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Molecules 2010, 15(12), 8973-8987; https://doi.org/10.3390/molecules15128973

Preparation and Properties of New Co-Crystals of Ibandronate with Gluco- or Galactopyranoside Derivatives

1
Zentiva k.s., U Kabelovny 130, 102 37 Prague 10, Czech Republic
2
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
3
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
Preliminary results were presented at the Thirteenth Electronic Conference on Synthetic Organic Chemistry (ECSOC-13, http://www.sciforum.net/presentation/201), 1-30 November 2009
*
Author to whom correspondence should be addressed.
Received: 22 November 2010 / Revised: 3 December 2010 / Accepted: 7 December 2010 / Published: 8 December 2010
(This article belongs to the Special Issue ECSOC-13)
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Abstract

Mixtures of ibandronate monosodium salt with eleven gluco- and/or galacto-pyranoside derivatives as counterions were designed to prepare co-crystals with improved intestinal absorption. In general, gastrointestinal absorption of bisphosphonates after oral administration is approximately 1%. Co-crystals were generated by means of thermodynamically and/or kinetically controlled crystallization processes. Seventy-seven prepared samples were analyzed by means of FT-NIR, FT-Raman spectrometry and solid state NMR spectroscopy. New entities of ibandronate monosodium salt with phenyl-β-d-galactopyranoside were found and characterized. The absorption of these potential new co-crystals was investigated by means of PAMPA experiments. In the present study the relationships between the chemical structures of the studied compounds required for co-crystal generation are discussed.
Keywords: ibandronate; d-glucopyranosides; d-galactopyranosides; co-crystals; FT-NIR; FT-Raman; CP/MAS NMR; PAMPA ibandronate; d-glucopyranosides; d-galactopyranosides; co-crystals; FT-NIR; FT-Raman; CP/MAS NMR; PAMPA
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Oktabec, Z.; Kos, J.; Mandelova, Z.; Havelkova, L.; Pekarek, T.; Rezacova, A.; Placek, L.; Tkadlecova, M.; Havlicek, J.; Dohnal, J.; Jampílek, J. Preparation and Properties of New Co-Crystals of Ibandronate with Gluco- or Galactopyranoside Derivatives. Molecules 2010, 15, 8973-8987.

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