JP4945240B2 - 高分子量鉄サッカリド複合体の合成 - Google Patents
高分子量鉄サッカリド複合体の合成 Download PDFInfo
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- JP4945240B2 JP4945240B2 JP2006515004A JP2006515004A JP4945240B2 JP 4945240 B2 JP4945240 B2 JP 4945240B2 JP 2006515004 A JP2006515004 A JP 2006515004A JP 2006515004 A JP2006515004 A JP 2006515004A JP 4945240 B2 JP4945240 B2 JP 4945240B2
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- Prior art keywords
- ferric
- molecular weight
- iron
- complex
- sugar
- 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.)
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims description 194
- 229910052742 iron Inorganic materials 0.000 title claims description 143
- -1 iron saccharide Chemical class 0.000 title claims description 123
- 230000015572 biosynthetic process Effects 0.000 title claims description 36
- 238000003786 synthesis reaction Methods 0.000 title description 25
- 239000000203 mixture Substances 0.000 claims description 128
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 94
- 235000000346 sugar Nutrition 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 84
- 229960004887 ferric hydroxide Drugs 0.000 claims description 74
- 239000011541 reaction mixture Substances 0.000 claims description 74
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 claims description 73
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 239000005720 sucrose Substances 0.000 claims description 39
- 229930006000 Sucrose Natural products 0.000 claims description 38
- 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 claims description 38
- 238000007792 addition Methods 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 claims description 29
- 239000000176 sodium gluconate Substances 0.000 claims description 29
- 235000012207 sodium gluconate Nutrition 0.000 claims description 29
- 229940005574 sodium gluconate Drugs 0.000 claims description 29
- 239000000084 colloidal system Substances 0.000 claims description 25
- 150000008163 sugars Chemical class 0.000 claims description 25
- 239000002585 base Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 239000000376 reactant Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000002772 monosaccharides Chemical class 0.000 claims description 20
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 17
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 14
- 238000007911 parenteral administration Methods 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 238000000502 dialysis Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000004676 glycans Chemical class 0.000 claims description 10
- 229920001542 oligosaccharide Polymers 0.000 claims description 10
- 150000002482 oligosaccharides Chemical class 0.000 claims description 10
- 229920001282 polysaccharide Polymers 0.000 claims description 10
- 239000005017 polysaccharide Substances 0.000 claims description 10
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 9
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- 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 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- 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 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 238000004108 freeze drying Methods 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 claims description 3
- 238000001694 spray drying Methods 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000012431 aqueous reaction media Substances 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 229960002413 ferric citrate Drugs 0.000 claims description 2
- YPJCVYYCWSFGRM-UHFFFAOYSA-H iron(3+);tricarbonate Chemical compound [Fe+3].[Fe+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O YPJCVYYCWSFGRM-UHFFFAOYSA-H 0.000 claims description 2
- NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims 3
- GZCGUPFRVQAUEE-VANKVMQKSA-N aldehydo-L-glucose Chemical group OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-VANKVMQKSA-N 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 150000002303 glucose derivatives Chemical class 0.000 claims 1
- 239000000017 hydrogel Substances 0.000 claims 1
- 230000003068 static effect Effects 0.000 claims 1
- 150000003445 sucroses Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 60
- 239000000243 solution Substances 0.000 description 51
- 150000001720 carbohydrates Chemical class 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 31
- 239000000126 substance Substances 0.000 description 29
- 230000003394 haemopoietic effect Effects 0.000 description 25
- 238000003756 stirring Methods 0.000 description 23
- 230000008569 process Effects 0.000 description 21
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 19
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 19
- 229960001031 glucose Drugs 0.000 description 19
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 18
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 241000894007 species Species 0.000 description 16
- 229940032296 ferric chloride Drugs 0.000 description 15
- 238000005755 formation reaction Methods 0.000 description 15
- 239000008103 glucose Substances 0.000 description 14
- 239000003085 diluting agent Substances 0.000 description 13
- 229910001447 ferric ion Inorganic materials 0.000 description 13
- 239000006227 byproduct Substances 0.000 description 12
- 230000008859 change Effects 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 229920002307 Dextran Polymers 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 10
- 238000009826 distribution Methods 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 238000002356 laser light scattering Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 241000282412 Homo Species 0.000 description 9
- 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 9
- 230000000694 effects Effects 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical group OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 239000003173 antianemic agent Substances 0.000 description 8
- 235000014633 carbohydrates Nutrition 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000000569 multi-angle light scattering Methods 0.000 description 8
- 229940062350 sodium ferric gluconate complex Drugs 0.000 description 8
- 238000004448 titration Methods 0.000 description 8
- 150000001323 aldoses Chemical class 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000000149 argon plasma sintering Methods 0.000 description 7
- 235000010350 erythorbic acid Nutrition 0.000 description 7
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- 239000002245 particle Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
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- 229940124597 therapeutic agent Drugs 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000002016 disaccharides Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 150000002505 iron Chemical class 0.000 description 6
- YHGPYBQVSJBGHH-UHFFFAOYSA-H iron(3+);trisulfate;pentahydrate Chemical compound O.O.O.O.O.[Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YHGPYBQVSJBGHH-UHFFFAOYSA-H 0.000 description 6
- 229940026239 isoascorbic acid Drugs 0.000 description 6
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- 238000006467 substitution reaction Methods 0.000 description 6
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- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
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- 239000011888 foil Substances 0.000 description 5
- 239000000174 gluconic acid Substances 0.000 description 5
- 235000012208 gluconic acid Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000012266 salt solution Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 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 5
- 238000004611 spectroscopical analysis Methods 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
- 102000001554 Hemoglobins Human genes 0.000 description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- 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 class 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 4
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- QUIAVNOOCZTWEL-AGRODQNPSA-K iron(3+);(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate;trihydrate Chemical compound O.O.O.[Fe+3].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.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O QUIAVNOOCZTWEL-AGRODQNPSA-K 0.000 description 4
- 150000002584 ketoses Chemical group 0.000 description 4
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
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- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
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- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
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- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
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- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
Landscapes
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- Hematology (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US47465203P | 2003-05-30 | 2003-05-30 | |
| US60/474,652 | 2003-05-30 | ||
| PCT/US2004/016866 WO2005000210A2 (en) | 2003-05-30 | 2004-05-28 | Synthesis of high molecular weight iron-saccharidic complexes |
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| JP2011244615A Division JP2012082199A (ja) | 2003-05-30 | 2011-11-08 | 高分子量鉄サッカリド複合体の合成 |
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| JP2006526643A JP2006526643A (ja) | 2006-11-24 |
| JP2006526643A5 JP2006526643A5 (enExample) | 2007-07-12 |
| JP4945240B2 true JP4945240B2 (ja) | 2012-06-06 |
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| JP2006515004A Expired - Fee Related JP4945240B2 (ja) | 2003-05-30 | 2004-05-28 | 高分子量鉄サッカリド複合体の合成 |
| JP2011244615A Pending JP2012082199A (ja) | 2003-05-30 | 2011-11-08 | 高分子量鉄サッカリド複合体の合成 |
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| EP1997833A1 (de) * | 2007-05-29 | 2008-12-03 | Vifor (International) Ag | Wasserlösliche Eisen-Kohlenhydratderivat-Komplexe, deren Herstellung und diese enthaltende Arzneimittel |
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| KR101141410B1 (ko) * | 2009-10-23 | 2012-05-04 | 국립암센터 | 광감각제 - 금속나노입자 전하 복합체 및 이를 함유하는 광역학 치료 또는 진단을 위한 조성물 |
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| CN104892782A (zh) * | 2015-05-05 | 2015-09-09 | 农业部规划设计研究院 | 低聚糖醛酸钙及其制备方法和在植物营养剂中的应用 |
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2004
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- 2004-05-28 EP EP04776157.2A patent/EP1628986B1/en not_active Expired - Lifetime
- 2004-05-28 WO PCT/US2004/016866 patent/WO2005000210A2/en not_active Ceased
- 2004-05-28 CN CNA2004800149881A patent/CN1798754A/zh active Pending
- 2004-05-28 JP JP2006515004A patent/JP4945240B2/ja not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2012082199A (ja) | 2012-04-26 |
| CN1798754A (zh) | 2006-07-05 |
| WO2005000210A2 (en) | 2005-01-06 |
| US8691776B2 (en) | 2014-04-08 |
| BRPI0410830A (pt) | 2006-06-27 |
| CA2526771C (en) | 2011-04-12 |
| CA2526771A1 (en) | 2005-01-06 |
| WO2005000210A3 (en) | 2005-09-15 |
| AU2004251625B2 (en) | 2011-10-27 |
| IL172225A0 (en) | 2011-08-01 |
| EP1628986A2 (en) | 2006-03-01 |
| AU2004251625A1 (en) | 2005-01-06 |
| JP2006526643A (ja) | 2006-11-24 |
| US20110220539A1 (en) | 2011-09-15 |
| EP1628986A4 (en) | 2010-12-01 |
| US20050037996A1 (en) | 2005-02-17 |
| US7964568B2 (en) | 2011-06-21 |
| EP1628986B1 (en) | 2013-04-24 |
| IL172225A (en) | 2013-10-31 |
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