BE529972A - - Google Patents
Info
- Publication number
- BE529972A BE529972A BE529972DA BE529972A BE 529972 A BE529972 A BE 529972A BE 529972D A BE529972D A BE 529972DA BE 529972 A BE529972 A BE 529972A
- Authority
- BE
- Belgium
- Prior art keywords
- chloroform
- solution
- water
- mixture
- acetate
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 58
- 239000000243 solution Substances 0.000 claims 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 26
- 239000000203 mixture Substances 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 15
- 238000000034 method Methods 0.000 claims 15
- 239000003638 reducing agent Substances 0.000 claims 15
- 239000005977 Ethylene Substances 0.000 claims 14
- 238000004364 calculation method Methods 0.000 claims 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- 239000011541 reaction mixture Substances 0.000 claims 12
- 238000006722 reduction reaction Methods 0.000 claims 12
- 239000002904 solvent Substances 0.000 claims 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 10
- 229960000583 Acetic Acid Drugs 0.000 claims 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 9
- 125000000468 ketone group Chemical group 0.000 claims 9
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 8
- 239000001569 carbon dioxide Substances 0.000 claims 8
- 238000002844 melting Methods 0.000 claims 8
- 239000012071 phase Substances 0.000 claims 8
- 238000001953 recrystallisation Methods 0.000 claims 8
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L Chromium(II) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 claims 7
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims 7
- 229940109126 chromous chloride Drugs 0.000 claims 7
- 229960004544 cortisone Drugs 0.000 claims 7
- 239000000047 product Substances 0.000 claims 7
- ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 claims 6
- 229960003290 cortisone acetate Drugs 0.000 claims 6
- 238000000354 decomposition reaction Methods 0.000 claims 6
- 239000007858 starting material Substances 0.000 claims 6
- 238000003756 stirring Methods 0.000 claims 6
- 238000000862 absorption spectrum Methods 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 230000005712 crystallization Effects 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 150000002576 ketones Chemical class 0.000 claims 5
- 239000007787 solid Substances 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 4
- 238000010521 absorption reaction Methods 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 238000002425 crystallisation Methods 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- LCTONWCANYUPML-UHFFFAOYSA-N pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- LRCIYVMVWAMTKX-UHFFFAOYSA-L Chromium(II) acetate Chemical compound [Cr+2].CC([O-])=O.CC([O-])=O LRCIYVMVWAMTKX-UHFFFAOYSA-L 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- 239000008346 aqueous phase Substances 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 3
- -1 ethyl acetal Chemical class 0.000 claims 3
- 238000001704 evaporation Methods 0.000 claims 3
- 239000000284 extract Substances 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 3
- 239000000543 intermediate Substances 0.000 claims 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 3
- 230000003287 optical Effects 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 239000011343 solid material Substances 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- 230000002194 synthesizing Effects 0.000 claims 3
- DIKBFYAXUHHXCS-UHFFFAOYSA-N Bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims 2
- 210000004940 Nucleus Anatomy 0.000 claims 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 2
- 229940107700 Pyruvic Acid Drugs 0.000 claims 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 2
- 229910001115 Zinc-copper couple Inorganic materials 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 230000001476 alcoholic Effects 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229950005228 bromoform Drugs 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 239000012043 crude product Substances 0.000 claims 2
- 238000000921 elemental analysis Methods 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 2
- 238000002329 infrared spectrum Methods 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 239000010410 layer Substances 0.000 claims 2
- 230000031700 light absorption Effects 0.000 claims 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims 2
- 239000000155 melt Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000001264 neutralization Effects 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- 238000001228 spectrum Methods 0.000 claims 2
- 229940013123 stannous chloride Drugs 0.000 claims 2
- 239000001119 stannous chloride Substances 0.000 claims 2
- 235000011150 stannous chloride Nutrition 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin dichloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-Dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 claims 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- XSJVWZAETSBXKU-UHFFFAOYSA-N 2-ethoxypropane Chemical compound CCOC(C)C XSJVWZAETSBXKU-UHFFFAOYSA-N 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- NIOCRRWZBFJEPT-GGLGBZJVSA-N BrC1C2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CCC1=O)C)C)[C@H](C)CCCC(C)C Chemical compound BrC1C2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CCC1=O)C)C)[C@H](C)CCCC(C)C NIOCRRWZBFJEPT-GGLGBZJVSA-N 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 1
- DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 claims 1
- DNVPQKQSNYMLRS-LNHMRCHQSA-N Ergosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3C([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)=CC=2)CC1 DNVPQKQSNYMLRS-LNHMRCHQSA-N 0.000 claims 1
- QOLRLLFJMZLYQJ-LOBDNJQFSA-N Hecogenin Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QOLRLLFJMZLYQJ-LOBDNJQFSA-N 0.000 claims 1
- QOLRLLFJMZLYQJ-GSSCIUJHSA-N Hecogenin Natural products O=C1[C@]2(C)[C@H]3[C@H](C)[C@@]4(O[C@H]3C[C@H]2[C@@H]2[C@@H]([C@]3(C)[C@H](C[C@@H](O)CC3)CC2)C1)OC[C@H](C)CC4 QOLRLLFJMZLYQJ-GSSCIUJHSA-N 0.000 claims 1
- 229940050176 Methyl Chloride Drugs 0.000 claims 1
- 241001182492 Nes Species 0.000 claims 1
- RJKFOVLPORLFTN-STHVQZNPSA-N Progesterone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC(=O)CC4)CC3)CC2)CC1 RJKFOVLPORLFTN-STHVQZNPSA-N 0.000 claims 1
- 229940083599 Sodium Iodide Drugs 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Syngestrets Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 1
- 229960003604 Testosterone Drugs 0.000 claims 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J Titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
- CQODGVQBRIGKLJ-UHFFFAOYSA-L [Na+].[Na+].[O-]OOO[O-] Chemical compound [Na+].[Na+].[O-]OOO[O-] CQODGVQBRIGKLJ-UHFFFAOYSA-L 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 150000001844 chromium Chemical class 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 239000002178 crystalline material Substances 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000007269 dehydrobromination reaction Methods 0.000 claims 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims 1
- RYPWQHONZWFXBN-UHFFFAOYSA-N dichloromethyl(methylidene)-$l^{3}-chlorane Chemical compound ClC(Cl)Cl=C RYPWQHONZWFXBN-UHFFFAOYSA-N 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 238000003306 harvesting Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000008079 hexane Substances 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000009434 installation Methods 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 229960003387 progesterone Drugs 0.000 claims 1
- 239000000186 progesterone Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- 150000003432 sterols Chemical class 0.000 claims 1
- 235000003702 sterols Nutrition 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 229910000348 titanium sulfate Inorganic materials 0.000 claims 1
- HDUMBHAAKGUHAR-UHFFFAOYSA-J titanium(4+);disulfate Chemical compound [Ti+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O HDUMBHAAKGUHAR-UHFFFAOYSA-J 0.000 claims 1
- 230000001052 transient Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
- 108060001986 CTNNBIP1 Proteins 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE529972A true BE529972A (es) |
Family
ID=162774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE529972D BE529972A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE529972A (es) |
-
0
- BE BE529972D patent/BE529972A/fr unknown
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