Zitieren Sie bitte immer diesen URN: urn:nbn:de:kobv:b43-502825
Insight into the Structure and Properties of Novel Imidazole-Based Salts of Salicylic Acid
- The preparation of new active pharmaceutical ingredient (API) multicomponent Crystal forms, especially co-crystals and salts, is being considered as a reliable strategy to improve API solubility and bioavailability. In this study, three novel imidazole-based salts of the poorly water-soluble salicylic acid (SA) are reported exhibiting a remarkable improvement in solubility and dissolution rate properties. All structures were solved by powder X-ray diffraction. Multiple complementary techniques were used to solve co-crystal/salt ambiguities: density functional Theory calculations, Raman and 1H/13C solid-state NMR spectroscopies. In all molecular salts, the Crystal packing interactions are based on a common charged assisted +N-H SA)...O-(co-former) hydrogen bond interaction. The presence of an extra methyl group in different positions of the co-former, induced different supramolecular arrangements, yielding salts with different physicochemical properties. All salts present much higherThe preparation of new active pharmaceutical ingredient (API) multicomponent Crystal forms, especially co-crystals and salts, is being considered as a reliable strategy to improve API solubility and bioavailability. In this study, three novel imidazole-based salts of the poorly water-soluble salicylic acid (SA) are reported exhibiting a remarkable improvement in solubility and dissolution rate properties. All structures were solved by powder X-ray diffraction. Multiple complementary techniques were used to solve co-crystal/salt ambiguities: density functional Theory calculations, Raman and 1H/13C solid-state NMR spectroscopies. In all molecular salts, the Crystal packing interactions are based on a common charged assisted +N-H SA)...O-(co-former) hydrogen bond interaction. The presence of an extra methyl group in different positions of the co-former, induced different supramolecular arrangements, yielding salts with different physicochemical properties. All salts present much higher solubility and dissolution rate than pure SA. The most promising results were obtained for the salts with imidazole and 1-methylimidazole co-formers.…
Autor*innen: | Inês C.B. Martins, Dominik Al-Sabbagh, Klas MeyerORCiD, Michael MaiwaldORCiD, G. Scholz, Franziska EmmerlingORCiD |
---|---|
Dokumenttyp: | Zeitschriftenartikel |
Veröffentlichungsform: | Verlagsliteratur |
Sprache: | Englisch |
Titel des übergeordneten Werkes (Englisch): | Molecules |
Jahr der Erstveröffentlichung: | 2019 |
Organisationseinheit der BAM: | 1 Analytische Chemie; Referenzmaterialien |
1 Analytische Chemie; Referenzmaterialien / 1.4 Prozessanalytik | |
6 Materialchemie | |
6 Materialchemie / 6.3 Strukturanalytik | |
Veröffentlichende Institution: | Bundesanstalt für Materialforschung und -prüfung (BAM) |
Verlag: | MDPI |
Jahrgang/Band: | 24 |
Ausgabe/Heft: | 22 |
Erste Seite: | 4144 |
DDC-Klassifikation: | Naturwissenschaften und Mathematik / Chemie / Analytische Chemie |
Freie Schlagwörter: | DFT; Imidazole; Powder X-ray diffraction; Salicylic acid; Salts; SsNMR |
Themenfelder/Aktivitätsfelder der BAM: | Chemie und Prozesstechnik |
DOI: | 10.3390/molecules24224144 |
URN: | urn:nbn:de:kobv:b43-502825 |
Verfügbarkeit des Dokuments: | Datei für die Öffentlichkeit verfügbar ("Open Access") |
Lizenz (Deutsch): | Creative Commons - CC BY - Namensnennung 4.0 International |
Datum der Freischaltung: | 27.01.2020 |
Referierte Publikation: | Ja |
Datum der Eintragung als referierte Publikation: | 27.01.2020 |
Schriftenreihen ohne Nummerierung: | Wissenschaftliche Artikel der BAM |