US10377711B2 – August 13, 2019 – Cannabinoid type 1 receptor modulators

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Inventors :

Ruth Ross; Iain Greig; Matteo Zanda; Chih-Chung Tseng

Owner :

THE UNIVERSITY COURT OF THE UNIVERSITY OF ABERDEEN THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO

Application Number :

US15507079

Document Number :

US10377711B2

Priority Date :

August 26, 2015

Filing Date :

August 26, 2015

Date of Grant/ Publication :

August 13, 2019

Class :

C07D209 / 10; C07D209 / 12; C07D401 / 04; C07D405 / 06; C07D409 / 06; C07D209 / 14; A61P25 / 14; A61P25 / 34; A61P27 / 02; A61P17 / 06; A61P27 / 06; A61P9 / 10; A61P19 / 00; A61P25 / 28; A61P25 / 30; A61P43 / 00; A61P1 / 16; A61P9 / 00; A61P11 / 06; A61P25 / 22; A61P25 / 32; A61P19 / 02; A61P9 / 12; A61P13 / 12; A61P25 / 18; A61P25 / 24; A61P1 / 00; A61P19 / 08; A61P25 / 00; A61P25 / 08; A61P25 / 16; A61P29 / 00; A61P1 / 08; A61P19 / 10; A61P35 / 00

Abstract

The present disclosure relates to indole derivatives of the formula (I) which are cannabinoid type 1 receptor modulators and which are useful in the treatment of diseases in which modulation of the receptor is beneficial; to processes for their preparation; to pharmaceutical compositions comprising them; and to methods of using them.

Claim(s)

1. A compound of the Formula (I) wherein, W is (C 1 -C 10 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 10 )-heterocycloalkyl, (C 6 -C 10 )-aryl, or (C 5 -C 10 )-heteroaryl, each of which is optionally substituted with one or more of halo, —CF 3 , —OCF 3 , —CN, —NO 2 , —R, —OR, —SR, —NR 2 , —NR? 2 , —C(?O)R, —C(?O)OR, —NRC(?O)R, —C(?O)NR 2 , —C(?O)NR? 2 , —S(?O) 2 NR 2 , —S(?O) 2 NR? 2 , —NRS(?O) 2 R, —S(?O) 2 R or —S(?O)CF 3 , wherein R is independently or simultaneously H, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, phenyl or benzyl, and R? is independently or simultaneously H, azetidino, pyrrolidino, piperidino, piperazino, morpholino, azepano, or diazepano; X and X? are independently or simultaneously (C 0 -C 4 )-alkylene, optionally substituted with one or more of halo, —CF 3 , OH, OCF 3 , or —O—(C 1 -C 4 )alkyl; Z is —CH 2 CF 3 or —C(?O)CF 3 ; Ring V is (C 3 -C 10 )-cycloalkyl, (C 3 -C 10 )-heterocycloalkyl, (C 6 -C 10 )-aryl, or (C 5 -C 10 )-heteroaryl, each of which is optionally substituted with one or more of the optional substituents defined in the variable W; R 1 is halo, —CF 3 , —OCF 3 , —CN, —NO 2 , —R 2 , —OR 2 , —SR, —N(R 2 ) 2 , —(NR 2? ) 2 , —C(?O)R 2 , —C(?O)OR 2 ,—NR 2 C(?O)R 2 , —C(?O)N(R 2 ) 2 , —C(?O)N(R 2? ) 2 , —S(?O) 2 N(R 2 ), —S(?O) 2 N(R 2? ) 2 , —NRS(?O) 2 R, —S(?O) 2 R 2 or —S(?O)CF 3 , wherein R 2 is independently or simultaneously H, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, phenyl or benzyl, and R 2? is independently or simultaneously H, azetidino, pyrrolidino, piperidino, piperazino, morpholino, azepano, or diazepano; R 3 is H or (C 1 -C 6 )alkyl; R? is halo, —CF 3 , —OCF 3 , —CN, —NO 2 , —R 4 , —OR 4 , —SR, —N(R 4 ) 2 , —(NR 4? ) 2 , —C(?O)R 4 , —C(?O)OR 4 , —NR 4 C(?O)R 4 , —C(?O)N(R 4 ) 2 , —C(?O)N(R 4? ) 2 , —S(?O) 2 N(R 4 ) 2 , —S(?O) 2 N(R 4? ) 2 , —NR 4 S(?O) 2 R 4 , —S(?O) 2 R 4 or —S(?O)CF 3 , wherein R 4 is independently or simultaneously H, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, phenyl or benzyl, and R 4? is independently or simultaneously H, azetidino, pyrrolidino, piperidino, piperazino, morpholino, azepano, or diazepano; p is the integer 0, 1, 2 or 3, and pharmaceutically acceptable salts, stereoisomers, and/or solvates thereof.

Summary

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