NO132521B - - Google Patents

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Info

Publication number: NO132521B
Authority: NO; Norway
Prior art keywords: iron; minutes; added; solution; polymer
Prior art date: 1971-10-06

Application number

NO356972A

Other languages

English (en)

Norwegian (no)

Other versions

NO132521C (xx

Inventor

A-G Dahlberg

K-G Hoegberg

S Lindvall

T O V Rydh

Original Assignee

Astra Laekemedel Ab

Priority date (The priority date 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 date listed.)

1971-10-06

Filing date

1972-10-05

Publication date

1975-08-18

1971-10-06 Priority claimed from SE12614/71A external-priority patent/SE356754B/xx

1971-10-06 Priority claimed from SE12613/71A external-priority patent/SE359447B/xx

1972-10-05 Application filed by Astra Laekemedel Ab filed Critical Astra Laekemedel Ab

1974-05-31 Priority to NO741978A priority Critical patent/NO134095C/no

1975-08-18 Publication of NO132521B publication Critical patent/NO132521B/no

1975-11-26 Publication of NO132521C publication Critical patent/NO132521C/no

Links

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)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Polyethers (AREA)

NO356972A 1971-10-06 1972-10-05 NO132521C (xx)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO741978A NO134095C (xx)	1971-10-06	1974-05-31

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE12614/71A SE356754B (xx)	1971-10-06	1971-10-06
SE12613/71A SE359447B (xx)	1971-10-06	1971-10-06

Publications (2)

Publication Number	Publication Date
NO132521B true NO132521B (xx)	1975-08-18
NO132521C NO132521C (xx)	1975-11-26

Family

ID=26655894

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO356972A NO132521C (xx)	1971-10-06	1972-10-05

Country Status (21)

Country	Link
JP (1)	JPS4861611A (xx)
AR (1)	AR199188A1 (xx)
BE (1)	BE789758A (xx)
CA (1)	CA991544A (xx)
CH (1)	CH590891A5 (xx)
CS (1)	CS178876B2 (xx)
CY (1)	CY917A (xx)
DD (1)	DD105722A5 (xx)
DE (1)	DE2247021C3 (xx)
ES (1)	ES407332A1 (xx)
FI (1)	FI49475C (xx)
FR (1)	FR2157831B1 (xx)
GB (1)	GB1411266A (xx)
HU (2)	HU165476B (xx)
IE (2)	IE37760B1 (xx)
KE (1)	KE2757A (xx)
MY (1)	MY7800008A (xx)
NL (1)	NL162943C (xx)
NO (1)	NO132521C (xx)
SU (1)	SU730276A3 (xx)
TR (1)	TR17725A (xx)

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 IE135172A patent/IE37760B1/xx unknown
- 1972-10-05 CA CA153,317A patent/CA991544A/en not_active Expired
- 1972-10-05 JP JP9949872A patent/JPS4861611A/ja active Pending
- 1972-10-05 DD DD16604672A patent/DD105722A5/xx unknown
- 1972-10-05 NL NL7213482A patent/NL162943C/xx not_active IP Right Cessation
- 1972-10-05 CY CY91772A patent/CY917A/xx unknown
- 1972-10-05 IE IE94272A patent/IE37761B1/xx unknown
- 1972-10-05 GB GB4607472A patent/GB1411266A/en not_active Expired
- 1972-10-05 CS CS673572A patent/CS178876B2/cs unknown
- 1972-10-05 FR FR7235393A patent/FR2157831B1/fr not_active Expired
- 1972-10-05 FI FI275072A patent/FI49475C/fi active
- 1972-10-05 NO NO356972A patent/NO132521C/no unknown
- 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
IE37761L (en)	1973-04-06
IE37761B1 (en)	1977-10-12
BE789758A (fr)	1973-04-06
IE37760L (en)	1973-04-06
CS178876B2 (en)	1977-10-31
CH590891A5 (xx)	1977-08-31
NL162943B (nl)	1980-02-15
HU165476B (xx)	1974-09-28
JPS4861611A (xx)	1973-08-29
IE37760B1 (en)	1977-10-12
AR199188A1 (es)	1974-08-14
DE2247021A1 (de)	1973-04-12
GB1411266A (en)	1975-10-22
FR2157831A1 (xx)	1973-06-08
KE2757A (en)	1977-10-14
CY917A (en)	1977-12-23
DD105722A5 (xx)	1974-05-12
NO132521C (xx)	1975-11-26
MY7800008A (en)	1978-12-31
FI49475B (xx)	1975-04-01
SU730276A3 (ru)	1980-04-25
NL7213482A (xx)	1973-04-10
FI49475C (fi)	1975-07-10
HU164864B (xx)	1974-05-28
NL162943C (nl)	1980-07-15
ES407332A1 (es)	1976-01-16
TR17725A (tr)	1975-07-23
CA991544A (en)	1976-06-22
DE2247021B2 (de)	1978-12-14
FR2157831B1 (xx)	1976-04-23
DE2247021C3 (de)	1979-08-16

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DE938502C (de)	1956-02-02	Verfahren zur Herstellung einer kolloidalen Eisenzubereitung
US3965133A (en)	1976-06-22	Polymer
US3115488A (en)	1963-12-24	Alginic acid methyl ester sulfates, preparation and molecular weight fractionation thereof
NO134095B (xx)	1976-05-10