US 12,130,296 B2
Method for the direct detection and/or quantification of at least one compound with a molecular weight of at least 200
Joan Perello Bestard, Palma de Mallorca (ES); Ciriaco Maraschiello De Zuani, Barcelona (ES); Irene Lentheric, Barcelona (ES); Paula Mendoza De Las Heras, Barcelona (ES); Fernando Tur Espinosa, Palma de Mallorca (ES); Eva Tur Tur, Palma de Mallorca (ES); Maximo Encabo Alarcon, Barcelona (ES); Eva Martin Becerra, Palma de Mallorca (ES); Maria de Mar Benito Amengual, Palma de Mallorca (ES); and Bernat Isern Amengual, Palma de Mallorca (ES)
Assigned to SANIFIT THERAPEUTICS S.A., Palma de Mallorca (ES)
Filed by SANIFIT THERAPEUTICS S.A., Palma (ES)
Filed on Oct. 28, 2021, as Appl. No. 17/513,568.
Application 15/436,202 is a division of application No. 14/350,265, granted, now 9,612,250, issued on Apr. 4, 2017, previously published as PCT/EP2012/069878, filed on Oct. 8, 2012.
Application 17/513,568 is a continuation of application No. 15/436,202, filed on Feb. 17, 2017, granted, now 11,162,958.
Claims priority of application No. 11382314 (EP), filed on Oct. 6, 2011.
Prior Publication US 2022/0187326 A1, Jun. 16, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. G01N 33/94 (2006.01); C07K 1/18 (2006.01); G01N 33/50 (2006.01); G01N 33/53 (2006.01)
CPC G01N 33/94 (2013.01) [C07K 1/18 (2013.01); G01N 33/50 (2013.01); G01N 33/5005 (2013.01); G01N 33/5308 (2013.01); G01N 2496/00 (2013.01); G01N 2560/00 (2013.01); Y10T 436/163333 (2015.01)] 23 Claims
 
1. A method for analyzing a composition comprising a phosphorus containing compound having a molecular weight of at least 200 daltons, wherein the method comprises
(i) introducing at least one standard sample together or sequentially with a test sample comprising the composition comprising a phosphorus containing compound together with its impurities into a stream of a solvent system, wherein the solvent system is a polar solvent comprising potassium hydroxide (KOH) or a solvent mixture comprising at least one polar solvent comprising KOH, and,
(ii) passing the standard sample and test sample through a single anion-exchange chromatography column containing particles of a cross-linked polystyrene resin, wherein the test sample comprises a solution or a slurry containing the composition comprising the phosphorus containing compound, and wherein the amount of phosphorus containing compound in the composition is above 60% by weight;
wherein the phosphorus containing compound is selected from:
(a) bisphosphonate or polyphosphonate;
(b) a hexametaphosphate;
(c) a C3-C7 cycloalkyl substituted compound with at least two —R groups wherein each —R group is —OH, —OP(O)(OH)2 or —P(O)(OH)2, and wherein at least two —R groups are independently selected from —P(O)(OH)2 and —OP(O)(OH)2 and said C3-C7 cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or cycloheptyl;
(d) ions or salts thereof, or,
(e) a combination thereof.