2-amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives and a process for the preparation thereof
AssigneeHoffmann-La Roche Inc.
InventorsGeo Adam, Philippe Nicolas Huguenin-Virchaux, Vincent Mutel, Heinz Stadler, Thomas Johannes Woltering
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Abstract
The present invention relates to the compound of formulae ##STR1## and to a process for the manufacture of compounds of the general formula ##STR2## which are ligands for the metabotropic glutamate receptors of group II, wherein T is tritium; R.sup.1 is hydroxy, lower alkoxy, lower alkenyloxy, benzyloxy, hydrogen, deuterium or tritium; R.sup.11 is hydrogen, deuterium or tritium, hydroxy or amino, and R.sup.2 is hydrogen or tritium, or R.sup.1 and R.sup.2 form a bond.
Claims18
A process for the preparation of a compound of formula ##STR35## wherein R.sup.1 is hydroxy, lower alkoxy, lower alkenyloxy, benzyloxy, hydrogen, deuterium or tritium,
- R.sup.11 is hydrogen, deuterium, tritium, hydroxy or amino, and
- R.sup.2 is hydrogen or tritium, or
- R.sup.1 and R.sup.2 form a bond,
- which process comprises:
- a) reacting a compound of formula ##STR36## with a reducing agent, to obtain a compound of formula VII and a compound of formula X ##STR37## wherein R'" and R" are each independently selected from benzyl or lower alkyl, and then,
- b) reacting with a reducing agent to reduce the azide group, and
- c) hydrolyzing the ester groups,
- to obtain a compound of formula I.
A process for the preparation of a compound of formula VII ##STR40## wherein R'" and R" are each independently selected from benzyl or lower alkyl, comprising reacting a compound of formula IX ##STR41## with a reducing agent, to obtain a compound of formula VII.
A process for the preparation of a compound of formula ##STR42## wherein R.sup.1 is hydroxy, lower alkoxy, lower alkenyloxy, benzyloxy, hydrogen, deuterium or tritium,
- R.sup.11 is hydrogen, deuterium, tritium, hydroxy or amino, and
- R.sup.2 is hydrogen or tritium, or
- R.sup.1 and R.sup.2 form a bond,
- which process comprises:
- a) providing a compound of formula VII, ##STR43## wherein R'" and R" are each independently selected from benzyl or lower alkyl and then,
- b) reacting with a reducing agent to reduce the azide group, and
- c) hydrolyzing the ester groups, to obtain a compound of formula I.
A process for the preparation of a compound of formula ##STR46## wherein R.sup.1 is hydroxy, lower alkoxy, lower alkenyloxy, benzyloxy, hydrogen, deuterium or tritium,
- R.sup.11 is hydrogen, deuterium, tritium, hydroxy or amino, and
- R.sup.2 is hydrogen or tritium, or
- R.sup.1 and R.sup.2 form a bond,
- which process comprises:
- a) providing a compound of formula X, ##STR47## wherein R'" and R" are each independently selected from benzyl or lower alkyl and then,
- b) reacting with a reducing agent to reduce the azide group, and
- c) hydrolyzing the ester groups, to obtain a compound of formula I.
A compound of formula ##STR50##
A compound of formula wherein T is tritium.
A compound of formula ##STR51## wherein R" and R"" are each independently selected from benzyl or lower alkyl.
A method of controlling or preventing a neurological disease or a psychiatric disorder comprising administering to a patient in need of treatment an effective amount of the compound of formula I-A. ##STR52##
Dependencies are inferred from the claim text.