Preparation and Properties of New Co-crystals of Ibandronate

Jampílek, Josef; Král, Vladimír; Dohnal, Jiří; Havelková, L.; Kos, Jiří; Plaček, Lukáš; Rezácová, A; Oktabec, Zbynek

doi:10.3390/ecsoc-13-00201

Cited by 5 publications

(3 citation statements)

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“…This is a follow-up paper to our previous works [ 18 , 19 , 20 ] dealing with preparation and characterization of new potential co-crystals of APIs with excipients.…”

Section: Introductionmentioning

confidence: 84%

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

et al. 2010

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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.

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“…This is a follow-up paper to our previous works [ 18 , 19 , 20 ] dealing with preparation and characterization of new potential co-crystals of APIs with excipients.…”

Section: Introductionmentioning

confidence: 84%

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

et al. 2010

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“…The confirmed potential co-crystals would be investigated for their absorption by means of experiments using the Parallel Artificial Membrane Permeation Assay (PAMPA, ) [ 17 ]. This is a follow-up paper to our previous works [ 19 , 20 , 21 , 22 ] dealing with preparation and characterization of new crystalline forms and/or potential co-crystals of APIs with excipients.…”

Section: Introductionmentioning

confidence: 90%

Crystallization Products of Risedronate with Carbohydrates and Their Substituted Derivatives

et al. 2011

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The gastrointestinal absorption of bisphosphonates is in general only about 1%. To address this problem mixtures of risedronate monosodium salt with twelve varied sugar alcohols, furanoses, pyranoses and eight gluco-, manno- and galactopyranoside derivatives as counterions were designed in an effort to prepare co-crystals/new entities with improved intestinal absorption. Crystalline forms were generated by means of kinetically and/or thermodynamically controlled crystallization processes. One hundred and fifty-two prepared samples were screened by means of FT-NIR and FT-Raman spectroscopy. No co-crystal was prepared, but noteworthy results were obtained. A new solid phase of risedronate monosodium salt generated in the presence of phenyl-β-D-galactopyranoside under thermodynamically controlled crystallization conditions was found and also characterized using solid state NMR spectroscopy, X-ray powder diffraction and differential scanning calorimetry. This new polymorph was named as form P. Interactions between risedronate monosodium salt and both carbohydrates were confirmed by means of molecular dynamics simulation. In the present study the relationships between the chemical structures of the studied compounds required for crystalline form change are discussed.

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“…If the 1-aryl group of 2,5-dkps was para-methoxyphenyl (PMP), an oxidative deprotection became feasible, rendering an access to unprotected 2,5-dkps possible (Scheme 6). A prominent example is the 2,5-dkp alaptide for which several pharmacological activities have been reported [41] and which has found widespread applications in dermatology. The (S)-enantiomer 72 of alaptide was readily available from dkp 7 (Scheme 2) by treatment with ceric ammonium nitrate (CAN) in an acetonitrile/water mixture.…”

Section: Angewandte Chemiementioning

confidence: 99%

Creating a Defined Chirality in Amino Acids and Cyclic Dipeptides by Photochemical Deracemization

Großkopf,

Plaza,

Kutta

et al. 2023

Angew Chem Int Ed

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2,5‐Diketopiperazines are cyclic dipeptides displaying a wide range of applications. Their enantioselective preparation has now been found possible from the respective racemates by a photochemical deracemization (53 examples, 74% to quantitative yield, 71‐99% ee). A chiral benzophenone catalyst in concert with irradiation at λ= 366 nm enables to establish the configuration at the stereogenic carbon atom C6 at will. If other stereogenic centers are present in the diketopiperazines they remain unaffected and a stereochemical editing is possible at a single position. Consecutive reactions, including the conversion into N‐aryl or N‐alkyl amino acids or the reduction to piperazines, occur without compromising the newly created stereogenic center. Transient absorption spectroscopy revealed that the benzophenone catalyst processes one enantiomer of the 2,5‐diketopiperazines preferentially and enables a reversible hydrogen atom transfer that is responsible for the deracemization process. The remarkably long lifetime of the protonated ketyl radical implies a yet unprecedented mode of action.

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Preparation and Properties of New Co-crystals of Ibandronate

Cited by 5 publications

References 0 publications

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

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

Crystallization Products of Risedronate with Carbohydrates and Their Substituted Derivatives

Creating a Defined Chirality in Amino Acids and Cyclic Dipeptides by Photochemical Deracemization

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