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Preparation and Properties of New Co-Crystals of Ibandronate with Gluco- or Galactopyranoside Derivatives†
Zentiva k.s., U Kabelovny 130, 102 37 Prague 10, Czech Republic
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
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; in revised form: 3 December 2010 / Accepted: 7 December 2010 / Published: 8 December 2010
(This article belongs to the Special Issue ECSOC-13
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
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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.
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(12):8973-8987.
Oktabec, Zbynek; Kos, Jiri; Mandelova, Zuzana; Havelkova, Lenka; Pekarek, Tomas; Rezacova, Anna; Placek, Lukas; Tkadlecova, Marcela; Havlicek, Jaroslav; Dohnal, Jiri; Jampílek, Josef. 2010. "Preparation and Properties of New Co-Crystals of Ibandronate with Gluco- or Galactopyranoside Derivatives." Molecules 15, no. 12: 8973-8987.