BE529972A

BE529972A -

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Publication number: BE529972A
Authority: BE; Belgium
Prior art keywords: chloroform; solution; water; mixture; acetate
Prior art date

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English (en)

French (fr)

Publication of BE529972A publication Critical patent/BE529972A/fr

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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 60
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 45
239000000243 solution Substances 0.000 claims 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 24
239000000203 mixture Substances 0.000 claims 24
150000001875 compounds Chemical class 0.000 claims 22
238000000034 method Methods 0.000 claims 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 17
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 15
239000003638 chemical reducing agent Substances 0.000 claims 15
239000005977 Ethylene Substances 0.000 claims 14
229910052794 bromium Inorganic materials 0.000 claims 13
238000004364 calculation method Methods 0.000 claims 13
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
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
229960000583 acetic acid Drugs 0.000 claims 8
239000001569 carbon dioxide Substances 0.000 claims 8
238000002844 melting Methods 0.000 claims 8
230000008018 melting Effects 0.000 claims 8
239000012071 phase Substances 0.000 claims 8
238000001953 recrystallisation Methods 0.000 claims 8
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims 7
229910021554 Chromium(II) chloride Inorganic materials 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
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims 7
XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 claims 7
229940109126 chromous chloride Drugs 0.000 claims 7
229960004544 cortisone Drugs 0.000 claims 7
229910052739 hydrogen Inorganic materials 0.000 claims 7
239000000047 product Substances 0.000 claims 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
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
239000013078 crystal Substances 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
-1 3-ketone steroids Chemical class 0.000 claims 5
238000000862 absorption spectrum Methods 0.000 claims 5
230000015572 biosynthetic process Effects 0.000 claims 5
238000002425 crystallisation Methods 0.000 claims 5
230000008025 crystallization Effects 0.000 claims 5
150000002576 ketones Chemical class 0.000 claims 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 5
239000007787 solid Substances 0.000 claims 5
239000012453 solvate Substances 0.000 claims 5
238000012360 testing method Methods 0.000 claims 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
238000010521 absorption reaction Methods 0.000 claims 4
239000002253 acid Substances 0.000 claims 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims 4
238000006243 chemical reaction Methods 0.000 claims 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
238000010992 reflux Methods 0.000 claims 4
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
239000008346 aqueous phase Substances 0.000 claims 3
239000007864 aqueous solution Substances 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 3
LRCIYVMVWAMTKX-UHFFFAOYSA-L chromium(ii) acetate Chemical compound [Cr+2].CC([O-])=O.CC([O-])=O LRCIYVMVWAMTKX-UHFFFAOYSA-L 0.000 claims 3
238000001816 cooling Methods 0.000 claims 3
238000001704 evaporation Methods 0.000 claims 3
230000008020 evaporation Effects 0.000 claims 3
239000000284 extract Substances 0.000 claims 3
239000001257 hydrogen Substances 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
230000003287 optical effect Effects 0.000 claims 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
239000011343 solid material Substances 0.000 claims 3
238000003786 synthesis reaction Methods 0.000 claims 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 2
VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 claims 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone 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 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 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
229910021626 Tin(II) chloride Inorganic materials 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 effect 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
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 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
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
238000002329 infrared spectrum Methods 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
230000007935 neutral effect Effects 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
229940107700 pyruvic acid Drugs 0.000 claims 2
229920006395 saturated elastomer Polymers 0.000 claims 2
238000001228 spectrum Methods 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
238000005406 washing Methods 0.000 claims 2
OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 1
RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims 1
NIOCRRWZBFJEPT-GGLGBZJVSA-N (8S,9S,10R,13R,14S,17R)-4-bromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one 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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
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
OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
229910021559 Chromium(II) bromide Inorganic materials 0.000 claims 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-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
OXLGJTRVVNGJRK-UHFFFAOYSA-N Hecogenin Natural products CC1CCC2(CC3CC4C5CCC6CC(O)CCC6(C)C5CC(=O)C4(C)C3C2C)OC1 OXLGJTRVVNGJRK-UHFFFAOYSA-N 0.000 claims 1
WVVOBOZHTQJXPB-UHFFFAOYSA-N N-anilino-N-nitronitramide Chemical compound [N+](=O)([O-])N(NC1=CC=CC=C1)[N+](=O)[O-] WVVOBOZHTQJXPB-UHFFFAOYSA-N 0.000 claims 1
UVLDESQWQRMYKD-UHFFFAOYSA-N Neobotogenin Natural products CC1C(C2(C(=O)CC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 UVLDESQWQRMYKD-UHFFFAOYSA-N 0.000 claims 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
229930182558 Sterol Natural products 0.000 claims 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 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
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
238000004458 analytical method Methods 0.000 claims 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims 1
230000031709 bromination Effects 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
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 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
XZQOHYZUWTWZBL-UHFFFAOYSA-L chromium(ii) bromide Chemical group [Cr+2].[Br-].[Br-] XZQOHYZUWTWZBL-UHFFFAOYSA-L 0.000 claims 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims 1
229940125782 compound 2 Drugs 0.000 claims 1
239000010949 copper Substances 0.000 claims 1
239000002178 crystalline material Substances 0.000 claims 1
230000018044 dehydration Effects 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
CPELXLSAUQHCOX-DYCDLGHISA-N deuterium bromide Chemical compound [2H]Br CPELXLSAUQHCOX-DYCDLGHISA-N 0.000 claims 1
238000010790 dilution Methods 0.000 claims 1
239000012895 dilution Substances 0.000 claims 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
238000004821 distillation Methods 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
DNVPQKQSNYMLRS-SOWFXMKYSA-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-SOWFXMKYSA-N 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
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 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
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
238000009434 installation Methods 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
239000012280 lithium aluminium hydride Substances 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
ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-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
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 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
DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 claims 1
239000002245 particle Substances 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 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
235000009518 sodium iodide Nutrition 0.000 claims 1
150000003432 sterols Chemical class 0.000 claims 1
235000003702 sterols Nutrition 0.000 claims 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims 1
229960003604 testosterone Drugs 0.000 claims 1
239000010936 titanium Substances 0.000 claims 1
229910052719 titanium Inorganic materials 0.000 claims 1
229910000348 titanium sulfate Inorganic materials 0.000 claims 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
230000001052 transient effect Effects 0.000 claims 1
230000004580 weight loss Effects 0.000 claims 1
101100384355 Mus musculus Ctnnbip1 gene Proteins 0.000 description 1