BE527760A

BE527760A -

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Publication number: BE527760A
Authority: BE; Belgium
Prior art keywords: steroid; alkali metal; molar equivalents; acid; keto
Prior art date

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English (en)

French (fr)

Publication of BE527760A publication Critical patent/BE527760A/fr

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150000003431 steroids Chemical class 0.000 claims description 154
229910052783 alkali metal Inorganic materials 0.000 claims description 94
150000001340 alkali metals Chemical class 0.000 claims description 86
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 79
239000002585 base Substances 0.000 claims description 78
239000002253 acid Substances 0.000 claims description 67
238000000034 method Methods 0.000 claims description 62
239000000047 product Substances 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 60
239000003795 chemical substances by application Substances 0.000 claims description 55
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 50
-1 alkyl ester steroid Chemical class 0.000 claims description 48
238000006243 chemical reaction Methods 0.000 claims description 47
239000011541 reaction mixture Substances 0.000 claims description 47
WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 44
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 36
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
238000005658 halogenation reaction Methods 0.000 claims description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 28
150000004702 methyl esters Chemical class 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 25
239000007795 chemical reaction product Substances 0.000 claims description 23
238000007792 addition Methods 0.000 claims description 19
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 16
235000006408 oxalic acid Nutrition 0.000 claims description 16
239000007859 condensation product Substances 0.000 claims description 15
WKAVAGKRWFGIEA-DADBAOPHSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione 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=O WKAVAGKRWFGIEA-DADBAOPHSA-N 0.000 claims description 14
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 14
210000004940 Nucleus Anatomy 0.000 claims description 13
125000005907 alkyl ester group Chemical group 0.000 claims description 13
DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 13
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
239000011734 sodium Substances 0.000 claims description 12
229910052708 sodium Inorganic materials 0.000 claims description 12
239000011701 zinc Substances 0.000 claims description 12
229910052725 zinc Inorganic materials 0.000 claims description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 11
230000002140 halogenating Effects 0.000 claims description 10
239000000186 progesterone Substances 0.000 claims description 10
239000011780 sodium chloride Substances 0.000 claims description 10
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 description 9
239000003960 organic solvent Substances 0.000 claims description 8
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
229960003387 progesterone Drugs 0.000 claims description 7
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 description 6
150000002148 esters Chemical class 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
125000004429 atoms Chemical group 0.000 claims description 5
239000007810 chemical reaction solvent Substances 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
239000001632 sodium acetate Substances 0.000 claims description 3
235000017281 sodium acetate Nutrition 0.000 claims description 3
BFZHCUBIASXHPK-AYHYENMDSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2O BFZHCUBIASXHPK-AYHYENMDSA-N 0.000 claims description 2
DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 claims description 2
238000005893 bromination reaction Methods 0.000 claims description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 2
238000009472 formulation Methods 0.000 claims 2
GCVXWIQSHQJQAX-OBQKJFGGSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,6,7,8,9,11,12,14,15,17-decahydro-1H-cyclopenta[a]phenanthrene-3,16-dione Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=O)[C@H](C(=O)C)[C@@]1(C)CC2 GCVXWIQSHQJQAX-OBQKJFGGSA-N 0.000 claims 1
DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 claims 1
QACJNLFCDPDUNE-UHFFFAOYSA-N 2-[[4-(carboxymethylamino)-6-chloro-1,3,5-triazin-2-yl]amino]acetic acid Chemical compound OC(=O)CNC1=NC(Cl)=NC(NCC(O)=O)=N1 QACJNLFCDPDUNE-UHFFFAOYSA-N 0.000 claims 1
WAXHLCGFBHHJQH-PLGLBBQFSA-N C(C=C1C=C[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)(=O)O Chemical compound C(C=C1C=C[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)(=O)O WAXHLCGFBHHJQH-PLGLBBQFSA-N 0.000 claims 1
NIFHFRBCEUSGEE-UHFFFAOYSA-N OC(=O)C(O)=O.OC(=O)C(O)=O Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O NIFHFRBCEUSGEE-UHFFFAOYSA-N 0.000 claims 1
229940039790 Sodium Oxalate Drugs 0.000 claims 1
ZNCPFRVNHGOPAG-UHFFFAOYSA-L Sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
229960002899 hydroxyprogesterone Drugs 0.000 claims 1
239000012071 phase Substances 0.000 description 79
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 40
239000000243 solution Substances 0.000 description 35
150000001875 compounds Chemical class 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
239000002904 solvent Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000004519 manufacturing process Methods 0.000 description 14
229960000583 Acetic Acid Drugs 0.000 description 13
238000002955 isolation Methods 0.000 description 13
239000000460 chlorine Substances 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
239000000463 material Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000007858 starting material Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
239000008079 hexane Substances 0.000 description 7
SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
238000002844 melting Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000000376 reactant Substances 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxalate, Glyoxylate Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 5
FKHIFSZMMVMEQY-UHFFFAOYSA-N Talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000000391 magnesium silicate Substances 0.000 description 5
229910052919 magnesium silicate Inorganic materials 0.000 description 5
235000019792 magnesium silicate Nutrition 0.000 description 5
JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229910052762 osmium Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229940088597 Hormone Drugs 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
230000000875 corresponding Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000005556 hormone Substances 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
235000011056 potassium acetate Nutrition 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000003146 progesterones Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000001603 reducing Effects 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
230000017105 transposition Effects 0.000 description 3
KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
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 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N Potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N Silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000001441 androstanes Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000001054 cortical Effects 0.000 description 2
229960004544 cortisone Drugs 0.000 description 2
238000005695 dehalogenation reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
125000002587 enol group Chemical group 0.000 description 2
150000002085 enols Chemical class 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 2
OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
RLEFZEWKMQQZOA-UHFFFAOYSA-N potassium;octanoic acid Chemical class [K+].CCCCCCCC(O)=O RLEFZEWKMQQZOA-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
BDFMJYFTJSHIQO-XRFJLBFOSA-N (8R,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,6,7,8,9,11,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,12-dione 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)C(=O)C2 BDFMJYFTJSHIQO-XRFJLBFOSA-N 0.000 description 1
CPUKWYXYHPOQJH-RDQPJNLGSA-N (8R,9S,10S,13S,14S)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(=CC4)C=C)[C@@H]4[C@@H]3CCC21 CPUKWYXYHPOQJH-RDQPJNLGSA-N 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N (8S,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
BFZHCUBIASXHPK-ATWVFEABSA-N 11β-hydroxyprogesterone 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)C[C@@H]2O BFZHCUBIASXHPK-ATWVFEABSA-N 0.000 description 1
VRRHHTISESGZFN-RKFFNLMFSA-N 16,17-didehydroprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 VRRHHTISESGZFN-RKFFNLMFSA-N 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N Aluminium hydride Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M Benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
IUPIXXQDZJLYEE-VVOHEPDNSA-N BrC1CC=C2CC[C@H]3[C@@H]4CCC(=CC(=O)OC)[C@]4(CC[C@@H]3[C@]2(C1)C)C Chemical compound BrC1CC=C2CC[C@H]3[C@@H]4CCC(=CC(=O)OC)[C@]4(CC[C@@H]3[C@]2(C1)C)C IUPIXXQDZJLYEE-VVOHEPDNSA-N 0.000 description 1
HHSZZZVZSWJGFD-YEVQUHCQSA-N COC(C=C1C=C[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O Chemical compound COC(C=C1C=C[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O HHSZZZVZSWJGFD-YEVQUHCQSA-N 0.000 description 1
229960003563 Calcium Carbonate Drugs 0.000 description 1
AHXGRMIPHCAXFP-UHFFFAOYSA-L Chromyl chloride Chemical compound Cl[Cr](Cl)(=O)=O AHXGRMIPHCAXFP-UHFFFAOYSA-L 0.000 description 1
JYGXADMDTFJGBT-VWUMJDOOSA-N Cortisol Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 1
LOMVENUNSWAXEN-UHFFFAOYSA-N Dimethyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
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