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US 9,169,279 B2Granted
Crystallization method and bioavailability
AssigneeThar Pharmaceuticals, Inc.
InventorsMazen Hanna, Ning Shan, Miranda L. Cheney, David R. Weyna, Raymond Houck
Life of this patent
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Abstract
Preparation and in vitro and in vivo characterization of novel forms of active pharmaceutical ingredients, suitable for pharmaceutical compositions in drug delivery systems for humans.
Claims9
A composition comprising at least one API and at least one coformer:
- wherein said at least one coformer is a molecular complex coformer and/or an additional coformer;
- wherein said API and said molecular complex coformer form a molecular complex;
- wherein said API is a bisphosphonic acid and said at least one coformer is selected from the group consisting of sodium, ammonium, ammonia, lysine, nicotinamide, adenine, and glycine;
- and
- wherein said molecular complex is a crystalline molecular complex selected from the group consisting of:
- a) a crystalline zoledronic acid, sodium zoledronate and water molecular complex characterized by an X-ray powder diffraction pattern having peaks at about 8.1, 13.3, 21.5, 24.6, and 25.6±0.2 degrees two-theta;
- b) a crystalline ammonium zoledronic acid salt and water molecular complex characterized by an X-ray powder diffraction pattern having strong peaks at about 11.0, 14.6, 15.4, 19.9, and 29.4±0.2 degrees two-theta;
- c) a crystalline zoledronic diammonia water molecular complex characterized by an X-ray powder diffraction pattern having strong peaks at about 12.2, 13.0, 14.1, 17.1, and 19.3±0.2 degrees two-theta;
- d) a crystalline zoledronic acid, L-lysine, and water molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 9.0, 14.4, 18.1, 26.0, and 29.6±0.2 degrees two-theta;
- e) a crystalline zoledronic acid, L-lysine, and water molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 9.6, 10.7, 14.3, 21.4, 23.5±0.2 degrees two-theta;
- f) a crystalline zoledronic acid DL-lysine and water molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 8.3, 11.8, 12.3, 15.8, and 20.8±0.2 degrees two-theta;
- g) a crystalline zoledronic acid, DL-lysine, and water molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 9.1, 14.7, 18.0, 21.2, and 26.0±0.2 degrees two-theta;
- h) a crystalline zoledronic acid, DL-lysine, and water molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 9.7, 10.8, 14.4, 18.9, 21.4±0.2 degrees two-theta;
- i) a crystalline zoledronic acid, zoledronic, DL-lysine, ethanol, and water complex characterized by an X-ray powder diffraction pattern comprising peaks at about 8.8, 9.7, 17.6, 23.1, and 26.5±0.2 degrees two-theta;
- j) a crystalline zoledronic acid, adenine, and water molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 13.6, 15.9, 19.7, 27.9, and 29.5±0.2 degrees two-theta;
- k) a crystalline zoledronic acid, nicotinamide, and water molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 13.1, 15.2, 21.0, 23.9, and 26.5±0.2 degrees two-theta;
- and
- l) a crystalline zoledronic acid and glycine molecular complex characterized by an X-ray powder diffraction pattern comprising peaks at about 10.2, 17.8, 19.9, 22.9, and 28.1±0.2 degrees two-theta.
15 more elements
Dependencies are inferred from the claim text.