Author Topic: Preparation of 2-aminoindane analogs  (Read 495 times)

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Vitus_Verdegast

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Preparation of 2-aminoindane analogs
« on: October 01, 2003, 03:37:00 AM »
Preparation of 2-aminoindane analogs.
Curry, Kenneth (IGT Pharma Inc., Can.).
PCT Int. Appl.  (2001),
CAN 134:86547, AN 2001:31449
65 pp.

Patent EP1194400



Abstract

2-Aminoindane analogs I [R1, R2 = H or an acidic group selected from carboxy, phosphono, phosphino, sulfono, sulfino, borono, tetrazolyl, isoxazolyl, -(CH2)n-carboxy, -phosphono, -phosphino, -sulfono, -sulfino, -borono, -tetrazolyl, or -isoxazolyl, where n = 1-6; X is an acidic group selected from carboxy, phosphono, phosphino, sulfono, sulfino, borono, tetrazolyl, or isoxazolyl; Y is a basic group selected from aliph. or arom. primary, secondary, or tertiary amino, quaternary ammonium salts, imidazolyl, guanidino, boronoamino, allyl, urea, or thiourea; m = 0 or 1; R3-6 = H, nitro, amino, halo, tritium, trifluoromethyl, trifluoroacetyl, sulfo, carboxy, carbamoyl, or sulfamoyl] or their stereoisomers or pharmaceutically acceptable salts were prepd. as modulators of metabotropic glutamate receptors (mGluRs) for use in treating diseases of the central nervous system. 
Thus, 2-amino-2-carboxy-1-indaneacetic acid (cis and trans isomers) were prepd. by a multistep procedure starting from 1,2-phenylenediacetonitrile.  The cAMP assay showed that the cis isomer is a Group II/III mGluRs antagonist (EC50 = 1.2x10-9 M) and the trans isomer is a Group II/III mGluRs agonist (EC50 = 1.1x10-7 M).


The present invention relates to therapeutically active 2-aminoindane analogs of formula (I). Also provided is a method of preparing compounds of formula (I), and pharmaceutical compositions comprising the compounds. The novel compounds act as modulators of metabotropic glutamate receptors and, as such, are useful in treating diseases of the central nervous system related to the metabotropic glutamate receptor system.


Vitus_Verdegast

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2-aminoindans as selective dopamine D3 ligands
« Reply #1 on: October 01, 2003, 04:17:00 AM »
2-aminoindans as selective dopamine D3 ligands
Leiby Jeffrey A ; Romero Arthur G (Upjohn Co USA)

Abstract
 
Compounds and their pharmaceutically acceptable salts suitable for treating central nervous system disorders associated with the dopamine D3 receptor activity of Formula I: wherein R1 and R2 are independently H, C1-8 alkyl or C1-8 alkylAryl; X is CH2R3 or NHSO2R4; Y is hydrogen, CH2R3, NHSO2R4, CONR1R2, SO2NR1R2, SO2CH3, halogen, OSO2CF3, SCH3 or OCH3; R3 is NHSO2R4, SO2R4, CONR1R2 or Aryl; and R4 is NR1R2, C1-C8 alkyl, Aryl or C1-C8 alkylAryl.


Vitus_Verdegast

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Whoops
« Reply #2 on: October 02, 2003, 04:52:00 PM »
;D

Forgot to add the reference for above:

Patent US5936000