NO132521B - - Google Patents
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- Publication number
- NO132521B NO132521B NO356972A NO356972A NO132521B NO 132521 B NO132521 B NO 132521B NO 356972 A NO356972 A NO 356972A NO 356972 A NO356972 A NO 356972A NO 132521 B NO132521 B NO 132521B
- Authority
- NO
- Norway
- Prior art keywords
- iron
- minutes
- added
- solution
- polymer
- Prior art date
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 616
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 374
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 233
- 239000000243 solution Substances 0.000 claims description 231
- 229920000642 polymer Polymers 0.000 claims description 220
- 229910052742 iron Inorganic materials 0.000 claims description 183
- 238000002360 preparation method Methods 0.000 claims description 117
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 109
- 239000000203 mixture Substances 0.000 claims description 94
- 229910001868 water Inorganic materials 0.000 claims description 79
- 239000002244 precipitate Substances 0.000 claims description 67
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 53
- 239000000600 sorbitol Substances 0.000 claims description 53
- 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 claims description 51
- 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 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 36
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 34
- 238000001035 drying Methods 0.000 claims description 34
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 32
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 25
- 239000000174 gluconic acid Substances 0.000 claims description 25
- 235000012208 gluconic acid Nutrition 0.000 claims description 25
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 24
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- 239000004310 lactic acid Substances 0.000 claims description 16
- 235000014655 lactic acid Nutrition 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 15
- 238000001556 precipitation Methods 0.000 claims description 15
- 150000005846 sugar alcohols Polymers 0.000 claims description 15
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000004698 iron complex Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000002596 lactones Chemical class 0.000 claims description 11
- 150000002506 iron compounds Chemical class 0.000 claims description 9
- 239000012670 alkaline solution Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- -1 iron (II) compound Chemical class 0.000 claims description 6
- 238000007911 parenteral administration Methods 0.000 claims description 6
- 241000282414 Homo sapiens Species 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229920000223 polyglycerol Polymers 0.000 claims description 5
- QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 claims description 4
- XGGLLRJQCZROSE-UHFFFAOYSA-K ammonium iron(iii) sulfate Chemical compound [NH4+].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XGGLLRJQCZROSE-UHFFFAOYSA-K 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 description 2
- 229940079593 drug Drugs 0.000 claims 1
- 229920003169 water-soluble polymer Polymers 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 351
- 239000012071 phase Substances 0.000 description 177
- 239000012153 distilled water Substances 0.000 description 151
- 238000003756 stirring Methods 0.000 description 122
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 120
- 238000007792 addition Methods 0.000 description 71
- 239000000706 filtrate Substances 0.000 description 50
- 238000002347 injection Methods 0.000 description 50
- 239000007924 injection Substances 0.000 description 50
- 239000012452 mother liquor Substances 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 32
- 238000000926 separation method Methods 0.000 description 32
- 238000005406 washing Methods 0.000 description 30
- 238000006116 polymerization reaction Methods 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 241000283973 Oryctolagus cuniculus Species 0.000 description 24
- 239000007788 liquid Substances 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 22
- 230000004580 weight loss Effects 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 239000012467 final product Substances 0.000 description 17
- 239000011780 sodium chloride Substances 0.000 description 17
- 239000006188 syrup Substances 0.000 description 17
- 235000020357 syrup Nutrition 0.000 description 17
- 239000011734 sodium Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- 239000003381 stabilizer Substances 0.000 description 13
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 12
- 210000003205 muscle Anatomy 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 230000037396 body weight Effects 0.000 description 11
- 229940082629 iron antianemic preparations Drugs 0.000 description 11
- 229960004592 isopropanol Drugs 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 239000004375 Dextrin Substances 0.000 description 10
- 229920001353 Dextrin Polymers 0.000 description 10
- 238000002523 gelfiltration Methods 0.000 description 10
- 230000029142 excretion Effects 0.000 description 9
- 238000010255 intramuscular injection Methods 0.000 description 9
- 239000012528 membrane Substances 0.000 description 9
- 231100000419 toxicity Toxicity 0.000 description 9
- 230000001988 toxicity Effects 0.000 description 9
- 210000002700 urine Anatomy 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 239000000908 ammonium hydroxide Substances 0.000 description 8
- 239000007927 intramuscular injection Substances 0.000 description 8
- 235000019425 dextrin Nutrition 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- WNDUPUMWHYAJOR-SADXPQEKSA-K (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+) Chemical compound [Fe+3].OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WNDUPUMWHYAJOR-SADXPQEKSA-K 0.000 description 5
- 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 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 238000007918 intramuscular administration Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000012985 polymerization agent Substances 0.000 description 5
- 239000000176 sodium gluconate Substances 0.000 description 5
- 235000012207 sodium gluconate Nutrition 0.000 description 5
- 229940005574 sodium gluconate Drugs 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920002307 Dextran Polymers 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- MVZXTUSAYBWAAM-UHFFFAOYSA-N iron;sulfuric acid Chemical compound [Fe].OS(O)(=O)=O MVZXTUSAYBWAAM-UHFFFAOYSA-N 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IIGSLJHOCDIPJX-HFYYSOHNSA-N OCCCC(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO Chemical compound OCCCC(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IIGSLJHOCDIPJX-HFYYSOHNSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- MSNWSDPPULHLDL-UHFFFAOYSA-K ferric hydroxide Chemical compound [OH-].[OH-].[OH-].[Fe+3] MSNWSDPPULHLDL-UHFFFAOYSA-K 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 150000002505 iron Chemical class 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
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011045 prefiltration Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AKSVALRPYDVQBS-CABCVRRESA-N 2-[(3R)-3-[1-[1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-3-(trifluoromethyl)pyrazolo[3,4-b]pyrazin-6-yl]azetidin-3-yl]piperidin-1-yl]ethanol Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)N1CC(C1)[C@@H]1CN(CCC1)CCO)C(F)(F)F AKSVALRPYDVQBS-CABCVRRESA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- FPFSGDXIBUDDKZ-UHFFFAOYSA-N 3-decyl-2-hydroxycyclopent-2-en-1-one Chemical compound CCCCCCCCCCC1=C(O)C(=O)CC1 FPFSGDXIBUDDKZ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010022971 Iron Deficiencies Diseases 0.000 description 1
- 101100042258 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) sem-1 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000016127 added sugars Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- FGFCSHCXBYAKOL-UHFFFAOYSA-N cyclohexane-1,1,2,2,3,3-hexol Chemical class OC1(O)CCCC(O)(O)C1(O)O FGFCSHCXBYAKOL-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229960002428 fentanyl Drugs 0.000 description 1
- IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 150000004001 inositols Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-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
- 229940029416 iron-dextran complex Drugs 0.000 description 1
- 210000001365 lymphatic vessel Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical class COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A61K31/295—Iron group metal compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyethers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO741978A NO134095C (https=) | 1971-10-06 | 1974-05-31 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE12613/71A SE359447B (https=) | 1971-10-06 | 1971-10-06 | |
| SE12614/71A SE356754B (https=) | 1971-10-06 | 1971-10-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132521B true NO132521B (https=) | 1975-08-18 |
| NO132521C NO132521C (https=) | 1975-11-26 |
Family
ID=26655894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO356972A NO132521C (https=) | 1971-10-06 | 1972-10-05 |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS4861611A (https=) |
| AR (1) | AR199188A1 (https=) |
| BE (1) | BE789758A (https=) |
| CA (1) | CA991544A (https=) |
| CH (1) | CH590891A5 (https=) |
| CS (1) | CS178876B2 (https=) |
| CY (1) | CY917A (https=) |
| DD (1) | DD105722A5 (https=) |
| DE (1) | DE2247021C3 (https=) |
| ES (1) | ES407332A1 (https=) |
| FI (1) | FI49475C (https=) |
| FR (1) | FR2157831B1 (https=) |
| GB (1) | GB1411266A (https=) |
| HU (2) | HU165476B (https=) |
| IE (2) | IE37761B1 (https=) |
| KE (1) | KE2757A (https=) |
| MY (1) | MY7800008A (https=) |
| NL (1) | NL162943C (https=) |
| NO (1) | NO132521C (https=) |
| SU (1) | SU730276A3 (https=) |
| TR (1) | TR17725A (https=) |
-
0
- BE BE789758D patent/BE789758A/xx unknown
-
1972
- 1972-09-25 DE DE19722247021 patent/DE2247021C3/de not_active Expired
- 1972-09-26 CH CH1402072A patent/CH590891A5/xx not_active IP Right Cessation
- 1972-10-03 SU SU721833676A patent/SU730276A3/ru active
- 1972-10-04 HU HUAA000754 patent/HU165476B/hu unknown
- 1972-10-04 AR AR24446072A patent/AR199188A1/es active
- 1972-10-04 HU HUAA000712 patent/HU164864B/hu unknown
- 1972-10-05 IE IE94272A patent/IE37761B1/xx unknown
- 1972-10-05 GB GB4607472A patent/GB1411266A/en not_active Expired
- 1972-10-05 IE IE135172A patent/IE37760B1/xx unknown
- 1972-10-05 CA CA153,317A patent/CA991544A/en not_active Expired
- 1972-10-05 CS CS673572A patent/CS178876B2/cs unknown
- 1972-10-05 FI FI275072A patent/FI49475C/fi active
- 1972-10-05 FR FR7235393A patent/FR2157831B1/fr not_active Expired
- 1972-10-05 NO NO356972A patent/NO132521C/no unknown
- 1972-10-05 CY CY91772A patent/CY917A/xx unknown
- 1972-10-05 NL NL7213482A patent/NL162943C/xx not_active IP Right Cessation
- 1972-10-05 DD DD16604672A patent/DD105722A5/xx unknown
- 1972-10-05 JP JP9949872A patent/JPS4861611A/ja active Pending
- 1972-10-06 TR TR1772572A patent/TR17725A/xx unknown
-
1975
- 1975-03-31 ES ES407332A patent/ES407332A1/es not_active Expired
-
1977
- 1977-08-16 KE KE275777A patent/KE2757A/xx unknown
-
1978
- 1978-12-30 MY MY7800008A patent/MY7800008A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA991544A (en) | 1976-06-22 |
| FI49475B (https=) | 1975-04-01 |
| MY7800008A (en) | 1978-12-31 |
| KE2757A (en) | 1977-10-14 |
| NL162943C (nl) | 1980-07-15 |
| DD105722A5 (https=) | 1974-05-12 |
| FI49475C (fi) | 1975-07-10 |
| CS178876B2 (en) | 1977-10-31 |
| AR199188A1 (es) | 1974-08-14 |
| JPS4861611A (https=) | 1973-08-29 |
| DE2247021A1 (de) | 1973-04-12 |
| ES407332A1 (es) | 1976-01-16 |
| HU164864B (https=) | 1974-05-28 |
| FR2157831A1 (https=) | 1973-06-08 |
| NO132521C (https=) | 1975-11-26 |
| HU165476B (https=) | 1974-09-28 |
| IE37761L (en) | 1973-04-06 |
| IE37760L (en) | 1973-04-06 |
| GB1411266A (en) | 1975-10-22 |
| FR2157831B1 (https=) | 1976-04-23 |
| CH590891A5 (https=) | 1977-08-31 |
| IE37761B1 (en) | 1977-10-12 |
| CY917A (en) | 1977-12-23 |
| TR17725A (tr) | 1975-07-23 |
| NL7213482A (https=) | 1973-04-10 |
| IE37760B1 (en) | 1977-10-12 |
| DE2247021C3 (de) | 1979-08-16 |
| SU730276A3 (ru) | 1980-04-25 |
| NL162943B (nl) | 1980-02-15 |
| DE2247021B2 (de) | 1978-12-14 |
| BE789758A (fr) | 1973-04-06 |
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