Design, synthesis, and biological activity of piperidine diamine derivatives as factor Xa inhibitor.
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Mochizuki A, Nakamoto Y, Naito H, Uoto K, Ohta T
Design, synthesis, and biological activity of piperidine diamine derivatives as factor Xa inhibitor.
Bioorg Med Chem Lett. 2008 Jan 15;18(2):782-7. Epub 2007 Nov 17.
- PubMed ID
- 18039572 [ View in PubMed]
- Abstract
Previously, we identified cyclohexane diamine derivative 1 as orally bioavailable factor Xa inhibitor. We have investigated two racemic cis-piperidine diamine derivatives 2 and 3 based on 1. Compounds 2a-e showed higher fXa inhibitory activity, anticoagulant activity, and aqueous solubility than 3a-e having same substituent. Compounds 2a, 2c, 2e, and 2g-m having sp2 nitrogen, especially amide and urea derivatives, showed potent anticoagulant activity. Compounds 2h and 2k showed high oral activities in rats.
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- Binding Properties
Drug Target Property Measurement pH Temperature (°C) N-((1R,2R)-2-(5-CHLORO-1H-INDOLE-2-CARBOXAMIDO)CYCLOHEXYL)-5-METHYL-4,5,6,7-TETRAHYDROTHIAZOLO[5,4-C]PYRIDINE-2-CARBOXAMIDE Coagulation factor X IC 50 (nM) 41 N/A N/A Details N-((1R,2S)-2-(5-CHLORO-1H-INDOLE-2-CARBOXAMIDO)CYCLOHEXYL)-5-METHYL-4,5,6,7-TETRAHYDROTHIAZOLO[5,4-C]PYRIDINE-2-CARBOXAMIDE Coagulation factor X IC 50 (nM) 16 N/A N/A Details