BE520416A - - Google Patents

Info

Publication number

BE520416A

BE520416A BE520416DA BE520416A BE 520416 A BE520416 A BE 520416A BE 520416D A BE520416D A BE 520416DA BE 520416 A BE520416 A BE 520416A

Authority

BE

Belgium

Prior art keywords

acetyldigitoxin

filtered

solution

methyl alcohol

water

Prior art date

Links

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• Global Dossier
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
• 238000010438 heat treatment Methods 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 5
• 230000002378 acidificating effect Effects 0.000 claims description 2
• 230000007935 neutral effect Effects 0.000 claims description 2
• 239000003960 organic solvent Substances 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 238000010992 reflux Methods 0.000 description 5
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• HPMZBILYSWLILX-UMDUKNJSSA-N 3'''-O-acetyldigitoxin Chemical compound C1[C@H](OC(C)=O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O HPMZBILYSWLILX-UMDUKNJSSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• HPMZBILYSWLILX-UHFFFAOYSA-N Acetyl-digitoxine Natural products C1C(OC(C)=O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O HPMZBILYSWLILX-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• 229960003635 acetyldigitoxin Drugs 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• FDWRIIDFYSUTDP-UHFFFAOYSA-N 102850-49-7 Natural products CC1OC(O)CC(O)C1O FDWRIIDFYSUTDP-UHFFFAOYSA-N 0.000 description 2
• JWFRNGYBHLBCMB-UHFFFAOYSA-N D-Canaytose Natural products CC(O)C(O)C(O)CC=O JWFRNGYBHLBCMB-UHFFFAOYSA-N 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 235000019441 ethanol Nutrition 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000002035 prolonged effect Effects 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• FDWRIIDFYSUTDP-KVTDHHQDSA-N (2r,4r,5s,6r)-6-methyloxane-2,4,5-triol Chemical compound C[C@H]1O[C@@H](O)C[C@@H](O)[C@@H]1O FDWRIIDFYSUTDP-KVTDHHQDSA-N 0.000 description 1
• 241000812324 Digitalis ferruginea Species 0.000 description 1
• 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 1
• YFGQJKBUXPKSAW-UHFFFAOYSA-N Lanatosid A Natural products CC1OC(OC2CC3C(C4C(C5(CCC(C5(C)CC4)C=4COC(=O)C=4)O)CC3)(C)CC2)CC(O)C1OC(OC1C)CC(O)C1OC(OC1C)CC(OC(C)=O)C1OC1OC(CO)C(O)C(O)C1O YFGQJKBUXPKSAW-UHFFFAOYSA-N 0.000 description 1
• YFGQJKBUXPKSAW-YSTAXILLSA-N Lanatoside A Chemical compound O([C@H]1[C@@H](OC(C)=O)C[C@@H](O[C@@H]1C)O[C@H]1[C@@H](O)C[C@@H](O[C@@H]1C)O[C@H]1[C@@H](O)C[C@@H](O[C@@H]1C)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@H]([C@]4(CC[C@@H]([C@@]4(C)CC3)C=3COC(=O)C=3)O)CC2)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YFGQJKBUXPKSAW-YSTAXILLSA-N 0.000 description 1
• XZTUSOXSLKTKJQ-UHFFFAOYSA-N Uzarigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C1=CC(=O)OC1 XZTUSOXSLKTKJQ-UHFFFAOYSA-N 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 238000010504 bond cleavage reaction Methods 0.000 description 1
• 230000003177 cardiotonic effect Effects 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• XZTUSOXSLKTKJQ-CESUGQOBSA-N digitoxigenin Chemical compound C1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)=CC(=O)OC1 XZTUSOXSLKTKJQ-CESUGQOBSA-N 0.000 description 1
• QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 231100000053 low toxicity Toxicity 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 230000037452 priming Effects 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 230000017105 transposition Effects 0.000 description 1