Difluoroethylamines as an amide isostere in inhibitors of cathepsin K.
Publication
, Journal Article
Isabel, E; Mellon, C; Boyd, MJ; Chauret, N; Deschênes, D; Desmarais, S; Falgueyret, J-P; Gauthier, JY; Khougaz, K; Lau, CK; Léger, S; Li, CS ...
Published in: Bioorganic & medicinal chemistry letters
February 2011
The trifluoroethylamine group found in cathepsin K inhibitors like odanacatib can be replaced by a difluoroethylamine group. This change increased the basicity of the nitrogen which positively impacted the log D. This translated into an improved oral bioavailability in pre-clinical species. Difluoroethylamine compounds exhibit a similar potency against cathepsin K and selectivity profile against other cathepsins when compared to trifluoroethylamine analogs.
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Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
February 2011
Volume
21
Issue
3
Start / End Page
920 / 923
Related Subject Headings
- Rats
- Protease Inhibitors
- Medicinal & Biomolecular Chemistry
- Ethylamines
- Dogs
- Cathepsin K
- Biphenyl Compounds
- Animals
- Amides
- Administration, Oral
Citation
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Isabel, E., Mellon, C., Boyd, M. J., Chauret, N., Deschênes, D., Desmarais, S., … Black, W. C. (2011). Difluoroethylamines as an amide isostere in inhibitors of cathepsin K. Bioorganic & Medicinal Chemistry Letters, 21(3), 920–923. https://doi.org/10.1016/j.bmcl.2010.12.070
Isabel, Elise, Christophe Mellon, Michael J. Boyd, Nathalie Chauret, Denis Deschênes, Sylvie Desmarais, Jean-Pierre Falgueyret, et al. “Difluoroethylamines as an amide isostere in inhibitors of cathepsin K.” Bioorganic & Medicinal Chemistry Letters 21, no. 3 (February 2011): 920–23. https://doi.org/10.1016/j.bmcl.2010.12.070.
Isabel E, Mellon C, Boyd MJ, Chauret N, Deschênes D, Desmarais S, et al. Difluoroethylamines as an amide isostere in inhibitors of cathepsin K. Bioorganic & medicinal chemistry letters. 2011 Feb;21(3):920–3.
Isabel, Elise, et al. “Difluoroethylamines as an amide isostere in inhibitors of cathepsin K.” Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 3, Feb. 2011, pp. 920–23. Epmc, doi:10.1016/j.bmcl.2010.12.070.
Isabel E, Mellon C, Boyd MJ, Chauret N, Deschênes D, Desmarais S, Falgueyret J-P, Gauthier JY, Khougaz K, Lau CK, Léger S, Levorse DA, Li CS, Massé F, Percival MD, Roy B, Scheigetz J, Thérien M, Truong VL, Wesolowski G, Young RN, Zamboni R, Black WC. Difluoroethylamines as an amide isostere in inhibitors of cathepsin K. Bioorganic & medicinal chemistry letters. 2011 Feb;21(3):920–923.
Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
February 2011
Volume
21
Issue
3
Start / End Page
920 / 923
Related Subject Headings
- Rats
- Protease Inhibitors
- Medicinal & Biomolecular Chemistry
- Ethylamines
- Dogs
- Cathepsin K
- Biphenyl Compounds
- Animals
- Amides
- Administration, Oral