BE519105A - - Google Patents

Info

Publication number

BE519105A

BE519105A BE519105DA BE519105A BE 519105 A BE519105 A BE 519105A BE 519105D A BE519105D A BE 519105DA BE 519105 A BE519105 A BE 519105A

Authority

BE

Belgium

Prior art keywords

monosulfate

equiline

salt

dimethylpiperazine

mixture

Prior art date

Links

• Espacenet
• Global Dossier
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• NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 claims description 32
• WKRLQDKEXYKHJB-UHFFFAOYSA-N Equilin Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3=CCC2=C1 WKRLQDKEXYKHJB-UHFFFAOYSA-N 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 24
• 239000000203 mixture Substances 0.000 claims description 19
• 150000001875 compounds Chemical class 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 10
• WKRLQDKEXYKHJB-HFTRVMKXSA-N equilin Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 WKRLQDKEXYKHJB-HFTRVMKXSA-N 0.000 claims description 9
• 229940011871 estrogen Drugs 0.000 claims description 8
• 239000000262 estrogen Substances 0.000 claims description 8
• PDRGHUMCVRDZLQ-WMZOPIPTSA-N equilenin Chemical class OC1=CC=C2C(CC[C@]3([C@H]4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-WMZOPIPTSA-N 0.000 claims description 7
• 239000011541 reaction mixture Substances 0.000 claims description 6
• 229910052783 alkali metal Inorganic materials 0.000 claims description 5
• 150000001340 alkali metals Chemical class 0.000 claims description 5
• 239000012431 aqueous reaction media Substances 0.000 claims description 4
• 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 claims description 3
• 229910052936 alkali metal sulfate Inorganic materials 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 239000011734 sodium Substances 0.000 claims description 3
• 150000002167 estrones Chemical class 0.000 claims description 2
• 239000012429 reaction media Substances 0.000 claims 4
• 239000012736 aqueous medium Substances 0.000 claims 2
• 239000002609 medium Substances 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
• 150000002576 ketones Chemical class 0.000 description 7
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• PDRGHUMCVRDZLQ-UHFFFAOYSA-N d-equilenin Natural products OC1=CC=C2C(CCC3(C4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-UHFFFAOYSA-N 0.000 description 5
• 230000001076 estrogenic effect Effects 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• 229910021653 sulphate ion Inorganic materials 0.000 description 4
• DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 3
• DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 3
• 238000009835 boiling Methods 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 229960003399 estrone Drugs 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 238000011084 recovery Methods 0.000 description 3
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
• JKKFKPJIXZFSSB-UHFFFAOYSA-N 1,3,5(10)-estratrien-17-one 3-sulfate Natural products OS(=O)(=O)OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 JKKFKPJIXZFSSB-UHFFFAOYSA-N 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• YJBYRYVLFAUXBJ-HFTRVMKXSA-N [(9s,13s,14s)-13-methyl-17-oxo-9,11,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 YJBYRYVLFAUXBJ-HFTRVMKXSA-N 0.000 description 2
• OVENUVCCLMAWKX-UHFFFAOYSA-N acetic acid 2,5-dimethylpiperazine Chemical compound C(C)(=O)O.CC1NCC(NC1)C OVENUVCCLMAWKX-UHFFFAOYSA-N 0.000 description 2
• JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 2
• 239000000284 extract Substances 0.000 description 2
• -1 ketone sulfates Chemical class 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• 238000000862 absorption spectrum Methods 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 239000012971 dimethylpiperazine Substances 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1