Genzyme Corporation

Anormed, Inc.

Wen Yang

Renato Skerlj

Gary James Bridger

Ernest John McEachern

Yuanxi Zhou

Markus Metz

Tong-Shuang Li

Elyse Bourque

Jonathan Langille

David Earl Bogucki

Krystyna A Skupinska

Curtis Harwig

Yongbao Zhu

Siqiao Nan

Christen M Giandomenico

Maria Rosaria Di Fluri

Ian R Baird

The present invention relates to chemokine receptor binding compounds, pharmaceutical compositions and their use. More specifically, the present invention relates to modulators of chemokine receptor activity, preferably modulators of CCR5. These compounds demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

Chemokine receptor binding compounds

This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.

Synthesis of enantiomerically pure amino-substituted fused bicyclic rings

This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)&#x2014; and (S)&#x2014; forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)&#x2014; or (S)&#x2014; enantiomer of primary amino-substituted fused bicyclic ring systems.

Cyclic polyamines containing N nitrogens on the ring are protected with high yields in a N-1 manner, e.g. all protected but one amino group, by using certain fluoro-containing agents that offer easy deprotection. Preferably, a new process for preparing 1,1&prime;-&lsqb;1,4-phenylenebis (methylene)&rsqb;-bis1,4,8,11-tetraazacyclotetradecane is disclosed.

Process for preparation of N-1 protected N ring nitrogen containing cyclic polyamines and products thereof

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Aldergrove, Canada

Wen Yang