820244-71-1

Upstream product

• 748780-94-1 (+)-(1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 748780-95-2 (+)-(1R,2R,3S,5R,6R)-2-amino-6-fluoro-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 820244-65-3 (1R,2R,3S,5R,6R)-2-(tert-butoxycarbonylamino)-6-fluoro-3-{[(trifluoromethyl)sulfonyl]oxy}bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 820244-67-5 (1R,2R,3R,5R,6R)-3-amino-2-(tert-butoxycarbonylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 820244-64-2 (1R,2R,3S,5R,6R)-2-(tert-butoxycarbonylamino)-6-fluoro-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 820244-66-4 (1R,2R,3R,5R,6R)-3-azido-2-(tert-butoxycarbonylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 820244-68-6 (1R,2R,3R,5R,6R)-2-(tert-butoxycarbonylamino)-3-(3,4-dichlorobenzylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 820244-72-2 (1R,2R,3R,5R,6R)-2-amino-3-[(3,4-dichlorobenzyl)(methyl)amino]-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

Synthesis, in vitro pharmacology, and structure-activity relationships of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as mGluR2 antagonists

Chemical modification of the bicyclo[3.1.0]hexane ring C-3 position led to the discovery of 3-alkoxy-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 3-benzylthio-, and 3-benzylamino-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives, metabotropic glutamate receptor 2 (mGluR2) antagonists. In particular, 3-(3,4-dichlorobenzyloxy)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (15ae), (1R,2S,5R,6R)-2-amino-3-(3,4-dichlorobenzylthio)-6-fluorobicyclo[3.1.0]h exane-2,6-carboxylic acid (15at), and (1R,2S,5R,6R)-2-amino-3-(N-(3,4-dichlorobenzylamino))-6-fluorobicyclo[3. 1.0]hexane-2,6-carboxylic (15ba) showed high affinity for the mGluR2 receptor (15ae: Ki = 2.51 nM, 15at: Ki = 1.96 nM, and 15ba: Ki = 3.29 nM) and potent antagonist activity for mGluR2 (15ae; IC50 = 34.21 nM, 15at; IC50 = 13.34 nM, and 15ba; IC50 = 35.96 nM). No significant agonist activity for mGluR2 was observed with 15ae, 15at, or 15ba. This paper reports on the synthesis, in vitro pharmacological profile, and structure-activity relationships (SARs) of 3-substituted-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid.

2-AMINOBICYCLO 3.1.0 HEXANE-2,6-DICARBOXYLIC ESTER DERIVATIVE

A drug effective for the treatment and prevention of psychiatric disorders such as schizophrenia, anxiety and related ailments thereof, depression, bipolar disorder and epilepsy. The drug antagonizes the action of group II metabotropic glutamate receptors

2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivative

One object of the present invention is to provide a drug that is effective in treatments for and prevention of psychiatric disorders and in treatments for and prevention of neurological diseases, inhibiting a Group II metabotropic glutamate receptor. The