229008-30-4Relevant articles and documents
Development of a new synthetic route of a non-peptide CCR5 antagonist, TAK-779, for large-scale preparation
Ikemoto, Tomomi,Ito, Tatsuya,Hashimoto, Hideo,Kawarasaki, Tadao,Nishiguchi, Atsuko,Mitsudera, Hiroyuki,Wakimasu, Mitsuhiro,Tomimatsu, Kiminori
, p. 520 - 525 (2000)
A new large-scalable preparation of TAK-779 (1), a non-peptide CCR5 antagonist, has been developed. The route selection was focused on in the process research. The selective reduction of commercially available benzonitrile derivative (4) as the starting material with sodium bis(2-methoxyethoxy)aluminum hydride followed by the Wittig reaction, hydrogenation, and intramolecular acylation gave benzocycloheptanone (7) in good yield. The conversion of α,α-unsaturated carboxylic acid (8) led from 7 to benzyl alcohol (9) and shortened the number of steps using non-protected 4-aminobenzyl alcohol. The reductive alkylation of Me2NH and tetrahydro-4H-pyran-4-one (12) smoothly gave a tertiary amine (3). The coupling of 2 chlorinated 9, and 3 successfully led to an ammonium chloride (1). A new inexpensive preparation which did not require a chromatographic method was achieved.
Quaternary ammonium salts and their use
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, (2008/06/13)
This invention is to provide a compound for antagonizing CCR5, said compound being represented by the formula: wherein R1 is an optionally substituted phenyl or an optionally substituted thienyl; Y is -CH2-, -S- or -O-; and R2, R3 and R4 are independently an optionally substituted aliphatic hydrocarbon group or an optionally substituted alicyclic heterocyclic ring group, and being effective for the prevention and treatment of infectious disease of HIV.
