Preparation of indane derivatives for treating and preventing psychiatric diseases.

Kevin James Gillen (Inventor), Jonathan Gillespie (Inventor), Craig Jamieson (Inventor), John Kinnaird Ferguson MacLean (Inventor), Elizabeth Margaret Moir (Inventor), Zoran. Rankovic (Inventor)

Research output: Patent

Abstract

The present invention relates to indane deriv. I [L1 = O, (CR5R6)m, OCR7R8, CR9R10O; L2 = NR11SO2 or SO2NR12; X1-X4 = N or CR1 with the proviso that only one of X1-X4 can be N; R1 = H, alkyl, cycloalkyl, etc.; R2 = alkyl, cycloalkyl, alkoxy, CN; R3 = H, alkyl, cycloalkyl, etc.; R4 = H, alkyl, alkenyl, etc.; R5-R12 = H or alkyl; m = 1-2; n = 0-1; Y1-Y3 = N or CR29 with the proviso that only one of Y1-Y3 can be N; R29 = H or (halo)alkyl; with the proviso that when L1 = (CR5R6)m and L2 is a substituent at the 2-position, n cannot be 0], or to a pharmaceutically acceptable salt or solvate thereof. Over sixty compds. I were prepd. E.g., a multi-step synthesis of (S)-II, starting from 2-aminoindane hydrochloride, is given. Compds. I exhibit pos. modulation of the AMPA receptor having EC50 values in the range 0.3 μM to 30 μM. The present invention also relates to a pharmaceutical compn. comprising one or more of indane derivs. I and to their use in therapy, for instance in the treatment or prevention of psychiatric diseases where an enhancement of synaptic responses mediated by AMPA receptors is required, including schizophrenia, depression and Alzheimer' s disease.
LanguageEnglish
Patent numberWO2010115952A1
Publication statusPublished - 14 Oct 2010

Fingerprint

AMPA Receptors
Psychiatry
Schizophrenia
Alzheimer Disease
Salts
Depression
Pharmaceutical Preparations
Therapeutics
alkoxyl radical
2-aminoindan

Keywords

  • indane derivatives
  • psychiatric diseases

Cite this

Gillen, K. J., Gillespie, J., Jamieson, C., MacLean, J. K. F., Moir, E. M., & Rankovic, Z. (2010). Preparation of indane derivatives for treating and preventing psychiatric diseases. (Patent No. WO2010115952A1).
Gillen, Kevin James (Inventor) ; Gillespie, Jonathan (Inventor) ; Jamieson, Craig (Inventor) ; MacLean, John Kinnaird Ferguson (Inventor) ; Moir, Elizabeth Margaret (Inventor) ; Rankovic, Zoran. (Inventor). / Preparation of indane derivatives for treating and preventing psychiatric diseases. Patent No.: WO2010115952A1.
@misc{bcad0450401448109ee8d54fd4ac7142,
title = "Preparation of indane derivatives for treating and preventing psychiatric diseases.",
abstract = "The present invention relates to indane deriv. I [L1 = O, (CR5R6)m, OCR7R8, CR9R10O; L2 = NR11SO2 or SO2NR12; X1-X4 = N or CR1 with the proviso that only one of X1-X4 can be N; R1 = H, alkyl, cycloalkyl, etc.; R2 = alkyl, cycloalkyl, alkoxy, CN; R3 = H, alkyl, cycloalkyl, etc.; R4 = H, alkyl, alkenyl, etc.; R5-R12 = H or alkyl; m = 1-2; n = 0-1; Y1-Y3 = N or CR29 with the proviso that only one of Y1-Y3 can be N; R29 = H or (halo)alkyl; with the proviso that when L1 = (CR5R6)m and L2 is a substituent at the 2-position, n cannot be 0], or to a pharmaceutically acceptable salt or solvate thereof. Over sixty compds. I were prepd. E.g., a multi-step synthesis of (S)-II, starting from 2-aminoindane hydrochloride, is given. Compds. I exhibit pos. modulation of the AMPA receptor having EC50 values in the range 0.3 μM to 30 μM. The present invention also relates to a pharmaceutical compn. comprising one or more of indane derivs. I and to their use in therapy, for instance in the treatment or prevention of psychiatric diseases where an enhancement of synaptic responses mediated by AMPA receptors is required, including schizophrenia, depression and Alzheimer' s disease.",
keywords = "indane derivatives , psychiatric diseases",
author = "Gillen, {Kevin James} and Jonathan Gillespie and Craig Jamieson and MacLean, {John Kinnaird Ferguson} and Moir, {Elizabeth Margaret} and Zoran. Rankovic",
note = "CAPLUS AN 2010:1284635(Patent); WO2010115952A1",
year = "2010",
month = "10",
day = "14",
language = "English",
type = "Patent",

}

Gillen, KJ, Gillespie, J, Jamieson, C, MacLean, JKF, Moir, EM & Rankovic, Z 2010, Preparation of indane derivatives for treating and preventing psychiatric diseases., Patent No. WO2010115952A1.

Preparation of indane derivatives for treating and preventing psychiatric diseases. / Gillen, Kevin James (Inventor); Gillespie, Jonathan (Inventor); Jamieson, Craig (Inventor); MacLean, John Kinnaird Ferguson (Inventor); Moir, Elizabeth Margaret (Inventor); Rankovic, Zoran. (Inventor).

Patent No.: WO2010115952A1.

Research output: Patent

TY - PAT

T1 - Preparation of indane derivatives for treating and preventing psychiatric diseases.

AU - Gillen, Kevin James

AU - Gillespie, Jonathan

AU - Jamieson, Craig

AU - MacLean, John Kinnaird Ferguson

AU - Moir, Elizabeth Margaret

AU - Rankovic, Zoran.

N1 - CAPLUS AN 2010:1284635(Patent)

PY - 2010/10/14

Y1 - 2010/10/14

N2 - The present invention relates to indane deriv. I [L1 = O, (CR5R6)m, OCR7R8, CR9R10O; L2 = NR11SO2 or SO2NR12; X1-X4 = N or CR1 with the proviso that only one of X1-X4 can be N; R1 = H, alkyl, cycloalkyl, etc.; R2 = alkyl, cycloalkyl, alkoxy, CN; R3 = H, alkyl, cycloalkyl, etc.; R4 = H, alkyl, alkenyl, etc.; R5-R12 = H or alkyl; m = 1-2; n = 0-1; Y1-Y3 = N or CR29 with the proviso that only one of Y1-Y3 can be N; R29 = H or (halo)alkyl; with the proviso that when L1 = (CR5R6)m and L2 is a substituent at the 2-position, n cannot be 0], or to a pharmaceutically acceptable salt or solvate thereof. Over sixty compds. I were prepd. E.g., a multi-step synthesis of (S)-II, starting from 2-aminoindane hydrochloride, is given. Compds. I exhibit pos. modulation of the AMPA receptor having EC50 values in the range 0.3 μM to 30 μM. The present invention also relates to a pharmaceutical compn. comprising one or more of indane derivs. I and to their use in therapy, for instance in the treatment or prevention of psychiatric diseases where an enhancement of synaptic responses mediated by AMPA receptors is required, including schizophrenia, depression and Alzheimer' s disease.

AB - The present invention relates to indane deriv. I [L1 = O, (CR5R6)m, OCR7R8, CR9R10O; L2 = NR11SO2 or SO2NR12; X1-X4 = N or CR1 with the proviso that only one of X1-X4 can be N; R1 = H, alkyl, cycloalkyl, etc.; R2 = alkyl, cycloalkyl, alkoxy, CN; R3 = H, alkyl, cycloalkyl, etc.; R4 = H, alkyl, alkenyl, etc.; R5-R12 = H or alkyl; m = 1-2; n = 0-1; Y1-Y3 = N or CR29 with the proviso that only one of Y1-Y3 can be N; R29 = H or (halo)alkyl; with the proviso that when L1 = (CR5R6)m and L2 is a substituent at the 2-position, n cannot be 0], or to a pharmaceutically acceptable salt or solvate thereof. Over sixty compds. I were prepd. E.g., a multi-step synthesis of (S)-II, starting from 2-aminoindane hydrochloride, is given. Compds. I exhibit pos. modulation of the AMPA receptor having EC50 values in the range 0.3 μM to 30 μM. The present invention also relates to a pharmaceutical compn. comprising one or more of indane derivs. I and to their use in therapy, for instance in the treatment or prevention of psychiatric diseases where an enhancement of synaptic responses mediated by AMPA receptors is required, including schizophrenia, depression and Alzheimer' s disease.

KW - indane derivatives

KW - psychiatric diseases

M3 - Patent

M1 - WO2010115952A1

ER -

Gillen KJ, Gillespie J, Jamieson C, MacLean JKF, Moir EM, Rankovic Z, inventors. Preparation of indane derivatives for treating and preventing psychiatric diseases. WO2010115952A1. 2010 Oct 14.