BE571750A - - Google Patents

Info

Publication number

BE571750A

BE571750A BE571750DA BE571750A BE 571750 A BE571750 A BE 571750A BE 571750D A BE571750D A BE 571750DA BE 571750 A BE571750 A BE 571750A

Authority

BE

Belgium

Prior art keywords

sep

salt

process according

water

dehydrocortisol

Prior art date

Links

• Espacenet
• Global Dossier
• Discuss

• 239000011780 sodium chloride Substances 0.000 claims description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N Prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 7
• VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 6
• 239000001632 sodium acetate Substances 0.000 claims description 6
• 235000017281 sodium acetate Nutrition 0.000 claims description 6
• 229910052783 alkali metal Inorganic materials 0.000 claims description 4
• -1 alkali metal salts Chemical class 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• OIGNJSKKLXVSLS-VWUMJDOOSA-N Prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 3
• 150000003512 tertiary amines Chemical class 0.000 claims description 3
• 239000002904 solvent Substances 0.000 claims description 2
• 238000000354 decomposition reaction Methods 0.000 claims 1
• 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 150000003839 salts Chemical class 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 159000000000 sodium salts Chemical class 0.000 description 5
• 229960004618 prednisone Drugs 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 239000003246 corticosteroid Substances 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 229940088597 Hormone Drugs 0.000 description 2
• 238000007792 addition Methods 0.000 description 2
• 150000001340 alkali metals Chemical group 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 150000008064 anhydrides Chemical class 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000005712 crystallization Effects 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 239000012442 inert solvent Substances 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 230000020477 pH reduction Effects 0.000 description 2
• 229960005205 prednisolone Drugs 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• QQCBOIWDENXRLP-BYZMTCBYSA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 description 1
• VTULJCFJIIAAIS-UHFFFAOYSA-N 2-(2-sulfobenzoyl)oxycarbonylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1S(O)(=O)=O VTULJCFJIIAAIS-UHFFFAOYSA-N 0.000 description 1
• 229940012356 Eye Drops Drugs 0.000 description 1
• IIMIOEBMYPRQGU-UHFFFAOYSA-L Picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 description 1
• 241001342522 Vampyrum spectrum Species 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000002421 anti-septic Effects 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 229920000591 gum Polymers 0.000 description 1
• 238000005360 mashing Methods 0.000 description 1
• 238000010907 mechanical stirring Methods 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 150000003138 primary alcohols Chemical group 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• HGKLFYLYWZXWPO-UHFFFAOYSA-N sulfo benzoate Chemical compound OS(=O)(=O)OC(=O)C1=CC=CC=C1 HGKLFYLYWZXWPO-UHFFFAOYSA-N 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• 125000000542 sulfonic acid group Chemical group 0.000 description 1
• 238000005406 washing Methods 0.000 description 1