BE542273A - - Google Patents

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Publication number: BE542273A
Authority: BE; Belgium
Prior art keywords: estrene; diol; parts; ethyl; mixture
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Publication of BE542273A publication Critical patent/BE542273A/fr

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-1 aliphatic ester Chemical class 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
238000005984 hydrogenation reaction Methods 0.000 claims description 10
YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 claims description 10
229910000033 sodium borohydride Inorganic materials 0.000 claims description 10
ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical group [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 claims description 10
CMXKUJNZWYTFJN-KPTXJRLASA-N (8R,9S,10R,13S,14S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)O)[C@@H]4[C@@H]3CCC2=C1 CMXKUJNZWYTFJN-KPTXJRLASA-N 0.000 claims description 9
125000004432 carbon atoms Chemical group C* 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 6
HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims description 6
OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical group [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims description 6
WITUGZWVTJUKIN-LHVXVHHKSA-N C(C)C1([C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O)O Chemical compound C(C)C1([C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O)O WITUGZWVTJUKIN-LHVXVHHKSA-N 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
238000006722 reduction reaction Methods 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
230000000875 corresponding Effects 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical group [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
229910000510 noble metal Inorganic materials 0.000 claims description 2
239000003638 reducing agent Substances 0.000 claims 3
229910052782 aluminium Inorganic materials 0.000 claims 2
KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 claims 2
125000001931 aliphatic group Chemical group 0.000 claims 1
150000004678 hydrides Chemical group 0.000 claims 1
230000000737 periodic Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
239000000203 mixture Substances 0.000 description 50
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 15
238000002844 melting Methods 0.000 description 13
239000003208 petroleum Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 11
229960000583 Acetic Acid Drugs 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000155 melt Substances 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000007792 addition Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
NPAGDVCDWIYMMC-IZPLOLCNSA-N Nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
229960004719 nandrolone Drugs 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
238000000862 absorption spectrum Methods 0.000 description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 4
230000005712 crystallization Effects 0.000 description 4
238000010828 elution Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
AYTHBBAKQYDEPO-UHFFFAOYSA-N ethylcyclohexane Chemical compound C[CH]C1CCCCC1 AYTHBBAKQYDEPO-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
NSUVCVKCWGOYPV-VXNCWWDNSA-N (8R,9S,13S,14S)-3-methoxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2C(CC=C(C3)OC)=C3CC[C@H]2[C@@H]2CCC(=O)[C@]21C NSUVCVKCWGOYPV-VXNCWWDNSA-N 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N Aluminium hydride Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
LGRKCTFWUWAKON-UHFFFAOYSA-N (13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl) propanoate Chemical compound C1CC2=CC(=O)CCC2C2C1C1CCC(OC(=O)CC)C1(C)CC2 LGRKCTFWUWAKON-UHFFFAOYSA-N 0.000 description 1
FBMXBXAYQCWEOC-PNKHAZJDSA-N (8R,9S,10R,13S,14S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 FBMXBXAYQCWEOC-PNKHAZJDSA-N 0.000 description 1
RMHYLJRJKMRKNU-LHVXVHHKSA-N (8R,9S,10R,13S,14S)-17-ethenyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)(O)C=C)[C@@H]4[C@@H]3CCC2=C1 RMHYLJRJKMRKNU-LHVXVHHKSA-N 0.000 description 1
XFHYFANAUUFBKA-HWSKEQOTSA-N (9R,10S,13S)-13-methyl-1,2,3,4,5,6,9,10,11,12-decahydrocyclopenta[a]phenanthren-17-ol Chemical compound C([C@@H]12)CCCC1CC=C1[C@@H]2CC[C@@]2(C)C1=CC=C2O XFHYFANAUUFBKA-HWSKEQOTSA-N 0.000 description 1
150000000319 19-nortestosterones Chemical class 0.000 description 1
CPBZARXQRZTYGI-UHFFFAOYSA-N 3-cyclopentylpropylcyclohexane Chemical compound C1CCCCC1CCCC1CCCC1 CPBZARXQRZTYGI-UHFFFAOYSA-N 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N Allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
UBHQLLAKFJFJIP-ZWJUHJGLSA-N C(=C)C[C@@]12C(CC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O)O Chemical compound C(=C)C[C@@]12C(CC[C@H]1[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O)O UBHQLLAKFJFJIP-ZWJUHJGLSA-N 0.000 description 1
XAJLLTOCAVCFMD-FGRTTXBXSA-N C(C)(=O)OC1C=C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@H]2CC1)OC(C)=O Chemical compound C(C)(=O)OC1C=C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@H]2CC1)OC(C)=O XAJLLTOCAVCFMD-FGRTTXBXSA-N 0.000 description 1
DTLXGBVZQJNXSW-GTXUSFTJSA-N C(C1=CC=CC=C1)(=O)OC1C=C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@H]2CC1)OC(C1=CC=CC=C1)=O Chemical compound C(C1=CC=CC=C1)(=O)OC1C=C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@H]2CC1)OC(C1=CC=CC=C1)=O DTLXGBVZQJNXSW-GTXUSFTJSA-N 0.000 description 1
GBPNCYLXENMGOA-ZPKHMHQSSA-N C(CC)(=O)OC1[C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O Chemical compound C(CC)(=O)OC1[C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O GBPNCYLXENMGOA-ZPKHMHQSSA-N 0.000 description 1
DWFMPFXGLYALHM-SIOKIZADSA-N CC1([C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O)O Chemical compound CC1([C@]2(C)[C@@H](CC1)[C@@H]1CCC3=CC(CC[C@@H]3[C@H]1CC2)O)O DWFMPFXGLYALHM-SIOKIZADSA-N 0.000 description 1
229960003563 Calcium Carbonate Drugs 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
238000003612 Meerwein-Ponndorf-Verley reduction reaction Methods 0.000 description 1
ZDHCJEIGTNNEMY-XGXHKTLJSA-N Norethandrolone Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](CC)(O)[C@@]1(C)CC2 ZDHCJEIGTNNEMY-XGXHKTLJSA-N 0.000 description 1
VIKNJXKGJWUCNN-XGXHKTLJSA-N Norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
229940103091 Potassium Benzoate Drugs 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M Potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
239000003263 anabolic agent Substances 0.000 description 1
239000003098 androgen Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000002934 lysing Effects 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000004300 potassium benzoate Substances 0.000 description 1
235000010235 potassium benzoate Nutrition 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003860 storage Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1

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BE542273D BE542273A (fi)

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Publication Number	Publication Date
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