CA2837784C - Method for manufacturing hydroxyethyl starch derivatives - Google Patents
Method for manufacturing hydroxyethyl starch derivatives Download PDFInfo
- Publication number
- CA2837784C CA2837784C CA2837784A CA2837784A CA2837784C CA 2837784 C CA2837784 C CA 2837784C CA 2837784 A CA2837784 A CA 2837784A CA 2837784 A CA2837784 A CA 2837784A CA 2837784 C CA2837784 C CA 2837784C
- Authority
- CA
- Canada
- Prior art keywords
- iron
- hydroxyethyl starch
- solution
- value
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229920001612 Hydroxyethyl starch Polymers 0.000 title claims abstract description 106
- 229940050526 hydroxyethylstarch Drugs 0.000 title claims abstract description 105
- 238000000034 method Methods 0.000 title claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 235000019426 modified starch Nutrition 0.000 title description 2
- -1 cyanide compound Chemical class 0.000 claims abstract description 25
- 238000010438 heat treatment Methods 0.000 claims abstract description 22
- KWMLJOLKUYYJFJ-UHFFFAOYSA-N 2,3,4,5,6,7-Hexahydroxyheptanoic acid Chemical group OCC(O)C(O)C(O)C(O)C(O)C(O)=O KWMLJOLKUYYJFJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 138
- 229910052742 iron Inorganic materials 0.000 claims description 76
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 14
- 208000015710 Iron-Deficiency Anemia Diseases 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 150000002506 iron compounds Chemical class 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 150000002505 iron Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 5
- 229940126601 medicinal product Drugs 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229920001592 potato starch Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 12
- 229920002472 Starch Polymers 0.000 description 11
- 239000008107 starch Substances 0.000 description 11
- 235000019698 starch Nutrition 0.000 description 11
- 229910021645 metal ion Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 7
- 229920002307 Dextran Polymers 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012482 calibration solution Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000010979 pH adjustment Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- MVZXTUSAYBWAAM-UHFFFAOYSA-N iron;sulfuric acid Chemical compound [Fe].OS(O)(=O)=O MVZXTUSAYBWAAM-UHFFFAOYSA-N 0.000 description 3
- 238000011045 prefiltration Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 238000000108 ultra-filtration Methods 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- FWZTTZUKDVJDCM-CEJAUHOTSA-M disodium;(2r,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron(3+);oxygen(2-);hydroxide;trihydrate Chemical compound O.O.O.[OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Fe+3].[Fe+3].[Fe+3].[Fe+3].[Fe+3].O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 FWZTTZUKDVJDCM-CEJAUHOTSA-M 0.000 description 2
- 229910001447 ferric ion Inorganic materials 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000001631 haemodialysis Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000004698 iron complex Chemical class 0.000 description 2
- 229940032961 iron sucrose Drugs 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- VRIVJOXICYMTAG-IYEMJOQQSA-L iron(ii) gluconate Chemical compound [Fe+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O VRIVJOXICYMTAG-IYEMJOQQSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 102000003951 Erythropoietin Human genes 0.000 description 1
- 108090000394 Erythropoietin Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000987586 Homo sapiens Eosinophil peroxidase Proteins 0.000 description 1
- 101000920686 Homo sapiens Erythropoietin Proteins 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 206010058116 Nephrogenic anaemia Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012897 dilution medium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000028208 end stage renal disease Diseases 0.000 description 1
- 201000000523 end stage renal failure Diseases 0.000 description 1
- 230000010437 erythropoiesis Effects 0.000 description 1
- 229940105423 erythropoietin Drugs 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 229940042644 ferrlecit Drugs 0.000 description 1
- 238000001825 field-flow fractionation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001249 flow field-flow fractionation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 210000003547 hepatic macrophage Anatomy 0.000 description 1
- 102000044890 human EPO Human genes 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- MQBDAEHWGRMADS-XNHLMZCASA-M sodium;(2r,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;iron(3+);oxygen(2-);(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound [O-2].[O-2].[O-2].[Na+].[Fe+3].[Fe+3].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1.O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1.O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1.O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1.O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 MQBDAEHWGRMADS-XNHLMZCASA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229940035081 venofer Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
- C08B31/12—Ethers having alkyl or cycloalkyl radicals substituted by heteroatoms, e.g. hydroxyalkyl or carboxyalkyl starch
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/26—Iron; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
- C08B31/10—Alkyl or cycloalkyl ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/18—Oxidised starch
- C08B31/185—Derivatives of oxidised starch, e.g. crosslinked oxidised starch
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nutrition Science (AREA)
- Obesity (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11170761.8 | 2011-06-21 | ||
| EP11170761A EP2537866A1 (en) | 2011-06-21 | 2011-06-21 | Hydroxyethyl starch derivatives, method for manufacturing the same and therapeutical uses thereof |
| PCT/EP2012/061958 WO2012175608A1 (en) | 2011-06-21 | 2012-06-21 | Method for manufacturing hydroxyethyl starch derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2837784A1 CA2837784A1 (en) | 2012-12-27 |
| CA2837784C true CA2837784C (en) | 2019-10-15 |
Family
ID=44799422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2837784A Active CA2837784C (en) | 2011-06-21 | 2012-06-21 | Method for manufacturing hydroxyethyl starch derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US9181353B2 (enExample) |
| EP (2) | EP2537866A1 (enExample) |
| JP (2) | JP6370217B2 (enExample) |
| CN (2) | CN103649128B (enExample) |
| BR (1) | BR112013032901A2 (enExample) |
| CA (1) | CA2837784C (enExample) |
| CY (1) | CY1121976T1 (enExample) |
| DK (1) | DK2723774T3 (enExample) |
| ES (1) | ES2733767T3 (enExample) |
| HK (1) | HK1220218A1 (enExample) |
| HR (1) | HRP20191173T1 (enExample) |
| HU (1) | HUE044428T2 (enExample) |
| LT (1) | LT2723774T (enExample) |
| MX (1) | MX337682B (enExample) |
| PL (1) | PL2723774T3 (enExample) |
| PT (1) | PT2723774T (enExample) |
| RS (1) | RS59021B1 (enExample) |
| SI (1) | SI2723774T1 (enExample) |
| SM (1) | SMT201900430T1 (enExample) |
| TR (1) | TR201909574T4 (enExample) |
| TW (1) | TWI564010B (enExample) |
| WO (1) | WO2012175608A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6616725B2 (ja) * | 2016-03-31 | 2019-12-04 | 日本製紙株式会社 | 塗工紙用澱粉 |
| AU2020206021B2 (en) | 2019-01-10 | 2025-05-08 | Pharmacosmos Holding A/S | Treating iron deficiency in subjects at risk of cardiovascular adverse events and iron for the management of atrial fibrillation |
| CN114286682A (zh) | 2019-02-09 | 2022-04-05 | 法码科思莫斯控股有限公司 | 治疗具有心血管不良事件风险的个体的铁缺乏以及用于治疗心房颤动的铁 |
| JP2024529536A (ja) | 2021-08-03 | 2024-08-06 | ファーマコスモス ホールディング エー／エス | コンパニオンアニマルの鉄欠乏症の治療における皮下使用のための鉄錯体化合物 |
| CN117547549A (zh) * | 2023-11-09 | 2024-02-13 | 黑龙江八一农垦大学 | 适用于犬arf的腹膜透析液与助清除剂的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3639588A (en) * | 1966-10-22 | 1972-02-01 | Fisons Pharmaceuticals Ltd | Pharmaceutical compositions containing ferric hydroxide complexed with dextran or dextrin heptonic acids |
| US4370476A (en) * | 1979-07-17 | 1983-01-25 | Usher Thomas C | Dextran polycarboxylic acids, ferric hydroxide complexes |
| GB8902894D0 (en) * | 1989-02-09 | 1989-03-30 | Fisons Plc | Compositions |
| JPH0566372A (ja) * | 1991-09-10 | 1993-03-19 | Fukui Megane Kogyo Kk | 金属製眼鏡フレーム部品の製造方法 |
| JPH0776524A (ja) * | 1993-07-13 | 1995-03-20 | Takeda Chem Ind Ltd | 動物用抗貧血剤 |
| DK172860B1 (da) * | 1998-03-25 | 1999-08-16 | Pharmacosmos Holding As | Jerndextranforbindelse til anvendelse som komponent i et terapeutisk middel til forebyggelse af eller behandling af jernman |
| DK173138B1 (da) | 1998-11-20 | 2000-02-07 | Pharmacosmos Holding As | Fremgangsmåde til fremstilling af en jerndextranforbindelse, jerndextranforbindelse fremstillet efter fremgangsmåden, farma |
| EP1762250A1 (en) * | 2005-09-12 | 2007-03-14 | Fresenius Kabi Deutschland GmbH | Conjugates of hydroxyalkyl starch and an active substance, prepared by chemical ligation via thiazolidine |
| WO2009024518A1 (en) * | 2007-08-17 | 2009-02-26 | Akzo Nobel N.V. | Alkali metal salt of glutamic acid n,n-diacetic acid, a process to prepare such salt, and the use thereof |
| TWI469965B (zh) * | 2008-12-22 | 2015-01-21 | Ono Pharmaceutical Co | 乙炔基吲哚化合物 |
| JP5397991B2 (ja) * | 2009-04-01 | 2014-01-22 | 学校法人東京農業大学 | 乳酸菌を用いたビタミンｂ１２の定量方法 |
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- 2012-06-21 PL PL12737229T patent/PL2723774T3/pl unknown
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- 2012-06-21 HR HRP20191173TT patent/HRP20191173T1/hr unknown
- 2012-06-21 DK DK12737229.0T patent/DK2723774T3/da active
- 2012-06-21 SI SI201231627T patent/SI2723774T1/sl unknown
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2016
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| US9631032B2 (en) | 2017-04-25 |
| RS59021B1 (sr) | 2019-08-30 |
| SI2723774T1 (sl) | 2019-08-30 |
| HK1220218A1 (zh) | 2017-04-28 |
| HUE044428T2 (hu) | 2019-10-28 |
| JP2018100424A (ja) | 2018-06-28 |
| TWI564010B (zh) | 2017-01-01 |
| JP6370217B2 (ja) | 2018-08-08 |
| MX2013015075A (es) | 2014-04-14 |
| SMT201900430T1 (it) | 2019-09-09 |
| CN103649128A (zh) | 2014-03-19 |
| CY1121976T1 (el) | 2020-10-14 |
| WO2012175608A1 (en) | 2012-12-27 |
| CA2837784A1 (en) | 2012-12-27 |
| CN105348401A (zh) | 2016-02-24 |
| US20140128594A1 (en) | 2014-05-08 |
| BR112013032901A2 (pt) | 2017-01-24 |
| LT2723774T (lt) | 2019-08-12 |
| US20160046733A1 (en) | 2016-02-18 |
| CN103649128B (zh) | 2016-02-10 |
| MX337682B (es) | 2016-03-15 |
| EP2723774A1 (en) | 2014-04-30 |
| PT2723774T (pt) | 2019-07-15 |
| HRP20191173T1 (hr) | 2019-10-04 |
| PL2723774T3 (pl) | 2019-10-31 |
| US9181353B2 (en) | 2015-11-10 |
| ES2733767T3 (es) | 2019-12-02 |
| TR201909574T4 (en) | 2019-08-21 |
| EP2537866A1 (en) | 2012-12-26 |
| JP2014520188A (ja) | 2014-08-21 |
| DK2723774T3 (da) | 2019-07-15 |
| EP2723774B1 (en) | 2019-04-03 |
| TW201315474A (zh) | 2013-04-16 |
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