# US 10,865,255 B2 · Stable iron oligosaccharide compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,865,255 B2 - Document ID: US10865255B2 - Status: Granted - Kind: B2 - Application number: 15/222,306 - Filed: 2016-07-28 - Published: 2016-11-17 - Granted: 2020-12-15 - Earliest claimed: 2014-06-18 - Assignees: Pharmacosmos Holding A/S - Applicants: Pharmacosmos Holding A/S - Inventors: Hans Andreasen - Web page: https://patentgrep.com/patent/US10865255B2 ## CPC - C08B 37/0021: {Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran} - A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)} - A61K 31/721: Dextrans - A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin - A61P 3/02: Nutrients, e.g. vitamins, minerals - A61P 7/06: Antianaemics - C07H 3/06: Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages - C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13) ## Abstract The invention relates to an iron oligosaccharide compound with improved stability comprising a hydrogenated oligosaccharide in stable association with ferric oxyhydroxide, the content of dimer saccharide in said hydrogenated oligosaccharide being 2.9% by weight or less, based on the total weight of the hydrogenated oligosaccharide. In further aspects is provided a process for preparing said compound as well as the use of said compound for preparation of a composition for treatment of iron deficiency anaemia. ## Claims ### Claim 1 A process for preparing a mixture of hydrogenated dextran oligosaccharides, comprising: (a) hydrolysing a polysaccharide so as to reduce its molecular weight, (b) fractioning the oligosaccharide of (a) according to molecular weight, the fractioning including a procedure of purification, which procedure is continued until the content of dimer saccharide in the purified fraction of oligosaccharide has been reduced to 2.9% by weight or less, based on the total weight of the oligosaccharide, and hydrogenating the oligosaccharide resulting from step (a) or step (b) wherein said oligosaccharide produced in step (b) comprises a mixture of hydrogenated dextran oligosaccharides having the following molecular weight distribution: (i) a weight average molecular weight (Mw) between 500 and 3,000 Daltons, (ii) a number average molecular weight (Mn) above 500 Daltons; (iii) 90% by weight of said hydrogenated dextran oligosaccharides have molecular weights of less than 3,500 Daltons, and (iv) the Mw of the 10% by weight fraction containing the hydrogenated dextran oligosaccharides having the highest molecular weights is below 4,500 Daltons. ### Claim 2 (depends on 1) The process according to claim 1, wherein said purification is continued until the monomer saccharide content in the purified fraction of oligosaccharide has been reduced to 0.5% by weight or less, based on the total weight of the oligosaccharide. ### Claim 3 (depends on 1) A composition comprising a hydrogenated oligosaccharide obtained by the process according to claim 1 and further comprising at least one pharmaceutically acceptable carrier. ### Claim 4 (depends on 2) A hydrogenated oligosaccharide obtained by the process according to claim 2. ### Claim 5 (depends on 1) The process according to claim 1, wherein said procedure of purification is chromatography. ### Claim 6 (depends on 1) The process according to claim 1, wherein said procedure of purification is a membrane process. ### Claim 7 (depends on 6) The process according to claim 6, wherein said membrane process has a cut-off value of between 340 and 800 Daltons. ### Claim 8 (depends on 1) The process according to claim 1, which comprises hydrogenating the oligosaccharide resulting from step (a). ### Claim 9 (depends on 1) The process according to claim 1, which comprises hydrogenating the oligosaccharide resulting from step (b). ### Claim 10 (depends on 1) The process according to claim 1, further comprising sterilizing said mixture of hydrogenated dextran oligosaccharides by autoclaving. ### Claim 11 (depends on 1) The process according to claim 1, wherein the Mw of said mixture of hydrogenated dextran oligosaccharides is 1,600 Daltons or less. ### Claim 12 (depends on 1) The process according to claim 1, wherein the Mn of said mixture of hydrogenated dextran oligosaccharides is 1,600 Daltons or less. ### Claim 13 (depends on 1) The process according to claim 1, wherein 90% by weight of the hydrogenated dextran oligosaccharides in said mixture of hydrogenated dextran oligosaccharides have molecular weights of less than 2,700 Daltons. ### Claim 14 (depends on 1) The process according to claim 1, wherein the Mw of the 10% by weight fraction containing the hydrogenated dextran oligosaccharides having the highest molecular weights in said mixture of hydrogenated dextran oligosaccharides is below 3,200 Daltons. ### Claim 15 (depends on 1) The process according to claim 1, wherein said purification is continued until the monomer saccharide content in the purified fraction of oligosaccharide has been reduced to 2.5% by weight or less, based on the total weight of the oligosaccharide. ### Claim 16 (depends on 1) The process according to claim 1, wherein said purification is continued until the monomer saccharide content in the purified fraction of oligosaccharide has been reduced to 2.3% by weight or less, based on the total weight of the oligosaccharide. ### Claim 17 A process for preparing a mixture of hydrogenated dextran oligosaccharides, comprising: (a) hydrolysing a polysaccharide so as to reduce its molecular weight, (b) fractioning the oligosaccharide of (a) according to molecular weight, the fractioning including a procedure of purification, which procedure is continued until the content of dimer saccharide in the purified fraction of oligosaccharide has been reduced to 2.3% by weight or less, based on the total weight of the oligosaccharide, and hydrogenating the oligosaccharide resulting from step (a) or step (b), wherein said oligosaccharide produced in step (b) comprises a mixture of hydrogenated dextran oligosaccharides having the following molecular weight distribution: (i) a weight average molecular weight (Mw) between 500 and 1,600 Daltons, (ii) a number average molecular weight (Mn) is above 500 Daltons, (iii) 90% by weight of said hydrogenated dextran oligosaccharides have molecular weights of less than 2,700 Daltons, (iv) the Mw of the 10% by weight fraction of the hydrogenated dextran oligosaccharides having the highest molecular weights is below 3,200 Daltons, and (vi) the content of monomer saccharide in said hydrogenated oligosaccharide is 0.5% by weight or less, based on the total weight of the hydrogenated oligosaccharide. ### Claim 18 (depends on 17) The process according to claim 17, wherein said procedure of purification is chromatography. ### Claim 19 (depends on 17) The process according to claim 17, wherein said procedure of purification is a membrane process. ### Claim 20 (depends on 19) The process according to claim 19, wherein said membrane process has a cut-off value of between 340 and 800 Daltons. ### Claim 21 (depends on 17) The process according to claim 17, which comprises hydrogenating the oligosaccharide resulting from step (a). ### Claim 22 (depends on 17) The process according to claim 17, which comprises hydrogenating the oligosaccharide resulting from step (b). ### Claim 23 (depends on 17) The process according to claim 17, wherein the Mw of said oligosaccharide is approximately 1,000 Daltons. ### Claim 24 (depends on 17) The process according to claim 17, further comprising sterilizing said mixture of hydrogenated dextran oligosaccharides by autoclaving. ### Claim 25 (depends on 17) The process according to claim 17, wherein the Mw of said mixture of hydrogenated dextran oligosaccharides is 1,600 Daltons or less. ### Claim 26 (depends on 17) The process according to claim 17, wherein the Mn of said mixture of hydrogenated dextran oligosaccharides is 1,600 Daltons or less. ### Claim 27 (depends on 17) The process according to claim 17, wherein 90% by weight of the hydrogenated dextran oligosaccharides in said mixture of hydrogenated dextran oligosaccharides have molecular weights of less than 2,700 Daltons. ### Claim 28 (depends on 17) The process according to claim 17, wherein the Mw of the 10% by weight fraction containing the hydrogenated dextran oligosaccharides having the highest molecular weights in said mixture of hydrogenated dextran oligosaccharides is below 3,200 Daltons.