120128-20-3Relevant articles and documents
The process development of RG 12525 (2-{[4-(Tetrazol-5-ylmethylphenyl)-methoxy]phenoxymethyl}quinoline)
Bridge, Andrew W.,Jones, Ronald H.,Kabir, Humayun,Kee, Alex A.,Lythgoe, David J.,Nakach, Mustafa,Pemberton, Clive,Wrightman, John A.
, p. 9 - 15 (2001)
This contribution describes process improvements to provide a practical and cost-effective synthesis for the manufacture of RG 12525 which resulted in a 3-fold increase in overall yield. Improved solvent systems for chlorination and azidation reactions are described. Adjustments to the tetrazole-forming step eliminated azide sublimation and minimised this risk on scale-up. A robust solvent system was found to control the polymorphic form during crystallisation, which had hitherto been difficult due to the near-equivalence of melting points (154 and 157 °C) of the two known forms.
Therapeutic uses of quinoline derivatives
-
, (2008/06/13)
A method for mediating the activity of PPAR-γ receptor comprising contacting said PPAR-γ receptor with a compound of formula I defined herein. Also disclosed is the treatment of a patient suffering from a physiological disorder capable of being modulated
Approaches to p-hydroxyphenoxymethylquinolines which avoid intermediate chloromethylquinolines for the synthesis of the LTD4 antagonist, RG 12525
O'Brien,Sledeski,Truesdale
, p. 509 - 512 (2007/10/03)
As part of an effort to develop an industrial synthesis of the LTD4 antagonist RG 12525 (1), several approaches to the intermediate (2-quinolinylmethoxy)phenol 3 were investigated that avoided the generation of the lachrymatory sensitizer α-chloro-2-methylquinoline 2. Utilization of a cyclic sulfate in place of α,α'dichloro-o-xylene 4 showed promise as a selective dialkylating agent in the conversion of 3 to RO 12525 (1).