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  • Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part II: exploration of 6-6 fused rings as alternative S1 moieties.

Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part II: exploration of 6-6 fused rings as alternative S1 moieties.

Bioorganic & medicinal chemistry (2009-11-11)
Kenji Yoshikawa, Shozo Kobayashi, Yumi Nakamoto, Noriyasu Haginoya, Satoshi Komoriya, Toshiharu Yoshino, Tsutomu Nagata, Akiyoshi Mochizuki, Kengo Watanabe, Makoto Suzuki, Hideyuki Kanno, Toshiharu Ohta
ABSTRACT

A series of cis-1,2-diaminocyclohexane derivatives possessing a 6-6 fused ring for the S1 moiety were synthesized as novel factor Xa (fXa) inhibitors. The synthesis, structure-activity relationship (SAR), and physicochemical properties are reported herein, together with the discovery of compound 45c, which has potent anti-fXa activity, good physicochemical properties and pharmacokinetic (PK) profiles, including a reduced negative food effect.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(1R,2R)-(−)-1,2-Diaminocyclohexane, 98%
Sigma-Aldrich
(±)-trans-1,2-Diaminocyclohexane, 99%
Sigma-Aldrich
1,2-Diaminocyclohexane, mixture of cis and trans, 99%
Sigma-Aldrich
(1S,2S)-(+)-1,2-Diaminocyclohexane, 98%