ingredient.
BACKGROUND OF THE INVENTION
It is known that (1R,2S,4R)-(-)-2-phenyl-2-dimethylaminoethoxy-1,7,7-trimethyl-bicyclo[2.2. 1]heptane is a non-benzodiazepine type potential anxiolytic compound. The INN of (1R,2S,4R)-(-)-2-phenyl-2-dimethylaminoethoxy-1,7,7-trimethyl-bicyclo[2.2. 1]heptane-hemifumarate is deramciclane (Hungarian patent No 179,164).
SUMMARY OF THE INVENTION
It is the object of the present invention to provide new 1,7,7-trimethyl-bicyclo[2.2.1]heptane derivatives which have a similar structure to that of (1R,2S,4R)-(-)-2-phenyl-2-dimethylaminoethoxy-1,7,7-trimethyl-bicyclo[2.2. 1]heptane, but are different in their receptor profile, mechanism of action and anxiolytic animal test model.
The above object is reached by the new compounds of the present invention.
According to an aspect of the present invention there is provided the new compound of the Formula I and pharmaceutically acceptable acid addition salts thereof.
According to a further aspect of the present invention there is provided a process for the preparation of the new compound of the Formula ##STR2## and pharmaceutically acceptable acid addition salts thereof.
According to a still further aspect of the present invention there are provided pharmaceutical compositions comprising as active ingredient the compound of the Formula I or pharmaceutically acceptable acid addition salts thereof.
According to a still further aspect of the present invention there is provided a process for the preparation of the above pharmaceutical compositions.
According to a still further aspect of the present invention there is provided the use of the compound of the Formula I and pharmaceutically acceptable acid additon salts thereof as active ingredient of pharmaceutical compositions, having particularly anxiolytic effect.
The compound of the Formula I and pharmaceutically acceptable acid addition salts thereof possess valuable anxiolytic properties.
The compound of the Formula I may be present in racemic or optically active form. The present invention encompasses both the racemic and the optically active forms.
According to a particularly preferable feature of the present invention there is provided (1R,2S,4R)-(-)-2-phenyl-2-methylaminoethoxy-1,7,7-trimethyl-bicyclo[2.2.1] heptane and pharmaceutically acceptable acid addition salts thereof.
DETAILED DESCRIPTION OF THE INVENTION
The compound of the Formula I and pharmaceutically acceptable acid addition salts may be used for anxiolytic treatment by administering to a patient in need of such treatment a pharmaceutically active amount of the compound of the Formula I or a pharmaceutically acceptable acid addition salt thereof. In said treatment it is preferred to use as active ingredient (1R,2S,4R)-(-)-2-phenyl-2-methylaminoethoxy-1,7,7-trimethyl-bicyclo[2.2.1] heptane and salts thereof.
The pharmaceutically acceptable acid addition salts of the compound of the Formula I may be salts formed with inorganic or organic acids. For salt formation e.g. hydrogen halides such as hydrochloric acid or hydrogen bromide; or sulphuric acid, nitric acid, phosphoric acid, acetic acid, propionic acid, malic acid, lactic acid, maleic acid, fumaric acid, tartaric acid, succinic acid, methanesulfonic acid, p-toluenesulfonic acid, etc. may be used. Salts formed with fumaric acid proved to be particularly advantageous.
According to the process of the present invention the compound of the Formula ##STR3## and pharmaceutically acceptable acid addition salts thereof may be prepared by ##STR4##
or ##STR5##
(wherein R is a protecting group); obtained into the optically active isomers and if desired converting the compound of the Formula I into a pharmaceutically acceptable acid addition salt or setting free the base from a salt.
According to process a.) demethylation may be preferably carried out by react
Abermann Miklos
Blasko Gabor
Bojti Erzsebet Kaufmanne
Budai Zoltan
Egyed Andras
Egis Gyogyszergyar Rt.
Killos Paul J.
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